salicylates and methyl-salicylate

Methyl salicylate (MeSal) is an organic compound present in plants during stress events and is therefore a key marker for early plant disease detection. It has usually been detected by conventional methods that require bulky and costly equipment, such as gas chromatography or mass spectrometry. Currently, however, chemical sensors provide an alternative for MeSal monitoring, showing good performance for its determination in the vapour or liquid phase. The most promising concepts used in MeSal determination include sensors based on electrochemical and conductometric principles, although other technologies based on mass-sensitive, microwave, or spectrophotometric principles also show promise. The receptor elements or sensitive materials are shown to be part of the key elements in these sensing technologies. A literature survey identified a significant contribution of bioreceptors, including enzymes, odourant-binding proteins or peptides, as well as receptors based on polymers or inorganic materials in MeSal determination. This work reviews these concepts and materials and discusses their future prospects and limitations for application in plant health monitoring.

Topics: Agriculture; Biosensing Techniques; Conductometry; Salicylates

Methyl salicylate is a volatile compound, the synthesis of which takes place via the salicylic acid pathway in plants. Both compounds can be involved in the development of systemic acquired resistance and they play their role partly independently. Salicylic acid transport has an important role in long-distance signalling, but methyl salicylate has also been suggested as a phloem-based mobile signal, which can be demethylated to form salicylic acid, inducing the de-novo synthesis of salicylic acid in distal tissue. Despite the fact that salicylic acid has a protective role in abiotic stress responses and tolerance, very few investigations have been reported on the similar effects of methyl salicylate. In addition, as salicylic acid and methyl salicylate are often treated simply as the volatile and non-volatile forms of the same compound, and in several cases they also act in the same way, it is hard to highlight the differences in their mode of action. The main aim of the present review is to reveal the individual role and action mechanism of methyl salicylate in systemic acquired resistance, plant-plant communication and various stress conditions in fruits and plants.

Topics: Phloem; Plant Development; Plants; Salicylates; Salicylic Acid

Semiochemical use is a promising way to reduce damage from pests by improving natural control in agro-ecosystems. The aphid alarm pheromone (E)-β-farnesene (EβF) and herbivore-induced methyl salicylate (MeSA) are two volatile cues to induce changes in aphid behavior with functional significance. Because of limitations related to the volatility and oxidization of EβF and MeSA under natural conditions, slow-release and antioxidant techniques should be developed and optimized before application. Here, a slow-release alginate bead of EβF mixed with MeSA was first designed and manufactured. We hypothesized that a mixture of these two semiochemicals could be effective in controlling Sitobion miscanthi in wheat crops. Both MeSA and EβF in alginate beads were released stably and continuously for at least 15 days in the laboratory, whereas EβF in paraffin oil and pure MeSA were released for only 2 and 7 days, respectively. In 2018 field experiments, EβF and MeSA alone or in association significantly decreased the abundance of alate and apterous aphids. An increased abundance of mummified aphids enhanced by higher parasitism rates was observed when using EβF and MeSA in association, with a significant reduction of apterous abundance, more so than EβF or MeSA alone. In 2019, plots treated with a mixture of EβF and MeSA showed significantly decreased abundance of alate and apterous aphids with higher parasitism rates compared with the control. The new slow-release alginate bead containing a mixture of EβF with MeSA could be the most efficient formulation to control S. miscanthi population by attracting parasitoids in the wheat agro-ecosystem. © 2021 Society of Chemical Industry. © 2021 Society of Chemical Industry.

Topics: Animals; Aphids; Ecosystem; Pheromones; Salicylates; Sesquiterpenes; Triticum

In this short review, we attempt to unfold various aspects of excited-state intramolecular proton transfer (ESIPT) from the studies that are available up to date. Since Weller's discovery of ESIPT in salicylic acid (SA) and its derivative methyl salicylate (MS), numerous studies have emerged on the topic and it has become an attractive field of research because of its manifold applications. Here, we discuss some critical aspects of ESIPT and tautomerization from the mechanistic viewpoint. We address excitation wavelength dependence, anti-Kasha ESIPT, fast and slow ESIPT, reversibility and irreversibility of ESIPT, hydrogen bonding and geometrical factors, excited-state double proton transfer (ESDPT), concerted and stepwise ESDPT.

Topics: Electrons; Hydrogen; Hydrogen Bonding; Ions; Models, Molecular; Protons; Quantum Theory; Salicylates; Salicylic Acid; Thermodynamics

Incidents involving the release of chemical agents can pose significant risks to public health. In such an event, emergency decontamination of affected casualties may need to be undertaken to reduce injury and possible loss of life. To ensure these methods are effective, human volunteer trials (HVTs) of decontamination protocols, using simulant contaminants, have been conducted. Simulants must be used to mimic the physicochemical properties of more harmful chemicals, while remaining non-toxic at the dose applied. This review focuses on studies that employed chemical warfare agent simulants in decontamination contexts, to identify those simulants most suitable for use in HVTs of emergency decontamination. Twenty-two simulants were identified, of which 17 were determined unsuitable for use in HVTs. The remaining simulants (n = 5) were further scrutinized for potential suitability according to toxicity, physicochemical properties and similarities to their equivalent toxic counterparts. Three suitable simulants, for use in HVTs were identified; methyl salicylate (simulant for sulphur mustard), diethyl malonate (simulant for soman) and malathion (simulant for VX or toxic industrial chemicals). All have been safely used in previous HVTs, and have a range of physicochemical properties that would allow useful inference to more toxic chemicals when employed in future studies of emergency decontamination systems.

Topics: Chemical Warfare Agents; Databases, Factual; Decontamination; Healthy Volunteers; Humans; In Vitro Techniques; Lethal Dose 50; Malathion; Malonates; Salicylates

Methyl salicylate is the predominant constituent of oil of wintergreen and is used as a pesticide, a denaturant, an external analgesic, a fragrance ingredient, and a flavoring agent in products such as chewing gum, baked goods, syrups, candy, beverages, ice cream, and tobacco products; and it occurs naturally in some vegetables and berries. Methyl salicylate is of interest to the tobacco industry as oil of wintergreen is used as a flavorant in tobacco products. The purpose of this investigation was to conduct a critical review of the available literature for oral exposure to methyl salicylate, incorporating an analysis of the quality of the studies available and the current understanding of the mode of action. Following a review of all of the available literature, the most appropriate data sets for dose-response modeling were reported by Gulati et al. in which significant changes in reproductive/development endpoints were reported to occur after exposure to 500 mg/kg/d of methyl salicylate in male and female mice. Benchmark dose modeling was performed and the most sensitive endpoint, the number of litters per mating pair, was associated with a BMDL of 220 mg/kg/d. This BMDL was chosen as the point of departure and adjusted by a body weight scaling factor to derive a human equivalent dose. Based on the uncertainty factor analysis, the POD for methyl salicylate was adjusted by a UF of 3 for interspecies uncertainty to derive an allowable daily intake of 11 mg/kg/d.

Topics: Animals; Flavoring Agents; Humans; Salicylates; Toxicity Tests

As an important part of non steroids anti-inflammation drug (NSAIDs), salicylate has developed from natural substance salicylic acid to natrium salicylicum, to aspirin. Now, methyl salicylate glycoside, a new derivative of salicylic acid, is modified with a -COOH group integrated one methyl radical into formic ether, and a -OH linked with a monosaccharide, a disaccharide or a trisaccharide unit by glycosidic linkage. It has the similar pharmacological activities, anti-inflammatory, analgesic, antipyretic and antithrombotic as the previous salicylates' without resulting in serious side effects, particularly the gastrointestinal toxicity. Owing to the superiority of those significant bioactivities, methyl salicylate glycosides have became a hot research area in NSAIDs for several years. This paper compiles all 9 naturally occurring methyl salicylate glycosides, their distribution of the resource and pharmacological mechanism, which could contribute to the new drug discovery.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Biological Products; Drug Discovery; Glycosides; Humans; Salicylates

The role played by phytohormone signaling in the modulation of DNA repair gene and the resulting effects on plant adaptation to genotoxic stress are poorly investigated. Information has been gathered using the Arabidopsis ABA (abscisic acid) overly sensitive mutant abo4-1, defective in the DNA polymerase ε function that is required for DNA repair and recombination. Similarly, phytohormone-mediated regulation of the Ku genes, encoding the Ku heterodimer protein involved in DNA repair, cell cycle control and telomere homeostasis has been demonstrated, highlighting a scenario in which hormones might affect genome stability by modulating the frequency of homologous recombination, favoring plant adaptation to genotoxic stress. Within this context, the characterisation of Arabidopsis AtKu mutants allowed disclosing novel connections between DNA repair and phytohormone networks. Another intriguing aspect deals with the emerging correlation between plant defense response and the mechanisms responsible for genome stability. There is increasing evidence that systemic acquired resistance (SAR) and homologous recombination share common elements represented by proteins involved in DNA repair and chromatin remodeling. This hypothesis is supported by the finding that volatile compounds, such as methyl salicylate (MeSA) and methyl jasmonate (MeJA), participating in the plant-to-plant communication can trigger genome instability in response to genotoxic stress agents. Phytohormone-mediated control of genome stability involves also chromatin remodeling, thus expanding the range of molecular targets. The present review describes the most significant advances in this specific research field, in the attempt to provide a better comprehension of how plant hormones modulate DNA repair proteins as a function of stress.

Topics: Abscisic Acid; Acetates; Cyclopentanes; DNA Repair; Gibberellins; Models, Biological; Oxylipins; Plant Growth Regulators; Salicylates; Salicylic Acid; Signal Transduction

Efficient communication between the pest-colonised and non-colonised organs is vital for the timely manifestation of defences that restrict systemic spread of pests. The vasculature provides an important conduit for translocation of signals that contribute to long-distance communication within a plant. Airborne signals also contribute to this process. In recent years, major advances have been made in identifying metabolites that are candidate systemic signals in plant defence against pathogens. Methyl salicylate, jasmonates, azelaic acid and a diterpenoid have been implicated as mobile signals associated with the activation of systemic acquired resistance (SAR), which confers enhanced resistance against a broad spectrum of pathogens. By contrast, auxins probably contribute to negative regulation of systemic defences.

Topics: Cyclopentanes; Dicarboxylic Acids; Diterpenes; Host-Pathogen Interactions; Immunity, Innate; Oxylipins; Plants; Pseudomonas syringae; Salicylates; Signal Transduction; Xanthomonas

Serious toxicity can result from exposure to small amounts of methyl salicylate. Methyl salicylate is widely available as a component in many over-the-counter brands of creams, ointments, lotions, liniments and medicated oils intended for topical application to relieve musculoskeletal aches and pains. Among the most potent forms of methyl salicylate is oil of wintergreen (98% methyl salicylate). Other products with varying concentrations of methyl salicylate are ubiquitous throughout many parts of the world, including a number of products marketed as Asian herbal remedies. The toxic potential of all of these formulations is often underestimated by health care providers and the general public. A comprehensive review of the existing medical literature on methyl salicylate poisoning was performed, and data compiled over the past two decades by the American Association of Poison Control Centers (AAPCC) was examined. Methyl salicylate continues to be a relatively common source of pediatric exposures. Persistent reports of life-threatening and fatal toxicity were found. In children less than 6 years of age, a teaspoon (5 mL) or less of oil of wintergreen has been implicated in several well-documented deaths. More needs to be done to educate both health care providers and the general public regarding the dangers of these widely available formulations.

Topics: Child, Preschool; Fixatives; Humans; Infant; Nonprescription Drugs; Phytotherapy; Poisoning; Salicylates

A toxicologic and dermatologic review of methyl salicylate when used as a fragrance ingredient is presented.

Topics: Animals; Consumer Product Safety; Dose-Response Relationship, Drug; Humans; In Vitro Techniques; Noxae; Perfume; Risk Assessment; Salicylates; Skin; Skin Absorption; Skin Irritancy Tests; Skin Tests; Toxicity Tests

Although aspirin (acetylsalicylic acid) has become widely available without prescription, cases of self-poisoning due to overdose of salicylates are quite uncommon, with a low reported mortality. However, severe poisoning with these preparations is life threatening. Besides the aspirin, there are other sources of salicylate poisoning, such as an excessive application of topical agents, ingestion of salicylate containing ointments, use of keratolytic agents or agents containing methyl salicylate (e.g. oil of wintergreen). Most of these preparations are liquid, highly concentrated and lipid soluble, and, therefore, they are able to provoke a severe, rapid salicylate poisoning. On the basis of clinical and metabolic features or salicylate concentration in plasma it is very important to diagnose severe poisoning with salicylates in time and prescribe an adequate treatment. In the present review article various aspects of salicylate poisoning and its treatment are discussed: epidemiology, pharmacokinetics and pharmacodynamics of salicylates, clinical manifestations of their toxicity, management, enhanced elimination and prognosis.

Topics: Acute Disease; Adult; Anti-Inflammatory Agents, Non-Steroidal; Aspirin; Child; Child, Preschool; Diagnosis, Differential; Drug Interactions; Drug Overdose; Fixatives; Humans; Ointments; Poisoning; Prognosis; Pulmonary Edema; Salicylates; Time Factors

Topics: Anti-Infective Agents; Combined Modality Therapy; Cymbopogon; Debridement; Female; Foot Dermatoses; Humans; Immunocompromised Host; Keratolytic Agents; Lavandula; Mentha piperita; Nonprescription Drugs; Oils, Volatile; Ovarian Neoplasms; Plant Oils; Recurrence; Salicylates; Salicylic Acid; Treatment Outcome; Warts

Benzenoid carboxyl methyltransferases synthesize methyl esters (e.g., methyl benzoate and methyl salicylate), which are constituents of aromas and scents of many plant species and play important roles in plant communication with the surrounding environment. Within the past five years, eleven such carboxyl methyltransferases were isolated and most of them were comprehensively investigated at the biochemical, molecular and structural level. Two types of enzymes can be distinguished according to their substrate preferences: the SAMT-type enzymes isolated from Clarkia breweri, Stephanotis floribunda, Antirrhinum majus, Hoya carnosa, and Petunia hybrida, which have a higher catalytic efficiency and preference for salicylic acid, while BAMT-type enzymes from A. majus, Arabidopsis thaliana, Arabidopsis lyrata, and Nicotiana suaveolens prefer benzoic acid. The elucidation of C. breweri SAMT's three-dimensional structure allowed a detailed modelling of the active sites of the carboxyl methyltransferases and revealed that the SAM binding pocket is highly conserved among these enzymes while the methyl acceptor binding site exhibits some variability, allowing a classification into SAMT-type and BAMT-type enzymes. The analysis of expression patterns coupled with biochemical characterization showed that these carboxyl methyltransferases are involved either in floral scent biosynthesis or in plant defense responses. While the latter can be induced by biotic or abiotic stress, the genes responsible for floral scent synthesis exhibit developmental and rhythmic expression pattern. The nature of the product and efficiency of its formation in planta depend on the availability of substrates, the catalytic efficiency of the enzyme toward benzoic acid and/or salicylic acid, and the transcriptional, translational, and post-translational regulation at the enzyme level. The biochemical properties of benzenoid carboxyl methyltransferases suggest that the genes involved in plant defenses might represent the ancestor for the presently existing floral genes which during evolution gained different expression profiles and encoded enzymes with the ability to accept structurally similar substrates.

Topics: Amino Acid Sequence; Benzoates; Flowers; Gene Expression; Methyltransferases; Molecular Sequence Data; Phylogeny; Plants; Salicylates; Sequence Alignment; Sequence Homology, Amino Acid

Antimalarials, camphor, clonidine, methyl salicylates, and sulfonylureas all may result in serious poisonings and are potentially fatal in small doses in toddlers. Early recognition and appropriate management, including antidotal and supportive care, may prevent poor outcomes in these patients.

Topics: Administration, Oral; Antidotes; Antimalarials; Camphor; Child; Child, Preschool; Clonidine; Dose-Response Relationship, Drug; Humans; Poisoning; Salicylates; Sulfonylurea Compounds; United States

Methyl salicylate (oil of wintergreen) is widely available in many over-the-counter liniments, ointments, lotions or medicated oils for the relief of musculoskeletal aches and pains. Ingestion of methyl salicylate poses the threat of severe, rapid-onset salicylate poisoning because of its liquid, concentrated form and lipid solubility. Excessive usage of these preparations in patients receiving warfarin may result in adverse interactions and bleedings. Methyl salicylate in topical analgesic preparations may cause irritant or allergic contact dermatitis and anaphylactic reactions. Physicians should fully appreciate the potential dangers from topical preparations containing methyl salicylate.

Topics: Administration, Oral; Administration, Topical; Animals; Anticoagulants; Clinical Trials as Topic; Drug Hypersensitivity; Drug Interactions; Fixatives; Humans; Nonprescription Drugs; Rats; Salicylates; Skin Absorption; Warfarin

Many commonly used medications have serious toxicity in children when ingested in small doses. The toxicologic characteristics of methyl salicylate, camphor, topical imidazolines, benzocaine, and diphenoxylate-atropine are striking examples. All of these medications except Lomotil are over-the-counter and therefore, are often perceived as minimally harmful when ingested. For all of these substances, however, doses as little as 1/4 teaspoon or 1/2 tablet can have serious or fatal consequences. Thus, referral to an emergency department is prudent for ingestions involving these products. Options for initial gastrointestinal (GI) decontamination are variable, depending on the estimated amount and time of the ingestion. Induction of emesis is contraindicated for significant camphor, topical imidazoline, and Lomotil ingestions. Activated charcoal should be administered in all cases. Finally, the emergency physician must recognize the potential seriousness of these ingestions, as well as their clinical presentations to provide expeditious evaluation and treatment.

Topics: Atropine; Benzocaine; Camphor; Child; Diphenoxylate; Drug Combinations; Gastrointestinal Agents; Humans; Imidazoles; Nonprescription Drugs; Salicylates

Hot-iron branding is painful for cattle, but little is known about how long this pain lasts or effective alleviation methods. Previous work with pigs indicated that cooling burns with a gel (active ingredient: tea tree oil) improved healing compared to untreated wounds. Steers (210±21 kg) were hot-iron branded and allocated to 1 of 3 treatments: control (n=24), 1 gel application immediately after branding (1X; n=12), or 2 gel applications, 1 immediately after branding and one 1 d later (2X; n=12). Pain sensitivity was assessed by applying a known and increasing force with a von Frey anesthesiometer in 5 locations (in the center, at the top of, and 5 and 10 cm above the brand and on the equivalent location on the nonbranded side of the body) until animals showed a behavioral response. Healing was measured with a 6-point scale (1=fresh brand and 6=no scabbing and fully repigmented). Both measures, along with weight gain and surface temperature of the wound, were recorded before and 1, 2, 3, 7, 14, 21, 28, 35, 56, and 70 d after branding. The gel cooled the brand, with the most obvious differences on the day it was applied (3.7 to 4.2°C cooler than control; day×gel interaction, P=0.004). All wounds were at least partially repigmented by 70 d, but only 46% of brands were fully healed at this time. The healing process was slowed when a gel was applied twice (e.g., at 21 d, healing score of 2.5±0.1 and 2.7±0.1 vs. 2.0±0.2 for control and 1X vs. 2X, respectively; P=0.001). Brands tended to remain painful throughout the 70 d (in the center of the brand; before vs. d 1-35, P≤0.001; d 56, P=0.058; and d 70, P=0.092). Overall, gel had little effect on pain sensitivity. Weight gain was reduced on d 1 after branding compared to all other time points (P<0.001) but was not affected by gel application (P=0.277). In conclusion, applying gel did not improve outcomes after branding. In addition, by 70 d after the procedure, hot-iron brands still tended to be more painful than nonbranded tissue and 54% were not fully healed. These results raise additional animal welfare concerns about hot-iron branding.

Topics: Analgesics; Animal Husbandry; Animal Welfare; Animals; Body Temperature; Burns; Cattle; Gels; Hot Temperature; Male; Pain; Salicylates; Thermography; Time Factors; Treatment Outcome; Wound Healing

The objective of this randomized, examiner-blind, parallel, controlled clinical study was to compare the antiplaque/antigingivitis efficacy of an essential oil-containing mouthrinse (EO) to a new 0.075% cetylpyridinium chloride mouthrinse (CPC) using a two-week experimental gingivitis model with a 5% hydroalcohol rinse serving as the negative control.. After signing informed consents and completing baseline examinations, 185 subjects were randomized into three groups. Subjects began supervised/recorded rinsing with 20 ml of their assigned rinse for 30 seconds twice daily for two weeks, with no mechanical oral hygiene permitted. Baseline and two-week assessments were conducted as follows: Turesky Modification of the Quigley-Hein Plaque Index (PI), Modified Gingival Index (MGI), and the Gingival Bleeding Index (BI). Analysis of efficacy variables (i.e., mean PI, mean MGI, mean BI, and proportion of bleeding sites derived from the BI) was performed using a one-way analysis of covariance (ANCOVA).. Among the 182 subjects who completed the study, the EO rinse showed statistically significant reductions compared to the negative control within the range previously reported in this model; PI = 36.5% (p < 0.001) and MGI = 17.5% (p < 0.001). A 43.2% reduction in proportion of bleeding sites (p < 0.001) was demonstrated. Mean PI, MGI, and proportion of bleeding sites at two weeks were statistically significantly lower for the EO rinse compared to the CPC rinse (p < 0.001), showing 27.7%, 11.9%, and 30.0% reductions, respectively.. An EO rinse provided superior antigingivitis/antiplaque efficacy compared to a 0.075% CPC rinse in this short-term clinical trial, and demonstrated efficacy within the range shown in previous studies using this model.

Topics: Adolescent; Adult; Aged; Analysis of Variance; Anti-Infective Agents, Local; Cetylpyridinium; Cyclohexanols; Dental Plaque; Dental Plaque Index; Drug Combinations; Eucalyptol; Female; Gingivitis; Humans; Male; Menthol; Middle Aged; Monoterpenes; Mouthwashes; Oils, Volatile; Periodontal Index; Salicylates; Single-Blind Method; Terpenes; Thymol; Young Adult

This study was designed to compare the efficacy of double-modality therapy, phonophoresis and cryotherapy in the management of pain among subjects who suffered from musculoskeletal injuries (MSIs).Sixty (60) subjects were assigned randomly to one of three groups: DMT group (n=20) received cryotherapy and 15% methyl salicylate phonophoresis, PHONO group (n=20) received 15% methyl salicylate phonophoresis and CRYO group (n=20) received cryotherapy and "sham‟ phonophoresis. Ultrasound at an intensity of 1.5 W/cm² and frequency of 1MHz was used to apply methyl salicylate while intermittent cryotherapy was the mode of application. Subjects‟ pre- and post-treatment pain perception scores (PPS) using visual analogue scale (VAS) were assessed and the sessions of treatment in all groups were recorded. Treatment was administered on alternate days and discharges were made in all groups when subjects were pain free. A total of 275 treatment sessions was recorded - 72 (26.2%) in DMT, 105 (38.2%) in PHONO and 98 (35.6%) in CRYO group respectively which indicated no significant difference (P>0.05). Nineteen (19), thirteen (13) and twelve (12) subjects were pain free in DMT, CRYO or PHONO groups respectively after 1 to 5 treatments. The difference in the severity of pain was significant (P<0.05) in each group post-treatment which suggests that DMT, phonophoresis and cryotherapy were equally effective. The study has demonstrated therapeutic efficacy of DMT, but it was not superior to the single treatment protocol of phonophoresis or cryotherapy. However, it might take fewer sessions in the DMT group to treat and make more than 90% of the subjects pain free and fit to return to active performance.

Topics: Adolescent; Adult; Aged; Anti-Inflammatory Agents, Non-Steroidal; Combined Modality Therapy; Cryotherapy; Female; Humans; Male; Middle Aged; Musculoskeletal Pain; Nigeria; Pain Management; Pain Measurement; Pain Perception; Phonophoresis; Salicylates; Time Factors; Treatment Outcome; Young Adult

Current treatment strategies for painful diabetic neuropathy (PDN) include oral medications, which are costly and may have adverse effects. Topical therapies have been used for PDN with some benefit. Nutmeg has certain properties that may be effective in ameliorating neuropathic pain. The purpose of this study was to determine whether topical nutmeg extracts can reduce pain or improve the quality of life in PDN sufferers.. This study was a randomized, double-blind, placebo-controlled trial.. It was conducted at a primary care center in Trinidad, Caribbean.. Seventy-four (74) diabetic subjects who met criteria for painful neuropathy were recruited.. Participants were randomized to receive either topical nutmeg extracts (NEMM; mace oil [2%], nutmeg oil [14%], methyl salicylate [6%], menthol [6%], and coconut oil) or placebo (MM; methyl salicylate [6%], menthol [6%], coconut oil, and alcohol).. Outcome measures of pain and quality of life were assessed using the Brief Pain Inventory for Diabetic Painful Neuropathy and Neuropathic Pain Symptom Inventory.. An intention-to-treat analysis was done for 24 male and 50 female subjects (30-85 years) with an average duration of diabetes of 11 years. Significant reductions in worst and average pain scores were seen within each group (p ≤ 0.001). Similarly significant reductions were also noted for interference with walking, sleep, and mood scores as well as burning, pins and needles, and tingling scores within each group (p<0.05). There were no statistically significant differences between both groups after 4 weeks for any outcome measure.. In this trial topical, nutmeg extracts did not add to the improvements observed in PDN symptoms during 4 weeks treatment with preparations containing menthol and methyl salicylate. Further research designed to test the individual components of the topical therapies used in this study may clarify their benefit.

Topics: Administration, Topical; Adult; Aged; Aged, 80 and over; Analgesics; Diabetic Neuropathies; Double-Blind Method; Female; Humans; Intention to Treat Analysis; Male; Menthol; Middle Aged; Myristica; Neuralgia; Oils, Volatile; Plant Oils; Salicylates

To evaluate the clinical efficacy of subgingival ultrasonic instrumentation irrigated with essential oils (EOs) of residual periodontal pockets.. Sixty-four individuals with chronic periodontitis were invited to participate in this randomized, double-blind, parallel, and placebo-controlled clinical trial. All subjects received non-surgical periodontal therapy. After re-evaluation (baseline), residual pockets (pocket depth ≥5 mm) received test (ultrasonic instrumentation irrigated with EOs) or control therapy (ultrasonic instrumentation irrigated with negative control). Probing pocket depth (PPD), gingival recession (R), clinical attachment level (CAL), bleeding on probing (BOP), and plaque were assessed at baseline and after 4, 12, and 24 weeks. Differences between groups and changes over the course of time were analysed according to a generalized linear model.. There was a significant reduction in PPD and BOP, as well as a significant CAL gain in the two groups (p<0.001). Nevertheless, there were no differences between the groups at any time of the study. When only initially deep pockets (PPD ≥7 mm) were analysed, a significantly greater CAL gain (p=0.03) and PPD reduction (p=0.01) was observed in the test group.. The adjunctive use of EOs may promote significant CAL gain and PPD reduction in deep residual pockets.

Topics: Adult; Anti-Infective Agents, Local; Chronic Periodontitis; Cyclohexanols; Dental Plaque; Double-Blind Method; Drug Combinations; Ethanol; Eucalyptol; Eucalyptus; Female; Follow-Up Studies; Gingival Hemorrhage; Gingival Recession; Humans; Male; Menthol; Middle Aged; Monoterpenes; Oils, Volatile; Periodontal Attachment Loss; Periodontal Pocket; Placebos; Salicylates; Subgingival Curettage; Terpenes; Therapeutic Irrigation; Thymol; Treatment Outcome; Ultrasonic Therapy

An occlusive patch formulation containing 10% methyl salicylate and 3% l-menthol was recently approved by the US Food and Drug Administration for the treatment of mild to moderate pain. Despite widespread use of counterirritants, including methyl salicylate and menthol, for topical pain relief, published efficacy and safety data regarding the use of the agents alone or in combination are limited.. The goal of this study was to determine the efficacy and safety profile of a patch containing 10% methyl salicylate and 3% l-menthol compared with a placebo patch in adult patients with mild to moderate muscle strain.. Eligible patients were men or women aged >or=18 years with a clinical diagnosis of mild to moderate muscle strain. Patients were randomly assigned to receive either 1 active patch or 1 placebo patch applied to the skin at the affected area (ie, shoulder, upper back, upper arm, neck, calf, thigh, forearm, abdomen). Pain intensity was assessed on a 100-mm visual analog scale while at rest and with movement for 12 hours after patch application. The primary efficacy end point was the summed pain intensity difference score through 8 hours (SPID8) with movement. Analyses included use of descriptive statistics and an ANOVA model. Safety data, including adverse events, and secondary efficacy end points were also evaluated.. A total of 208 patients (104 men, 104 women; age range, 18-78 years) were randomized to 1 of 2 study groups (105 in the active-patch group [mean age, 37.3 years], 103 in the placebo-patch group [mean age, 38.1 years]). The primary efficacy analysis (SPID8 with movement) indicated that patients receiving the active patch experienced significantly greater pain relief (approximately 40%) than those patients receiving a placebo patch (mean [SD], 182.6 [131.2] vs 130.1 [144.1]; P = 0.005). Analysis of the per-protocol population also found significantly more relief (P = 0.024) in the active-patch group (176.2 [131.4]; n = 92) versus the placebo-patch group (130.2 [144.0]; n = 96). Statistical analysis of secondary efficacy measures supported the primary end-point results. The number of patients experiencing any type of adverse event was comparable between study groups (active patch, 6.7% [7 events]; placebo patch, 5.8% [6 events]). No serious adverse events were reported during the study.. A single, 8-hour application of a patch containing methyl salicylate and l-menthol provided significant relief of pain associated with mild to moderate muscle strain in these adult patients compared with patients receiving a placebo patch.

Topics: Administration, Cutaneous; Adolescent; Adult; Aged; Antipruritics; Antirheumatic Agents; Double-Blind Method; Female; Humans; Male; Menthol; Middle Aged; Muscle, Skeletal; Pain Measurement; Placebos; Salicylates; Severity of Illness Index; Sprains and Strains; Treatment Outcome; Young Adult

Oral acetylsalicylic acid (aspirin) is the primary antiplatelet therapy in the treatment of acute myocardial infarction and acute coronary syndrome. Methyl salicylate (MS; oil of wintergreen) is compounded into many over-the-counter antiinflammatory muscle preparations and has been shown to inhibit platelet aggregation locally and to be absorbed systemically.. To assess the ability of topically applied MS to inhibit systemic platelet aggregation for patients who are unable to tolerate oral drug therapy.. A randomized, prospective, blinded, crossover study was conducted in 9 healthy men, aged 30-46 years. All subjects ingested 162 mg of aspirin or applied 5 g of 30% MS preparation to their anterior thighs. There was a minimum 2-week washout period between study arms. Blood and urine were collected at baseline and at 6 hours. An aggregometer measured platelet aggregation over time against 5 standard concentrations of epinephrine, and a mean area under the curve (AUC) was calculated. Urinary metabolites of thromboxane B(2) were measured by a standard enzyme immunoassay. Differences in and between groups at baseline and 6 hours were tested by the Wilcoxon signed-rank test.. Baseline platelet aggregation did not differ significantly between the 2 arms of the study (median AUC [% aggregation(*)min]; binominal confidence intervals): aspirin 183; 139 to 292 versus MS 197; 118 to 445 (p = 0.51). Both aspirin and MS produced statistically significant platelet inhibition; aspirin decreased the AUC from 183; 139 to 292 to 85; 48 to 128 (p = 0.008) and MS decreased the AUC from 197; 118 to 445 to 112; 88 to 306 (p = 0.011). No significant difference was detected between baseline and 6-hour thromboxane levels for either aspirin (p = 0.779) or MS (p = 0.327).. Topical MS and oral aspirin both significantly decrease platelet aggregation in healthy human volunteers.

Topics: Administration, Cutaneous; Administration, Oral; Adult; Area Under Curve; Aspirin; Cross-Over Studies; Double-Blind Method; Epinephrine; Humans; Immunoenzyme Techniques; Male; Middle Aged; Platelet Aggregation; Platelet Aggregation Inhibitors; Prospective Studies; Salicylates; Statistics, Nonparametric; Thromboxane B2; Time Factors

Our objective was to determine whether the degree of variability associated with dermal microdialysis allows its practical application to determinations of bioequivalence of topically applied agents with a reasonable number of subjects. A statistical review of literature data was conducted to estimate the variances associated with subject-to-subject variability and the probe-to-probe variability within the subjects. In order to successfully utilise dermal microdialysis to establish bioequivalence of topically applied agents, particular care must be applied to study design. Due to the inherent variability between subjects, to maintain subject numbers at reasonable levels, each subject should act as their own control, thus removing the element of subject-to-subject variability from calculations of sample sizes. It is also recommended that measurements are made in duplicate in each subject to reduce the element of variability further. It is then possible to demonstrate, within 80-125% confidence limits and a subject population of approximately 20, that two formulations are bioequivalent.

Topics: Administration, Cutaneous; Adult; Area Under Curve; Female; Humans; Male; Microdialysis; Reproducibility of Results; Salicylates; Sample Size; Skin Absorption; Therapeutic Equivalency

This randomized, double-blind study was designed to evaluate the effectiveness of the topical cream Theraflex-TMJ (NaBob/Rx, San Mateo, CA) in patients with masseter muscle pain and temporomandibular joint (TMJ) pain. Fifty-two subjects (5 males and 47 females) were instructed to apply a cream over the afflicted masseter muscle(s) or over the jaw joint(s) twice daily for two weeks. Theraflex-TMJ cream was used by the experimental group, while a placebo cream was used by the control group. The means of pain ratings were calculated prior to the application of the cream (baseline), after ten days of tx (period 1), and 15 days of tx (period 2) days of treatment and five days after stopping the treatment (follow-up). There was a significant decrease in reported pain levels from baseline in the experimental group for period 1 (p < 0.01), period 2 (p < 0.001), and follow-up (p < 0.01). For the control group, no significant differences were found between the different time periods (p > 0.05). There was evidence of minor side effects such as skin irritation and/or burning on the site of the application in two subjects in the experimental as well as two subjects in the control groups. The data strongly suggest that Theraflex-TMJ topical cream is safe and effective for reducing pain in the masseter muscle and the temporomandibular joint.

Topics: Adult; Analysis of Variance; Anti-Inflammatory Agents, Non-Steroidal; Carboxylic Acids; Copper; Dipeptides; Double-Blind Method; Facial Pain; Female; Follow-Up Studies; Humans; Male; Masseter Muscle; Nonprescription Drugs; Pain Measurement; Salicylates; Temporomandibular Joint Disorders; Zinc

Camphor, menthol, and methyl salicylate occur in numerous over-the-counter products. Although extensively used, there have been no estimates of human exposure following administration via dermal application. Furthermore, there is little information about the pharmacokinetics of those compounds. The authors report the plasma concentrations of the intact compounds as a function of dose following dermal patch application. Three groups of 8 subjects (4 male, 4 female) applied a different number of commercial patches (2, 4, or 8) to the skin for 8 hours. Plasma samples were assayed using sensitive and selective gas-chromatographic methods. For the 8-patch group, the average maximum plasma concentrations (Cmax +/- SD) were 41.0 +/- 5.8 ng/mL, 31.9 +/- 8.8 ng/mL, and 29.5 +/- 10.5 ng/mL for camphor, menthol, and methyl salicylate, respectively. The corresponding values for the 4-patch group were 26.8 +/- 7.2 ng/mL, 19.0 +/- 5.4 ng/mL, and 16.8 +/- 6.8 ng/mL. The harmonic mean terminal half-lives were 5.6 +/- 1.3 hours, 4.7 +/- 1.6 hours, and 3.0 +/- 1.2 hours for camphor, menthol, and methyl salicylate, respectively. The 2-patch group had measurable but low plasma concentrations of each compound. Low-dose dermal application for an extended time results in low plasma concentrations of all 3 compounds. Four and 8 patches, when applied for 8 hours, gave measurable and nearly proportional plasma concentrations. Although unable to determine the absolute dermal bioavailability of these compounds, there appears to be relatively low systemic exposure to these potentially toxic compounds, even when an unrealistically large number of patches are applied for an unusually long time.

Topics: Administration, Topical; Adolescent; Adult; Camphor; Female; Humans; Linear Models; Male; Menthol; Middle Aged; Salicylates; Skin Absorption

Poison Control Centers follow the acetylsalicylic acid (ASA) treatment guideline to manage unintentional ingestions of topical methyl salicylate liniments. For example, one teaspoon of 30% methyl salicylate cream such as Ben Gay provides an "ASA equivalent dose" of 180 mg/kg for a 10 kg child. The ASA treatment guideline advises emesis with syrup of Ipecac and 24 h home followup for this dose. Both the ASA conversion factor to yield the ASA equivalent dose and the treatment guideline assume 100% bioavailability of the salicylate. The nature of this topical dosage product led the investigators to expect less than complete absorption of methyl salicylate.. To compare plasma concentrations of salicylate from ingested methyl salicylate cream with plasma concentrations of salicylate from ingested oil of wintergreen.. Four adult volunteers consented to an open label, four-way crossover design, with randomization to the following treatments: 1 mL Oil of Wintergreen, U.S.P., 6.7 g of Ben Gay 15% and 20 g of Ben Gay 15% and also to hold 5 g of Ben Gay 15% cream in the buccal cavity for 1 minute and then expectorate. Plasma was collected for salicylate determination, and the results analyzed with a noncompartmental pharmacokinetic model.. No plasma salicylate was detected after buccal treatment phase. Relative bioavailability for the low-dose treatment was 0.5 compared to oil of wintergreen.. Plasma salicylate concentrations from methyl salicylate cream are not equal to those achieved after ingestion of oil of wintergreen. Dosage formulation must be considered when predicting toxicity.

Topics: Absorption; Adult; Area Under Curve; Biological Availability; Child, Preschool; Cross-Over Studies; Female; Humans; Male; Salicylates

To determine the effect of 6 months use of an essential oil-containing (EO) antiplaque/antigingivitis fluoride dentifrice on the balance of the oral microbial flora and on the emergence of resistant microbial forms by analysis of dental plaque and saliva.. The dentifrice essential oils consisted of a fixed combination of thymol, menthol, methyl salicylate, and eucalyptol. An identical fluoride-containing dentifrice without the essential oils served as the control. A subgroup of 66 subjects from a clinical trial population of 321 was randomly selected for characterization of their dental plaque microflora. Saliva was also cultured to monitor for the emergence of opportunistic pathogens. Supragingival plaque and saliva were harvested at baseline, after which subjects received a dental prophylaxis. Subjects were sampled again after 3 and 6 months of product use prior to clinical examination. Plaque was characterized for microbial content by phase contrast microscopy for recognizable cellular morphotypes and by cultivation on nonselective and selective culture media. Determination of the minimum inhibitory concentrations of the test agent against selected Actinomyces and Veillonella isolated bacterial species was conducted at all time points to monitor for the potential development of bacterial resistance.. There were no statistically significant differences between the microbial flora obtained from subjects using the essential oil-containing dentifrice and the vehicle control for all parameters and time periods except for the percentage of spirochetes at 6 months and for percentage of "other" microorganisms at 3 months. The EO group exhibited a lower adjusted mean for both parameters. Additionally, there was no evidence of the development of bacterial resistance to the antimicrobial activity of the essential oils or the emergence of opportunistic pathogens.

Topics: Actinomyces; Adolescent; Adult; Anti-Infective Agents, Local; Bacteria; Cariostatic Agents; Colony Count, Microbial; Culture Media; Cyclohexanols; Dental Plaque; Dentifrices; Double-Blind Method; Drug Resistance, Bacterial; Eucalyptol; Eucalyptus; Female; Fluorides; Follow-Up Studies; Gingivitis; Humans; Male; Menthol; Microscopy, Phase-Contrast; Middle Aged; Monoterpenes; Oils, Volatile; Salicylates; Saliva; Spirochaetales; Terpenes; Thymol; Veillonella

To compare the rate and extent of systemic salicylate absorption following single and multiple applications of two topically applied analgesics, one containing methyl salicylate and the other containing trolamine salicylate.. Two-period, two-treatment, randomized, crossover, multiple-dose study in healthy men and women volunteers.. Six men and six women volunteers, 21-44 years of age.. Subjects applied 5 g of an ointment containing 12.5% methyl salicylate twice daily for 4 days (8 doses) or a cream containing trolamine 10% twice daily for two doses, to a 10-cm2 area on the thigh. Treatment order and leg (right or left) were assigned randomly. Subjects were crossed over to the alternate treatment on the other leg after a minimum washout period of 7 days.. The total amount of salicylate recovered in the urine during two dosing intervals (24 hours) on each study day, relative to the applied dose, was used to calculate the bioavailability of each product. Mean standard pharmacokinetic parameters including area under the curve, maximum concentration (Cmax), time to maximum concentration, and minimum concentrations at steady-state were determined from serum concentrations. Serum concentrations were fit to three pharmacokinetic models and the suitability of each model was evaluated. Estimates of absorption rate constant, clearance, volume, and fraction absorbed on day 1 were estimated by using the best-fitting model.. Salicylic acid could not be detected in serum after trolamine application. However, concentrations between 0.31 and 0.91 mg/L were detected within 1 hour of the first application of methyl salicylate and Cmax between 2 and 6 mg/L were observed following the seventh application on day 4. Both the extent and rate of absorption changed after the first 24 hours. The absorption rate constant increased significantly from the first to the seventh dose (first dose absorption rate constant: 0.16 h-1, seventh dose: 0.28 h-1; p < 0.035). Urinary recovery of total salicylate (salicylic acid and principal metabolites of salicylic acid) during the first 24 hours of the methyl salicylate phase averaged 175.2 mg, exceeding the 6.9 mg (p < 0.05) recovered during the trolamine phase. The recovery of salicylate in the urine in the first 24 hours after application of methyl salicylate was significantly greater than the 1.4% recovered after application of trolamine (p < 0.05). Furthermore, the fraction of methyl salicylate recovered in the urine increased significantly from 15.5% on day 1 to approximately 22% on the second, third, and fourth days.. A considerable amount of salicylic acid may be absorbed through the skin after topical application of methyl salicylate products and this may increase with multiple applications. Caution is warranted in patients for whom systemic salicylate may be hazardous or problematic.

Topics: Administration, Cutaneous; Adult; Analysis of Variance; Anti-Inflammatory Agents, Non-Steroidal; Cross-Over Studies; Dosage Forms; Female; Humans; Male; Ointments; Salicylates; Skin Absorption

A previous clinical screening study demonstrated that a cetylpyridinium chloride (CPC) essential oil mouthrinse inhibited plaque regrowth to a significantly greater extent than a negative control or a triclosan/copolymer rinse when used without toothbrushing. The purpose of this study was to evaluate the same ingredient combination as a pre-brushing rinse over a 6-week period. The study employed a 4 group parallel design with a minimum of 50 subjects per group. Subjects with a minimum baseline plaque index of 1.95 were recruited. The formulations employed were two variations of a CPC/essential oil rinse, a triclosan/copolymer product, and a hydroalcohol negative control. Subjects were rendered plaque free at baseline and then rinsed twice daily before toothbrushing with their allocated product. Plaque was scored at 6 days and 6 weeks. Plaque scores were reduced at 6 days compared to baseline but there were no significant differences between any of the groups. At 6 weeks, plaque scores were significantly lower in both CPC/essential oil groups compared to control. Although both CPC/essential oil groups showed plaque scores which were lower than the triclosan group, in only one of the groups was the difference significant. The triclosan product was not significantly different from control. The results support the previous findings that a CPC/essential oil rinse could be a useful adjunct to oral hygiene when used prior to normal toothbrushing.

Topics: Adolescent; Adult; Aged; Alcohols; Analysis of Variance; Cetylpyridinium; Cyclohexanols; Dental Plaque; Dental Plaque Index; Double-Blind Method; Drug Combinations; Eucalyptol; Female; Humans; Male; Menthol; Middle Aged; Monoterpenes; Mouthwashes; Oils, Volatile; Oral Hygiene; Salicylates; Terpenes; Thymol; Toothbrushing; Triclosan

Immunohistochemical investigation of archival histological material is a serious problem, since long-term storage of biological tissues, most often in formalin, leads to a loss of antigenic properties. However, the biological material can also be stored in the clearing agent methyl salicylate. The aim of this study was to assess the antigenicity of the human choroid plexus after extra long-term storage in methyl salicylate.. The study was performed on samples of fixed human choroid plexus (occasionally with attached neighboring pineal gland) stored in either methyl salicylate or paraffin blocks for 25 years. Chromogenic and fluorescence immunohistochemistry of vimentin, GFAP, type IV collagen, β-catenin, α-smooth muscle actin, von Willebrand factor, CD68, mast cell tryptase, TMEM119, and synaptophysin was carried out.. The storage of human choroid plexus in methyl salicylate for 25 years does not impair its histomorphology and preserves the properties of all the antigens assessed, which makes their immunohistochemical visualization possible using both light and fluorescence microscopy. Additionally, we found that long-term storage of human choroid plexus in methyl salicylate does not cause an increase in autofluorescence.. Methyl salicylate can be recommended as a medium for long-term storage of biological tissue, as it provides excellent brain tissue preservation and retains its antigenic properties for up to 25 years.

Topics: Choroid Plexus; Formaldehyde; Humans; Immunohistochemistry; Salicylates

Aphids have been mainly controlled by traditional chemical insecticides, resulting in unamiable risk to the environment over the last decades. Push-pull strategy is regarded as a promising eco-friendly approach for aphid management through repelling aphid away and attracting their natural enemy. Methyl salicylate (MeSA), one of typical HIPVs (herbivore-induced plant volatiles), can repel aphids and attract ladybugs. Our previous studies discovered a new lead compound 3e, a salicylate-substituted carboxyl (E)-β-farnesene derivative that had effective aphid-repellent activity. However, whether 3e has attractive activity to ladybug like MeSA is unknown. Meanwhile, to discover a new derivative for both deterring aphid and recruiting ladybug is meaningful for green control of aphids.. Through the structural optimization of 3e, 14 new derivatives were designed and synthesized. Among them, compounds 4e and 4i had good aphid (Acyrthosiphon pisum) repellent activity, and compounds 3e, 4e and 4i had significant ladybug (Harmonia axyridis) attractive activity to males. Particularly, 4i exhibited manifest attractive effect on the females as well. Binding mechanism showed that 4i not only bound effectively with the aphid (Acyrthosiphon pisum) target ApisOBP9 thanks to its multiple hydrophobic interactions and hydrogen-bond, but also had strong binding affinity with ladybug target HaxyOBP15 due to the suitable steric space. Additionally, 4i displayed low toxicity to bee Apis mellifera.. Compound 3e does exhibit attractive activity to male ladybug as MeSA. However, the new derivative 4i, with both pleasant aphid-repellent and ladybug-attraction activities, can be considered as a novel potential push-pull candidate for aphid control in sustainable agriculture. © 2022 Society of Chemical Industry.

Topics: Acyclic Monoterpenes; Animals; Aphids; Bees; Coleoptera; Insect Repellents; Salicylates

Methyl salicylate is an important inter- and intra-plant signaling molecule, but is deemed undesirable by humans when it accumulates to high levels in ripe fruits. Balancing the tradeoff between consumer satisfaction and overall plant health is challenging as the mechanisms regulating volatile levels have not yet been fully elucidated. In this study, we investigated the accumulation of methyl salicylate in ripe fruits of tomatoes that belong to the red-fruited clade. We determine the genetic diversity and the interaction of four known loci controlling methyl salicylate levels in ripe fruits. In addition to Non-Smoky Glucosyl Transferase 1 (NSGT1), we uncovered extensive genome structural variation (SV) at the Methylesterase (MES) locus. This locus contains four tandemly duplicated Methylesterase genes and genome sequence investigations at the locus identified nine distinct haplotypes. Based on gene expression and results from biparental crosses, functional and non-functional haplotypes for MES were identified. The combination of the non-functional MES haplotype 2 and the non-functional NSGT1 haplotype IV or V in a GWAS panel showed high methyl salicylate levels in ripe fruits, particularly in accessions from Ecuador, demonstrating a strong interaction between these two loci and suggesting an ecological advantage. The genetic variation at the other two known loci, Salicylic Acid Methyl Transferase 1 (SAMT1) and tomato UDP Glycosyl Transferase 5 (SlUGT5), did not explain volatile variation in the red-fruited tomato germplasm, suggesting a minor role in methyl salicylate production in red-fruited tomato. Lastly, we found that most heirloom and modern tomato accessions carried a functional MES and a non-functional NSGT1 haplotype, ensuring acceptable levels of methyl salicylate in fruits. Yet, future selection of the functional NSGT1 allele could potentially improve flavor in the modern germplasm.

Topics: Ecuador; Fruit; Glycosyltransferases; Humans; Salicylates; Solanum lycopersicum

Citrus production is severely threatened by the devastating Huanglongbing (HLB) disease globally. By studying and analyzing the defensive behaviors of an HLB-tolerant citrus cultivar 'Shatangju', we discovered that citrus can sense Candidatus Liberibacter asiaticus (CLas) infection and induce immune responses against HLB, which can be further strengthened by both endogenously produced and exogenously applied methyl salicylate (MeSA). This immune circuit is turned on by an miR2977-SAMT (encoding a citrus Salicylate [SA] O-methyltransferase) cascade, by which CLas infection leads to more in planta MeSA production and aerial emission. We provided both transgenic and multi-year trail evidences that MeSA is an effective community immune signal. Ambient MeSA accumulation and foliage application can effectively induce defense gene expression and significantly boost citrus performance. We also found that miRNAs are battle fields between citrus and CLas, and about 30% of the differential gene expression upon CLas infection are regulated by miRNAs. Furthermore, CLas hijacks host key processes by manipulating key citrus miRNAs, and citrus employs miRNAs that coordinately regulate defense-related genes. Based on our results, we proposed that miRNAs and associated components are key targets for engineering or breeding resistant citrus varieties. We anticipate that MeSA-based management, either induced expression or external application, would be a promising tool for HLB control.

Topics: Citrus; Liberibacter; MicroRNAs; Plant Breeding; Plant Diseases; Rhizobiaceae; Salicylates

Hydrocarbons with sufficient water solubility allosterically modulate anesthetic-sensitive ion channels. Mint extracts L-carvone and methyl salicylate water solubility exceeds modulation cutoff values for γ-amino butyric acid type A (GABAA) receptors, N-methyl-D-aspartate (NMDA) receptors, and type-2 voltage-gated sodium (Nav1.2) channels. We hypothesized that mint extracts modulate these channels at concentrations that anesthetize rats.. Channels were expressed separately in frog oocytes and studied using 2-electrode voltage clamp techniques at drug concentrations up to 10 mM. Normalized current effects were fit to Hill equations. Mint compounds were formulated in a lipid emulsion and administered IV to rats. When unresponsive to the tail clamp, rats were exsanguinated, and plasma drug concentrations were measured.. Both mint compounds caused concentration-dependent inhibition of all channels except for methyl salicylate which inhibited GABAA receptors at low concentrations and potentiated at high concentrations. Plasma drug concentrations in anesthetized rats were 7.9 mM for L-carvone and 2.7 mM for methyl salicylate. This corresponded to ≥53% NMDA receptor inhibition and ≥78% Nav1.2 channel inhibition by both compounds and 30% potentiation of GABAA receptors by methyl salicylate.. L-Carvone and methyl salicylate allosterically modulate cell receptor targets important to molecular actions of conventional anesthetics at concentrations that also induce general anesthesia in rats.

Topics: Anesthetics; Animals; Cyclohexane Monoterpenes; Mentha; Oocytes; Plant Extracts; Rats; Receptors, GABA-A; Receptors, N-Methyl-D-Aspartate; Salicylates; Xenopus laevis

The carotenoid biosynthesis and phenolic metabolism were studied to explain the effect of methyl salicylate (MeSA) on the lipophilic antioxidant capacity (LAC) and hydrophilic antioxidant capacity (HAC) in apricot during postharvest storage. Our results indicated that the HAC of apricot was higher than LAC and mainly responsible for total antioxidant capacity of apricot. Preharvest spraying of MeSA (0.2 mmol L

Topics: Antioxidants; Carotenoids; Phenols; Prunus armeniaca; Salicylates

Supramolecular complexes or polymers, formed by noncovalent intermolecular forces such as π-π and dipole-dipole interactions, have the potential to render collective optical properties brought about by excitons spreading over multiple molecules, as seen in J-aggregates. In this respect, molecules with a large π-system and dipole moment are advantageous. However, we report here that methyl salicyate (MS) dyad-type molecules, synthesized by connection of two MSs via a σ-bridge, are effective for forming stable aggregates with collective optical properties. The self-association of MS-dyads occurs in a CHCl

Topics: Fluorescence; Polymers; Salicylates

A series of small organic molecules having a bis-amide backbone containing hydrogen-bond functionalities were rationally designed, synthesized and characterized to examine their ability to act as potential low-molecular-weight gelators (LMWGs). All the bis-amides were decorated with identical 3-pyridyl amide of L-phenylalanine moieties along with variously substituted terminal benzoyl groups. Gelation studies revealed that only 4-methylphenyl substituted bis-amide (PME) was capable of gelling both aqueous (DMSO/water) and methyl salicylate (MS) (an important solvent for topical formulation for medical applications) solvents; whereas 4-chlorophenyl and 4-bromophenyl substituted bis-amides (PCL, PBR, respectively) acted as organogelator for various organic solvents. On the contrary, 4-nitrophenyl as well as 3,5-dinitrophenyl substituted bis-amides (PNI, DNI, respectively) were unable to gel any solvents studied herein. The corresponding aqueous gel namely PME-HG and three methyl salicylate gels PME-MS, PCL-MS and PBR-MS were characterized by dynamic and table top rheology followed by electron microscopy. Single crystal X-ray diffraction (SXRD) data revealed crucial insights into the supramolecular assembly of all the gelator and nongelator bis-amides. Both PME-HG and PME-MS were rheoreversible - an important property in material applications. Interestingly, PME-MS displayed remarkable material properties such as shape-sustaining, loadbearing and self-healing. Selected MS and aqueous gels loaded with nano-molar iodine were found to possess anti-bacterial property as revealed by zone inhibition assay.

Topics: Amides; Dimethyl Sulfoxide; Gels; Hydrogen; Iodine; Phenylalanine; Salicylates; Solvents; Water

Red wines produced without the addition of any SO

Topics: Gas Chromatography-Mass Spectrometry; Odorants; Salicylates; Sulfites; Volatile Organic Compounds; Wine

A facile and effective tandem reaction of ynones and methyl salicylates was developed to obtain a broad range of 3-acyl chromones in moderate-to-excellent yields. This protocol underwent a Michael addition and cyclization process, which exhibited easily accessible substrates, broad substrate scope, and high regioselectivity under mild and transition-metal-free conditions. Moreover, gram-scale reaction and further chemical transformation of the products were also further studied.

Topics: Chromones; Cyclization; Salicylates; Stereoisomerism; Transition Elements

In plants, basic leucine zipper transcription factors (TFs) play important roles in multiple biological processes such as anthesis, fruit growth & development and stress responses. However, systematic investigation and characterization of bZIP-TFs remain unclear in Chinese white pear. Chinese white pear is a fruit crop that has important nutritional and medicinal values.. In this study, 62 bZIP genes were comprehensively identified from Chinese Pear, and 54 genes were distributed among 17 chromosomes. Frequent whole-genome duplication (WGD) and dispersed duplication (DSD) were the major driving forces underlying the bZIP gene family in Chinese white pear. bZIP-TFs are classified into 13 subfamilies according to the phylogenetic tree. Subsequently, purifying selection plays an important role in the evolution process of PbbZIPs. Synteny analysis of bZIP genes revealed that 196 orthologous gene pairs were identified between Pyrus bretschneideri, Fragaria vesca, Prunus mume, and Prunus persica. Moreover, cis-elements that respond to various stresses and hormones were found on the promoter regions of PbbZIP, which were induced by stimuli. Gene structure (intron/exon) and different compositions of motifs revealed that functional divergence among subfamilies. Expression pattern of PbbZIP genes differential expressed under hormonal treatment abscisic acid, salicylic acid, and methyl jasmonate  in pear fruits by real-time qRT-PCR.. Collectively, a systematic analysis of gene structure, motif composition, subcellular localization, synteny analysis, and calculation of synonymous (Ks) and non-synonymous (Ka) was performed in Chinese white pear. Sixty-two bZIP-TFs in Chinese pear were identified, and their expression profiles were comprehensively analyzed under ABA, SA, and MeJa hormones, which respond to multiple abiotic stresses and fruit growth and development. PbbZIP gene occurred through Whole-genome duplication and dispersed duplication events. These results provide a basic framework for further elucidating the biological function characterizations under multiple developmental stages and abiotic stress responses.

Topics: Abscisic Acid; Basic-Leucine Zipper Transcription Factors; Chromosomes, Plant; Exons; Fragaria; Fruit; Gene Duplication; Gene Expression Regulation, Plant; Genome-Wide Association Study; Genome, Plant; Introns; Multigene Family; Phylogeny; Plant Proteins; Pyrus; Salicylates; Salicylic Acid; Stress, Physiological; Synteny

The pea leafminer, Liriomyza huidobrensis, is an important pest species affecting ornamental crops worldwide. Plant damage consists of oviposition and feeding punctures created by female adult flies as well as larva-bored mines in leaf mesophyll tissues. How plants indirectly defend themselves from these two types of leafminer damage has not been sufficiently investigated. In this study, we compared the indirect defense responses of bean plants infested by either female adults or larvae. Puncturing of leaves by adults released green leaf volatiles and terpenoids, while larval feeding caused plants to additionally emit methyl salicylate and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT). Puncturing of plants by female adults induced increases in jasmonic acid (JA) and JA-related gene expressions but reduced the expressions of salicylic acid (SA)-related genes. In contrast, JA and SA and their-related gene expression levels were increased significantly by larval feeding. The exogenous application of JA+SA significantly triggered TMTT emission, thereby significantly inducing the orientation behavior of parasitoids. Our study has confirmed that larval feeding can trigger TMTT emission through the activation of both JA and SA pathways to attract parasitoids; however, TMTT alone is less attractive than the complete blend of volatiles released by infested plants.

Topics: Animals; Cyclopentanes; Diptera; Feeding Behavior; Larva; Oviposition; Oxylipins; Phaseolus; Plant Defense Against Herbivory; Plant Leaves; Salicylates; Salicylic Acid; Volatile Organic Compounds

Chemical warfare (CW) exposure could be fatal to military and civilians through skin contamination. Our work and others focus on investigating stratum corneum reservoir with less regards to skin appendageal routes including hair follicles. Here, C-14 CW simulants (CWS) with specific activity of 0.1 mCi/ml were tested on abdominal and scalp human cadaver skin using flow-through diffusion system. Quantitative analysis of simulants in skin compartments were performed using scintillation counter. Scalp permeation of dipropylene glycol monomethyl ether (DPGME), diisopropyl methylphosphonate (DIMP) and methyl salicylate (MeS) exceed abdominal skin by 8%, 15%, and 6% (p value < 0.05) of applied dose, respectively. DPGME and DIMP (most hydrophilic) showed earlier permeation peak time (Tmax) through scalp skin at 2 and 4 h, respectively, comparing with 6 h with abdominal skin. The percentage of applied dose of DPGME and DIMP retained in human skin membrane (SC, epidermis, and viable dermis) showed no statistically significant difference between tested abdominal and scalp skin samples (p value >0.05). The percentage of applied dose of MeS in scalp showed higher partitioning in stratum corneum and viable epidermis than abdominal skin (p value <0.05). In conclusion, human scalp showed greater total skin absorption than abdominal skin. This work points to a qualitative importance of high follicular density body regions in percutaneous penetration and suggests that transfollicular pathway might have a significant role in early stage permeation of chemical warfare simulants. However, the difference noticed here between scalp and abdominal skin could be attributed to regional variability in anatomy, physiology, and barrier characteristics.

Topics: Chemical Warfare; Chemical Warfare Agents; Decontamination; Epidermis; Humans; Organophosphorus Compounds; Salicylates; Scalp; Skin; Skin Absorption

Gaultheria longibracteolata (Ericaceae) has been traditionally used by different linguistic groups in Yunnan Province, China, but it has not been well studied. Through our ethnobotanical study in Lüchun County of Yunnan, we found that this species has multiple traditional uses including food, medicine, and worship. The essential oils from the root, stem, and leaf were investigated by both GC-MS and anti-bacterial assays. The GC-MS study showed that methyl salicylate is the main (>90%) component of the essential oil, and the oil composition extracted from different plant parts showed some similarities. The oil of G. longibracteolata displayed antimicrobial activity against Escherichia coli, Klebsiella pneumoniae and Staphylococcus aureus, which is likely due to its methyl salicylate content. Gautheria longbracteolata appears to be a useful natural wintergreen oil substitute, but further studies are needed to develop this product.

Topics: Anti-Bacterial Agents; Gas Chromatography-Mass Spectrometry; Gaultheria; Microbial Sensitivity Tests; Oils, Volatile; Plant Extracts; Salicylates

The engineering of microbial metabolic pathways over the last two decades has led to numerous examples of cell factories used for the production of small molecules. These molecules have an array of utility in commercial industries and as

Topics: Bacteria; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Mass Spectrometry; Metabolic Engineering; Methyltransferases; Petunia; Plant Proteins; Plasmids; Salicylates

Methyl salicylate (MeSA) is a volatile biological compound synthesized from salicylic acid (SA) and is a plant hormone that helps defend against pests and pathogens. A major bacterial pathogen of rice, Xanthomonas oryzae pv. oryzae (Xoo) causes severe disease. Seed and plant treatments with MeSA can stimulate the defense enzyme peroxidase (POD) in plants. Response of peroxidase activity in rice (Oryza sativa L) cultivars IR 20, IR 50, IR 64, ASD 16, ASD 19 and ADT 46 to MeSA were measured under greenhouse conditions. Treatments of rice seedlings with MeSA at 50 and 100 mg L

Topics: Defense Mechanisms; Oryza; Plant Diseases; Salicylates; Seeds; Xanthomonas

Conservation biological control is a fundamental tactic in integrated pest management (IPM). Greater biological control services can be achieved by enhancing agroecosystems to be more favorable to the presence, survival, and growth of natural enemy populations. One approach that has been tested in numerous agricultural systems is the deployment of synthetic chemicals that mimic those produced by the plant when under attack by pests. These signals may attract arthropod natural enemies to crop habitats and thus potentially improve biological control activity locally. A 2-yr field study was conducted in the cotton agroecosystem to evaluate the potential of synthetic methyl salicylate (MeSA) to attract native arthropod natural enemies and to enhance biological control services on two key pests. Slow-release packets of MeSA were deployed in replicated cotton plots season long. The abundance of multiple taxa of natural enemies and two major pests were monitored weekly by several sampling methods. The deployment of MeSA failed to increase natural enemy abundance and pest densities did not decline. Predator to prey ratios, used as a proxy to estimate biological control function, also largely failed to increase with MeSA deployment. One exception was a season-long increase in the ratio of Orius tristicolor (White) (Hemiptera: Anthocoridae) to Bemisia argentifolii Bellows and Perring (= Bemisia tabaci MEAM1) (Hemiptera: Aleyrodidae) adults within the context of biological control informed action thresholds. Overall results suggest that MeSA would not likely enhance conservation biological control by the natural enemy community typical of U.S. western cotton production systems.

Topics: Animals; Arthropods; Ecosystem; Food Chain; Hemiptera; Pest Control, Biological; Salicylates

Adoxophyes honmai, a serious pest of tea plants, prefers to lay eggs on mature tea leaves rather than young leaves. Here, we examined a hypothesis that Ascogaster reticulata, an egg-larval parasitoid of A. honmai, increases the likelihood of encountering host egg masses by searching mature tea leaves when host-derived cues are not available. In a dual-choice bioassay using a four-arm olfactometer, A. reticulata preferred odor from intact, mature leaves versus young leaves. Based on volatile analysis with gas chromatography-mass spectrometry (GC-MS), we identified 5 and 10 compounds from mature and young leaf volatiles, respectively. The 5 components in the extract from intact mature leaves included (Z)-3-hexenyl acetate, (E)-β-ocimene, linalool, (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), and methyl salicylate. When each individual compound, or quaternary and quintenary blends of them, ratios of which were adjusted to match those of mature leaf volatiles, were provided, parasitoids preferred the full mixture and the quaternary blend devoid of DMNT to the solvent control. Methyl salicylate, one of the components of preferred blends, was not detected among young leaf volatiles. We concluded that the volatile composition of tea leaves changes, depending on their maturity, and that this composition affects foraging behavior of the parasitoid, which is closely related to the host herbivore's oviposition preference.

Topics: Acetates; Acyclic Monoterpenes; Alkenes; Animals; Camellia sinensis; Ecosystem; Gas Chromatography-Mass Spectrometry; Hymenoptera; Larva; Moths; Odorants; Plant Leaves; Salicylates; Terpenes; Volatile Organic Compounds

Insects possess a fairly sophisticated olfactory system in their antennae to detect odorants essential for their survival and reproduction. Among them, insect first perceives odour sources by odorant-binding proteins (OBPs) to locate host-plants. Methyl salicylate, (Z)-3-hexenyl acetate and dibutyl phthalate are major volatile components of Ulmus pumila and Ricinus communis and elicit strong responses of the scarab beetle Holotrichia oblita adults. However, olfactory perception of the scarab beetle to these odorant compounds is unclear. In the current study, we cloned the OBP6 and OBP7 of H. oblita. The expression pattern shows that the two genes were highly expressed in the antennae of female beetles. Binding assays verified that the HoblOBP6 had a better binding affinity to methyl salicylate, and so did HoblOBP7 to (Z)-3-hexenyl acetate and dibutyl phthalate. The effect on the responses of female beetles to the three compounds was decreased significantly after these two genes were silenced by RNA interference. These results indicate that HoblOBP6 and HoblOBP7 are essential for female H. oblita perception of methyl salicylate, (Z)-3-hexenyl acetate and dibutyl phthalate. Our study provides important insights into the olfactory mechanism of female H. oblita to ester plant volatiles and could facilitate the development of potential pest control strategies in the field.

Topics: Animals; Arthropod Antennae; Coleoptera; Dibutyl Phthalate; Esters; Female; Genes, Insect; Insect Control; Insect Proteins; Odorants; Olfactory Perception; Plants; Receptors, Odorant; Salicylates; Smell; Volatile Organic Compounds

Methyl salicylate, the major flavor component in wintergreen oil, is commonly used as food additives. It was found that amino acids can unexpectedly expedite methyl salicylate hydrolysis in an alkaline environment, while the detailed mechanism of this reaction merits investigation. Herein, the role of amino acid, more specifically, glycine, in methyl salicylate hydrolysis in aqueous solution was explored.

Topics: Amides; Amino Acids; Hydrolysis; Salicylates

Methyl salicylate (MeSA) is a plant metabolite that induces plant defence resistance and an odorous volatile compound presenting green nuances. This volatile compound was shown to be present in wine samples, sometimes at concentrations above its olfactory detection threshold. MeSA is localized in grapes, particularly in the skins and stems, and is extracted during red wine vinification. It was detected at the highest concentrations in wines of several grape varieties, made from grapes affected by cryptogamic diseases, namely downy mildew caused by Plasmopara viticola, and black rot caused by Guignardia bidwellii. It has also been detected in wines from vines affected by Esca, a Grapevine Trunk Disease. MeSA can also be considered to be a chemical marker in grapes and wine indicative of the level of development of several vine cryptogamic diseases.

Topics: Ascomycota; Chromatography, High Pressure Liquid; Fruit; Gas Chromatography-Mass Spectrometry; Humans; Plant Diseases; Salicylates; Solid Phase Extraction; Taste; Vitis; Wine

Fall armyworm (Spodoptera frugiperda) is a major global pest of many crops, including maize (Zea mays). This insect is known to use host plant-derived volatile organic compounds to locate suitable hosts during both its adult and larval stages, yet the function of individual compounds remains mostly enigmatic. In this study, we use a combination of volatile profiling, electrophysiological assays, pair-wise choice behavioral assays, and chemical supplementation treatments to identify and assess specific compounds from maize that influence S. frugiperda host location. Our findings reveal that methyl salicylate and (E)-alpha-bergamotene are oviposition attractants for adult moths but do not impact larval behavior. While geranyl acetate can act as an oviposition attractant or repellent depending on the host volatile context and (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) is an oviposition deterrent. These compounds can also be attractive to the larvae when applied to specific maize inbreds. These data show that S. frugiperda uses different plant volatile cues for host location in its adult and larval stage and that the background volatile context that specific volatiles are perceived in, alters their impact as behavioral cues.

Topics: Animals; Bridged Bicyclo Compounds; Gas Chromatography-Mass Spectrometry; Herbivory; Larva; Oviposition; Plant Leaves; Principal Component Analysis; Salicylates; Spodoptera; Terpenes; Volatile Organic Compounds; Zea mays

The effects of postharvest treatments with γ-aminobutyric acid (GABA), methyl jasmonate (MeJA) or methyl salicylate (MeSA) on antioxidant systems and sensory quality of blood oranges during cold storage were evaluated (150 days at 3 °C plus 2 days at 20 °C, shelf life). Fruit firmness, titratable acidity (TA), total antioxidant activity (TAA) and ascorbic acid (AA) decreased during cold storage, all these changes being delayed in treated fruit, with the greatest differences observed with the 50 µmol L

Topics: Acetates; Anthocyanins; Catechol Oxidase; Citrus sinensis; Cold Temperature; Cyclopentanes; Food Preservation; Fruit; gamma-Aminobutyric Acid; Glucosides; Nutritive Value; Oxylipins; Phenylalanine Ammonia-Lyase; Salicylates

In this work, we developed a number of generalised skin diffusion based pharmacokinetic models to relate published in vivo urinary excretion data to matching experimentally generated in vitro human skin permeation test (IVPT) data for a series of topically applied salicylate esters. A simplified linear in vivo model was found to inadequately describe the time course of urinary excretion over the entire sampling period. We represented the skin barrier as both a one layer (stratum corneum) and a two-layer (stratum corneum with viable epidermis) diffusion model and convoluted their Laplace solutions with that for a single exponential disposition phase to describe the urinary excretion profiles in the Laplace domain. We also derived asymptotic approximations for the model and estimated the conditions under which they could be used. We then sought to develop in vitro - in vivo relationships (IVIVR) for topically applied methyl, ethyl and glycol salicylates using our experimental IVPT data and the literature urinary excretion data. Good linear IVIVRs for ethyl and glycol salicylates were obtained, but the IVIVR for methyl salicylate was poor, perhaps because of topical stimulation of local skin blood flow by methyl salicylate. The ratio of the hydrated to dehydrated skin permeation for all salicylate esters was the same in both the IVPT and in vivo studies. A diffusion based one compartment pharmacokinetic model was also developed to describe the urinary excretion of solutes after removal of topical products and to compare the methyl salicylate skin permeation for five different body sites. The work presented here is consistent with the development of skin IVIVRs, but suggests that different skin conditions, application sites and local skin effects may affect model predictions.

Topics: Administration, Cutaneous; Diffusion; Female; Humans; Models, Biological; Permeability; Salicylates; Skin; Skin Absorption

Ambrosia beetles (Coleoptera: Curculionidae: Scolytinae and Platypodinae) bore into tree xylem to complete their life cycle, feeding on symbiotic fungi. Ambrosia beetles are a threat to avocado where they have been found to vector a symbiotic fungus, Raffaelea lauricola, the causal agent of the laurel wilt disease. We assessed the repellency of methyl salicylate and verbenone to two putative laurel wilt vectors in avocado, Xyleborus volvulus (Fabricius) and Xyleborus bispinatus (Eichhoff), under laboratory conditions. Then, we tested the same two chemicals released from SPLAT flowable matrix with and without low-dose ethanol dispensers for manipulation of ambrosia beetle populations occurring in commercial avocado. The potential active space of repellents was assessed by quantifying beetle catch on traps placed 'close' (~5-10 cm) and 'far' (~1-1.5 m) away from repellent dispensers. Ambrosia beetles collected on traps associated with all in-field treatments were identified to species to assess beetle diversity and community variation. Xyleborus volvulus was not repelled by methyl salicylate (MeSA) or verbenone in laboratory assays, while X. bispinatus was repelled by MeSA but not verbenone. Ambrosia beetle trap catches were reduced in the field more when plots were treated with verbenone dispensers (SPLAT) co-deployed with low-dose ethanol dispensers than when treated with verbenone alone. Beetle diversity was highest on traps deployed with low-dose ethanol lures. The repellent treatments and ethanol lures significantly altered the species composition of beetles captured in experiment plots. Our results indicate that verbenone co-deployed with ethanol lures holds potential for manipulating ambrosia beetle vectors via push-pull management in avocado. This tactic could discourage immigration and/or population establishment of ambrosia beetles in commercial avocado and function as an additional tool for management programs of laurel wilt.

Topics: Animals; Bicyclic Monoterpenes; Coleoptera; Insect Repellents; Insect Vectors; Ophiostomatales; Persea; Plant Diseases; Salicylates; Symbiosis

Topics: Acrylonitrile; Butylamines; Chemical Warfare Agents; Decontamination; Ethylene Glycols; Hazardous Substances; Humans; In Vitro Techniques; Lactates; Salicylates; Skin; Skin Absorption; Soaps; Water

Plants have evolved sophisticated defense mechanisms to overcome their sessile nature. However, if and how volatiles from cold-stressed plants can trigger interplant communication is still unknown. Here, we provide the first evidence for interplant communication via inducible volatiles in cold stress. The volatiles, including nerolidol, geraniol, linalool, and methyl salicylate, emitted from cold-stressed tea plants play key role(s) in priming cold tolerance of their neighbors via a C-repeat-binding factors-dependent pathway. The knowledge will help us to understand how plants respond to volatile cues in cold stress and agricultural ecosystems.

Topics: Acyclic Monoterpenes; Camellia sinensis; Cold-Shock Response; Salicylates; Sesquiterpenes

Salicylic acid (SA) and methyl salicylate (MeSA) are synthesized in many plants and are crucial components that establish their disease responses. The metabolism of airborne MeSA to SA has been previously reported. In this report, it was found that SA glucose ester (SAGE), ether (SAG), and salicyloyl-L-aspartic acid (SA-Asp) are metabolites of airborne MeSA. Furthermore, it was found that airborne MeSA was able to increase the endogenous amount of rosmarinic acid in

Topics: Air; Glucose; Plants; Salicylates

Alkaline phosphatases (ALPs) are membrane bound metalloenzymes, distributed all over the body. Recent studies have revealed that by targeting ALPs can lead towards the treatment of many deadliest diseases including cardiac, cancerous and brain diseases. Thioureas and their derivatives are of considerable significance and are privileged scaffolds in medicinal chemistry. They show a wide range of pharmacological activities such as antibacterial, antiparasitic, anti-inflammatory and antioxidants etc. On the other hand, salicylic acid and its derivatives are known for its broad spectrum of activities. The work presented comprises of synthesis of N-acyl-N'-aryl substituted bisthioureas of pimelic acid (1-7) and 3,5-dimethyl pyrazole (11), 1-aroyl-3-aryl thiourea (12) and 1,3,4-oxadiazole (13) derivatives of 4-methyl salicylic acid. Structures of all the synthesized compounds were characterized by FT-IR and

Topics: Alkaline Phosphatase; Enzyme Inhibitors; Hydrogen Bonding; Intestines; Molecular Docking Simulation; Pimelic Acids; Salicylates; Structure-Activity Relationship; Thiourea

To date, all human studies of mass-casualty decontamination for chemical incidents have relied on the collection and analysis of external samples, including skin and hair, to determine decontamination efficacy. The removal of a simulant contaminant from the surface of the body with the assumption that this translates to reduced systemic exposure and reduced risk of secondary contamination has been the main outcome measure of these studies. Some studies have investigated systemic exposure through urinary levels of simulant metabolites. The data obtained in these studies were confounded by high background concentrations from dietary sources. The unmetabolized simulants have never been analyzed in urine for the purposes of decontamination efficacy assessment.. Urinary simulant analysis could obviate the need to collect skin or hair samples during decontamination trials and provide a better estimate of both decontamination efficacy and systemic exposure. The study objective therefore was to determine whether gross skin contamination as part of a decontamination study would yield urine levels of simulants sufficient to evaluate systemic availability free from dietary confounders.. In this study, a gas chromatography-tandem mass spectrometry method was developed for the analysis of two chemical simulants, methyl salicylate (MeS) and benzyl salicylate (BeS), in urine. An extraction and sample clean-up method was validated, enabling quantitation of these simulants in urine. The method was then applied to urine collected over a 24-hour period following simulant application to the skin of volunteers.. Both MeS and BeS were present in all urine samples and were significantly increased in all post-application samples. The MeS levels peaked one hour after skin application. The remaining urinary levels were variable, possibly due to additional MeS exposures such as inhalation. In contrast, the urinary excretion pattern for BeS was more typical for urinary excretion curves, increasing clearly above baseline from four hours post-dose and peaking between 12.5 and 21 hours, a pattern consistent with dermal absorption and rapid excretion.. The authors propose BeS is a useful simulant for use in decontamination studies and that its measurement in urine can be used to model systemic exposures following skin application and therefore likely health consequences.

Topics: Adult; Chemical Hazard Release; Decontamination; Female; Gas Chromatography-Mass Spectrometry; Healthy Volunteers; Humans; Male; Mass Casualty Incidents; Salicylates; Urinalysis

Transdermal patches for analgesic purposes are widely used, however, their occlusive characteristics can often cause allergic reactions, irritating contact dermatitis, and allergic contact dermatitis upon extended use. Chitosan is a natural positively charged bioadhesive polysaccharide with several biological properties, being promising templates for sustained and controlled topical or transdermal drug delivery. Methyl salicylate (MS) is a non-steroidal topical anti-inflammatory drug (NSAID). MS is a lipophilic oily drug commonly found in transdermal patches, being difficult to incorporate into hydrophilic formulations such as Chitosan-based films. Thus, MS is a good candidate to be encapsulated into nanoemulsions (NE). This work reports the formulation development, physical-chemical characterization, and in vitro drug release of NE-loaded Chitosan films formulated with MS, as a novel substitute for transdermal analgesic patches. MS was encapsulated into NE, which were prepared by ultrasonication and presented 29.3 nm ± 0.1 and PdI 0.167 ± 0.005. The incorporation of MS into NE prevented phase separation and provided a homogeneous physical blending formulation, as confirmed by FTIR, TGA. NE-loaded films provided high drug incorporation in the films 94.08% ± 6.63%), and a smaller crystallinity degree in comparison with physical mixture films, suggesting a plasticizing effect of nano-sized droplets. Besides, mean weight, thickness, and moisture content were increased in NE-loaded films in comparison with chitosan-based control films. In vitro drug release from NE-loaded films was significantly higher than for physical mixture films, following Weibull and Korsmeyer-Peppas release kinetics models. The results suggest that NE-loaded chitosan film can increase the drug loading capacity of oil drugs and successfully control in vitro release, constituting a novel approach for transdermal drug delivery of NSAIDs.

Topics: Chitosan; Delayed-Action Preparations; Emulsions; Humans; Membranes, Artificial; Salicylates; Transdermal Patch

The main goal of this study was to describe impact of preharvest application of methyl salicylate (MeSA), acetyl salicylic acid (ASA) and salicylic acid (SA) on the reduction of disease caused by Botrytis cinerea in two table grape cultivars ('Crimson' and 'Magenta'). Based on previous studies, MeSA and SA were applied at 0.1 and 0.01 mM for both cultivars, while ASA was applied at 1 mM in 'Crimson' and 0.1 mM in 'Magenta'. At time of harvest, berry maturity-quality attributes, bioactive compounds and antioxidant enzymes were determined. In addition, grapes were artificially inoculated with B. cinerea spores, and the berries were ranked for visual decay incidence after 5 days of inoculation. Salicylates preharvest treatments led to higher total acidity, content of bioactive compounds and activity of antioxidant enzymes in treated than in control berries. The application of salicylate derivatives induced resistance to B. cinerea spoilage, since higher percentage of berries with no symptoms was observed and on the contrary, the highest percentages of berries were obtained in control grapes. All preharvest treatments with SA, ASA and MeSA alleviated postharvest disease caused by B. cinerea probably due to increasing levels of phenolic compounds and activity of antioxidant enzymes, although the best results were obtained with MeSA at 0.1 mM. Also, for this treatment and dose, higher quality properties, such as higher concentrations of ascorbic, succinic and fumaric acids, were observed compared with no treated-grapes.

Topics: Antioxidants; Aspirin; Botrytis; Disease Resistance; Food Preservation; Phenols; Plant Diseases; Salicylates; Salicylic Acid; Vitis

The pinewood nematode (PWN)

Topics: Animals; Antirheumatic Agents; Disease Resistance; Gene Expression Regulation, Plant; Nematoda; Pinus; Plant Diseases; Salicylates; Transcriptome

Obesity is a major worldwide public health issue that increases the risk to develop cardiovascular diseases, type-2 diabetes, and liver diseases. Obesity is characterized by an increase in adipose tissue (AT) mass due to adipocyte hyperplasia and/or hypertrophia, leading to profound remodeling of its three-dimensional structure. Indeed, the maximal capacity of AT to expand during obesity is pivotal to the development of obesity-associated pathologies. This AT expansion is an important homeostatic mechanism to enable adaptation to an excess of energy intake and to avoid deleterious lipid spillover to other metabolic organs, such as muscle and liver. Therefore, understanding the structural remodeling that leads to the failure of AT expansion is a fundamental question with high clinical applicability. In this article, we describe a simple and fast clearing method that is routinely used in our laboratory to explore the morphology of mouse and human white adipose tissue by fluorescent imaging. This optimized AT clearing method is easily performed in any standard laboratory equipped with a chemical hood, a temperature-controlled orbital shaker and a fluorescent microscope. Moreover, the chemical compounds used are readily available. Importantly, this method allows one to resolve the 3D AT structure by staining various markers to specifically visualize the adipocytes, the neuronal and vascular networks, and the innate and adaptive immune cells distribution.

Topics: Adipocytes; Adipose Tissue; Adipose Tissue, White; Animals; Humans; Imaging, Three-Dimensional; Mice; Microscopy, Fluorescence; Obesity; Salicylates

Species of the perennial woody plant genus Betula dominate subalpine forests and play a significant role in preserving biological diversity. In addition to their conventional benefits, birches synthesize a wide range of secondary metabolites having pharmacological significance. Methyl salicylate (MeSA) is one of these naturally occurring compounds constitutively produced by different birch species. MeSA is therapeutically important in human medicine for muscle injuries and joint pain. However, MeSA is now mainly produced synthetically due to a lack of information relating to MeSA biosynthesis and regulation. In this study, we performed a comprehensive bioinformatics analysis of two candidate genes mediating MeSA biosynthesis, SALICYLIC ACID METHYLTRANSFERASE (SAMT) and SALICYLIC ACID-BINDING PROTEIN 2 (SABP2), of high (B. lenta, B. alleghaniensis, B. medwediewii, and B. grossa) and low (B. pendula, B. utilis, B. alnoides, and B. nana) MeSA-producing birch species. Phylogenetic analyses of SAMT and SABP2 genes and homologous genes from other plant species confirmed their evolutionary relationships. Multiple sequence alignments of the amino acid revealed the occurrence of important residues for substrate specificity in SAMT and SABP2. The analysis of cis elements in different birches indicated a functional multiplicity of SAMT and SABP2 and provided insights into the regulation of both genes. We successfully developed six prominent single nucleotide substitution markers that were validated with 38 additional birch individuals to differentiate high and low MeSA-producing birch species. Relative tissue-specific expression analysis of SAMT in leaf and bark tissue of two high and two low MeSA-synthesizing birches revealed a high expression in the bark of both high MeSA-synthesizing birches. In contrast, SABP2 expression in tissues revealed indifferent levels of expression between species belonging to the two groups. The comparative expression and bioinformatics analyses provided vital information that could be used to apply plant genetic engineering technology in the mass production of organic MeSA.

Topics: Amino Acid Sequence; Betula; Conserved Sequence; Evolution, Molecular; Gene Expression Regulation, Plant; Phylogeny; Plant Proteins; Polymorphism, Genetic; Protein Domains; Salicylates; Sequence Analysis; Species Specificity

The glasshouse whitefly (Trialeurodes vaporariorum Westwood) is a polyphagous arthropod pest that is of particular detriment to glasshouse grown tomato (Solanum lycopersicum) across temperate regions of the world. Control of whiteflies with synthetic pesticides has resulted in the evolution of resistant genotypes and a reduction in natural enemies, thus highlighting the need for environmentally sound control strategies. Volatile organic compounds (VOCs) offer an environmentally benign alternative to synthetic chemical sprays and this study explored the use of VOCs as insect repellents and plant defence elicitors to control whiteflies on tomato in a commercial glasshouse setting. Limonene in the form of a volatile dispenser system was found to successfully repel whitefly from the target crop and increased fruit yield by 32% during a heavy whitefly infestation. Analysis of tomato herbivore induced plant volatiles (HIPVs) led us to select methyl salicylate (MeSA) as the plant elicitor and application of MeSA to un-infested tomato plants was found to successfully reduce whitefly population development and increase yield by 11%, although this difference was marginally statistically significant. Combination of these two methods was also effective but whitefly abundance in combined plots was similar to the standalone limonene treatment across the course of the experiment. All of the VOC based control methods we used had a negative impact on whitefly performance, with more pronounced effects during the first few weeks of infestation. In subsequent laboratory experiments, we found elevated peroxidase (POD) activity and a significant increase in TPX1 and PR1 transcripts in MeSA treated plants. This led us to deduce that MeSA immediately induced plant defences, rather than priming them. We did however see evidence for residual priming, as plants treated with MeSA and infested with whiteflies produced significantly higher levels of POD activity than whitefly infestation alone. Despite the fact that our treatments failed to synergise, our methods can be optimised further, and the effectiveness of the standalone treatments is promising for future studies. In particular, our repellent limonene dispensers were extremely effective at deterring whiteflies and offer a low economic cost and easy to implement whitefly control option. The methods we have used here could be incorporated into current integrated pest management (IPM) systems, a sustainable approach to pest contro

Topics: Animals; Arabidopsis Proteins; Cell Adhesion Molecules; Gene Expression Regulation; Hemiptera; Herbivory; Insect Control; Insect Repellents; Limonene; Peroxidase; Salicylates; Scavenger Receptors, Class E; Solanum lycopersicum; Volatile Organic Compounds

The UK Initial Operational Response (IOR) to chemical incidents includes improvised decontamination procedures, which use readily available materials to rapidly reduce risk to potentially exposed persons. A controlled, cross-over human volunteer study was conducted to investigate the effectiveness of improvised dry and wet decontamination procedures on skin, both alone, and in sequence. A simulant contaminant, methyl salicylate (MeS) in vegetable oil with a fluorophore was applied to three locations (shoulder, leg, arm). Participants then received no decontamination (control) or attempted to remove the simulant using one of three improvised protocols (dry decontamination; wet decontamination; combined dry and wet decontamination). Simulant remaining on the skin following decontamination was quantified using both Gas Chromatography Tandem Mass Spectrometry (GC-MSMS) for analysis of MeS and UV imaging to detect fluorophores. Additionally, urine samples were collected for 24 hours following application for analysis of MeS. Significantly less simulant was recovered from skin following each improvised decontamination protocol, compared to the no decontamination control. Further, combined dry and wet decontamination resulted in lower recovery of simulant when compared to either dry or wet decontamination alone. Irrespective of decontamination protocol, significantly more simulant remained on the shoulders compared to either the arms or legs, suggesting that improvised decontamination procedures are less effective for difficult to reach areas of the body. There was no effect of decontamination on excreted MeS in urine over 24 hours. Overall, findings indicate that improvised decontamination is an effective means of rapidly removing contaminants from skin, and combinations of improvised approaches can increase effectiveness in the early stages of decontamination and in the absence of specialist resources at an incident scene. However, the variable control and consistency of improvised decontamination techniques means that further intervention is likely to be needed, particularly for less accessible areas of the body.

Topics: Adult; Arm; Chemical Hazard Release; Cross-Over Studies; Decontamination; Female; Gas Chromatography-Mass Spectrometry; Healthy Volunteers; Humans; Leg; Male; Middle Aged; Plant Oils; Reproducibility of Results; Salicylates; Shoulder; Skin

Modulation by salicylic acid (SA) and its six esters of stomatal closure was evaluated in Arabidopsis thaliana. The seven compounds tested are salicylic acid (SA), acetylsalicylate (ASA), methyl salicylate (MeSA), propyl salicylate (PrSA), amyl salicylate, benzyl salicylate, and salicin. Among these, MeSA was the most effective to induce stomatal closure, followed by salicin and SA, while ASA was the least effective. Since SA, ASA, and MeSA could modulate plant function, the effects of these three compounds on the levels of reactive oxygen species (ROS) or nitric oxide (NO) in guard cells were studied. MeSA and SA raised the content of ROS or NO in as with ABA. The extent of ROS/NO production in response to ASA was the lowest. Reversal by cPTIO or catalase of stomatal closure by MeSA indicated the essentiality of NO and ROS for stomatal closure. Further studies revealed peroxidase as the ROS source during stomatal closure by MeSA, unlike the dominant role of NADPH oxidase in ROS production induced by ABA. The rise in NO production by ABA or MeSA was dependent on nitrate reductase and NO synthase-like enzyme. Given its most effective nature, MeSA can be an excellent tool to examine the signaling components in guard cells and other plant tissues. The ability of MeSA to induce stomatal closure is physiologically relevant because of its volatile nature, stability, and systemic action.

Topics: Abscisic Acid; Arabidopsis; Arabidopsis Proteins; Esters; Nitric Oxide; Plant Stomata; Reactive Oxygen Species; Salicylates; Salicylic Acid

Nicotiana tabacum overexpressing CrSAMT from Citrus reticulata increased production of MeSA, which works as an airborne signal in neighboring wild-type plants, inducing PR1 and increasing resistance to the pathogen Xylella fastidiosa. Xylella fastidiosa is one of the major threats to plant health worldwide, affecting yield in many crops. Despite many efforts, the development of highly productive resistant varieties has been challenging. In studying host plant resistance, the S-adenosyl-L-methionine: salicylic acid carboxyl methyltransferase gene (SAMT) from Citrus reticulata, a X. fastidiosa resistant species, was upregulated in response to pathogen infection. SAMT is involved with the catalysis and production of methyl salicylate (MeSA), an airborne signal responsible for triggering systemic acquired resistance. Here we used tobacco as a model system and generated transgenic plants overexpressing C. reticulata SAMT (CrSAMT). We performed an in silico structural characterization of CrSAMT and investigated its biotechnological potential in modulating the immune system in transgenic plants. The increase of MeSA production in transgenic lines was confirmed by gas chromatography (GC-MS). The transgenic lines showed upregulation of PR1, and their incubation with neighboring wild-type plants activated PR1 expression, indicating that MeSA worked as an airborne signal. In addition, transgenic plants showed significantly fewer symptoms when challenged with X. fastidiosa. Altogether, these data suggest that CrSAMT plays a role in host defense response and can be used in biotechnology approaches to confer resistance against X. fastidiosa.

Topics: Citrus; Gene Expression; Methyltransferases; Nicotiana; Plant Diseases; Recombinant Proteins; Salicylates; Volatilization; Xylella

The decontamination of exposed persons is a priority following the release of toxic chemicals. Efficacious decontamination reduces the risk of harm to those directly affected and prevents the uncontrolled spread of contamination. Human studies examining the effectiveness of emergency decontamination procedures have primarily focused on decontaminating skin, with few examining the decontamination of hair and scalp. We report the outcome of two studies designed to evaluate the efficacy of current United Kingdom (UK) improvised, interim and specialist mass casualty decontamination protocols when conducted in sequence. Decontamination efficacy was evaluated using two chemical simulants, methyl salicylate (MeS) and benzyl salicylate (BeS) applied to and recovered from the hair of volunteers. Twenty-four-hour urinary MeS and BeS were measured as a surrogate for systemic bioavailability. Current UK decontamination methods performed in sequence were partially effective at removing MeS and BeS from hair and underlying scalp. BeS and MeS levels in urine indicated that decontamination had no significant effect on systemic exposure raising important considerations with respect to the speed of decontamination. The decontamination of hair may therefore be challenging for first responders, requiring careful management of exposed persons following decontamination. Further work to extend these studies is required with a broader range of chemical simulants, a larger group of volunteers and at different intervention times.

Topics: Adult; Decontamination; Female; Hair; Healthy Volunteers; Humans; Male; Mass Casualty Incidents; Salicylates; Scalp; United Kingdom

Topics: Aged; Drug Overdose; Female; Humans; Insecticides; Oils, Volatile; Plant Extracts; Salicylates; Suicide, Attempted

Thrips Anaphothrips obscurus are one of the cosmopolitan major pests feeding on cereals and other grasses. In order to develop alternatives of chemical insecticides for thrips control, based on fumigant activity screening and evaluation of 22 essential oil (EO) compounds against the thrips, the binary interactions of methyl salicylate and carvacrol (MS-C) with high fumigant toxicity were studied systematically by bioassay and field trials.. The bioassay results showed that six in 22 EO compounds had high fumigant toxicity against both the second-instar nymphs and adults of A. obscurus, including methyl salicylate, carvacrol, thymol, trans-cinnamaldehyde, diallyl trisulfide, and L-perillaldehyde. Furthermore, the combination of methyl salicylate mixed with carvacrol at a volume ratio of 5:5 exhibited the most significant synergism against A. obscurus, with a poison ratio value of 1.32 and a co-toxicity coefficient of 151.15. The optimal formulation of microemulsion (ME) was composed of 5% methyl salicylate, 5% carvacrol, 46% adjuvant and 44% deionized water. The result of dynamic light scattering and stability showed that MS-C 10% ME was a transparent, single-phase and homogeneous liquid system. Field trials indicated that the ME displayed a significant control efficacy of about 89.17% on thrips in peppers, and 82.59% in broad bean on the seventh day post application with a dosage of 600.0 g A.I hm. The binary combination of MS-C possesses strikingly synergistic action against thrips A. obscurus, and the MS-C 10% ME has the potential to be developed as a botanical pesticide product for thrips control. © 2019 Society of Chemical Industry.

Topics: Animals; Cymenes; Insecticides; Oils, Volatile; Salicylates; Thysanoptera

The meadow moth Loxostege sticticalis is a serious agricultural pest that feeds on the leaves of many economic crops, such as sugar beet, soybean, sunflower, and potato. In addition to the rapid migration of adult moths, the collective foraging behavior of the larvae is also thought to be involved in the search for new food sources and substantially contributes to the expansion of the infested area. However, whether and how the chemical signals take part in this process remains unknown. In this study, two larva-specific expressed odorants, LstiOR5 and LstiOR6, were successfully cloned and deophanized. A heterologous study on Xenopus laevis oocytes showed that several host plant volatiles could evoke LstiOR responses in a dose-dependent manner. One herbivore-induced plant volatile (HIPV) of soybean leaves, methyl salicylate (MeSA), exerted attractive effects on the L. sticticalis larvae at all tested concentrations. Further foraging choice assays showed that the L. sticticalis larvae preferred foraged soybean leaves over unforaged leaves. When MeSA was artificially added to unforaged leaves, the unforaged leaves were preferred over the foraged leaves. In addition, GC-MS analysis demonstrated that MeSA was induced by the foraging behavior of the larvae and acted as a collective food signal in L. sticticalis. Moreover, in situ hybridization showed that LstiOR5 was highly expressed in larval antenna neurons. When LstiOR5 was silenced, both the electrophysiological response of the antenna to MeSA and the preference for foraged leaves were significantly decreased, suggesting that LstiOR5 is involved in the collective foraging behavior of L. sticticalis. Our results clarified the chemical signals that trigger the collective foraging behavior of L. sticticalis and provided more evidence for the molecular mechanism underlying the expansions of their infested areas at a peripheral olfactory sensing level. These findings could facilitate the development of potential control strategies for controlling this pest and provide a potential gene target that correlates with the collective foraging behavior of L. sticticalis, which might lead to better pest management.

Topics: Animals; Appetitive Behavior; Arthropod Antennae; Electrophysiological Phenomena; Feeding Behavior; Glycine max; Herbivory; Larva; Moths; Oocytes; Plant Leaves; Receptors, Odorant; Salicylates; Xenopus laevis

Topics: Chromatography, Liquid; Disaccharides; Glycosides; Humans; Plant Extracts; Plant Leaves; Salicylates; Vitis; Wine

The male butterfly Pieris napi produces the anti-aphrodisiac pheromone methyl salicylate (MeS) and transfers it to the female during mating. After mating she releases MeS, when courted by conspecific males, which decreases her attractiveness and the duration of male harassment, thus increasing her time available for egg-laying. In previous studies we have shown that males produced MeS from the amino acid L-phenylalanine (L-Phe) acquired during larval stage. In this study we show that adult males of P. napi can utilize L-Phe and aromatic flower volatiles as building blocks for production of anti-aphrodisiac pheromone and transfer it to females during mating. We demonstrate this by feeding butterflies with stable isotope labelled molecules mixed in sugar solutions, and, to mimic the natural conditions, we fed male butterflies with floral nectar of Bunias orientalis plants treated with labelled L-Phe. The volatiles from butterflies and plants were collected and identified by solid phase micro extraction, gas chromatography and mass spectrometry techniques. Since P. napi is polygamous, males would gain from restoring the titre of MeS after mating and the use of aromatic precursors for production of MeS could be considered as an advantageous trait which could enable butterflies to relocate L-Phe for other needs.

Topics: Animals; Aphrodisiacs; Butterflies; Female; Male; Phenylalanine; Pheromones; Salicylates; Sexual Behavior, Animal

The differences of volatile components in male (MFB) and female flower buds (FFB) of

Topics: Benzoates; Cyclohexanones; Flowers; Gas Chromatography-Mass Spectrometry; Populus; Salicylates; Solid Phase Microextraction; Volatile Organic Compounds

Some defects, such as the short persistence and lower release stability of methyl salicylate (MeSA), must be resolved before efficient field application. To enhance the utilization efficacy of MeSA, a slow-release MeSA alginate bead was designed and tested to measure its release rate in a laboratory environment and to obtain insights into its ecological effects in wheat fields.. In laboratory tests, both the 2.5 and 10 mL formulations of MeSA alginate beads (hereafter referred to as MeSA 2.5 and MeSA 10) release stably and continuously for at least 15 days, whereas pure MeSA does so for only ∼ 7 days. In field experiments, both the MeSA 2.5 bead and the MeSA 10 bead reduce the abundance of Sitobion avenae significantly and attract Metasyrphus corollae compared with the control. In addition, the effect of MeSA 10 beads is significantly greater than that of MeSA 2.5.. The MeSA alginate bead we manufactured could be an efficient slow-release formulation. The MeSA 10 bead had a significantly greater effect on S. avenae population suppression, partly by attracting M. corollae in fields. © 2018 Society of Chemical Industry.

Topics: Alginates; Animals; Aphids; Delayed-Action Preparations; Diptera; Pest Control, Biological; Pheromones; Salicylates; Triticum

After herbivore attack, plants express inducible resistance-related traits activated by hormones, mainly jasmonic acid (JA) and salicylic acid (SA). Methyl jasmonate (MeJa) is a biologically active methyl ester of JA. Exogenous applications of JA, SA, and MeJa induce responses similar to herbivory by insects. In this study, rice, Oryza sativa L. (Poaceae), plants were treated with two concentrations of MeJa (2 and 5 mmol L. Nymphs developing on plants treated with SA 16 mmol L. Rice plants possess defense mechanisms that can be elicited using hormones as elicitors, mainly SA 16 mmol L

Topics: Acetates; Animals; Cyclopentanes; Herbivory; Heteroptera; Nymph; Oryza; Oxylipins; Plant Growth Regulators; Salicylates; Salicylic Acid; Volatile Organic Compounds

Topics: Analgesics; Calibration; Chromatography, Gas; Monoterpenes; Ointments; Plant Preparations; Salicylates

The phytohormone salicylic acid (SA) is a secondary metabolite that regulates plant growth, development and responses to stress. However, the role of SA in the biosynthesis of flavonoids (a large class of secondary metabolites) in tea (

Topics: Flavonoids; Gene Expression Regulation, Plant; Metabolic Networks and Pathways; Plant Leaves; Propanols; Salicylates; Tea; Transcription, Genetic

Topics: Calibration; Decontamination; Gas Chromatography-Mass Spectrometry; Hair; Humans; Limit of Detection; Linear Models; Reproducibility of Results; Salicylates; Skin

Salicylic acid (SA) and its methyl ester, methyl salicylate (MeSA) are well known inducers of local and systemic plant defense responses, respectively. MeSA is a major mediator of systemic acquired resistance (SAR) and its conversion back into SA is thought to be required for SAR. In many plant species, conversion of MeSA into SA is mediated by MeSA esterases of the SABP2 family. Here we show that the Citrus sinensis SABP2 homologue protein CsMES1 catalyzes the hydrolysis of MeSA into SA. Molecular modeling studies suggest that CsMES1 shares the same structure and SA-binding mode with tobacco SABP2. However, an amino acid polymorphism in the active site of CsMES1-related proteins suggested an important role in enzyme regulation. We present evidence that the side chain of this polymorphic residue directly influences enzyme activity and SA binding affinity in CsMES proteins. We also show that SA and CsMES1 transcripts preferentially accumulate during the incompatible interaction between Xanthomonas aurantifolii pathotype C and sweet orange plants. Moreover, we demonstrate that SA and MeSA inhibited citrus canker caused by Xanthomonas citri, whereas an inhibitor of CsMES1 enhanced canker formation, suggesting that CsMES1 and SA play a role in the local defense against citrus canker bacteria.

Topics: Citrus sinensis; Disease Resistance; Plant Diseases; Plant Proteins; Salicylates; Structure-Activity Relationship

In some cultivars, yellowing resulting from chlorophyll breakdown has a direct and negative effect on food supply and health. The 'Zaosu' pear (Pyrus bretschneideri Rehd.), a commercial Asian pear cultivar in China, rapidly turns yellow when stored at room temperature after harvest. To develop techniques that delay or suppress chlorophyll degradation, the effects of methyl salicylate (MeSA) on yellowing in 'Zaosu' pear fruit during storage were evaluated.. Compared with the untreated fruit, the application of 0.05 mmol L. Methyl salicylate could delay chlorophyll breakdown in the fruit. The results also suggested that the conversion from chlorophyll a to pheophorbide a could proceed via two pathways, and that alternative pathways for the breakdown of chlorophyll a exist in 'Zaosu' pears. © 2019 Society of Chemical Industry.

Topics: Chlorophyll; Chlorophyll A; Chloroplasts; Food Preservation; Food Preservatives; Food Storage; Fruit; Pyrus; Salicylates

The indiscriminate use of antibiotics has led to the emergence of drug-resistant bacteria which has become one of the biggest challenges of the twenty-first century for the researchers to combat and in turn search for novel targets which could lead to the development of effective and sustainable therapies. Inhibition of biofilm formation and virulence of bacterial pathogens is an emerging approach to address the challenges related to bacterial infections. To suppress the virulence and biofilm formation by Escherichia coli O157:H7 (ECOH), we developed stable nanoemulsion (NE) of Gaultheria fragrantissima Wall. essential oil's (EO) bioactive compounds, viz., eugenol (E-NE) and methyl salicylate (MS-NE) that showed significantly higher anti-biofilm and anti-virulence activities as compared to eugenol and methyl salicylate without affecting ECOH planktonic cell growth. Transcriptional analysis showed that E-NE and MS-NE reduced the expression of genes, including curli, type I fimbriae, Shiga-like toxins, quorum sensing, and ler-controlled toxins, which are needed for biofilm formation, pathogenicity, and attachment. E-NE and MS-NE loaded hydrogel coatings showed superior anti-biofilm activity against ECOH on glass, plastic and meat surfaces as compared to eugenol and methyl salicylate loaded coatings. Conclusively, NE-loaded hydrogel coatings could be used in combating ECOH infection on solid surfaces through anti-biofilm and anti-virulence strategies.

Topics: Bacterial Adhesion; Biofilms; Coated Materials, Biocompatible; Emulsions; Escherichia coli O157; Eugenol; Glass; Hydrogels; Nanostructures; Oils, Volatile; Salicylates; Virulence

The effects of ethanol treatment on quality characteristics of cherry tomatoes were investigated over 11 days of storage at room temperature (25 °C). Results showed that sensory quality was improved after ethanol treatment, with redder, softer fruits at the edible stage (11 days) compared with control fruit. In addition, the contents of ascorbic acid, sucrose and fructose were elevated after ethanol treatment as well as the concentration of 6-methyl-5-hepten-2-one. Conversely, decreased levels of methyl salicylate (MeSA), guaiacol, (Z)-3-hexenal and (E)-2-hexenal were observed. Selected consumers showed a preference for ethanol-treated cherry tomato fruits compared with controls. Taken together, 0.1% ethanol application has the potential to improve the quality characteristics of cherry tomatoes stored at room temperature.

Topics: Aldehydes; Ascorbic Acid; Chromatography, High Pressure Liquid; Discriminant Analysis; Ethanol; Flavoring Agents; Fruit; Humans; Least-Squares Analysis; Salicylates; Solanum lycopersicum; Sugars; Temperature; Volatile Organic Compounds

Blood orange is sensitive to chilling injury (CI) depending on cultivar and storage temperature. Postharvest treatments with γ-aminobutyric acid (GABA), methyl jasmonate (MeJA), or methyl salicylate (MeSA) are known to alleviate CI. γ-Aminobutyric acid aqueous solution, applied at 20 and 40 mM, was vacuum-infiltrated at 30 kPa for 8 min at 20 °C. Methyl jasmonate or MeSA vapor treatments were applied separately at 50 and 100 μM by putting the fruit in 20 L plastic containers for 18 h at 20 °C. There have been no reports about postharvest treatments of GABA, MeJA, or MeSA on enhancing the tolerance of 'Moro' blood orange to chilling during long-term cold storage at 3 °C for 150 days, which was the subject of this study.. All treatments significantly alleviated CI symptoms of blood orange manifested by lower electrolyte leakage (EL), malondialdehyde (MDA), hydrogen peroxide (H

Topics: Acetates; Ascorbate Peroxidases; Catalase; Citrus sinensis; Cold Temperature; Cyclopentanes; Food Preservation; Food Preservatives; Food Storage; Fruit; gamma-Aminobutyric Acid; Oxylipins; Plant Proteins; Salicylates

Topics: Glycosylation; Plants; Salicylates; Sugars

Monoterpene alcohols (MTAs) are characteristic flavour-imparting compounds in sweet potato shochu (Japanese distilled spirit) that are liberated following hydrolysis by specific enzymes during fermentation. In the present study, we evaluated the effect of an exogenously added diglycoside-specific β-glycosidase (β-primeverosidase) on aroma formation during shochu brewing using various sweet potato species to address whether MTAs are predominantly present as diglycosidic precursors in raw materials. The results showed that the amount of MTAs produced from enzyme-treated mash was dramatically increased by 2- to 9-fold compared with untreated controls, and the increase varied with sweet potato species. In addition, levels of methyl salicylate, 1-octene-3-ol and ethyl benzoate were also elevated by enzyme treatment. These results indicate that a large amount of MTAs and other volatile aroma compounds are stored in the form of disaccharide β-glycosides such as β-primeverosides in sweet potato. This enzyme may therefore be useful for controlling aroma formation during shochu manufacturing, and may ultimately contribute to diversifying shochu quality.

Topics: Alcoholic Beverages; Alcohols; Benzoates; Disaccharides; Fermentation; Flavoring Agents; Glycoside Hydrolases; Glycosides; Hydrolysis; Ipomoea batatas; Monoterpenes; Octanols; Odorants; Salicylates

Chemical warfare agents have been used to incapacitate, injure or kill people, in a context of war or terrorist attack. It has previously been shown that hair could trap the sulphur mustard simulants methyl salicylate and 2-chloroethyl ethyl sulphide. In order to investigate simulants persistency in hair after intense vapour exposure, their desorption kinetics were studied by using two complementary methods: hair residual content measurement and desorbed vapour monitoring. Results showed that both simulants were detected in air and could be recovered from hair 2 h after the end of exposure. Longer experiments with methyl salicylate showed that it could still be recovered from hair after 24 h. Our data were fitted with several kinetic models and best correlation was obtained with a bimodal first-order equation, suggesting a 2-step desorption kinetics model: initial fast regime followed by a slower desorption. 2-chloroethyl ethyl sulphide was also detected in the immediate environment after hair exposure for 2 h, and hair simulant content decreased by more than 80%. Our results showed that hair ability to release formerly trapped chemical toxics could lead to health hazard. Their persistency however confirmed the potentiality of hair analysis as a tool for chemical exposure assessment.

Topics: Chemical Warfare Agents; Environmental Exposure; Gases; Hair; Kinetics; Mustard Gas; Salicylates; Scalp

Postharvest diseases result in major losses in fruits. Tomato is susceptible to postharvest rot caused by Botrytis cinerea and is regarded as a good model system to study postharvest disease and quality deterioration in fruit. To develop a safe and effective technique to alleviate disease and maintain fruit quality, the effects of methyl salicylate (MeSA) and 1-methylcyclopropene (1-MCP) either separately or combined on quality and gray mold caused by B. cinerea in tomato fruit were investigated.. The results showed that application of MeSA (0.05 mmol L. MeSA combined with 1-MCP treatment was a useful technique to maintain quality and alleviate gray mold in postharvest tomato fruit during storage. © 2018 Society of Chemical Industry.

Topics: Botrytis; Cyclopropanes; Food Preservation; Food Preservatives; Fruit; Plant Diseases; Salicylates; Solanum lycopersicum

Topics: Metal Nanoparticles; Salicylates; Silver; Spectrum Analysis, Raman; Surface Properties

Optimal imaging methods are necessary in order to perform a detailed characterization of thick tissue samples from either native or engineered tissues. Tissue-engineered substitutes are featuring increasing complexity including multiple cell types and capillary-like networks. Therefore, technical approaches allowing the visualization of the inner structural organization and cellular composition of tissues are needed. This chapter describes an optical clearing technique which facilitates the detailed characterization of whole-mount samples from skin and adipose tissues (ex vivo tissues and in vitro tissue-engineered substitutes) when combined with spectral confocal microscopy and quantitative analysis on image renderings.

Topics: Adipose Tissue; Antibodies; Apoptosis; Benzothiazoles; Bisbenzimidazole; Cell Death; Diamines; Fluorescent Dyes; Humans; Microscopy, Confocal; Optical Imaging; Organic Chemicals; Quinolines; Salicylates; Skin; Skin, Artificial; Tissue Engineering

This study aimed to investigate the effects of different microbial growth media on the laboratory assessment of antimicrobial activity of natural polyphenolic compounds. The inhibition of the tea polyphenol EGCG on growth of selected oral microorganisms was evaluated in complex media and a protein-free chemically defined medium (CDM). Other antimicrobial agents (polyphenolic grape seed extract, plant alkaloid berberine, methyl salicylate, and chlorhexidine gluconate) were also tested in the study. The presence of proteins and their effects on the antimicrobial activity of EGCG were investigated by the addition of BSA to the CDM. The MICs of EGCG against test oral microorganisms were 4 to 64 times higher in complex media than in CDM. The polyphenolic grape seed extract exhibited similar discrepancies. However, the MICs of the nonpolyphenolic compounds (berberine, methyl salicylate, and chlorhexidine) were not significantly different between the two growth media. The MIC of EGCG against

Topics: Anti-Bacterial Agents; Bacteria; Berberine Alkaloids; Chlorhexidine; Culture Media; Grape Seed Extract; Microbial Sensitivity Tests; Plant Extracts; Polyphenols; Salicylates; Tea

Methyl salicylate (MeSA) is a long-distance signal transduction chemical that plays an important role in plant responses to abiotic stress and herbivore and pathogen attacks. However, it is unclear how photosynthesis and elicitation of plant volatile organic compounds (VOC) from different metabolic pathways respond to the dose of MeSA. We applied different MeSA concentrations (0-50 mM) to study how exogenous MeSA alters VOC profiles of silver birch (Betula pendula Roth) leaves from application through recovery (0.5-23 h). Methyl salicylate application significantly reduced net assimilation rate in 10 mM and 20 mM MeSA-treated plants. No significant effects of MeSA were observed on the stomatal conductance at any MeSA concentration. Methyl salicylate elicited emissions of benzenoids (BZ), monoterpenes (MT) and fatty acid derived compounds (LOX products). Emission rates of BZ were positively, but emission rates of MT were negatively correlated with MeSA concentration. Total emission of LOX products was not influenced by MeSA concentration. Emission rate of MT was negatively correlated with BZ and the share of MT in the total emission blend decreased and the share of BZ increased with increasing MeSA concentration. Although the share of LOX products was similar across MeSA treatments, some LOX products responded differently to MeSA concentration, ultimately resulting in unique VOC blends. Overall, this study demonstrates inverse responses of MT and BZ to different MeSA doses such that plant defense mechanisms induced by lower MeSA doses mainly lead to enhanced MT synthesis, whereas greater MeSA doses trigger BZ-related defense mechanisms. Our results will contribute to improving the understanding of birch defenses induced upon regular herbivore attacks and pathogen infections in boreal forests.

Topics: Betula; Biosynthetic Pathways; Dose-Response Relationship, Drug; Photosynthesis; Plant Leaves; Salicylates; Shikimic Acid; Terpenes; Volatile Organic Compounds

Plant defence responses to various biotic stresses via systemic acquired resistance (SAR) are induced by avirulent pathogens and chemical compounds, including certain plant hormones in volatile form, such as methyl salicylate and methyl jasmonate. SAR refers to the observation that, when a local part of a plant is exposed to elicitors, the entire plant exhibits a resistance response. In the natural environment, plants are continuously exposed to avirulent pathogens that induce SAR and volatile emissions affecting neighbouring plants as well as the plant itself. However, the underlying mechanism has not been intensively studied. In this study, we evaluated whether plants "memorise" the previous activation of plant immunity when exposed repeatedly to plant defensive volatiles such as methyl salicylate and methyl jasmonate. We hypothesised that stronger SAR responses would occur in plants treated with repeated applications of the volatile plant defence compound MeSA than in those exposed to a single or no treatment.

Topics: Memory; Plant Immunity; Plants; Salicylates

The salicylic acid (SA) plays a critical role during the establishment of systemic acquired resistance (SAR) in uninfected plant tissues after localised exposure to a pathogen. Here, we studied SA in Populus tomentosa infected by the plant pathogen Botryosphaeria dothidea. The accumulation of SA and methyl salicylate (MeSA) occurred in chronological order in P. tomentosa. The SA and MeSA contents were greater at infected than uninfected sites. Additionally, a gene expression analysis indicated that SA might be accumulated by phenylalanine ammonialyase (PAL) and converted to MeSA by SA carboxyl methyltransferase (SAMT), while MeSA might convert to SA by SA-binding protein 2 (SABP2). The expressions of SAMT at infected sites and SABP2 at uninfected sites, respectively, were significantly up-regulated. Thus, SA might be converted to MeSA at infected sites and transported as a signalling molecule to uninfected sites, where it is converted to SA for SAR. Moreover, the expressions of pathogenesis-related genes PR-1, PR-2 and PR-5 in P. tomentosa were up-regulated by the B. dothidea infection. Our study determined that variations in SA and MeSA contents occur at infected and uninfected sites in poplar after pathogen infection and contributed to the remote signals for poplar SAR.

Topics: Gene Expression Profiling; Gene Expression Regulation, Plant; Methyltransferases; Phenylalanine Ammonia-Lyase; Plant Proteins; Populus; Saccharomycetales; Salicylates; Salicylic Acid; Signal Transduction

The removal of three emerging contaminants (ECs) (amitriptyline hydrochloride (AH), methyl salicylate (MS) and 2-phenoxyethanol (PE)) dissolved in several water matrices by means of their adsorption onto powdered activated carbon (PAC) and granular activated carbon (GAC) has been investigated. When dissolved in ultrapure water, adsorption of the ECs followed the trend of AH > MS > PE, with a positive effect of the adsorbent dose. According to the analysis of the adsorption isotherms and adsorption kinetics, PAC showed strongly higher adsorption efficiency in both capacity and velocity of the adsorption, in agreement with its higher mesoporosity. Equilibrium isotherm data were fitted by Langmuir and Freundlich models. Pseudo-second order kinetics modeled very successfully the adsorption process. Finally, the effect of the presence of dissolved organic matter (DOM) in the water matrices (ultrapure water, surface water and two effluents from wastewater treatment plants) on the adsorption of the selected ECs onto PAC was established, as well as its performance on the removal of water quality parameters. Results show a negative effect of the DOM content on the adsorption efficiency. Over 50% of organic matter was removed with high PAC doses, revealing that adsorption onto PAC is an effective technology to remove both micro-pollutants and DOM from water matrices.

Topics: Adsorption; Amitriptyline; Charcoal; Ethylene Glycols; Humic Substances; Kinetics; Models, Theoretical; Porosity; Salicylates; Wastewater; Water Pollutants, Chemical; Water Purification; Water Quality

Low temperatures are often used to reduce metabolic processes and extend the storage life of fruit; however, in the case of avocado, a temperature below 3 °C will often result in the development of physiological disorders associated with chilling injury. The objective of this study was to investigate the ability of methyl jasmonate (MeJA) and methyl salicylate (MeSA) vapours to alleviate chilling injury in 'Hass' avocado fruit kept at 2 °C for 21 days followed by 6-7 days of shelf-life at 20 °C, simulating supply chain conditions.. The incidence and severity of chilling injury were significantly reduced in MeJA- and MeSA-exposed fruit, especially at 100 µmol L. MeJA and MeSA have the potential for being used with 'Hass' avocado fruit shipped at low temperature to reduce its susceptibility to chilling injury. © 2017 Society of Chemical Industry.

Topics: Acetates; Cold Temperature; Cyclopentanes; Fatty Acids; Food Preservation; Food Preservatives; Food Storage; Fruit; Oxylipins; Persea; Salicylates

The effects of l-arginine (Arg, 1 mM) and/or methyl salicylate (MeSA, 0.05 mM) treatment on gray mold caused by Botrytis cinerea in tomato fruit were studied. Results indicated that Arg or MeSA alleviated the incidence and severity of fruit disease caused by B. cinerea, and that both Arg and MeSA (Arg + MeSA) further inhibited the development of fruit decay. Treatment with Arg + MeSA not only enhanced the activities of superoxide dismutase, catalase, and peroxidase but also promoted the expression levels of pathogenesis-related protein 1 gene and the activities of defense-related enzymes of phenylalanine ammonia-lyase, polyphenol oxidase, β-1,3-glucanase, and chitinase during most of the storage periods, which were associated with lower disease incidence and disease index. In addition, the combined treatment elevated the levels of total phenolics, polyamines, especially putrescine, and nitric oxide. These observations suggest that treatment of fruit with Arg + MeSA is an effective and promising way to alleviate postharvest decays on a commercial scale.

Topics: Arginine; Botrytis; Drug Synergism; Food Preservation; Food Preservatives; Fruit; Plant Diseases; Salicylates; Solanum lycopersicum

Development of anthracnose disease caused by Colletotrichum gloeosporioides Penz. is one of the major issues within the avocado supply chain. Exposure to methyl jasmonate (MeJA) and methyl salicylate (MeSA) vapours at 10 and 100µmoll

Topics: Acetates; Colletotrichum; Cyclopentanes; Fruit; Fungicides, Industrial; Oxylipins; Persea; Plant Diseases; Salicylates

Synthetic plant volatile lures attract natural enemies, but may have non-target effects due to the multifunctional nature of volatile signals. For example, methyl salicylate (MeSA) is used to attract predators, yet also serves as a signaling hormone involved in plant pathogen defense. We investigated the consequences of deploying MeSA lures to attract predators for tomato (Solanum lycopersicum) defense against herbivores. To understand the spatial distribution of the lure's effect, we exposed tomatoes in the field to MeSA along a linear distance gradient and induced defenses by simulating feeding by hornworm caterpillars in a fully crossed factorial design (+/- MeSA, +/- herbivory). Subsequently, we analyzed activity of several defensive proteins (protease inhibitors, polyphenol oxidase, peroxidase), development of hornworm larvae (Manduca sexta), growth of fungal pathogens (Cladosporium and Alternaria), and attractiveness to herbivores and predators. Overall, MeSA-exposed plants were more resistant to both insects and pathogens. Secondary pathogen infection was reduced by 25% in MeSA exposed plants, possibly due to elevated polyphenol oxidase activity. Interestingly, we found that lures affected plant pathogen defenses equivalently across all distances (up to 4 m away) indicating that horizontal diffusion of a synthetic volatile may be greater than previously assumed. While thrips avoided colonizing hornworm- damaged tomato plants, this induced resistance was not observed upon pre-exposure to MeSA, suggesting that MeSA suppresses the repellant effect induced by herbivory. Thus, using MeSA lures in biological control may inadvertently protect crops from pathogens, but has mixed effects on plant resistance to insect herbivores.

Topics: Alternaria; Animals; Catechol Oxidase; Cladosporium; Herbivory; Larva; Manduca; Peroxidase; Pest Control, Biological; Plant Leaves; Protease Inhibitors; Salicylates; Solanum lycopersicum; Tandem Mass Spectrometry; Volatile Organic Compounds

Acute ozone exposure triggers major emissions of volatile organic compounds (VOCs), but quantitatively, it is unclear how different ozone doses alter the start and the total amount of these emissions, and the induction rate of different stress volatiles. It is also unclear whether priming (i.e. pre-exposure to lower O

Topics: Chlorophyll; Fluorescence; Kinetics; Lipoxygenase; Methanol; Ozone; Phaseolus; Photosynthesis; Plant Stomata; Salicylates; Stress, Physiological; Time Factors; Volatile Organic Compounds

Topics: Animals; Cytokines; Dinitrochlorobenzene; Ear Auricle; Female; Gene Expression Regulation; Local Lymph Node Assay; Mice; Mice, Inbred CBA; Oxazolone; Salicylates; Skin; Sodium Dodecyl Sulfate; Toluene 2,4-Diisocyanate; Transcriptome

Olfaction is mediated by the binding of odorant molecules to olfactory receptors (ORs). There are numerous proteins in the nasal mucus, and they contribute to olfaction through various mechanisms. Cytochrome P450 (CYP) family members are known to be present in the olfactory epithelium and are thought to affect olfaction by enzymatic conversion of odorant molecules. In this study, we examined the effects of CYPs on the ligand responses of ORs in heterologous cells. Among the CYPs tested, co-expression of CYP1a2 significantly affected the responses of various ORs, including MOR161-2, to acetophenone. Conversion of acetophenone to methyl salicylate was observed in the medium of CYP1a2-expressing cells. MOR161-2-expressing cells exhibited significantly greater responses to methyl salicylate than to acetophenone. Finally, we analyzed the responses of olfactory neurons expressing MOR161-2 in vivo using the phosphorylated ribosomal protein S6 as a marker. MOR161-2 responded to both acetophenone and methyl salicylate in vivo. When the olfactory mucus was washed out by the injection of PBS to mouse nasal cavity, the response of MOR161-2 to acetophenone was reduced, while that to methyl salicylate did not change. Our data suggest that CYP1a2 affects OR activation by converting acetophenone to methyl salicylate.

Topics: Acetophenones; Animals; Cell Line; Cytochrome P-450 CYP1A2; Humans; Mice; Olfactory Receptor Neurons; Receptors, Odorant; Salicylates; Transcriptional Activation

Plant quality and predators are important factors affecting herbivore population growth, but how they interact to regulate herbivore populations is not well understood. We manipulated jasmonate-induced plant resistance, exposure to the natural predator community and herbivore density to test how these factors jointly and independently affect herbivore population growth. On low-resistance plants, the predator community was diverse and abundant, promoting high predator consumption rates. On high-resistance plants, the predator community was less diverse and abundant, resulting in low predator consumption rate. Plant resistance only directly regulated aphid population growth on predator-excluded plants. When predators were present, plant resistance indirectly regulated herbivore population growth by changing the impact of predators on the herbivorous prey. A possible mechanism for the interaction between plant resistance and predation is that methyl salicylate, a herbivore-induced plant volatile attractive to predators, was more strongly induced in low-resistance plants. Increased plant resistance reduced predator attractant lures, preventing predators from locating their prey. Low-resistance plants may regulate herbivore populations via predators by providing reliable information on prey availability and increasing the effectiveness of predators.

Topics: Animals; Aphids; Cyclopentanes; Herbivory; Oxylipins; Plant Physiological Phenomena; Plants; Population Growth; Predatory Behavior; Salicylates

In this research the effect of salicylic acid (SA), acetylsalicylic acid (ASA), and methylsalicylate (MeSA) treatments, applied as a foliar spray during on-tree plum development, on fruit quality attributes, bioactive compounds, antioxidant activity, and the activity of the antioxidant enzymes at harvest and after long-term cold storage was evaluated in two plum cultivars ("Black Splendor", BS, and "Royal Rosa", RR). At harvest, plum quality parameters, such as weight, total phenolics (including anthocyanins, in BS), total carotenoids, and antioxidant activity, in both hydrophilic and lipophilic compounds were found at higher levels in plums from SA-, ASA-, and MeSA-treated trees than in those from control trees. During storage, fruit firmness, total acidity, and antioxidant compounds were at higher levels in treated, than in control, plums, which show an effect of salicylate treatments on delaying the plum postharvest ripening process. In addition, the activity of the antioxidant enzymes catalase (CAT), peroxidase (POX), superoxide dismutase (SOD), and ascorbate peroxidase (APX) were also enhanced at the time of harvest in salicylate-treated plums as compared with plums from control trees. The activity of these antioxidant enzymes was also found at higher levels in salicylate-treated plums during storage. Thus, preharvest treatment with salicylates could be a safe, eco-friendly, and new tool to improve and maintain plum quality attributes, and especially their content of antioxidant compounds, with an additional effect on delaying the postharvest ripening process through increasing the levels of antioxidant compounds and the activity of the antioxidant enzymes.

Topics: Antioxidants; Ascorbate Peroxidases; Catalase; Plant Extracts; Prunus domestica; Salicylates; Salicylic Acid; Superoxide Dismutase

A new series of tertiary-butyl ammonium (TBA) salts of various nonsteroidal anti-inflammatory drugs (NSAIDs) have been synthesized and characterized. Nearly 90 % of the NSAID-derived primary ammonium monocarboxylate (PAM) salts displayed remarkable gelation ability with various solvents including methyl salicylate. Single crystal X-ray diffraction data (SXRD) revealed the existence of 1D PAM synthon in the gelator salts. Structure-property correlation studies based on SXRD and powder X-ray diffraction (PXRD) data established the presence of the 1D PAM synthon in the bulk salts as well as in the corresponding xerogels. A parallel series of salts derived from TRIS (2-amino-2-(hydroxymethyl)-1,3-propanediol) and the same set of NSAIDs displayed poor gelation ability; only 33 % of the salts in the series displayed gelation ability. A few selected gelator salts of both TBA and TRIS were found to be biocompatible (MTT assay with RAW 264.7 cell line) and two of the selected salts (FLR.TBA and FLR.TRIS) possessed anti-inflammatory properties equal to the parent drug FLR (flurbiprofen). Finally a methyl salicylate topical gel derived from FLR.TRIS was successfully delivered in a self-delivery fashion to treat inflamed skin conditions in the mice model. Histological studies of the dorsal tissues of the untreated and treated mice clearly demonstrated the effect of topical gels in such treatment.

Topics: Administration, Topical; Aminoquinolines; Animals; Anti-Inflammatory Agents, Non-Steroidal; Gels; Imiquimod; Mice; RAW 264.7 Cells; Salicylates; Skin Diseases; X-Ray Diffraction

The cotton aphid, Aphis gossypii (Glover) (Hemiptera: Aphididae), is a major pest of many crops worldwide and a major cucumber plant pest in Taiwan. Because cotton aphids rapidly develop insecticide resistance and because of the insecticide residue problem, a safe and sustainable method is required to replace conventional chemical control methods. Methyl salicylate (MeSA), a herbivore-induced plant volatile, has been shown to affect aphids' behavior and attract the natural enemies of aphids for reducing their population. Therefore, this study examined the direct effects of MeSA on cotton aphids' settling preference, population development, and attractiveness to natural enemies. The efficiency of using MeSA and the commercial insecticide pymetrozine for reducing the cotton aphid population in laboratory and outdoor cucumber plant pot was also examined. The results showed no difference in winged aphids' settling preference and population development between the MeSA and blank treatments. Cucumber plants infested with cotton aphids and baited with 0.1% or 10% MeSA contained significantly higher numbers of the natural enemy of cotton aphids, namely Scymnus (Pullus) sodalis (Weise) (Coleoptera: Coccinellidae), and MeSA-treated cucumber plants contained a lower number of aphids. Significantly lower cotton aphid numbers were found on cucumber plants within a 10-m range of MeSA application. In addition, fruit yield showed no difference between the MeSA and pymetrozine treatments. According to our findings, 0.1% MeSA application can replace insecticides as a cotton aphid control tool. However, large-scale experiments are necessary to confirm its efficiency and related conservation biological control strategies before further use.

Topics: Animals; Aphids; Behavior, Animal; Coleoptera; Cucumis sativus; Food Chain; Salicylates

Methyl salicylate (MeSA) is one of the volatile organic compounds (VOCs) that releases floral scent and plays an important role in the sweet flowery aroma of tea. During the withering process for white tea producing, MeSA was generated by salicylic acid carboxyl methyltransferase (SAMT) with salicylic acid (SA), and the specific floral scent was formed. In this study, we first cloned a CsSAMT from tea leaves (GenBank accession no. MG459470) and used Escherichia coli and Saccharomyces cerevisiae to express the recombinant CsSAMT. The enzyme activity in prokaryotic and eukaryotic expression systems was identified, and the protein purification, substrate specificity, pH, and temperature optima were investigated. It was shown that CsSAMT located in the chloroplast, and the gene expression profiles were quite different in tea organs. The obtained results might give a new understanding for tea aroma formation, optimization, and regulation and have great significance for improving the specific quality of white tea.

Topics: Camellia sinensis; Enzyme Stability; Food Handling; Hydrogen-Ion Concentration; Methyltransferases; Plant Leaves; Plant Proteins; Salicylates; Temperature; Volatile Organic Compounds

Topics: Administration, Cutaneous; Analgesics; Burns; Female; Hot Temperature; Humans; Middle Aged; Musculoskeletal Pain; Nonprescription Drugs; Salicylates

Methyl salicylate based vortex-assisted surfactant-enhanced emulsification microextraction (MeSA-VASEME) has been developed and applied for rapid preconcentration of fungicides (i.e., carbendazim, thiabendazole, and fluberidazole) in honey samples followed by high performance liquid chromatographic analysis. MeSA was used as an extraction solvent, while surfactant was used to enhance the extraction performance under the dispersion by vortex agitation. The optimum MeSA-VASEME conditions were 100 μL MeSA, 2.0 mmol L‒1 sodium dodecyl sulfate, and vortex agitation at 1200 rpm for 90 s. Preconcentration factors were obtained in the range of 32-40. The limit of detection in the studied honey samples was 0.5 μg L‒1. The recovery of the spiked target fungicides at 20, 50, and 100 μg L‒1 were 81.5-116.8 % with the relative standard deviation below 11%. The proposed method is simple, sensitive, less organic solvent consuming, inexpensive, and a rapid procedure for the residue analysis of fungicides in honey samples.

Topics: Chromatography, High Pressure Liquid; Emulsions; Fungicides, Industrial; Honey; Hydrogen-Ion Concentration; Liquid Phase Microextraction; Salicylates; Solvents; Surface-Active Agents

Chemical warfare agents are an actual threat and victims' decontamination is a main concern when mass exposure occurs. Skin decontamination with current protocols has been widely documented, as well as surface decontamination. However, considering hair ability to trap chemicals in vapour phase, we investigated hair decontamination after exposure to sulphur mustard simulants methyl salicylate and 2-chloroethyl ethyl sulphide. Four decontamination protocols were tested on hair, combining showering and emergency decontamination (use of Fuller's earth or Reactive Skin Decontamination Lotion RSDL

Topics: Aluminum Compounds; Chemical Warfare Agents; Decontamination; Gas Chromatography-Mass Spectrometry; Gases; Hair; Magnesium Compounds; Mustard Gas; Salicylates; Silicates; Skin Cream

The main objective of this study was to develop reversed hexagonal (H

Topics: Administration, Cutaneous; Analgesics; Animals; Anti-Inflammatory Agents; Biological Availability; Drug Delivery Systems; Edema; Fatty Alcohols; Female; Liquid Crystals; Male; Mice; Pain; Rats, Wistar; Salicylates; Skin; Skin Absorption; Skin Irritancy Tests

Some herbivore-induced-plant volatiles (HIPVs) compounds are vital for the functioning of an ecosystem, by triggering multi-trophic interactions for natural enemies, plants and herbivores. However, the effect of these chemicals, which play a crucial role in regulating the multi-trophic interactions between plant-herbivore-entomopathogenic fungi, is still unknown. To fill this scientific gap, we therefore investigated how these chemicals influence the entomopathogenic fungi growth and efficacy. In this study, Lipaphis erysimi induced Arabidopsis thaliana HIPVs were collected using headspace system and detected with GC-MS, and then analyzed the effects of these HIPVs chemicals on Lecanicillium lecanii strain V3450. We found that the HIPVs menthol and methyl salicylate at 1 and 10 nmol·ml

Topics: Animals; Aphids; Arabidopsis; Herbivory; Hyphae; Hypocreales; Menthol; Salicylates; Spores, Fungal; Volatile Organic Compounds

The UK's Initial Operational Response (IOR) is a revised process for the medical management of mass casualties potentially contaminated with hazardous materials. A critical element of the IOR is the introduction of immediate, on-scene disrobing and decontamination of casualties to limit the adverse health effects of exposure. Ad hoc cleansing of the skin with dry absorbent materials has previously been identified as a potential means of facilitating emergency decontamination. The purpose of this study was to evaluate the in vitro oil and water absorbency of a range of materials commonly found in the domestic and clinical environments and to determine the effectiveness of a small, but representative selection of such materials in skin decontamination, using an established ex vivo model. Five contaminants were used in the study: methyl salicylate, parathion, diethyl malonate, phorate and potassium cyanide. In vitro measurements of water and oil absorbency did not correlate with ex vivo measurements of skin decontamination. When measured ex vivo, dry decontamination was consistently more effective than a standard wet decontamination method ("rinse-wipe-rinse") for removing liquid contaminants. However, dry decontamination was ineffective against particulate contamination. Collectively, these data confirm that absorbent materials such as wound dressings and tissue paper provide an effective, generic capability for emergency removal of liquid contaminants from the skin surface, but that wet decontamination should be used for non-liquid contaminants.

Topics: Animals; Decontamination; Female; Malonates; Mass Casualty Incidents; Parathion; Phorate; Potassium Cyanide; Salicylates; Skin Absorption; Swine; United Kingdom

The present study showed unique properties of an alkaline, thermophilic lipase of Geobacillus sp. which was isolated from soil of hot spring. The study was aimed to investigate the optimum immobilization conditions of lipase onto silica gel matrix (100-200 mesh) by surface adsorption method and its application in the synthesis of methyl salicylate. Lipase immobilized by surface adsorption onto silica pretreated with 4% glutaraldehyde showed 74.67% binding of protein and the optimum binding time for glutaraldehyde was found to be 2 h. The enzyme showed maximum activity at temperature 55°C, incubation time of 10 min at pH 9.5 of Tris buffer (0.1 M). Free as well as immobilized lipase was more specific to p-NPP (20 mM). All the metal ions and detergents used had inhibitory effect on free as well as immobilized enzyme. The silica immobilized enzyme was reused for hydrolysis and it retained almost 40.78% of its original activity up to 4

Topics: Adsorption; Bacterial Proteins; Esterification; Geobacillus; Glutaral; Lipase; Methanol; Salicylates; Salicylic Acid; Silica Gel; Temperature; Time

There are limited data on modern intermittent hemodialysis (IHD) efficacy on salicylate elimination from topical poisoning.. A 54-year-old male sought treatment for dyspnea but was then diagnosed with salicylate toxicity from topical application of Dencorub Extra Strength Heat Gel® for 1 week. Each tube contained 100 g with 26 % methylsalicylate (26 g). Laboratory workup was remarkable for an elevated anion gap of 30 and salicylate concentration of 78.7 mg/dL [5.7 mmol/L (N < 0.4 mmol/L)]. Treatment with urinary alkalinization was followed by hemodialysis for 5 h. Extraction ratios were 0.44 with clearance rates of 78.5 mL/min. Salicylate concentrations fell rapidly following initiation of hemodialysis with no rebound observed.. Modern high flux IHD is an effective method of removing salicylates in the treatment of chronic topical poisoning.

Topics: Administration, Cutaneous; Antirheumatic Agents; Drug Overdose; Humans; Male; Middle Aged; Renal Dialysis; Respiration Disorders; Salicylates; Treatment Outcome

Rapid decontamination is vital to alleviate adverse health effects following dermal exposure to hazardous materials. There is an abundance of materials and products which can be utilised to remove hazardous materials from the skin. In this study, a total of 15 products were evaluated, 10 of which were commercial or military products and five were novel (molecular imprinted) polymers. The efficacies of these products were evaluated against a 10 µl droplet of (14)C-methyl salicylate applied to the surface of porcine skin mounted on static diffusion cells. The current UK military decontaminant (Fuller's earth) performed well, retaining 83% of the dose over 24 h and served as a benchmark to compare with the other test products. The five most effective test products were Fuller's earth (the current UK military decontaminant), Fast-Act® and three novel polymers [based on itaconic acid, 2-trifluoromethylacrylic acid and N,N-methylenebis(acrylamide)]. Five products (medical moist-free wipes, 5% FloraFree™ solution, normal baby wipes, baby wipes for sensitive skin and Diphotérine™) enhanced the dermal absorption of (14)C-methyl salicylate. Further work is required to establish the performance of the most effective products identified in this study against chemical warfare agents.

Topics: Aluminum Compounds; Animals; Chemical Warfare Agents; Decontamination; Female; In Vitro Techniques; Magnesium Compounds; Molecular Imprinting; Polymers; Salicylates; Silicates; Skin; Skin Absorption; Swine

An amperometric sensor based on a bi-enzyme modified electrode was fabricated to detect methyl salicylate, a volatile organic compound released by pathogen-infected plants via systemic response. The detection is based on cascadic conversion reactions that result in an amperometric electrochemical signal. The bi-enzyme electrode is made of alcohol oxidase and horseradish peroxidase enzymes immobilized on to a carbon nanotube matrix through a molecular tethering method. Methyl salicylate undergoes hydrolysis to form methanol, which is consumed by alcohol oxidase to form formaldehyde while simultaneously reducing oxygen to hydrogen peroxide. The hydrogen peroxide will be further reduced to water by horseradish peroxidase, which results in an amperometric signal via direct electron transfer. The bi-enzyme biosensor was evaluated by cyclic voltammetry and constant potential amperometry using hydrolyzed methyl salicylate as the analyte. The sensitivity of the bi-enzyme biosensor as determined by cyclic voltammetry and constant potential amperometry were 112.37 and 282.82μAcm(-2)mM(-1) respectively, and the corresponding limits of detection were 22.95 and 0.98μM respectively. Constant potential amperometry was also used to evaluate durability, repeatability and interference from other compounds. Wintergreen oil was used for real sample study to establish the application of the bi-enzyme sensor for selective determination of plant pathogen infections.

Topics: Alcohol Oxidoreductases; Biosensing Techniques; Electrochemical Techniques; Electrodes; Enzymes, Immobilized; Equipment Design; Horseradish Peroxidase; Hydrogen Peroxide; Hydrolysis; Nanotubes, Carbon; Oils, Volatile; Pichia; Plant Extracts; Salicylates; Volatilization

The known members of plant methyl esterase (MES) family catalyze the hydrolysis of a C-O ester linkage of methyl esters of several phytohormones including indole-3-acetic acid, salicylic acid and jasmonic acid. The genome of grapevine (Vitis vinifera) was found to contain 15 MES genes, designated VvMES1-15. In this report, VvMES5 was selected for molecular, biochemical and structural studies. VvMES5 is most similar to tomato methyl jasmonate esterase. E. coli-expressed recombinant VvMES5 displayed methyl jasmonate (MeJA) esterase activity, it was renamed VvMJE1. Under steady-state conditions, VvMJE1 exhibited an apparent Km value of 92.9 μM with MeJA. VvMJE1 was also shown to have lower activity with methyl salicylate (MeSA), another known substrate of the MES family, and only at high concentrations of the substrate. To understand the structural basis of VvMJE1 in discriminating MeJA and MeSA, a homolog model of VvMJE1 was made using the X-ray structure of tobacco SABP2, which encodes for methyl salicylate esterase, as a template. Interestingly, two bulky residues at the binding site and near the surface of tobacco SABP2 are replaced by relatively small residues in VvMJE1. Such a change enables the accommodation of a larger substrate MeJA in VvMJE1. The expression of VvMJE1 was compared in control grape plants and grape plants treated with one of the three stresses: heat, cold and UV-B. While the expression of VvMJE1 was not affected by heat treatment, its expression was significantly up-regulated by cold treatment and UV-B treatment. This result suggests that VvMJE1 has a role in response of grape plants to these two abiotic stresses.

Topics: Acetates; Aldehyde-Lyases; Crystallography, X-Ray; Cyclopentanes; Nicotiana; Oxylipins; Plant Proteins; Salicylates; Stress, Physiological; Structural Homology, Protein; Vitis

Occupational exposure to low molecular weight reactive chemicals often leads to development of allergic reactions such as allergic contact dermatitis and respiratory allergies. Further insights into the interaction of these chemicals with physiopathological relevant cellular models might provide the foundations for novel non-animal approaches to safety assessment. In this work we used the human THP-1 cell line to determine phospholipidome changes induced by the skin sensitizer 1-fluoro-2,4-dinitrobenzene (DNFB), the respiratory allergen hexamethylene diisocyanate (HDI), and the irritant methyl salicylate (MESA). We detected that these chemicals differently induce lipid peroxidation and modulate THP-1 IL-1β, IL-12B, IL-8, CD86, and HMOX1 transcription. Decreased phosphatidylethanolamine content was detected in cells exposed to MESA, while profound alterations in the relative abundance of cardiolipin species were observed in cells exposed to DNFB. All chemicals tested induced a decrease in the relative abundance of plasmanyl phosphatidylcholine species PC (O-16:0e/18:1) and phosphatidylinositol species PI (34:1), while increasing PI (38:4). An increased abundance of oleic acid was observed in the phospholipids of cells exposed to DNFB while a decreased abundance of palmitic acid was detected in cells treated with MESA or DNFB. We conclude that both specific and common alterations at phospholipidome levels are triggered by the different chemicals, while not allowing a complete distinction between them using a Canonical Analysis of Principal Coordinates (CAP). The common effects observed at phospholipids level with all the chemicals tested might be related to unspecific cell cytotoxic mechanisms that nevertheless may contribute to the elicitation of specific immune responses. J. Cell. Physiol. 231: 2639-2651, 2016. © 2016 Wiley Periodicals, Inc.

Topics: Cell Line; Chromatography, Liquid; Chromatography, Thin Layer; Dinitrofluorobenzene; Fatty Acids; Humans; Hydrophobic and Hydrophilic Interactions; Irritants; Isocyanates; Lipid Peroxides; Mass Spectrometry; Phospholipids; Principal Component Analysis; Real-Time Polymerase Chain Reaction; Respiration; RNA, Messenger; Salicylates; Skin

Methylsalicylate-containing rubefacients have been reported to cause salicylate poisoning after ingestion, topical application to abnormal skin, and inappropriate topical application to normal skin. Many over-the-counter products contain methylsalicylate. Topical salicylates rarely produce systemic toxicity when used appropriately; however, methylsaliclyate can be absorbed through intact skin. Scrotal skin can have up to 40-fold greater absorption compared to other dermal regions. We report a unique case of salicylate poisoning resulting from the use of a methylsalicylate-containing rubefacient to facilitate masturbation in a male teenager. Saliclyate toxicity has not previously been reported from the genital exposure to methylsaliclyate.

Topics: Adolescent; Humans; Irritants; Male; Masturbation; Nonprescription Drugs; Salicylates; Skin Absorption; Sodium Bicarbonate

Plant defense pathways play a critical role in mediating tritrophic interactions between plants, herbivores, and natural enemies. While the impact of plant defense pathway stimulation on natural enemies has been extensively explored aboveground, belowground ramifications of plant defense pathway stimulation are equally important in regulating subterranean pests and still require more attention. Here we investigate the effect of aboveground stimulation of the salicylic acid pathway through foliar application of the elicitor methyl salicylate on belowground recruitment of the entomopathogenic nematode, Steinernema diaprepesi. Also, we implicate a specific root-derived volatile that attracts S. diaprepesi belowground following aboveground plant stimulation by an elicitor. In four-choice olfactometer assays, citrus plants treated with foliar applications of methyl salicylate recruited S. diaprepesi in the absence of weevil feeding as compared with negative controls. Additionally, analysis of root volatile profiles of citrus plants receiving foliar application of methyl salicylate revealed production of d-limonene, which was absent in negative controls. The entomopathogenic nematode S. diaprepesi was recruited to d-limonene in two-choice olfactometer trials. These results reinforce the critical role of plant defense pathways in mediating tritrophic interactions, suggest a broad role for plant defense pathway signaling belowground, and hint at sophisticated plant responses to pest complexes.

Topics: Animals; Biological Assay; Food Chain; Herbivory; Plant Roots; Rhabditida; Salicylates; Volatile Organic Compounds

Brassica oleracea var. capitata (cabbage) is an important vegetable crop in Asian countries such as Korea, China, and Japan. Cabbage production is severely affected by clubroot disease caused by the soil-borne plant pathogen Plasmodiophora brassicae. During clubroot development, methyl salicylate (MeSA) is biosynthesized from salicylic acid (SA) by methyltransferase. In addition, methyl salicylate esterase (MES) plays a major role in the conversion of MeSA back into free SA. The interrelationship between MES and methytransferases during clubroot development has not been fully explored. To begin to examine these relationships, we investigated the expression of MES genes in disease-susceptible and disease-resistant plants during clubroot development. We identified three MES-encoding genes potentially involved in the defense against pathogen attack. We found that SS1 was upregulated in both the leaves and roots of B. oleracea during P. brassicae infection. These results support the conclusion that SA biosynthesis is suppressed during pathogen infection in resistant plants. We also characterized the expression of a B. oleracea BSMT gene, which appears to be involved in glycosylation rather than MeSA biosynthesis. Our results provide insight into the functions and interactions of genes for MES and methyltransferase during infection. Taken together, our findings indicate that MES genes are important candidates for use to control clubroot diseases.

Topics: Base Sequence; Brassica; Crops, Agricultural; Disease Resistance; Genes, Plant; Host-Parasite Interactions; Methyltransferases; Plant Diseases; Plasmodiophorida; Salicylates; Salicylic Acid

Plant pathogens can manipulate the odor of their host; the odor of an infected plant is often attractive to the plant pathogen vector. It has been suggested that this odor-mediated manipulation attracts vectors and may contribute to spread of disease; however, this requires further broad demonstration among vector-pathogen systems. In addition, disruption of this indirect chemical communication between the pathogen and the vector has not been attempted. We present a model that demonstrates how a phytophathogen (Candidatus Liberibacter asiaticus) can increase its spread by indirectly manipulating the behavior of its vector (Asian citrus psyllid, Diaphorina citri Kuwayama). The model indicates that when vectors are attracted to pathogen-infected hosts, the proportion of infected vectors increases, as well as, the proportion of infected hosts. Additionally, the peak of infected host populations occurs earlier as compared with controls. These changes in disease dynamics were more important during scenarios with higher vector mortality. Subsequently, we conducted a series of experiments to disrupt the behavior of the Asian citrus psyllid. To do so, we exposed the vector to methyl salicylate, the major compound released following host infection with the pathogen. We observed that during exposure or after pre-exposure to methyl salicylate, the host preference can be altered; indeed, the Asian citrus psyllids were unable to select infected hosts over uninfected counterparts. We suggest mechanisms to explain these interactions and potential applications of disrupting herbivore host preference with plant volatiles for sustainable management of insect vectors.

Topics: Animals; Citrus; Dose-Response Relationship, Drug; Hemiptera; Host Specificity; Insect Vectors; Models, Statistical; Pheromones; Plant Diseases; Rhizobiaceae; Salicylates; Volatile Organic Compounds

Fungal infections result in decreases in photosynthesis, induction of stress and signaling volatile emissions and reductions in constitutive volatile emissions, but the way different physiological processes scale with the severity of infection is poorly known. We studied the effects of infection by the obligate biotrophic fungal pathogen Melampsora larici-populina Kleb., the causal agent of poplar leaf rust disease, on photosynthetic characteristics, and constitutive isoprene and induced volatile emissions in leaves of Populus balsamifera var. suaveolens (Fisch.) Loudon. exhibiting different degrees of damage. The degree of fungal damage, quantified by the total area of chlorotic and necrotic leaf areas, varied between 0 (noninfected control) and ∼60%. The rates of all physiological processes scaled quantitatively with the degree of visual damage, but the scaling with damage severity was weaker for photosynthetic characteristics than for constitutive and induced volatile release. Over the whole range of damage severity, the net assimilation rate per area (AA) decreased 1.5-fold, dry mass per unit area 2.4-fold and constitutive isoprene emissions 5-fold, while stomatal conductance increased 1.9-fold and dark respiration rate 1.6-fold. The emissions of key stress and signaling volatiles (methanol, green leaf volatiles, monoterpenes, sesquiterpenes and methyl salicylate) were in most cases nondetectable in noninfested leaves, and increased strongly with increasing the spread of infection. The moderate reduction in AA resulted from the loss of photosynthetically active biomass, but the reduction in constitutive isoprene emissions and the increase in induced volatile emissions primarily reflected changes in the activities of corresponding biochemical pathways. Although all physiological alterations in fungal-infected leaves occurred in a stress severity-dependent manner, modifications in primary and secondary metabolic pathways scaled differently due to contrasting operational mechanisms.

Topics: Adaptation, Physiological; Basidiomycota; Biomass; Butadienes; Hemiterpenes; Metabolic Networks and Pathways; Methanol; Pentanes; Photosynthesis; Plant Diseases; Plant Leaves; Populus; Salicylates; Signal Transduction; Stress, Physiological; Terpenes; Trees; Volatile Organic Compounds

Following a supramolecular synthon approach, simple salt formation has been employed to gain access to a series of supramolecular gelators derived from the well-known non-steroidal anti-inflammatory drug (NSAID) ibuprofen. A well-studied gel-inducing supramolecular synthon, namely primary ammonium monocarboxylate (PAM), has been exploited to generate a series of PAM salts by reacting ibuprofen with various primary amines. Remarkably, all of the salts (S1-S7) thus synthesized proved to be good to moderate gelators of various polar and nonpolar solvents. Single-crystal and powder X-ray diffraction studies established the existence of the PAM synthons in the gel network, confirming the efficacy of the supramolecular synthon approach employed. Most importantly, the majority of the salts (S2, S3, S6, and S7) were capable of gelling methyl salicylate (MS), an important ingredient found in many commercial topical gels. In vitro experiments (MTT and PGE2 assays) revealed that all of the salts (except S3 and S7) were biocompatible (up to 0.5 mm concentration), and the most suited one, S6, displayed anti-inflammatory ability as good as that of the parent drug ibuprofen. A topical gel of S6 with methyl salicylate and menthol was found to be suitable for delivering the gelator drug in a self-delivery fashion in treating skin inflammation in mice. Histological studies, including immunohistology, were performed to further probe the role of the gelator drug S6 in treating inflammation. Cell imaging studies supported cellular uptake of the gelator drug in such biomedical application.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Cell Survival; Drug Carriers; Gels; Ibuprofen; Male; Menthol; Mice; Mice, Inbred BALB C; Microscopy, Fluorescence; Molecular Conformation; RAW 264.7 Cells; Salicylates; Skin; Skin Diseases; Spectroscopy, Fourier Transform Infrared; X-Ray Diffraction

Volatile organic compounds have been recognized as important marker chemicals to detect plant diseases caused by pathogens. Methyl salicylate has been identified as one of the most important volatile organic compounds released by plants during a biotic stress event such as fungal pathogen infection. Advanced detection of these marker chemicals could help in early identification of plant diseases and has huge significance for agricultural industry. This work describes the development of a novel bi-enzyme based electrochemical biosensor consisting of salicylate hydroxylase and tyrosinase enzymes immobilized on carbon nanotube modified electrodes. The amperometric detection using the bi-enzyme platform was realized through a series of cascade reactions that terminate in an electrochemical reduction reaction. Electrochemical measurements revealed that the sensitivity of the bi-enzyme sensor was 30.6±2.7µAcm(-2)µM(-1) and the limit of detection and limit of quantification were 13nM (1.80ppb) and 39nM (5.39ppb) respectively. Interference studies showed no significant interference from the other common plant volatile compounds. Synthetic analyte studies revealed that the bi-enzyme based biosensor can be used to reliably detect methyl salicylate released by unhealthy plants.

Topics: Agaricales; Biosensing Techniques; Cloning, Molecular; Electrochemical Techniques; Enzymes, Immobilized; Escherichia coli; Limit of Detection; Mixed Function Oxygenases; Models, Molecular; Monophenol Monooxygenase; Nanotubes, Carbon; Plants; Pseudomonas putida; Recombinant Proteins; Salicylates; Transducers

Both molecular and crystal-engineering approaches were exploited to synthesize a new class of multidrug-containing supramolecular gelators. A well-known nonsteroidal anti-inflammatory drug, namely, indomethacin, was conjugated with six different l-amino acids to generate the corresponding peptides having free carboxylic acid functionality, which reacted further with an antiviral drug, namely, amantadine, a primary amine, in 1:1 ratio to yield six primary ammonium monocarboxylate salts. Half of the synthesized salts showed gelation ability that included hydrogelation, organogelation and ambidextrous gelation. The gels were characterized by table-top and dynamic rheology and different microscopic techniques. Further insights into the gelation mechanism were obtained by temperature-dependent

Topics: Anti-Inflammatory Agents, Non-Steroidal; Drug Delivery Systems; Gels; Indomethacin; Rheology; Salicylates; Salts; Solvents; Spectroscopy, Fourier Transform Infrared; Water

Methyl salicylate (MeSA) is a volatile organic compound synthesized from salicylic acid (SA) a plant hormone that helps to fight against plant disease. Seed treatment with MeSA, is an encouraging method to the seed industry to produce more growth and yield. The aim of our study is to find out the growth, development and disease tolerance of rice seed treated with different concentrations of MeSA. Also the seed treatments were studied to determine whether they directly influenced seedling emergence and growth in rice (Oryza sativa L) cultivars 'IR 20, IR 50, IR 64, ASD 16, ASD 19 and ADT 46' under greenhouse condition. MeSA seed treatments at 25, 50, 75 and 100 mg/L significantly increased seedling emergence. Effects were stronger in IR 50, and IR 64 and the effects were dose dependent, although the relationship between dose and effect was not always linear. MeSA seed treated rice plant against bacterial blight were analyzed. Bacterial blight was more effectively controlled by the seed treated with 100 mg/L than others. These results suggest that seed treatment with MeSA alters plant physiology in ways that may be useful for crop production as well as protection.

Topics: Bacterial Infections; Disease Resistance; Germination; Oryza; Plant Diseases; Plant Growth Regulators; Salicylates; Seeds

Topics: Animals; Autoantibodies; Cytokines; Disease Progression; Female; Glycosides; Inflammation; Lupus Erythematosus, Systemic; Mice; Mice, Inbred BALB C; Salicylates; Signal Transduction; Terpenes

Plant defense pathways mediate multitrophic interactions above and belowground. Understanding the effects of these pathways on pests and natural enemies above and belowground holds great potential for designing effective control strategies. Here we investigate the effects of aboveground stimulation of plant defense pathways on the interactions between corn, the aboveground herbivore adult Diabrotica speciosa, the belowground herbivore larval D. speciosa, and the subterranean ento-mopathogenic nematode natural enemy Heterorhabditis amazonensis. We show that adult D. speciosa recruit to aboveground herbivory and methyl salicylate treatment, that larval D. speciosa are relatively indiscriminate, and that H. amazonensis en-tomopathogenic nematodes recruit to corn fed upon by adult D. speciosa. These results suggest that entomopathogenicnematodes belowground can be highly attuned to changes in the aboveground parts of plants and that biological control can be enhanced with induced plant defense in this and similar systems.

Topics: Animals; Biological Control Agents; Coleoptera; Herbivory; Larva; Nematoda; Predatory Behavior; Salicylates; Zea mays

In this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. The in vivo anti-inflammatory activities of target compounds were investigated against xylol-induced ear edema and carrageenan-induced paw edema in mice. The results showed that all synthesized compounds exhibited potent anti-inflammatory activities. Especially, the anti-inflammatory activities of compounds

Topics: Animals; Anti-Inflammatory Agents; Carrageenan; Cyclooxygenase 2; Cytokines; Disease Models, Animal; Edema; Gene Expression Regulation; Lipopolysaccharides; Mice; Molecular Structure; Piperazine; Piperazines; RAW 264.7 Cells; Salicylates; Xylenes

In this paper, we propose a new and complete mechanism for dual fluorescence of methyl salicylate (MS) under different conditions using a combined experimental (i.e., steady-state absorption and emission spectra and time-resolved fluorescence spectra) and theoretical (i.e., time-dependent density function theory) study. First, our theoretical study indicates that the barrier height for excited state intramolecular proton transfer (ESIPT) reaction of ketoB depends on the solvent polarity. In nonpolar solvents, the ESIPT reaction of ketoB is barrierless; the barrier height will increase with increasing solvent polarity. Second, we found that, in alcoholic solvents, intermolecular hydrogen bonding plays a more important role. The ketoB form of MS can form two hydrogen bonds with alcoholic solvents; one will facilitate ESIPT and produce the emission band in the blue region; the other one precludes ESIPT and produces the emission band in the near-UV region. Our proposed new mechanism can well explain previous results as well as our new experimental results.

Topics: Absorption, Physicochemical; Alcohols; Hydrogen Bonding; Models, Molecular; Salicylates; Solvents; Spectrometry, Fluorescence

The fluorescent behavior of the methyl-5-R-salicylates is analyzed in media of negligible acidity and basicity so that the methyl-5-R-salicylates may undergo solvent dipolarity changes or not in a controlled manner based on the following guidelines: (i) The molecular forms of these methyl-5-R-salicylates possessing an intramolecular hydrogen bond (IMHB) between their hydroxyl group and ether type oxygen (rotated tautomer) undergo no excited-state intramolecular proton transfer (ESIPT) in their first excited electronic state; (ii) on the other hand, the molecular species with an IMHB between its hydroxyl group and carbonyl oxygen (normal tautomer) exhibits both ESIPT and normal emission when charge transfer (CT) from the R-substituent to the phenol group is slight to moderate, but only normal emission is monitored when CT is strong. The special insensitivity of the first UV absorption band for the normal tautomer of methylsalicylate (MS, with R = H) to the polarity of the solvent is not echoed by the normal forms of methyl-5-R-salicylates containing substituents R with a substantial effect of CT in the IMHB of the compound. These solvatochromic features of MS are shared by the emissions of its derivatives. The photophysical evidence found for the methyl-5-R-salicylates confirms the photophysical model recently reported (Phys. Chem. Chem. Phys. 2012, 14, 8903-8909), which assigns three fluorescent emissions to the methyl-5-R-salicylates: two of them coming from the IMHB normal tautomer, which undergoes ESIPT, and another from the IMHB rotated tautomer, which cannot undergo ESIPT.

Topics: Absorption, Physicochemical; Electron Transport; Hydrogen Bonding; Protons; Quantum Theory; Salicylates

Bacillus subtilis is a rhizobacterium that promotes plant growth and health. Cultivation of B. subtilis with an uprooted weed on solid medium produced pleat-like architectures on colonies near the plant. To test whether plants emit signals that affect B. subtilis colony morphology, we examined the effect of plant-related compounds on colony morphology. Bacillus subtilis formed mucoid colonies specifically in response to methyl salicylate, which is a plant-defense signal released in response to pathogen infection. Methyl salicylate induced mucoid colony formation by stimulating poly-γ-glutamic acid biosynthesis, which formed enclosing capsules that protected the cells from exposure to antimicrobial compounds. Poly-γ-glutamic acid synthesis depended on the DegS-DegU two-component regulatory system, which activated DegSU-dependent gene transcription in response to methyl salicylate. Bacillus subtilis did not induce plant methyl salicylate production, indicating that the most probable source of methyl salicylate in the rhizosphere is pathogen-infected plants. Methyl salicylate induced B. subtilis biosynthesis of the antibiotics bacilysin and fengycin, the latter of which exhibited inhibitory activity against the plant pathogenic fungus Fusarium oxysporum. We propose that B. subtilis may sense plants under pathogen attack via methyl salicylate, and express defense responses that protect both B. subtilis and host plants in the rhizosphere.

Topics: Anti-Bacterial Agents; Bacillus subtilis; Fusarium; Plant Diseases; Plants; Polyglutamic Acid; Rhizosphere; Salicylates

Vegetation emits a class of oxygenated hydrocarbons--the green leaf volatiles (GLVs)--under stress or damage. Under foggy conditions GLVs might be a source of secondary organic aerosol (SOA) via aqueous reactions with hydroxyl radical (OH), singlet oxygen ((1)O2*), and excited triplet states ((3)C*). To examine this, we determined the aqueous kinetics and SOA mass yields for reactions of (3)C* and (1)O2* with five GLVs: methyl jasmonate (MeJa), methyl salicylate (MeSa), cis-3-hexenyl acetate (HxAc), cis-3-hexen-1-ol (HxO), and 2-methyl-3-butene-2-ol (MBO). Second-order rate constants with (3)C* and (1)O2* range from (0.13-22) × 10(8) M(-1) s(-1) and (8.2-60) × 10(5) M(-1) s(-1) at 298 K, respectively. Rate constants with (3)C* are independent of temperature, while values with (1)O2* show significant temperature dependence (Ea = 20-96 kJ mol(-1)). Aqueous SOA mass yields for oxidation by (3)C* are (84 ± 7)%, (80 ± 9)%, and (38 ± 18)%, for MeJa, MeSa, and HxAc, respectively; we did not measure yields for other conditions because of slow kinetics. The aqueous production of SOA from GLVs is dominated by (3)C* and OH reactions, which form low volatility products at a rate that is approximately half that from the parallel gas-phase reactions of GLVs.

Topics: Acetates; Aerosols; Cyclopentanes; Hexanols; Hydroxyl Radical; Kinetics; Oxygen; Oxylipins; Pentanols; Plant Leaves; Salicylates; Singlet Oxygen; Temperature; Volatile Organic Compounds; Volatilization; Water

In the last decade plant-to-plant communication has received an increasing attention, particularly for the role of Volatile Organic Compounds as possible elicitors of plant defense. The role of β-ocimene as an interspecific elicitor of plant defense has been recently assessed in multitrophic systems including different plant species (Solanaceae, Poaceae, legumes) and different pest species including chewer insects and phytophagous mites. Both chewer insects and phytophagous mites are known to elicit specific plant defensive pathways which are different (at least in part) from those elicited by sap feeders. The aim of this research was to fill this gap of knowledge and to assess the role of β-ocimene as an elicitor of plant defense against aphid pests, which are sap feeders. For this purpose we used as transgenic tobacco plant releasing an odour plume enriched in this compound as emitter and a tomato plant as receiver. We selected the aphid Macrosiphum euphorbiae and its natural enemy, the parasitoid Aphidius ervi, as the targets of plant induced defense. Tomato plant defense induced by β-ocimene was assessed by characterizing the aphid performance in terms of fixing behaviour, development and reproduction (direct plant defense) and the parasitoid performance in terms of attraction towards tomato plants (indirect plant defense). The characterization of tomato response to β-ocimene was completed by the identification of Volatile Organic Compounds as released by conditioned tomato plants. Tomato plants that were exposed to the volatiles of transgenic tobacco enriched in β-ocimene resulted in less suitable for the aphids in respect to control ones (direct defense). On tomato plants "elicited" by β-ocimene we recorded: a significant lower number of aphids settled; a significant lower number newborn nymphs; a significant lower weight of aphids feeding. In addition, tomato plants "elicited" by β-ocimene resulted became more attractive towards the parasitoid A. ervi than control ones. These results could be explained at least in part by examining the composition of the Volatile Organic Compounds released by tomato plants "elicited" by β-ocimene. Indeed, we found a significantly higher release of several compounds including methyl salicylate and cis-3-hexen-1-ol. These two compounds have been demonstrated to impair aphid development and reproduction and to be involved in the attraction of the aphid parasitoid A. ervi. By considering the ubiquity of β-ocimene and i

Topics: Acyclic Monoterpenes; Alkenes; Animals; Aphids; Gene Expression; Hexanols; Host-Parasite Interactions; Nicotiana; Plant Immunity; Plants, Genetically Modified; Salicylates; Solanum lycopersicum; Volatile Organic Compounds

Methyl salicylate (MeSa) is a stress hormone released by plants under attack by pathogens or herbivores . MeSa has been shown to attract predatory insects of herbivores and repel pests. The molecules and neurons underlying animal response to MeSa are not known. Here we found that the nematode Caenorhabditis elegans exhibits a strong avoidance response to MeSa, which requires the activities of two closely related neuropeptide receptors NPR-1 and NPR-2. Molecular analyses suggest that NPR-1 expressed in the RMG inter/motor neurons is required for MeSa avoidance. An NPR-1 ligand FLP-18 is also required. Using a rescuing npr-2 promoter to drive a GFP transgene, we identified that NPR-2 is expressed in multiple sensory and interneurons. Genetic rescue experiments suggest that NPR-2 expressed in the AIZ interneurons is required for MeSa avoidance. We also provide evidence that the AWB sensory neurons might act upstream of RMGs and AIZs to detect MeSa. Our results suggest that NPR-2 has an important role in regulating animal behavior and that NPR-1 and NPR-2 act on distinct interneurons to affect C. elegans avoidance response to MeSa.

Topics: Animals; Behavior, Animal; Caenorhabditis elegans; Caenorhabditis elegans Proteins; Gene Expression Profiling; Gene Expression Regulation; Interneurons; Male; Neurons; Plant Growth Regulators; Salicylates; Sensory Receptor Cells; Stress, Physiological

Withania somnifera, known in India as Asghawhanda, is used traditionally to treat many medical problems including diabetes and has demonstrated therapeutic activity in various animal models as well as in diabetic patients. While much of W. somnifera's therapeutic activity is attributed to withanolides, their role in the anti-diabetic activity of W. somnifera has not been adequately studied. In the present study, we evaluated the anti-diabetic activity of W. somnifera extract and purified withanolides, as well as the effect of various elicitors on this activity. W. somnifera leaf and root extracts increased glucose uptake in myotubes and adipocytes in a dose dependent manner, with the leaf extract more active than the root extract. Leaf but not root extract increased insulin secretion in basal pancreatic beta cells but not in stimulated cells. Six withanolides isolated from W. somnifera were tested for anti-diabetic activity based on glucose uptake in skeletal myotubes. Withaferin A was found to increase glucose uptake, with 10μM producing a 54% increase compared with control, suggesting that withaferin A is at least partially responsible for W. somnifera's anti-diabetic activity. Elicitors applied to the root growing solutions affected the physiological state of the plants, altering membrane leakage or osmotic potential. Methyl salicylate and chitosan increased withaferin A content by 75% and 69% respectively, and extracts from elicited plants increased glucose uptake to a higher extent than non-elicited plants, demonstrating a correlation between increased content of withaferin A and anti-diabetic activity.

Topics: 4-Chloro-7-nitrobenzofurazan; Animals; Chitosan; Deoxyglucose; Dose-Response Relationship, Drug; Humans; Hypoglycemic Agents; India; Israel; Molecular Structure; Salicylates; Withania; Withanolides

Host-guest complexation of dapoxyl sodium sulphonate (DSS), an intramolecular charge transfer dye with water-soluble and non-toxic macrocycle γ-cyclodextrin (γ-CD), has been investigated in a wide pH range. Steady-state absorption, fluorescence and time-resolved fluorescence measurements confirm the positioning of DSS into the hydrophobic cavity of γ-CD. A large fluorescence enhancement ca. 30 times, due to 1 : 2 complex formation and host-assisted guest-protonation have been utilised for developing a method for the utilisation of CD based drug-delivery applications. A simple fluorescence-displacement based approach is implemented at physiological pH for the assessment of binding strength of pharmaceutically useful small drug molecules (ibuprofen, paracetamol, methyl salicylate, salicylic acid, aspirin, and piroxicam) and six important antibiotic drugs (resazurin, thiamphenicol, chloramphenicol, ampicillin, kanamycin, and sorbic acid) with γ-CD.

Topics: Acetaminophen; Ampicillin; Aspirin; beta-Cyclodextrins; Binding Sites; Chloramphenicol; Drug Delivery Systems; Fluorescence; Fluorescent Dyes; Fluorometry; Hydrogen-Ion Concentration; Ibuprofen; Kanamycin; Oxazines; Oxazoles; Piroxicam; Salicylates; Salicylic Acid; Sorbic Acid; Sulfonamides; Thiamphenicol; Xanthenes

There are various techniques to study root canal morphology and diaphonization is one of them. There are various methods of decalcification and diaphonization, cited in literature and the main aim of this paper was to give a brief account of the various techniques and share our experience of the technique at a teaching institution in Karachi, Pakistan.. Diaphonization is one of the oldest methods and is based on decalcification of teeth followed by clearing and dye penetration. The specimen is later studied under microscope without sectioning.. After the process of clearing a three-dimensional (3D) structure of the internal canal anatomy was visible with naked eye.. This paper entails a detailed historical background as well as the author's technique including percentages of various chemicals used and the timing of immersion of teeth into these agents.. The read out is simple and can be subjected to interpretation by direct observation under microscope and can be helpful for students undertaking research in not only the discipline of dentistry but also in other fields such as botany and zoology.

Topics: 2-Propanol; Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Fixatives; Humans; Nitric Acid; Salicylates; Time Factors; Tissue Fixation; Xylenes

Topics: Administration, Topical; Antirheumatic Agents; Dyspnea; Humans; Male; Middle Aged; Salicylates

Listerine® is one of the most popular mouthwashes worldwide and claims to combat harmful bacteria. In the past century, its recipe was changed from an essential oil mouthwash to a five-component mixture (thymol, menthol, eucalyptol, and methyl salicylate dissolved in 27% ethanol). The aim of this study was to get preliminary information about the antimicrobial activities of individual Listerine® components and their mixtures. We tested the bacterial strains Streptococcus mutans, Enterococcus faecalis, and Eikenella corrodens and the yeast Candida albicans. The established minimum inhibitory concentration (MIC) assay and the minimum bactericidal/fungicidal concentration (MBC/MFC) assay were applied. None of the combinations of two phenols at the concentrations contained within Listerine® were associated with either an additive or synergistic effect. Thymol had lower MIC and MBC/MFC values than the other Listerine® components and Listerine® against E. corrodens and C. albicans. The mixtures consisting of eucalyptol, methyl salicylate, and thymol were the most effective against S. mutans and E. faecalis and more effective than Listerine®. Our results demonstrate that the phenols and their concentrations as contained within Listerine® could be further optimized in terms of selecting those which increase their general effectiveness, at concentrations that do not induce harm.

Topics: Anti-Infective Agents; Candida albicans; Cyclohexanols; Drug Combinations; Enterococcus faecalis; Eucalyptol; Microbial Sensitivity Tests; Monoterpenes; Mouthwashes; Oils, Volatile; Salicylates; Streptococcus mutans; Terpenes; Thymol

Topics: Accidents; Adult; Fatal Outcome; Humans; Male; Oils, Volatile; Plant Extracts; Renal Dialysis; Salicylates

Olfaction is crucial for short distance host location and pheromone detection by insects. Complexes of olfactory receptors (ORs) are composed of odor-specific ORs and OR co-receptors (Orco). Orcos are widely co-expressed with odor-specific ORs and are conserved across insect taxa. A number of Orco orthologs have been studied to date, although none has been identified in cereal aphids. In this study, an Orco gene ortholog was cloned from the grain aphid, Sitobion avenae, and named "SaveOrco"; RNA interference (RNAi) reduced the expression of SaveOrco to 34.11% in aphids, resulting in weaker EAG (electroantennogram) responses to plant volatiles (Z-3-hexene-1-ol; methyl salicylate, MeSA) and aphid alarm pheromone (E-β-farnesene, EBF). Aphid wing differentiation induced by EBF was investigated in both RNAi treated and untreated aphids. EBF induced production of winged aphids in both pre-natal and post-natal periods in untreated aphids, but no such induction was observed in the RNAi-treated aphids. We conclude that SaveOrco is crucial for the aphid's response to pheromones and other volatiles, and is involved in wing differentiation triggered by EBF.

Topics: Animals; Aphids; Arthropod Antennae; Electrophysiological Phenomena; Hexanols; Pheromones; Receptors, Odorant; RNA Interference; Salicylates; Sesquiterpenes; Wings, Animal

Although one of an enzyme's hallmarks is the high specificity for their natural substrates, substrate promiscuity has been reported more frequently. It is known that promiscuous enzymes generally show different catalytic efficiencies to different substrates, but our understanding of the origin of such differences is still lacking. Here we report the results of quantum mechanical/molecular mechanical simulations and an experimental study of salicylic acid binding protein 2 (SABP2). SABP2 has promiscuous esterase activity toward a series of substrates but shows a high activity toward its natural substrate, methyl salicylate (MeSA). Our results demonstrate that this enzyme may use substrate-assisted catalysis involving the hydroxyl group from MeSA to enhance the activity and achieve substrate discrimination.

Topics: Acylation; Catalysis; Catalytic Domain; Crystallography, X-Ray; Esterases; Models, Molecular; Molecular Dynamics Simulation; Nicotiana; Plant Proteins; Salicylates; Substrate Specificity

Traps suitable for catching female Agriotes click beetles may provide better reconnaissance than pheromone-baited traps which catch only males, thereby contributing to more efficient crop protection. The basis for this study came from (i) observations of female Agriotes brevis (Candeze) aggregating beneath foliage of Medicago sativa (L.) and Lolium italicum (A. Br.) placed on plastic sheets on bare soil, and (ii) field tests demonstrating attraction of females to traps baited with foliage from these plants. The aim was to identify and field test volatile compounds from M. sativa and L. italicum leaves.. A number of electrophysiologically active chemicals were identified from headspace extracts of M. sativa and L. italicum. Three different synthetic blends of the identified compounds, comprising four, seven and nine components, were field tested. The four- and nine-component blends caught more female A. brevis than unbaited traps, with the proportion of females not differing between blends.. The plant-derived blends were shown to catch female A. brevis under field conditions when applied in traps. Of these, the four-component blend, given its relatively simple composition [(Z)-3-hexenyl acetate:methyl benzoate:(Z)-3-hexen-1-ol:methyl salicylate 300:5:30:30 mg bait(-1)], may be a suitable 'standard' blend for bait optimisation.

Topics: Acetates; Animals; Arthropod Antennae; Behavior, Animal; Coleoptera; Female; Hexanols; Italy; Lolium; Medicago sativa; Pheromones; Plant Leaves; Salicylates; Volatile Organic Compounds

To develop and characterize a salicylate resin with potential use in bioactive endodontic sealers.. Methyl salicylate, glycerol and titanium isopropoxide were added in a closed system for the transesterification reaction. The resin obtained was characterized by proton nuclear magnetic resonance spectroscopy (1H NMR) and size exclusion chromatography (SEC). To verify the applicability of the resin to the development of endodontic sealers, experimental cements were prepared by mixing glycerol salicylate resin, calcium hydroxide and methyl salicylate in the ratios of 2 : 1 : 1, 1 : 2 : 1, 1 : 1 : 2, 1 : 1 : 1, 4 : 1 : 1, 1 : 4 : 1 and 1 : 1 : 4. Setting times were measured according to ISO 6876. Features of the hardening reaction were described by micro-RAMAN spectroscopy.. The transesterification reaction had a 72% efficiency. The (1) H NMR analysis revealed the presence of the expected functional groups (hydroxyls and aromatic rings), and the SEC confirmed the molar mass of the resin produced. The setting times of experimental sealers ranged from 70 min (ratio 1 : 1 : 1) to 490 min (ratio 1 : 1 : 4). The conversion of the salicylic groups (1 613 cm(-1) ) to salicylate salt (1 543 cm(-1) ) and the reduction in calcium hydroxide peaks (1084 and 682 cm(-1) ) were confirmed by micro-RAMAN spectroscopy, which showed the calcium chelation by the resin.. The new glycerol salicylate resin was successfully synthesized and revealed a potential application in the development of endodontic sealers.

Topics: Calcium Hydroxide; Glycerol; Magnetic Resonance Spectroscopy; Materials Testing; Organometallic Compounds; Resin Cements; Root Canal Filling Materials; Salicylates

The radical cation generated during photobleaching of β-carotene is scavenged efficiently by the anion of methyl salicylate from wintergreen oil in a second-order reaction approaching the diffusion limit with k2 = 3.2 × 10(9) L mol(-1) s(-1) in 9 : 1 v/v chloroform-methanol at 23 °C, less efficiently by the anion of salicylic acid with 2.2 × 10(8) L mol(-1) s(-1), but still of possible importance for light-exposed tissue. Surprisingly, acetylsalicylate, the aspirin anion, reacts with an intermediate rate in a reaction assigned to the anion of the mixed acetic-salicylic acid anhydride formed through base induced rearrangements. The relative scavenging rate of the β-carotene radical cation by the three salicylates is supported by DFT-calculations.

Topics: Anti-Inflammatory Agents; beta Carotene; Free Radical Scavengers; Free Radicals; Kinetics; Oils, Volatile; Plant Extracts; Salicylates

The equilibrium geometries, IR-spectra and transition mechanism of intramolecular hydrogen-bonded methyl salicylate in excited state were studied using DFT and TDDFT with 6-31++G (d, p) basis set. The length of hydrogen bond OH⋯OC is decreased from 1.73 Å in the ground state to 1.41 and 1.69 Å in the excited S1 and S3 states. The increase of bond length for HO and CO group also indicates that in excited state the hydrogen bond OH⋯OC is strengthened. IR spectra show HO and CO stretching bands are strongly redshifted by 1387 and 67 cm(-1) in the excited S1 and S3 states comparing to the ground state. The excitation energy and the absorption spectrum show the S3 state is the main excited state of the low-lying excited states. By analyzing the frontier molecular orbitals, the transition from the ground state to the excited S1 and S3 states was predicted to be the π→π∗ mode.

Topics: Electrons; Hydrogen Bonding; Models, Molecular; Photochemical Processes; Quantum Theory; Salicylates; Spectrophotometry, Infrared

Systemic resistance is induced by pathogens and confers protection against a broad range of pathogens. Recent studies have indicated that salicylic acid (SA) derivative methyl salicylate (MeSA) serves as a long-distance phloem-mobile systemic resistance signal in tobacco, Arabidopsis, and potato. However, other experiments indicate that jasmonic acid (JA) is a critical mobile signal. Here, we present evidence suggesting both MeSA and methyl jasmonate (MeJA) are essential for systemic resistance against Tobacco mosaic virus (TMV), possibly acting as the initiating signals for systemic resistance. Foliar application of JA followed by SA triggered the strongest systemic resistance against TMV. Furthermore, we use a virus-induced gene-silencing-based genetics approach to investigate the function of JA and SA biosynthesis or signaling genes in systemic response against TMV infection. Silencing of SA or JA biosynthetic and signaling genes in Nicotiana benthamiana plants increased susceptibility to TMV. Genetic experiments also proved the irreplaceable roles of MeSA and MeJA in systemic resistance response. Systemic resistance was compromised when SA methyl transferase or JA carboxyl methyltransferase, which are required for MeSA and MeJA formation, respectively, were silenced. Moreover, high-performance liquid chromatography-mass spectrometry analysis indicated that JA and MeJA accumulated in phloem exudates of leaves at early stages and SA and MeSA accumulated at later stages, after TMV infection. Our data also indicated that JA and MeJA could regulate MeSA and SA production. Taken together, our results demonstrate that (Me)JA and (Me)SA are required for systemic resistance response against TMV.

Topics: Acetates; Cyclopentanes; Disease Resistance; Gene Expression Regulation, Plant; Gene Silencing; Genes, Reporter; Nicotiana; Oxylipins; Phloem; Plant Diseases; Plant Growth Regulators; Plant Leaves; Plant Proteins; Plants, Genetically Modified; Salicylates; Salicylic Acid; Signal Transduction; Tobacco Mosaic Virus

Ambient desorption/ionization mass spectrometry (ADI-MS) has developed into an important analytical field over the last 9 years. The ability to analyze samples under ambient conditions while retaining the sensitivity and specificity of mass spectrometry has led to numerous applications and a corresponding jump in the popularity of this field. Despite the great potential of ADI-MS, problems remain in the areas of ion identification and quantification. Difficulties with ion identification can be solved through modified instrumentation, including accurate-mass or MS/MS capabilities for analyte identification. More difficult problems include quantification because of the ambient nature of the sampling process. To characterize and improve sample volatilization, ionization, and introduction into the mass spectrometer interface, a method of visualizing mass transport into the mass spectrometer is needed. Schlieren imaging is a well-established technique that renders small changes in refractive index visible. Here, schlieren imaging was used to visualize helium flow from a plasma-based ADI-MS source into a mass spectrometer while ion signals were recorded. Optimal sample positions for melting-point capillary and transmission-mode (stainless steel mesh) introduction were found to be near (within 1 mm of) the mass spectrometer inlet. Additionally, the orientation of the sampled surface plays a significant role. More efficient mass transport resulted for analyte deposits directly facing the MS inlet. Different surfaces (glass slide and rough surface) were also examined; for both it was found that the optimal position is immediately beneath the MS inlet.

Topics: Air; Atmospheric Pressure; Caffeine; Environmental Monitoring; Helium; Mass Spectrometry; Models, Chemical; Reproducibility of Results; Salicylates; Surface Properties; Volatilization

Chemical warfare agents (CWA) are highly toxic compounds which have been produced to kill or hurt people during conflicts or terrorist attacks. Despite the fact that their use is strictly prohibited according to international convention, populations' exposure still recently occurred. Development of markers of exposure to CWA is necessary to distinguish exposed victims from unexposed ones. We present the first study of hair usage as passive sampler to assess contamination by chemicals in vapour form. This work presents more particularly the hair adsorption capacity for methyl salicylate used as a surrogate of the vesicant sulphur mustard. Chemical vapours toxicity through the respiratory route has historically been defined through Haber's law's concentration-time (Ct) product, and vapour exposure of hair to methyl salicylate was conducted with various times or doses of exposure in the range of incapacitating and lethal Ct products corresponding to sulphur mustard. Following exposure, extraction of methyl salicylate from hair was conducted by simple soaking in dichloromethane. Methyl salicylate could be detected on hair for vapour concentration corresponding to about one fifth of the sulphur mustard concentration that would kill 50% of exposed individuals (LCt50). The amount of methyl salicylate recovered from hair increased with time or dose of exposure. It showed a good correlation with the concentration-time product, suggesting that hair could be used like a passive sampler to assess vapour exposure to chemical compounds. It introduces great perspectives concerning the use of hair as a marker of exposure to CWA.

Topics: Chemical Warfare Agents; Environmental Exposure; Gases; Hair; Humans; Mustard Gas; Salicylates; Time Factors

Laser speckle imaging with long exposure time has been applied noninvasively to visualize the immediate reaction of cutaneous vessels in mice in response to a known primary irritant and potential allergen—methyl salicylate. The compound has been used topically on the surface of the pinna and the reaction of the vascular network was examined. We demonstrate that irritant-induced acute vascular reaction can be effectively and accurately detected by laser speckle imaging technique. The current approach holds a great promise for application in routine screening of the cutaneous vascular response induced by contact agents, screenings of mouse ear swelling test, and testing the allergenic potential of new synthetic materials and healthcare pharmaceutical products.

Topics: Allergens; Animals; Diagnostic Imaging; Ear, External; Edema; Lasers; Mice; Salicylates

Plants attacked by herbivores have evolved different strategies that fend off their enemies. Insect eggs deposited on leaves have been shown to inhibit further oviposition through visual or chemical cues. In some plant species, the volatile methyl salicylate (MeSA) repels gravid insects but whether it plays the same role in the model species Arabidopsis thaliana is currently unknown. Here we showed that Pieris brassicae butterflies laid fewer eggs on Arabidopsis plants that were next to a MeSA dispenser or on plants with constitutively high MeSA emission than on control plants. Surprisingly, the MeSA biosynthesis mutant bsmt1-1 treated with egg extract was still repellent to butterflies when compared to untreated bsmt1-1. Moreover, the expression of BSMT1 was not enhanced by egg extract treatment but was induced by herbivory. Altogether, these results provide evidence that the deterring activity of eggs on gravid butterflies is independent of MeSA emission in Arabidopsis, and that MeSA might rather serve as a deterrent in plants challenged by feeding larvae.

Topics: Animals; Arabidopsis; Arabidopsis Proteins; Butterflies; Female; Herbivory; Larva; Male; Methyltransferases; Mutation; Oviposition; Ovum; RNA, Messenger; Salicylates

The purpose of this study was to study the root canal morphology of South Asian Indian mandibular premolars using a tooth clearing technique.. Two hundred mandibular premolar teeth were collected from different dental schools and clinics in India. After pulp tissue removal and root canal staining with Indian ink, the specimens were decalcified with 5% nitric acid, dehydrated in ethyl alcohol, and subsequently cleared in methyl salicylate.. Of the 200 mandibular premolars, 100 were first premolars and 100 were second premolars. Of the first premolars, 94% had a single root, whereas 6% were 2 rooted. Seventy-six percent had a single canal, 22% had 2 canals, and 2% had 3 canals. Eighty-two percent had a single apical foramen, 16% had 2 foramens, and 2% teeth had 3 apical foramens. Eighty percent of teeth had type I, 6% had type II, 10% had type IV, 2% had type V, and 2% teeth had type IX root canal anatomy. Of the 100 second premolars, 92% had a single root, whereas 8% teeth were 2 rooted and fused. Fifty-eight percent of teeth had a single canal, and 42% had two canals. Eighty-eight percent had a single apical foramen, and 12% had 2 foramens. Sixty-six percent had type I, 30% had type II, and 4% had type V root canal anatomy.. A high prevalence of 2 canals was noted in the first and second premolars. Also, 20% of first premolars and 34% of second premolars had a root canal anatomy other than type I.

Topics: Anatomic Variation; Bicuspid; Carbon; Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Ethanol; Female; Fixatives; Fused Teeth; Histocytological Preparation Techniques; Humans; Hygroscopic Agents; India; Male; Mandible; Nitric Acid; Root Canal Preparation; Salicylates; Solvents; Tooth Root

Polyketides and fatty acids are important in the production of pharmaceuticals, industrial chemicals, and biofuels. The synthesis of the malonyl-CoA building block, catalyzed by acetyl-CoA carboxylase (Acc1), is considered a limiting step to achieving high titers of polyketides and fatty acids in Saccharomyces cerevisiae. Acc1 is deactivated by AMP-activated serine/threonine protein kinase (Snf1) when glucose is depleted. To prevent this deactivation, the enzyme was aligned with the Rattus norvegicus (rat) Acc1 to identify a critical amino acid (Ser-1157) for phosphorylation and deactivation. Introduction of a S1157A mutation into Acc1 resulted in 9-fold higher specific activity following glucose depletion. The enzyme was tested in yeast engineered to produce the polyketide 6-methylsalisylic acid (6-MSA). Both 6-MSA and native fatty acid levels increased by 3-fold. Utilization of this modified Acc1 enzyme will also be beneficial for other products built from malonyl-CoA.

Topics: Acetyl-CoA Carboxylase; Amino Acid Sequence; Animals; Fatty Acids; Molecular Sequence Data; Polyketides; Protein Engineering; Rats; Saccharomyces cerevisiae; Saccharomyces cerevisiae Proteins; Salicylates; Sequence Alignment

A simple strategy for designing salt-based supramolecular gelators comprised of various nonsteroidal anti-inflammatory drugs (NSAIDs) and amantadine (AMN) (an antiviral drug) has been demonstrated using a supramolecular synthon approach. Single-crystal and powder X-ray diffraction established the existence of the well-studied gel-forming 1D supramolecular synthon, namely, primary ammonium monocarboxylate (PAM) synthon in all the salts. Remarkably five out of six salts were found to be capable of gelling methyl salicylate (MS)-an important ingredient in commercially available topical gels; one such selected biocompatible salt displayed an anti-inflammatory response in prostaglandin E2 (PGE2 ) assay, thereby indicating their plausible biomedical applications.

Topics: Amantadine; Animals; Anti-Inflammatory Agents, Non-Steroidal; Biocompatible Materials; Cell Line; Diclofenac; Dinoprostone; Gels; Interferon-gamma; Lipopolysaccharides; Macrophages; Mice; Rheology; Salicylates; Salts

In this paper, the volatiles emitted by flowers and various parts of the flower of a rare spontaneous Italian red (peel and flesh) apple named "Pelingo", were analyzed by SPME with the aim of identifying the contribution of each one to the whole aroma profile. Linalool was the most abundant volatile of flowers: from 43.0% in the flower buds, to 17.6% in the stylus and stigma headspace. The second most represented volatile was (E,E)-α-farnesene mainly emitted by the mature flowers (32.2%). Benzenoid compounds also have been identified: benzyl-alcohol is the most representative (1.0-16.5%) in all the samples except flower buds, while benzyl acetate (5.7%) and methyl salicylate (7.7%) are mainly present in the calyx and in the mature flowers respectively but not in the flower buds. Benzenoid compounds are the attractors for pollinator, probably for this reason were not detected in the headspace of flower buds.

Topics: Acyclic Monoterpenes; Benzyl Alcohol; Benzyl Compounds; Fatty Acids, Unsaturated; Flowers; Gas Chromatography-Mass Spectrometry; Italy; Malus; Monoterpenes; Pollination; Salicylates; Volatile Organic Compounds

We studied the knockdown activity and lethal toxicity of 6 essential oil compounds-methyl salicylate, linalool, 2-phenethyl alcohol, eugenol, β-citronellol, and trans-cinnamaldehyde-as fumigants against adult female Culex pipiens pallens in the laboratory. Of the 6 products tested, trans-cinnamaldehyde was the most toxic (LC50  =  0.26 µl/l air, 24 h) with a slow knockdown time (KT95  =  176.5 min at 0.5 µl/l air). Methyl salicylate displayed a lower toxicity (LC50  =  1.17 µl/l air, 24 h) but the fastest knockdown activity (KT95  =  16.8 min) at the sublethal concentration 0.5 µl/l air. Furthermore, the binary mixture of methyl salicylate and trans-cinnamaldehyde exhibited a combined effect of fast knockdown activity and high toxicity against Cx. p. pallens adults, showing potential for development as natural fumigants for mosquito control.

Topics: Acrolein; Animals; Culex; Female; Fumigation; Insecticides; Mosquito Control; Oils, Volatile; Salicylates

A suite of volatiles have previously been identified as specific markers of Mycobacterium tuberculosis metabolism in vitro. These markers - methyl phenylacetate, methyl p-anisate, methyl nicotinate, o-phenylanisole with the addition of methyl salicylate, may also be derived from other sources and confound development of a breath test for tuberculosis. To identify potential sources of these potential biomarkers food products, cosmetics, TB medication, environmental air and cigarette smoke were analysed for these markers using solid phase microextraction coupled with Gas Chromatography/Mass Spectrometry. Breath from healthy subjects, including smokers was also tested. Methyl salicylate was commonly detected, making this unsuitable as a specific marker for M. tuberculosis. Methyl nicotinate was detected repeatedly in cigarettes. Methyl phenylacetate was detected in 1.7% of healthy subjects and o-phenylanisole in just 1% of healthy breath indicating these may be more suitable for inclusion in the tuberculosis breath test due to their low "background" level. These results justify further clinical studies to further explore these markers as specific indicators of M. tuberculosis infection.

Topics: Adult; Air Pollutants; Anisoles; Antitubercular Agents; Biomarkers; Biphenyl Compounds; Breath Tests; Circadian Rhythm; Cosmetics; Environmental Monitoring; False Positive Reactions; Fasting; Female; Food Analysis; Gas Chromatography-Mass Spectrometry; Humans; Male; Middle Aged; Mycobacterium tuberculosis; Nicotinic Acids; Phenylacetates; Salicylates; Smoke; Smoking; Tuberculosis, Pulmonary; Young Adult

The purpose of this study is to synthesize chitosan (CS) nanoparticles (NPs) by ionic gelation with tripolyphosphate (TPP) as crossslinker in static mixers. The proposed static mixing technique showed good control over the ionic gelation process and 152-376 nm CS NPs were achieved in a continuous and scalable mode. Increasing the flow rates of CS:TPP solution streams, decreasing the CS concentration or reducing the CS:TPP solution volume ratio led to the smaller particles. Sylicylic acid (SA) was used as a model drug and successfully loaded into the CS NPs during the fabrication process. Our work demonstrates that ionic gelation-static mixing is a robust platform for continuous and large scale production of CS NPs for drug delivery.

Topics: Chitosan; Drug Carriers; Gels; Ions; Nanoparticles; Particle Size; Polyphosphates; Salicylates

Methyl salicylate (MeSA) is a green leaf volatile (GLV) compound that is emitted in significant amounts by plants, especially when they are under stress conditions. GLVs can then undergo chemical reactions with atmospheric oxidants, yielding compounds that contribute to the formation of secondary organic aerosols (SOAs). We investigated the adsorption of MeSA on atmospheric air/water interfaces at 298 K using thermodynamic integration (TI), potential of mean force (PMF) calculations, and classical molecular dynamics (MD) simulations. Our molecular models can reproduce experimental results of the 1-octanol/water partition coefficient of MeSA. A deep free energy minimum was found for MeSA at the air/water interface, which is mainly driven by energetic interactions between MeSA and water. At the interface, the oxygenated groups in MeSA tend to point toward the water side of the interface, with the aromatic group of MeSA lying farther away from water. Increases in the concentrations of MeSA lead to reductions in the height of the peaks in the MeSA-MeSA g(r) functions, a slowing down of the dynamics of both MeSA and water at the interface, and a reduction in the interfacial surface tension. Our results indicate that MeSA has a strong thermodynamic preference to remain at the air/water interface, and thus chemical reactions with atmospheric oxidants are more likely to take place at this interface, rather than in the water phase of atmospheric water droplets or in the gas phase.

Topics: Air; Atmosphere; Models, Molecular; Molecular Dynamics Simulation; Plant Leaves; Salicylates; Surface Properties; Water

Eastern hemlock (Tsuga canadensis) is in rapid decline because of infestation by the invasive hemlock woolly adelgid (Adelges tsugae; 'HWA') and, to a lesser extent, the invasive elongate hemlock scale (Fiorinia externa; 'EHS'). For many conifers, induced oleoresin-based defenses play a central role in their response to herbivorous insects; however, it is unknown whether eastern hemlock mobilizes these inducible defenses. We conducted a study to determine if feeding by HWA or EHS induced changes in the volatile resin compounds of eastern hemlock. Young trees were experimentally infested for 3 years with HWA, EHS, or neither insect. Twig and needle resin volatiles were identified and quantified by gas chromatography/mass spectrometry. We observed a suite of changes in eastern hemlock's volatile profile markedly different from the largely terpenoid-based defense response of similar conifers. Overall, both insects produced a similar effect: most twig volatiles decreased slightly, while most needle volatiles increased slightly. Only HWA feeding led to elevated levels of methyl salicylate, a signal for systemic acquired resistance in many plants, and benzyl alcohol, a strong antimicrobial and aphid deterrent. Green leaf volatiles, often induced in wounded plants, were increased by both insects, but more strongly by EHS. The array of phytochemical changes we observed may reflect manipulation of the tree's biochemistry by HWA, or simply the absence of functional defenses against piercing-sucking insects due to the lack of evolutionary contact with these species. Our findings verify that HWA and EHS both induce changes in eastern hemlock's resin chemistry, and represent the first important step toward understanding the effects of inducible chemical defenses on hemlock susceptibility to these exotic pests.

Topics: Animals; Benzyl Alcohol; Gas Chromatography-Mass Spectrometry; Hemiptera; Herbivory; Introduced Species; Plant Leaves; Plant Stems; Salicylates; Tsuga; Volatile Organic Compounds

Phenylpropanoid volatiles are responsible for the key tomato fruit (Solanum lycopersicum) aroma attribute termed "smoky." Release of these volatiles from their glycosylated precursors, rather than their biosynthesis, is the major determinant of smoky aroma in cultivated tomato. using a combinatorial omics approach, we identified the non-smoky glycosyltransferase1 (NSGT1) gene. Expression of NSGT1 is induced during fruit ripening, and the encoded enzyme converts the cleavable diglycosides of the smoky-related phenylpropanoid volatiles into noncleavable triglycosides, thereby preventing their deglycosylation and release from tomato fruit upon tissue disruption. In an nsgt1/nsgt1 background, further glycosylation of phenylpropanoid volatile diglycosides does not occur, thereby enabling their cleavage and the release of corresponding volatiles. Using reverse genetics approaches, the NSGT1-mediated glycosylation was shown to be the molecular mechanism underlying the major quantitative trait locus for smoky aroma. Sensory trials with transgenic fruits, in which the inactive nsgt1 was complemented with the functional NSGT1, showed a significant and perceivable reduction in smoky aroma. NSGT1 may be used in a precision breeding strategy toward development of tomato fruits with distinct flavor phenotypes.

Topics: Chromatography, Liquid; Chromosome Segregation; Chromosomes, Plant; Eugenol; Fruit; Gene Expression Regulation, Plant; Genetic Markers; Genome, Plant; Glycosides; Glycosylation; Glycosyltransferases; Guaiacol; Humans; Mass Spectrometry; Metabolome; Molecular Sequence Data; Odorants; Phylogeny; Plant Proteins; Plants, Genetically Modified; Salicylates; Solanum lycopersicum; Transcription, Genetic

Electrochemical sensing of methyl salicylate, a key plant volatile has been achieved using a gold nanoparticle (AuNP) modified screen printed carbon electrode (SPCE). The electrochemical response of planar gold electrodes, SPCE and AuNP-SPCE in alkaline electrolyte in the presence and absence of methyl salicylate were studied to understand the amperometric response of various electrochemical reactions. The reaction mechanism includes hydrolysis of methyl salicylate and the oxidation of negative species. The electrochemical responses were recorded using cyclic voltammetry and differential pulse voltammetry techniques, where the results showed characteristic signals for methyl salicylate oxidation. Among the examined electrodes, AuNP-SPCE possessed three fold better sensitivity than planar gold and 35 times better sensitivity than SPCE (at 0.5 V). The methyl salicylate sensing by AuNP-SPCE possessed <5% variation coefficient for repeatability, one week of stable performance with no more than 15% activity loss even if used multiple times (n = 8). Even in the presence of high concentration of interfering compounds such as cis-3-hexenol, hexyl acetate and cis-hexenyl acetate, AuNP-SPCE retained >95% of its methyl salicylate response. The electroanalytical results of soybean extract showed that AuNP-SPCE can be employed for the determination of methyl salicylate in real samples.

Topics: Electrochemical Techniques; Glycine max; Gold; Metal Nanoparticles; Salicylates

Green leaf volatiles (GLV), which are rapidly emitted by plants in response to insect herbivore damage, are now established as volatile defense signals. Receiving plants utilize these molecules to prime their defenses and respond faster and stronger when actually attacked. To further characterize the biological activity of these compounds we performed a microarray analysis of global gene expression. The focus of this project was to identify early transcriptional events elicited by Z-3-hexenol (Z-3-HOL) as our model GLV in maize (Zea mays) seedlings. The microarray results confirmed previous studies on Z-3-HOL -induced gene expression but also provided novel information about the complexity of Z-3-HOL -induced transcriptional networks. Besides identifying a distinct set of genes involved in direct and indirect defenses we also found significant expression of genes involved in transcriptional regulation, Ca(2+)-and lipid-related signaling, and cell wall reinforcement. By comparing these results with those obtained by treatment of maize seedlings with insect elicitors we found a high degree of correlation between the two expression profiles at this early time point, in particular for those genes related to defense. We further analyzed defense gene expression induced by other volatile defense signals and found Z-3-HOL to be significantly more active than methyl jasmonate, methyl salicylate, and ethylene. The data presented herein provides important information on early genetic networks that are activated by Z-3-HOL and demonstrates the effectiveness of this compound in the regulation of typical plant defenses against insect herbivores in maize.

Topics: Acetates; Animals; Cyclopentanes; Ethylenes; Gene Expression Profiling; Gene Expression Regulation, Plant; Gene Regulatory Networks; Genes, Plant; Herbivory; Hexanols; Oligonucleotide Array Sequence Analysis; Oxylipins; Plant Leaves; Reproducibility of Results; RNA, Messenger; Salicylates; Time Factors; Volatile Organic Compounds; Zea mays

Chemical warfare agent simulants are often used as an agent surrogate to perform environmental testing, mitigating exposure hazards. This work specifically addresses the assessment of downwind agent vapor concentration resulting from an evaporating simulant droplet. A previously developed methodology was used to estimate the mass diffusivities of the chemical warfare agent simulants methyl salicylate, 2-chloroethyl ethyl sulfide, di-ethyl malonate, and chloroethyl phenyl sulfide. Along with the diffusivity of the chemical warfare agent bis(2-chloroethyl) sulfide, the simulant diffusivities were used in an advection-diffusion model to predict the vapor concentrations downwind from an evaporating droplet of each chemical at various wind velocities and temperatures. The results demonstrate that the simulant-to-agent concentration ratio and the corresponding vapor pressure ratio are equivalent under certain conditions. Specifically, the relationship is valid within ranges of measurement locations relative to the evaporating droplet and observation times. The valid ranges depend on the relative transport properties of the agent and simulant, and whether vapor transport is diffusion or advection dominant.

Topics: Air Pollutants; Chemical Warfare Agents; Decontamination; Diffusion; Environmental Monitoring; Environmental Restoration and Remediation; Gases; Malonates; Models, Theoretical; Molecular Weight; Mustard Gas; Particle Size; Reproducibility of Results; Salicylates; Sulfides; Temperature

To study transdermal absorption characteristics of eugenol in compound Nanxing pain-relieving cataplasm, and discuss the effect of gaultherolin on the transdermal absorption of the cataplasm.. The improved franz diffusing cell was adopted with hairless mice skins as transdermal carriers. The content of eugenol in receptor liquid, skins and cataplasm were analyzed by HPLC and compared with the cataplasm without gaultherolin.. The penetration rates of eugenol of cataplasms with and without gaultherolin were 13.18 and 9.58 microg x cm(-2) x h(-1), with the retention amount in skins of (185.02 +/- 19.23) and (160.23 +/- 16.54) microg x g(-1) and the retention amount in cataplasms was (1.96 +/- 0.12) and (1.71 +/- 0.15) mg, respectively.. Eugenol in compound Nanxing pain-relieving cataplasm has good pereutaoeous permeation. Gaultherolin in the cataplasm prescription can promote the absorption of eugenol.

Topics: Analgesics; Animals; Chemistry, Pharmaceutical; Drugs, Chinese Herbal; Mice; Pain; Salicylates; Skin; Skin Absorption; Time Factors

Mouthwash ingestion has been observed in settings of restricted availability to alcoholic beverages such as in hospitals, prisons or military establishments. The literature offers limited evidence that ingredients of mouthwash may have health effects above the effects of ethanol. This study provides a quantitative risk assessment based on analysis of 30 mouthwash samples. All investigated brands contained alcohol, most of them menthol (93%), eucalyptol (90%), benzoic acid (87%), methyl salicylate (67%), and thymol (30%). For low risk drinking scenarios with average levels, only ethanol will exceed acceptable daily intakes (ADI). In worst case scenarios for alcohol dependent consumers ingesting 100g ethanol per day in the form of mouthwash, methyl salicylate will also exceeded the ADI by a factor of 17. The margin of exposure (MOE) for methyl salicylate, benzoates and thymol was below 100 for average scenarios, and below 10 for worst case scenarios, but ethanol is still the most toxic ingredient with MOE below 1. The occasional or even chronic ingestion of mouthwash may not cause health effects except the effects of ethanol alone. Only in extreme exposures, ingredients such as thymol or methyl salicylate could exacerbate the effects of ethanol, especially by contributing to metabolic acidosis.

Topics: Benzoic Acid; Cyclohexanols; Drinking Behavior; Ethanol; Eucalyptol; Humans; Menthol; Monoterpenes; Mouthwashes; Risk Assessment; Salicylates; Thymol

The excited-state properties of intramolecular hydrogen bonding (IMHB) in methyl salicylate (MS) and its effects on the excited-state intramolecular proton transfer (ESIPT) have been investigated using theoretical methods. From the geometric optimization and IR spectra in the ground and excited states calculated by density functional theory (DFT) and time-dependent DFT (TD-DFT) methods respectively, the IMHB is demonstrated to be significantly strengthened upon excitation to excited state S(1). Thereby, the ESIPT is facilitated by the excited-state IMHB strengthening since ESIPT takes place through IMHB. In addition, the absorption and fluorescence peaks of the S(1) state are also calculated using the TD-DFT method. It is noted that the calculated spectra are in good agreement with the experimental results, which has confirmed the ESIPT mechanism of MS first proposed by Weller. Moreover, other four 2-hydroxybenzoyl compounds forming strong IMHB are investigated to understand the effect of substituent R on the ESIPT process. We find that the hydrogen bond strength can be controlled by the inductive field effect of the substituent. Thus it is inferred that the ESIPT reaction can be facilitated by the inductive effect of electron-donating substituent.

Topics: Fluorescence; Hydrogen Bonding; Models, Molecular; Protons; Quantum Theory; Salicylates; Spectrophotometry, Infrared

The local lymph node assay (LLNA) is the preferred test for identification of skin-sensitizing substances by measuring radioactive thymidine incorporation into the lymph node. To facilitate acceptance of nonradioactive variants, validation authorities have published harmonized minimum performance standards (PS) that the alternative endpoint assay must meet. In the present work, these standards were applied to a variant of the LLNA based on lymph node cell counts (LNCC) run in parallel as a control with the standard LLNA with radioactivity measurements, with threshold concentrations (EC3) being determined for the sensitizers. Of the 22 PS chemicals tested in this study, 21 yielded the same results from standard radioactivity and cell count measurements; only 2-mercaptobenzothiazole was positive by LLNA but negative by LNCC. Of the 16 PS positives, 15 were positive by LLNA and 14 by LNCC; methylmethacrylate was not identified as sensitizer by either of the measurements. Two of the six PS negatives tested negative in our study by both LLNA and LNCC. Of the four PS negatives which were positive in our study, chlorobenzene and methyl salicylate were tested at higher concentrations than the published PS, whereas the corresponding concentrations resulted in consistent negative results. Methylmethacrylate and nickel chloride tested positive within the concentration range used for the published PS. The results indicate cell counts and radioactive measurements are in good accordance within the same LLNA using the 22 PS test substances. Comparisons with the published PS results may, however, require balanced analysis rather than a simple checklist approach.

Topics: Animals; Biological Assay; Cell Count; Chlorobenzenes; Dermatitis, Allergic Contact; Endpoint Determination; Female; Linear Models; Local Lymph Node Assay; Methylmethacrylate; Mice; Mice, Inbred CBA; Nickel; Radioactivity; Salicylates

Odorant-binding proteins (OBPs) are found in both insects and vertebrates, and it is believed that they are involved in chemical communication. In this study, we identify and express 2 OBPs from the scarab beetle, Holotrichia oblita Faldermann (Coleoptera: Scarabaeidae). HoblOBP1 shows more similarities with other scarab beetle OBPs, whereas HoblOBP2 is more diverse. N-phenyl-1-naphthylamine (1-NPN) is used as a fluorescent probe in ligand-binding experiment, and results indicate that both HoblOBPs prefer plant volatiles to putative H. oblita sex pheromones. HoblOBP1 shows binding affinity to a wider range of test compounds, but HoblOBP2 displays more specific binding affinity. Cinnamaldehyde and 2,4-di-tert-butylphenol bind to HoblOBP1 can elicit strong electrophysiological responses of the antennae from female H. oblita adults, respectively. Methyl salicylate also shows good affinity to HoblOBP2 and it can elicit moderate electrophysiological responses. Although, β-ionone is one of the ligands of the strongest binding, it elicits a weak electrophysiological response. In the immunocytochemical analysis, we observe that HoblOBP1 and HoblOBP2 are coexpressed in sensilla basiconica and placodea in both sexes.

Topics: 1-Naphthylamine; Acrolein; Amino Acid Sequence; Animals; Arthropod Antennae; Coleoptera; Female; Insect Proteins; Male; Molecular Sequence Data; Norisoprenoids; Phenols; Phylogeny; Protein Binding; Protein Isoforms; Receptors, Odorant; Recombinant Proteins; Salicylates; Sensilla; Sex Attractants; Smell; Substrate Specificity

Capsaicinoids, salicylic acid, methyl and ethyl salicylate, glycol monosalicylate, camphor and l-menthol are widely used in topical formulations to relieve local pain. For each separate compound or simple mixtures, quantitative analysis methods are reported. However, for a mixture containing all above mentioned active compounds, no assay methods were found. Due to the differing physicochemical characteristics, two methods were developed and optimized simultaneously. The non-volatile capsaicinoids, salicylic acid and glycol monosalicylate were analyzed with liquid chromatography following liquid-liquid extraction, whereas the volatile compounds were analyzed with static headspace-gas chromatography. For the latter method, liquid paraffin was selected as compatible dilution solvent. The optimized methods were validated in terms of specificity, linearity, accuracy and precision in a range of 80% to 120% of the expected concentrations. For both methods, peaks were well separated without interference of other compounds. Linear relationships were demonstrated with R² values higher than 0.996 for all compounds. Accuracy was assessed by performing replicate recovery experiments with spiked blank samples. Mean recovery values were all between 98% and 102%. Precision was checked at three levels: system repeatability, method precision and intermediate precision. Both methods were found to be acceptably precise at all three levels. Finally, the method was successfully applied to the analysis of some real samples (cutaneous sticks).

Topics: Analgesics, Non-Narcotic; Camphor; Capsaicin; Chromatography, Gas; Chromatography, Liquid; Liquid-Liquid Extraction; Menthol; Ointments; Pharmaceutical Preparations; Salicylates; Salicylic Acid; Sensitivity and Specificity

Volatiles emitted from stressed plants can induce resistance in healthy neighbors. It remains unknown, however, how plants perceive volatiles and convert them into internal signals. We exposed lima bean (Phaseolus lunatus L.) to different concentrations of either of two volatiles, nonanal and methyl salicylate (MeSA), over 6 or 24 h. Plant resistance to the bacterial pathogen, Pseudomonas syringae, was increased significantly after exposure to a headspace with two concentrations of nonanal for 6 h, and the same pattern emerged after an exposure over 24 h. By contrast, exposure to a low concentration of MeSA over 6 h did not significantly reduce bacterial infections, whereas exposure to the same concentration over 24 h significantly enhanced resistance. The dose-response relation that was apparent after 6 h of MeSA exposure disappeared in the 24 h treatment, in which the three tested concentrations caused indistinguishable, high levels of resistance to P. syringae. A low concentration of a potentially resistance-enhancing volatile sufficed to cause resistance to pathogens in the receiver plant only after long exposure time. Plant-plant signaling appears to involve the accumulation of volatiles in the receiver.

Topics: Aldehydes; Dose-Response Relationship, Drug; Phaseolus; Pseudomonas syringae; Salicylates; Time Factors; Volatile Organic Compounds

We prepared pressure-sensitive adhesive (PSA) patches based on styrene-isoprene-styrene (SIS) thermoplastic elastomer using hot-melt coating method. The liquid paraffine is added in the PSA matrices as a plasticizer to moderate the PSA properties. Three drugs, methyl salicylate, capsaicin, and diphenhydramine hydrochloride are selected as model drugs. The Fourier transform infrared spectroscopy, differential scanning calorimetry test, and wide-angle X-ray diffraction test indicate a good compatibility between drugs and matrices. Peppas equation is used to describe drug release profile. Different drug-matrix absorption, as indicative of drug-matrix interaction, accounts for the variation in release profiles of different drugs. Furthermore, atomic force microscopy and rheological studies of the PSA samples are performed to investigate the effect of SIS structure and plasticizer of PSA on drug release behaviors. For methyl salicylate and capsaicin, drug diffusion in the PSA matrices is the main factor controlled by the release kinetic constant k. The high [SI] diblock content and high plasticizer amount in matrix provide the PSA with a homogeneous and soften microstructure, resulting in a high diffusion rate. But for water-soluble drugs such as diphenhydramine hydrochloride, the release rate is governed by water penetration with the competition from diffusion mechanisms.

Topics: Administration, Cutaneous; Calorimetry, Differential Scanning; Capsaicin; Chemistry, Pharmaceutical; Chromatography, Gel; Crystallography, X-Ray; Diffusion; Diphenhydramine; Drug Carriers; Elastomers; Kinetics; Microscopy, Atomic Force; Models, Chemical; Molecular Structure; Plasticizers; Polystyrenes; Rheology; Salicylates; Solubility; Spectroscopy, Fourier Transform Infrared; Technology, Pharmaceutical; Terpenes; Transdermal Patch; Water

Upon insect herbivory, plants can release blends of volatile organic compounds (VOCs) that modify herbivore and natural enemy behaviour. We have shown recently that cotton, Gossypium hirsutum, emits a blend of defence VOCs that repels the cotton aphid, Aphis gossypii, upon herbivory by this notorious crop pest, including (Z)-3-hexenyl acetate, (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), methyl salicylate and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT). In this study, we investigated changes in the defence VOC profile of G. hirsutum induced by the naturally-occurring plant elicitor cis-jasmone (CJ) and whether these changes modify the behaviour of A. gossypii. In four-arm olfactometer assays, VOCs from untreated plants were significantly attractive (P<0.05), whilst VOCs from CJ-treated plants were significantly repellent (P<0.05). The VOCs induced by CJ appeared to comprise (Z)-3-hexenyl acetate, DMNT, methyl salicylate and TMTT. In quantitative VOC collection studies, sustained release of DMNT and TMTT was observed in CJ-treated plants over a period of five days, with levels becoming statistically significantly higher than for control treated plants on the fifth day in most cases. Despite earlier indications, no statistically significant differences were observed in levels of (Z)-3-hexenyl acetate or methyl salicylate between CJ and control treatments on any day. Furthermore, DMNT and TMTT emissions from CJ-treated plants were further enhanced by subsequent addition of A. gossypii. CJ treatment induced statistically significantly higher DMNT and TMTT expression levels as early as day three, when A. gossypii was present. The results in this study show that CJ can induce the production of A. gossypii-induced VOCs from G. hirsutum, with potential for deployment in novel crop protection strategies.

Topics: Acetates; Alkenes; Animals; Aphids; Cyclopentanes; Gossypium; Herbivory; Molecular Structure; Oxylipins; Salicylates; Stereoisomerism; Terpenes; Volatile Organic Compounds

Excited state intramolecular proton transfer (ESIPT) reaction along the O-H[Symbol: see text][Symbol: see text][Symbol: see text][Symbol: see text]O hydrogen bond of o-hydroxy benzaldehyde (OHBA), methyl salicylate (MS) and salicylic acid (SA) was investigated by ab-initio quantum chemical calculation and theory of atoms and molecules (QTAIM) for the first time. Variation in several geometric as well as QTAIM parameters along the reaction coordinate was monitored in the fully relaxed excited state potential energy curve (PEC) obtained from intrinsic reaction coordinate (IRC) analysis. Although, the excited state barrier height for the forward reaction (∆E (0) (#) ) reduces substantially in all the systems, MS and SA do not show any obvious asymmetry for proton transfer. For MS and SA, the crossover of the bond index as well as the lengths of the participating bonds at the saddle point is assigned due to this symmetry in accordance with bond energy - bond order (BEBO) model, which does not hold true in OHBA both in the ground and excited states. Bond ellipticity, covalent and metallic character were examined for different structures along the reaction path within the QTAIM framework. The QTAIM analysis was found to be able to uniquely distinguish between the ground and excited states of the OHBA molecule as well as both determining the effects on the bonding character of adding different substituent groups and differentiating between the ESIPT reactions in the SA and MS molecules.

Topics: Benzaldehydes; Electrons; Hydrogen Bonding; Models, Molecular; Molecular Conformation; Protons; Quantum Theory; Salicylates; Salicylic Acid; Thermodynamics

Headache after administration of electroconvulsive therapy (ECT) is common, affecting approximately half of patients treated. Post-ECT headache is typically treated with acetaminophen or nonsteroidal anti-inflammatory drugs but occasionally requires agents such as sumatriptan, opioids, or β-blockers. We report on a patient whose severe post-ECT headaches responded completely to methyl salicylate ointment, applied to the area of his temporalis and masseter muscles. Topical methyl salicylate is generally well tolerated and may be a viable option for some patients with post-ECT headache.

Topics: Administration, Topical; Adult; Anti-Inflammatory Agents, Non-Steroidal; Depressive Disorder, Major; Electroconvulsive Therapy; Headache; Humans; Ketorolac; Male; Ointments; Salicylates; Stress Disorders, Post-Traumatic

Coniferous trees have both constitutive and inducible defences that deter or kill herbivores and pathogens. We investigated constitutive and induced monoterpene responses of jack pine (Pinus banksiana Lamb.) to a number of damage types: a fungal associate of the mountain pine beetle (Dendroctonus ponderosae Hopkins), Grosmannia clavigera (Robinson-Jeffrey & R.W. Davidson); two phytohormones, methyl jasmonate (MJ) and methyl salicylate (MS); simulated herbivory; and mechanical wounding. We only included the fungal, MJ and mechanical wounding treatments in the field experiments while all treatments were part of the greenhouse studies. We focused on both constitutive and induced responses between juvenile and mature jack pine trees and differences in defences between phloem and needles. We found that phytohormone applications and fungal inoculation resulted in the greatest increase in monoterpenes in both juvenile and mature trees. Additionally, damage types differentially affected the proportions of individual monoterpenes: MJ-treated mature trees had higher myrcene and β-pinene than fungal-inoculated mature trees, while needles of juveniles inoculated with the fungus contained higher limonene than MJ- or MS-treated juveniles. Although the constitutive monoterpenes were higher in the phloem of juveniles than mature jack pine trees, the phloem of mature trees had a much higher magnitude of induction. Further, induced monoterpene concentrations in juveniles were higher in phloem than in needles. There was no difference in monoterpene concentration between phytohormone applications and G. clavigera inoculation in mature trees, while in juvenile trees MJ was different from both G. clavigera and simulated herbivory in needle monoterpenes, but there was no difference between phytohormone applications and simulated herbivory in the phloem.

Topics: Acetates; Animals; Ascomycota; Coleoptera; Cyclopentanes; Monoterpenes; Oxylipins; Phloem; Pinus; Plant Diseases; Plant Growth Regulators; Plant Immunity; Plant Leaves; Salicylates; Trees

In insects, odorant receptors detect volatile cues involved in behaviours such as mate recognition, food location and oviposition. We have investigated the evolution of three odorant receptors from five species within the moth genera Ctenopseustis and Planotrotrix, family Tortricidae, which fall into distinct clades within the odorant receptor multigene family. One receptor is the orthologue of the co-receptor Or83b, now known as Orco (OR2), and encodes the obligate ion channel subunit of the receptor complex. In comparison, the other two receptors, OR1 and OR3, are ligand-binding receptor subunits, activated by volatile compounds produced by plants--methyl salicylate and citral, respectively. Rates of sequence evolution at non-synonymous sites were significantly higher in OR1 compared with OR2 and OR3. Within the dataset OR1 contains 109 variable amino acid positions that are distributed evenly across the entire protein including transmembrane helices, loop regions and termini, while OR2 and OR3 contain 18 and 16 variable sites, respectively. OR2 shows a high level of amino acid conservation as expected due to its essential role in odour detection; however we found unexpected differences in the rate of evolution between two ligand-binding odorant receptors, OR1 and OR3. OR3 shows high sequence conservation suggestive of a conserved role in odour reception, whereas the higher rate of evolution observed in OR1, particularly at non-synonymous sites, may be suggestive of relaxed constraint, perhaps associated with the loss of an ancestral role in sex pheromone reception.

Topics: Acyclic Monoterpenes; Amino Acid Sequence; Animals; Base Sequence; Cloning, Molecular; DNA Primers; Evolution, Molecular; Likelihood Functions; Models, Genetic; Molecular Sequence Data; Monoterpenes; Moths; New Zealand; Phylogeny; Protein Subunits; Receptors, Odorant; Salicylates; Sequence Analysis, DNA; Species Specificity; Statistics, Nonparametric

A 16-month-old child developed a brief generalised tonic-clonic fitting episode and vomiting at home, after accidental ingestion of traditional massage oil. As the patient presented with clinical features of salicylate toxicity, appropriate management was instituted. He was admitted to the intensive care unit for multiorgan support. The child was discharged well 1 week after the incident. Methyl-salicylate is a common component of massage oils which are used for topical treatment of joint and muscular pains. However, these massage oils may be toxic when taken orally. Early recognition of the salicylate toxicity is very important in producing a good patient outcome.

Topics: Antidotes; Bicarbonates; Charcoal; Diuretics; Fluid Therapy; Furosemide; Humans; Infant; Intubation, Intratracheal; Male; Massage; Oils; Renal Dialysis; Salicylates; Seizures; Vomiting

Using herbivore-induced plant volatiles (HIPVs) to attract specific natural enemies in the field has proven challenging, partly because of a poor understanding of: (i) which compound(s) to manipulate to attract specific taxa, and (ii) the ecological conditions over which HIPVs are effective. To address these issues, we quantified the response of a complex arthropod community to three common HIPVs (methyl salicylate, cis-3-hexen-1-ol, and phenylethyl alcohol) as individual compounds and equal part blends in corn and soybean fields. Of 119 arthropod taxa surveyed, we found significant responses by four species in corn fields (2 parasitoids, 1 herbivore, and 1 detritivore) and 16 in soybean fields (8 parasitoids, 3 predators, 4 herbivores, and 1 detritivore), with both attractive and repellent effects of the HIPVs observed. For example, tachinid flies were highly attracted to cis-3-hexen-1-ol (ca. 3-fold increase), but repelled by methyl salicylate (ca. 60 % decrease). Surprisingly, we found very few cases in which HIPVs acted synergistically; only two arthropod groups (ichneumonid wasps and phorid flies) were more attracted by a blend of the HIPVs than by the individual compounds composing the blend. Crop type, however, had a strong impact on the strength of arthropod responses to HIPVs. A few arthropod species were broadly affected across both crops (i.e., the herbivore Halticus bractatus was repelled by most of our treatments, regardless of crop background), but overall more arthropod groups responded to HIPVs released in soybean fields compared with corn. This was true despite the fact that taxa responding to HIPVs were present and abundant in both systems, suggesting that crop-based outcomes were likely driven by the plant matrix rather than mere differences in taxonomic composition of the arthropod community in corn vs. soybean fields. As a whole, these results suggest that: (i) repellent effects of HIPVs on natural enemies of herbivorous insects can be observed as frequently as attractive effects; (ii) odor blends may be no more effective than single-compound lures for some taxa; and (iii) crop background alters the magnitude of attraction to HIPVs, depending on the species being targeted.

Topics: Animals; Arthropods; Glycine max; Hexanols; Indiana; Phenylethyl Alcohol; Salicylates; Volatile Organic Compounds; Zea mays

A field investigation was conducted on the spatial distributions of Sitobion avenae and its main natural enemies under wheat-oilseed rape intercropping and methyl salicylate application. With the development of wheat plant, an alternation from aggregation to uniform was observed in the spatial distribution of S. avenae under the intercropping and methyl salicylate application, being more obvious under the interaction of the two practices. The spatial distribution of S. avenae natural enemies was in accordance with that of the aphid. These results could be used for the reference of sampling investigation and forecast of wheat aphid and its natural enemies in field.

Topics: Agriculture; Animals; Aphids; Brassica rapa; Predatory Behavior; Salicylates; Spatial Analysis; Triticum

In order to explore the effects of wheat-oilseed rape intercropping in combining with methyl salicylate (MeSA) release on Sitobion avenae and its main natural enemies, a field experiment was conducted at the Tai'an Experimental Station of Shandong Agricultural University in East China from October 2008 to June 2010 to study the temporal dynamics of S. avenae and its main natural enemies as well as the ecological control effect on the aphid. In the plots of intercropping combined with MeSA release, the S. avenae apterae population reached a peak about 12 d in advance of the control, but the peak value was significantly lower than that of the control. The average annual number of S. avenae apterae per 100 wheat tillers decreased in the order of wheat monoculture > wheat-oilseed rape intercropping > MeSA release > wheat-oilseed rape intercropping combined with MeSA release. Moreover, the total number of ladybeetles was the highest in the plots of intercropping combined with MeSA release. The population densities of aphid parasitoids reached a peak about 10 d in advance of the control, which could play a significant role in controlling S. avenae at the filling stage of wheat. Taking the biological control index (BCI) as a quantitative indicator, and with the ladybeetles and parasitoids as the dominant control factors in fields, it was observed that wheat-oilseed rape intercropping combined with MeSA release could suppress the population increase of S. avenae apterae effectively from the heading to filling stages of wheat.

Topics: Agriculture; Animals; Aphids; Brassica; China; Ecosystem; Pest Control, Biological; Pheromones; Predatory Behavior; Salicylates; Triticum

Salicylic acid methyltransferases (SAMTs) synthesize methyl salicylate (MeSA) using salicylate as the substrate. MeSA synthesized in plants may function as an airborne signal to activate the expression of defense-related genes and could also be a critical mobile signaling molecule that travels from the site of plant infection to establish systemic immunity in the induction of disease resistance. Here the results of QM/MM free energy simulations for the methyl transfer process in Clarkia breweri SAMT (CbSAMT) are reported to determine the origin of the substrate specificity of SAMTs. The free energy barrier for the methyl transfer from S-adenosyl-L-methionine (AdoMet) to 4-hydroxybenzoate in CbSAMT is found to be about 5 kcal/mol higher than that from AdoMet to salicylate, consistent with the experimental observations. It is suggested that the relatively high efficiency for the methylation of salicylate compared to 4-hydroxybenzoate is due, at least in part, to the reason that a part of the stabilization of the transition state (TS) configuration is already reflected in the reactant complex, presumably, through the binding. The results seem to indicate that the creation of the substrate complex (e.g., through mutagenesis and substrate modifications) with its structure closely resembling TS might be fruitful for improving the catalytic efficiency for some enzymes. The results show that the computer simulations may provide important insights into the origin of the substrate specificity for the SABATH family and could be used to help experimental efforts in generating engineered enzymes with altered substrate specificity.

Topics: Binding Sites; Catalysis; Clarkia; Computer Simulation; Methylation; Methyltransferases; Models, Molecular; Parabens; Plant Immunity; Plant Proteins; Protein Binding; Protein Engineering; S-Adenosylmethionine; Salicylates; Salicylic Acid; Substrate Specificity; Thermodynamics

The volatile compounds that constitute the fruit aroma of ripe tomato (Solanum lycopersicum) are often sequestered in glycosylated form. A homology-based screen was used to identify the gene SlUGT5, which is a member of UDP-glycosyltransferase 72 family and shows specificity towards a range of substrates, including flavonoid, flavanols, hydroquinone, xenobiotics and chlorinated pollutants. SlUGT5 was shown to be expressed primarily in ripening fruit and flowers, and mapped to chromosome I in a region containing a QTL that affected the content of guaiacol and eugenol in tomato crosses. Recombinant SlUGT5 protein demonstrated significant activity towards guaiacol and eugenol, as well as benzyl alcohol and methyl salicylate; however, the highest in vitro activity and affinity was shown for hydroquinone and salicyl alcohol. NMR analysis identified isosalicin as the only product of salicyl alcohol glycosylation. Protein modelling and substrate docking analysis were used to assess the basis for the substrate specificity of SlUGT5. The analysis correctly predicted the interactions with SlUGT5 substrates, and also indicated that increased hydrogen bonding, due to the presence of a second hydrophilic group in methyl salicylate, guaiacol and hydroquinone, appeared to more favourably anchor these acceptors within the glycosylation site, leading to increased stability, higher activities and higher substrate affinities.

Topics: Amino Acid Sequence; Benzyl Alcohol; Benzyl Alcohols; Catalytic Domain; Chromosomes; Cloning, Molecular; Escherichia coli; Eugenol; Gene Expression; Glycosyltransferases; Guaiacol; Hydrogen Bonding; Hydroquinones; Models, Molecular; Molecular Sequence Data; Phenols; Phenylethyl Alcohol; Phylogeny; Plant Proteins; Plant Structures; Recombinant Proteins; Salicylates; Sequence Homology, Amino Acid; Solanum lycopersicum; Substrate Specificity; Uridine Diphosphate Glucose; Volatile Organic Compounds

A simple clearing technique is presented by which species specific structures and organs of blowfly larvae can easily be visualized and displayed without any danger of mechanical damages or dislocations of delicate formations and without fixation of the object.

Topics: Animals; Diptera; Entomology; Fixatives; Forensic Anthropology; Forensic Pathology; Larva; Microscopy; Salicylates; Species Specificity

Topics: Arabidopsis; Arabidopsis Proteins; Carrier Proteins; Fatty Acid-Binding Proteins; Gene Expression Regulation, Plant; Immunity, Innate; Lipids; Methyltransferases; Molecular Sequence Data; Mutation; Nicotiana; Salicylates; Signal Transduction

An increasing body of evidence indicates that the association between different plant species may lead to a reduction in insect herbivory, i.e. associational resistance. This might be due to a top-down regulation of herbivores by increased numbers of natural enemies or to a disruptive bottom-up influence of lower host plant accessibility. In particular, the richer plant communities release more diverse plant odours that may disturb olfactory-guided host choice and mating behaviour of insect herbivores, i.e. the "semiochemical diversity hypothesis". However, this hypothesis has been rarely tested experimentally in natural habitats, notably forest ecosystems. We tested the effects of non-host volatiles (NHV) on mate and host location by the pine processionary moth (PPM) at the scale of individual pine trees with branches of non-host tree (birch) at their base. Pheromone trap catches and the numbers of larval nests were both reduced by non-host presence under treated pine trees, confirming an associational resistance mediated by NHV. In both males and females, the antenna could detect several birch volatiles, including methyl salicylate (MeSa). MeSa inhibited the attraction of the PPM male to pheromone traps, as did bark and leaf chips from birch trees. Our test of three doses of MeSa at the habitat scale (50 m forest edges) showed that the reduction in the numbers of male PPM captured in traps and in larval nests was MeSa dose-dependent. These results show that odours released by deciduous non-host trees can reduce herbivory by a forest defoliator in conifers, providing support to the "semiochemical diversity hypothesis" as a mechanism of associational resistance.

Topics: Animals; Arthropod Antennae; Betula; Female; France; Male; Moths; Odorants; Pheromones; Pinus; Salicylates; Smell

Several studies have shown that herbivore-induced plant volatiles act directly on herbivores and indirectly on their natural enemies. However, little is known about the effect of herbivore damage on resistant and susceptible plant cultivars and its effect on their natural enemies. Thus, the aim of this study was to evaluate the attraction of the herbivorous pentatomid bug Euschistus heros and its egg parasitoid Telenomus podisi to two resistant and one susceptible soybean cultivars with different types of damage (herbivory, herbivory+oviposition, and oviposition). In a Y-tube olfactometer, the parasitoids were attracted to herbivory and herbivory+oviposition damaged soybean plants when compared to undamaged soybean plants for the resistant cultivars, but did not show preference for the susceptible cultivar Silvânia in any of the damage treatments. The plant volatiles emitted by oviposition-damaged plants in the three cultivars did not attract the egg parasitoid. In four-arm-olfactometer bioassays, E. heros females did not show preference for odors of damaged or undamaged soybean plants of the three cultivars studied. The Principal Response Curves (PRC) analysis showed consistent variability over time in the chemical profile of volatiles between treatments for the resistant cultivar Dowling. The compounds that most contributed to the divergence between damaged soybean plants compared to undamaged plants were (E,E)-α-farnesene, methyl salicylate, (Z)-3-hexenyl acetate, and (E)-2-octen-1-ol.

Topics: Acetates; Animals; Behavior, Animal; Female; Glycine max; Host-Parasite Interactions; Hymenoptera; Octanols; Oviposition; Pentastomida; Plant Leaves; Salicylates; Sesquiterpenes; Time Factors

The responses of the predatory mite P. persimilis to herbivore-induced plant volatiles are at least partly genetically determined. Thus, there is potential for the evolution of this behaviour by natural selection. We tested whether distinct predator genotypes with contrasting responses to a specific herbivore-induced plant volatile, i.e. methyl salicylate (MeSa), could be found in a base population collected in the field (Sicily). To this end, we imposed purifying selection on individuals within iso-female lines of P. persimilis such that the lines were propagated only via the individual that showed either a preference or avoidance of MeSa. The responses of the lines were characterized as the mean proportion of individuals choosing MeSa when given a choice between MeSa and clean air. Significant variation in predator responses was detected among iso-female lines, thus confirming the presence of a genetic component for this behaviour. Nevertheless, we did not find a significant difference in the response to MeSa between the lines that were selected to avoid MeSa and the lines selected to prefer MeSa. Instead, in the course of selection the lines selected to avoid MeSa shifted their mean response towards a preference for MeSa. An inverse, albeit weaker, shift was detected for the lines selected to prefer MeSa. We discuss the factors that may have caused the apparent lack of a response to selection within iso-female line in this study and propose experimental approaches that address them.

Topics: Animals; Behavior, Animal; Choice Behavior; Female; Mites; Plants; Predatory Behavior; Salicylates; Selection, Genetic

Programmed cell death (PCD) is a genetically encoded, active process that results in the death of individual cells, tissues, or whole organs, which plays an important role in the life cycles of plants and animals. Previous studies show that methyl salicylate (MeSA) is a defense signal molecular associated with systemic acquired resistance and hypersensitive reaction; however, whether MeSA can induce PCD in plant is still unknown. The morphological changes of Arabidopsis thaliana protoplasts exposed to MeSA were observed under fluorescence microscopy and transmission electron microscopy, and the induction of PCD was clearly distinguished by intense perinuclear chromatin margination, condensation of nuclear chromatin and DNA laddering after 3-h exposure of 100 μM MeSA. Our results also showed that salicylic acid (SA) was involved in MeSA-induced PCD by using a transgenic nahG Arabidopsis thaliana line, and the process was mediated by reactive oxygen species, which functioned with SA by making an amplification loop. Our study showed that MeSA could induce PCD in plant cell for the first time.

Topics: Arabidopsis; Cell Death; Cell Nucleus; Cell Survival; Hydrogen Peroxide; Microscopy, Electron, Transmission; Microscopy, Fluorescence; Plant Leaves; Plants, Genetically Modified; Protoplasts; Reactive Oxygen Species; Salicylates; Salicylic Acid; Signal Transduction

Methyl salicylate, an herbivore-induced plant volatile, has been shown to attract natural enemies and affect herbivore behavior. In this study, methyl salicylate was examined for its attractiveness to natural enemies of the soybean aphid, Aphis glycines Matsumura (Hemiptera: Aphididae), and for its direct effects on soybean aphid population growth rates. Methyl salicylate lures were deployed in plots within organic soybean [Glycine max (L.) Merr.] fields. Sticky card traps adjacent to and 1.5 m from the lure measured the relative abundance of natural enemies, and soybean aphid populations were monitored within treated and untreated plots. In addition, exclusion cage studies were conducted to determine methyl salicylate's effect on soybean aphid population growth rates in the absence of natural enemies. Significantly greater numbers of syrphid flies (Diptera: Syrphidae) and green lacewings (Neuroptera: Chrysopidae) were caught on traps adjacent to the methyl salicylate lure, but no differences in abundance were found at traps 1.5 m from the lure. Furthermore, abundance of soybean aphids was significantly lower in methyl salicylate-treated plots. In exclusion cage studies, soybean aphid numbers were significantly reduced on treated soybean plants when all plants were open to natural enemies. When plants were caged, however, soybean aphid numbers and population growth rates did not differ between treated and untreated plants suggesting no effect of methyl salicylate on soybean aphid reproduction and implicating the role of natural enemies in depressing aphid populations. Although aphid populations were reduced locally around methyl salicylate lures, larger scale studies are needed to assess the technology at the whole-field scale.

Topics: Animals; Aphids; Food Chain; Glycine max; Pest Control, Biological; Population Density; Population Growth; Salicylates

The root and leaf essential oils, present in trace amounts in Amsonia illustris Woods. (Apocynaceae), were isolated by steam distillation and their chemical constituents identified by GC-FID and GC-MS. More than 80% of the thirty volatile compounds in the leaf oil were identified, the major constituents being mainly sesquiterpenes like a-humulene (14.5%), beta-caryophyllene (12.4%) and guaiol (11.6%). The volatile ingredients of the root oil were pinocampheol, methyl salicylate, (2E,4E)- decadienal, eugenol and trans-isoeugenol.

Topics: Amsonia; Eugenol; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Salicylates; Sesquiterpenes; Sesquiterpenes, Guaiane

Plants attacked by herbivorous insects emit volatile organic compounds that are used by natural enemies to locate their host or prey. The composition of the blend is often complex and specific. It may vary qualitatively and quantitatively according to plant and herbivore species, thus providing specific information for carnivorous arthropods. Most studies have focused on simple interactions that involve one species per trophic level, and typically have investigated the aboveground parts of plants. These investigations need to be extended to more complex networks that involve multiple herbivory above- and belowground. A previous study examined whether the presence of the leaf herbivore Pieris brassicae on turnip plants (Brassica rapa subsp. rapa) influences the response of Trybliographa rapae, a specialist parasitoid of the root feeder Delia radicum. It showed that the parasitoid was not attracted by volatiles emitted by plants under simultaneous attack. Here, we analyzed differences in the herbivore induced plant volatile (HIPV) mixtures that emanate from such infested plants by using Orthogonal Partial Least Squares-Discriminant Analysis (OPLS-DA). This multivariate model focuses on the differences between odor blends, and highlights the relative importance of each compound in an HIPV blend. Dual infestation resulted in several HIPVs that were present in both isolated infestation types. However, HIPVs collected from simultaneously infested plants were not the simple combination of volatiles from isolated forms of above- and belowground herbivory. Only a few specific compounds characterized the odor blend of each type of damaged plant. Indeed, some compounds were specifically induced by root herbivory (4-methyltridecane and salicylaldehyde) or shoot herbivory (methylsalicylate), whereas hexylacetate, a green leaf volatile, was specifically induced after dual herbivory. It remains to be determined whether or not these minor quantitative variations, within the background of more commonly induced odors, are involved in the reduced attraction of the root feeder's parasitoid. The mechanisms involved in the specific modification of the odor blends emitted by dual infested turnip plants are discussed in the light of interferences between biosynthetic pathways linked to plant responses to shoot or root herbivory.

Topics: Acetates; Aldehydes; Alkanes; Animals; Brassica napus; Diptera; Gas Chromatography-Mass Spectrometry; Host-Parasite Interactions; Hymenoptera; Least-Squares Analysis; Plant Leaves; Plant Roots; Plant Shoots; Salicylates; Volatile Organic Compounds

Vapors of four chemical warfare agent (CWA) stimulants, 2-chloroethyl ethyl sulfide (CEES), diethyl malonate (DEM), dimethyl methylphosphonate (DMMP), and methyl salicylate (MeS), were detected, identified, and quantitated using a fully automated, field-deployable, miniature mass spectrometer. Samples were ionized using a glow discharge electron ionization (GDEI) source, and ions were mass analyzed with a cylindrical ion trap (CIT) mass analyzer. A dual-tube thermal desorption system was used to trap compounds on 50:50 Tenax TA/Carboxen 569 sorbent before their thermal release. The sample concentrations ranged from low parts per billion [ppb] to two parts per million [ppm]. Limits of detection (LODs) ranged from 0.26 to 5.0 ppb. Receiver operating characteristic (ROC) curves are presented for each analyte. A sample of CEES at low ppb concentration was combined separately with two interferents, bleach (saturated vapor) and diesel fuel exhaust (1%), as a way to explore the capability of detecting the simulant in an environmental matrix. Also investigated was a mixture of the four CWA simulants (at concentrations in air ranging from 270 to 380 ppb). Tandem mass (MS/MS) spectral data were used to identify and quantify the individual components.

Topics: Air; Chemical Warfare Agents; Malonates; Miniaturization; Models, Chemical; Mustard Gas; Organophosphorus Compounds; ROC Curve; Salicylates; Sensitivity and Specificity; Tandem Mass Spectrometry

Insect herbivory induces plant odors that attract herbivores' natural enemies. Assuming this attraction emerges from individual compounds, genetic control over odor emission of crops may provide a rationale for manipulating the distribution of predators used for pest control. However, studies on odor perception in vertebrates and invertebrates suggest that olfactory information processing of mixtures results in odor percepts that are a synthetic whole and not a set of components that could function as recognizable individual attractants. Here, we ask if predators respond to herbivore-induced attractants in odor mixtures or to odor mixture as a whole.. We studied a system consisting of Lima bean, the herbivorous mite Tetranychus urticae and the predatory mite Phytoseiulus persimilis. We found that four herbivore-induced bean volatiles are not attractive in pure form while a fifth, methyl salicylate (MeSA), is. Several reduced mixtures deficient in one component compared to the full spider-mite induced blend were not attractive despite the presence of MeSA indicating that the predators cannot detect this component in these odor mixtures. A mixture of all five HIPV is most attractive, when offered together with the non-induced odor of Lima bean. Odors that elicit no response in their pure form were essential components of the attractive mixture.. We conclude that the predatory mites perceive odors as a synthetic whole and that the hypothesis that predatory mites recognize attractive HIPV in odor mixtures is unsupported.

Topics: Animals; Feeding Behavior; Female; Odorants; Phaseolus; Predatory Behavior; Salicylates; Tetranychidae; Volatile Organic Compounds

The effects of methyl salicylate (MeSA) on chilling injury (CI) and gene expression levels, enzyme activities, and metabolites related to arginine catabolism in cherry tomato fruit were investigated. Freshly harvested fruits were treated with 0.05 mM MeSA vapor at 20 °C for 12 h and then stored at 2 °C for up to 28 days. MeSA reduced CI and enhanced the accumulation of putrescine, spermidine, and spermine, which was associated with increased gene expression levels and activities of arginase, arginine decarboxylase, and ornithine decarboxylase at most sampling times. MeSA also increased nitric oxide synthase activity, which at least partly contributed to the increased nitric oxide content. The results indicate that MeSA activates the different pathways of arginine catabolism in cold-stored fruit and that the reduction in CI by MeSA may be due to the coordinated metabolism of arginine and the increase in polyamines and nitric oxide levels.

Topics: Arginase; Arginine; Carboxy-Lyases; Cold Temperature; Fruit; Nitric Oxide; Nitric Oxide Synthase; Ornithine Decarboxylase; Polyamines; Salicylates; Solanum lycopersicum; Up-Regulation

Siegesbeckia orientalis has been traditionally used as a topical anti-inflammatory and analgesic agent.. Current study was designed to explore the topical anti-inflammatory and analgesic effects of a constituent isolated from Siegesbeckia orientalis (Compositae), in order to validate its folk use.. Kirenol was isolated from ethanolic extract of Siegesbeckia orientalis. Several topical formulations containing kirenol were investigated for anti-inflammatory and analgesic activities in rat. The effects were studied using carrageenan-induced rat acute inflammation model, complete Freund's adjuvant (CFA)-induced chronic inflammation and formalin test in rats. Piroxicam gel and methyl salicylate ointment were studied as positive control for anti-inflammatory and analgesic activity, respectively.. The anti-inflammatory effect of kirenol 0.4-0.5% (w/w) was similar to the effect of piroxicam gel 4h after carrageenan injection. The analgesic activity of topical preparation with more than 0.4% (w/w) was observed in the late phase. These effects may be due, at least in part, to the pro-inflammatory cytokine production of IL-1β and TNF-α. The administration of kirenol cream at the dose of 0.3, 0.4 and 0.5% (w/w) significantly inhibited the development of joint swelling induced by CFA, which was auxiliary supported by histopathological studies.. Kirenol has demonstrated its significant potential to be further investigated for its discovery as a new lead compound for management of topical pain and inflammation, although further pharmacological research is necessary to fully understand its mechanism of action. It also supports the potential beneficial effect of topically administered Siegesbeckia orientalis in inflammatory diseases.

Topics: Administration, Topical; Analgesics; Animals; Anti-Inflammatory Agents; Arthritis, Experimental; Asteraceae; Carrageenan; Diterpenes; Dose-Response Relationship, Drug; Drugs, Chinese Herbal; Ethanol; Formaldehyde; Freund's Adjuvant; Inflammation; Inflammation Mediators; Interleukin-1beta; Pain; Piroxicam; Plant Components, Aerial; Plants, Medicinal; Rats; Salicylates; Solvents; Time Factors; Tumor Necrosis Factor-alpha

Methyl salicylate (MeS) has a rich history as an inert physical simulant for the chemical warfare agents sulfur mustard and soman, where it is used extensively for liquid- and vapor-permeation testing. Here we demonstrate possible utility of MeS as a reactivity simulant for chlorine-based decontaminants. In these experiments MeS was reacted with sodium hypochlorite varying stoichiometry, temperature, reaction time, and pH. No colored oxidation products were observed; however, chlorination of the aromatic ring occurred ortho (methyl 3-chlorosalicylate) and para (methyl 5-chlorosalicylate) to the position bearing the -OH group in both the mono- and disubstituted forms. The monosubstituted para product accumulated initially, and the ortho and 3,5-dichloro products formed over the next several hours. Yields from reactions conducted below pH 11 declined rapidly with decreasing pH. Reactions run at 40 °C produced predominantly para substitution, while those run at 0 °C produced lower yields of ortho- and para-substituted products. Reactions were also carried out on textile substrates of cotton, 50/50 nylon-cotton, and a meta aramid. The textile data broadly reproduced reaction times and stoichiometry observed in the liquid phase, but are complicated by physical and possibly chemical interactions with the fabric. These data indicate that, for hypochlorite-containing neutralizing agents operating at strongly alkaline pH, one can expect MeS to react stoichiometrically with the hypochlorite it encounters. This suggests utility of MeS in lieu of such highly hazardous surrogates as monochloroalkyl sulfides as a simulant for threat scenarios involving the stoichiometric decomposition of sulfur mustard. Specifically, the extent of coverage of the simulant on a fabric by the neutralizing agent can be directly measured. Similar reactivity toward other halogen oxidizing agents is likely but remains to be demonstrated.

Topics: Chemical Warfare Agents; Decontamination; Halogenation; Hydrogen-Ion Concentration; Oxidation-Reduction; Salicylates; Sodium Hypochlorite

The use of synthetic herbivore-induced plant volatiles (HIPV) to attract natural enemies has received interest as a tool to enhance conservation biological control (CBC). Methyl salicylate (MeSA) is a HIPV that is attractive to several key predators of two-spotted spider mite, Tetranychus urticae Koch (Acari: Tetranychidae), and hop aphid, Phorodon humuli (Schrank) (Homoptera: Aphididae). A 2-year study was conducted to evaluate the recommended commercial use of MeSA in hop yards in Oregon. Slow-release MeSA dispensers were stapled to supporting poles in 0.5 ha plots and these plots were compared to a paired non-treated plot on each of three farms in 2008 and 2009. Across both years, there was a trend for reduced (range 40-91%) mean seasonal numbers of T. urticae in five of the six MeSA-baited plots. Stethorus spp., key spider mite predators, tended to be more numerous in MeSA-baited plots compared to control plots on a given farm. Mean seasonal densities of hop aphid and other natural enemies (e.g., Orius spp. and Anystis spp.) were similar between MeSA-treated and control plots. Variability among farms in suppression of two-spotted spider mites and attraction of Stethorus spp. suggests that the use of MeSA to enhance CBC of spider mites in commercial hop yards may be influenced by site-specific factors related to the agroecology of individual farms or seasonal effects that require further investigation. The current study also suggests that CBC of hop aphid with MeSA in this environment may be unsatisfactory.

Topics: Animals; Aphids; Cannabaceae; Insect Control; Oregon; Salicylates; Tetranychidae

Systemic acquired resistance (SAR) is a state of heightened defense to a broad spectrum of pathogens that is activated throughout a plant following local infection. Development of SAR requires the translocation of one or more mobile signals from the site of infection through the vascular system to distal (systemic) tissues. The first such signal identified was methyl salicylate (MeSA) in tobacco (Nicotiana tabacum). Subsequent studies demonstrated that MeSA also serves as a SAR signal in Arabidopsis (Arabidopsis thaliana) and potato (Solanum tuberosum). By contrast, another study suggested that MeSA is not required for SAR in Arabidopsis and raised questions regarding its signaling role in tobacco. Differences in experimental design, including the developmental age of the plants, the light intensity, and/or the strain of bacterial pathogen, were proposed to explain these conflicting results. Here, we demonstrate that the length of light exposure that plants receive after the primary infection determines the extent to which MeSA is required for SAR signaling. When the primary infection occurred late in the day and as a result infected plants received very little light exposure before entering the night/dark period, MeSA and its metabolizing enzymes were essential for SAR development. In contrast, when infection was done in the morning followed by 3.5 h or more of exposure to light, SAR developed in the absence of MeSA. However, MeSA was generally required for optimal SAR development. In addition to resolving the conflicting results concerning MeSA and SAR, this study underscores the importance of environmental factors on the plant's response to infection.

Topics: Arabidopsis; Gene Expression Regulation, Plant; Light; Mutation; Nicotiana; Plant Diseases; Plant Immunity; Plant Leaves; Pseudomonas syringae; Salicylates; Signal Transduction; Time Factors

N,N'-bis-(α-methylsalicylidene)-2,2-dimethyl-1,3-propanediimine (SBTD) modified silica gel was prepared and used as sorbent for solid phase extraction of Cr(III) ions from aqueous solution. This sorbent showed a high sorption affinity for Cr(III) while recovery of Cr(VI) was very low. The analyte ion retained on the column was eluted with 1 mol L(-1) HNO(3). The chromium ion in the eluent was determined by graphite furnace atomic absorption spectrometry. The effects of different parameters such as pH, eluent type and volume, Schiff's base concentration, sample and eluent flow rate, interfering ions and adsorbent amount were investigated.

Topics: Chromium Compounds; Salicylates; Silica Gel; Solid Phase Extraction

We have previously shown that local exposure of plants to stress results in a systemic increase in genome instability. Here, we show that UV-C-irradiated plants produce a volatile signal that triggers an increase in genome instability in neighboring nonirradiated Arabidopsis thaliana plants. This volatile signal is interspecific, as UV-C-irradiated Arabidopsis plants transmit genome destabilization to naive tobacco (Nicotiana tabacum) plants and vice versa. We report that plants exposed to the volatile hormones methyl salicylate (MeSA) or methyl jasmonate (MeJA) exhibit a similar level of genome destabilization as UV-C-irradiated plants. We also found that irradiated Arabidopsis plants produce MeSA and MeJA. The analysis of mutants impaired in the synthesis and/or response to salicylic acid (SA) and/or jasmonic acid showed that at least one other volatile compound besides MeSA and MeJA can communicate interplant genome instability. The NONEXPRESSOR OF PATHOGENESIS-RELATED GENES1 (npr1) mutant, defective in SA signaling, is impaired in both the production and the perception of the volatile signals, demonstrating a key role for NPR1 as a central regulator of genome stability. Finally, various forms of stress resulting in the formation of necrotic lesions also generate a volatile signal that leads to genomic instability.

Topics: Acetates; Arabidopsis; Arabidopsis Proteins; Bacterial Proteins; Cyclopentanes; Gene Expression Regulation, Plant; Genome, Plant; Genomic Instability; Homologous Recombination; Membrane Proteins; Mutation; Nicotiana; Oxylipins; Plants, Genetically Modified; Salicylates; Salicylic Acid; Signal Transduction; Stress, Physiological; Tobacco Mosaic Virus; Ultraviolet Rays

Herbivore-induced plant volatiles (HIPVs) emitted from lima bean leaves infested with the two-spotted spider mites Tetranychus urticae strongly attract the predatory mites Neoseiulus californicus. Among these HIPVs, methyl salicylate and linalool can attract the predators. Three green-leaf volatiles (GLVs) of (Z)-3-hexen-1-ol, (Z)-3-hexenyl acetate and (E)-2-hexenal, found in the odor blends from T. urticae-infested leaves and physically damaged leaves, can also attract the predators. To search for a strong predator attractant, the olfactory responses of N. californicus to each synthetic compound or their combinations were investigated in a Y-tube olfactometer. When presented a choice between a mixture of the five compounds (i.e. the two HIPVs and the three GLVs) and T. urticae-infested leaves, N. californicus did not discriminate between these odor sources. The same trend was observed when either a mixture of the two HIPVs or methyl salicylate vs. T. urticae-infested leaves were compared. In contrast, the predators preferred T. urticae-infested leaves to linalool, each of the three GLVs, or a mixture of the three GLVs. These results indicated that methyl salicylate is a strong predator attractant, and its potential attractiveness almost equaled that of the blend of HIPVs from T. urticae-infested leaves.

Topics: Animals; Behavior, Animal; Mites; Phaseolus; Plant Extracts; Plant Leaves; Predatory Behavior; Salicylates; Smell; Tetranychidae; Volatilization

Methyl salicylate (MeSA), which is synthesized in plants from salicylic acid (SA) by methyltransferases, has roles in defense against microbial and insect pests. Most of the MeSA that accumulates after pathogen attack is synthesized by benzoic acid/SA carboxyl methyltransferase 1 (AtBSMT1). To investigate the role of AtBSMT1 in plant defense, transgenic Arabidopsis with altered AtBSMT1 function or expression were assessed for their ability to resist pathogen infection. A knockout mutant (Atbsmt1) failed to accumulate MeSA following pathogen infection; these plants also failed to accumulate SA or its glucoside in the uninoculated leaves and did not develop systemic acquired resistance (SAR). However, the Atbsmt1 mutant exhibited normal levels of effector-triggered immunity and pathogen-associated molecular pattern (PAMP)-triggered immunity to Pseudomonas syringae and Hyaloperonospora arabidopsidis. Analyses of transgenic Arabidopsis plants overexpressing AtBSMT1 revealed that they accumulate elevated levels of MeSA in pathogen-infected leaves but fail to develop SAR. Since the levels of SA and its glucoside were reduced in uninoculated systemic leaves of these plants whereas MeSA levels were elevated, AtBSMT1-mediated conversion of SA to MeSA probably compromised SAR development by suppressing SA accumulation in uninoculated leaves. PAMP-triggered immunity also was compromised in the AtBSMT1 overexpressing plants, although effector-triggered immunity was not.

Topics: Arabidopsis; Arabidopsis Proteins; Benzoic Acid; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Gene Knockout Techniques; Immunity, Innate; Methyltransferases; Oomycetes; Plant Diseases; Plant Leaves; Plants, Genetically Modified; Pseudomonas syringae; Salicylates; Salicylic Acid

The aim of the present work was to verify the possibility of detecting various tissue antigens using standard immunocytochemical methods in paraffin sections of specimens stored in methylsalicylate for two years and longer before embedding in paraffin. Using the immunocytochemical reaction for the intermediate filament proteins nestin, vimentin, and GFAP, the neuron marker NeuN, neuron-specific enolase, and doublecortin as examples, these experiments showed that prolonged storage of dehydrated specimens in methylsalicylate does not prevent detection of antigens using immunocytochemical reactions.

Topics: Aging; Animals; Antigens, Nuclear; Brain; Doublecortin Domain Proteins; Doublecortin Protein; Fixatives; Glial Fibrillary Acidic Protein; Immunohistochemistry; Intermediate Filament Proteins; Microtubule-Associated Proteins; Nerve Tissue Proteins; Nestin; Neuroglia; Neurons; Neuropeptides; Paraffin Embedding; Phosphopyruvate Hydratase; Rats; Rats, Wistar; Salicylates; Time Factors; Vimentin

We demonstrated a novel tandem-column micro-gas chromatography (microGC) based on optofluidic ring resonator (OFRR). The OFRR is a thin-walled fused silica capillary whose interior surface is coated with a polymeric stationary phase. The circular cross section of the OFRR forms the micro-ring resonator and supports whispering gallery modes (WGMs). Via tapered optical fibers in contact with the OFRR, the WGM can be excited externally at any positions along the OFRR capillary, thus enabling multi-point, on-column, real-time detection of vapor molecules flowing through the OFRR. In the present OFRR-based tandem-column-based microGC implementation, a 180 cm long conventional GC column coated with a nonpolar stationary phase was followed by a relatively short OFRR column coated with a polar phase. Two detection positions, one at the inlet of the OFRR and the other a few centimeters downstream, were used to monitor the separation achieved by the first and the second column, respectively. Owing to the multi-point on-column detection that provides complementary retention time information on each chemical compound, co-eluted analytes can be well separated and identified on at least one detection channel and no modulation is needed at the interface of tandem columns. Separation and detection of twelve analytes with various volatilities and polarities within four minutes were demonstrated. In addition, the chromatograms obtained from three different locations along the OFRR column demonstrated the system's capability of on-column monitoring of the separation process for the target analyte in a vapor mixture. Our results will lead to the development of a rapid, simple, and portable microGC system with significantly improved selectivity and chemical identification capabilities.

Topics: Alkanes; Chromatography, Gas; Organophosphorus Compounds; Salicylates; Toluene

Nicotine and flavorant compound levels were measured in 10 "mint"-related sub-brands and 8 "wintergreen" sub-brands of smokeless tobacco (SLT). Also analyzed were "mint"-related and "wintergreen" confectionery products. Of the "mint" SLT, "Timberwolf Packs Mint Pouches" contained the highest menthol level (5.3 mg/g); the average for the five most-highly mentholated SLT products was 4.3 mg/g. The average for the most five most-highly mentholated confectionery products was 3.5 mg/g. For hard candy, a reported average of maximum use levels is 2.1 mg/g (Burdock, 2009). Of the "wintergreen" SLT, "Hawken Wintergreen" was found to contain the highest methyl salicylate (MS) level (29.7 mg/g). The average of the five highest SLT MS levels was 23.8 mg/g, i.e., 5x higher than the level found in the confectionery product with the highest MS level (LifeSavers Wint O Green Sugar Free, 4.6 mg/g). For hard candy, a reported average of maximum use levels is 2.0 mg/g (Burdock, 2009). Assuming 23.8 mg/g MS in SLT, SLT use at 15 g/day, 100% bodily absorption of the MS, and 60 kg body weight, the average daily intake would be 6.0 mg/kg-day, i.e., 12x the acceptable daily intake (ADI) of 0.5 mg/kg-day established for this compound by a joint FAO/WHO committee.

Topics: Candy; Flavoring Agents; Mentha; Menthol; Nicotine; Oils, Volatile; Plant Extracts; Salicylates; Tobacco, Smokeless

The role of methyl salicylate (MeSA) production was studied in indirect and direct defence responses of tomato (Solanum lycopersicum) to the spider mite Tetranychus urticae and the root-invading fungus Fusarium oxysporum f. sp. lycopersici, respectively. To this end, we silenced the tomato gene encoding salicylic acid methyl transferase (SAMT). Silencing of SAMT led to a major reduction in SAMT expression and MeSA emission upon herbivory by spider mites, without affecting the induced emission of other volatiles (terpenoids). The predatory mite Phytoseiulus persimilis, which preys on T. urticae, could not discriminate between infested and non-infested SAMT-silenced lines, as it could for wild-type tomato plants. Moreover, when given the choice between infested SAMT-silenced and infested wild-type plants, they preferred the latter. These findings are supportive of a major role for MeSA in this indirect defence response of tomato. SAMT-silenced tomato plants were less susceptible to a virulent strain of F. oxysporum f. sp. lycopersici, indicating that the direct defense responses in the roots are also affected in these plants. Our studies show that the conversion of SA to MeSA can affect both direct and indirect plant defence responses.

Topics: Animals; Fusarium; Gene Expression Regulation, Plant; Gene Silencing; Host-Pathogen Interactions; Methyltransferases; Mite Infestations; Oils, Volatile; Plant Diseases; Plant Proteins; Plant Roots; Plants, Genetically Modified; Predatory Behavior; RNA, Plant; Salicylates; Solanum lycopersicum; Terpenes; Tetranychidae

Catechols are central intermediates in the metabolism of aromatic compounds. Degradation of 4-methylcatechol via intradiol cleavage usually leads to the formation of 4-methylmuconolactone (4-ML) as a dead-end metabolite. Only a few microorganisms are known to mineralize 4-ML. The mml gene cluster of Pseudomonas reinekei MT1, which encodes enzymes involved in the metabolism of 4-ML, is shown here to encode 10 genes found in a 9.4-kb chromosomal region. Reverse transcription assays revealed that these genes form a single operon, where their expression is controlled by two promoters. Promoter fusion assays identified 4-methyl-3-oxoadipate as an inducer. Mineralization of 4-ML is initiated by the 4-methylmuconolactone methylisomerase encoded by mmlI. This reaction produces 3-ML and is followed by a rearrangement of the double bond catalyzed by the methylmuconolactone isomerase encoded by mmlJ. Deletion of mmlL, encoding a protein of the metallo-beta-lactamase superfamily, resulted in a loss of the capability of the strain MT1 to open the lactone ring, suggesting its function as a 4-methyl-3-oxoadipate enol-lactone hydrolase. Further metabolism can be assumed to occur by analogy with reactions known from the 3-oxoadipate pathway. mmlF and mmlG probably encode a 4-methyl-3-oxoadipyl-coenzyme A (CoA) transferase, and the mmlC gene product functions as a thiolase, transforming 4-methyl-3-oxoadipyl-CoA into methylsuccinyl-CoA and acetyl-CoA, as indicated by the accumulation of 4-methyl-3-oxoadipate in the respective deletion mutant. Accumulation of methylsuccinate by an mmlK deletion mutant indicates that the encoded acetyl-CoA hydrolase/transferase is crucial for channeling methylsuccinate into the central metabolism.

Topics: Adipates; Bacterial Proteins; Biodegradation, Environmental; Culture Media; Gene Deletion; Gene Expression Regulation, Bacterial; Hydrocarbons, Aromatic; Isomerases; Lactones; Molecular Structure; Open Reading Frames; Pseudomonas; Salicylates

Most ambulatory victims of a terrorist chemical attack will have exposure to vapor only. The study objective was to measure the duration of chemical vapor release from various types of clothing.. A chemical agent was simulated using methyl salicylate (MeS), which has similar physical properties to sulfur mustard and was the agent used in the U.S. Army's Man-In-Simulant Test (MIST). Vapor concentration was measured with a Smiths Detection Advanced Portable Detector (APD)-2000 unit. The clothing items were exposed to vapor for 1 hour in a sealed cabinet; vapor concentration was measured at the start and end of each exposure. Clothing was then removed and assessed every 5 minutes with the APD-2000, using a uniform sweep pattern, until readings remained 0.. Concentration and duration of vapor release from clothing varied with clothing composition and construction. Lightweight cotton shirts and jeans had the least trapped vapor; down outerwear, the most. Vapor concentration near the clothing often increased for several minutes after the clothing was removed from the contaminated environment. Compression of thick outerwear released additional vapor. Mean times to reach 0 ranged from 7 minutes for jeans to 42 minutes for down jackets.. This simulation model of chemical vapor release demonstrates persistent presence of simulant vapor over time. This implies that chemical vapor may be released from the victims' clothing after they are evacuated from the site of exposure, resulting in additional exposure of victims and emergency responders. Insulated outerwear can release additional vapor when handled. If a patient has just moved to a vapor screening point, immediate assessment before additional vapor can be released from the clothing can lead to a false-negative assessment of contamination.

Topics: Chemical Warfare Agents; Clothing; Decontamination; Humans; Salicylates; Volatilization

Methyl salicylate (MeSA) is a volatile plant secondary metabolite that is an important contributor to taste and scent of many fruits and flowers. It is synthesized from salicylic acid (SA), a phytohormone that contributes to plant pathogen defense. MeSA is synthesized by members of a family of O-methyltransferases. In order to elaborate the mechanism of MeSA synthesis in tomato, we screened a set of O-methyltransferases for activity against multiple substrates. An enzyme that specifically catalyzes methylation of SA, SlSAMT, as well as enzymes that act upon jasmonic acid and indole-3-acetic acid were identified. Analyses of transgenic over- and under-producing lines validated the function of SlSAMT in vivo. The SlSAMT gene was mapped to a position near the bottom of chromosome 9. Analysis of MeSA emissions from an introgression population derived from a cross with Solanum pennellii revealed a quantitative trait locus (QTL) linked to higher fruit methyl salicylate emissions. The higher MeSA emissions associate with significantly higher SpSAMT expression, consistent with SAMT gene expression being rate limiting for ripening-associated MeSA emissions. Transgenic plants that constitutively over-produce MeSA exhibited only slightly delayed symptom development following infection with the disease-causing bacterial pathogen, Xanthomonas campestris pv. vesicatoria (Xcv). Unexpectedly, pathogen-challenged leaves accumulated significantly higher levels of SA as well as glycosylated forms of SA and MeSA, indicating a disruption in control of the SA-related metabolite pool. Taken together, the results indicate that SlSAMT is critical for methyl salicylate synthesis and methyl salicylate, in turn, likely has an important role in controlling SA synthesis.

Topics: Chromosome Mapping; Cloning, Molecular; Methyltransferases; Phylogeny; Plants, Genetically Modified; Quantitative Trait Loci; RNA, Plant; Salicylates; Solanum lycopersicum; Volatile Organic Compounds

At normal conditions there is a substantial water gradient over the skin as it separates the water-rich inside of the body from the dry outside. This leads to a variation in the degree of hydration from the inside to the outside of skin and changes in this gradient may affect its structure and function. In this study we raise the question: How do changes in the water gradient across skin affect its permeability? We approach this problem in novel diffusion experiments that permit strict control of the gradient in the chemical potential of water and hence well-defined boundary conditions. The results demonstrate that a water gradient can be used to regulate transport of drugs with different lipophilic characteristics across the skin barrier. It is shown that the transport of metronidazole (log P(o/w)=0.0) and methyl salicylate (log P(o/w)=2.5) across skin increases abruptly at low water gradients, corresponding to high degrees of skin hydration, and that this effect is reversible. This phenomenon is highly relevant to drug delivery applications due to its potential of temporarily open the skin barrier for transdermal drug delivery and subsequently close the barrier after treatment. Further, the results contribute to the understanding of the occlusion effect and indicate the boundary conditions of the water gradient needed to make use of this effect.

Topics: Animals; Anti-Infective Agents; Biological Transport; Diffusion; Metronidazole; Salicylates; Skin; Swine; Water

It is well documented that when plants are damaged by insects they respond by emitting a range of volatile organic compounds (VOCs). While there have been numerous reports concerning VOCs induced by chewing herbivores, there are relatively few studies detailing the VOCs induced by aphid feeding. The effects of aphid feeding on VOCs emitted by boreal forest trees have been particularly neglected. Herbivore-induced VOCs have relevance to direct and indirect plant defence and atmospheric chemistry. In this study, we analysed the VOCs emitted by Betula pendula (Roth) and Alnus glutinosa (L.) (Gaertn.) infested by specialist aphid species under laboratory conditions. We also complemented this by collecting VOCs from leaf beetle-damaged saplings under field conditions. In addition to induction of some inducible terpenes, we detected substantial aphid-induced emissions of methyl salicylate (MeSA) in both B. pendula and A. glutinosa. MeSA emission intensity depended on the length of aphid infestation. Feeding by beetles induced emission of (E)-DMNT in both tree species and (E)-beta-ocimene in A. glutinosa but had no effect on MeSA emissions. MeSA has been shown to have aphid-repellent qualities and has been shown recently to have impact on formation of secondary organic aerosols in the atmosphere. We discuss our results in relation to these two phenomena.

Topics: Animals; Aphids; Betula; Host-Parasite Interactions; Ilex; Salicylates

Two benzenoid esters, methyl salicylate (MeSA) and methyl benzoate (MeBA), were detected from insect-damaged rice plants. By correlating metabolite production with gene expression analysis, five candidate genes encoding putative carboxyl methyltransferases were identified. Enzymatic assays with Escherichia coli-expressed recombinant proteins demonstrated that only one of the five candidates, OsBSMT1, has salicylic acid (SA) methyltransferase (SAMT) and benzoic acid (BA) methyltransferase (BAMT) activities for producing MeSA and MeBA, respectively. Whereas OsBSMT1 is phylogenetically relatively distant from dicot SAMTs, the three-dimensional structure of OsBSMT1, which was determined using homology-based structural modeling, is highly similar to those of characterized SAMTs. Analyses of OsBSMT1 expression in wild-type rice plants under various stress conditions indicate that the jasmonic acid (JA) signaling pathway plays a critical role in regulating the production and emission of MeSA in rice. Further analysis using transgenic rice plants overexpressing NH1, a key component of the SA signaling pathway in rice, suggests that the SA signaling pathway also plays an important role in governing OsBSMT1 expression and emission of its products, probably through a crosstalk with the JA signaling pathway. The role of the volatile products of OsBSMT1, MeSA and MeBA, in rice defense against insect herbivory is discussed.

Topics: Animals; Benzoates; Cyclopentanes; Escherichia coli; Gene Expression; Genes, Plant; Immunity, Innate; Insecta; Methyltransferases; Molecular Structure; Oryza; Oxylipins; Plant Diseases; Plant Growth Regulators; Plants, Genetically Modified; Recombinant Proteins; Salicylates; Salicylic Acid; Signal Transduction; Stress, Physiological

Methyl salicylate (MeSA) is a common herbivore-induced plant volatile that, when applied to crops, has the potential to enhance natural enemy abundance and pest control. The impacts of MeSA in strawberry were unknown and examined in the spring and midsummer period. Strawberry plots contained no lures (control) or two 30-d MeSA lures (Predalure) in the center: one lure 0.61 m aboveground over a sticky trap, and one lure on a plant near the ground. Arthropod abundance was monitored at the point source, 5 m and 10 m away from lures over 31 d with white sticky traps, pitfall traps, and leaf inspection. Twenty-seven and nine comparisons were made among beneficial and pest arthropods, respectively. Overall positive responses were found among Chrysopidae in July-August 2008 and Orius tristicolor (White) in May-June 2009 to MeSA based on sticky traps. Chrysopidae showed attraction to the point source, but not at 5 m and 10 m. Ground-dwelling predators collected in pitfall traps such as Araneae, the carabid beetles, Pterostichus melanarius (Illiger), and Nebria brevicollis (Fabricius) did not respond. Increased abundance of six natural enemy groups appeared on various dates between 3 and 24 d after placement of lures in the field based on leaf inspection and sticky traps. Conversely, fewer Coccinellidae were captured on sticky traps on days 0-3, and fewer natural enemies were observed on leaves on day 28 in MeSA plots. MeSA did not increase nor decrease pest abundance.

Topics: Animals; Arthropods; Behavior, Animal; Food Chain; Fragaria; Insect Control; Salicylates; Time Factors

The indirect defense mechanisms of plants comprise the production of herbivore-induced plant volatiles that can attract natural enemies of plant attackers. One of the often emitted compounds after herbivory is methyl salicylate (MeSA). Here, we studied the importance of this caterpillar-induced compound in the attraction of the parasitoid wasp Diadegma semiclausum by using a mutant Arabidopsis line. Pieris rapae infested AtBSMT1-KO mutant Arabidopsis plants, compromised in the biosynthesis of MeSA, were more attractive to parasitoids than infested wild-type plants. This suggests that the presence of MeSA has negative effects on parasitoid host-finding behavior when exposed to wild-type production of herbivore-induced Arabidopsis volatiles. Furthermore, in line with this, we recorded a positive correlation between MeSA dose and repellence of D. semiclausum when supplementing the headspace of caterpillar-infested AtBSMT1-KO plants with synthetic MeSA.

Topics: Animals; Arabidopsis; Arabidopsis Proteins; Behavior, Animal; Host-Parasite Interactions; Larva; Methyltransferases; Plants, Genetically Modified; Salicylates; Wasps

Aerosol drugs dominate a significant share of pharmaceutical preparations on the market. A novel sensitive method utilizing nano extractive electrospray ionization mass spectrometry (nanoEESI-MS) has been developed for the rapid analysis of aerosol drug samples with quantitative information. Without any sample pretreatment, aerosol drugs were manually sprayed into the primary ion plume created by a nano electrospray emitter for direct ionization under ambient conditions. The analyte ions of interest were guided into an ion trap mass spectrometer for tandem mass analysis. The active ingredients of various aerosol drugs, such as econazole nitrate, beclomethasone dipropionate, binary mixture of methyl salicylate and diphenhydramine, terbutaline, and salbutamol, were rapidly detected using nanoEESI-MS. A single sample analysis could be completed within 1.2 s. Tandem mass spectrometry was used to confirm the identification of important compounds in each aerosol drug sample. Reasonable relative standard deviation (RSD = 6.39%, n = 13) and acceptable sensitivity (10 ppt, 100 muL) were found for the salbutamol aerosol sample, which suggests that nanoEESI-MS has the quantitative capacity for analyzing complex pharmaceutical samples. This method was further extended to study the thermal decomposition process of salbutamol, showing that the degradation kinetics of salbutamol can be conveniently tracked. Our data demonstrate that nanoEESI tandem mass spectrometry is a fast and sensitive technique for the analysis of aerosol drug preparations, showing promising applications in pharmacology studies and in situ analysis of aerosol drugs on the market.

Topics: Adrenergic beta-Agonists; Albuterol; Anti-Allergic Agents; Anti-Inflammatory Agents; Antifungal Agents; Antirheumatic Agents; Beclomethasone; Diphenhydramine; Econazole; Gases; Nanotechnology; Pharmaceutical Preparations; Salicylates; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry; Terbutaline

Plants infested with herbivores release specific volatile compounds that are known to recruit natural enemies. The response of natural enemies to these volatiles may be either learned or genetically determined. We asked whether there is genetic variation in the response of the predatory mite Phytoseiulus persimilis to methyl salicylate (MeSa). MeSa is a volatile compound consistently produced by plants being attacked by the two-spotted spider mite, the prey of P. persimilis. We predicted that predators express genetically determined responses during long-distance migration where previously learned associations may have less value. Additionally, we asked whether these responses depend on odors from uninfested plants as a background to MeSa. To infer a genetic basis, we analyzed the variation in response to MeSa among iso-female lines of P. persimilis by using choice-tests that involved either (1) MeSa presented as a single compound or (2) MeSa with background-odor from uninfested lima bean plants. These tests were conducted for starved and satiated predators, i.e., two physiological states, one that approximates migration and another that mimics local patch exploration. We found variation among iso-female lines in the responses to MeSa, thus showing genetic variation for this behavior. The variation was more pronounced in the starved predators, thus indicating that P. persimilis relies on innate preferences when migrating. Background volatiles of uninfested plants changed the predators' responses to MeSa in a manner that depended on physiological state and iso-female line. Thus, it is possible to select for context-dependent behavioral responses of natural enemies to plant volatiles.

Topics: Animals; Behavior, Animal; Female; Genetic Variation; Mites; Phaseolus; Salicylates; Tetranychidae; Volatile Organic Compounds

Tobacco SABP2, a 29kDa protein catalyzes the conversion of methyl salicylic acid (MeSA) into salicylic acid (SA) to induce SAR. Pretreatment of plants with acibenzolar-S-methyl (ASM), a functional analog of salicylic acid induces systemic acquired resistance (SAR). Data presented in this paper suggest that SABP2 catalyzes the conversion of ASM into acibenzolar to induce SAR. Transgenic SABP2-silenced tobacco plants when treated with ASM, fail to express PR-1 proteins and do not induce robust SAR expression. When treated with acibenzolar, full SAR is induced in SABP2-silenced plants. These results show that functional SABP2 is required for ASM-mediated induction of resistance.

Topics: Biocatalysis; Esterases; Gene Silencing; Immunity, Innate; Metabolic Networks and Pathways; Nicotiana; Plant Diseases; Plant Leaves; Plant Proteins; Salicylates; Thiadiazoles

Deciduous trees remobilize the nitrogen in leaves during the process of autumn coloration, thus providing a high quality food source for aphids preparing to lay over-wintering eggs. It has been suggested that aphids may use volatile organic compounds (VOCs) to: (a) select leaves where nutrient remobilization has started and induced defenses are reduced; and (b) detect the time of leaf abscission. We analyzed VOCs emitted by the foliage of Betula pendula Roth. during autumn coloration and from leaf litter just after leaf fall. We tested the hypothesis that costly, photosynthesis-related terpenes and other herbivore-induced VOCs related to attraction of aphid parasitoids and predators are reduced during the coloration process. We also investigated if the VOC emission profile of abscising leaves is different from that of early stage yellowing leaves. Enemy-luring compounds (E)-β-ocimene, linalool, and (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) were emitted only from the green foliage. Methyl salicylate (MeSa), known to recruit predatory bugs and attract migrant aphids, was emitted until the first stage of color change. Cis-3-hexenol, an indicator of cellular disintegration, became dominant in the emissions from abscising leaves and from fresh leaf litter. We discuss the ecological significance of the observed changes in birch leaf VOC profiles during the process of autumn senescence.

Topics: Acyclic Monoterpenes; Alkenes; Animals; Aphids; Betula; Ecosystem; Monoterpenes; Photosynthesis; Plant Leaves; Salicylates; Seasons; Terpenes; Time Factors; Volatile Organic Compounds

Syrphid flies are frequent flower visitors, but little is known about the cues they use to find flowers. We determined the importance of visual and olfactory cues in a flight cage bioassay using Cirsium arvense (Asteraceae) flower heads and experienced Episyrphus balteatus (Diptera, Syrphidae). We tested the response of antennae of the flies to headspace inflorescence scent samples by using gas chromatography coupled to electroantennography (GC-EAD). The bioassays revealed that both sexes of experienced flies rely on olfactory, not visual, cues to find C. arvense flower heads. The GC-EAD measurements demonstrated that male and female flies have olfactory receptors for several of the compounds emitted by the inflorescences. These electroantennographic-active compounds may be responsible for the attraction of flies to the C. arvense flower heads. Among the compounds eliciting an antennal response are methyl salicylate and 2-phenylethanol, which were previously described as syrphid attractants. Overall, our study demonstrates for the first time that a syrphid fly uses olfactory and not visual cues to find a pollen/nectar host-plant.

Topics: Animals; Arthropod Antennae; Asteraceae; Behavior, Animal; Chromatography, Gas; Diptera; Female; Flowers; Male; Phenylethyl Alcohol; Salicylates; Smell

Methylsalicylate (MS) is a naturally occurring compound that is used as a major active ingredient of balms and liniments supplied as topical analgesics. Despite the common use of MS as a pain reliever, the underlying molecular mechanism is not fully understood. Here we characterize the action of MS on transient receptor potential V1 (TRPV1). In human embryonic kidney 293 cells expressing human TRPV1 (hTRPV1), MS evoked increases of [Ca(2+)](i), which declined regardless of its continuous presence, indicative of marked desensitization. TRPV1 antagonists dose-dependently suppressed the MS-induced [Ca(2+)](i) increase. MS simultaneously elicited an inward current and increase of [Ca(2+)](i) in the voltage-clamped cells, suggesting that MS promoted Ca(2+) influx through the activation of TRPV1 channels. MS reversibly inhibited hTRPV1 activation by polymodal stimuli such as capsaicin, protons, heat, anandamide, and 2-aminoethoxydiphenyl borate. Because both the stimulatory and inhibitory actions of MS were exhibited in capsaicin- and allicin-insensitive mutant channels, MS-induced hTRPV1 activation was mediated by distinct channel regions from capsaicin and allicin. In cultured rat sensory neurons, MS elicited a [Ca(2+)](i) increase in cells responding to capsaicin. MS significantly suppressed nocifensive behavior induced by intraplantar capsaicin in rats. The present data indicate that MS has both stimulatory and inhibitory actions on TRPV1 channels and suggest that the latter action may partly underlie the analgesic effects of MS independent of inhibition of cyclooxygenases in vivo.

Topics: Analgesics; Animals; Calcium; Capsaicin; Cell Line; Cells, Cultured; Humans; Membrane Potentials; Rats; Salicylates; TRPV Cation Channels

There are currently no accepted biological prediction models for assessing the potential of a substance to cause respiratory sensitization. New tests should be based on mechanistic understanding and should be preferentially restricted to in vitro assays. The major goal of this study was to investigate the alterations in gene expression of human alveolar epithelial (A549) cells after exposure to respiratory sensitizing and non-respiratory sensitizing chemicals, and to identify genes that are able to discriminate between both groups of chemicals. A549 cells were exposed during 6, 10, and 24 h to the respiratory sensitizers ammonium hexachloroplatinate IV, hexamethylene diisocyanate, and trimellitic anhydride, the irritants acrolein and methyl salicylate, and the skin sensitizer 1-chloro-2,4-dinitrobenzene. Overall changes in gene expression were evaluated using Agilent Whole Human Genome 4x44K oligonucleotide arrays. A Fisher linear discriminant analysis was used to obtain a ranking of genes that reflects their potential to discriminate between respiratory sensitizing and respiratory non-sensitizing chemicals. Among the 20 most discriminating genes, which were categorized into molecular and biological gene ontology (GO) terms, CTLA4 could be associated with asthma and/or respiratory sensitization. When categorizing the top-1000 genes into biological GO terms, 22 genes were associated with immune function. Using a pathway analysis tool to identify possible underlying mechanisms of respiratory sensitization, no known canonical signaling pathway was observed to be activated in the A549 cell line.

Topics: Acrolein; Antigens, CD; Cell Line; CTLA-4 Antigen; Dinitrochlorobenzene; Epithelial Cells; Gene Expression Profiling; Genetic Markers; Humans; Pulmonary Alveoli; Salicylates; Signal Transduction

To determine the root canal morphology of mandibular first premolar teeth in an Indian population using a decalcification and clearing technique.. One hundred extracted adult mandibular first premolar teeth were studied following decalcification and clearing. The shape of the canal orifice, root canal pattern and length of the teeth were determined.. The mandibular first premolars were identified to have a round orifice (38%), oval orifice (44%), flattened orifice (17%) and C-shaped orifice (1%). The canal patterns were classified as Type I (72%), Type II (6%), Type III (3%), Type IV (10%) and Type V (8%) according to Vertucci's classification. C-shaped canals were identified in one tooth (1%). The average length of the teeth was 21.6 mm. Fourteen per cent of the teeth had mesial invaginations of the root.. Type I canal patterns were the most frequently occurring in mandibular first premolars amongst the Indian population. 85.7% of the teeth with mesial invagination of the root had either two canals or division of canals.

Topics: Adult; Bicuspid; Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Fixatives; Humans; Imaging, Three-Dimensional; India; Mandible; Odontometry; Salicylates; Tooth Crown; Tooth Root

We previously demonstrated that salicylic acid-binding protein 2 (SABP2) of tobacco is an integral component of systemic acquired resistance (SAR). SABP2 is a methyl salicylate (MeSA) esterase that has high affinity for SA, which feedback inhibits its esterase activity. MeSA esterase activity is required in distal, healthy tissue of pathogen-infected plants to hydrolyze MeSA, which functions as a long-distance, phloem-mobile SAR signal; this hydrolysis releases the biologically active defense hormone SA. In this study, we examined the inhibitory interaction of SA with SABP2, and identified a synthetic SA analog, 2,2,2,2'-tetra-f luoroacetophenone (tetraFA) that, like SA, competitively inhibits the activity of SABP2 and targets esterases, which utilize MeSA as a substrate. However, in contrast to SA, tetraFA does not induce downstream defense responses and, therefore, is effective in planta at blocking SAR development in tobacco mosaic virus (TMV)-infected tobacco and Pseudomonas syringae-infected Arabidopsis. These results confirm the importance of SABP2 and MeSA for SAR development in tobacco and establish similar roles for MeSA and the orthologs of SABP2 in Arabidopsis. Moreover, they demonstrate that tetraFA can be used to determine whether MeSA and its corresponding esterase(s) play a role in SAR signaling in other plant species. In planta analyses using tetraFA, in conjunction with leaf detachment assays and MeSA quantification, were used to assess the kinetics with which MeSA is generated in pathogen-infected leaves, transmitted through the phloem, and processed in the distal healthy leaves. In TMV-infected tobacco, these studies revealed that critical amounts of MeSA are generated, transmitted, and processed between 48 and 72 h post primary infection.

Topics: Arabidopsis; Esterases; Nicotiana; Phloem; Plant Diseases; Plant Proteins; Pseudomonas syringae; Salicylates; Time Factors; Tobacco Mosaic Virus

Topics: Acyl Carrier Protein; Acylation; Acyltransferases; Amino Acid Sequence; Aminoglycosides; Biological Products; Genes, Bacterial; Molecular Sequence Data; Molecular Structure; Multigene Family; Salicylates; Sequence Alignment; Streptomyces antibioticus

Warfarin-drug interactioions, which can result in life-threatening bleeding, are preventable. A 53-year-old man was admitted to hospital with exacerbation of chronic obstructive airways disease, cor pulmonale, pneumonia, deep vein thrombosis and acute pulmonary embolism. His pulmonary thromboemobolism was initially treated by low-molecular-weight-heparin and heparin. After a loading dose of 5 mg for 2 days, warfarin was given in a daily dose of 2 mg. On the fifth day of warfarin therapy, the last dose of Enoxaparin was given in the morning. He had a fall in the bathroom with blunt injury to the right flank. He complained of right thigh numbness and increasing pain and swelling over his right flank and abdomen. A tender mass was noted over the right flank. His Hb level dropped to 9.7 g/dl. His INR increased from 2.46 to 3.49-3.71 one day later. On further questioning, he admitted self applications of 20 g of Analgesic balm (50% methyl salicylate) over his right calf for 3 days. CT scan showed a large right retroperitoneal haematoma and right iliacus intramuscular haematoma. Warfarin was withheld. He was given fresh frozen plasma, packed cells and vitamin K(1). Inferior vena cava filter was inserted. The haematomas were resolving. He was subsequently discharged to convalescence hospital for continuation of anticoagulant therapy and close monitoring. Significant usage of topical methyl salicylate ointment can potentiate the anticoagulant effect of warfarin. The over-anticoagulation and the presence of platelet dysfunction increase the risk of severe bleeding, which can be provoked by trauma.

Topics: Anticoagulants; Drug Interactions; Hemorrhage; Humans; International Normalized Ratio; Male; Middle Aged; Partial Thromboplastin Time; Retroperitoneal Space; Salicylates; Warfarin

Moths recognize a wide range of volatile compounds, which they use to locate mates, food sources, and oviposition sites. These compounds are recognized by odorant receptors (OR) located within the dendritic membrane of sensory neurons that extend into the lymph of sensilla, covering the surface of insect antennae. We have identified 3 genes encoding ORs from the tortricid moth, Epiphyas postvittana, a pest of horticulture. Like Drosophila melanogaster ORs, they contain 7 transmembrane helices with an intracellular N-terminus, an orientation in the plasma membrane opposite to that of classical GPCRs. EpOR2 is orthologous to the coreceptor Or83b from D. melanogaster. EpOR1 and EpOR3 both recognize a range of terpenoids and benzoates produced by plants. Of the compounds tested, EpOR1 shows the best sensitivity to methyl salicylate [EC(50) = 1.8 x 10(-12) M], a common constituent of floral scents and an important signaling compound produced by plants when under attack from insects and pathogens. EpOR3 best recognizes the monoterpene citral to low concentrations [EC(50) = 1.1 x 10(-13) M]. Citral produces the largest amplitude electrophysiological responses in E. postvittana antennae and elicits repellent activity against ovipositing female moths. Orthologues of EpOR3 were found across 6 families within the Lepidoptera, suggesting that the ability to recognize citral may underpin an important behavior.

Topics: Acyclic Monoterpenes; Amino Acid Sequence; Animals; Female; Gene Expression Profiling; Molecular Sequence Data; Moths; Phylogeny; Receptors, Odorant; Salicylates; Sequence Alignment; Terpenes; Volatile Organic Compounds

Systemic acquired resistance (SAR) develops in response to local microbial leaf inoculation and renders the whole plant more resistant to subsequent pathogen infection. Accumulation of salicylic acid (SA) in noninfected plant parts is required for SAR, and methyl salicylate (MeSA) and jasmonate (JA) are proposed to have critical roles during SAR long-distance signaling from inoculated to distant leaves. Here, we address the significance of MeSA and JA during SAR development in Arabidopsis thaliana. MeSA production increases in leaves inoculated with the SAR-inducing bacterial pathogen Pseudomonas syringae; however, most MeSA is emitted into the atmosphere, and only small amounts are retained. We show that in several Arabidopsis defense mutants, the abilities to produce MeSA and to establish SAR do not coincide. T-DNA insertion lines defective in expression of a pathogen-responsive SA methyltransferase gene are completely devoid of induced MeSA production but increase systemic SA levels and develop SAR upon local P. syringae inoculation. Therefore, MeSA is dispensable for SAR in Arabidopsis, and SA accumulation in distant leaves appears to occur by de novo synthesis via isochorismate synthase. We show that MeSA production induced by P. syringae depends on the JA pathway but that JA biosynthesis or downstream signaling is not required for SAR. In compatible interactions, MeSA production depends on the P. syringae virulence factor coronatine, suggesting that the phytopathogen uses coronatine-mediated volatilization of MeSA from leaves to attenuate the SA-based defense pathway.

Topics: Amino Acids; Arabidopsis; Arabidopsis Proteins; Bacterial Toxins; Cyclopentanes; Immunity, Innate; Indenes; Oxylipins; Plant Leaves; Pseudomonas syringae; Salicylates; Signal Transduction

In field trapping tests, the catch of Chrysoperla carnea sensu lato (Neuroptera: Chrysopidae) increased when acetic acid was added to lures with phenylacetaldehyde. The addition of methyl salicylate to the binary mixture of phenylacetaldehyde plus acetic acid increased catches even further. The ternary blend proved to be more attractive than beta-caryophyllene, 2-phenylethanol, or 3-methyl eugenol (compounds previously described as attractants for chrysopids) on their own, and no influence on catches was recorded when these compounds were added as fourth components to the ternary blend. There were minimal changes in activity when (E)-cinnamaldehyde or methyl anthranylate (both evoking large responses from female or male antennae of C. carnea in this study) were added, although both compounds showed significant attraction on their own when compared to unbaited traps. In subtractive field bioassays with the ternary mixture, it appeared that the presence of either phenylacetaldehyde or methyl salicylate was important, whereas acetic acid was less so in the ternary mixture. The ternary blend attracted both female and male lacewings at sites in southern, central, and northern Europe. Possible applications of a synthetic attractant for lacewings are discussed.

Topics: Acetaldehyde; Acetic Acid; Animals; Female; Insect Control; Insecta; Male; Salicylates; Sex Attractants

Topics: Animals; Ants; Behavior, Animal; Fabaceae; Hexobarbital; Plant Extracts; Plant Leaves; Salicylates; Symbiosis

The European grape berry moth is an important pest in vineyards. Males respond to the female-produced sex pheromone released from a piezo nebulizer in a dose-dependent manner in a wind tunnel: <50% arrive at the source at 5-50 pg/min (underdosed), 80% arrive at 100 pg/min to 10 ng/min (optimal) and <20% arrive at 100 ng/min (overdosed). Males responding to overdosed pheromone show in flight arrestment at 80 cm from the source. Host plant chemostimuli for Eupoecilia ambiguella increase the responses of males to underdosed and overdosed pheromone. (Z)-3-hexen-1-ol, (+)-terpinen-4-ol, (E)-beta-caryophyllene and methyl salicylate released with the underdosed pheromone cause a significant increase in male E. ambiguella flying to the source. Time-event analysis indicates a positive correlation between faster activation and probability of source contact by the responding males. The four host plant compounds added to the overdosed pheromone permitted males to take off faster and with a higher probability of flying to the source. This suggests that perception of host plant products with the sex pheromone facilitates male E. ambiguella to locate females on host plants, lending credence to the hypothesis that plant products can signal rendezvous sites suitable for mating.

Topics: Animals; Female; Flight, Animal; Hexanols; Host-Parasite Interactions; Male; Moths; Odorants; Organic Chemicals; Polycyclic Sesquiterpenes; Salicylates; Sesquiterpenes; Sex Attractants; Sexual Behavior, Animal; Smell; Terpenes; Time Factors; Vitis; Volatilization

We reported previously that overexpression of a salicylic acid (SA) methyltransferase1 gene from rice (OsBSMT1) or a SA glucosyltransferase1 gene from Arabidopsis thaliana (AtSAGT1) leads to increased susceptibility to Pseudomonas syringae due to reduced SA levels. To further examine their roles in the defense responses, we assayed the transcript levels of AtBSMT1 or AtSAGT1 in plants with altered levels of SA and/or other defense components. These data showed that AtSAGT1 expression is regulated partially by SA, or non-expressor of pathogenesis related protein1, whereas AtBSMT1 expression was induced in SA-deficient mutant plants. In addition, we produced the transgenic Arabidopsis plants with RNAi-mediated inhibition of AtSAGT1 and isolated a null mutant of AtBSMT1 and then analyzed their phenotypes. A T-DNA insertion mutation in the AtBSMT1 resulted in reduced methyl salicylate (MeSA) levels upon P. syringae infection. However, accumulation of SA and glucosyl SA was similar in both the atbsmt1 and wild-type plants, indicating the presence of another SA methyltransferase or an alternative pathway for MeSA production. The AtSAGT1-RNAi line exhibited no altered phenotypes upon pathogen infection, compared to wild-type plants, suggesting that (an)other SA glucosyltransferase(s) in Arabidopsis plants may be important for the pathogenesis of P. syringae.

Topics: Arabidopsis; Arabidopsis Proteins; Blotting, Northern; Gene Expression Profiling; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Glucosyltransferases; Host-Pathogen Interactions; Immunity, Innate; Methyltransferases; Molecular Structure; Mutation; Plant Diseases; Plants, Genetically Modified; Pseudomonas syringae; RNA Interference; Salicylates; Salicylic Acid

Energetics and vibrational analysis study of six isomers of methyl salicylate in their singlet ground state and first excited triple state is put forward in this work at the density functional theory level and large basis sets. The ketoB isomer is the lowest energy isomer, followed by its rotamer ketoA. For both ketoB and ketoA their enolized tautomers are found to be stable as well as their open forms that lack the internal hydrogen bond. The calculated vibrational spectra are in excellent agreement with IR experiments of methyl salicylate in the vapor phase. It is demonstrated that solvent effects have a weak influence on the stability of these isomers. The ionization reaction from ketoB to ketoA shows a high barrier of 0.67 eV ensuring that thermal and chemical equilibria yield systems containing mostly the ketoB isomer at normal conditions.

Topics: Computer Simulation; Isomerism; Models, Chemical; Salicylates; Spectrophotometry, Infrared; Thermodynamics; Vibration

Ca(2+) plays a critical role as second messenger in the signal-response coupling of plant defence responses, and methyl-jasmonate and methyl-salicylate are important components of signal transduction cascades activating plant defences. When intact axenic non-induced seedling roots of sunflower were treated with different Ca(2+) concentrations up to 1 mM, there was no significant increase in O(2)(*-) generation or DMAB-MBTH peroxidase (extracellular, ECPOX) activities in the apoplast, probably because these roots had enough Ca(2+) in their exo- and endocellular reservoirs. Both activities were strongly inhibited by the RBOH-NADPH oxidase inhibitor DPI and by the Ca(2+) surrogate antagonist La(3+), but the voltage-dependent Ca(2+) channel blocker verapamil was only inhibitory at concentrations higher than those active on animal L-type Ca(2+) channels. Concentrations >5 mM EGTA (chelating Ca(2+) in the apoplast) and Li(+) (inhibiting PI cycle dependent endogenous Ca(2+) fluxes) also inhibited both activities. W7, inhibitor of binding of Ca-CaM to its target protein, enhanced both activities, but the inactive analogue W5 showed a similar effect. Our data suggest that Ca(2+) from exocellular and, to a lesser extent, from endocellular stores is involved in oxidative activities, and that RBOH-NADPH oxidase is the main system supporting them. Ca(2+) activation of the PM cytosolic side of RBOH-NADPH oxidase is probably the key to Ca(2+) involvement in these processes. Roots induced by MeJA or MeSA showed significant enhancement of both oxidative activities, as corresponding to the oxidative burst evoked by the two phytohormones in the root apoplast. But while ECPOX activity showed a response to the effectors similar to that described above for non-induced roots, O(2)(*-) generation activity in the apoplast of induced roots was insensitive to EGTA, verapamil and Li(+), the inhibitors of exogenous and endogenous Ca(2+) fluxes; only DPI and La(3+) were inhibitory. As exogenously added 0.1 mM Ca(2+) also increased O (2) (.-) generation, we propose that, in these roots, activation of RBOH-NADPH oxidase by Ca(2+) could be regulated by Ca(2+) sensors in the apoplast.

Topics: Acetates; Calcium Signaling; Cyclopentanes; Helianthus; Oxidation-Reduction; Oxylipins; Plant Roots; Reactive Oxygen Species; Salicylates

During mating in many butterfly species, males transfer spermatophores that contain anti-aphrodisiacs to females that repel conspecific males. For example, males of the large cabbage white, Pieris brassicae (Lepidoptera: Pieridae), transfer the anti-aphrodisiac, benzyl cyanide (BC) to females. Accessory reproductive gland (ARG) secretion of a mated female P. brassicae that is deposited with an egg clutch contains traces of BC, inducing Brussels sprouts plants (Brassica oleracea var. gemmifera) to arrest certain Trichogramma egg parasitoids. Here, we assessed whether deposition of one egg at a time by the closely related small cabbage white, Pieris rapae, induced B. oleracea var. gemmifera to arrest Trichogramma wasps, and whether this plant synomone is triggered by substances originating from male P. rapae seminal fluid. We showed that plants induced by singly laid eggs of P. rapae arrest T. brassicae wasps three days after butterfly egg deposition. Elicitor activity was present in ARG secretion of mated female butterflies, whereas the secretion of virgin females was inactive. Pieris rapae used a mixture of methyl salicylate (MeSA) and indole as an anti-aphrodisiac. We detected traces of both anti-aphrodisiacal compounds in the ARG secretion of mated female P. rapae, whereas indole was lacking in the secretion of virgin female P. rapae. When applied onto the leaf, indole induced changes in the foliar chemistry that arrested T. brassicae wasps. This study shows that compounds of male seminal fluid incur possible fitness costs for Pieris butterflies by indirectly promoting egg parasitoid attack.

Topics: Animals; Aphrodisiacs; Brassica; Butterflies; Ejaculation; Female; Indoles; Male; Olfactory Perception; Ovum; Pheromones; Plant Leaves; Risk; Salicylates; Sexual Behavior, Animal; Wasps

A palm portable mass spectrometer (PPMS) has been developed with a weight of 1.48 kg (3 lb) and a size of 1.54 L (8.2 x 7.7 x 24.5 cm(3)) that can be operated with an average battery power of 5 W. A miniaturized ion trap has been used as a mass analyzer that consists of four parallel disks with coaxial holes. A rf voltage of 1500 V(p-p) at 3.9 MHz has been used for scanning ion mass of up to m/z 300. An ion-getter pump serves for high vacuum of the PPMS. Sample gas was introduced in pulse mode. An embedded microcomputer has been developed for system control. Detection of organic gases diluted in the air has been demonstrated up to 6 ppm for toluene and 22 ppm for dimethyl methylphosphonate (DMMP). Performance results suggest usefulness of the PPMS as a personal mobile device for detection/identification of chemical warfare agents in the field.

Topics: Air; Algorithms; Chemical Warfare Agents; Electric Power Supplies; Electronics; Ions; Mass Spectrometry; Miniaturization; Organophosphorus Compounds; Reproducibility of Results; Salicylates; Software; Tetrachloroethylene; Toluene; Vacuum Curettage

The complex anatomy of the mammalian cochlea is most readily understood by representation in three-dimensions. However, the cochlea is often sectioned to minimize the effects of its anatomic complexity and optical properties on image acquisition by light microscopy. We have found that optical aberrations present in the decalcified cochlea can be greatly reduced by dehydration through graded ethanols followed by clearing with a mixture of five parts methyl salicylate and three parts benzyl benzoate (MSBB). Clearing the cochlea with MSBB enables acquisition of high-resolution images with multiple fluorescent labels, through the full volume of the cochlea by laser scanning confocal microscopy. The resulting images are readily applicable to three-dimensional morphometric analysis and volumetric visualizations. This method promises to be particularly useful for three-dimensional characterization of anatomy, innervation and expression of genes or proteins in the many new animal models of hearing and balance generated by genetic manipulation. Furthermore, the MSBB is compatible with most non-protein fluorophores used for histological labeling, and may be removed with traditional transitional solvents to allow subsequent epoxy embedding for sectioning.

Topics: Animals; Benzoates; Cochlea; Fluorescent Dyes; Hair Cells, Auditory, Inner; Hair Cells, Auditory, Outer; Histological Techniques; Imaging, Three-Dimensional; Immunohistochemistry; Mice; Mice, Inbred CBA; Microscopy, Confocal; Models, Anatomic; Salicylates

Salicylic acid-binding protein 2 (SABP2) is essential for the establishment of systemic acquired resistance (SAR) in tobacco; SABP2's methyl salicylate (MeSA) esterase activity is required in healthy systemic tissues of infected plants to release the active defense phytohormone SA from MeSA, which serves as a long-distance signal for SAR. In the current study, we characterize a new gene family from Arabidopsis thaliana encoding 18 potentially active alpha/beta fold hydrolases that share 32-57% identity with SABP2. Of 14 recombinant AtMES (MES for methyl esterase) proteins tested, five showed preference for MeSA as a substrate and displayed SA inhibition of MeSA esterase activity in vitro (AtMES1, -2, -4, -7, and -9). The two genes encoding MeSA esterases with the greatest activity, AtMES1 and -9, as well as AtMES7 were transcriptionally upregulated during infection of Arabidopsis with avirulent Pseudomonas syringae. In addition, conditional expression of AtMES1, -7, or -9 complemented SAR deficiency in SABP2-silenced tobacco, suggesting that these three members of the AtMES family are SABP2 functional homologs (orthologs). Underexpression by knockout mutation and/or RNAi-mediated silencing of multiple AtMES genes, including AtMES1, -2, -7, and -9, compromised SAR in Arabidopsis and correlated with enhanced accumulation of MeSA in the systemic tissue of SAR-induced plants. Together, the data show that several members of the AtMES gene family are functionally homologous to SABP2 and redundant for MeSA hydrolysis and probably SAR. These data suggest that MeSA is a conserved SAR signal in Arabidopsis and tobacco.

Topics: Arabidopsis; Arabidopsis Proteins; Esterases; Gene Expression Regulation, Plant; Genetic Complementation Test; Immunity, Innate; Multigene Family; Nicotiana; Plant Proteins; Plants, Genetically Modified; Pseudomonas syringae; Reverse Transcriptase Polymerase Chain Reaction; RNA Interference; RNA, Plant; Salicylates; Substrate Specificity; Transformation, Genetic; Transgenes

The complexation of methyl salicylate (MS) and ethyl salicylate (ES), non-steroidal analgesic, anti-inflammatory and antirrheumatic drugs with beta-cyclodextrin (betaCD) has been studied from thermodynamic and structural points of view. The complexation with betaCD has been investigated using reversed-phase liquid chromatography. Retention behavior has been analyzed on a reverse-phase column Luna 18(2) 5 microm. The mobile-phase was methanol:water in different ratios (55:45 to 70:30) in which betaCD (1-9 mM) was incorporated as a mobile-phase additive. The decrease in retention times with increasing concentrations of betaCD enables the determination of the apparent stability constant of the complexes. Values at 30 degrees C with 55% methanol were K(MS:betaCD): 15.84 M(-1) and K(ES:betaCD): 12.73 M(-1) for MS and ES, respectively. The apparent stability constants decrease as the polarity of the solvent decreases. The low solubility of MS and ES in aqueous solution has been improved by complexation with betaCD (1-9 mM). The stability constants of the complexes obtained from the phase-solubility diagrams using a UV-vis spectrophotometric method were K(MS:betaCD): 229 M(-1) and K(ES:betaCD): 166 M(-1). In addition, semi-empirical quantum mechanics calculations using AM1 and PM3 methods in vacuum were performed. The energetically favorable inclusion structures were identified and the most favorable orientation for the inclusion process was found to be the head-down orientation for both complexes. Enthalpy for encapsulation processes was found to be favorable (DeltaH degrees <0), while entropy (DeltaS degrees <0) and Gibbs free energy were unfavorable (DeltaG degrees >0). By means of HPLC and UV-vis measurements and quantum mechanics calculations, it was found that MS and ES form a 1:1 inclusion complex with betaCD. The theoretical results are in agreement with the experimental parameters associated with the encapsulation process.

Topics: Antirheumatic Agents; beta-Cyclodextrins; Chromatography, High Pressure Liquid; Kinetics; Models, Molecular; Quantum Theory; Salicylates; Solubility; Spectrophotometry, Ultraviolet; Temperature; Thermodynamics

Methyl salicylate (MeS) is used as a chemical warfare agent simulant to test chemical protective garments and other individual personal protective gear. The accurate and real-time detection of this analyte is advantageous for various testing regimes. This paper reports the results of MeS vapor exposures on polymer-filled capacitance-based sensors at temperatures ranging from 15 degrees C to 50 degrees C under dry and humid conditions. Multiple capacitors were arranged in an array on a silicon chip each having a different sorptive polymer. The sensors used parallel-plate electrode geometry to measure the dielectric permittivity changes of each polymer when exposed to water and MeS vapor. Of the four polymers tested against MeS, the optimal polymer displayed near or sub-parts-per-million detection limits at 35 degrees C (0-80%RH).

Topics: Biosensing Techniques; Chemical Warfare Agents; Chemistry Techniques, Analytical; Electrochemistry; Equipment Design; Microchemistry; Polymers; Salicylates; Solvents; Temperature; Volatilization; Water

Many drug products that are applied onto the skin contain menthol. Menthol plays a dual role in the analgesic and anti-inflammatory drugs: it causes cooling and local anesthetic effects and, being a penetration enhancer, it increases the skin permeation of the drug substances. However, there are no data concerning the skin penetration of menthol after its application in the most commonly used vehicles and in the presence of drug substances. Therefore, this study evaluated the ex vivo skin disposition of menthol after application of the commercially available drug products containing aluminum acetotartrate, methyl salicylate, ibuprofen and naproxen, using full human-skin mounted in flow-through diffusion cells. After 15, 30 and 60 min of application, the skin was progressively tape-stripped into three fractions of stratum corneum and the remaining epidermis with dermis. The content of menthol in the skin layers was determined by GC method. Varying degrees of penetration of menthol into the skin layers was observed, depending on its amount in the vehicle and the presence of drug substance. In the presence of aluminum acetotartrate, the skin penetration of menthol was limited only to the outer fraction of the stratum corneum. In the case of drug products containing naproxen, the concentration of the drug substance significantly influenced the skin penetration of menthol.

Topics: Adult; Epidermis; Female; Humans; Ibuprofen; Menthol; Middle Aged; Naproxen; Salicylates; Skin; Tartrates

The aim of the present study was to test the possibility of different antigens detection in the biological objects after their storage in methylsalicylate for two or more years before embedding in paraffin, using routine immunocytochemical methods. Using immunocytochemical reactions demostrating intermediate filaments nestin, vimentin, and GFAP, as well as neuronal markers NeuN, neuron-specific enolase, and doublecortin, as the examples, it was shown that long-term storage in methylsalicylate does not prevent immunocytochemical detection of these antigens.

Topics: Animals; Antigens; Astrocytes; Biomarkers; Brain; Desiccation; Doublecortin Protein; Embryo, Mammalian; Immunohistochemistry; Neurons; Paraffin Embedding; Rats; Salicylates

The cabbage moth, Mamestra brassicae L. (Lepidoptera, Noctuidae), is a polyphagous species that is often choosing plants of Brassica as hosts for oviposition. In the search for biologically relevant odorants used by these moths, gas chromatography linked to electrophysiological recordings from single receptor neurons (RNs) has been employed, resulting in classification of distinct types of neurons. This study presents specific olfactory RNs responding to methyl salicylate (MeS) as primary odorant and showing a weak response to methyl benzoate, the 2 aromatic compounds occurring together in several plant species. In 2 cases, the neuron was colocated with another RN type responding to 6 green leaf volatiles: 1-hexanol, (3Z)-hexen-1-ol, (2E)-hexen-1-ol, (3Z)-hexenyl acetate, (2Z)-hexen-1-ol, and an unidentified compound. Whereas the specific RNs detected the minor amounts of MeS in some plants, the compound was not found by gas chromatography linked to mass spectrometry in intact plants, but it was found after herbivore attack. The behavioral effect of MeS was studied in outdoor test arenas with Brassica napus and artificial plants. These experiments indicated that mated M. brassicae females avoid plants with dispensers emitting MeS. As it is induced by caterpillar feeding, this compound may mediate a message to mated M. brassicae females that the plant is already occupied.

Topics: Acetates; Action Potentials; Animals; Arabidopsis; Benzoates; Brassica; Brassica napus; Chromatography, Gas; Electrophysiology; Female; Hexanols; Male; Moths; Odorants; Olfactory Receptor Neurons; Oviposition; Salicylates; Sexual Behavior, Animal

We reported previously that a recombinant salicylic acid (SA) glucosyltransferase1 (AtSGT1) from Arabidopsis thaliana catalyzes the formation of both SA 2-O-beta-D-glucoside (SAG) and the glucose ester of SA (SGE). Here, transgenic Arabidopsis plants overexpressing AtSGT1 have been constructed, and their phenotypes analyzed. Compared to wild-type plants, transgenic plants showed an increased susceptibility to Pseudomonas syringae and reduced the accumulation levels of both free SA and its glucosylated forms (SAG and SGE). On the other hand, the overexpression increased the levels of methyl salicylate (MeSA) and methyl salicylate 2-O-beta-D-glucoside (MeSAG), and also induced SA carboxyl methyltransferase1 (AtBSMT1) expression, whose products catalyze the conversion of SA to MeSA. Our data indicate that reduced resistance by AtSGT1 overexpression results from a reduction in SA content, which is at least in part caused by increases in MeSAG and MeSA levels at the expense of SA. Our study also suggests that genetic manipulation of AtSGT1 can be utilized as an important regulatory tool for pathogen control.

Topics: Arabidopsis; Arabidopsis Proteins; Blotting, Northern; Enzyme Activation; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Genetic Predisposition to Disease; Glucosides; Glucosyltransferases; Plant Diseases; Plant Leaves; Pseudomonas syringae; Salicylates; Salicylic Acid

A total of 139 extracted mandibular second molars were injected with India ink and demineralized. They were made clear and transparent with methyl salicylate, and the anatomy of their canals was studied. It was found that 86.3% of mandibular second molars had two roots, 9.3% had one root, and 4.3% had three roots. Ninety percent of the mesial roots of the mandibular second molars with two roots had two canals (predominantly with a type II or III configuration), and 77.5% of the distal roots of these teeth had one canal (predominantly with a type I configuration). Among the mandibular second molars, 7.2% had C-shaped canals and these configurations were seen mostly in single-rooted mandibular second molars. The results of this study indicate that mandibular second molar teeth have many variations in the number of roots and the morphology of their canals. Therefore it should not be assumed that all mandibular second molar teeth have two roots and three canals.

Topics: Carbon; Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Ethanol; Fixatives; Humans; Iran; Mandible; Molar; Salicylates; Solvents; Tooth Root

An investigation was made in winter wheat fields to study the effects of applying wheat synomones methyl salicylate and sulcatone (6-methy-5-hepten-2-one) on the dynamic changes of Macrosiphum avenae and its natural enemies Harmonia axyridis and Aphidius avenae. The results showed that wheat synomones didn' t change the population dynamics of M. avenae significantly, but had a significant effect on the reduction of M. avenae population number. The synomones could deteriorate the existent environment of M. avenae, and make the number of alatae increased obviously. Although synomones decreased the species richness, diversity index, and evenness of natural enemy communities, the numbers of dominant natural enemy species such as A. avenae and H axyridis were increased. Applying wheat synomones was helpful to the control of M. avenae in winter wheat fields.

Topics: Animals; Aphids; Ecosystem; Pest Control, Biological; Pheromones; Population Dynamics; Predatory Behavior; Salicylates; Seasons; Triticum

Commercial formulations of non-steroidal anti-inflammatory drugs (NSAIDs) are developed for human use but the extent to which they will pass through equine skin is unknown. Skin was harvested from five Thoroughbred geldings from the thorax, groin and leg (dorsal metacarpal) regions and frozen (-20 degrees C) until required. Two grams of methylsalicylate (MeSa) gel was applied to defrosted full-thickness samples in diffusion cells and the penetration of MeSa and its active metabolite, salicylate (Sa), through skin samples were measured over 24 h. Significantly higher (P < or = 0.02) total salicylate (AUC; MeSa + Sa) penetrated through skin from the leg region (5491.3 h mg/L), compared to thorax (3710.7 h mg/L) and groin (3571.5 h mg/L). In addition, there was a significantly higher (P0.01) rate of penetration of total Sa through leg skin in the first 6h after application. It was concluded that the commercial formulation of MeSa would achieve therapeutic levels of total salicylate beneath sites of topical application, with a faster and more pronounced response through the leg region, compared to the upper body.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Diffusion; Horses; Male; Salicylates; Skin

The IR and Raman spectra of methyl salicylate (MS) were recorded and analysed. Surface enhanced Raman scattering (SERS) spectrum was recorded in silver colloid. The vibrational wave numbers of the compound have been computed using the Hartree-Fock/6-31G* basis and compared with the experimental values. SERS studies suggest a flat orientation of the molecule at the metal surface.

Topics: Salicylates; Scattering, Radiation; Spectrophotometry, Infrared; Spectrum Analysis, Raman; Vibration

The species of the genus Palicourea (Rubiaceae family) is well-known for its toxicity towards animals, particularly livestock. This work reports the occurrence of skin irritation during the manipulation of Palicourea longiflora, considering the prevalence of the monofluoracetic acid (MFAA) and another toxic compound: methyl salicylate. The MFAA was identified by 19F-NMR and methyl salicylate by gas chromatography linked to mass spectrometry (GC/MS) analysis. Additionally, an anatomical study of leaves had been used to explain the mechanism of penetration of the toxic principles.

Topics: Animals; Brazil; Calcium Oxalate; Crystallization; Gas Chromatography-Mass Spectrometry; Humans; Irritants; Plant Extracts; Plant Leaves; Rats; Rubiaceae; Salicylates

We cloned a salicylic acid/benzoic acid carboxyl methyltransferase gene, OsBSMT1, from Oryza sativa. A recombinant OsBSMT1 protein obtained by expressing the gene in Escherichia coli exhibited carboxyl methyltransferase activity in reactions with salicylic acid (SA), benzoic acid (BA), and de-S-methyl benzo(1,2,3)thiadiazole-7-carbothioic acid (dSM-BTH), producing methyl salicylate (MeSA), methyl benzoate (MeBA), and methyl dSM-BTH (MeBTH), respectively. Compared to wild-type plants, transgenic Arabidopsis overexpressing OsBSMT1 accumulated considerably higher levels of MeSA and MeBA, some of which were vaporized into the environment. Upon infection with the bacterial pathogen Pseudomonas syringae or the fungal pathogen Golovinomyces orontii, transgenic plants failed to accumulate SA and its glucoside (SAG), becoming more susceptible to disease than wild-type plants. OsBSMT1-overexpressing Arabidopsis showed little induction of PR-1 when treated with SA or G. orontii. Notably, incubation with the transgenic plant was sufficient to trigger PR-1 induction in neighboring wild-type plants. Together, our results indicate that in the absence of SA, MeSA alone cannot induce a defense response, yet it serves as an airborne signal for plant-to-plant communication. We also found that jasmonic acid (JA) induced AtBSMT1, which may contribute to an antagonistic effect on SA signaling pathways by depleting the SA pool in plants.

Topics: Amino Acid Sequence; Arabidopsis; Ascomycota; Cloning, Molecular; Cyclopentanes; Immunity, Innate; Methyltransferases; Molecular Sequence Data; Oryza; Oxylipins; Plant Proteins; Plants, Genetically Modified; Pseudomonas syringae; Recombinant Proteins; Salicylates; Salicylic Acid; Sequence Alignment

Methyl jasmonate (MeJA) and methyl salicylate (MeSA) are important signaling molecules that induce plant defense against insect herbivores and microbial pathogens. We tested the hypothesis that allelopathy is an inducible defense mechanism, and that the JA and SA signaling pathways may activate allelochemicals release. Exogenous application of MeJA and MeSA to rice (Oryza sativa L.) enhanced rice allelopathic potential and led to accumulation of phenolics, an increase in enzymatic activities, and gene transcription of phenylalanine ammonia-lyase (PAL) and cinnamate 4-hydroxylase (C4H), two key enzymes in the phenylpropanoid pathway. Aqueous extracts of the leaves of rice IAC165, a putative allelopathic variety, treated with MeSA (5 mM) or MeJA (0.05 mM), showed increased inhibitory effects (25 and 21%, respectively) on root growth of barnyardgrass (Echinochloa crus-galli L.), and increased inhibitory effects (18 and 23%, respectively) on shoot growth. Aqueous extracts from leaves of Huajingxian 1 rice, a putative nonallelopathic variety treated with MeJA and MeSA, caused 63 and 24% inhibition of root growth in barnyardgrass seedlings. The root exudates of both IAC165 and Huajingxian 1 plants treated with MeJA and MeSA for 48 hr also showed significant increases in their inhibitory effects on root growth of barnyardgrass seedlings. At the four-leaf stage, levels of 3,4-hydroxybenzoic acid, vanillic acid, coumaric acid, and ferulic acid that accumulated in the leaves were 5.3-, 31.3-, 2.2-, and 1.7-fold higher in response to MeJA exposure, and 3.3-, 13.1-, 2.0-, and 2.2-fold higher in response to MeSA. Treatments of MeSA and MeJA enhanced the PAL activity in the rice leaves up to 52.3 and 80.1%, respectively, whereas C4H activity was increased by 40.2 and 67%. Gene transcription of PAL and C4H in rice leaves significantly increased after the plants were subjected to treatment with MeJA and MeSA. These results suggest that allelopathy may be an active defense mechanism, and that plant signaling compounds are potentially valuable in its regulation.

Topics: Acetates; Carboxylic Acids; Cyclopentanes; Echinochloa; Oryza; Oxylipins; Phenylalanine Ammonia-Lyase; Pheromones; Plant Extracts; Plant Leaves; Plant Roots; Plant Shoots; Plant Stems; Salicylates; Trans-Cinnamate 4-Monooxygenase

The tick Boophilus microplus is the principal species of ectoparasite that impairs dairy cattle productivity in Brazil. Its control is mainly by using synthetic chemical products during its parasitic phase. The purpose of this study is to evaluate the acaricide activity of four products of natural origin. Depending on solubility, tests were conducted with solutions in distilled water or emulsified in aqueous DMSO at 1% of the following products: thymol, menthol, methyl salicylate, and salicylic acid. Each of these was tested at three concentrations (0.25, 0.5, and 1.0%) with five repetitions. The "larval packet test" was performed on approximately 100 larvae of B. microplus at around 15 days of age. After applying the test substances, the envelopes were kept at 27 degrees C and UR >80% and opened after 24 h to count the living and dead larvae. Of the four products tested, only thymol caused significant (up to 100%) mortality of B. microplus larvae. The mortality caused by the other products varied from 0.52 to 9.76%. Hence, thymol can be considered a potential agent to control bovine ticks.

Topics: Animals; Cattle; Insecticides; Ixodidae; Larva; Menthol; Salicylates; Salicylic Acid; Thymol

In vitro tests with fresh dermatomed (0.3 to 0.4 mm thick) female breast skin and one leg skin specimen were conducted in Bronaugh flow-through Teflon diffusion cells with three chemicals used to simulate chemical warfare agents: 14C-radiolabeled methyl salicylate (MES), ethyl parathion (PT), and malathion (MT), at three dose levels (2, 20, and 200 mM). Tests were conducted at a skin temperature of 29 degrees C using a brief 30-min exposure to the chemical and a 6.5-h receivor collection period. Rapid absorption of all three chemicals was observed, with MES absorbed about 10-fold faster than PT and MT. For MES, PT, and MT, respectively, there was 32%, 7%, and 12% absorption into the receivor solution (Hank's HEPES buffered saline with 4% bovine serum albumin [BSA], pH 7.4) at the low dose (2 mM), 17%, 2%, and 3% at the medium dose (20 mM), and 11%, 1%, and 1% at the high dose (200 mM) levels. Including the skin depot for MES, PT, and MT, respectively, there was 40%, 41%, and 21% (low dose), 26%, 16%, and 8% (medium dose), and 13%, 19%, and 10% (high does) absorption. Efficacy of skin soap washing conducted at the 30 min exposure time ranged from 31% to 86%, varying by chemical and dose level. Skin depot levels were highest for the relatively lipophilic PT. "Pseudo" skin permeability coefficient (K(p)) data declined with dose level, suggesting skin saturation had occurred. An in-depth comparison with literature data was conducted and risk assessment of first responder exposure was briefly considered.

Topics: Absorption; Breast; Chemical Warfare Agents; Hazardous Substances; Humans; In Vitro Techniques; Insecticides; Malathion; Parathion; Permeability; Risk Assessment; Safety; Salicylates; Skin; Temperature

AtPep1, a 23-aa peptide encoded by Arabidopsis PROPEP1, a member of a small, six-member gene family, activates expression of the defense gene PDF1.2 (encoding defensin) and its own precursor gene, PROPEP1, through the jasmonate/ethylene signaling pathway, mediated by a cell-surface receptor, PEPR1. Overexpression of two family members, PROPEP1 and PROPEP2, enhances resistance of Arabidopsis plants against the pathogen Pythium irregulare, and PROPEP2 and PROPEP3 are expressed at highly elevated levels in Arabidopsis in response to pathogen infections and to several pathogen-associated molecules (general elicitors). Here, we report that PDF1.2, PR-1 (pathogenesis protein), and PROPEP genes were differentially expressed in the leaves of intact plants sprayed with methyl jasmonate and methyl salicylate and in excised leaves supplied through cut petioles with peptides derived from the C terminus of each of the encoded proteins. The expression of PDF1.2 and PR-1 elicited by the peptides was blocked in mutant plants deficient in the jasmonate/ethylene and salicylate pathways, and in wild-type plants by treatment with diphenylene iodonium chloride, an inhibitor of hydrogen peroxide production. PROPEP1, PROPEP 2, and PROPEP3 genes appear to have roles in a feedback loop that amplifies defense signaling pathways initiated by pathogens.

Topics: Acetates; Arabidopsis; Arabidopsis Proteins; Cyclopentanes; Defensins; Gene Expression Regulation, Plant; Genes, Plant; Immunity, Innate; Models, Biological; Oxylipins; Plant Growth Regulators; Salicylates; Signal Transduction

Structural genomics efforts have produced structural information, either directly or by modeling, for thousands of proteins over the past few years. While many of these proteins have known functions, a large percentage of them have not been characterized at the functional level. The structural information has provided valuable functional insights on some of these proteins, through careful structural analyses, serendipity, and structure-guided functional screening. Some of the success stories based on structures solved at the Northeast Structural Genomics Consortium (NESG) are reported here. These include a novel methyl salicylate esterase with important role in plant innate immunity, a novel RNA methyltransferase (H. influenzae yggJ (HI0303)), a novel spermidine/spermine N-acetyltransferase (B. subtilis PaiA), a novel methyltransferase or AdoMet binding protein (A. fulgidus AF_0241), an ATP:cob(I)alamin adenosyltransferase (B. subtilis YvqK), a novel carboxysome pore (E. coli EutN), a proline racemase homolog with a disrupted active site (B. melitensis BME11586), an FMN-dependent enzyme (S. pneumoniae SP_1951), and a 12-stranded beta-barrel with a novel fold (V. parahaemolyticus VPA1032).

Topics: Bacterial Proteins; Computational Biology; Crystallography, X-Ray; Esterases; Genomics; Models, Molecular; Plant Proteins; Protein Conformation; Proteins; Salicylates

We present the first calculations of excited-state dynamics using ab initio molecular dynamics with a multireference perturbation theory description of the electronic structure. The new AIMS-CASPT2 method is applied to a paradigmatic excited-state intramolecular proton-transfer reaction in methyl salicylate, and the results are compared with previous ultrafast spectroscopic experiments. Agreement of AIMS-CASPT2 and experimental results is quantitative. The results demonstrate that the lack of an observed isotope effect in the reaction is due to multidimensionality of the reaction coordinate, which largely involves heavy-atom bond alternation instead of proton transfer. Using the dynamics results as a guide, we also characterize relevant minima on the ground and first singlet excited state using CASPT2 electronic structure theory. We further locate an S1/S0 minimal energy conical intersection, whose presence explains experimental observations of a sharp decrease in fluorescence quantum yield at excitation energies more than 1,300 cm-1 above the excited-state origin.

Topics: Models, Chemical; Protons; Quantum Theory; Salicylates; Spectrum Analysis

We report the free-jet rotational spectra of methylsalicylate, a molecule with a possible tautomeric and conformational equilibrium. In the ground electronic state, the molecule adopts a form stabilized by an intramolecular hydrogen bond between the phenolic hydrogen and the carbonylic oxygen, and this structure is characterized as the lowest-energy form by quantum chemical calculations. All rotational transitions are split because of the internal rotation of the methyl group, and the value of the barrier for this motion was determined to be V(3) = 5.38 kJ mol(-1).

Topics: Molecular Structure; Quantum Theory; Rotation; Salicylates; Spectrum Analysis; Thermodynamics

Carnivorous arthropods use volatile infochemicals emitted from prey-infested plants in their foraging behavior. Although several volatile components are common among plant species, the compositions differ among prey-plant complexes. Studies showed that the predatory mite Neoseiulus womersleyi is attracted only to previously experienced plant volatiles. In this study, we identified the attractant components in prey-induced plant volatiles of two prey-plant complexes. N. womersleyi reared on Tetranychus kanzawai-infested tea leaves showed significant preference for a mixture of three synthetic compounds [mimics of the T. kanzawai-induced tea leaves volatiles: (E)-beta-ocimene, (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), and (E,E)-alpha-farnesene] at a level comparable to that for T. kanzawai-induced tea plant volatiles. However, mixtures lacking any of these compounds did not attract the predatory mites. Likewise, N. womersleyi reared on T. urticae-infested kidney bean plants showed a significant preference for a mixture of four synthetic compounds [mimics of the T. urticae-induced kidney bean volatiles: DMNT, methyl salicylate (MeSA), beta-caryophyllene, and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene] at a level comparable to that for T. urticae-induced kidney bean volatiles. The absence of any of the four compounds resulted in no attraction. These results indicate that N. womersleyi can use at least four volatile components to identify prey-infested plants.

Topics: Alkenes; Animals; Camellia; Mites; Odorants; Phaseolus; Pheromones; Plant Leaves; Predatory Behavior; Salicylates; Sesquiterpenes

In the bacterial degradation of polycyclic aromatic hydrocarbons (PAHs), salicylate hydroxylases catalyze essential reactions at the junction between the so-called upper and lower catabolic pathways. Unlike the salicylate 1-hydroxylase from pseudomonads, which is a well-characterized flavoprotein, the enzyme found in sphingomonads appears to be a three-component Fe-S protein complex, which so far has not been characterized. Here, the salicylate 1-hydroxylase from Sphingomonas sp. strain CHY-1 was purified, and its biochemical and catalytic properties were characterized. The oxygenase component, designated PhnII, exhibited an alpha3beta3 heterohexameric structure and contained one Rieske-type [2Fe-2S] cluster and one mononuclear iron per alpha subunit. In the presence of purified reductase (PhnA4) and ferredoxin (PhnA3) components, PhnII catalyzed the hydroxylation of salicylate to catechol with a maximal specific activity of 0.89 U/mg and showed an apparent Km for salicylate of 1.1 +/- 0.2 microM. The hydroxylase exhibited similar activity levels with methylsalicylates and low activity with salicylate analogues bearing additional hydroxyl or electron-withdrawing substituents. PhnII converted anthranilate to 2-aminophenol and exhibited a relatively low affinity for this substrate (Km, 28 +/- 6 microM). 1-Hydroxy-2-naphthoate, which is an intermediate in phenanthrene degradation, was not hydroxylated by PhnII, but it induced a high rate of uncoupled oxidation of NADH. It also exerted strong competitive inhibition of salicylate hydroxylation, with a Ki of 0.68 microM. The properties of this three-component hydroxylase are compared with those of analogous bacterial hydroxylases and are discussed in light of our current knowledge of PAH degradation by sphingomonads.

Topics: Catalysis; Chromatography, Liquid; Edetic Acid; Electrophoresis, Polyacrylamide Gel; Enzyme Activation; Enzyme Stability; Ions; Kinetics; Mixed Function Oxygenases; Protons; Salicylates; Sphingomonas; Substrate Specificity; Temperature

Topics: Esterases; Nicotiana; Phloem; Plant Diseases; Plant Proteins; Salicylates; Salicylic Acid; Signal Transduction; Tobacco Mosaic Virus

In plants, the mobile signal for systemic acquired resistance (SAR), an organism-wide state of enhanced defense to subsequent infections, has been elusive. By stimulating immune responses in mosaic tobacco plants created by grafting different genetic backgrounds, we showed that the methyl salicylate (MeSA) esterase activity of salicylic acid-binding protein 2 (SABP2), which converts MeSA into salicylic acid (SA), is required for SAR signal perception in systemic tissue, the tissue that does not receive the primary (initial) infection. Moreover, in plants expressing mutant SABP2 with unregulated MeSA esterase activity in SAR signal-generating, primary infected leaves, SAR was compromised and the associated increase in MeSA levels was suppressed in primary infected leaves, their phloem exudates, and systemic leaves. SAR was also blocked when SA methyl transferase (which converts SA to MeSA) was silenced in primary infected leaves, and MeSA treatment of lower leaves induced SAR in upper untreated leaves. Therefore, we conclude that MeSA is a SAR signal in tobacco.

Topics: Esterases; Feedback, Physiological; Kinetics; Mixed Function Oxygenases; Mutation; Nicotiana; Phloem; Plant Diseases; Plant Leaves; Plant Proteins; Plants, Genetically Modified; Salicylates; Salicylic Acid; Signal Transduction; Tobacco Mosaic Virus; Virus Replication

Topics: Adult; Anti-Inflammatory Agents, Non-Steroidal; Constriction, Pathologic; Diclofenac; Ductus Arteriosus, Patent; Echocardiography; Female; Fetal Diseases; Fixatives; Humans; Pregnancy; Salicylates; Ultrasonography, Prenatal

One of the major factors limiting the use of non-steroidal anti-inflammatory drugs is gastrointestinal toxicity. Gaultherin, 2-[(6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy] benzoic acid methyl ester, a natural salicylate derivative extracted from Gaultheria yunnanensis, has been shown to have analgesic and anti-inflammatory effects and lack gastric ulcerogenic effect compared to aspirin in our primary study. The aim of this study was to investigate the mechanism of action of gaultherin, which may rely on its active metabolite, and the mechanism responsible for the non-ulcerogenic property. The results showed that gaultherin (200 mg/kg) significantly inhibited the abdominal contractions in the acetic acid-induced writhing test in mice. The anti-inflammatory effect of gaultherin was demonstrated in the croton oil-induced ear edema model in mice. The results showed that gaultherin and equimolar dose of aspirin produced comparable inhibitory effects. The study of the metabolism characters of gaultherin in mice and rats indicated that gaultherin could be metabolically converted to salicylate, which produced the pharmacological effects, and provided effective concentrations for an extended period. In vitro metabolism experiment showed that gaultherin was metabolized by beta-glycosidase produced by human intestinal bacteria and esterases in intestine, blood and liver successively to release salicylate finally. The study suggested gaultherin did not cause gastric ulcer for the reason that it released salicylate in intestine slowly, not in stomach and it left the cyclooxygenase-1 unaffected, which was the source of cytoprotective prostaglandins in gastric epithelium.

Topics: Abdominal Pain; Acetic Acid; Administration, Oral; Animals; Anti-Inflammatory Agents, Non-Steroidal; Aspirin; Chromatography, High Pressure Liquid; Croton Oil; Disaccharides; Disease Models, Animal; Ear Diseases; Esterases; Gastric Mucosa; Gaultheria; Glycoside Hydrolases; Humans; Immersion; Inflammation; Intestines; Male; Mice; Plant Leaves; Plant Stems; Rats; Rats, Wistar; Restraint, Physical; Salicylates; Stomach Ulcer; Stress, Psychological; Water

Methyl salicylate (MeSA) vapor increased resistance against chilling injury (CI) in freshly harvested pink tomatoes. The expression patterns of alternative oxidase (AOX) before and during the chilling period demonstrated that pre-treatment of tomato fruit with MeSA vapor increased the transcript levels of AOX. We used 4 EST tomato clones of AOX from the public database that belong to two distinctly related families, 1 and 2 defined in plants. Three clones were designated as LeAOX1a, 1b and 1c and the fourth clone as LeAOX2. Using RT-PCR, 1a and 1b genes were found to be expressed in leaf, root and fruit tissues, but 1c was expressed preferentially in roots. RNA transcript from LeAOX1a of AOX subfamily 1 was present in much greater abundance than 1b or 1c. The presence of longer AOX transcripts detected by RNA gel blot analysis in cold-stored tomato fruit was confirmed to be the un-spliced pre-mRNA transcripts of LeAOX1a and LeAOX1b genes. Intron splicing of LeAOX1c gene was also affected by cold storage when it was detected in roots. This alternative splicing event in AOX pre-mRNAs molecules occurred, preferentially at low temperature, regardless of mRNA abundance. Transcript levels of several key genes involved in RNA processing (splicing factors: 9G8-SR and SF2-SR, fibrillarin and DEAD box RNA helicase) were also affected by changes in storage temperature. The aberrant splicing event in AOX pre-mRNA and its possible association with the change in expression of genes involved in RNA processing in tomato fruit having chilling disorder was discussed.

Topics: Acetates; Alternative Splicing; Cyclopentanes; Freezing; Gene Expression Regulation, Plant; Mitochondrial Proteins; Oxidoreductases; Oxylipins; Plant Proteins; RNA, Messenger; Salicylates; Solanum lycopersicum

Jasmonic acid (JA) is a signalling compound with a key role in both stress and development in plants, and is reported to elicit the emission of volatile organic compounds (VOCs). Here we studied the dynamics of such emissions and the linkage with photosynthetic rates and stomatal conductance. We sprayed JA on leaves of the Mediterranean tree species Quercus ilex and measured the photosynthetic rates, stomatal conductances, and emissions and uptake of VOCs using proton transfer reaction mass spectrometry and gas chromatography after a dark-light transition. Jasmonic acid treatment delayed the induction of photosynthesis and stomatal conductance by approx. 20 min, and decreased them 24 h after spraying. Indications were found of both stomatal and nonstomatal limitations of photosynthesis. Monoterpene emissions were enhanced (20-30%) after JA spraying. Jasmonic acid also increased methyl salicylate (MeSa) emissions (more than twofold) 1 h after treatment, although after 24 h this effect had disappeared. Formaldehyde foliar uptake decreased significantly 24 h after JA treatment. Both biotic and abiotic stresses can thus affect plant VOC emissions through their strong impact on JA levels. Jasmonic acid-mediated increases in monoterpene and MeSa emissions might have a protective role when confronting biotic and abiotic stresses.

Topics: Carbon Dioxide; Cyclopentanes; Dehydration; Formaldehyde; Light; Monoterpenes; Oxylipins; Photosynthesis; Plant Leaves; Quercus; Salicylates; Temperature

Two distinct full-length cDNAs from rough lemon that encoded miraculin-like proteins were isolated by random amplification of cDNA ends (RACEs), based on sequence information from subtractive PCR previously described, and designated as RlemMLP1 and RlemMLP2. The transcripts of both RlemMLP1 and RlemMLP2 were not detected in leaves, or stems but accumulated in fruits. Transcripts accumulated to higher levels in leaves after wounding, inoculation with conidia of Alternaria alternata, or treatment with methyl jasmonate vapors. Treatment with methyl salicylate antagonized the signaling pathway of wounding. Treatment with methyl salicylate at 2 h after wounding significantly reduced wounding-induced gene expression of both RlemMLP1 and RlemMLP2. Protein products of these genes were obtained by using a prokaryotic expression system, and had protease inhibitor activity. RlemMLP2, but not RlemMLP1, contained a thaumatin motif, and only RlemMLP2 showed anti-fungal activity against Alternaria citri. Cellular localization analysis with RlemMLP1 or RlemMLP2 fused to a green fluorescence protein gene following transient translation using a particle bombardment in onion cells indicated that both RlemMLP1 and RlemMLP2 were localized to the cytosol. These evidences revealed that rough lemon RlemMLPs are likely to have defensive function against pathogens at least when host cells are broken by their infections.

Topics: Acetates; Amino Acid Sequence; Base Sequence; Citrus; Cloning, Molecular; Cyclopentanes; DNA, Complementary; DNA, Plant; Gene Expression Regulation, Plant; Molecular Sequence Data; Oxylipins; Plant Growth Regulators; Plant Proteins; RNA, Messenger; RNA, Plant; Salicylates

The theoretical 2H-distribution in the aromatic ring of phenylpropanoids can be predicted from that of their precursors--erythrose-4-phosphate, phosphoenolpyruvate and NADPH--and by invoking the mechanism of the NIH-shift and implied deuterium isotope effects. For each position in the non-oxygenated ring, the predicted natural 2H-abundance is in excellent agreement with experimental data obtained from quantitative 2H NMR-measurements on natural compounds, especially concerning the relative 2H-abundances p > o > or = m. For the p-hydroxylated derivatives, the experimentally determined 2H-abundance sequence order m > o can also be deduced, assuming an anisotropic migration (intramolecular isotope effect) of the p-hydrogen atom to the two differently 2H-substituted m-positions during the NIH-shift (intramolecular hydrogen transfer) and an in vivo deuterium kinetic isotope effect of approximately 1.20 on the final hydrogen elimination from the proposed ketodiene intermediate. The predicted 2H-distribution pattern of methyl salicylate 10, a representative of an o-hydroxylated natural compound, is in excellent agreement with that reported from 2H NMR analyses. However, for salicyl alcohol, minor differences between the theoretical and experimentally determined pattern are found that cannot yet be satisfactorily explained. On the other hand, a very good agreement is found between the theoretical and experimental pattern of coumarin, provided a deuterium kinetic isotope effect of approximately 1.30 is assumed for the elimination of the H-atoms from the ketodiene intermediate. The secondary m-hydroxylation of p-coumaric acid in the biosynthesis of vanillin seems to proceed without large isotope effects. Parallel differences are also observed for the 18O-kinetic isotope effects on the corresponding monooxygenase-catalysed reactions. The results demonstrate convincingly that the mechanisms of these general reactions of the phenylpropanoid biosynthetic pathway are identical and follow general principles. Small observed differences between the 2H-patterns of individual natural aromatic compounds originating from the same hydroxylation type can therefore be assigned to differences of the patterns of the precursors, the extent and the orientation of the hydrogen migration, and the kinetic isotope effect on the final hydrogen elimination. The evidence for the existence of general systematic rules governing isotopic patterns in the shikimic acid pathway and its subsequent

Topics: Benzaldehydes; Benzene Derivatives; Biological Factors; Carbon Isotopes; Cinnamates; Coumarins; Deuterium; Hydroxylation; Magnetic Resonance Spectroscopy; Models, Chemical; NADP; Phosphoenolpyruvate; Propanols; Salicylates; Shikimic Acid; Sugar Phosphates

Blends of volatile chemicals emanating from cassava leaves infested by the cassava green mite were found to promote conidiation of Neozygites tanajoae, an entomopathogenic fungus specific to this mite. Methyl salicylate (MeSA) is one compound frequently present in blends of herbivore-induced plant volatiles (HIPV) as well as that of mite-infested cassava. Here, we investigated the effect of methyl salicylate in its pure form on the production of pre-infective spores (conidia), and the germination of these spores into infective spores (capilliconidia), by a Brazilian isolate and a Beninese isolate of N. tanajoae. Mummified mites previously infected by the fungal isolates were screened under optimal abiotic conditions for sporulation inside tightly closed boxes with or without methyl salicylate diffusing from a capillary tube. Production of conidia was consistently higher (37%) when the Beninese isolate was exposed to MeSA than when not exposed to it (305.5 +/- 52.62 and 223.2 +/- 38.13 conidia per mummy with and without MeSA, respectively). MeSA, however, did not promote conidia production by the Brazilian isolate (387.4 +/- 44.74 and 415.8 +/- 57.95 conidia per mummy with and without MeSA, respectively). Germination of the conidia into capilliconidia was not affected by MeSA for either isolate (0.2%, 252.6 +/- 31.80 vs. 253.0 +/- 36.65 for the Beninese isolate and 4.2%, 268.5 +/- 37.90 vs. 280.2 +/- 29.43 for the Brazilian isolate). The effects of MeSA on the production of conidia were similar to those obtained under exposure to the complete blends of HIPV for the case of the Beninese isolate, but dissimilar (no promoting effect of MeSA) for the case of the Brazilian isolate. This shows that MeSA, being one compound out of many HIPV, can be a factor promoting sporulation of N. tanajoae, but it may not be the only factor as its effect varies with the fungal isolate under study.

Topics: Animals; Benin; Brazil; Entomophthorales; Manihot; Mites; Odorants; Salicylates; Spores, Fungal

Soybean [Glycine max (L.) Merr.] is a rich source of isoflavones that are often affected by biotic and abiotic factors. The objectives of this study were to evaluate the effect of various concentrations of three natural elicitors applied at different soybean growth stages on isoflavone content and to compare the efficiency of several solvent systems in isoflavone extraction and quantification. The isoflavones extracted from R96-3444 soybean using eight solvent systems were separated, identified, and quantified by a high-performance liquid chromatography (HPLC) procedure. The soybean plants were sprayed with salicylic acid, methyl salicylate, or ethyl acetate at 0, 10(-6), 10(-3), and 10(-1) M at R1 (blooming) or R4 (full pods) growth stage. Results showed that 10(-3) M ethyl acetate sprayed at the R1 stage significantly increased total isoflavone content and the levels of some individual isoflavones in soybean seeds. With all the elicitors that were tested, concentration was a more important factor than application time with respect to isoflavone content with lower concentrations being more effective on most isoflavones. A 53% acetonitrile solvent system was the best solvent system for extracting total isoflavone, malonyl glucosides, genistein, glycitin, genistin, acetyl-daidzin, and acetyl-genistin. The results of this study will be useful for increasing the isoflavone content in desirable soybean varieties and improving isoflavone concentration during extraction.

Topics: Acetates; Chromatography, High Pressure Liquid; Glycine max; Isoflavones; Salicylates; Salicylic Acid; Seeds

To investigate the root canal morphology of mandibular incisors in a Jordanian population using a canal staining and tooth-clearing technique.. Four hundred and fifty extracted mandibular incisors were collected from dental clinics within north Jordan. Following pulp tissue removal and staining of the canal systems, the teeth were decalcified with 5% nitric acid, dehydrated with ascending concentrations of alcohol and rendered clear by immersion in methyl salicylate. Cleared teeth were examined by eye and the following features were evaluated: (i) number and type of root canals; (ii) presence and location of lateral canals and intercanal communications; (iii) location of apical foramina; and (iv) frequency of apical deltas.. The majority of mandibular incisors had a single canal (73.8% of teeth possessed a Type I canal system). Although 26.2% of the roots possessed two canals, only 8.7% had two separate apical foramina.. The prevalence of two canals in this group of mandibular incisors was 26.2% and is within the range of previous studies performed on populations of different racial origin.

Topics: Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Ethanol; Fixatives; Histocytological Preparation Techniques; Humans; Incisor; Jordan; Mandible; Nitric Acid; Pulpectomy; Salicylates; Solvents; Tooth Apex

An increasing number of formulations are applied to equine skin, yet variable penetration can affect efficacy, or the incidence of adverse effects, or both. To investigate the effects of common methods of skin preparation on transdermal drug penetration in vitro, we clipped, harvested, and froze skin samples from 5 Thoroughbred geldings. Thawed samples were prepared as follows: control (no preparation); cleaned with aqueous chlorhexidine (Aq-C, 0.1% w/v); cleaned with alcoholic chlorhexidine (Al-C, 0.5% w/v); shaved (Sh); or tape-stripped (Ta) with the use of adhesive tape. The samples were then placed in diffusion cells, and 2 g of methylsalicylate (MeSa) gel (Dencorub) was applied to the stratum corneum side. The penetration of MeSa and its analyte, salicylate (Sa), through the skin samples was measured over 10 h. Compared with control skin, significantly more MeSa penetrated through skin prepared with Al-C or Sh (P < 0.01) or with Aq-C or Ta (P < 0.05), and significantly more Sa was recovered in the receptor phase from skin prepared with Aq-C, Al-C, or Sh (P < 0.05) or with Ta (P < 0.01). A significantly higher rate of penetration and shorter lag time were also noted for MeSa with all the prepared skin samples, compared with the control samples. The results show that clinical techniques routinely used to clean or prepare skin can significantly affect the rate and extent of penetration of a topically applied drug. This may result in greater systemic availability of active drug, which could lead to enhanced efficacy and, possibly, a higher incidence of adverse effects.

Topics: Administration, Cutaneous; Administration, Topical; Animals; Area Under Curve; Chlorhexidine; Ethanol; Hair; Horses; In Vitro Techniques; Male; Salicylates; Skin; Skin Absorption

A microfabricated planar differential ion mobility spectrometer operating from 0.4 to 1.55 atm in a supporting atmosphere of purified air was used to characterize the effects of pressure and electric field strength on compensation voltage, ion transmission, peak width, and peak intensity in differential mobility spectra. Peak positions, in compensation voltage as a function of separating rf voltage, were found to vary with pressure in a way that can be simplified by expressing both compensation and separation fields in Townsend units for E/N. The separation voltage providing the greatest compensation voltage and the greatest resolution is ion-specific but often occurs at E/N values that are unreachable at elevated pressure because of electrical breakdown. The pressure dependence of air breakdown voltage near 1 atm is sublinear, allowing higher E/N values to be reached at reduced pressure, usually resulting in greater instrumental resolution. Lower voltage requirements at reduced pressure also reduce device power consumption.

Topics: Air Pressure; Algorithms; Ions; Mass Spectrometry; Microchemistry; Organophosphonates; Organophosphorus Compounds; Protons; Salicylates; Sensitivity and Specificity

Topics: Administration, Topical; Adolescent; Adult; Anti-Infective Agents; Bacterial Infections; Drug Combinations; Female; Hexetidine; Humans; Male; Middle Aged; Oils, Volatile; Plant Oils; Salicylates; Tonsillectomy; Tonsillitis

Several forms of periodontal diseases (PD) are often associated with modified phagocytosing leukocytes and contemporary free radical production. Host antioxidant defenses could benefit from toothpastes used as adjuncts to counteract plaque-associated bacteria. The aim of the present study was to determine possible antioxidant activity (AA) of 12 differently antioxidant-enriched toothpastes, regardless of their efficacy as antimicrobial agents. Toothpastes were enriched alternatively with sodium ascorbyl phosphate, alpha-tocopherol acetate, pycnogenol, allantoin and methyl salycilate or a mixture of these. AA was tested in a cell-free system with a ABTS-decolorization assay improved by means of a flow injection analysis device. Comet assay, using NCTC 2544 keratinocytes, was performed to test if it was possible to identify any protection against in vitro DNA fragmentation provoked by a challenge with H(2)O(2) in cultures pre-incubated with toothpaste extracts. Only toothpastes containing sodium ascorbyl phosphate displayed clear AA with I(50) values ranging between 50 and 80 mg of toothpaste/ml water. COMET analysis of cells challenged with H(2)O(2) in presence of toothpaste extracts revealed a limited protection exerted by sodium ascorbyl phosphate. The results described herein indicate that toothpastes containing sodium ascorbyl phosphate possess AA. All the data were obtained in systems in vitro and the demonstration of in vivo AA is desirable. These findings could be useful in the treatment and maintenance of some forms of PD and should be considered when arranging new toothpaste formulations.

Topics: alpha-Tocopherol; Antioxidants; Apoptosis; Ascorbic Acid; Cells, Cultured; Comet Assay; DNA; Fixatives; Flavonoids; Humans; Hydrogen Peroxide; In Vitro Techniques; Keratinocytes; Oxidants; Plant Extracts; Platelet Aggregation Inhibitors; Salicylates; Tocopherols; Toothpastes

The use of two methods in tandem, single-sided membrane introduction mass spectrometry (SS-MIMS) and fiber introduction mass spectrometry (FIMS), is presented as a technique for field analysis. The combined SS-MIMS-FIMS technique was employed in both a modified commercial mass spectrometer and a miniature mass spectrometer for the selective preconcentration of the explosive simulant o-nitrotoluene (ONT) and the chemical warfare agent simulant, methyl salicylate (MeS), in air. A home-built FIMS inlet was fabricated to allow introduction of the solid-phase microextraction (SPME) fiber into the mass spectrometer chamber and subsequent desorption of the trapped compounds using resistive heating. The SS-MIMS preconcentration system was also home-built from commercial vacuum parts. Optimization experiments were done separately for each preconcentration system to achieve the best extraction conditions prior to use of the two techniques in combination. Improved limits of detection, in the low ppb range, were observed for the combination compared to FIMS alone, using several SS-MIMS preconcentration cycles. The SS-MIMS-FIMS response for both instruments was found to be linear over the range 50 to 800 ppb. Other parameters studied were absorption time profiles, effects of sample flow rate, desorption temperature, fiber background, memory effects, and membrane fatigue. This simple, sensitive, accurate, robust, selective, and rapid sample preconcentration and introduction technique shows promise for field analysis of low vapor pressure compounds, where analyte concentrations will be extremely low and the compounds are difficult to extract from a matrix like air.

Topics: Air Pollutants; Chemical Warfare Agents; Explosions; Mass Spectrometry; Miniaturization; Salicylates; Toluene; Volatilization

Securidaca longepedunculata Fers (Polygalaceae) is commonly used as a traditional medicine in many parts of Africa as well as against a number of invertebrate pests, including insects infesting stored grain. The present study showed that S. longepedunculata root powder, its methanol extract, and the main volatile component, methyl salicylate, exhibit repellent and toxic properties to Sitophilus zeamais adults. Adult S. zeamais that were given a choice between untreated maize and maize treated with root powder, extract, or synthetic methyl salicylate in a four-way choice olfactometer significantly preferred the control maize. Methyl salicylate vapor also had a dose-dependant fumigant effect against S. zeamais, Rhyzopertha dominica, and Prostephanus truncates, with a LD100 achieved with a 60microl dose in a 1-l container against all three insect species after 24 hr of exposure. Probit analyses estimated LD50 values between 34 and 36 microl (95% CI) for all insect species. Furthermore, prolonged exposure for 6 days showed that lower amounts (30 microl) of methyl salicylate vapor were able to induce 100% adult mortality of the three insect species. The implications are discussed in the context of improving stored product pest control by small-scale subsistence farmers in Africa.

Topics: Animals; Edible Grain; Food Preservation; Insecta; Insecticides; Medicine, African Traditional; Methanol; Oils, Volatile; Plant Extracts; Plant Roots; Salicylates; Securidaca; Time Factors; Zea mays

Methyl salicylate is a compound currently used in the creation of many flavors. It can be obtained by synthesis or from two natural sources: essential oil of wintergreen and essential oil of sweet birch bark. Deuterium site-specific natural isotope abundance (A(i)) determination by NMR spectroscopy with the method of reference ERETIC ((2)H-ERETIC-NMR) has been applied to this compound. A(i) measurements have been performed on 19 samples of methyl salicylate from different origins, natural/synthetic and commercial/extracted. This study demonstrates that appropriate treatment performed on the data allows discrimination between synthetic and natural samples. Moreover, the representation of intramolecular ratios R(6/5) as a function of R(3/2) distinguishes between synthetics, wintergreen oils, and sweet birch bark oils.

Topics: Betula; Deuterium; Magnetic Resonance Spectroscopy; Oils, Volatile; Plant Bark; Salicylates

To investigate penetration of a topically applied nonsteroidal anti-inflammatory drug (NSAID) into tissues and synovial fluid.. 5 Greyhounds.. Dogs were anesthetized and microdialysis probes placed in the dermis and gluteal muscle over each coxofemoral (hip) joint. Methylsalicylate (MeSA) was applied topically over the left hip joint. Dialysate and plasma (blood samples from the cephalic and femoral veins) were obtained during the subsequent 5 hours. Dogs were euthanatized, and tissue samples and synovial fluid were collected and analyzed for salicylic acid (SA) and MeSA by use of high-pressure liquid chromatography.. SA and MeSA concentrations increased rapidly (< 30 minutes after application) in dialysate obtained from treated dermis. Salicylic acid also appeared in plasma within 30 minutes and reached a plateau concentration after 2 hours, although combined drug concentrations (SA plus MeSA) in plasma obtained from femoral vein samples were twice those measured in plasma obtained from the cephalic vein (SA only). Treated muscle had a progressive decrease in NSAID concentration with increasing depth (SA and MeSA), but it was significantly higher than the concentration in untreated muscle. Substantial amounts of SA and MeSA were also measured in synovial fluid of treated joints.. Topically applied NSAIDs can penetrate deeply into tissues and synovial fluid. Local concentrations higher than circulating systemic concentrations are suggestive that direct diffusion and local blood redistribution are contributing to this effect. Systemic blood concentrations may be inadequate to describe regional kinetics of topically applied drugs.

Topics: Administration, Cutaneous; Animals; Anti-Inflammatory Agents, Non-Steroidal; Dogs; Male; Muscle, Skeletal; Salicylates; Salicylic Acid; Skin; Synovial Fluid

Many plants infested by herbivores or viruses can rapidly produce and accumulate a plant-signaling compound, methyl salicylate (MeSA), in their leaves to activate disease resistance. In the present work, a simple, rapid, and sensitive method was developed for the determination of MeSA in tomato leaves by direct sample introduction and thermal desorption followed by GC-MS. Results show that the proposed method has a low detection limit (0.08 ng mg(-1)) and good precision (RSD = 8.9%). The present method was applied to the investigation of tomato plant defense response to tobacco mosaic virus (TMV) by rapid analysis of volatile compounds in plant leaves. It was found that tomato plants can produce large amounts of MeSA as a defense response to TMV. This indicates that MeSA may be a plant-signaling compound in tomato plant defense response to TMV.

Topics: Gas Chromatography-Mass Spectrometry; Hot Temperature; Plant Leaves; Salicylates; Solanum lycopersicum; Time Factors; Tobacco Mosaic Virus

We investigated volatile infochemicals possibly involved in location of the generalist predatory mite Neoseiulus californicus to plants infested with spider mites in a Y-tube olfactometer. The predators significantly preferred volatiles from lima bean leaves infested with Tetranychus urticae to uninfested lima bean leaves. Likewise, they were attracted to volatiles from artificially damaged lima bean leaves and those from T. urticae plus their visible products. Significantly more predators chose infested lima bean leaves from which T. urticae plus their visible products had been removed than artificially damaged leaves, T. urticae, and their visible products. These results suggest that N. californicus is capable of exploiting a variety of volatile infochemicals originating from their prey, from the prey-foodplants themselves, and from the complex of the prey and the host plants (e.g., herbivore-induced volatiles). We also investigated predator response to some of the synthetic samples identified as volatile components emitted from T. urticae-infested lima bean leaves and/or artificially damaged lima bean leaves. The predators were attracted to each of the five synthetic volatile components: linalool, methyl salicylate, (Z)-3-hexen-1-ol, (E)-2-hexenal, and (Z)-3-hexenyl acetate. The role of each volatile compound in prey-searching behavior is discussed.

Topics: Acetates; Acyclic Monoterpenes; Aldehydes; Animals; Chemotactic Factors; Female; Hexanols; Mites; Monoterpenes; Odorants; Phaseolus; Plant Leaves; Predatory Behavior; Salicylates; Smell; Tetranychidae; Volatilization

Induced volatiles provide a signal to foraging predatory insects about the location of their prey. In Iowa, early in the growing season of soybean, Glycine max, many predacious seven-spotted lady beetles, Coccinella septempunctata, were observed on plants with heavy infestations of soybean aphid, Aphis glycines. We studied whether the attraction of this beetle is caused by the release of specific volatile compounds of soybean plants infested by aphids. Volatile compounds emitted by soybean plants infested by aphids were compared with those of undamaged, uninfested, and artificially damaged plants. Gas chromatography-mass spectrometry analyses revealed consistent differences in the profiles of volatile compounds between aphid-infested soybean plants and undamaged ones. Significantly more methyl salicylate was released from infested plants at both the V1 and V2 plant growth stages. However, release patterns of two other induced plant volatiles, (D)-limonene and (E,E)-alpha-farnesene, differed between the two plant growth stages. Gas chromatographic-electroantennographic detection of volatile extracts from infested soybean plants showed that methyl salicylate elicited significant electrophysiological responses in C. septempunctata. In field tests, traps baited with methyl salicylate were highly attractive to adult C. septempunctata, whereas 2-phenylethanol was most attractive to the lacewing Chrysoperla carnea and syrphid flies. Another common lady beetle, the multicolored Asian lady beetle, Harmonia axyridis, showed no preference for the compounds. These results indicate that C. septempunctata may use methyl salicylate as the olfactory cue for prey location. We also tested the attractiveness of some selected soybean volatiles to alate soybean aphids in the field, and results showed that traps baited with benzaldehyde caught significantly higher numbers of aphids.

Topics: Animals; Aphids; Coleoptera; Dose-Response Relationship, Drug; Glycine max; Pheromones; Predatory Behavior; Salicylates

Root canal morphology of deciduous mandibular first molar was studied using roentgenographic and decalcification and clearing methods. Two groups of 15 teeth were formed. In the roentgenographic group, roots of the teeth were separated from the crown at the level of CEJ. Cut roots of the teeth were radiographed from both mesiodistal and buccolingual directions using separate IOPA films. In the decalcification and clearing group, teeth were decalcified and made transparent. Dye was injected later. The roots of the teeth were examined under 10 times for number, curvature, types and additional features of root canals. Deciduous mandibular first molar showed variability in root canal morphology. Four to five root canals were recorded. Majority of the teeth had 1-1 type of root canal anatomy, but 1-2 type anatomy was also reported. Straight, curved and S-shaped canal curvatures were recorded. Horizontal anastomosis, lateral canals and buccolingually broad root canals were also recorded.

Topics: Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Ethanol; Fixatives; Histocytological Preparation Techniques; Humans; Mandible; Methylene Blue; Molar; Nitric Acid; Oxidants; Radiography; Salicylates; Sodium Hypochlorite; Solvents; Tooth, Deciduous

Aims of this work were to examine lateral canals in extracted teeth, to propose a new technique to produce artificial lateral canals, and to compare two obturation techniques. Cleared roots were examined to record measure and shape of lateral canals. Artificial lateral canals were prepared on human demineralized teeth before final clearing. Specimens were divided in two groups: canals of group 1 were filled with Schilder's technique, canals of group 2 were filled with vertical compaction with apical backfilling. Stereomicroscopic analysis of lateral canal filling revealed lower filling rates in apical canals compared to coronal ones and higher filling rates with "vertical compaction with apical backfilling" compared to Schilder's group. The tested procedure appears to be a reliable technique to obtain standardized lateral canals and to compare filling procedures.

Topics: Decalcification Technique; Dental Pulp Cavity; Epoxy Resins; Fixatives; Gutta-Percha; Humans; Models, Anatomic; Root Canal Filling Materials; Root Canal Obturation; Root Canal Preparation; Salicylates; Tooth Apex

Methyl salicylate (MeSA) in many plants is a important signaling compound, which plays an important role in a pathogen-induced defense response. In this paper, gas chromatography-mass spectrometry (GC-MS) with headspace solid-phase microextraction (HS-SPME) was developed for determination of MeSA and other volatile compounds in leaves of a tomato plant (Lycopersicon esculentum). Tomato leaves were ground under liquid nitrogen and sampled by HS-SPME, with a 100 microm polydimethylsiloxane fiber, and finally analyzed by GC-MS. Eighteen compounds in the leaves of tomato plant infested by tobacco mosaic virus (TMV) were separated and identified, among them MeSA, which was quantitatively analyzed by the standard addition method. MeSA concentrations higher than 2.0 microg g(-1) fresh weight accumulated in leaves of TMV-infested tomato plant as the defense response to TMV. A similar concentration of MeSA in the leaves of MeSA-treated tomato plant was also found. No MeSA in leaves of control tomato plant was detected. These findings suggest that MeSA might be a signaling compound in the tomato plant response to TMV. The present method for determination of MeSA required only simple sample preparation and no organic solvent, and provided an excellent relative standard deviation of less than 5.0% and a low detection limit of 10 ng g(-1) fresh weight for MeSA. These results show that GC-MS-HS-SPME is a simple, rapid and sensitive method for determination of MeSA and other plant-signaling compounds in plant tissues.

Topics: Gas Chromatography-Mass Spectrometry; Plant Leaves; Salicylates; Solanum lycopersicum; Volatilization

The loss of the plasticizers dibutylphthalate, butylphthalylbutyl glycolate, benzylbenzoate, methylsalicylate, and benzylsalicylate from four soft lining materials was measured. A 0.1% aqueous solution of triton X-100, reduced was used as immersion medium, since the solubility of plasticizer in this medium was close to that of saliva. The loss of plasticizer was monitored up to 30 d after mixing. For two of the materials, the average amount of leached dibutylphthalate within the first day exceeded the proposed tolerable daily intake (TDI) by about 11 and 32 times, respectively, for an average adult person. Similarly, for these two materials, the average daily amount within the first 30 d of leached dibutylphthalate was 2.2 and 6.6 times larger, respectively, than the TDI limit. The cumulative amount leached over 30 d for each of the four materials was 128-253 mg plasticizer g(-1). The results indicate the need for further biological evaluations of these products.

Topics: Adult; Benzoates; Dental Restoration, Temporary; Denture Liners; Denture, Complete; Humans; Linear Models; Materials Testing; Maximum Tolerated Dose; Octoxynol; Phthalic Acids; Plasticizers; Salicylates; Saliva, Artificial

In decerebrate cats, topical application of analgesic balm (AB) can attenuate the pressor response to electrically induced static contraction. We examined the possibility that this phenomenon also occurs in humans and determined whether such effects were limited to a local action on the contracting muscle (e.g., attenuations of the action of groups III and IV muscle afferents that cause the exercise pressor reflex) or whether they also may have affected active muscle blood flow and/or central command.. Blood pressure (mean arterial pressure (MAP)), heart rate (HR), brachial artery blood flow (BABF), and relative perceived exertion (RPE) were assessed at rest and during 90 s of static handgrip contraction before and 50 min after application of a commercially available AB (1% capsaicin, 12.5% methyl salicylate) to the skin of the forearm muscles.. AB attenuated the MAP response to contraction (19 +/- 3 vs 27 +/- 5 mm Hg) but had no effect on the HR response. Absolute BABF was enhanced at rest and during contraction, but absolute (118 +/- 47 vs 114 +/- 47 mL x min) and percent increases (83 +/- 31 vs 55 +/-19%) were not statistically different between conditions. AB appeared to slightly enhance RPE, but this was also the case in a control protocol where only the vehicle (petroleum jelly) was used and no change in the blood pressure response was seen.. AB attenuates contraction-induced increases in MAP that do not seem to be related to alterations in perfusion of active muscle or central command. Effects appear to be localized to the active skeletal muscle and likely involve reductions in sensitivity of groups III and IV muscle afferents to local chemical and/or mechanical stimulation.

Topics: Administration, Topical; Adult; Analgesics; Blood Pressure; California; Capsaicin; Female; Forearm; Heart Rate; Humans; Male; Middle Aged; Muscle Contraction; Muscle, Skeletal; Physical Exertion; Regional Blood Flow; Salicylates

This paper presents a multi-drug fatality in which methyl salicylate was ingested. It is presented to inform the toxicological community that a particularly expeditious method of detection for methyl salicylate exists. Previously published methods for the analysis of methyl salicylate include a gas chromatographic-mass spectrometric method and an alkaline/acidic extraction followed by high-performance liquid chromatographic (HPLC) analysis. This article describes a method for analyzing methyl salicylate using HPLC, in which a simple, rapid extraction procedure is used. Using a previously published HPLC method, methyl salicylate and salicylic acid were easily identified in biological specimens. Methyl salicylate and salicylic acid were detected using an extraction solution of acetonitrile coupled with internal standard and then analyzed by HPLC-diode-array detection. Because of its concentrated liquid form, methyl salicylate ingestion can cause rapid onset salicylate toxicity. As the potentially fatal methyl salicylate forms are readily available and easily found on drugstore shelves, the need to rapidly detect and quantitate salicylic acid concentrations that are due to methyl salicylate ingestion may arise. In the case presented, the peripheral blood concentration of salicylic acid from methyl salicylate ingestion was 320 mg/L, and the concentration in gastric contents was 820 mg. It alone was not the cause of death, however. The discovery of the ability to detect and quantitate methyl salicylate was due to its suspected ingestion.

Topics: Acetonitriles; California; Chromatography, High Pressure Liquid; Drug Combinations; Drugs, Chinese Herbal; Fatal Outcome; Female; Gastrointestinal Contents; Humans; Middle Aged; Salicylates; Salicylic Acid; Suicide; Vietnam

Many carnivorous arthropods use herbivore-induced plant volatiles to locate their prey. These plant volatiles are blends of up to hundreds of compounds. It is often unknown which compounds in such a complex volatile blend represent the signal to the foraging carnivore. We studied the role of methyl salicylate (MeSA) as part of the volatile blend in the foraging behavior of the predatory mite Phytoseiulus persimilis by using a Y-tube olfactometer. MeSA is one of the compounds released by lima bean, infested with Tetranychus urticae--a prey species of the predatory mite. MeSA attracted satiated predatory mites in a dose-dependent way with optimum attraction at a dose of 0.2 microg. Predatory mites did not discriminate between a prey-induced lima bean volatile blend (that contains MeSA) and a prey-induced volatile blend to which an extra amount of synthetic MeSA had been added. However, they preferred a MeSA-containing volatile blend (induced by T. urticae) to an otherwise similar but MeSA-free blend (induced by jasmonic acid). Adding synthetic MeSA to the MeSA-free blend significantly increased the mites' choice for this odor, suggesting an important role for MeSA. This study is a new step toward unraveling the role of herbivore-induced plant volatiles in the foraging behavior of predatory arthropods.

Topics: Animals; Exploratory Behavior; Fixatives; Mites; Plants; Predatory Behavior; Salicylates; Smell; Volatilization

Although the arterial supply of the human testis via the testicular artery is a well-studied subject, the pattern of approach that this vessel takes when reaching the gland is, on the other hand, not as well described. Based on the observation of angiological preparations of 196 adult human testes, the authors describe the presence of transmediastinal testicular vessels in one fourth of the cases. These were of two varieties, as regards the testicular mediastinum: centrifugal and centripetal. The centrifugal vessels were briefly mentioned in the nineteenth century scientific literature, undescribed in twentieth century anatomical studies and only recently referred to in color Doppler ultrasonographic studies; the centripetal vessels are previously undescribed. The authors propose the terms transmediastinal centrifugal and centripetal arteries to designate them.

Topics: Adult; Arteries; Barium Sulfate; Benzoates; Contrast Media; Desiccation; Fixatives; Fluorescence; Formaldehyde; Gelatin; Humans; Hydrogen Peroxide; Male; Medical Illustration; Oxidants; Salicylates; Testis

Factorial design (FD) was applied in order to develop an optimised method for the detection of chemical warfare (CW) agent simulant compounds on Porapak Q. Application of FD allowed study of the adsorption/desorption mechanism of analytes. Di(propylene glycol) monomethyl ether (DPM) and methyl salicylate (MS) were selected for study as both compounds are employed in agent simulation trials but are currently analysed by different methods. An analytical method for simultaneous determination of both compounds was developed using solvent desorption. The optimised method identified non-polar interactions as the primary adsorption/desorption mechanism. Steel tubes were shown to be more suited for sampling of simulants, due to lower variability in recovery compared to glass tubes. Atmospheric detection limits for both simulants were estimated to be 0.2 mg m(-3) allowing the trace analysis of these compounds by gas chromatography with flame ionisation detection (GC-FID).

Topics: Chemical Warfare Agents; Models, Theoretical; Propylene Glycols; Salicylates; Solvents

Topics: Aged; Allergens; Bandages; Dermatitis, Allergic Contact; Diagnosis, Differential; Female; Hip; Humans; Patch Tests; Salicylates

The sex attractant pheromone produced in mandibular glands of queens of the slave-making ant Polyergus breviceps has been identified as a blend of methyl 6-methylsalicylate and 3-ethyl-4-methylpentanol. In field trials, each compound alone was completely unattractive to males, whereas blends of the two compounds attracted hundreds of males within a couple of hours.

Topics: Animals; Ants; Behavior, Animal; Female; Gas Chromatography-Mass Spectrometry; Male; Pentanols; Salicylates; Sex Attractants; Time Factors

Flower-specific benzenoid carboxyl methyltransferases from Stephanotis floribunda and Nicotiana suaveolens were biochemically and structurally characterized. The floral scents of both these species contain higher levels of methyl benzoate and lower levels of methyl salicylate. The S. floribunda enzyme has a 12-fold lower K(m) value for salicylic acid (SA) than for benzoic acid (BA), and results of in silico modeling of the active site of the S. floribunda enzyme, based on the crystal structure of Clarkia breweri salicylic acid methyltransferase (SAMT), are consistent with this functional observation. The enzyme was therefore designated SAMT. The internal concentration of BA in S. floribunda flowers is three orders of magnitude higher than the SA concentration, providing a rationale for the observation that these flowers synthesize and emit more methyl benzoate than methyl salicylate. The N. suaveolens enzyme has similar K(m) values for BA and SA, and the in silico modeling results are again consistent with this in vitro observation. This enzyme was therefore designated BSMT. However, the internal concentration of BA in N. suaveolens petals was also three orders of magnitude higher than the concentration of SA. Both S. floribunda SAMT and N. suaveolens BSMT are able to methylate a range of other benzenoid-related compounds and, in the case of S. floribunda SAMT, also several cinnamic acid derivatives, an observation that is consistent with the larger active site cavity of each of these two enzymes compared to the SAMT from C. breweri, as shown by the models. Broad substrate specificity may indicate recent evolution or an adaptation to changing substrate availability.

Topics: Amino Acid Sequence; Asteraceae; Benzoates; Conserved Sequence; Flowers; Models, Molecular; Molecular Sequence Data; Nicotiana; Odorants; Protein Conformation; Protein Methyltransferases; Salicylates; Sequence Alignment; Sequence Homology, Amino Acid

The tomato (Lycopersicon esculentum) mutant def-1, which is deficient in induced jasmonic acid (JA) accumulation upon wounding or herbivory, was used to study the role of JA in the direct and indirect defense responses to phytophagous mites (Tetranychus urticae). In contrast to earlier reports, spider mites laid as many eggs and caused as much damage on def-1 as on wild-type plants, even though def-1 lacked induction of proteinase inhibitor activity. However, the hatching-rate of eggs on def-1 was significantly higher, suggesting that JA-dependent direct defenses enhanced egg mortality or increased the time needed for embryonic development. As to gene expression, def-1 had lower levels of JA-related transcripts but higher levels of salicylic acid (SA) related transcripts after 1 d of spider mite infestation. Furthermore, the indirect defense response was absent in def-1, since the five typical spider mite-induced tomato-volatiles (methyl salicylate [MeSA], 4,8,12-trimethyltrideca-1,3,7,11-tetraene [TMTT], linalool, trans-nerolidol, and trans-beta-ocimene) were not induced and the predatory mite Phytoseiulus persimilis did not discriminate between infested and uninfested def-1 tomatoes as it did with wild-type tomatoes. Similarly, the expression of the MeSA biosynthetic gene salicylic acid methyltransferase (SAMT) was induced by spider mites in wild type but not in def-1. Exogenous application of JA to def-1 induced the accumulation of SAMT and putative geranylgeranyl diphosphate synthase transcripts and restored MeSA- and TMTT-emission upon herbivory. JA is therefore necessary to induce the enzymatic conversion of SA into MeSA. We conclude that JA is essential for establishing the spider mite-induced indirect defense response in tomato.

Topics: Animals; Cyclopentanes; Enzymes; Female; Oviposition; Oxylipins; Protease Inhibitors; Salicylates; Solanum lycopersicum; Terpenes; Tetranychidae; Transcription, Genetic; Volatilization

Males of the green-veined butterfly Pieris napi synthesize and transfer the volatile methyl salicylate (MeS) to females at mating, a substance that is emitted by non-virgin females when courted by males, curtailing courtship and decreasing the likelihood of female re-mating. The volatile is released when females display the 'mate-refusal' posture with spread wings and elevated abdomen, when courted by conspecific males. Here, we assess how the amount of MeS released by courted females changes over time since mating, and whether it is influenced by the frequency with which females display the mate-refusal posture. We also assess whether males tailor the anti-aphrodisiac content of ejaculates with respect to the expected degree of sperm competition, by comparing how males allocate MeS proportionately to first and second ejaculates in relation to ejaculate mass. The results show that females housed for 5 days in individual cages where they were able to fly and oviposit normally, released similar amounts of MeS. However, females housed together for the same period of time, causing them to frequently display the mate-refusal posture, released significantly lower levels of MeS than the individually housed females. This indicates that female display of the mate-refusal posture depletes their anti-aphrodisiac stores, and suggests that females are unable to voluntarily control their release of the anti-aphrodisiac. A comparison of relative proportion of MeS transferred by males in their first and second ejaculates showed that proportionately more MeS was allocated to the first ejaculate, in accordance with the idea that these are tailored to delay female re-mating.

Topics: Analysis of Variance; Animals; Butterflies; Chromatography, Gas; Female; Male; Mass Spectrometry; Salicylates; Semen; Sexual Behavior, Animal; Time Factors

The Y-olfactometer bioassays showed that the volatiles from tea aphids and tea aphid-damaged tea shoots (PHC) strongly attracted Sphaerophoria menthastri and Chrysopa septempunctata. At the dosage of 10(-4) g x ml(-1), S. menthastri selected geraniol and methyl salicylate from PHC, n-octanol from intact tea shoots (ITS), nerol from tea flowers (P < 0.01), and (E)-2-hexen-1-ol, E-2-hexenal, 1,3,6-octatriene-3,7-dimethyl and linalool from PHC (P < 0.05), while C. septempunctata selected n-octanol and hexanal from ITS (P < 0.05). At the dosage of 10(-2) g x ml(-1), S. menthastri selected hexanal, nerol and benzaldehyde from PHC (P < 0.05), while C. septempunctata selected hexanal, benzaldehyde, geraniol and (E)-2-hexen-1-ol (P < 0.05). The experimental results showed that besides aldehydes and methyl salicylate, geraniol, n-octanol and (E)-2-hexen-1-ol were significantly attractive to the natural enemies. The selective responses of natural enemies were restricted by thresholds. Both dosages of hexanal significantly attracted C. septempunctata. Nerol might be an infochemicals seducing S. menthastri to orient to tea flowers.

Topics: 1-Octanol; Acyclic Monoterpenes; Animals; Behavior, Animal; Chemotactic Factors; Chemotaxis; Diptera; Dose-Response Relationship, Drug; Flowers; Insecta; Monoterpenes; Odorants; Plant Extracts; Plant Shoots; Salicylates; Tea; Terpenes; Volatilization

There is increasing evidence that volatiles emitted by herbivore-damaged plants can cause responses in downwind undamaged neighboring plants, such as the attraction of carnivorous enemies of herbivores. One of the open questions is whether this involves an active (production of volatiles) or passive (adsorption of volatiles) response of the uninfested downwind plant. This issue is addressed in the present study. Uninfested lima bean leaves that were exposed to volatiles from conspecific leaves infested with the spider mite Tetranychus urticae, emitted very similar blends of volatiles to those emitted from infested leaves themselves. Treating leaves with a protein-synthesis inhibitor prior to infesting them with spider mites completely suppressed the production of herbivore-induced volatiles in the infested leaves. Conversely, inhibitor treatment to uninfested leaves prior to exposure to volatiles from infested leaves did not affect the emission of volatiles from the exposed, uninfested leaves. This evidence supports the hypothesis that response of the exposed downwind plant is passive. T. urticae-infested leaves that had been previously exposed to volatiles from infested leaves emitted more herbivore-induced volatiles than T. urticae-infested leaves previously exposed to volatiles from uninfested leaves. The former leaves were also more attractive to the predatory mite, Phytoseiulus persimilis, than the latter. This shows that previous exposure of plants to volatiles from herbivore-infested neighbors results in a stronger response of plants in terms of predator attraction when herbivores damage the plant. This supports the hypothesis that the downwind uninfested plant is actively involved. Both adsorption and production of volatiles can mediate the attraction of carnivorous mites to plants that have been exposed to volatiles from infested neighbors.

Topics: Acyclic Monoterpenes; Adaptation, Physiological; Adsorption; Alkenes; Animals; Chemotactic Factors; Mites; Monoterpenes; Phaseolus; Pheromones; Plant Leaves; Protein Synthesis Inhibitors; Salicylates; Terpenes; Tetranychidae; Time Factors; Volatilization

Evidence for recruitment and retention of beneficial insects in grapes and hops using controlled-release dispensers of methyl salicylate (MeSA), a component of herbivore-induced volatile blends, is presented. In a replicated experiment conducted in a juice grape vineyard, sticky cards in blocks baited with MeSA captured significantly greater numbers of five species of predatory insects (Chrysopa nigricornis, Hemerobius sp., Deraeocoris brevis, Stethorus punctum picipes, Orius tristicolor) than unbaited blocks. Four insect families (Syrphidae, Braconidae, Empididae, Sarcophagidae) were also significantly more abundant in the MeSA-baited blocks, as indicated by sticky card captures. Canopy shake samples and sticky card monitoring conducted in a MeSA-baited, unsprayed hop yard indicated development and maintenance of a beneficial arthropod population that was nearly four times greater than that present in an unbaited reference yard. Four times as many S. punctum picipes and six times as many O. tristicolor were sampled in the MeSA yard. Similar contrasts in abundance of these predators and others were apparent when compared with levels recorded in the yard in previous years. The large population of predatory insects in the MeSA-baited hop yard was associated with a dramatic reduction in spider mite numbers, the major arthropod pest of hops, in late June, and subeconomic populations were maintained for the rest of the season. The evidence presented here is highly suggestive that the use of controlled-release MeSA in a crop could increase recruitment and residency of populations of certain beneficial insects. This strategy may have the potential to enhance the efficacy and reliability of conservation biological control in crop pest management.

Topics: Animals; Coleoptera; Crops, Agricultural; Ecology; Fruit; Insect Control; Population Dynamics; Salicylates; Seasons; Smell; Volatilization

We used field assays to study attraction of feral northern and western corn rootworm beetles (Diabrotica barberi and D. virgifera virgifera) to a series of mostly nitrogenous and benzenoid synthetic compounds allied with host plant and floral aromas. Vaporization rates were obtained for most field-tested compounds and selected additional lures under both ideal and field-representative, but constant, conditions. Although many test compounds showed at least trace activity for one or both species, methyl benzoate and some of its derivatives, notably methyl anthranilate and methyl 4-methoxybenzoate, merited emphasis as effective new lures for females. Structural alteration of methyl benzoate had consistently negative effects on northern corn rootworm captures despite variable effects on release rate, whereas western corn rootworm was more strongly attracted to methyl anthranilate and methyl 4-methoxybenzoate than to the considerably more volatile parent compound. Phenylacetaldoxime was attractive to females of both species, but no more so than syn-benzaldoxime, included as reference. Release rate was disproportionately low for benzaldoxime, as well as other nitrogenous lures, under field compared with ideal conditions. The attractiveness of salicylaldoxime to northern corn rootworm, despite its low field release rate, and the unattractiveness of methyl salicylate, having a methyl ester in place of the oxime group, similarly highlighted importance of the oxime moiety for reactivity of this species.

Topics: Animals; Benzoates; Coleoptera; Dose-Response Relationship, Drug; Female; Insect Control; ortho-Aminobenzoates; Oximes; Plant Extracts; Salicylates; Sex Factors; Volatilization

In the insect antennal lobe, odor discrimination depends on the ability of the brain to read neural activity patterns across arrays of uniquely identifiable olfactory glomeruli. Less is understood about the complex temporal dynamics and interglomerular interactions that underlie these spatial patterns. Using neural-ensemble recording, we show that the evoked firing patterns within and between groups of glomeruli are odor dependent and organized in both space and time. Simultaneous recordings from up to 15 units per ensemble were obtained from four zones of glomerular neuropil in response to four classes of odorants: pheromones, monoterpenoids, aromatics, and aliphatics. Each odor class evoked a different pattern of excitation and inhibition across recording zones. The excitatory response field for each class was spatially defined, but inhibitory activity was spread across the antennal lobe, reflecting a center-surround organization. Some chemically related odorants were not easily distinguished by their spatial patterns, but each odorant evoked transient synchronous firing across a uniquely different subset of ensemble units. Examination of 535 cell pairs revealed a strong relationship between their recording positions, temporal correlations, and similarity of odor response profiles. These findings provide the first definitive support for a nested architecture in the insect olfactory system that uses both spatial and temporal coordination of firing to encode chemosensory signals. The spatial extent of the representation is defined by a stereotyped focus of glomerular activity for each odorant class, whereas the transient temporal correlations embedded within the ensemble provide a second coding dimension that can facilitate discrimination between chemically similar volatiles.

Topics: Action Potentials; Aldehydes; Animals; Brain; Brain Mapping; Discrimination, Psychological; Male; Manduca; Monoterpenes; Odorants; Olfactory Pathways; Physical Stimulation; Salicylates; Sex Attractants

Carnivorous arthropods can use herbivore-induced plant volatiles to locate their herbivorous prey. In the field, carnivores are confronted with information from plants infested with herbivores that may differ in their suitability as prey. Discrimination by the predatory mite Phytoseiulus persimilis between volatiles from lima bean plants infested with the prey herbivore Tetranychus urticae, or plants infested with the nonprey caterpillar Spodoptera exigua, depends on spider mite density. In this article, we analyzed the chemical composition of the volatile blends from T. urticae-infested lima bean plants at different densities of spider mites, and from S. exigua-infested plants. Based on the behavioral preferences of P. persimilis and the volatile profiles, we selected compounds that potentially enable the mite to discriminate between T. urticae-induced and S. exigua-induced volatiles. Subsequently, we demonstrated in Y-tube olfactometer assays that the relatively large amounts of methyl salicylate and (3E, 7E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene emitted by T. urticae-infested bean plants compared to S. exigua-infested plants enable the predators to discriminate. Our data show that specific compounds from complex herbivore-induced volatile blends can play an important role in the selective foraging behavior of natural enemies of herbivorous arthropods.

Topics: Alkenes; Animals; Biological Assay; Fabaceae; Host-Parasite Interactions; Mites; Oils, Volatile; Predatory Behavior; Salicylates

Essential oils obtained from different populations of Viola etrusca from Italy have been analysed to verify the phenotypic discontinuity observed in a previous study. All of the essential oils contained methyl salicylate as a main constituent. However, multivariate analysis showed differences among some populations, in particular between northern and southern ones. Results suggest that this species could be undergoing a slow schizogenetic differentiation process due to its genetic isolation.

Topics: Cluster Analysis; Italy; Multivariate Analysis; Oils, Volatile; Phenotype; Salicylates; Viola

This study used a modified tooth-clearing technique to allow observation of accessory canals following filling with a warm gutta-percha technique and one of two endodontic cements.. Ten extracted human maxillary molars with three roots were selected and divided into two equal groups of five teeth. Each group had 15 canals. Root canal preparation was performed with a modified double flared technique; irrigation with 5% NaOCl and lubrication with RC-Prep were used. The canals were then filled with gutta-percha and cement utilizing a warm vertical condensation technique in the apical third followed by thermo-mechanical compaction in the middle and coronal thirds. Pulp Canal Sealer or AH-Plus were used in the experimental groups. The teeth were demineralized with a modified buffered acid solution, cleared in methylsalicylate and examined under a stereomicroscope. Accessory canals were evaluated in the apical, middle and coronal thirds of each root canal and categorized as narrow or wide, following observation on four surfaces. The depth of penetration of gutta-percha and cement into lateral canals was scored using a 5-point system.. Complete transparency of the roots was achieved. Accessory canals were detected in all specimens. In coronal ramifications, gutta-percha filled the empty spaces (coronal thirds, grades 3 and 4: 70.9% in AH-Plus group and 68.8% in Pulp Canal Sealer group). In the apical accessory canals, gutta-percha entered less frequently (apical thirds, grades 3 and 4: 17.9% in the AH-Plus group and 3.2% in the Pulp Canal Sealer group); cement without gutta-percha (grades 1 and 2) was present in 55.5% in the AH-Plus group and 38.7% of the Pulp Canal Sealer group. Analysis showed that AH-Plus cement resulted in significantly greater filling of the apical accessory canals compared to Pulp Canal Sealer.. The modified tooth-clearing technique allowed observation of fine morphological details in all specimens. Effective gutta-percha filling was evident in most of the wide coronal lateral canals whilst the apical narrow ramifications were often incompletely filled by cement. Overall AH-Plus demonstrated better diffusion into lateral accessory canals compared to Pulp Canal Sealer.

Topics: Citrates; Decalcification Technique; Dental Pulp Cavity; Epoxy Resins; Fixatives; Formates; Gutta-Percha; Humans; Hydrochloric Acid; Molar; Quality of Health Care; Root Canal Filling Materials; Root Canal Obturation; Root Canal Preparation; Salicylates; Sodium Citrate; Zinc Oxide-Eugenol Cement

Pathogen-induced plant responses include changes in both volatile and non-volatile secondary metabolites. To characterize the role of bacterial pathogenesis in plant volatile emissions, tobacco plants, Nicotiana tabacum L. K326, were inoculated with virulent, avirulent, and mutant strains of Pseudomonas syringae. Volatile compounds released by pathogen-inoculated tobacco plants were collected, identified, and quantified. Tobacco plants infected with the avirulent strains P. syringae pv. maculicola ES4326 (Psm ES4326) or pv. tomato DC3000 (Pst DC3000), emitted quantitatively different, but qualitatively similar volatile blends of (E)-beta-ocimene, linalool, methyl salicylate (MeSA), indole, caryophyllene, beta-elemene, alpha-farnesene, and two unidentified sesquiterpenes. Plants treated with the hrcC mutant of Pst DC3000 (hrcC, deficient in the type-III secretion system) released low levels of many of the same volatile compounds as in Psm ES4326- or Pst DC3000-infected plants, with the exception of MeSA, which occurred only in trace amounts. Interaction of the virulent pathogen P. syringae pv. tabaci (Pstb), with tobacco plants resulted in a different volatile blend, consisting of MeSA and two unidentified sesquiterpenes. Overall, maximum volatile emissions occurred within 36 h post-inoculation in all the treatments except for the Pstb infection that produced peak volatile emissions about 60 h post-inoculation. (E)-beta-Ocimene was released in a diurnal pattern with the greatest emissions during the day and reduced emissions at night. Both avirulent strains, Psm ES4326 and Pst DC3000, induced accumulation of free salicylic acid (SA) within 6 h after inoculation and conjugated SA within 60 h and 36 h respectively. In contrast, SA inductions by the virulent strain Pstb occurred much later and conjugated SA increased slowly for a longer period of time, while the hrcC mutant strain did not trigger free and conjugated SA accumulations in amounts significantly different from control plants. Jasmonic acid, known to induce plant volatile emissions, was not produced in significantly higher levels in inoculated plants compared to the control plants in any treatments, indicating that induced volatile emissions from tobacco plants in response to P. syringae are not linked to changes in jasmonic acid.

Topics: Cyclopentanes; Immunity, Innate; Monoterpenes; Nicotiana; Oxylipins; Plant Diseases; Pseudomonas syringae; Salicylates; Salicylic Acid; Sesquiterpenes; Volatilization

Methyl salicylate (MeSA) and a number of other volatiles are primarily emitted in the evening/night by Stephanotis floribunda leading to attraction of night active pollinators. A second minor emission peak for MeSA occurs in the morning/day. To understand these emission patterns, we have studied in detail the temporal regulation of the last step of the biosynthetic pathway of MeSA, the convertion of salicylic acid (SA) to MeSA catalysed by S-adenosyl-L-methionine: salicylic acid carboxyl methyltransferase (SAMT). We observed that in young flowers a maximum in SAMT activity occurs in the night, and that in flowers which were open longer than 4 days, two SAMT activity maxima occurred per day. These maxima correlated well with dawn and dusk and the previously detected MeSA emission peaks. The SAMT mRNA levels, however, have a broad maximum during the dark phase, while the SAMT protein levels continuously increase during floral development without showing daily rhythms. Furthermore, under continuous illumination (LL) the SAMT mRNA levels and activity patterns oscillate, suggesting the involvement of a circadian clock in the regulation network. Taken together, this analysis clearly demonstrates that regulation of MeSA emission occurs both at the transcriptional and post-translational levels, indicating that control at more than one level is necessary to guarantee the precise timing of volatile emission in flowers of S. floribunda.

Topics: Apocynaceae; Circadian Rhythm; Flowers; Gene Expression Regulation, Developmental; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Light; Methyltransferases; Plant Proteins; Protein Processing, Post-Translational; RNA, Messenger; Salicylates; Salicylic Acid; Temperature; Transcription, Genetic

The toxicity of Eugenia caryophyllata bud and leaf oil-derived compounds (acetyleugenol, beta-caryophyllene, eugenol, alpha-humulene, and methyl salicylate) and congeners of eugenol (isoeugenol and methyleugenol) against eggs and females of Pediculus capitis was examined using direct contact application and fumigation methods and compared with those of the widely used delta-phenothrin and pyrethrum. In a filter paper diffusion bioassay with female P. capitis, the pediculicidal activity of the Eugenia bud and leaf oils was comparable to those of delta-phenothrin and pyrethrum on the basis of LT(50) values at 0.25 mg/cm(2). At 0.25 mg/cm(2), the compound most toxic to female P. capitis was eugenol followed by methyl salicylate. Acetyleugenol, beta-caryophyllene, alpha-humulene, isoeugenol, and methyleugenol were not effective. Eugenol at 0.25 mg/cm(2) was as potent as delta-phenothrin and pyrethrum but was slightly less effective than the pyrethroids at 0.125 mg/cm(2). Against P. capitis eggs, methyl salicylate and eugenol were highly effective at 0.25 and 1.0 mg/cm(2), respectively, whereas little or no activity at 5 mg/cm(2) was observed with the other test compounds as well as with delta-phenothrin and pyrethrum. In fumigation tests with female P. capitis at 0.25 mg/cm(2), eugenol and methyl salicylate were more effective in closed cups than in open ones, indicating that the effect of the compounds was largely due to action in the vapor phase. Neither delta-phenothrin nor pyrethrum exhibited fumigant toxicity. The Eugenia bud and leaf essential oils, particularly eugenol and methyl salicylate, merit further study as potential P. capitis control agents or lead compounds.

Topics: Animals; Eugenol; Female; Insecticides; Pediculus; Plant Leaves; Plant Oils; Plant Structures; Salicylates; Syzygium

Male Pieris napi butterflies previously have been shown to synthesize and transfer an antiaphrodisiac, methyl salicylate (MeS), to females at mating. This substance curtails courtship and decreases the likelihood of female remating. Here, we show that similar systems occur in Pieris rapae and Pieris brassicae. In P. rapae, 13C-labeling studies showed that males utilize the amino acids phenylalanine and tryptophan as precursors to MeS and indole, respectively. These volatiles are transferred to females at mating and function as antiaphrodisiacs, as demonstrated by field tests entailing painting MeS, indole, or a mixture on the abdomens of virgin females and assessing their attractiveness to wild males. With P. brassicae, 13C-labeling studies showed that males use phenylalanine as a precursor to synthesize benzyl cyanide, which was demonstrated to function as an antiaphrodisiac by field tests similar to those for P. rapae. This communication system exhibits both similarities and differences among the three species; in P. napi and P. rapae, males are fragrant but transfer a volatile antiaphrodisiac to females that is completely different from the male odor, whereas in P. brassicae the antiaphrodisiac transferred by male to female is identical with male odor.

Topics: Animals; Butterflies; Carbon Isotopes; Courtship; Male; Odorants; Salicylates; Sex Attractants; Volatilization

Synthetic methyl salicylate (MeSA), a herbivore-induced plant volatile (HIPV), was demonstrated to be an attractant for the green lacewing, Chrysopa nigricornis, in two field experiments conducted in a Washington hop yard. Significantly greater numbers of C. nigricornis were trapped on MeSA-baited sticky cards (mean: 2.8 +/- 0.4/card/week) than on unbaited cards (0.45 +/- 0.15) during June-September. Cards baited with two other HIPVs, hexenyl acetate and dimethyl nonatriene, did not attract more C. nigricornis than did unbaited traps (0.30 +/- 0.10, 0.44 +/- 0.15, respectively). MeSA-baited Unitraps captured 1.9 +/- 0.5 C. nigricornis/trap/week during July-August compared to 0.20 +/- 0.20/trap/week in methyl eugenol-baited traps and 0.03 +/- 0.03/trap/week in unbaited traps. The potential use of MeSA in enhancing C. nigricornis populations in Washington hop yards as an aid to conservation biological control of aphids and mites is discussed.

Topics: Agriculture; Animals; Aphids; Humulus; Insect Control; Insecta; Mites; Movement; Pheromones; Population Dynamics; Salicylates

Topics: Aged; Analgesics; Humans; Male; Medicine, Chinese Traditional; Oils; Poisoning; Salicylates

Emission of methylsalicylate (MeSA), and occasionally of methylbenzoate (MeBA), from Arabidopsis thaliana leaves was detected following the application of some forms of both biotic and abiotic stresses to the plant. Maximal emission of MeSA was observed following alamethicin treatment of leaves. A gene (AtBSMT1) encoding a protein with both benzoic acid (BA) and salicylic acid (SA) carboxyl methyltransferase activities was identified using a biochemical genomics approach. Its ortholog (AlBSMT1) in A. lyrata, a close relative of A. thaliana, was also isolated. The AtBSMT1 protein utilizes SA more efficiently than BA, whereas AlBSMT1 catalyzes the methylation of SA less effectively than that of BA. The AtBSMT1 and AlBSMT1 genes showed expression in leaves under normal growth conditions and were more highly expressed in the flowers. In A. thaliana leaves, the expression of AtBSMT1 was induced by alamethicin, Plutella xylostella herbivory, uprooting, physical wounding, and methyl jasmonate. SA was not an effective inducer. Using a beta-glucuronidase (GUS) reporter approach, the promoter activity of AtBSMT1 was localized to the sepals of flowers, and also to leaf trichomes and hydathodes. Upon thrip damage to leaves, AtBSMT1 promoter activity was induced specifically around the lesions.

Topics: Amino Acid Sequence; Arabidopsis; Arabidopsis Proteins; Base Sequence; Conserved Sequence; DNA Primers; Genome, Plant; Kinetics; Methylation; Methyltransferases; Molecular Sequence Data; Phylogeny; Reverse Transcriptase Polymerase Chain Reaction; Salicylates; Sequence Alignment; Sequence Homology, Amino Acid

To establish an in situ perfused pig ear model for percutaneous absorption.. The in situ perfused pig ear model for percutaneous absorption consisted of artificial gas, sample chamber, constant flow pump, constant temperature system, polytetrafluorethylene connective tube, porcine ear vein, porcine ear skin and special laminar flow apparatus. The perfused system viability was assessed by glucose utilization and lactate production. Ketoprofen isopropyl ester and methyl salicylate was used for validating this model. The concentrations of perfused sample were measured by HPLC.. Glucose utilization and lactate production showed that this model was viable till 7 h. Ketoprofen isopropyl ester was completely metabolized to ketoprofen in situ in perfused pig ear model. The steady cumulative amount (Q) of ketoprofen from permeation and metabolism was linear with time (t), the equation of ketoprofen formation was Q = -0.024 + 0.120t, the rate of ketoprofen formation was 0.120 microgram.cm-2.h-1. Methyl salicylate was partially metabolized to salicylic acid. The steady cumulative amount (Q) of methyl salicylate from permeation was linear with time (t), the permeation equation of methyl salicylate was Q = -3.809 + 6.129t, the permeation rate of metyl salicylate was 6.129 micrograms.cm-2.h-1. The steady cumulative amount (Q) of salicylic acid from metabolism was also linear with time (t), the formation equation of salicylic acid was Q = -1.785 + 0.879t, the formation rate of salicylic acid was 0.879 microgram.cm-2.h-1.. The in situ pig ear vein perfused model is a novel easy-handing and cost-efficient technique for percutaneous absorption and skin metabolism.

Topics: Administration, Cutaneous; Animals; Anti-Inflammatory Agents, Non-Steroidal; Ear, External; Ketoprofen; Male; Models, Animal; Perfusion; Salicylates; Salicylic Acid; Skin; Skin Absorption; Swine; Veins

Securidaca longepedunculata Fers (Polygalaceae) is commonly used as a medicine in many parts of Africa and shows promise for protecting stored grain against insect pests. Analysis of a methanol extract of the root bark by gas chromatography linked to mass spectrometry (GC/MS) showed a major component accounting for over 90% of the volatile material. This was identified as methyl 2-hydroxybenzoate (methyl salicylate) by comparison of the GC retention times and mass spectrum with those of synthetic standards. This conflicts with an earlier report that the major component is methyl 4-hydroxybenzoate. Two minor components had mass spectra characteristic of 2-hydroxybenzoate esters and were identified as methyl 2-hydroxy-6-methoxybenzoate and its benzyl analogue, again conflicting with an earlier report.

Topics: Benzoates; Gas Chromatography-Mass Spectrometry; Medicine, African Traditional; Methanol; Plant Extracts; Plant Roots; Plants, Medicinal; Polygalaceae; Salicylates; Solvents; Volatilization

We present an interesting case of salicylism arising from the use of methyl salicylate as part of a herbal skin cream for the treatment of psoriasis. A 40-year-old man became quite suddenly and acutely unwell after receiving treatment from an unregistered naturopath. Methyl salicylate (Oil of Wintergreen) is widely available in many over the counter topical analgesic preparations and Chinese medicated oils. Transcutaneous absorption of the methyl salicylate was enhanced in this case due to the abnormal areas of skin and use of an occlusive dressing. The presence of tinnitus, vomiting, tachypnoea and typical acid/base disturbance allowed a diagnosis of salicylate toxicity to be made. Our patient had decontaminated his skin prior to presentation, limiting the extent of toxicity and was successfully treated with rehydration and establishment of good urine flow.

Topics: Adult; Herbal Medicine; Humans; Male; Psoriasis; Salicylates; Skin Absorption

Pressor responses are reflexly evoked by the activation of groups III and IV muscle afferents, which are also known to mediate nociceptive responses. In this experiment, the effects of analgesic balm (AB) application on these responses were investigated without the interference of other types of anesthesia or effects from the higher brain.. Heart rate (HR), blood pressure, and end-tidal CO(2) were monitored in midcollicularly decerebrated cats. Static contractions (30 s) of hindlimb muscles were evoked by electric stimulation of L7 and S1 ventral roots. After control runs, a commercial AB (1% capsaicin, 12.5% methyl salicylate) was applied to the skin surface over the contracting muscles. Muscle contractions were evoked every 10 min, alternating between the two hindlimbs.. Changes in mean arterial pressure (MAP) evoked by static ipsilateral muscular contraction were significantly attenuated 20 min and 40 min after AB application. The decreases in the pressor response were significant at both the initial and the last parts of the stimulus intervention after 20 min of AB application. There were no significant changes in the response to contraction of the hindlimb contralateral to the AB application. Application of AB to the contralateral leg did not add to the ipsilateral effects.. AB application to the skin surface over contracting muscles significantly decreased autonomic responses to static muscular contraction. This effect was independent of higher cortical processing and strongly suggests that application of methyl salicylate and capsaicin on the skin has analgesic effects on signals from receptors located in muscle.

Topics: Administration, Topical; Analysis of Variance; Animals; Capsaicin; Cats; Electric Stimulation; Muscle Contraction; Muscles; Neurons, Afferent; Pressoreceptors; Salicylates

Membrane introduction mass spectrometry (MIMS) coupled to a miniature mass spectrometer equipped with a cylindrical ion trap (CIT) analyzer was used to monitor the flavor components, 3-phenyl-2-propenal and methyl salicylate, found in cinnamon and wintergreen candies, respectively, directly from human breath. The poly(dimethylsiloxane) (PDMS) membrane was operated in a trap-and-release mode, where the temperature of the membrane was cycled during the experiments, which permitted temporal resolution of the two compounds of interest, facilitating their observation in the complex sample. Under these thermally driven conditions, the 10-90% rise times for both compounds are similar (15 s for methyl salicylate, 17 s for 3-phenyl-2-propenal), but the difference in diffusivity means that the signal for 3-phenyl-2-propenal is delayed and the 10% point occurs 6 s later than that for wintergreen. Additional specificity needed for complex samples was gained by using tandem mass spectrometry.

Topics: Acrolein; Breath Tests; Humans; Ions; Mass Spectrometry; Membranes, Artificial; Organic Chemicals; Respiration; Salicylates; Sensitivity and Specificity; Volatilization

Despite enormous progress in the development of new morphological techniques, there is still not a simple technique for visualization of the fiber architecture in the mammalian brain. To develop such a technique, thick (400-600 microm) sections of the rat, mice, calf or postmortal human brain were fixed in paraformaldehyde, dehydrated in a series of ethanol and finally immersed in methyl salicylate. The major principle of this newly developed method was to make the neural tissue transparent, and then utilize the ability of neuronal fibers to deflect and deviate light directed from the side to render them visible. Dark-field illumination was used to create illuminating rays of light arriving at an angle exceeding the collecting angle of the objective lens, thus causing only the axonal pathways to be visible as a bright silver silhouette against a dark background. As a result, a three-dimensional structure of the whole white matter of the brain slice became clearly viewable. This technique worked equally well for mammalian brain frontal, sagittal and horizontal sections, as well as for the spinal cord sections. The method was appropriate for verification of axonal fiber courses in brain slice preparations used in electrophysiological experiments, including special applications, such as visualization of axonal bundles within neural transplants. Due to its simplicity, the technique can be successfully used even in an amateur laboratory having basic microscopy equipment and reagents.

Topics: Animals; Axons; Brain; Fixatives; Male; Mice; Mice, Inbred C3H; Nerve Fibers; Neural Pathways; Rats; Rats, Wistar; Salicylates

A tobacco peroxidase gene tpoxN1 was reported to be expressed within 1 h after wounding in leaves [Hiraga et al. (2000a) Plant Cell Physiol. 41: 165]. We describe here further results on the wound-induced tpoxN1 expression. The quick tpoxN1 induction occurred preferentially in stems and petioles, but was negligible in leaf blades even 8 h after wounding. Induced GUS activity was also detected rapidly after wounding in the stem of transgenic tobacco plants carrying the tpoxN1 promoter::GUS fusion gene, localized mainly in the vascular systems where it was maintained this level for 14 d or more. Strong GUS activity was also found in the petiole and veinlet as well as the epidermal tissue in the stem. Treatment of known inducers for wound-responsive genes such as jasmonate, 1-aminocyclopropane-1-carboxylate, spermine, phytohormones and other stress treatments did not enhance wound-induced tpoxN1 gene expression in stems at all, but rather repressed it in some cases. Studies using metabolic inhibitors suggested that phosphorylation and dephosphorylation of proteins together with de novo protein synthesis are likely to be involved in the wound-induced tpoxN1 expression as well as some other wound-responsive genes. Thus, tpoxN1 is a unique wound-inducible and possible wound-healing gene which is rapidly expressed being maintained for a long time in veins via an unknown wound-signaling pathway(s).

Topics: Acetates; Amino Acids, Cyclic; Brassinosteroids; Cholestanols; Cyclopentanes; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Histocytochemistry; Naphthaleneacetic Acids; Nicotiana; Oxylipins; Peroxidase; Phosphorylation; Plant Epidermis; Plant Growth Regulators; Plant Stems; Plants, Genetically Modified; RNA, Plant; Salicylates; Signal Transduction; Spermine; Steroids, Heterocyclic; Stress, Mechanical

To investigate the root and canal morphology of 351 mandibular permanent molars collected from an indigenous Thai population.. The cleaned teeth were accessed, the pulp dissolved by sodium hypochlorite under ultrasonication and the pulp system injected with Indian ink. The teeth were rendered clear by demineralization and immersion in methyl salicylate. The following observations were made: (i) number of roots and their morphology; (ii) number of root canals per tooth; (iii) number of root canals per root; (iv) root canal configuration in each root using Vertucci's classification, with additional modifications; and (v) presence and location of lateral canals and intercanal communications.. Of 118 mandibular first molars, 13% had a third disto-lingual root. In three-rooted teeth, 80% of the main distal roots and 100% of the disto-lingual roots had type 1 canal systems. Of 60 mandibular second molars, 10% had C-shaped roots, the majority of which had type 1 (33%) or type IV (33%) canal systems. Of 173 third molars, 68% had two separate roots, 20% had fused roots and 11% had a single C-shaped root; the majority had two canals (61%).. This study suggests that Thai molars exhibit features of both Caucasian and Chinese teeth.

Topics: Asian People; Carbon; Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Ethnicity; Fixatives; Humans; Mandible; Molar; Salicylates; Sodium Hypochlorite; Solvents; Thailand; Tooth Root; White People

Treatment of tomato (Lycopersicon esculentum L. cv. Beefstake) fruit with low concentrations of (0.01 mM) methyl jasmonate (MeJA) or methyl salicylate (MeSA) substantially enhanced their resistance to chilling temperature and decreased the incidence of decay during low-temperature storage. While studying the expression of pathogenesis-related (PR) protein genes, different accumulation patterns of PR-protein mRNAs in tomato fruit were observed. MeJA substantially increased the accumulation of PR-2b transcripts encoding intracellular beta-1,3-glucanase and enhanced the mRNA levels of PR-2a and PR-3b encoding extracellular beta-1,3-glucanase and intracellular chitinase, respectively. MeSA substantially increased accumulation of PR-2b and PR-3a mRNAs and slightly increased PR-3b mRNA accumulation. Chilling temperature did not appreciably enhance the accumulation of PR-protein mRNAs in untreated fruit. However, the accumulation of PR-3b mRNAs in MeSA-treated fruit was enhanced following low-temperature storage. Transcript abundance of catalase genes also was investigated in different pretreated tomatoes. The accumulation of cat1 mRNA was increased substantially by MeJA, while it was reduced by MeSA treatment. These results suggest that the pre-treatment of tomato fruit with MeSA or MeJA induces the synthesis of some stress proteins, such as PR proteins, which leads to increased chilling tolerance and resistance to pathogens, thereby decreasing the incidence of decay.

Topics: Acetates; beta-Glucosidase; Catalase; Chitinases; Cyclopentanes; Dose-Response Relationship, Drug; Freezing; Gene Expression Regulation, Plant; Glucan 1,3-beta-Glucosidase; Immunity, Innate; Oxylipins; Plant Proteins; RNA, Messenger; Salicylates; Solanum lycopersicum

The means by which olfactory systems enable the consistent recognition of biologically meaningful odors that may vary in composition over time is a central problem in olfaction. Experiments in honeybees have suggested a solution to one aspect of this problem by demonstrating that the learning of components in an odor mixture suppresses subsequent learning about additional components that are later added to that mixture. We here show, in rats, that intramodal olfactory blocking is also exhibited in vertebrates, and furthermore that the specific characteristics of this blocking are similar to those observed in intermodal blocking studies. Using an olfactory digging task, we submitted two groups of rats to the following olfactory training protocol: one group was first trained (five trials) on an odor (A), followed by five training trials on a binary mixture (A+B), while the second group was similarly trained on a different odor (C) followed by the binary mixture (A+B). After training, both groups' unrewarded responses to the mixture (A+B), odor (B), and an unconditioned control odor (X) were measured. For four out of five odor sets used in this experiment, a significant difference in digging time was observed between the responses of the two groups to odor B (P<.01), but not between their responses to the binary mixture (A+B) or to the control odor (X). These results demonstrate that pretraining rats with an odorant blocks subsequent learning about another odorant when the latter is presented simultaneously with the pretrained odorant, indicating that the components of a mixture are at least partially perceived as independent elements of this mixture.

Topics: Alcohols; Aldehydes; Animals; Conditioning, Psychological; Ethers; Learning; Male; Memory; Odorants; Olfactory Pathways; Rats; Rats, Sprague-Dawley; Salicylates; Smell; Stimulation, Chemical; Terpenes; Time Factors

To test an electrical device for determining root canal length in primary teeth in vitro, and to compare it with the radiographic length measurement.. Two examiners determined the root canal length of 24 extracted maxillary primary incisors (12 with visible root resorption and 12 without) using an electrical root canal meter (Tri Auto ZX, Morita, Dietzenbach, Germany). The instrument was left in the root canal after the second examination and a radiograph was taken. The whole tooth was cleared by immersion in methylsalicylate and subsequently photographed. Both radiographs and photographs of cleared teeth were measured and compared with the electronic measurements.. The evaluation of the radiographs showed a mean distance between the instrument tips and apices of 0.60 (+/- 0.41) mm; evaluation of the cleared teeth showed an equivalent distance of 0.62 (+/- 0.40) mm. The mean distance between instrument tip and acceptable working length (determined with the clearing method) was 0.26 (+/- 0.24) mm in teeth without resorption and 0.29 (+/- 0.30) mm in teeth with resorption.. The presence of resorption in primary teeth did not affect the accuracy of electrical measurement of root canal length in vitro. The application of this method in primary teeth should be evaluated further.

Topics: Confidence Intervals; Dental Pulp Cavity; Electric Conductivity; Electronics, Medical; Equipment Design; Fixatives; Humans; Image Processing, Computer-Assisted; Incisor; Observer Variation; Odontometry; Photography; Radiography; Reproducibility of Results; Root Resorption; Salicylates; Statistics as Topic; Surface Properties; Tooth Apex; Tooth, Deciduous

To investigate the root and canal morphology of 268 maxillary permanent molars collected from an indigenous Thai population.. The cleaned teeth were accessed, the pulp dissolved by sodium hypochlorite under ultrasonication, and the pulp system injected with Indian ink. The teeth were rendered clear by demineralization and immersion in methyl salicylate. The following observations were made: (i) number of roots and their morphology; (ii) number of root canals per root; (iii) root-canal configuration in each root using Vertucci's classification with additional modifications; and (iv) presence and location of lateral canals and intercanal communications.. All the maxillary first and second molars had three separate roots. Only, half (51%) of the maxillary third molars had three separate roots; the other half had fused or conical roots. The majority of the distobuccal (98.1-100%) and palatal (100%) roots had type I canals. Over half of the mesiobuccal roots of first (65%) and second (55%) molars had two canals. The most common (44.2%) canal configuration in mesiobuccal roots of first molars was type IV (two canals, two foramina). A variety of canal types were found in the mesiobuccal roots of second molars. Maxillary third molars showed the greatest diversity of canal morphology. There was an increase in the prevalence of lateral canals towards the apical part of the roots and intercanal communications were present in 16% of each of first, second and third Thai maxillary molars.. The mesiobuccal roots of Thai maxillary molars possessed a variety of canal system types. Over 50% of the first molars had a second mesiobuccal canal. The palatal and distobuccal canals mainly had type I canals. Only, a small proportion (7.3-13.3%) of the roots exhibited lateral canals which were the most common in the apical third

Topics: Carbon; Coloring Agents; Decalcification Technique; Dental Pulp Cavity; Ethanol; Ethnicity; Fixatives; Humans; Maxilla; Molar; Molar, Third; Salicylates; Solvents; Thailand; Tooth Apex; Tooth Root

Several forms of periodontal diseases (PD) are often associated with activated phagocytosing leukocytes and contemporary free radical production. Host antioxidant defenses could benefit from mouthrinses used as adjuncts to counteract plaque-associated bacteria. The aim of the present study was to determine possible antioxidant activity (AA) of a number of antiseptic mouthrinses and of their stated active principles (AP), regardless of their efficacy as antimicrobial agents.. The antioxidant activities of 11 mouthrinses and their active principles were tested with a specific spectrophotometric method. Comet assay was used to test whether pure chemical antioxidant activity actually corresponded to prevention of in vitro DNA fragmentation.. Methylsalicylate-containing mouthrinses were the most effective. Several compounds, and some vehicles, behaved as antioxidants. Fibroblast DNA fragmentation was limited by preincubation with methylsalicylate-containing mouthrinse but was unaffected by treatment with chlorexidine.. The results described herein indicate that several mouthrinses possess AA; such a property could be ascribed to either AP or vehicles or both. All the data were obtained in systems in vitro and the demonstration of in vivo AA is necessary. These findings could be useful in the treatment of some forms of PD and should be considered when arranging new mouthrinse formulations.

Topics: Allantoin; Analysis of Variance; Anti-Infective Agents, Local; Antioxidants; Chlorhexidine; Chlorides; Comet Assay; DNA Fragmentation; Drug Combinations; Ethanol; Fibroblasts; Humans; Mouthwashes; Oils, Volatile; Pharmaceutical Vehicles; Phosphates; Potassium Chloride; Salicylates; Sodium Fluoride; Spectrophotometry; Statistics as Topic; Terpenes; Triclosan; Zinc Compounds

Ingestion of medicated oils containing methyl salicylate poses the threat of severe, rapid-onset salicylate poisoning. In this retrospective study of 24 adults who had ingested 'White Flower Oil' (n=18) or 'Red Flower Oil' (n=6), the main objective was to determine if the risk of severe salicylate poisoning was related to the product packaging. 'Red Flower Oil' had a large bottle opening so that its content could be emptied much more easily. It also had a larger bottle size and usually had a higher methyl salicylate concentration than 'White Flower Oil'. Patients tended to ingest a greater amount of 'Red Flower Oil' than 'White Flower Oil'. Five per cent of subjects who had taken 'White Flower Oil', but 67% of subjects who had taken 'Red Flower Oil', had admission plasma salicylate level >2.2 mmol/L (P=0.006). None of the subjects who had ingested 'White Flower Oil', but 50% of subjects who had taken 'Red Flower Oil', had moderate to severe symptoms (P=0.010). As a result, none of the subjects who had ingested 'White Flower Oil', but 33% of subjects who had taken 'Red Flower Oil', required urine alkalinization (P=0.054). One patient who had taken 'Red Flower Oil' died because of hospital-acquired pneumonia. All other patients made a complete recovery. To reduce the amount of methyl salicylate that can be readily swallowed during accidental or deliberate ingestion of medicated oils, improvements are needed in the existing packaging of these products.

Topics: Adolescent; Adult; Aged; Female; Humans; Male; Middle Aged; Plant Oils; Product Packaging; Risk Factors; Salicylates

Oil of Wintergreen (methyl salicylate) is a common ingredient for liniments, ointments and essential oils used in self-treatment of musculoskeletal pain. Its pleasant smell also encourages its use to flavour confectionery. The toxic potential of this preparation is not always fully appreciated by the general public and physicians. To appreciate the danger of this oil it can be compared to aspirin tablets (325 mg dose): one teaspoon (5 ml) of Oil of Wintergreen is equivalent to approximately 7000 mg of salicylate or 21.7 adult aspirin tablets. Ingestion of as little as 4 ml in a child can be fatal. Prevention of accidental ingestion of methyl salicylate containing products can be achieved by keeping the products out of reach of children, using child resistant bottles, restricting the size of the openings of the bottles, appropriate labeling on products and reducing the salicylate content. Immediate action should be taken to treat a patient with accidental poisoning and hospitalisation is needed for monitoring and treatment. The danger of this product should be fully appreciated by both physicians and the general public. We present a case of Oil of Wintergreen poisoning with development of laryngeal oedema as a complication, general information and management issues will also be discussed.

Topics: Female; Humans; Infant; Laryngeal Edema; Poisoning; Salicylates

[figure: see text] A new methodology for the synthesis of substituted alkynes is described. In the presence of copper(I) thiophene-2-carboxylate (CuTC) or copper (I) 3-methylsalicylate (CuMeSal), the palladium-catalyzed cross-coupling of thioalkyne derivatives with boronic acids affords functionalized alkynes in yields ranging from 39 to 91%. This coupling occurs efficiently under mild, nonbasic conditions with a wide variety of thioalkynes and boronic acids, providing a reaction complementary to the Sonogashira protocol.

Topics: Alkynes; Boronic Acids; Carboxylic Acids; Catalysis; Copper; Molecular Structure; Palladium; Salicylates; Structure-Activity Relationship; Sulfur Compounds; Thiophenes

Many plant species defend themselves against herbivorous insects indirectly by producing volatiles in response to herbivory. These volatiles attract carnivorous enemies of the herbivores. Research on the model plant Arabidopsis thaliana (L.) Heynh. has contributed considerably to the unraveling of signal transduction pathways involved in direct plant defense mechanisms against pathogens. Here, we demonstrate that Arabidopsis is also a good candidate for studying signal transduction pathways involved in indirect defense mechanisms by showing that: (1) Adult females of Cotesia rubecula, a specialist parasitic wasp of Pieris rapae caterpillars, are attracted to P. rapae-infested Arabidopsis plants. (2) Arabidopsis infested by P. rapae emits volatiles from several major biosynthetic pathways, including terpenoids and green leaf volatiles. The blends from herbivore-infested and artificially damaged plants are similar. However, differences can be found with respect to a few components of the blend, such as two nitriles and the monoterpene myrcene, that were produced exclusively by caterpillar-infested plants, and methyl salicylate, that was produced in larger amounts by caterpillar-infested plants. (3) Genes from major biosynthetic pathways involved in volatile production are induced by caterpillar feeding. These include AtTPS10, encoding a terpene synthase involved in myrcene production, AtPAL1, encoding phenylalanine ammonia-lyase involved in methyl salicylate production, and AtLOX2 and AtHPL, encoding lipoxygenase and hydroperoxide lyase, respectively, both involved in the production of green leaf volatiles. AtAOS, encoding allene oxide synthase, involved in the production of jasmonic acid, also was induced by herbivory.

Topics: Adaptation, Physiological; Animals; Arabidopsis; Feeding Behavior; Fixatives; Gene Expression Regulation; Hymenoptera; Larva; Lepidoptera; Plant Leaves; Plants, Edible; Salicylates; Terpenes; Volatilization

The contents of camphor, menthol, methyl salicylate and thymol in JEIL COOL PAP were determined with gas chromatography by using a stainless steel column (2 m x 3 mm i.d.) packed with 15% DEGS, Chromosorb W (AW-DMCS) 80-100 mesh. Temperature programming was from 70 degrees C to 180 degrees C. The quantitative determination was performed with diphenyl as the internal standard. The internal standard method showed good linearity (r = 0.9995-0.9999). The average recoveries were 99.63% (camphor), 99.83% (menthol), 100.0% (methyl salicylate) and 100.4% (thymol).

Topics: Camphor; Drug Combinations; Drugs, Chinese Herbal; Menthol; Salicylates; Thymol

We compared volatiles from lima bean leaves (Phaseolus lunatus) infested by either beet armyworm (Spodoptera exigua), common armyworm [Mythimna (Pseudaletia) separata], or two-spotted spider mite (Tetranychus urticae). We also analyzed volatiles from the leaves treated with jasmonic acid (JA) and/or methyl salicylate (MeSA). The volatiles induced by aqueous JA treatment were qualitatively and quantitatively similar to those induced by S. exigua or M. separata damage. Furthermore, both S. exigua and aqueous JA treatment induced the expression of the same basic PR genes. In contrast, gaseous MeSA treatment, and aqueous JA treatment followed by gaseous MeSA treatment, induced volatiles that was qualitatively and quantitatively more similar to the T. urticae-induced volatiles than those induced by aqueous JA treatment. In addition, T. urticae damage resulted in the expression of the acidic and basic PR genes that were induced by gaseous MeSA treatment and by aqueous JA treatment, respectively. Based on these data, we suggest that in lima bean leaves, the JA-related signaling pathway is involved in the production of caterpillar-induced volatiles, while both the SA-related signaling pathway and the JA-related signaling pathway are involved in the production of T. urticae-induced volatiles.

Topics: Animals; Cyclopentanes; Fabaceae; Host-Parasite Interactions; Insecta; Larva; Oxylipins; Plant Growth Regulators; Plant Leaves; Plants, Medicinal; Salicylates; Signal Transduction; Terpenes; Volatilization

To report a case of international normalized ratio (INR) elevation resulting from the administration of topical methyl salicylate in a patient whose INR was previously stable while she received warfarin anticoagulation.. A 22-year-old white woman presented with an INR of 12.2 after applying a topical pain-relieving gel to her knees daily for eight days. The potentiation of the warfarin anticoagulation was attributed to the low-dose methyl salicylate contained in the product.. Methyl salicylate is systemically absorbed through the skin in measurable amounts, and may increase warfarin action by affecting vitamin K metabolism or by displacing warfarin from protein-binding sites. While several investigators have reported this interaction with use of high-dose methyl salicylate, this case indicates that a significant interaction can occur with the use of lower topical doses of methyl salicylate as well.. Healthcare providers and patients taking warfarin must be aware of the potential hazard of using topical methyl salicylate in combination with warfarin.

Topics: Administration, Topical; Adult; Anticoagulants; Drug Synergism; Female; Fixatives; Hemorrhage; Humans; International Normalized Ratio; Ointments; Salicylates; Warfarin

In response to herbivore damage, several plant species emit volatiles that attract natural predators of the attacking herbivores. Using spider mites (Tetranychus urticae) and predatory mites (Phytoseiulus persimilis), it has been shown that not only the attacked plant but also neighbouring plants are affected, becoming more attractive to predatory mites and less susceptible to spider mites. The mechanism involved in such interactions, however, remains elusive. Here we show that uninfested lima bean leaves activate five separate defence genes when exposed to volatiles from conspecific leaves infested with T. urticae, but not when exposed to volatiles from artificially wounded leaves. The expression pattern of these genes is similar to that produced by exposure to jasmonic acid. At least three terpenoids in the volatiles are responsible for this gene activation; they are released in response to herbivory but not artificial wounding. Expression of these genes requires calcium influx and protein phosphorylation/dephosphorylation.

Topics: Acetates; Animals; Cyclopentanes; Egtazic Acid; Fabaceae; Female; Gene Expression Regulation, Plant; Lipoxygenase; Mites; Oils, Volatile; Oxylipins; Plant Oils; Plant Proteins; Plants, Medicinal; Salicylates; Terpenes; Transcriptional Activation; Volatilization

At least two different signalling pathways have been identified that result in clearly distinguishable volatile profiles in response to pathogens and herbivores in the lima bean Phaseolus lunatus. Alamethicin, a voltage-gated ion-channel-forming peptide from Trichoderma viride, is a potent inducer of volatile biosynthesis in the lima bean. Unlike elicitation with cellulysin or herbivore damage, which act through the jasmonic acid pathway and result in a complex pattern of volatile compounds, the emitted blend comprises only the two homoterpens, 4,11-dimethylnona-1,3,7-triene and 4,8,12-trimethyltrideca-1,3,7,11-tetraene, and methyl salicylate. Both pathways, represented by jasmonic acid and alamethicin, depend on lipid-derived signalling compounds, set off by the activation of a phospholipase A and further processing by lipoxygenase activity. The alamethicin-induced signal-transduction pathway interferes with the octadecanoid cascade, probably due to increased salicylic acid levels, resulting in an inhibition of the typical jasmonic acid-induced volatile profile.

Topics: Alamethicin; Fabaceae; Plants, Medicinal; Salicylates; Signal Transduction; Terpenes

To evaluate the efficacy of a fluoride dentifrice containing a fixed combination of essential oils (Thymol, Menthol, Eucalyptol, and Methyl Salicylate) in preventing caries in Sprague Dawley rats.. The dentifrice contains 0.76% sodium monofluorophosphate (SMFP) as the fluoride source and a silica abrasive system. A fluoride-free placebo and a clinically proven USP dentifrice reference standard for SMFP/silica were included as controls. Three groups of 45 SDV-free Sprague Dawley weanlings were infected by a cariogenic strain of Streptococcus sobrinus and fed cariogenic diet NIH 2000 ad libitum. Animals were treated twice daily (once on weekends) with the assigned dentifrice using a cotton-tipped applicator, for 5 wks, after which they were terminated and caries scored using Larson's modification of the Keyes method.. Analyses of variance were used to compare inter-group means, the total E lesion score was the primary efficacy variable. Compared with the fluoride-free vehicle control, the experimental dentifrice and USP reference standard dentifrice produced a statistically significant reductions of 18.3% and 12.2% respectively for total caries score (P<0.001). Compared with the clinically tested USP positive control dentifrice, the experimental dentifrice produced a statistically significant reduction in the total caries score of 6.9% (P=0.028). The results of this study show that 1) both the new dentifrice containing essential oils and USP dentifrice are statistically significantly effective in reducing caries in the rat model, 2) the anticaries activity of the SMFP dentifrice is not adversely affected with the addition of essential oils.

Topics: Analysis of Variance; Animals; Anti-Infective Agents, Local; Cariostatic Agents; Cyclohexanols; Dental Caries; Dental Plaque; Dentifrices; Diet, Cariogenic; Disease Models, Animal; Eucalyptol; Eucalyptus; Fluorides; Gingivitis; Menthol; Monoterpenes; Oils, Volatile; Pharmaceutical Vehicles; Phosphates; Placebos; Random Allocation; Rats; Rats, Sprague-Dawley; Salicylates; Silicon Dioxide; Single-Blind Method; Streptococcus sobrinus; Terpenes; Thymol

To determine how changes in cutaneous blood flow induced in-vivo by methylsalicylate (MeSA), compared to non-rubefacient triethanolamine salicylate (TSA), affected topical salicylate absorption and distribution, and to assess formulation therapeutic potential by comparing tissue concentrations to published antiinflammatory concentrations.. Flux of salicylate from MeSA and TSA formulations applied to full-thickness rat skin was determined using in vitro diffusion cells. Anaesthetised rats were then used to quantify salicylate concentrations in plasma and tissues underlying the application site for the two formulations over a 6h period. In vitro and in vivo absorption profiles were then compared and the effect of MeSA on cutaneous blood flow assessed.. In vitro flux of salicylate from the MeSA formulation was 40% higher, though after correcting for differences in formulation concentrations the ratio of permeability coefficients was reversed. Contrary to the in vitro predictions, in vivo tissue and plasma concentrations of salicylate in rats rose rapidly in the first 1 hr and were more than the predicted 1.4-fold higher for MeSA. This effect was mirrored by the increase in blood flow induced by MeSA in human cutaneous vessels and that reported in the literature. Potential therapeutic levels were not seen below superficial muscle layers.. Direct tissue penetration of salicylate occurs below application sites from both MeSA and TSA formulations. Tissue concentrations of MeSA were higher than predicted due to its rapid distribution in the blood.

Topics: Administration, Topical; Animals; Anti-Inflammatory Agents, Non-Steroidal; Laser-Doppler Flowmetry; Male; Rats; Rats, Wistar; Regional Blood Flow; Salicylates; Skin Absorption; Tissue Distribution

Analytical methods using gas chromatography-flame ionization detection (GC-FID) for the quantitation of camphor and menthol and GC-MS for the quantitation of methyl salicylate have been developed for measurement of low concentrations from human plasma. Anethole serves as the internal standard for camphor and menthol and ethyl salicylate serves as the internal standard for methyl salicylate. Plasma samples undergo multiple, sequential extractions with hexane in order to provide optimal recovery. For menthol and camphor, the extracting solvent is reduced in volume and directly injected onto a capillary column (Simplicity-WAX). Extracted methyl salicylate is derivatized with BSTFA prior to injection onto a capillary column (Simplicity-5). Between-day variation (% RSD) at 5 ng/ml varies from 6.2% for methyl salicylate to 13.5% for camphor. The limit of detection for each analyte is 1 ng/ml and the limit of quantitation is 5 ng/ml. These analytical methods have been used in a clinical study to assess exposure from dermally applied patches containing the three compounds.

Topics: Camphor; Chromatography, Gas; Humans; Menthol; Reproducibility of Results; Salicylates

Topics: Aged; Drug Overdose; Drugs, Chinese Herbal; Fatal Outcome; Female; Humans; Salicylates

The penetration of active ingredients from topically applied anti-inflammatory pharmaceutical products into tissues below the skin is the basis of their therapeutic efficacy. There is still controversy as to whether these agents are capable of direct penetration by diffusion through the tissues or whether redistribution in the systemic circulation is responsible for their tissue deposition below the application site.. The extent of direct penetration of salicylate from commercial ester and salt formulations into the dermal and subcutaneous tissue of human volunteers was determined using the technique of cutaneous microdialysis. We also examined differences in the extent of hydrolysis of the methylester of salicylate applied topically in human volunteers and in vitro skin diffusion cells using full-thickness skin and epidermal membranes.. The present study showed that whilst significant levels of salicylate could be detected in the dermis and subcutaneous tissue of volunteers treated with the methylsalicylate formulation, negligible levels of salicylate were seen following application of the triethanolamine salicylate formulation. The tissue levels ofsalicylate from the methylsalicylate formulation were approx. 30-fold higher than the plasma concentrations.. The absorption and tissue concentration profiles for the commercial methylsalicylate formulation are indicative of direct tissue penetration and not solely redistribution by the systemic blood supply.

Topics: Administration, Topical; Adult; Cells, Cultured; Diffusion; Female; Humans; Hydrolysis; In Vitro Techniques; Male; Microdialysis; Salicylates; Skin; Skin Absorption

Epidermal cells produce various kinds of cytokines and express cell adhesion molecules. To analyze early events which induced in human epidermis by stimulation with various chemicals, we analyzed mRNA of cytokines expressed in epidermis in a human skin organ culture system. After painting haptens, primary irritants or vehicle control on human skin specimens sliced to 1 mm thickness and cut into approximately 5 x 5 mm blocks, the pieces were cultured in serum-free medium. After separating epidermis from dermis, total RNA was extracted and mRNA of cytokines was assessed by the reverse transcriptase-poly-merase chain reaction. Only haptens induced IL-1 beta mRNA at 1-3 hours. TNF-alpha mRNA was induced 9 hours after application of haptens and 1 hour after application of primary irritants. IL-1 alpha mRNA was not induced by either haptens or primary irritants. Thus, cytokine mRNA expression induced by haptens in epidermis differs from that induced by primary irritants.

Topics: Acetone; Cell Adhesion Molecules; Culture Media, Serum-Free; Culture Techniques; Cytokines; Dinitrochlorobenzene; Epidermis; Ethanol; Haptens; Humans; Interleukin-1; Irritants; Keratolytic Agents; Pharmaceutical Vehicles; Phenylenediamines; Polymerase Chain Reaction; RNA, Messenger; Salicylates; Skin; Solvents; Time Factors; Tretinoin; Tumor Necrosis Factor-alpha

Local lymph node activation and increased total serum IgE levels are suggested to be predictive parameters of airway hypersensitivity caused by low molecular weight (LMW) chemicals. Whether increases of total serum IgE are indicative of actual induction of specific airway reactions (morphological and functional) after inhalation challenge was examined in the present study. In Brown Norway (BN) and Wistar rats, serum IgE concentrations were examined following topical exposure of chemicals with known diverse sensitization potential in humans: trimellitic anhydride (TMA), a dermal and respiratory sensitizer; dinitrochlorobenzene (DNCB), a dermal sensitizer with no known potential to cause respiratory allergy; and methyl salicylate, a skin irritant devoid of sensitizing properties. Functional and histopathological changes in the respiratory tract were examined after subsequent inhalatory challenge with these chemicals. Of the three tested chemicals, only topical exposure to TMA resulted in a significant increase in total serum IgE concentrations in the high-IgE-responding BN rat. Upon subsequent inhalatory challenge of these rats, TMA induced specific airway reactions which included a sharp decrease in respiratory rate during challenge, followed by an increase in breathing rate with a concomitant decrease in tidal volume 24 and 48 h after inhalatory challenge, and histopathological changes in the larynx and lungs of animals necropsied 48 h after challenge. Interestingly, despite low IgE levels, TMA induced histopathological changes in the larynx and lungs of Wistar rats too. Laryngeal changes were also observed in Wistar rats upon sensitization and challenge with DNCB. These data suggest that increased total serum IgE after topical sensitization is associated with immediate-type specific airway reactivity after inhalation challenge in BN rats and thus may be a valuable parameter in testing for respiratory sensitization potential of LMW compounds. Histopathological examination upon subsequent inhalation challenge of sensitized low-IgE-responders may provide information on other allergic inflammatory airway reactions.

Topics: Allergens; Animals; Body Weight; Bronchi; Dermatitis, Allergic Contact; Dinitrochlorobenzene; Female; Immunoglobulin E; Organ Size; Phthalic Anhydrides; Rats; Rats, Inbred BN; Rats, Wistar; Respiratory Function Tests; Respiratory Hypersensitivity; Salicylates

To evaluate the efficacy of a decontamination station following exposure of volunteers to liquids with physical characteristics comparable to sarin and mustard gas.. Twenty-four volunteers participated in the experiment which was performed with all staff wearing personal protective equipment including respiratory protection. The clothes, skin, and hair of the volunteers were contaminated with the simulated liquid phase contaminants, ethyl lactate and methyl salicylate. Sulphur hexafluoride gas was used to confirm the ventilation efficacy. Decontamination followed guidelines using a two-stage procedure. In the first chamber, all volunteers received a 3-minute shower with water at 30 degrees C, and their clothes but not their respiratory masks were removed. In the second, they were twice washed thoroughly with soap and water. After decontamination, the volunteers entered a third chamber for first aid measures.. The air concentration of sulphur hexafluoride was reduced by 1:10,000 between the first and the third chambers. Ethyl lactate and methyl salicylate were measured in low concentrations in the third chamber. The capacity was 16 volunteers per hour with two-thirds on stretchers. After self-decontamination of the staff, the concentration of ethyl lactate increased significantly in the third chamber, consistent with residual ethyl lactate adsorbed by their underwear. This observation revealed a deficiency in the guidelines for self-decontamination.. The capacity of the decontamination unit was found to be 16 volunteers per hour. The ventilation system and guidelines of the decontamination unit were demonstrated to be effective under the conditions examined. The self-decontamination of the staff was not optimal.

Topics: Accidents, Occupational; Adolescent; Adult; Chemical Warfare Agents; Decontamination; Female; Hospital Units; Hospitals, Urban; Humans; Lactates; Male; Management Audit; Middle Aged; Mustard Gas; Salicylates; Sarin; Sulfur Hexafluoride; Sweden; Ventilation; Workforce

A gas chromatographic-mass spectrometric (GC-MS) assay was developed for the quantitative analysis of methyl salicylate (MeS), ethyl salicylate (ES) and salicylic acid (SA) from biological fluids. The method was validated from 100-microl rat liver homogenate preparations (5 mg/ml protein) in 70 mM KH2PO4 (pH 7.4) buffer and from 100 microl rat plasma. The samples were extracted with chloroform, derivatized with BSTFA and quantitated by GC-MS in the SIM mode. The standard curves ranged from 31 ng/ml to 800 or 1250 ng/ml. Relative standard deviations and bias were less than 11% in plasma and homogenate for all compounds except SA which evidenced greater variability. The assay was used in preliminary experiments to characterize the pharmacokinetics of MeS in rats.

Topics: Animals; Body Fluids; Gas Chromatography-Mass Spectrometry; Liver; Male; Rats; Rats, Sprague-Dawley; Salicylates; Salicylic Acid; Sensitivity and Specificity

The murine local lymph node assay is a method for predictive testing of contact allergenicity, but its ability to discriminate between allergens and irritants has been questioned. To explain some of the conflicting results with irritants, the proliferation induced by methyl salicylate and nonanoic acid, both considered to be non-sensitisers, was further investigated. Both substances showed a dose--response relationship and clearly positive results when tested at higher concentrations (> or = 50%) and would thus be classified as potential sensitisers according to the present criteria for a positive assay result. In the case of methyl salicylate, the use of either dimethyl formamide or methyl ethyl ketone as vehicle did not significantly influence the results. The negative results obtained for methyl salicylate in some earlier reports were probably due to testing at too low concentrations. The proliferation induced by irritants such as methyl salicylate and nonanoic acid and inter alia sodium dodecyl sulfate, Triton X-100, oxalic acid, chloroform/methanol (2:1) must be better recognized and elucidated before the assay can be generally accepted as a predictive test method.

Topics: Allergens; Animals; Butanones; Cell Division; Chloroform; Detergents; Dimethylformamide; Dose-Response Relationship, Drug; Fatty Acids; Female; Fixatives; Irritants; Lymph Nodes; Methanol; Mice; Mice, Inbred CBA; Mice, Inbred Strains; Octoxynol; Oxalic Acid; Pharmaceutical Vehicles; Predictive Value of Tests; Reducing Agents; Salicylates; Sodium Dodecyl Sulfate; Solvents; Surface-Active Agents

The double-quantum-filtered carbon-carbon correlation experiment (INADEQUATE) can be accelerated significantly through a reduction in the spin-lattice relaxation times by dissolving oxygen gas in the solution. The effect is enhanced by lowering the temperature and by pressurizing the sample tube with oxygen. This offers a fourfold reduction in the relaxation times of the carbon-13 resonances in the 125-MHz spectrum of methyl salicylate. The addition of perfluorotertiarybutanol (related to the artificial blood substitutes) increases the amount of oxygen that can be dissolved, so that without oxygen pressurization, similar reductions in the relaxation times can be achieved. The nuclear Overhauser enhancements are only slightly reduced by addition of oxygen. Polarization transfer from the directly attached protons (INEPT) further increases the sensitivity if at least one of the two coupled carbon sites is protonated, principally because the proton spin-lattice relaxation times of oxygenated samples are shortened by the relaxation agent. These modest improvements in sensitivity are in general complementary to existing enhancement schemes.

Topics: Blood Substitutes; Carbon; Carbon Isotopes; Chloroform; Cold Temperature; Deuterium; Electron Spin Resonance Spectroscopy; Fluorocarbons; Image Enhancement; Magnetic Resonance Spectroscopy; Oxygen; Pressure; Protons; Salicylates; Solubility; tert-Butyl Alcohol; Viscosity

Experiments have been made on the solid adsorption and stability of the essential oil extracted from Gaultheria yunnanensis. The results show that among the chemical constituents of the oil, methyl salicylate accounts for 99.66%. Grain adsorbents of aluminum hydroxide gel have been proved useful in obtaining higher release rates of the oil at required temperatures as well as keeping the oil stable at room temperature.

Topics: Adsorption; Drug Carriers; Drugs, Chinese Herbal; Hot Temperature; Magnoliopsida; Oils, Volatile; Plants, Medicinal; Salicylates; Technology, Pharmaceutical

The local lymph node assay (LLNA) and the IgE test in the mouse are proposed models for predictive recognition of low molecular weight chemicals causing IgE-mediated allergic airway reactions in man. Since rats are commonly used in routine toxicity studies and a previous study (Arts et al. (1996) Food Chem. Toxicol. 34, 55-62) has shown that several rat strains were found appropriate for the LLNA, the suitability of the rat for the IgE test was examined in the present study. Serum IgE concentrations were examined following topical exposure of Brown Norway (BN) and Wistar rats to each of four chemicals with known diverse sensitization potential in humans: trimellitic anhydride (TMA), a dermal and respiratory sensitizer, dinitrochlorobenzene (DNCB), a dermal sensitizer with no or limited potential to cause respiratory allergy; formaldehyde (FA), a skin irritant and dermal sensitizer with equivocal evidence for respiratory sensitizing potential; methyl salicylate (MS), a skin irritant devoid of sensitizing properties. Of the four tested chemicals, only exposure to TMA resulted in a significant increase in serum IgE concentration and this response was only evoked in the high-IgE-responding BN rat. The latter two chemicals were also tested for lymph node activation, in casu the ear-draining lymph nodes. FA caused a dose-dependent activation of the draining lymph nodes whereas MS was inactive. The results as obtained with TMA, DNCB and MS in the rat are in agreement with human data. The results with FA though, indicate the need for further studies of chemicals that have both irritant and sensitizing properties at about similar concentrations or may act through non-IgE-mediated immune mechanisms.

Topics: Administration, Cutaneous; Allergens; Animals; Cell Count; Cell Division; Dermatitis, Contact; Dinitrochlorobenzene; Dose-Response Relationship, Drug; Female; Formaldehyde; Immunoglobulin E; Lymph Nodes; Organ Size; Phthalic Anhydrides; Rats; Rats, Wistar; Salicylates; Skin Tests

Topics: Animals; Body Weight; Dose-Response Relationship, Drug; Female; Flavoring Agents; Male; Mice; Perfume; Pregnancy; Reproduction; Salicylates

Topics: Animals; Birth Weight; Body Weight; Dose-Response Relationship, Drug; Female; Fertility; Flavoring Agents; Litter Size; Male; Mice; Perfume; Pregnancy; Reproduction; Salicylates

Topics: Administration, Cutaneous; Humans; Salicylates; Skin

In Exp. 1, the "protheticity" of the pleasantness of a diverse set of relatively isointensive odorants was estimated using exponents from power functions fitted by an interative least squares procedure between scale values established by (a) magnitude estimation and (b) category rating and rank ordering. In Exp. 2, this procedure was applied to intensity data derived from quarter-log-step volume dilution series of two hedonically disparate odorants, furfural and methyl salicylate. The goodness of fit of the power functions was somewhat better for the intensity than for the pleasantness data. The pleasantness dimension of the diverse stimuli was slightly prothetic (respective category scaling and rank order/magnitude estimation exponents = 0.60 and 0.63). The intensity dimension of furfural was considerably more prothetic than that of methyl salicylate (respective category/magnitude estimation exponents = 0.20 and 0.68; respective rank order/magnitude exponents = 0.21 and 0.69). These data suggest that the degree of olfactory protheticity depends upon the stimuli as well as the attributes chosen for investigation and support the view that Stevens' metathetic/prothetic dichotomy has little utility in classifying the scaling attributes of odors. Whether the degree of protheticity reflects the nature or distribution of olfactory system receptive elements within the main olfactory pathway remains an empirical question which awaits a more specific understanding of the nature of olfactory coding at the level of the neuroepithelium.

Topics: Adult; Esthetics; Female; Furaldehyde; Humans; Male; Odorants; Psychophysics; Salicylates; Semantic Differential; Smell

In view of the toxic potential of medicated oils containing methyl salicylate, we have studied the existing packaging of 10 commonly used preparations from Hong Kong and Singapore and identified areas for improvement with respect to the prevention of poisonings. They were all packed in translucent bottles without child-resistant closures. The methyl salicylate content ranged from 15 to 67%. Many preparations also contained other potentially toxic ingredients in significant amounts, such as turpentine oil and camphor. The contents of the larger bottles could generally be emptied more easily because of the greater size of their openings. The product with the highest methyl salicylate content also had the biggest opening of all. The threat from ingestion of medicated oils containing methyl salicylate can probably be 'reduced' by: (i) using child-restraint closures; (ii) restricting the size of both the openings and the bottles; and (iii) reducing the methyl salicylate content.

Topics: Camphor; Drug Packaging; Fixatives; Hong Kong; Poisoning; Product Surveillance, Postmarketing; Salicylates; Singapore; Solvents; Turpentine

In Hong Kong, medicated oils containing methyl salicylate account for 48% of acute salicylate poisoning cases treated in the general medical ward of the Prince of Wales Hospital. To quantify better the risk to average persons who have intentionally ingested these medicated oils, the methyl salicylate content and bottle size of 7 commonly available formulations were examined. Koong Yick Hung Far Oil had the highest methyl salicylate content (67%) and was available only in 60-ml bottles. If the entire bottle of this product were ingested, the equivalent of 184 adult 300-mg aspirin tablets would have been swallowed. Accidental ingestions of as little as 6 ml of Koong Yick Hung Far Oil by a child can be fatal. Six other products contained 15-40% methyl salicylate and their biggest bottle sizes range from 28-57 ml. Among medicated oils commonly found in Hong Kong, Koong Yick Hung Far Oil poses the greatest threat for severe salicylate poisoning if swallowed because of its high salicylate content and its availability in 60-ml bottles. The threat from medicated oils can probably be reduced by restricting their bottle size and methyl salicylate concentration. Physicians and clinical toxicologists should appreciate the toxic potential of these products.

Topics: Adult; Child; Hong Kong; Humans; Molecular Weight; Oils; Product Surveillance, Postmarketing; Salicylates

Topics: Animals; Fixatives; Paraffin Embedding; Salicylates

The method is based upon the reaction between fluoride ions and the coloured complex of Fe(III) with methyl salicylate to form the stable, colourless hexaflouride complex of iron. The conditions of the method (pH, time and combination ratio) were studied and a standard curve was obtained for 0.01-0.08 mg NaF ml-1, at 525 nm. A study was conducted on interference with complexing anions of Fe(III), cations that react with fluoride ions and with common ingredients of dosage forms and dental preparations. The method was validated and the results showed good precision (100.16 +/- = 2.33%) comparable with that of other analytical methods. Good results were obtained in the spectrophotometric determination of fluoride ions in a stomatological gel and in a toothpaste.

Topics: Dentifrices; Dosage Forms; Ferric Compounds; Fluorides, Topical; Gels; Potentiometry; Salicylates; Sodium Fluoride; Spectrophotometry, Ultraviolet; Tablets; Toothpastes

Apart from isolated reports of severe salicylate poisoning after ingesting an unusually large amount of a medicinal oil, there are no published data on the threat arising from attempted suicide with topical medicaments containing methyl salicylate or wintergreen oil compared with aspirin tablets. In this retrospective study, the admission plasma salicylate concentrations and clinical presentations were compared in 80 subjects who had taken aspirin tablets (n = 42) or topical medicaments (n = 38). The proportions of subjects being symptomatic were similar in the two groups. Although the admission plasma salicylate concentrations were generally higher in subjects who had ingested aspirin tablets, the two highest readings (4.3 and 3.5 mmol/1) belonged to two of the subjects who had taken topical medicaments. Because of its liquid, concentrated form and lipid solubility, methyl salicylate poses the threat of severe, rapid-onset salicylate poisoning. The toxic potential of topical medicaments containing methyl salicylate or wintergreen oil should be fully appreciated by both physicians and the general public.

Topics: Adolescent; Adult; Aged; Aged, 80 and over; Aspirin; Female; Humans; Male; Middle Aged; Poisoning; Retrospective Studies; Salicylates; Suicide, Attempted; Time Factors

Most personal defense sprays contain o-chlorobenzylidene malononitrile (CS), w-chloroacetophenone (CN), oleoresin capsicum (OC), or a combination of these ingredients as the active agent. They are designed to incapacitate by causing acute ocular irritation, lacrimation, conjunctivitis, blepharospasm, and mild to moderate respiratory distress.. To assess the ocular effects of sprays containing OC as the active agent. Snellen visual acuities and anterior segment appearances of 22 police officers were determined before and after spray exposure. To assess the effects of OC spray contamination on soft contact lenses, four brands of lenses were sprayed and cleaned twice with an alcohol-based cleaner. Gas chromatography was used to search for residual OC in the lenses.. All officers experienced intense blepharospasm, lacrimation, conjunctivitis, and incapacitation as the result of spray exposure. Acute effects lasted about 5 to 10 min, with relatively complete recovery occurring in about 30 to 60 min. All had significant conjunctivitis, and some had water-drop-shaped corneal defects that stained with fluorescein. These defects resolved within 24 hours without treatment. OC residue was found to be present in the soft lenses that had been sprayed and cleaned twice.. Optometrists can manage uncomplicated spray exposure patients by directing at-home irrigation with water, and following up with an in-office examination. Soft lenses contaminated by OC spray should be discarded.

Topics: Aerosols; Blepharospasm; Burns, Chemical; Capsicum; Chromatography, Gas; Conjunctivitis; Contact Lenses; Eye Burns; Eye Protective Devices; Humans; Irritants; Lacrimal Apparatus Diseases; Plant Extracts; Plants, Medicinal; Salicylates; Visual Acuity

Two new alcoholic aroma precursors, cis- and trans-linalool, 3,7-oxides 6-O-beta-D-apiofuranosyl-beta-D-glucopyranosides (1 and 2), as well as two already known compounds, (Z)-3-hexenyl beta-D-glucopyranoside (3) and methyl salicylate 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside (beta-primeveroside: 4), and another new monoterpendiol glycoside, 8-hydroxygeranyl beta-primeveroside (5) have recently been isolated as aroma precursors in tea leaves (Camellia sinensis var. sinensis cv. Maoxie) ready for oolong tea processing.

Topics: Carbohydrate Sequence; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Glucosides; Glycosides; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Odorants; Salicylates; Spectrometry, Mass, Fast Atom Bombardment; Tea

Topics: Aged; Drug Combinations; Drugs, Chinese Herbal; Herb-Drug Interactions; Humans; Male; Phenanthrolines; Plant Extracts; Salicylates; Salvia miltiorrhiza; Self Medication; Warfarin

Using rat paw dextran edema, the antiexudative activity of the complexes of the composition Cu(RCOO)2.nH2O--R represents 2-hydroxy-Y-phenyl: Y = 3 (n = 1,5), Y = 4 (4), Y = 5 (2) or 2-hydroxy-3,6-dimethylphenyl (n = 4)--and of the corresponding uncomplexed acids was assayed. Salicylic and acetylsalicylic acids and their Cu(II) salts were used as standards of comparison. The compounds were administered i.p. in a single dose of 10 mg/kg body weight. In general, the acids were more effective than their copper(II) salts except for the pair m-cresotic acid--Cu(II) complex. Only p-cresotic acid (mean edema reduction 56%) and copper(II) m-cresotate tetrahydrate (43%) exhibited a biological activity comparable to those of salicylic acid (62%) and copper(II) salicylate tetrahydrate (70%). The observed activities of complexes are discussed in relation to their proposed structures.

Topics: Animals; Copper; Edema; Rats; Salicylates

Topics: Adult; Drugs, Chinese Herbal; Female; Humans; Salicylates; Suicide, Attempted

The murine local lymph node assay is a predictive test for the identification of skin-sensitizing chemicals. The method has been the subject both of national inter-laboratory studies and of extensive comparisons with guinea pig tests. In the investigations reported here, the local lymph node assay has been evaluated further in the context of an international study comprising five independent laboratories. In addition, the influence of minor modifications to the standard assay procedure on the performance of the test has been examined. The modified procedures investigated were exposure of mice for 4 rather than 3 consecutive days, excision of lymph nodes 4 rather than 5 days after the initiation of exposure and the use of an alternative isotope. All five laboratories, irrespective of whether the standard or a modified protocol was used, were able to identify accurately, and with comparable sensitivity, potassium dichromate and 2,4-dinitrochlorobenzene as skin sensitizers. Using standard criteria, none of the laboratories recorded positive responses with methyl salicylate, a non-sensitizer. In the standard protocol, lymph nodes are pooled for each experimental group and the vigor of responses measured as a stimulation index relative to vehicle controls. A stimulation index of 3 or greater is considered to indicate skin-sensitizing potential. One further modification adopted by three of the laboratories was to analyze nodes from individual animals and, thereby, permit statistical evaluation. This allowed a direct comparison of statistical significance with the conventional stimulation index as criteria for a positive response. The data indicate that, while statistical evaluation may provide, in some instances, for small increases in sensitivity, this may be at the expense of some loss of selectivity. There are, however, insufficient data presently to draw firm conclusions regarding the relative value of statistical analysis. These studies demonstrate that the local lymph node assay is sufficiently robust to accommodate minor procedural and technical modifications without material changes in test performance.

Topics: Analysis of Variance; Animals; Caustics; Dermatitis, Allergic Contact; Dinitrochlorobenzene; Dose-Response Relationship, Drug; Female; International Cooperation; Irritants; Lymph Nodes; Lymphocyte Activation; Mice; Mice, Inbred CBA; Potassium Dichromate; Reference Standards; Salicylates; Skin

Topics: Drug Labeling; Hong Kong; Nonprescription Drugs; Salicylates

Studies to determine the extent of local tissue penetration of topically applied, commercially available salicylate esters and salts were conducted in male Wistar rats. The salicylate concentration in plasma, tissues underlying the site of drug application, and similar tissues on the contralateral (control) side were measured. The plasma and tissue salicylate levels suggest that direct penetration of salicylate was predominant to the top muscle level on the treated site. Results also suggest that the drugs were first absorbed into the bloodstream and subsequently distributed to both the deeper tissues on the treated site and the contralateral tissues. The topical application of formulations of ester methyl salicylate and salts triethanolamine salicylate and diethylamine salicylate containing comparable salicylate concentrations yielded similar salicylate concentrations in the various tissues. The salicylate concentrations in the deeper tissues approached concentrations observed in the contralateral tissues suggesting that salicylate present in these tissues was due to the systemic blood supply.

Topics: Administration, Topical; Animals; Male; Rats; Rats, Wistar; Salicylates; Skin Absorption

Topics: Aspirin; Asthma; Flavoring Agents; Humans; Parabens; Salicylates; Toothpastes

Traditional medicine is practised to some degree in all cultures. Many different types of herbal preparations and "oils" are widely used in Malaysia, too. We report a case of acute salicylism due to accidental ingestion of one brand of such oils. Compulsory labelling of traditional drugs with their chemical ingredients is suggested for proper and timely management of such cases.

Topics: Blood Chemical Analysis; Drug Overdose; Epilepsy, Tonic-Clonic; Humans; Infant; Malaysia; Male; Medicine, Traditional; Metabolic Clearance Rate; Salicylates

Retinyl palmitate, a widely used ingredient in cosmetic products, is promoted for its beneficial effects on the appearance of skin. Previous studies suggest that enzymes are available in skin to metabolize this ingredient during skin absorption. Esterase activity hydrolyzes retinyl palmitate to retinol (vitamin A), which is oxidized in many tissues to retinoic acid primarily by alcohol dehydrogenase. The activities of esterase and alcohol dehydrogenase were characterized in hairless guinea pig skin by using flow-through diffusion cells and radiolabeled model compounds (methyl salicylate and benzyl alcohol) previously shown to be metabolized by these enzymes. Methyl salicylate was hydrolyzed by esterase to a greater extent in viable skin than in nonviable skin. Glycine conjugation of salicylic acid and benzoic acid occurred only in viable skin. The metabolism of methyl salicylate and benzyl alcohol occurred to a greater extent in male guinea pig skin than in female guinea pig skin. The percutaneous absorption of both radiolabeled compounds was similar in viable and nonviable skin. About 30 and 18% of topically applied retinyl palmitate were absorbed from an acetone vehicle by hairless guinea pig skin and human skin, respectively. Less than 1% of the applied dose of this lipophilic compound diffused from skin into the receptor fluid. Retinol was the only detectable metabolite of retinyl palmitate in both hairless guinea pig and human skin. In human skin, 44% of the absorbed retinyl palmitate was hydrolyzed to retinol. The use of retinyl palmitate in cosmetic formulations may result in significant delivery of retinol into the skin.

Topics: Alcohol Dehydrogenase; Animals; Anticarcinogenic Agents; Benzyl Alcohols; Chromatography, High Pressure Liquid; Diffusion; Diterpenes; Esterases; Female; Guinea Pigs; Humans; In Vitro Techniques; Male; Retinyl Esters; Salicylates; Sex Characteristics; Skin; Skin Absorption; Vitamin A

Pseudomonas putida CSV86, a soil bacterium, grows on 1- and 2-methylnaphthalene as the sole source of carbon and energy. In order to deduce the pathways for the biodegradation of 1- and 2-methylnaphthalene, metabolites were isolated from the spent medium and purified by thin layer chromatography. Emphasis has been placed on the structural characterisation of isolated intermediates by GC-MS, demonstration of enzyme activities in the cell free extracts and measurement of oxygen uptake by whole cells in the presence of various probable metabolic intermediates. The data obtained from such a study suggest the possibility of occurrence of multiple pathways in the degradation of 1- and 2-methylnaphthalene. We propose that, in one of the pathways, the aromatic ring adjacent to the one bearing the methyl moiety is oxidized leading to the formation of methylsalicylates and methylcatechols. In another pathway the methyl side chain is hydroxylated to -CH2-OH which is further converted to -CHO and -COOH resulting in the formation of naphthoic acid as the end product. In addition to this, 2-hydroxymethylnaphthalene formed by the hydroxylation of the methyl group of 2-methylnaphthalene undergoes aromatic ring hydroxylation. The resultant dihydrodiol is further oxidised by a series of enzyme catalysed reactions to form 4-hydroxymethyl catechol as the end product of the pathway.

Topics: Biodegradation, Environmental; Carboxylic Acids; Catechols; Hydroxylation; Naphthalenes; Pseudomonas putida; Salicylates

Topics: Adult; Aerosols; Analgesics; Benzyl Alcohol; Benzyl Alcohols; Camphor; Dermatitis, Allergic Contact; Female; Humans; Male; Menthol; Salicylates

Topics: Air Pollution; Animals; Blood; Flavoring Agents; Guinea Pigs; Hygiene; Immune System; Lethal Dose 50; Male; Maximum Allowable Concentration; Nervous System; Rats; Salicylates

Certain adverse reactions to aspirin (ASA), nonsteroidal anti-inflammatory drugs (NSAIDs) and pyrazoline derivatives resemble IgE-mediated hypersensitivity. However, convincing evidence of antigen-antibody interactions or of the inhibition of the cyclooxygenase pathway of arachidonic acid metabolism leading to an increase in the generation of leukotrienes (LTs) and a decrease in the generation of prostaglandins (PGs) was not fully demonstrated. In this study, two types of specific IgE antibodies have been found in 27 serum samples from 28 ASA-sensitive patients with salicyloyl-discs and O-methylsalicyloyl-discs by Radio Allergo Sorbent Tests (RAST). The positive rates were 96.4% and 71.4%, respectively. In contrast, no positive results could be found in 10 normal donors without ASA sensitivity after ingestion of ASA 500 mg/day for 14 days. Further investigation of the chemical structure of epitopes was done by cross inhibition studies. Our results are an increasing evidence in favour of an IgE-dependent mechanism in patients suffering from ASA sensitivity. Hopefully, the determination of specific IgE antibodies will be a safe diagnostic method of ASA sensitivity in vitro.

Topics: Adult; Aged; Aged, 80 and over; Aspirin; Drug Hypersensitivity; Female; Humans; Immunoglobulin E; Male; Middle Aged; Radioallergosorbent Test; Salicylates; Salicylic Acid

A methyl salicylate-buffered, croton oil-containing 50% salicylic acid ointment peel, following pretreatment with topical tretinoin and localized 20% trichloroacetic acid, is extremely effective for removal of lentigines, pigmented keratoses, and actinically damaged skin from the dorsum of the hands and forearms. The ease of application, uniform results, decreased risk of scarring, and one-time application of this peel, in comparison with other methods used for treatment of these aging-skin changes, warrants consideration by the dermatologic surgeon.

Topics: Aged; Bandages; Chemexfoliation; Dermatitis, Seborrheic; Female; Forearm; Hand Dermatoses; Humans; Keratosis; Lentigo; Ointments; Pigmentation Disorders; Salicylates; Salicylic Acid; Tretinoin; Trichloroacetic Acid

Three low molecular weight compounds were found in hexane:diethyl ether extracts of fed males of the African ticks, Amblyomma variegatum (tropical bont tick) and A. hebraeum (bont tick), namely, o-nitrophenol, methyl salicylate and 2,6-dichlorophenol. These same compounds were also fond in a rinse of fed A. variegatum males, but were absent or present in only trace amounts in a rinse of fed A. hebraeum males, o-Nitrophenol and methyl salicylate were present in much higher concentrations (i.e., amounts/tick) in A. variegatum than in A. hebraeum. 2,6-Dichlorophenol was also more abundant in A. variegatum than in A. hebraeum, but the differences were not as great as with the former two compounds. Extraction in hexane over a 3-week period revealed four additional compounds, benzaldehyde, benzyl alcohol, benzothiazole and nonanoic acid. The first three compounds were found in males of both species; nonanoic acid was found only in A. hebraeum males. Published reports consistently show strong attraction by o-nitrophenol and methyl salicylate for both sexes of the two bont tick species; 2,6-dichlorophenol and benzaldehyde have been reported to be attractive to both sexes of A. hebraeum. The possible roles of these compounds, as well as others occasionally reported from A. hebraeum and A. variegatum, as components of the aggregation/attachment pheromone or other pheromones is discussed.

Topics: Animals; Arachnid Vectors; Benzaldehydes; Benzothiazoles; Benzyl Alcohol; Benzyl Alcohols; Chlorophenols; Chromatography, Gas; Fatty Acids; Feeding Behavior; Female; Gas Chromatography-Mass Spectrometry; Heartwater Disease; Male; Nitrophenols; Salicylates; Sex Attractants; Sexual Behavior, Animal; Thiazoles; Tick Infestations; Ticks

Methyl salicylate, a commonly used chemical counterirritant, was applied topically to the forearm to determine whether a nonpainful chemical irritation could inhibit the perception of another (weaker) chemical irritation. In the first experiment, sensations of irritation (burning and stinging) produced by a 10% solution of methyl salicylate were significantly attenuated when a 15% solution of the same chemical was applied to the opposite forearm. In the second experiment, neither the perception of warmth nor the heat pain threshold was affected by application of 10% or 15% methyl salicylate to a site 10 cm from the thermal stimulus. Inhibition did, however, occur in the opposite direction: Chemical irritation was reduced after the thermal stimulus reached a painful level. In the third experiment, a 15% solution of methyl salicylate was applied immediately adjacent to the thermal stimulus, with the result that ratings of warmth intensity increased rather than decreased, and perceived irritation was again attenuated following a painful heat stimulus. Overall, the results indicate that (1) chemical counterirritation can occur at nonpainful levels; (2) the resulting inhibition is confined to the nociceptive system; and (3) when the nociceptive and warmth system are activated together, the tendency is toward integration rather than inhibition.

Topics: Adult; Attention; Chemoreceptor Cells; Female; Humans; Male; Neural Inhibition; Nociceptors; Salicylates; Sensory Thresholds; Thermoreceptors; Thermosensing

Plasters containing methyl salicylate with and without l-menthol and dl-camphor were prepared and topically applied on hairless mouse skin to investigate the effects of l-menthol and dl-camphor on the skin penetration and hydrolysis of methyl salicylate in the skin. The in vitro hydrolysis of methyl salicylate was also investigated using the skin homogenate. It was found that l-menthol with dl-camphor enhanced the skin penetration of methyl salicylate, and they inhibited both the in vivo and in vitro hydrolysis of methyl salicylate to salicylic acid.

Topics: Administration, Topical; Animals; Camphor; Chromatography, Gas; Female; Hydrolysis; Menthol; Mice; Mice, Hairless; Salicylates; Skin

Topics: Antineoplastic Agents, Phytogenic; Drugs, Chinese Herbal; Palmitates; Salicylates; Sitosterols

Topics: Administration, Topical; Aerosols; Drug Combinations; Humans; Linseed Oil; Osteoarthritis; Plant Oils; Salicylates; Tea

We have developed a new method for inducing portal hypertension and esophageal varices in rats--partial ligation of the portal vein after devascularization of the circumference of the left renal vein and complete ligation of the portal vein on the fifth day thereafter. Thirty rats were separated into groups of 10, control (sham operation), complete portal ligation only and complete portal ligation plus devascularization. Two weeks after the surgery, the presence of esophageal varices in rats with complete portal ligation plus devascularization was confirmed by portography and by the histological findings. The diameter (mean +/- SD) of the submucosal veins of the lower esophagus in the complete portal ligation plus devascularization group (219.4 +/- 86.6 microns) was significantly larger than that in the complete portal ligation group (99.8 +/- 53.4 microns) or in the control group (30.5 +/- 16.6 microns) (p less than 0.01). Vascular structures of the lower esophagus closely resembled those in humans with esophageal varices. This new technique is simple, rapid and reliable, and application can be made to various experimental studies on portal hypertension.

Topics: Animals; Blood Pressure; Disease Models, Animal; Esophageal and Gastric Varices; Esophagus; Ligation; Male; Mucous Membrane; Portal System; Portal Vein; Portography; Rats; Rats, Inbred Strains; Renal Veins; Salicylates; Veins

Topics: Charcoal; Gastric Emptying; Hiccup; Humans; Male; Middle Aged; Salicylates

This paper studied musk rheumatic oil by GC/FTIR. Ten main components were identified qualitatively, and methyl salicylate, eugenol, cinnamaldehyde were determined by GC internal standard method quantitatively. Average recoveries are within 100 +/- 1.0%, variation coefficients are less than 2.0%.

Topics: Acrolein; Anti-Inflammatory Agents, Non-Steroidal; Chromatography, Gas; Cycloparaffins; Drug Combinations; Eugenol; Materia Medica; Salicylates; Spectrophotometry, Infrared

The adverse effect of topical methylsalicylate ointment on warfarin anticoagulation is studied in 11 patients. All patients had an abnormally elevated international normalized ratio after significant usage of topical methylsalicylate ointment as obvious from both the clinical history and a positive blood level of salicylate. Out of the 11 patients, 3 had bleeding manifestation; 2 with bruises and 1 with gastrointestinal bleeding. It is concluded that topical methylsalicylate ointment should be prescribed with care to patients on warfarin and excessive usage is to be avoided since potentially dangerous drug interaction could occur.

Topics: Administration, Topical; Adult; Aged; Blood Coagulation; Drug Synergism; Female; Gastrointestinal Hemorrhage; Humans; Male; Middle Aged; Ointments; Salicylates; Warfarin

Methyl salicylate, a lipophilic liquid is one of the most commonly used analgesic, counterirritant and rubifacient ingredients in the commercially marketed over-the-counter dermatological products. And, since the effectiveness of the topically applied product depends on the release of the drug from such a dosage form, the present study was proposed to investigate the in vitro release of methyl salicylate from the typical ointment bases and several commercial products. Also, the effects of various additive ingredients on the drug release from these bases were evaluated. In general, the selected ointment bases gave superior in vitro drug release profiles compared to all commercial products included in this study. The addition of ethanol at 10% level in these ointment bases significantly enhanced the drug release from the selected formulations.

Topics: Chemistry, Pharmaceutical; Dermatologic Agents; Ointment Bases; Salicylates; Solubility

Two experiments were performed to examine the perceptual effects of methyl salicylate on hairy skin in humans. In the first experiment, the sensitivity to methyl salicylate (prepared in an ethanol and water vehicle and applied via filter paper) was measured in a paradigm that required subjects to report both the perceived intensity and the perceptual quality of the sensations they experienced. The results indicated that methyl salicylate could be reliably detected at concentrations between 3 and 12%. Peak perceived intensities increased with increasing concentration, and the dominant sensation quality reported was "burning". The second experiment, which measured the effect of methyl salicylate on the perception of temperature change, revealed that the compound enhances the perception of warming but does not affect the perception of cooling. For most subjects, methyl salicylate produced a hyperalgesia to heating. Overall, the data suggest that methyl salicylate probably produces its sensory effects via stimulation and/or sensitization of a population of cutaneous nociceptors.

Topics: Adult; Chemoreceptor Cells; Dose-Response Relationship, Drug; Female; Humans; Male; Nociceptors; Psychophysics; Salicylates; Sensory Thresholds; Skin; Synaptic Transmission; Thermosensing

Topics: Adult; Educational Status; Humans; Male; Plant Oils; Salicylates

1. Rabbit ears were single-pass perfused with a cell-free medium. Arterial pressure, oxygen consumption, and lactate production increased with flow rate. 2. Methyl salicylate was hydrolysed with an apparent Vmax of 1.5 nmol/min per cm2 surface area, a rate about 25 times greater than after arterial administration. 3. Estimation of the Km was not possible, due to oedema developing at arterial concentrations greater than 100 microM methyl salicylate. 4. The model appears suitable to compare absorption, as well as metabolic rates, of xenobiotics in rabbit skin.

Topics: Animals; Ear; Hydrolysis; Kinetics; Perfusion; Rabbits; Salicylates; Skin Absorption

Topics: Drug Synergism; Female; Humans; Middle Aged; Ointments; Osteoarthritis; Salicylates; Warfarin

Experiments were performed on waking rabbits to investigate the changes in both sniffing behavior and local field potential responses in the olfactory bulb during repeated exposure to unreinforced odors. Six rabbits were each implanted with 2 pairs of electrodes for differential recording of the bulbar extracellular field potential. Each animal was given 3 sequential sessions to each of 2 separate odors on 6 consecutive days, while monitoring the bulbar field potential activity and sniffing behavior. Behavioral sniffing responses exhibited rapid within-session decrement in amplitude and long term decrement across sessions. The within-session decrement showed spontaneous recovery between sessions. Both decremental changes in sniffing behavior were accompanied by changes in the bulbar field potential responses. The responses to novel odors were characterized by a reduction in amplitude of high frequency activity (40-80 Hz) and a corresponding increase in amplitude of low frequency activity (15-25 Hz). The high frequency component of the responses showed an initial increase in frequency to a novel odor on the first 3 presentations followed by a rapid decrease in frequency on subsequent trials in the first session which stabilized thereafter. No change in frequency or relative amplitude was observed for the low frequency component. The absolute difference between the odor evoked activity and the preceding control activity measured on each trial showed a significant decrement across sessions with no evidence for spontaneous recovery. The results demonstrate that olfactory bulb responses to novel unreinforced odors show both rapid and long-term changes which parallel changes in sniffing behavior.(ABSTRACT TRUNCATED AT 250 WORDS)

Topics: Action Potentials; Animals; Behavior, Animal; Chemoreceptor Cells; Habituation, Psychophysiologic; Male; Odorants; Olfactory Bulb; Pentanols; Rabbits; Salicylates

Topics: Carbon; Electrochemistry; Electrodes; Salicylates; Thymol

Substances known or suspected to cause subtle or transient anatomical alterations in renal development were administered prenatally or neonatally to rats in order to determine whether they are capable of altering renal functional development. Colchicine alters mitotic activity and cytoskeletal structure and is teratogenic in many species. Since the kidney of the newborn rat undergoes extensive cellular proliferation and nephron differentiation, it is possible that neonatal administration of colchicine may affect nephron development. Dinoseb and methyl salicylate have previously been reported to produce a high incidence of dilated renal pelvis in the term rat fetus. Colchicine was injected sc, at 75 micrograms/kg, to Postnatal Day (PD) 1 Sprague-Dawley rats. Dinoseb was administered ip to pregnant Sprague-Dawley rats on Gestation Days 10-12 at doses of 8 or 10.5 mg/kg/day, and methyl salicylate was administered ip at doses of 200, 250, or 300 mg/kg/day on Gestation Days 11-12. Renal function was examined in pups from immediately after birth through weaning. Maximal urine concentrating ability was measured after DDAVP (desmopressin acetate, a vasopressin analog) injection in suckling rats, and after 24 hr of water deprivation in weanlings. Proximal tubule transport was measured in renal cortical slices. Basal urinary parameters, including urine flow, osmolality, pH, and chloride content, were measured. Colchicine treatment had no effect on body weight or kidney weight. There was a significant decrease in maximal urine osmolality in PD 30 rats measured after 24 hr of water deprivation. The urine concentrating deficit detected in functionally mature PD 30 rats suggests that colchicine treatment during renal histogenesis causes a latent deficit in medullary function in the absence of any gross morphological effects. The 10.5 mg/kg/day dose of dinoseb caused a weight reduction in neonates which persisted after weaning. Urine volume after DDAVP challenge was increased over controls in both dose groups on PD 6, but maximal urine concentration was unaffected. On PD 14, maximal urine concentration after DDAVP injection was decreased in the 10.5 mg/kg/day group. By PD 30, urine concentrating ability was comparable to controls. Renal cortical slices from the 10.5 mg/kg/day dose group had an enhanced ability to accumulate organic anions on PD 3 and 31, but opposite effects were observed in the low-dose group. No other renal functional parameters were altered. Urine os

Topics: 2,4-Dinitrophenol; Animals; Animals, Suckling; Colchicine; Deamino Arginine Vasopressin; Dinitrophenols; Female; Fetus; Herbicides; Kidney Cortex; Kidney Diseases; Kidney Function Tests; Pregnancy; Prenatal Exposure Delayed Effects; Rats; Rats, Inbred Strains; Salicylates; Teratogens

Unilateral inspiratory and expiratory nasal resistance to airflow were measured in 35 subjects using active anterior rhinomanometry. No significant difference was found between inspiratory and expiratory resistance. Inhalation of a mixture of aromatics, camphor, menthol, oil of pine needles and methyl salicylate had no effect on inspiratory or expiratory nasal resistance. Factors influencing inspiratory and expiratory resistance and the actions of aromatics are discussed.

Topics: Adult; Airway Resistance; Camphor; Female; Humans; Male; Menthol; Nasal Decongestants; Nasal Mucosa; Pulmonary Ventilation; Respiration; Salicylates; Terpenes

Excessive percutaneous absorption of potentially toxic substances such as menthol and methyl salicylate may occur through local application of heat, such as the use of a heating pad. Menthol and methyl salicylate are found in nonprescription items and used for muscular and arthritic pains. This patient experienced full-thickness skin and muscle necrosis as well as persistent interstitial nephritis as a result of topical application of methyl salicylate and menthol followed by use of a heating pad, despite the manufacturer's warning against the use of heating pads.

Topics: Administration, Cutaneous; Drug Combinations; Hot Temperature; Humans; Male; Menthol; Middle Aged; Muscular Diseases; Necrosis; Nephritis, Interstitial; Salicylates; Skin Diseases, Vesiculobullous

Plasma and urinary levels of salicylic acid were examined in Standardbred mares after administration of various feeds, containing different compositions of hay. In addition, horses were administered acetylsalicylic acid orally and methyl salicylate topically. Elevated salicylic acid levels were observed in horse urine and plasma in animals fed lucerne hay. The plasma and urinary elimination of salicylic acid exhibited a diurnal pattern which was related to the type of feed and the feeding schedule. Within 24 h after oral administration of acetylsalicylic acid, plasma and urine salicylic acid levels were consistent with residual levels observed after feeding lucerne hay. Elimination of salicylic acid was rapid and complete, with a half-life between 5 and 7 h. Topical administration of methyl salicylate (8.4 g) produced elevated urinary salicylic acid levels for 6 h. A smaller dose of methyl salicylate (3.4 g) did not elevate plasma or urine salicylic acid levels above those observed following administration of lucerne hay.

Topics: Administration, Oral; Administration, Topical; Animal Feed; Animals; Aspirin; Chromatography, High Pressure Liquid; Female; Gas Chromatography-Mass Spectrometry; Horses; Hydrogen-Ion Concentration; Salicylates

The time course, dose response, components of inflammation, and involvement of putative mediators of inflammation in irritation induced by different chemicals was compared using a mouse ear swelling technique. Differences in time courses of inflammation produced by the irritants were not solely due to differences in rates of penetration. Changes in blood flow and permeability of vessels were phasic with different numbers of phases induced by different irritants. Effects of antagonist, synthesis, inhibitors, and depleting agents of putative inflammatory mediators on intensity of inflammation varied for different irritants. These studies demonstrate that all chemicals do not produce skin irritation by a common inflammatory pathway.

Topics: Alkynes; Animals; Animals, Laboratory; Capillary Permeability; Croton Oil; Dermatitis; Dose-Response Relationship, Drug; Female; Mice; Mice, Inbred ICR; Regional Blood Flow; Salicylates; Skin; Skin Absorption

Fifty percent of an Amblyomma variegatum female population were able to find upwind-positioned targets containing the synthetic aggregation-attachment pheromone of this species or the pheromone component o-nitrophenol alone. The ticks were not attracted to the other components of the pheromone: methyl-salicylate and pelargonic acid. The mean time required for the ticks to reach a target at 1 m from the starting point was 3 min and 20 s.

Topics: Animals; Fatty Acids; Female; Nitrophenols; Pheromones; Salicylates; Ticks

Topics: Microscopy; Oils; Salicylates

Two closely related species of mycobacteria, Mycobacterium vaccae and M. neoaurum, were grown under conditions of iron-deficiency (0.02-0.05 microgram Fe ml-1) and iron-sufficiency (2-4 micrograms Fe ml-1) in a simple glycerol/asparagine medium. The strain of M. vaccae used was a nonmycobactin producer whereas M. neoaurum synthesized between 6-8% of its cell biomass as the lipid-soluble siderophore when grown under iron-limitation. The role of mycobactin for iron-acquisition was examined using both pure and mixed cultures, with cell viability determined following growth at various iron concentrations. M. neoaurum, the mycobactin producer, outgrew M. vaccae when iron was readily available. When grown under conditions where iron was limiting, M. neoaurum showed a decline in viable cell number compared with its competitor, highlighting its increased requirement for the metal. Some recovery was observed following mycobactin biosynthesis, this being greatly enhanced by the addition of an iron supplement to the growing cells. Mycobactin biosynthesis allowed M. neoaurum to rapidly acquire any additional iron presented to the bacteria when growing under iron-limitation. However, M. vaccae did not synthesize the lipid-soluble siderophore with its iron-requirement satisfied by production of extracellular exochelin.

Topics: Iron; Mycobacterium; Oxazoles; Salicylates

Methylsalicylate-grown cells of Pseudomonas sp. WR401 cometabolized 3-, 4- and 5-substituted halosalicylates to the corresponding halocatechols. Further degradation was unproductive due to the presence of high levels of catechol 2,3-dioxygenase. This strain acquired the ability to utilize 3-chlorobenzoate following acquisition of genes from Pseudomonas sp. B13 which are necessary for the assimilation of chlorocatechols. This derivative (WR4011) was unable to use 4- or 5-chlorosalicylates. Derivatives able to use these compounds were obtained by plating WR4011 on 5-chlorosalicylate minimal medium; one such derivative was designated WR4016. The acquisition of this property was accompanied by concomitant loss of the methylsalicylate phenotype. During growth on 4- or 5-chlorosalicylate the typical enzymes of chlorocatechol assimilation were detected in cell free extracts, whereas catechol 2,3-dioxygenase activity was not induced. Repeated subcultivation of WR4016 in the presence of 3-chlorosalicylate produced variants (WR4016-1) which grew on all three isomers.

Topics: Biodegradation, Environmental; Catechol 2,3-Dioxygenase; Catechols; Chlorine; Chlorobenzoates; Conjugation, Genetic; Dioxygenases; Genes, Bacterial; Genetic Code; Oxygen Consumption; Oxygenases; Phenotype; Pseudomonas; Salicylates; Substrate Specificity

The effects of exercise, heat exposure or both on the percutaneous absorption of methyl salicylate were studied in 6 healthy volunteers. Exercise was performed to 30% of VO2max, 45 min each hour for 6 h, at ambient temperatures of 22 degrees C or 40 degrees C. Systemic availability was assessed by measurement of plasma salicylate concentrations and cumulative urinary salicyluric acid excretion over an 8-h collection period. The absorption of methyl salicylate was increased to more than 3-times above control in subjects exercising in the heat. It is concluded that exercise and heat exposure, by increasing skin temperature, hydration and blood flow, enhance the percutaneous absorption of methyl salicylate.

Topics: Adult; Biological Availability; Hippurates; Hot Temperature; Humans; Kinetics; Male; Oxygen Consumption; Physical Exertion; Salicylates; Skin Absorption

Human platelets pre-exposed to arachidonic acid (AA) (0.1-1 mM) or to the endoperoxide analogue U46619 (1-3 microM) and then washed and resuspended, failed to respond with aggregation or secretion to a second challenge by either agonist. The response to thrombin at low (0.04-0.1 u ml-1) but not at high (2.5 u ml-1) concentrations was also inhibited by pre-exposure to AA and U46619. The ability of platelets to synthesize thromboxane (Tx) B2 from AA or upon challenge with thrombin persisted despite platelet desensitization. In the presence of the reversible cyclo-oxygenase (CO) inhibitors methyl salicylate (MS) or L8027, pre-exposure to AA had no effect on subsequent challenge by the same agonist or by U46619, whereas platelet desensitization by pre-exposure to U46619 persisted. However, platelet activation by, and desensitization to AA and U46619, was prevented by trimetoquinol and compound L636499, two thromboxane/endoperoxide receptor antagonists. In contrast to the CO inhibitors, the thromboxane synthetase inhibitor dazoxiben, which in 3 'responders' out of 5 subjects suppressed aggregation, secretion, and Tx formation induced by AA, failed to prevent AA-induced desensitization. Compared to quiescent cells the distances between platelets desensitized after re-exposure to AA were reduced in electron microscopy, but the tight connections associated with aggregated cells were not observed. Degranulation was also not observed and cell morphology resembled that of normal quiescent platelets. In conclusion, (a) AA and U46619 desensitize human platelets at a similar site sensitive to prostaglandin/thromboxane receptor antagonists, and show cross-desensitization; (b) desensitization by AA appears to be mediated by a CO-dependent metabolite, as CO inhibitors prevent desensitization by AA but not to U46619; (c) the failure of dazoxiben to prevent desensitization by AA suggests that a metabolite other than TxA2, possibly the endoperoxides, mediates the phenomenon; (d) desensitization does not involve inactivation of CO or thromboxane synthetase enzymes.

Topics: Adenosine Triphosphate; Arachidonic Acid; Arachidonic Acids; Blood Platelets; Cyclooxygenase Inhibitors; Humans; Imidazoles; Indoles; Microscopy, Electron; Platelet Aggregation; Prostaglandin Endoperoxides, Synthetic; Receptors, Cell Surface; Receptors, Prostaglandin; Receptors, Thromboxane; Salicylates; Thrombin; Thromboxane B2

Methyl salicylate (oil of wintergreen) in the form of candy flavoring was ingested by a 21-month-old male infant who subsequently developed vomiting, lethargy, and hyperpnea. A "swallow" of the solution resulted in a serum salicylate concentration of 81 mg/dL six hours after ingestion. The infant was treated with parenteral fluids and sodium bicarbonate and he recovered rapidly. Hazards associated with salicylate use in this form include lack of parental awareness of the substance's toxic potential, the attractiveness of the candy-like odor, and the availability of the liquid in non-child-resistant packaging containing potentially lethal quantities.

Topics: Candy; Flavoring Agents; Humans; Infant; Male; Respiration Disorders; Salicylates; Sleep Stages; Vomiting

The possibility that chemicals induce skin irritation by multiple mechanisms was studied in laboratory mice. The time course and dose response to topical application of phenol, croton oil, benzalkonium chloride, ethyl phenylpropiolate (EPP), and methyl salicylate were compared. The responses to each chemical were measured as changes in ear thickness following application to one ear. Maximal responses were as follows: methyl salicylate 20 min, phenol 1 hr, croton oil and benzalkonium chloride 6 hr, and EPP 8 hr. The response to EPP included an early, smaller response at 1 hr. Time courses of the responses were not altered by changing the vehicle in which the irritants were applied or by altering the dose. The rates of regression of the inflammatory responses also varied. Although visibly normal, thickness of ears treated with either phenol or benzalkonium chloride remained 0.05 to 1 mm thicker than solvent-treated control ears for 6 weeks. Although the incidence of prolonged thickness was dose related, it was not determined by the intensity of the acute response; doses of other irritants which produced equivalent acute increases in ear thickness did not produce similar changes. The components of the acute responses, i.e., vascular permeability, change in blood flow, and cellular infiltration, to 5 mg methyl salicylate, 2 mg EPP, and 0.05 mg croton oil were compared in studies of tissue histology, changes in vascular permeability by trypan blue and 125I-labeled bovine serum albumin, and change in local surface temperature as an index of blood flow. The histology of the reactions at the time of maximum response to the chemicals differed. Multiple periods of increased permeability and increased surface temperature were produced by the irritants. The permeability and blood flow responses produced by the irritants varied in number, time of occurrence relative to time of application and to time of maximum response, and in magnitude of the changes. Differences in time courses of the responses which were not altered by experimentally varying rate of absorption and in components of the inflammatory response to the three irritants suggest that chemicals induce skin irritation by multiple mechanisms.

Topics: Absorption; Alkynes; Animals; Croton Oil; Dermatitis, Contact; Ear; Female; Irritants; Mice; Mice, Inbred ICR; Salicylates; Time Factors

Nondissected ovaries of tuber-bearing Solanum sp. were stained with Mayer's hemalum, a positive stain for chromatin and nucleoli, and then optically cleared with methyl salicylate, a clearing agent. Clarity, resolution and contrast within the ovules dissected from ovaries were comparable to those of sectioned, paraffin embedded ovaries. Contrast within ovules greatly exceeded that of unstained and nonspecifically stained clearings, and eliminated the need of special optics, i.e., Nomarski interference-contrast optics, for optimal viewing and photography. Much less time and labor were required than for embedded specimens. Usefulness of the technique for cytogenetic and cytological research was verified by analyzing meiosis and other features of megasporogenesis and megagametogenesis in normal, and in two meiotic mutants, of Solanum. The results illustrate the usefulness of combined Mayer's hemalum staining and methyl salicylate clearing, and suggest additional stain-clearing agent combinations have potential for cytological and cytogenetic research. Preliminary results with other species suggest the technique may also be useful for classroom instruction.

Topics: Alum Compounds; Aluminum; Benzopyrans; Hematoxylin; Plant Cells; Salicylates; Staining and Labeling

Topics: Aspirin; Humans; Molecular Weight; Salicylates; Therapeutic Equivalency

Topics: Adult; Drug Combinations; Humans; Iodine; Iontophoresis; Male; Ointments; Oleic Acid; Oleic Acids; Salicylates; Tendon Injuries; Tissue Adhesions

A topically applied rubifacient delivered by aerosol (Deep-Heat) was studied. After spray application to the forearms of volunteers, without massage, the erythema produced was measured by thermography and correlated with the concentration of 2 salicylate components of the mixture found in local and systemic venous blood. Maximum erythema occurred at about 30 minutes, while blood salicylate levels were maximal between 20 and 30 minutes after application. Methyl salicylate was absorbed before ethyl salicylate. Over the time period of the erythematous response oxygen levels in local venous blood were raised. Finally, platelets collected from venous blood draining from the sprayed site, when induced to clump by the addition of arachidonic acid in an aggregometer, showed increased resistance to clumping when compared with control cells. The mechanism of these observed phenomena and the mode of action of the constituents of Deep-Heat are discussed.

Topics: Administration, Topical; Adult; Aerosols; Female; Forearm; Humans; Irritants; Male; Niacin; Oxygen; Platelet Aggregation; Salicylates; Skin Temperature; Thermography

Methyl salicylate was administered topically to pregnant hamsters at 7d9h and the teratogenic results were compared with those obtained following oral treatment with the same compound. Both treatments produced the same defect in embryos recovered at day 9: failure of fusion of the neural tube, especially in the area of the developing brain. Analysis of serum salicylate levels following both treatments produced similar curves and indicated that teratogenic levels of salicylate can reach the maternal circulation after topical exposure.

Topics: Administration, Oral; Administration, Topical; Animals; Cricetinae; Female; Maternal-Fetal Exchange; Neural Tube Defects; Pregnancy; Salicylates

Topics: Abnormalities, Drug-Induced; Animals; Behavior; Caffeine; Female; Food Additives; Food Supply; Humans; Nervous System; Pregnancy; Rats; Salicylates; United States; United States Food and Drug Administration

A novel technique to prepare isolated transparent natural blood vessels was developed and used to study the detailed flow patterns in some regions of the circulation. It was found that paired spiral secondary flows and recirculation zones form downstream of venous valves, at the arterial T-junctions in the dog abdominal aorta, and in the human carotid sinus over a wide range of geometrical and flow conditions, including the time-averaged mean values of the physiological flow rates.

Topics: Animals; Aorta, Abdominal; Blood Physiological Phenomena; Blood Vessels; Carotid Arteries; Dogs; Humans; Regional Blood Flow; Rheology; Salicylates; Saphenous Vein; Specimen Handling

Topics: Administration, Topical; Biological Availability; Humans; Ointments; Permeability; Salicylates; Salicylic Acid; Skin Absorption

The haemolytic effect of methylsalicylate (MS) on human and sheep erythrocytes is reported for the first time to our knowledge. Human erythrocytes are more sensitive to this effect. Haemolysis is proportional to the concentration of methylsalicylate and the duration of incubation. Lowering of surface tension and the ensuing membrane damage appear to be the mechanism by which the haemolytic effect is produced.

Topics: Erythrocyte Membrane; Erythrocytes; Hemolysis; Humans; In Vitro Techniques; Membrane Lipids; Phospholipids; Salicylates; Sterols; Surface Tension

Topics: Acetazolamide; Adult; Animals; Erythrocyte Membrane; Erythrocytes; Hemolysis; Histamine; Humans; In Vitro Techniques; Male; Procaine; Salicylates; Sheep; Tetracycline; Urethane

Tetramethyl benzidine (TMB) as a substrate for horseradish peroxidase (HRP) histochemistry offers a great advantage over other substrates in its sensitivity but the reaction product is unstable in alcohol. Immersing TMB-reacted sections in methyl salicylate renders the reaction product stable enough so that exposure to ethanol for 10 min causes no detectable loss of HRP labelled neurons. A rapid thionin stain is introduced which, after stabilizing the TMB-based reaction product in methyl salicylate, causes no detectable loss of HRP labelled neurons. These procedures should prove valuable to users of the popular HRP techniques for studying neural connections.

Topics: Benzidines; Brain Mapping; Chemical Phenomena; Chemistry; Coloring Agents; Ethanol; Histocytochemistry; Horseradish Peroxidase; Microtomy; Peroxidases; Phenothiazines; Salicylates

Topics: Animals; Chick Embryo; Coronary Vessels; Embryo, Mammalian; Fixatives; Microscopy; Photography; Rats; Salicylates

Topics: Chemistry, Pharmaceutical; Chromatography; Liniments; Ointments; Pharmacy; Research; Salicylates

Topics: Humans; Salicylates

Topics: Bone and Bones; Dogs; Growth; Pathology; Rabbits; Rats; Research; Salicylates; Toxicology

Topics: Humans; Salicylates

Topics: Blood Transfusion; Child; Exchange Transfusion, Whole Blood; Gaultheria; Humans; Infant; Oils, Volatile; Plant Extracts; Salicylates

Topics: Edema; Pulmonary Edema; Salicylates

Topics: Humans; Salicylates

Topics: Humans; Salicylates

Topics: Bandages; Humans; Poliomyelitis; Salicylates

Topics: Alkalosis; Child; Death; Humans; Salicylates

Topics: Blood Transfusion; Exchange Transfusion, Whole Blood; Humans; Salicylates

Topics: Arthritis; Arthritis, Rheumatoid; Humans; Osteoarthritis; Rheumatic Diseases; Salicylates

Topics: Humans; Poisoning; Salicylates

Topics: Blood Transfusion; Child; Exchange Transfusion, Whole Blood; Flavoring Agents; Humans; Infant; Oils, Volatile; Plant Extracts; Poisoning; Salicylates

Topics: Humans; Poisoning; Salicylates

Topics: Esters; Humans; Niacin; Nicotinic Acids; Salicylates

Topics: Humans; Salicylates

Topics: Alkaloids; Edema; Epinephrine; Pulmonary Edema; Salicylates; Thiourea

Topics: Salicylates

Topics: Humans; Salicylates

Topics: Analgesics; Humans; Pharmaceutical Preparations; Salicylates

Topics: Salicylates

Topics: Biological Assay; Humans; Ointments; Salicylates

Topics: Salicylates

Topics: Humans; Salicylates

Topics: Emulsions; Salicylates

Topics: Humans; Salicylates