iridoids and acteoside

SA and H

Topics: Antioxidants; Hydrogen Peroxide; Iridoids; Orobanchaceae; Phenols; Salicylic Acid

In this study, an overall survey regarding the determination of several bioactive compounds in olive fruit is presented. Two methodologies were developed, one UPLC-Q-TOF-MS method for the determination of olive fruit phenolic compounds and one HPLC-DAD methodology targeting the determination of pigments (chlorophylls and carotenoids), tocopherols (α-, β, -γ, δ-) and squalene. Target and suspect screening workflows were developed for the thorough fingerprinting of the phenolic fraction of olives. Both methods were validated, presenting excellent performance characteristics, and can be used as reliable tools for the monitoring of bioactive compounds in olive fruit samples. The developed methodologies were utilized to chemical characterize the fruits of the

Topics: Aldehydes; Chromatography, High Pressure Liquid; Fruit; Glucosides; Greece; Iridoids; Olea; Olive Oil; Phenols; Phenylethyl Alcohol; Phytochemicals; Tandem Mass Spectrometry; Tocopherols

The mesothelial cells (MCs) play an important role in the morpho-functional alterations of the peritoneal membrane (PM) undergoing peritoneal dialysis (PD). MCs, through the epithelial-mesenchymal transition process (EMT), progressively acquire a myofibroblast-like phenotype, promoting peritoneal fibrosis (PF) and failure of peritoneal membrane function. Transforming growth factor β1 (TGFβ1), through canonical and non-canonical pathways, promotes the epithelial-mesenchymal transition (EMT) process leading to PF. To investigate the therapeutic potential of an olive leaf extract (OLE) on preserving peritoneal membrane function, we evaluated the effect of OLE on the TGFβ1-induced EMT in mesothelial cells, Met5A, and elucidated the underlying molecular mechanisms. As assessed by changes in the expression of epithelial, mesenchymal, and fibrotic cell markers (such as E-cadherin, N-cadherin, α-SMA, fibronectin, vimentin), levels of matrix metalloproteinases (MMP2 and MMP9), and cell migration, OLE inhibited the TGFβ1-induced EMT. Importantly, the beneficial effect of OLE was mediated by reduction of the TGFβ1-induced activation of Smad2/3 signaling and the mitigation of extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), and p38 mitogen-activated protein kinase (MAPK) phosphorylation. Smad/non-Smad signaling pathways, activated by TGFβ1, both reduce expression of epithelial marker E-cadherin which has a crucial role in EMT initiation. Interestingly, we observed that in presence of OLE activity of the E-cadherin, promoter was increased and concomitantly OLE reduced the nuclear content of its co-repressor SNAIL. Our results suggest the potential therapeutic of OLE to counteract fibrotic process in peritoneal dialysis patients.

Topics: Antigens, Differentiation; Cadherins; Cell Line; Cell Membrane; Epithelial-Mesenchymal Transition; Glucosides; Humans; Iridoid Glucosides; Iridoids; Olea; Peritoneal Dialysis; Phenols; Phenylethyl Alcohol; Plant Extracts; Signal Transduction; Smad Proteins, Receptor-Regulated; Transforming Growth Factor beta1

Polyphenols are constituents of all higher plants. However, their biosynthesis is often induced when plants are exposed to abiotic stresses, such as drought. The aim of the present work was to determine the phenolic status in the roots of olive trees grown under water deficit conditions. The results revealed that roots of water-stressed plants had a higher content of total phenols. The main compound detected in well-watered olive tree roots was verbascoside. Oleuropein was established as the predominant phenolic compound of water-stressed plants. The oleuropein/verbascoside ratio varied between 0.31 and 6.02 in well-watered and water-stressed plants respectively, which could be a useful indicator of drought tolerance in olive trees. Furthermore, this study is the first to provide experimental evidence showing that luteolin-7-rutinoside, luteolin-7-glucoside and apigenin-7-glucoside were the dominant flavonoid glucosides in olive tree roots and showed the most significant variations under water stress.

Topics: Antioxidants; Apigenin; Droughts; Flavonoids; Glucosides; Iridoid Glucosides; Iridoids; Olea; Phenol; Phenols; Phenylethyl Alcohol; Plant Extracts; Plant Leaves; Plant Roots; Polyphenols; Spectrophotometry, Ultraviolet; Stress, Physiological; Water

Duranta erecta L.is a valuable herb used in traditional system of medicine in India and China for the treatment of malaria and abscesses. The presence of phenylethanoid (e.g., acteoside as major bioactive) in addition to iridoid and flavonoids glycosides are mainly responsible for reported pharmacological properties. Although D. erecta is widely used in many Asian countries, the quality assurance of raw herb and its derived products are still in question, due to the lack of validated protocol. Current Indian guidelines for quality assurance of phytopharmaceutical product demands accurate determination of minimum four chemicals. Moreover, there is no chromatographic method to simultaneously analyse acteoside, isoacteoside, durantoside I, quercetin, and methylapigenin-7-O-β-D-glucopyranuronate in D. erecta. The present study establishes a systematic approach for the quality evaluation of D. erecta with efficient and validated UPLC-PDA method that simultaneously analyses the five bioactive marker chemicals in D. erecta. A fast, sensitive, and reliable ultraperformance liquid chromatography-photodiode array (UPLC-PDA) method was developed for the quantification five marker compounds-acteoside, isoacteoside, durantoside-I, quercetin, and methylapigenin-7-O-β-D-glucopyranuronate in D. erecta. The optimized UPLC conditions on Reverse phase column Phenomenex Luna® (C

Topics: Calibration; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavonols; Glucosides; Glycosides; India; Iridoids; Limit of Detection; Linear Models; Phenols; Phenylethyl Alcohol; Plant Extracts; Reproducibility of Results; Uncertainty

Cornus officinalis-Rehmannia glutinosa herb couple is widely used herb medicine in clinical practice to treat chronic kidney disease (CKD). However, the in vivo integrated metabolism of its main bioactive components in CKD rats remains unknown. In this study, UPLC-Q-TOF/MS technique combined with Metabolynx

Topics: Administration, Oral; Animals; Case-Control Studies; Chromatography, High Pressure Liquid; Cornus; Feces; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Male; Phenols; Plant Extracts; Rats; Rehmannia; Renal Insufficiency, Chronic; Tandem Mass Spectrometry

Chronic hyperalgesia and allodynia associated with progressive damage of peripheral neurons are the most prevalent complications of diabetes mellitus. Plants belonging to the family of Oleaceae were traditionally used in folk medicine for the management of diabetes.. The aim of this study was to investigate whether an aqueous extract from the leaves of Ligustrum vulgare (common privet) could be useful to target neuropathic pain in a rat streptozotocin (STZ) model of diabetes.. The chemical composition of the aqueous extract from privet leaf was characterized with the UHPLC-DAD-MS method and the analytical quantification of its constituents was performed with HPLC-DAD. Mechanical hyperalgesia and allodynia were evaluated with the Randall-Selitto and von Frey tests.. Our investigation revealed the presence of secoiridoids: oleacein (23.48 ± 0.87 mg/g), oleocanthal (8.44 ± 0.08 mg/g), oleuropein (1.50 ± 0.01 mg/g), as well as phenylpropanoids: echinacoside (6.46 ± 0.07 mg/g), verbascoside (4.03 ± 0.04 mg/g) and p-coumaroyl glucarates in the dried aqueous extract of privet leaves. Behavioral data indicated that chronic intraperitoneal administration of the extract (50-200 mg/kg) for 21 days resulted in a decrease in diabetes-induced hyperalgesia and allodynia. Blood glucose levels remained unaltered, while body weight and water intake decreased significantly.. The aqueous privet leaf extract could serve useful in facilitating treatment of painful diabetic neuropathy. Additionally, the study showed that the antihyperalgesic activity of Ligustrum vulgare leaf extract is not likely related to its antihyperglycemic properties.

Topics: Aldehydes; Animals; Chromatography, High Pressure Liquid; Cyclopentane Monoterpenes; Diabetes Mellitus, Experimental; Diabetic Neuropathies; Glucosides; Glycosides; Hyperalgesia; Iridoid Glucosides; Iridoids; Ligustrum; Male; Neuralgia; Phenols; Plant Extracts; Plant Leaves; Rats; Streptozocin

We report the first analysis in absolute, and in particular, concerning the phytochemical pattern, about an endemic Italian species, Ajuga tenorei C. Presl. The analysis, performed by means of techniques such as Column Chromatography and NMR spectroscopy and Mass spectrometry, led to the isolation and the identification of five compounds namely verbascoside (1), echinacoside (2), ajugoside (3), harpagide (4) and 8-O-acetylharpagide (5). The presence of these compounds is important from both chemotaxonomic and ethno-pharmacological point of view. For what concerns the first point is confirmed the correct botanical classification of the species. The isolated compounds are also known to exert peculiar pharmacological activities and their presence may give a rationale to the historical medicinal properties associated to the Ajuga genus in general, since these plants have a long traditional use in many parts of the world. Such fact might suggest the use of also this species in this sense.

Topics: Ajuga; Glucosides; Glycosides; Iridoid Glycosides; Iridoids; Italy; Mass Spectrometry; Phenols; Plant Components, Aerial; Plant Extracts; Plants, Medicinal; Pyrans

In this study, we report the first phytochemical analysis of polar fraction of Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Several iridoid glucosides were isolated, namely aucubin (1), monomelittoside (2), plantarenaloside (3), euphroside (4), mussaenosidic acid (5) and 8-epiloganic acid (6), showing a composition in accordance with previous study on this genus. The studied samples, collected from Dolomites, presented a chemotype already recognised in species from North America, characterised by euphroside (4) and aucubin (1) as main components, but the main character was the presence of monomelittoside (2) never reported in this genus. The identification of verbascoside (7), leucosceptoside A (9) and echinacoside (10) complete the systematic framing of this species since is ascertained the co-occurrence of phenylethanoid glycosides with iridoids in Lamiales species.

Topics: Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Italy; Molecular Structure; Pedicularis; Phenols; Plant Extracts

A sensitive and rapid method for determination of loganin, morroniside, catalpol and acteoside in rat plasma after oral administration of Rehmannia glutinosa Libosch and Cornus officinalis Sieb drug pair based on ultra-high performance liquid chromatography coupled with tandem mass spectrometry (UPLC-MS). Chromatographic separation was achieved using an Acquity UPLC BEH C18 column (100mm×2.1mm, 1.7μm) at a flow rate of 0.4mL/min, using gradient mode containing 0.1% formic acid in water and acetonitrile were used as the mobile phase A and B. Loganin, morroniside, catalpol, acteoside and the internal standard (chloramphenicol) were detected by selected reaction monitoring in the negative ion mode with the mass transition of m/z 451.0→179.0 (morroniside), m/z 435.0→227.0 (loganin), m/z 407.1→199.1 (catalpol), m/z 623.2→161.0 (acteoside) and m/z 320.8→151.9 (chloramphenicol), respectively. All calibration curves showed good linearity (r>0.991). The precision was evaluated by intra-day and inter-day assays and the RSD% were all within 9.58%. The recovery ranged from 67.62 to 80.14%. The method was successfully applied to pharmacokinetic study of the analytes in normal and doxorubicin-induced chronic kidney disease rat plasma.

Topics: Administration, Oral; Animals; Chromatography, High Pressure Liquid; Cornus; Drugs, Chinese Herbal; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Limit of Detection; Male; Mass Spectrometry; Phenols; Rats; Rats, Sprague-Dawley; Rehmannia; Renal Insufficiency, Chronic

The antimicrobial properties of olive leaf extract (OLE) have been well recognized in the Mediterranean traditional medicine. Few studies have investigated the antimicrobial properties of OLE. In this preliminary study, commercial OLE and its major phenolic secondary metabolites were evaluated in vitro for their antimicrobial activities against Escherichia coli and Staphylococcus aureus, both individually and in combination with ampicillin. Besides luteolin 7-O-glucoside, OLE and its major phenolic secondary metabolites were effective against both bacteria, with more activity on S. aureus. In combination with ampicillin, OLE, caffeic acid, verbascoside and oleuropein showed additive effects. Synergistic interaction was observed between ampicillin and hydroxytyrosol. The phenolic composition of OLE and the stability of olive phenols in assay medium were also investigated. While OLE and its phenolic secondary metabolites may not be potent enough as stand-alone antimicrobials, their abilities to boost the activity of co-administered antibiotics constitute an imperative future research area.

Topics: Ampicillin; Anti-Bacterial Agents; Bacteria; Caffeic Acids; Drug Synergism; Escherichia coli; Flavones; Glucosides; Herb-Drug Interactions; Iridoid Glucosides; Iridoids; Medicine, Traditional; Olea; Phenols; Phenylethyl Alcohol; Plant Extracts; Plant Leaves; Staphylococcus aureus

In our continued investigation of plants from the family Oleaceae we have now investigated Picconia azorica endemic to the Azores. Like most species within the family it contains the oleoside-based secoiridoid glucosides ligstroside and oleuropein as the main compounds and in addition verbascoside and echinacoside. As with the previously investigated Picconia excelsa, it also contained the carbocyclic iridoid glucosides involved in the biosynthetic pathway to the oleoside derivatives. However, while P. excelsa contained loganin esterified with some monoterpenoid acids, P. azorica contains similar esters of 7-epi-loganic acid named Picconioside A and B. In addition were found the two 7-O-E/Z-cinnamoyl esters of 7-epi-loganic acid named Picconioside C and D.

Topics: Azores; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Molecular Structure; Oleaceae; Phenols; Pyrans

Several naturally occurring dietary polyphenols with chemopreventive or anticancer properties are topoisomerase II poisons. To identify additional phytochemicals that enhance topoisomerase II-mediated DNA cleavage, a library of 341 Mediterranean plant extracts was screened for activity against human topoisomerase IIα. An extract from Phillyrea latifolia L., a member of the olive tree family, displayed high activity against the human enzyme. On the basis of previous metabolomics studies, we identified several polyphenols (hydroxytyrosol, oleuropein, verbascoside, tyrosol, and caffeic acid) as potential candidates for topoisomerase II poisons. Of these, hydroxytyrosol, oleuropein, and verbascoside enhanced topoisomerase II-mediated DNA cleavage. The potency of these olive metabolites increased 10-100-fold in the presence of an oxidant. Hydroxytyrosol, oleuropein, and verbascoside displayed hallmark characteristics of covalent topoisomerase II poisons. (1) The activity of the metabolites was abrogated by a reducing agent. (2) Compounds inhibited topoisomerase II activity when they were incubated with the enzyme prior to the addition of DNA. (3) Compounds were unable to poison a topoisomerase IIα construct that lacked the N-terminal domain. Because hydroxytyrosol, oleuropein, and verbascoside are broadly distributed across the olive family, extracts from the leaves, bark, and fruit of 11 olive tree species were tested for activity against human topoisomerase IIα. Several of the extracts enhanced enzyme-mediated DNA cleavage. Finally, a commercial olive leaf supplement and extra virgin olive oils pressed from a variety of Olea europea subspecies enhanced DNA cleavage mediated by topoisomerase IIα. Thus, olive metabolites appear to act as topoisomerase II poisons in complex formulations intended for human dietary consumption.

Topics: DNA Cleavage; DNA Topoisomerases, Type II; Drug Screening Assays, Antitumor; Fruit; Glucosides; Humans; Iridoid Glucosides; Iridoids; Olea; Phenols; Phenylethyl Alcohol; Plant Bark; Plant Extracts; Plant Leaves; Plasmids; Topoisomerase II Inhibitors

Olive leaves are rich in bioactive compounds, which are beneficial for humans. The objective of this work was to assess the influence of processing conditions (drying and extraction) of olive leaves on the extract's bioaccessibility. Thus, extracts obtained from dried olive leaves (hot air drying at 70 and 120 °C or freeze-drying) by means of conventional or ultrasound-assisted extraction were subjected to in vitro digestion. Antioxidant capacity, total phenolic content, and HPLC-DAD/MS/MS analysis were carried out during digestion. The dehydration treatment used for the olive leaves did not have a meaningful influence on bioaccessibility. The digestion process significantly (p<0.05) affected the composition of the extracts. Oleuropein and verbascoside were quite resistant to gastric digestion but were largely degraded in the intestinal phase. Nevertheless, luteolin-7-O-glucoside was the most stable polyphenol during the in vitro simulation (43% bioaccessibility). Therefore, this compound may be taken into consideration in further studies that focus on the bioactivity of olive leaf extracts.

Topics: Agriculture; Antioxidants; Dietary Supplements; Digestion; Food Handling; Glucosides; Humans; Hydrolysis; Industrial Waste; Iridoid Glucosides; Iridoids; Luteolin; Models, Biological; Olea; Phenols; Phytochemicals; Plant Extracts; Plant Leaves; Spain

Castilleja tenuiflora (Orobanchaceae) has been used in Mexican traditional medicine as a treatment for cough, dysentery, anxiety, nausea and vomiting as well as hepatic and gastrointestinal diseases. The ethanolic extract of the aerial parts of Castilleja tenuiflora was separated by silica gel column chromatography. The fractions were evaluated using the induced edema acetate 12-O-tetradecanoylphorbol (TPA) anti-inflammatory activity model. The most active fraction was subjected to medium-pressure liquid chromatography (MPLC) with UV detection at 206 and 240 nm. The following iridoids were isolated: geniposidic acid, aucubin, bartioside, 8-epi-loganin, mussaenoside, and the phenylpropanoid verbascoside. The most active iridoid was geniposidic acid, which was more active than the control (indomethacin), and the least active iridoid was mussaenoside. 8-epi-Loganin, and mussaenoside have not been previously reported to be anti-inflammatory compounds. The results of these investigations confirm the potential of Mexican plants for the production of bioactive compounds and validate the ethnomedical use of Castilleja tenuiflora-like anti-inflammatory plants.

Topics: Acanthaceae; Animals; Anti-Inflammatory Agents; Edema; Glucosides; Inhibitory Concentration 50; Iridoids; Medicine, Traditional; Mice; Phenols; Plant Components, Aerial; Plant Extracts; Skin

Olive leaves, an easily available natural low-cost material, constitute a source of extracts with significant antitumor activity that inhibits cell proliferation in several breast-cancer-cell models. In this work, a metabolite-profiling approach has been used to assess the uptake and metabolism of phenolic compounds from an olive-leaf extract in the breast-cancer-cell line SKBR3 to evaluate the compound or compounds responsible for the cytotoxic activity. For this, the extract was firstly characterized quantitatively by high-performance liquid chromatography coupled to electrospray ionization-quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS). Then, SKBR3 cells were incubated with 200 μg/mL of the olive-leaf extract at different times (15 min, 1, 2, 24, and 48 h). A metabolite-profiling approach based on HPLC-ESI-QTOF-MS was used to determine the intracellular phenolic compounds, enabling the identification of 16 intact phenolic compounds from the extract and four metabolites derived from these compounds in the cell cytoplasm. The major compounds found within the cells were oleuropein, luteolin-7-O-glucoside and its metabolites luteolin aglycone and methyl-luteolin glucoside, as well as apigenin, and verbascoside. Neither hydroxytyrosol nor any of its metabolites were found within the cells at any incubation time. It is proposed that the major compounds responsible for the cytotoxic activity of the olive-leaf extract in SKBR3 cells are oleuropein and the flavones luteolin and apigenin, since these compounds showed high uptake and their antitumor activity has been previously reported.

Topics: Apigenin; Breast Neoplasms; Carcinoma; Cell Line, Tumor; Chromatography, High Pressure Liquid; Cytoplasm; Female; Flavones; Glucosides; Humans; Iridoid Glucosides; Iridoids; Luteolin; Olea; Phenols; Plant Extracts; Plant Leaves; Pyrans; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry

In this study, we report the isolation and identification of several compounds from Plantago sempervirens Crantz, collected in the protected area of Majella National Park. We examined the polar fraction, in particular the iridoidic one. Aucubin, caryoptoside, plantarenaloside and gardoside were isolated and identified. For the first time, in this species, 8-epiloganic acid was recognised. Also, verbascoside, a phenylethanoid glycoside, was recognised in this plant.

Topics: Glucosides; Iridoid Glucosides; Iridoids; Italy; Magnetic Resonance Spectroscopy; Phenols; Plantago; Spectrometry, Mass, Electrospray Ionization

In this article, an efficient method was developed to screen, isolate and identify the major radical scavengers in the leaves of Olea europaea L. by DPPH-HPLC-DAD, HSCCC and NMR. The method of DPPH-HPLC-DAD was used to screen the major radical scavengers. It was found that three major constituents (A, B, C) in the extract of the leaves of O. europaea L. possessed potential antioxidant activities. In order to identify the chemical structures of those compounds, the HSCCC method with a two-phase solvent system composed of petroleum ether-ethyl acetate-water at an optimized volume ratio of 6:600:700 (v/v/v) together with column chromatography was developed to isolate and purify the active compounds. Pure compounds A (225 mg), B (10 mg) and C (12 mg) with purities 92.6, 95.1 and 96.4%, respectively, were obtained from the crude sample (500 mg). Their structures were identified as oleuropein (A), luteolin-7-O-glucoside (B) and verbascoside (C) by (1) H-NMR and (13) C-NMR.

Topics: Acetates; Chromatography, High Pressure Liquid; Flavones; Free Radical Scavengers; Glucosides; Iridoid Glucosides; Iridoids; Olea; Phenols; Plant Extracts; Plant Leaves; Pyrans

To establish HPLC chromatographic fingerprints to control the quality of Chinese herbal medicine. In this study, fingerprints were established based on HPLC-DAD chromatographs. And with these fingerprints, content variations of three important active components catalpol, 5-hydroxymethylfurfural and acteoside in Rehmannia rhizome were analyzed during processing, as well as changes of the fingerprints. Fingerprints comparing with the standard prepared Rehmannia fingerprints which came from the mean of prepared ones randomly chosen for standard was done to seek optimal processing time. The results indicated that catalpol decreased quickly as braising prolonged and almost vanished in the end. While the active component of 5-HMF increased linearly throughout the process of braising. And the content of acteoside did not show obvious change. Similarity to standard prepared Rehmannia reached summit after braising for 26 hours. So 26 hours could be considered to be the optimum time for braising prepared Rehmannia. Chromatographic fingerprint is convenient for revealing changes of constituents and for accurately controlling quality during processing prepared Rahmannia.

Topics: Chromatography; Chromatography, High Pressure Liquid; Dermatoglyphics; Drugs, Chinese Herbal; Furaldehyde; Glucosides; Iridoids; Phenols; Phytotherapy; Plant Preparations; Plant Structures; Rehmannia; Rhizome

To study the chemical constituents of Phlomis younghusbandii.. Column chromatography was used in the isolation procedure. The structures of isolated compounds were elucidated by spectral data. Eight compounds were isolated and their structures were identified as barlerin (1), sesamoside (2), phloyoside II (3), salidroside (4), shanzhiside methyl ester (5), acteoside (6), luteolin-7-O-glucoside (7), daucosterol (8).. Compound 4 is firstly isolated from Phlomis genus. Compound 4 and 6 are obtained from this plant for the first time.

Topics: Flavones; Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Molecular Structure; Phenols; Phlomis; Plant Roots; Plants, Medicinal; Pyrans

A continuous approach assisted by ultrasound for direct enrichment of edible oils (olive, sunflower, and soya) with the main phenols in olive leaves (i.e., oleuropein, verbascoside, apigenin-7-glucoside, and luteolin-7-glucoside) has been developed. Multivariate methodology was used to carry out a detailed optimization of the enrichment, and quantitation of the transferred compounds was based on LC-MS-MS in multiple reaction monitoring optimizing the most sensitive transition for each biophenol. Under the optimal working conditions, only 20 min is necessary to enrich the edible oils with 14.45-9.92 microg/mL oleuropein, 2.29-2.12 microg/mL verbascoside, 1.91-1.51 microg/mL apigenin-7-glucoside, and 1.60-1.42 microg/mL luteolin-7-glucoside. The enrichment method is carried out at room temperature and is organic-solvent-free; thus, the healthy properties of the edible oils improve as does their quality. Also, the low acquisition and maintenance costs of an ultrasound source and its application in a dynamic system make advisable the industrial implementation of the proposed method.

Topics: Apigenin; Dietary Fats, Unsaturated; Food, Fortified; Glucosides; Iridoid Glucosides; Iridoids; Luteolin; Olea; Phenols; Plant Leaves; Pyrans; Ultrasonics

Verminoside and verbascoside are natural compounds present in plants used in traditional medicine. They exhibit several biological activities including anti-inflammatory, anti-bacterial and anti-tumor properties. The potential applications of these compounds as ingredients in pharmaceutical formulations and cosmetics prompted us to investigate on cytotoxic and genotoxic activity of verminoside and verbascoside on human lymphocytes using genetic toxicity assays recommended in preclinical studies by the US Food and Drug Administration (FDA). We analyzed chromosome aberrations (CAs) and sister chromatid exchanges (SCEs) as well as the mitotic index (MI) and cell viability after the treatments with verminoside and verbascoside. This report is the first to clearly demonstrate a significant increase of structural CAs and SCEs on normal human lymphocytes associated with a reduction of the MI in both verminoside- and verbascoside-treated cells. Moreover, we observed enhanced protein expression levels of PARP-1 and p53 that are key regulatory proteins involved in cell proliferation and DNA repair. Interestingly, mass spectrometric analysis of the compounds in the culture supernatants also showed that verminoside remained unchanged during the culture period while verbascoside was hydrolyzed to its derivative, caffeic acid and the last one seems to be responsible for the observed biological activity.

Topics: Anti-Bacterial Agents; Anti-Inflammatory Agents, Non-Steroidal; Antineoplastic Agents, Phytogenic; Blotting, Western; Cell Line; Cell Survival; Chromosome Aberrations; Chromosomes; DNA Repair; Dose-Response Relationship, Drug; Glucosides; Humans; Iridoids; Lymphocytes; Male; Mitotic Index; Mutagens; Phenols; Poly (ADP-Ribose) Polymerase-1; Poly(ADP-ribose) Polymerases; Sister Chromatid Exchange; Spectrometry, Mass, Electrospray Ionization; Tumor Suppressor Protein p53

From the MeOH and ethyl acetate extracts of aerial parts of Penstemon gentianoides HBK (Plantaginaceae) an unusual iridoid of the catalpol-type, was isolated and characterized as pensteminoside: (8-O-trans-cinnamoyl, 6-hydroxy, 1-[beta-D-glucopyranoside-6'-O-((4''-hydroxy)-cinnamoyl)]-catalpol) was isolated, along with the known iridoids: plantarelanoside and globularisicin, the flavone: luteolin and diosmetin, as well the phenylpropanoids, verbascoside and martynoside. Their structures were established by 1D and 2D NMR spectroscopic analyses.

Topics: Flavones; Glucosides; Iridoids; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Penstemon; Phenols

Rapid production of reactive oxygen species (ROS) and upregulation of beta2 integrin by leucocytes are two important inflammatory responses in human leucocytes. To evaluate whether three phenylpropanoid glycosides (acteoside, crenatoside, and rossicaside B) and two iridoid glucosides (boschnaloside and 8-epideoxyloganic acid) identified from two medicinal plants with similar indications (Orobanche caerulescens and Boschniakia rossica) exhibited anti-inflammatory activity, their effects on N-formyl-methionyl-leucyl-phenylalanine (fMLP) and phorbol-12-myristate-13-acetate (PMA)-activated peripheral human neutrophils (PMNs) and mononuclear cells were examined. Pretreatment with 1-50 microM phenylpropanoid glycoside concentration-dependently diminished PMA- and fMLP-induced ROS production with IC50 values of approximately 6.8-23.9 and 3.0-8.8 muM, respectively. Iridoid glucoside was less effective than phenylpropanoid glycoside with an IC50 value of approximately 8.9-28.4 microM in PMA-activated PMNs and 19.1-21.1 microM in fMLP-activated mononuclear cells. Phenylpropanoid glycosides also effectively inhibited NADPH oxidase (NOX) and displayed potent free radical-scavenging activity, but did not interfere with pan-protein kinase C (PKC) activity. Furthermore, all compounds, except rossicaside B, significantly inhibited PMA- and fMLP-induced Mac-1 (a beta2 integrin) upregulation at 50 microM but not that of fMLP-induced intracellular calcium mobilization. These drugs had no significant cytotoxicity as compared with the vehicle control. Our data suggested that inhibition of ROS production, possibly through modulation of NOX activity and/or the radical scavenging effect, and beta2 integrin expression in leucocytes indicated that these compounds had the potential to serve as anti-inflammatory agents during oxidative stress.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Biphenyl Compounds; Caffeic Acids; CD18 Antigens; Cells, Cultured; Free Radicals; Glucosides; Humans; Hydrazines; Iridoids; Leukocytes, Mononuclear; Macrophage-1 Antigen; N-Formylmethionine Leucyl-Phenylalanine; NADPH Oxidases; Neutrophils; Phenols; Picrates; Protein Kinase C; Reactive Oxygen Species; Tetradecanoylphorbol Acetate

The monoterpenoid composition of Verbascum conocarpum and Scrophularia trifoliata, both endemic plants of Sardinia, was examined. The main chemotaxonomic markers of Scrophulariaceae, the iridoids aucubin, verbascoside and catalpol, were isolated.

Topics: Antineoplastic Agents, Phytogenic; Biomarkers; Classification; Glucosides; Humans; Iridoid Glucosides; Iridoids; Italy; Phenols; Phytotherapy; Plant Extracts; Quaternary Ammonium Compounds; Scrophularia; Verbascum

This work is focused on the recovery and structural characterisation of bioactive compounds from SOR (solid olive residue), a low cost and widely available by-product in the Mediterranean basin. In the light of the interesting biological activities attributed both to secoiridoid and phenylpropanoids, the aim of this work was to carry out a systematic tandem mass spectrometric study for the identification and characterisation of these two class of compounds extracted from SOR derived from Coratina, a cultivar widely diffused in the south of Italy. Five phenylpropanoids, in addition to verbascoside, and two new secoiridoids were identified.

Topics: Chromatography, High Pressure Liquid; Glucosides; Iridoids; Italy; Molecular Structure; Olea; Phenols; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry

To study the chemical constituents from Clerodendron bungei Steud.. The compounds were isolated and purified by various chromatographic techniques and identified by their physicochemical properties and spectral data.. Ten phenylethanoid glycosides were isolated and identified as clerodendronoside (1), acteoside (2), isoacteoside (3), cistanoside C (4), jionoside C (5), leucosceptoside A (6), cistanoside D (7), campneoside I (8), campneoside II (9), cistanoside F (10).. Compound 1 is a new phenylethanoid glycoside, while compounds 4-10 are obtained from this plant for the first time.

Topics: Catechols; Clerodendrum; Glucosides; Glycosides; Iridoid Glycosides; Iridoids; Molecular Structure; Phenols; Plant Components, Aerial; Plants, Medicinal

Kigelia africana is a plant used in Africa for anti-inflammatory, anti-microbial, and anti-skin-aging effects. Various papers have reported on the composition and biological activities of its CH2Cl2 extracts and dermal formulations. Chemical analysis of a polar extract of fruit from K. africana indicated the presence of verminoside (1), an iridoid, as a major constituent, and of a series of polyphenols such as verbascoside (2). In vitro assays showed that 1 had significant anti-inflammatory effects, inhibiting both iNOS expression and NO release in the LPS-induced J774.A1 macrophage cell line. Cytotoxicity and cutaneous irritation of the extract and of compounds 1 and 2 were investigated. The crude extract and 1 did not affect cell viability in vitro either in cells grown in monolayers (ML) or in the reconstituted human epidermis (RHE, 3D) model; neither caused release of pro-inflammatory mediators or histomorphological modification of RHE.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Bignoniaceae; Cells, Cultured; Epidermis; Fruit; Glucosides; Humans; Iridoids; Macrophages; Mali; Mice; Models, Biological; Molecular Structure; Monocytes; Nitric Oxide; Nitric Oxide Synthase Type II; Phenols; Plants, Medicinal

The aim of this study was to evaluate the in vitro antioxidant activity of the methanol extract of Plantago bellardii All. aerial parts. This was assessed by two different tests, scavenging of 1,1-diphenyl-2-picrylhydrazil (DPPH) radical, and inhibition of lipid peroxidation on liposomes prepared from bovine brain extract. In both tests the extract showed a potent antioxidant effect. The characterization of the major compounds in the extract as rutin, geniposide and verbascoside was performed by isolation and HPLC comparison with authentic samples. They were quantified by HPLC for the flavonoids and colorimetry for iridoids. The compounds that contribute most to the antioxidant activity were shown to be verbascoside and rutin.

Topics: Antioxidants; Glucosides; Iridoid Glucosides; Iridoids; Molecular Structure; Phenols; Plant Extracts; Plantago; Pyrans; Rutin

Nepeta ucrainica L. is used as a herbal tea in Kazakhistan. Phytochemical investigations of the aerial parts of the plant resulted in the isolation of verbascoside (1) and 1,5,9-epi-deoxyloganic acid (2). The structures of the compounds were elucidated by spectral (UV, IR, (1)H-NMR and (13)C-NMR) methods and HPLC analysis. The in vitro immunomodulatory activity of verbascoside was investigated by assessing neutrophil function; chemotaxis and intracellular killing activity. Verbascoside showed an increased chemotactic activity in all doses applied compared with the medium used as a negative control and had a positive effect on respiratory burst of neutrophils, but there was an opposite effect with increasing doses, pointing to a possible suppression of neutrophil intracellular killing activity.

Topics: Adjuvants, Immunologic; Alkaloids; Beverages; Chemotaxis; Chromatography, High Pressure Liquid; Glucosides; Humans; Iridoid Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Molecular Structure; Nepeta; Neutrophils; Phenols; Plant Extracts; Respiratory Burst; Spectrophotometry, Ultraviolet

As part of our screening of antiviral agents from medicinal plants, 11 compounds from plant origin (Bupleurum rigidum and Scrophularia scorodonia), three saikosaponins, seven iridoids and one phenylpropanoid glycoside were tested in vitro against herpes simplex type I (HSV-1), vesicular stomatitis virus (VSV) and poliovirus type 1. Five of these compounds showed antiviral activity against VSV. The percentages of cellular viability at the non-toxic limit concentrations of the active compounds were: verbascoside 53.6 % at 500 microg/ml, 8-acetylharpagide 32.1 % at 500 microg/ml, harpagoside 43.3 % at 450 microg/ml, scorodioside 47.8 % at 500 microg/ml and buddlejasaponin IV 56.9 % at 25 microg/ml. Although none of the saikosaponins were active against HSV-1, the iridoid scorodioside showed moderate in vitro anti-HSV-1 activity (30.6 % at 500 microg/ml). However, none of the compounds tested in this survey had any effect against poliovirus.

Topics: Animals; Antiviral Agents; Bupleurum; Carbohydrate Sequence; Cell Line; Chlorocebus aethiops; Cricetinae; Dose-Response Relationship, Drug; Glucosides; HeLa Cells; Herpesvirus 1, Human; Humans; Iridoids; Medicine, Traditional; Molecular Sequence Data; Oleanolic Acid; Phenols; Plant Extracts; Poliovirus; Pyrans; Sapogenins; Saponins; Scrophulariaceae; Vero Cells; Vesicular stomatitis Indiana virus

The plantain is used in herbal medicines and for pasturage. Two cultivars of plantain (Plantago lanceolata L.), Grasslands Lancelot and Ceres Tonic, were sown in spring. Changes in catalpol, aucubin, and acteoside concentrations in the leaves during the growing season and by drying after harvesting were quantitatively determined by high-performance liquid chromatography. The concentration of catalpol was relatively low, fluctuating between 1 and 2% of dry matter during the growing season, and there was no clear-cut seasonal change. From spring to midfall, the aucubin concentration increased from 2.1 to 4.8% in Grasslands Lancelot and from 1.0 to 2.7% in Ceres Tonic. These increases were gradual over the season, except for during midsummer, when aucubin concentrations were relatively constant. The acteoside concentration increased from 3.4 to 7.1% in Grasslands Lancelot and from 1.5 to 4.1% in Ceres Tonic over the course of the growing season, although in the summer it declined steadily to lows of 2.5% in Grasslands Lancelot and 1.9% in Ceres Tonic. Our data suggested that midfall was the appropriate time for harvesting plantain for medicinal use. The concentrations of the bioactive compounds steadily decreased in the initial stages of drying both under natural climatic conditions and at 60 degrees C. The development of processing methods to minimize the loss of bioactive compounds is imperative.

Topics: Chromatography, High Pressure Liquid; Climate; Desiccation; Glucosides; Iridoid Glucosides; Iridoids; Phenols; Plant Leaves; Plantago; Pyrans; Seasons

A new phenylethanoid glycoside, persicoside (1) and three known phenylethanoid glycosides, acteoside (2), isoacteoside (3) and lavandulifolioside (4) were isolated from the aerial parts of Veronica persica. On the basis of spectral analyses, the structure of the new compound was elucidated to be 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-4-O-caffeoyl-beta-D-glucopyranoside. Persicoside (1) and acteoside (2) exhibited radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Beside phenylethanoid glycosides, a hexitol, dulcitol (5) and seven known iridoid glucosides, aucubin (6), veronicoside (7), amphicoside (8), 6-O-veratroyl-catalpol (9), catalposide (10), verproside (11) and verminoside (12) were isolated.

Topics: Glucosides; Iridoids; Oligosaccharides; Phenols; Pyrans; Scrophulariaceae

Repair effect on 2'-deoxyadenosine-5'-monophosphate (dAMP) radical anions by phenylpropanoid glycosides (PPGs) and their analogs, isolated from Chinese folk medicinal herb, was studied using pulse radiolysis technique. The radical anion of dAMP was formed by the reaction of hydrated electron with dAMP. On pulse irradiation of nitrogen-saturated dAMP aqueous solution containing 0.2 M t-BuOH and one of PPGs or their analogs, the transient absorption spectrum of the radical anion of dAMP decayed with the formation of that of the radical anion of PPGs or their analogs within several decades of microseconds after electron pulse irradiation. The results indicated that dAMP radical anions can be repaired by PPGs or their analogs. The rate constants of the repair reactions were deduced to be 1.6-4.5 x 10(8) M(-1) s(-1).

Topics: Anions; Antioxidants; Deoxyadenine Nucleotides; DNA Repair; Free Radical Scavengers; Glucosides; Iridoid Glucosides; Iridoids; Phenols; Pulse Radiolysis

The isolation and identification of two cardioactive compounds from two Eremophila species (Myoporaceae) considered important in the pharmacopoeia of the Australian Aboriginal people is described. Verbascoside, isolated from the methanol and water extracts of E. alternifolia leaves, mediated significant increases in chronotropism, inotropism and coronary perfusion rate (CPR) in the Langendorff rat heart. Geniposidic acid, isolated from the methanol extract of E. longifolia leaves, mediated an inhibitory effect with significant negative chronotropism, negative inotropism and CPR.

Topics: Animals; Antioxidants; Australia; Coronary Circulation; Drugs, Chinese Herbal; Female; Glucosides; Heart Rate; Iridoid Glucosides; Iridoids; Medicine, Traditional; Methanol; Myocardial Contraction; Phenols; Plant Extracts; Plant Leaves; Pyrans; Rats; Rats, Wistar; Structure-Activity Relationship

The activities of six phenylpropanoid glycosides as chain-breaking antioxidants have been studied for the autoxidation of linoleic acid in cetyl trimethylammonium bromide (CTAB) micelles at 37 degrees C. Verbascoside, isoverbascoside, echinacoside and pedicularioside A, which possess four phenolic hydroxyl groups, exhibited antioxidant activities, while cistanoside D possessing only two phenolic hydroxyl groups and permethyl verbascoside without phenolic hydroxyl group did not suppress the oxidation appreciably. The ratio of rate constants for inhibition and propagation kinh/kp and stoichiometric factor n were determined.

Topics: Amidines; Cetrimonium; Cetrimonium Compounds; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Kinetics; Linoleic Acid; Linoleic Acids; Lipid Peroxidation; Micelles; Oxidation-Reduction; Oxygen Consumption; Phenols; Plant Extracts; Plants, Medicinal