humulene and myrcene

Topics: Acyclic Monoterpenes; Alkenes; Analgesics; Animals; Anti-Inflammatory Agents; Arthralgia; Arthritis; Cannabidiol; Cannabinoid Receptor Agonists; Cannabis; Chronic Pain; Hallucinogens; Inflammation; Male; Rats; Rats, Wistar; Terpenes

It is well known that duration of pre-drying storage impacts on hop quality. However, little knowledge exists regarding its actual effects on valuable hop components. To investigate these effects, fresh hop cones were stored for 5 or 24 h and dried for 210 min at 65 °C thereafter. Furthermore, to understand the effect of freezing hop cones on the essential oil content, both fresh and stored samples were frozen before and after drying.. The results from gas chromatography analysis show an increase in linalool, β-caryophyllene, humulene, geraniol content and decrease in myrcene content dependent on the period of storage. Total colour difference ΔE values of 4.61 and 5.27 were obtained for fresh and stored hops respectively, indicating discoloration of hops during storage. Modelling of moisture curves revealed the Wang and Singh model to be suitable, with. The results from this study provide an in-depth understanding on the changes occurring within the hop cones both during storage and drying and will further help hop processors optimize their storage times.

Topics: Acyclic Monoterpenes; Alkenes; Chromatography, Gas; Desiccation; Food Handling; Hot Temperature; Humulus; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Time Factors

The aim of this work was to find the correlation between the content of ergosterol in fungi membrane and the action of the hop essential oil, myrcene and humulene on its properties. To reach this goal, the monolayers and bilayers composed of phosphatidylcholine, phosphatidyethanol amine and ergosterol, differing in the concentration of sterol, were used as model membrane systems. The impact of the essential oil and its major terpenes on one component ergosterol film was also investigated. It was found that pure isolated terpenes, in contrast to the hop oil being the mixture of them, do not incorporate into pure ergosterol membrane, however, they cause the loss of monolayer material from the interface. These results are in contrast to the effect of these terpenes on phospholipid films reported previously and they may suggest a strong effect of ergosterol on the behavior of terpenes in the mixed systems. Surprisingly, for model membranes, the effect of myrcene was qualitatively similar to the effect of the hop oil and ergosterol was found to regulate the incorporation of both these substances into the film. In contrast, very strong correlation between ergosterol content and the action of humulene was found. Namely, the ability of humulene to change model membrane properties was found to increase with ergosterol concentration. Additionally, the differentiating effect of ergosterol on humulene action in membranes was much more pronounced than for myrcene or the hop oil. Interestingly, at the highest ergosterol level the influence of humulene was even stronger than the effect of the hop oil. This is very important finding suggesting that ergosterol may regulate the sensitivity of particular membrane to the impact of humulene. Summarizing, ergosterol substantially differentiates the effect of the hop oil, myrcene and humulene on the lipid systems and it can be the molecule important for antifungal effect of the essential oil and terpenes.

Topics: Acyclic Monoterpenes; Alkenes; Cell Membrane; Ergosterol; Fungi; Lipid Bilayers; Liposomes; Monocyclic Sesquiterpenes; Oils, Volatile; Phosphatidylcholines; Phospholipids; Phytochemicals; Sterols; Surface Tension; Terpenes

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Glycyrrhiza; Iran; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

The profile and bioactivity of hops (Humulus lupulus L.) essential oil, a complex natural product extracted from cones via steam distillation, depends on genetic and environmental factors, and may also depend on extraction process. We hypothesized that compound mixtures eluted sequentially and captured at different timeframes during the steam distillation process of whole hop cones would have differential chemical and bioactivity profiles. The essential oil was collected sequentially at 8 distillation time (DT) intervals: 0-2, 2-5, 5-10, 10-30, 30-60, 60-120, 120-180, and 180-240 min. The control was a 4-h non-interrupted distillation. Nonlinear regression models described the DT and essential oil compounds relationship. Fractions yielded 0.035 to 0.313% essential oil, while control yielded 1.47%. The oil eluted during the first hour was 83.2%, 9.6% during the second hour, and only 7.2% during the second half of the distillation. Essential oil (EO) fractions had different chemical profile. Monoterpenes were eluted early, while sequiterpenes were eluted late. Myrcene and linalool were the highest in 0-2 min fraction, β-caryophyllene, β-copaene, β-farnesene, and α-humulene were highest in fractions from middle of distillation, whereas α- bergamotene, γ-muurolene, β- and α-selinene, γ- and δ-cadinene, caryophyllene oxide, humulne epoxide II, τ-cadinol, and 6-pentadecen-2-one were highest in 120-180 or 180-240 min fractions. The Gram-negative Escherichia coli was strongly inhibited by essential oil fractions from 2-5 min and 10-30 min, followed by oil fraction from 0-2 min. The strongest inhibition activity against Gram-negative Yersinia enterocolitica, and Gram-positive Clostridium perfringens, Enterococcus faecalis, and Staphylococcus aureus subs. aureus was observed with the control essential oil. This is the first study to describe significant activity of hops essential oils against Trypanosoma brucei, a parasitic protozoan that causes African trypanosomiasis (sleeping sickness in humans and nagana in other animals). Hops essential oil fractions or whole oil may be used as antimicrobial agents or for the development of new drugs.

Topics: Acyclic Monoterpenes; Alkenes; Antiprotozoal Agents; Bridged Bicyclo Compounds; Clostridium perfringens; Distillation; Drug Resistance, Bacterial; Enterococcus faecalis; Escherichia coli; Humulus; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Staphylococcus aureus; Steam; Trypanosoma brucei brucei; Yersinia enterocolitica

Cannabis possesses a rich spectrum of phytochemicals i.e. cannabinoids, terpenes and phenolic compounds of industrial and medicinal interests. Most of these high-value plant products are synthesised in the disk cells and stored in the secretory cavity in glandular trichomes. Conventional trichome analysis was so far based on optical microscopy, electron microscopy or extraction based methods that are either limited to spatial or chemical information. Here we combine both information to obtain the spatial distribution of distinct secondary metabolites on a single-trichome level by applying Coherent anti-Stokes Raman scattering (CARS), a microspectroscopic technique, to trichomes derived from sepals of a drug- and a fibre-type.. Here we demonstrate a label-free and non-destructive method to analyse the distribution of secondary metabolites and distinguish between different cell and chemo-types with high spatial resolution on a single trichome. The record of chemical fingerprints of single trichomes offers the possibility to optimise growth conditions as well as guarantee a direct process control for industrially cultivated medicinal Cannabis plants. Moreover, this method is not limited to Cannabis related issues but can be widely implemented for optimising and monitoring all kinds of natural or biotechnological production processes with simultaneous spatial and chemical information.

Topics: Acyclic Monoterpenes; Alkenes; Cannabinoids; Cannabis; Dronabinol; Imaging, Three-Dimensional; Microscopy, Electron, Scanning; Monoterpenes; Oils, Volatile; Plants, Medicinal; Secondary Metabolism; Spectrum Analysis, Raman; Terpenes; Trichomes

Mosquitoes (Diptera: Culicidae) are important vectors of terms of public health relevance, especially in tropical and sub-tropical regions. The continuous and indiscriminate use of conventional pesticides for the control of mosquito vectors has resulted in the development of resistance and negative impacts on non-target organisms and the environment. Therefore, there is a need for development of effective mosquito control tools. In this study, the larvicidal and repellent activity of Zingiber nimmonii rhizome essential oil (EO) was evaluated against the malaria vector Anopheles stephensi, the dengue vector Aedes aegypti, and the lymphatic filariasis vector Culex quinquefasciatus. The chemical composition of the EO was analyzed by gas chromatography-mass spectroscopy (GC-MS). GC-MS revealed that the Z. nimmonii EO contained at least 33 compounds. Major constituents were myrcene, β-caryophyllene, α-humulene, and α-cadinol. In acute toxicity assays, the EO showed significant toxicity against early third-stage larvae of An. stephensi, Ae. aegypti, and Cx. quinquefasciatus, with LC50 values of 41.19, 44.46, and 48.26 μg/ml, respectively. Repellency bioassays at 1.0, 2.0, and 5.0 mg/cm(2) of Z. nimmonii EO gave 100 % protection up to 120, 150, and 180 min. against An. stephensi, followed by Ae. aegypti (90, 120, and 150 min) and Cx. quinquefasciatus (60, 90, and 120 min). Furthermore, the EO was safer towards two non-target aquatic organisms, Diplonychus indicus and Gambusia affinis, with LC50 values of 3241.53 and 9250.12 μg/ml, respectively. Overall, this research adds basic knowledge to develop newer and safer natural larvicides and repellent from Zingiberaceae plants against malaria, dengue, and filariasis mosquito vectors.

Topics: Acyclic Monoterpenes; Aedes; Alkenes; Animals; Anopheles; Culex; Dengue; Elephantiasis, Filarial; Gas Chromatography-Mass Spectrometry; Insect Repellents; Insecticides; Larva; Malaria; Monocyclic Sesquiterpenes; Monoterpenes; Mosquito Control; Mosquito Vectors; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Zingiberaceae

Absorption of hop volatiles by crown cork liner polymers and can coatings was investigated in beer during storage. All hop volatiles measured were prone to migrate into the closures, and the absorption kinetics was demonstrated to fit Fick's second law of diffusion well for a plane sheet. The extent and rate of diffusion were significantly dissimilar and were greatly dependent upon the nature of the volatile. Diffusion coefficients ranged from 1.32 × 10(-5) cm(2)/day (limonene) to 0.26 × 10(-5) cm(2)/day (α-humulene). The maximum amounts absorbed into the material at equilibrium were in the following order: limonene > α-humulene > trans-caryophyllene > myrcene ≫ linalool > α-terpineol > geraniol. With the application of low-density polyethylene (LDPE) liners with oxygen-scavenging functionality, oxygen-barrier liners made up from high-density polyethylene (HDPE) or liner polymers from a different manufacturer had no significant effect on the composition of hop volatiles in beers after prolonged storage of 55 days; however, significantly higher amounts of myrcene and limonene were found in the oxygen-barrier-type crown cork, while all other closures behaved similarly. Can coatings were demonstrated to absorb hop volatiles in a similar pattern as crown corks but to a lesser extent. Consequently, significantly higher percentages of myrcene were found in the beers.

Topics: Acyclic Monoterpenes; Alkenes; Beer; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Humulus; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Polycyclic Sesquiterpenes; Polyethylene; Polymers; Sesquiterpenes; Terpenes

Hop cones, the immature inflorescences of the female plant of Humulus lupulus L., have been used for centuries to improve the flavor of beer and can be also used for a great variety of other products. Four samples of hop, belonging to three different cultivars (Nugget, Saaz and Perle), were studied in the present work. Headspace solid-phase microextraction and hydrodistillation techniques were used to obtain the volatile profiles of the samples.. Independent of the technique employed, over 40 volatile compounds were detected in the hop pellet samples (esters, monoterpenes, monoterpenoids, sesquiterpenes and sesquiterpenoids). Sesquiterpenes and sesquiterpenoids represented the majority of the total aromatic compounds. The main compounds for all cultivars were myrcene, β-caryophyllene and humulene, but the presence of high amounts of β-farnesene in Saaz cultivar was highlighted.. Both techniques were suitable for studying qualitatively the volatile composition of hop pellets, but some differences were shown when studying the proportion of the main constituents of the volatile profiles. Understanding these differences may help researchers design future studies to advise the industry how to exploit the potential of each hop cultivar.

Topics: Acyclic Monoterpenes; Alkenes; Beer; Distillation; Humulus; Inflorescence; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Solid Phase Microextraction; Species Specificity