caryophyllene and beta-farnesene

Medicinal plants and herbal preparations are gaining attention in the scientific community today, as they are often used intermittently in the treatment of various diseases. The genus of Polygonum (Polygonaceae), known locally as “madimak”, is an aromatic plant widely used in world flavors. The chemical composition of the essential oils of dried aerial parts of seven of Polygonum was analyzed by GC-MS. These species are Polygonum lapathifolium L., Polygonum persicaria L., Polygonum arenastrum Bor., Polygonum bellardii All., Polygonum arenarium Waldst. Et Kit., Polygonum aviculare L., and Polygonum cognatum Meissn. Qualitative and quantitative differences were found in the essential oil analysis of the seven Polygonum species. The major compounds were determined as (E)-β-farnesene (19. 46%), dodecanal (15.92%), β-caryophyllene (12.95%), in P. aviculare; (E)-β-farnesene (25.00%), dodecanal (20.45%), β-caryophyllene (9.38%), and caryophyllene oxide (8. 26%) in P. persicaria; dodecanal (25.65%), caryophyllene oxide (13.35%), β-caryophyllene (7.95%), and (E)-β-farnesene (6.20%) in P. lapathifolium, and dodecanal (19.65%), (E)-β-farnesene (13.86%), β-caryophyllene (8.06%), and α-terpineol (7.2%) in P. arenarium, dodecanal (16.23%), β-caryophyllene (16.09%), (E)-β-farnesene (12.26%), caryophyllene oxide (7.94%) in P. bellardii, (E)-β-farnesene (20.75%), dodecanal (17.96%), β-caryophyllene (13.01%), α-terpineol (4.97%) in P. arenastrum, (E)-β-farnesene (9.49%), dodecanal (14.01%), β-caryophyllene (11.92%), geranyl acetate (9.49%), and undecanal (7.35%) in P. cognatum. This study is the most comprehensive study conducted to determine the essential oil components of Polygonum species. In addition, a literature review on the composition of the essential oils of these Polygonum taxa was performed. The essential oil components of the species in our study were revealed for the first time with this study.

Topics: Oils, Volatile; Plant Oils; Polygonum; Turkey

Topics: Anti-Bacterial Agents; Antineoplastic Agents, Phytogenic; Antiprotozoal Agents; Brazil; Gas Chromatography-Mass Spectrometry; Humans; Lauraceae; Leishmania; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes

Herbivorous insects use olfactory cues to locate their host plant within a complex olfactory landscape. One such example is the European grapevine moth Lobesia botrana, a key pest of the grape in the Palearctic region, which recently expanded both its geographical and host plant range. Previous studies have showed that a synthetic blend of the three terpenoids, (E)-β-caryophyllene, (E)-β-farnesene and (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), was as attractive for the moth as the complete grape odour profile in laboratory conditions. The same studies also showed that the specific ratio of these compounds in the grape bouquet was crucial because a percentage variation in any of the three volatiles resulted in almost complete inhibition of the blend's attractiveness. Here, we report on the creation of stable grapevine transgenic lines, with modified (E)-β-caryophyllene and (E)-β-farnesene emission and thus with an altered ratio compared to the original plants. When headspace collections from these plants were tested in wind tunnel behavioural assays, they were less attractive than control extracts. This result was confirmed by testing synthetic blends imitating the ratio found on natural and transformed plants, as well as by testing the plants themselves. With this evidence, we suggest that a strategy based on volatile ratio modification may also interfere with the host-finding behaviour of L. botrana in the field, creating avenues for new pest control methods.

Topics: Animals; Moths; Odorants; Polycyclic Sesquiterpenes; Sesquiterpenes; Vitis

Topics: Antineoplastic Agents, Phytogenic; Antineoplastic Combined Chemotherapy Protocols; Cell Proliferation; Drug Screening Assays, Antitumor; Garcinia; Gas Chromatography-Mass Spectrometry; Humans; MCF-7 Cells; Oils, Volatile; Plant Bark; Plant Leaves; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes; Tamoxifen

The chemical composition of essential oil obtained from the aerial parts of Ajuga comata Stapf. was analyzed by GC and GC/MS. Thirty-seven components were identified in the oil. (E)-β-caryophyllene (30.9%), caryophyllene oxide (24.9%), (E)-β-farnesene (12.6%), β-eudesmol (3.2%), δ-cadinene (3.1%) and germacrene D (3.0%) were the main compounds in the EOs. The chemical composition of A. comata Stapf. from the Southern Zagros of Iran is reported for the first time.

Topics: Ajuga; Gas Chromatography-Mass Spectrometry; Iran; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Sesquiterpenes, Germacrane

Ferula communis is a showy herbaceous plant typical of the Mediterranean area where it is used as a traditional medicine. The plant is a source of bioactive compounds such as daucane sesquiterpenes and prenylated coumarins. In Italy, most of phytochemical studies focused on Sardinian populations where poisonous and nonpoisonous chemotypes were found, while investigations on peninsular populations are scarce. In this work, we report the chemical characterisation of the essential oils obtained from different parts of F. communis growing in central Italy. The chemical profiles of the plant parts, as detected by GC-FID and GC-MS, were different from each other and from those reported in insular populations. Notably, α-pinene (10.5%), γ-terpinene (7.6%) and hedycariol (8.4%) were the major volatile constituents in flowers; α-pinene (55.9%), β-pinene (16.8%) and myrcene (5.9%) in fruits; β-eudesmol (12.1%), α-eudesmol (12.1%) and hedycariol (10.3%) in leaves; (E)-β-farnesene (9.5%), β-cubebene (8.2%) and (E)-caryophyllene (7.2%) in roots. The volatile profiles detected did not allow to classify the investigated central Italy population into the poisonous and nonpoisonous chemotypes previously described in Sardinia.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Coumarins; Cyclohexane Monoterpenes; Ferula; Flowers; Fruit; Gas Chromatography-Mass Spectrometry; Italy; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Roots; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane

There are many biosynthetic pathways competing for the metabolic flux with the artemisinin biosynthetic pathway in Artemisia annua L. To study the relationship between genes encoding enzymes at branching points and the artemisinin biosynthetic pathway, β-caryophyllene, β-farnesene and squalene were sprayed on young seedlings of A. annua. Transient expression assays indicated that the transcription levels of β-caryophyllene synthase (CPS), β-farnesene synthase (BFS) and squalene synthase (SQS) were inhibited by β-caryophyllene, β-farnesene and squalene, respectively, while expression of some artemisinin biosynthetic pathway genes increased. Thus, inhibition of these genes encoding enzymes at branching points may be helpful to improve the artemisinin content. For further study, the expression levels of four branch pathway genes CPS, BFS, germacrene A synthase (GAS) and SQS were down-regulated by the antisense method in A. annua. In anti-CPS transgenic plants, mRNA levels of BFS and ADS were increased, and the contents of β-farnesene, artemisinin and dihydroartemisinic acid (DHAA) were increased by 212, 77 and 132%, respectively. The expression levels of CPS, SQS, GAS, amorpha-4,11-diene synthase (ADS), amorphadiene 12-hydroxylase (CYP71AV1) and aldehyde dehydrogenase 1 (ALDH1) were increased in anti-BFS transgenic plants and, at the same time, the contents of artemisinin and DHAA were increased by 77% and 54%, respectively, and the content of squalene was increased by 235%. In anti-GAS transgenic plants, mRNA levels of CPS, BFS, ADS and ALDH1 were increased. The contents of artemisinin and DHAA were enhanced by 103% and 130%, respectively. In anti-SQS transgenic plants, the transcription levels of BFS, GAS, CPS, ADS, CYP71AV1 and ALDH1 were all increased. Contents of artemisinin and DHAA were enhanced by 71% and 223%, respectively, while β-farnesene was raised to 123%. The mRNA level of artemisinic aldehyde Δ11(13) reductase (DBR2) had changed little in almost all transgenic plants.

Topics: Artemisia annua; Artemisinins; Biosynthetic Pathways; Farnesyl-Diphosphate Farnesyltransferase; Gene Expression Regulation, Plant; Genes, Plant; Lactones; Plant Proteins; Plants, Genetically Modified; Polycyclic Sesquiterpenes; Pyrophosphatases; Sesquiterpenes; Squalene; 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

Optimisation of alginate formulations is described in order to develop semiochemical (E-β-farnesene and E-β-caryophyllene) slow-release devices in biological control approaches by attracting predators and parasitoids of aphids. Various formulation criteria were optimised with respect to semiochemical encapsulation capacity. Moreover, the optimised formulation was characterised by texturometry and confocal microscopy. The slow-release rates of semiochemicals were calculated in laboratory controlled conditions. The attractiveness of semiochemical formulations towards Aphidius ervi was demonstrated by olfactometry.. Two major parameters were highlighted in encapsulation optimisation: the type of alginate (Sigma L) and the type of crosslinker ion (Ca(2+)). Other formulation parameters were optimised: ionic strength (0.5 M), Ca(2+) (0.2 M) and alginate (1.5%) concentrations and the maturation time of beads in CaCl(2) solution (48 h). After physical characterisation of beads, semiochemical slow-release measurements showed that alginate formulations were efficient sesquiterpene releasers, with 503 µg of E-β-farnesene and 1791 µg of E-β-caryophyllene totally released in 35 days. The efficiency of semiochemical alginate beads as attractants for female parasitoids was demonstrated, with high percentages of attraction for semiochemical odours (88 and 90% for E-β-farnesene and E-β-caryophyllene respectively) and significant statistical results.. Semiochemical alginate beads can be considered as efficient slow-release systems in biological control. These formulations could be very useful to attract aphid parasitoids on crop fields.

Topics: Alginates; Animals; Aphids; Chemistry, Pharmaceutical; Delayed-Action Preparations; Female; Glucuronic Acid; Hexuronic Acids; Pest Control, Biological; Pheromones; Polycyclic Sesquiterpenes; Sesquiterpenes; Wasps

Sorghum (Sorghum bicolor) plants damaged by insects emit a blend of volatiles, predominantly sesquiterpenes, that are implicated in attracting natural enemies of the attacking insects. To characterize sesquiterpene biosynthesis in sorghum, seven terpene synthase (TPS) genes, SbTPS1 through SbTPS7, were identified based on their evolutionary relatedness to known sesquiterpene synthase genes from maize and rice. While SbTPS6 and SbTPS7 encode truncated proteins, all other TPS genes were determined to encode functional sesquiterpene synthases. Both SbTPS1 and SbTPS2 produced the major products zingiberene, β-bisabolene and β-sesquiphellandrene, but with opposite ratios of zingiberene to β-sesquiphellandrene. SbTPS3 produced (E)-α-bergamotene and (E)-β-farnesene. SbTPS4 formed (E)-β-caryophyllene as the major product. SbTPS5 produced mostly (E)-α-bergamotene and (Z)-γ-bisabolene. Based on the genome sequences of sorghum, maize and rice and the sesquiterpene synthase genes they contain, collinearity analysis identified the orthologs of sorghum sesquiterpene synthase genes, except for SbTPS4, in maize and rice. Phylogenetic analysis implied that SbTPS1, SbTPS2 and SbTPS3, which exist as tandem repeats, evolved as a consequence of local gene duplication in a lineage-specific manner. Structural modeling and site-directed mutagenesis experiments revealed that three amino acids in the active site play critical roles in defining product specificity of SbTPS1, SbTPS2, SbTPS3 and their orthologs in maize and rice. The naturally occurring functional variations of sesquiterpene synthases within and between species suggest that multiple mechanisms, including lineage-specific gene duplication, subfunctionalization, neofunctionalization and pseudogenization of duplicated genes, have all played a role in the dynamic evolution of insect-induced sesquiterpene biosynthesis in grasses.

Topics: Alkyl and Aryl Transferases; Animals; Biological Evolution; Bridged Bicyclo Compounds; Catalytic Domain; Gene Duplication; Herbivory; Insecta; Monocyclic Sesquiterpenes; Mutagenesis, Site-Directed; Oryza; Phylogeny; Plant Proteins; Polycyclic Sesquiterpenes; Sesquiterpenes; Sorghum; Volatile Organic Compounds; Zea mays

The essential oil from the flowering aerial parts of Bupleurum hamiltonii Balak syn. Bupleurum tenue family Apiaceae (Umbellifereae) was obtained by steam distillation and analysed by a combination of GC (RI) and GC-MS. The chemical composition of the isolated oil is reported here for the first time. Twenty-seven compounds were identified, which represent 92.7% of the total oil. The chemical composition of the isolated oil was characterised by a high proportion of sesquiterpene hydrocarbons (61.9%), among which germacrene-D (17.8%), trans-β-farnesene (14.7%) and β-caryophyllene (13.1%) were the predominant compounds. The monoterpene hydrocarbons (16.6%) represented the second major fraction of the same oil followed by the oxygenated sesquiterpenes (7.9%).

Topics: Bupleurum; India; Oils, Volatile; Plant Components, Aerial; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

The essential-oil compositions of Pinus heldreichii Christ. from Montenegro and Serbia are reported at the population level. Whitebark pine is a sub-endemic high-mountain Balkan pine relict of an anthropogenically reduced area, with large morphological diversity and insufficiently clear taxonomic position. In the pine-needle terpene profile from three populations from Montenegro, and one from Serbia, 101 compounds were detected, 72 of which could be identified (Table 3). The dominant constituents are limonene (26.3%), alpha-pinene (17.5%), germacrene D (13.5%), and beta-caryophyllene (10.4%), comprising ca. 67.7% of the essential oil. Medium-to-high contents (0.5-10%) of the following 16 additional components were found: beta-pinene, beta-myrcene, alpha-humulene, delta-cadinene, alpha-muurolene, (E)-hex-2-enal, beta-gurjunene, gamma-muurolene, isopimarol, camphene, gamma-cadinene, aromadendrene, beta-bisabolene, trans-beta-farnesene, alpha-cadinene, and (Z)-hex-3-en-1-ol. The similarity of the populations and the within-population variability was visualized by principle-component analysis (PCA) of eleven selected terpenes in 97 tree samples. Cluster and genetic analyses suggest closest connection between the two spatially most-distant populations I (Montenegro) and IV (Serbia). Based on the profile of the main sesquiterpene components, the studied populations from Montenegro and Serbia are more similar to the populations from Greece and the Central Balkan peninsula (Bosnia and Serbia-Kosovo) than to those on the furthest eastern margin of their natural range (Bulgaria).

Topics: Acyclic Monoterpenes; Azulenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexenes; Limonene; Monoterpenes; Oils, Volatile; Pinus; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Yugoslavia

The role of two volatile sesquiterpenes, (E)-beta-farnesene and (-)-beta-caryophyllene, in the chemical ecology of the multicolored Asian lady beetle, Harmonia axyridis Pallas, was investigated by using both electrophysiological and behavioral techniques. (E)-beta-Farnesene is the major component of the alarm pheromone of most aphid species, which are preyed on by H. axyridis. (-)-beta-Caryophyllene was previously isolated from the headspace volatiles above overwintering and aggregated H. axyridis females. These sesquiterpenes elicited significant electroantennogram (EAG) activity from both H. axyridis male and female antennae. In a four-arm olfactometer, male and female H. axyridis were highly attracted toward (E)-beta-farnesene, whereas only males were attracted to (-)-beta-caryophyllene. In a bioassay technique that used a passively ventilated plastic box, both male and female H. axyridis aggregated in the (-)-beta-caryophyllene-treated side of the box. These results support the potential usefulness of (E)-beta-farnesene and (-)-beta-caryophyllene in push-pull strategies that use H. axyridis as a biological control agent in aphid-infested sites or to control this new urban pest in residential structures.

Topics: Animals; Behavior, Animal; Coleoptera; Electrophysiology; Pheromones; Polycyclic Sesquiterpenes; Sesquiterpenes

Composition of the essential oil obtained from dried flowering aerial parts of Teucrium scordium L. (Labiatae) was analyzed by GC and GC/MS. Fifty-six components were identified in the essential oil of T. scordium. The major constituents of the oil were beta-caryophyllene (22.8%), (E)-beta-farnesene (10.4%), caryophyllene oxide (8.6%), 1,8-cineole (6.1%) and beta-eudesmol (5.1%).

Topics: Chromatography, Gas; Cyclohexanols; Eucalyptol; Flowers; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Teucrium

The objective of this study was to determine harvest yield and essential oil composition of six hop cultivars ("Fredos derlingieji", "Alta", "Granit", "Marynka", "Dubskij zeleniak" and "Aromat polessja") cultivated in Lithuania. It was found that the highest crop can be obtained from early and middle harvest varieties, which mature during the first decade of September and the third decade of August. Late harvest cultivars are not suitable for cultivation, however they can be used for the development of new cultivars. Essential oils were isolated by hydrodistillation and analyzed by gas chromatography and mass spectrometry. The highest amount of essential oil was determined in Marynka cultivar (2.10 ml/100 g), the lowest one in Dubskij zeleniak 18 (0.46 ml/100 g). Totally, 62 compounds were identified in all cultivars. Myrcene, beta-caryophyllene, alpha-humulene and beta-farnesene (E) were major constituents in the essential oils. The differences in the content of other essential oil constituents were determined. Some cultivars were rich in esters and ketones.

Topics: Chromatography, Gas; Climate; Humans; Humulus; Lithuania; Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Seasons; Sesquiterpenes

To analyse chemical constituents of volatile oil from Dendranthema indicum var. aromaticum var. nov. by GC-MS.. The volatile oil was extracted from Dendranthema indicum var. aromaticum var. nov. through steam distillation and was analysed with different kinds of capillary columns to find out the optimal conditions. The content of compositions of volatile oil was determined with normalization method, and the constituents were identified by GC-MS.. 44 Components were separated and identified, which accounted for over 43% of total volatile oil.. The main constituents in the essential oils from Dendranthema indicum var. aromaticum var. nov. are Verberol, (-)zingiberene, beta-sesquiphellandrene, farnesene, transchrysanthenyl acetate, and caryophyllene.

Topics: Asteraceae; Bicyclic Monoterpenes; Flowers; Oils, Volatile; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

Induced plant responses to insect attack include the release of volatile chemicals. These volatiles are used as host-location signals by foraging parasitoids, which are natural enemies of insect herbivores. A plant's response to herbivory can be influenced by factors present in insect oral secretions. Volicitin (N-(17-hydroxylinolenoyl)-L-glutamine), identified in beet armyworm (Spodoptera exigua) oral secretions, stimulates volatile release in corn (Zea mays L.) seedlings in a manner similar to beet armyworm herbivory. Volicitin is hypothesized to trigger release of induced volatiles, at least in part, by modulating levels of the wound hormone, jasmonic acid (JA). We compare the sesquiterpene volatile release of damaged leaves treated with aqueous buffer only or with the same buffer containing volicitin or JA. Leaves were damaged by scratching with a razor and test solutions were applied to the scratched area. The leaves were either excised from the plant or left intact shortly after this treatment. Plants were treated at three different times (designated as Evening, Midnight, and Morning) and volatiles were collected in the subsequent photoperiod. JA and volicitin treatments stimulated the release of volatile sesquiterpenes, namely beta-caryophyllene, (E)-alpha-bergamotene, and (E)-beta-farnesene. In all cases, JA stimulated significant sesquiterpene release above mechanical damage alone. Volicitin induced an increase in sesquiterpene volatiles for all excised-leaf bioassays and the Midnight intact plants. Volicitin treatments in the Evening and Morning intact plants produced more sesquiterpenes than the untreated controls, while mechanical damage alone produced an intermediate response that did not differ from either treatment group. Excised leaves produced a 2.5- to 8.0-fold greater volatile response than similarly treated intact plants. Excision also altered the ratio of JA-and volicitin-induced sesquiterpene release by preferentially increasing (E)-beta-farnesene levels relative to beta-caryophyllene. The inducibility of volatile release varied with time of treatment. On average, sesquiterpene release was highest in the Midnight excised leaves and lowest in the Morning intact plants. The duration of induced volatile release also differed between treatments. On average, JA produced a sustained release of sesquiterpenes over time, with over 20% of the combined sesquiterpenes released in the third and final volatile collection period. In contrast, less

Topics: alpha-Linolenic Acid; Animals; Biological Assay; Bridged Bicyclo Compounds; Cyclopentanes; Glutamine; Host-Parasite Interactions; Oxylipins; Plant Leaves; Plants; Polycyclic Sesquiterpenes; Sesquiterpenes; Signal Transduction; Spodoptera; Time Factors; Volatilization; Zea mays