Showing papers on "Terpene published in 2010"

In-vitro inhibition of human erythrocyte acetylcholinesterase by salvia lavandulaefolia essential oil and constituent terpenes.

Abstract: Sage (Salvia spp) is reputed in European herbal encyclopaedias to enhance memory, and current memory-enhancing/anti-dementia drugs are based on enhancing cholinergic activity by inhibiting cholinesterase In this study the effects of Salvia lavandulaefolia Vahl (Spanish sage) essential oil and some of its constituent terpenes on human erythrocyte acetylcholinesterase were examined in-vitro The main constituents in the essential oil batch used for analysis of cholinesterase inhibition were camphor (27%), 1,8-cineole (13%), alpha- and beta-pinene (10-15%) and bornyl acetate (10%) with other minor constituents (1% or less) including geraniol, limonene, linalool, terpineol and gamma-terpinene Using the Ellman spectrophotometric method, kinetic analysis was conducted on the interaction of the essential oil and the main monoterpenoids, camphor, 1,8-cineole and alpha-pinene IC50 values were obtained for the essential oil, 1,8-cineole and alpha-pinene and were 003 microL [corrected] mL(-1), 067 mM and 063 mM, respectively Camphor and other compounds tested (geraniol, linalool and gamma-terpinene) were less potent (camphor IC50: >10mM) The essential oil, alpha-pinene, 1,8-cineole and camphor were found to be uncompetitive reversible inhibitors These findings suggest that if the inhibitory activity of the essential oil is primarily due to the main inhibitory terpenoid constituents identified, there is a major synergistic effect among the constituents Since no single constituent tested was particularly potent, it remains to be determined whether these in-vitro cholinesterase inhibitory activities are relevant to in-vivo effects of the ingestion of S lavandulaefolia essential oil on brain acetylcholinesterase activity

Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis.

Abstract: Terpene volatiles play important roles in plant-organism interactions as attractants of pollinators or as defense compounds against herbivores. Among the most common plant volatiles are homoterpenes, which are often emitted from night-scented flowers and from aerial tissues upon herbivore attack. Homoterpene volatiles released from herbivore-damaged tissue are thought to contribute to indirect plant defense by attracting natural enemies of pests. Moreover, homoterpenes have been demonstrated to induce defensive responses in plant–plant interaction. Although early steps in the biosynthesis of homoterpenes have been elucidated, the identity of the enzyme responsible for the direct formation of these volatiles has remained unknown. Here, we demonstrate that CYP82G1 (At3g25180), a cytochrome P450 monooxygenase of the Arabidopsis CYP82 family, is responsible for the breakdown of the C20-precursor (E,E)-geranyllinalool to the insect-induced C16-homoterpene (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene (TMTT). Recombinant CYP82G1 shows narrow substrate specificity for (E,E)-geranyllinalool and its C15-analog (E)-nerolidol, which is converted to the respective C11-homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT). Homology-based modeling and substrate docking support an oxidative bond cleavage of the alcohol substrate via syn-elimination of the polar head, together with an allylic C-5 hydrogen atom. CYP82G1 is constitutively expressed in Arabidopsis stems and inflorescences and shows highly coordinated herbivore-induced expression with geranyllinalool synthase in leaves depending on the F-box protein COI-1. CYP82G1 represents a unique characterized enzyme in the plant CYP82 family with a function as a DMNT/TMTT homoterpene synthase.

Terpene synthases of oregano ( Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis

Abstract: The aroma, flavor and pharmaceutical value of cultivated oregano (Origanum vulgare L.) is a consequence of its essential oil which consists mostly of monoterpenes and sesquiterpenes. To investigate the biosynthetic pathway to oregano terpenes and its regulation, we identified and characterized seven terpene synthases, key enzymes of terpene biosynthesis, from two cultivars of O. vulgare. Heterologous expression of these enzymes showed that each forms multiple mono- or sesquiterpene products and together they are responsible for the direct production of almost all terpenes found in O. vulgare essential oil. The correlation of essential oil composition with relative and absolute terpene synthase transcript concentrations in different lines of O. vulgare demonstrated that monoterpene synthase activity is predominantly regulated on the level of transcription and that the phenolic monoterpene alcohol thymol is derived from γ-terpinene, a product of a single monoterpene synthase. The combination of heterologously-expressed terpene synthases for in vitro assays resulted in blends of mono- and sesquiterpene products that strongly resemble those found in vivo, indicating that terpene synthase expression levels directly control the composition of the essential oil. These results will facilitate metabolic engineering and directed breeding of O. vulgare cultivars with higher quantity of essential oil and improved oil composition.

Naturally Occurring Triterpenoid Saponins

Abstract: Naturally occurring new triterpenoid saponins reported from mid-1996 to March, 2007 are reviewed including their physical constants and plant sources, and are compiled in Table 1. New saponins are arranged in Table 1 on the basis of the skeletal structures of their aglycones, e.g., oleanane type, ursane type, lupane type, hopane type, taraxastane type, cycloartane type, lanostane type, tirucallane type, dammarane type, cucurbitane type, and holostane type. The known triterpenoid saponins and prosapogenins of the new saponins, the biological and pharmacological activities of which were published during 1996-2007, are also reviewed together with their plant sources listed in Table 2 according to the skeletal structures of their aglycones in the same fashion as in Table 1. The plant and animal sources of both new and known bioactive triterpenoid saponins are collected in Table 3 in alphabetical order. The biological and pharmacological activities such as antiallergic, antiatherosclerosis and antiplatelet, antibacterial, anticomplementary, antidiabetic, contraceptive, antifungal, anti-inflammatory, antileishmanial, antimalarial/antiplasmodial, anti-obesity, anti-proliferative, antipsoriatic, antispasmodic, antisweet, antiviral, cytotoxic/antitumor, detoxication, gastroprotective, haemolytic, hepatoprotective, immunomodulatory, anti-enzyme, anti-osteoporotic, insecticidal, insulin-like, membrane-porosity, molluscicidal, neuropharmacological, anti-endothelial dysfunction, snake venom antidote, and sweet activities of these saponins or derived prosapogenins are discussed briefly after Table 3.

Catabolism of citronellol and related acyclic terpenoids in pseudomonads.

Abstract: Terpenes are a huge group of natural compounds characterised by their predominantly pleasant smell. They are built up by isoprene units in cyclic or acyclic form and can be functionalised by carbonyl, hydroxyl or carboxyl groups and by presence of additional carbon–carbon double bonds (terpenoids). Currently, much more than 10,000 terpenoid compounds are known, and many thereof are present in different iso- and stereoforms. Terpenoids are secondary metabolites and can have important biological functions in living organisms. In many cases, the biological functions of terpenoids are not known at all. Nevertheless, terpenoids are used in large quantities as perfumes and aroma compounds for food additives. Terpenoids can be also precursors and building blocks for synthesis of complex chiral compounds in chemical and pharmaceutical industry. Unfortunately, only few terpenoids are available in large quantities at reasonable costs. Therefore, characterisation of suited biocatalysts specific for terpenoid compounds and development of biotransformation processes of abundant terpenoids to commercially interesting derivates becomes more and more important. This minireview summarises knowledge on catabolic pathways and biotransformations of acyclic monoterpenes that have received only little attention. Terpenoids with 20 or more carbon atoms are not a subject of this study.

Characterisation of an (S)-linalool synthase from kiwifruit (Actinidia arguta) that catalyses the first committed step in the production of floral lilac compounds

Abstract: Kiwifruit (Actinidia spp. Lindl.) flowers and fruit contain many compounds of interest to the flavour and fragrance industries. In particular, Actinidia arguta (Sieb. et Zucc.) Planch. ex Miq. flowers produce β-linalool and important derivatives thereof, including linalool oxides, lilac aldehydes, alcohols and alcohol epoxides. Dynamic headspace sampling of whole A. arguta flowers showed that the peak emission rate of linalool, lilac alcohols and lilac aldehydes occurred around 0800 hours. After solvent extraction, linalool levels remained constant throughout the day and night, but lilac alcohol levels peaked at noon. In whole flowers, linalool was found predominantly in pistils and petals, and the lilac compounds were found mainly in petals. Two highly homologous (96.6% nucleotide identity) terpene synthase cDNA sequences, AaLS1 and ApLS1, were isolated from A. arguta and Actinidia polygama (Sieb. et Zucc.) Maxim flower EST libraries respectively. Real-time PCR analysis revealed that AaLS1 was expressed constitutively throughout the day and night, and primarily in petal tissue. Functional analysis in Escherichia coli showed that AaLS1 and ApLS1 each encoded a linalool synthase which was confirmed by transient expression in planta. Enantioselective gas chromatography revealed that both terpene synthases produced only (S)-(+)-linalool. AaLS1, therefore, is likely to be the key enzyme producing the (S)-linalool precursor of the lilac alcohols and aldehydes in A. arguta flowers.

Antibacterial Activities Against Staphylococcus aureus of Terpene Alcohols With Aliphatic Carbon Chains

Abstract: The antibacterial activities against Staphylococcus aureus of terpene alcohols with aliphatic carbon chains of various lengths were investigated. Farnesol and nerolidol, which each contain two isoprene units, had the strongest antibacterial activities and damaging effects on cell membranes of all the terpene alcohols tested. Plaunotol, which is a diterpene, had antibacterial activity similar to that of sesquiterpenes. The relationship between the length of the carbon chain bonded to the hydroxyl group and activity suggests that the length of the carbon chain is an important determinant of antibacterial activity and cell membrane-damaging activity. It was concluded that the carbon chain length of C10-C12 was appropriate to show the activity.

Terpenoids from Salvia trijuga.

Abstract: Nine new germacrane sesquiterpenes, trijugins A-I (1-9), a new lupane triterpenoid, 3 alpha-O-acetyl-20(29)-lupen-2 alpha-ol (10), and 24 known terpenoids were isolated from Salvia trijuga. The structure of compound I was confirmed by single-crystal X-ray diffraction. Compounds 1-10 and 32 were evaluated for their cylotoxicity against live human tumor cell lines. Compounds 9 and 32 exhibited moderate toxicity effects against several cell lines.

PQQ-dependent alcohol dehydrogenase (QEDH) of Pseudomonas aeruginosa is involved in catabolism of acyclic terpenes.

Abstract: Growth of Pseudomonas aeruginosa on acyclic terpene alcohols such as geraniol depends on the presence of the atuRABCDEFGH gene cluster and a functional acyclic terpene utilisation (Atu) pathway. The proteins encoded by the atu gene cluster are necessary but not sufficient for growth on acyclic terpenes. Comparative 2-dimensional polyacrylamide gel electrophoresis of soluble P. aeruginosa proteins revealed the presence of an additional spot (besides Atu proteins) that is specifically expressed in geraniol cells but is absent in isovalerate-grown cells. The spot was identified as PA1982 gene product a pyrroloquinoline quinone (PQQ) dependent ethanol oxidoreductase (QEDH). Inactivation of PA1982 by insertion mutagenesis resulted in inability of the mutant to utilise ethanol and in reduced growth on geraniol. Growth on ethanol was restored by transferring an intact copy of the PA1982 gene into the mutant. The PA1982 gene product was purified from recombinant Escherichia coli and revealed PQQ-dependent oxidoreductase activity with a variety of substrates including acyclic terpene derivates at comparable V(max)-values. Our results show that QEDH participates in oxidation of acyclic terpene derivates in addition to the well-known function in ethanol metabolism.

Foliar mono- and sesquiterpene contents in relation to leaf economic spectrum in native and alien species in Oahu (Hawai'i).

Abstract: Capacity for terpene production may confer advantage in protection against abiotic stresses such as heat and drought, and also against herbivore and pathogen attack. Plant invasive success has been intense in the Hawaiian islands, but little is known about terpene content in native and alien plant species on these islands. We conducted a screening of leaf terpene concentrations in 35 native and 38 alien dominant plant species on Oahu island. Ten (29%) of the 35 native species and 15 (39%) of the 38 alien species contained terpenes in the leaves. This is the first report of terpene content for the ten native species, and for 10 of the 15 alien species. A total of 156 different terpenes (54 monoterpenes and 102 sesquiterpenes) were detected. Terpene content had no phylogenetic significance among the studied species. Alien species contained significantly more terpenes in leaves (average+/-SE=1965+/-367 microg g(-1)) than native species (830+/-227 microg g(-1)). Alien species showed significantly higher photosynthetic capacity, N content, and lower Leaf Mass Area (LMA) than native species, and showed higher total terpene leaf content per N and P leaf content. Alien species, thus, did not follow the expected pattern of "excess carbon" in comparison with native species. Instead, patterns were consistent with the "nutrient driven synthesis" hypothesis. Comparing alien and native species, the results also support the modified Evolution of Increased Competitive Ability (EICA) hypothesis that suggests that alien success may be favored by a defense system based on an increase in concentrations of less costly defenses (terpenes) against generalist herbivores.

Mechanism of atmospheric ozonolysis of sabinene: A DFT study

Abstract: Terpenes, which are important constituents of biogenic nonmethane organic compounds (NMOCs) in the atmosphere, play an important role in the tropospheric chemistry because of their large emission rates and their strong reactivity. The most important terpenes are α -pinene, β -pinene, sabinene and d -limonene, accounting for 40–80% of the overall terpene emissions on a global scale. The atmospheric chemistry of terpenes has not been fully understood due to the short-lifetime of their oxidized radical intermediates, and the extreme difficulty in the detection of these species experimentally. In this paper, we carried out molecular orbital theory calculations for the atmospheric ozonolysis of sabinene. The profile of the potential energy surface was constructed. The calculated results were compared with the available experimental observations. Several experimentally uncertain compounds were determined. The theoretical study shows that the dominant products of the atmospheric ozonolysis of sabinene are sabinaketone, formaldehyde and formic acid. Sabinaketone is a low vapor pressure compounds and is inclined to form secondary organic aerosols (SOAs). An energetically favorable formation pathway for 3-oxo-sabina ketone is revealed for the first time.

Quantitative High Performance Liquid Chromatographic Analysis of Simple Terpenes, Carotenoids, Phytosterols and Flavonoids in the Leaves of Acalypha wilkesiana Muell Arg.

Abstract: The simple terpenes, carotenoids, phytosterols, and flavonoids compositions of the leaves of Acalypha wilkesiana were determined by high performance liquid chromatography (HPLC). The leaves were rich in flavonoids (about 251.3mg/kg dry weight), carotenoids (76.3mg/kg dry weight), and phytosterols (16.6mg/kg dry weight), but very low in simple terpenes (0.0084mg/kg dry weight). Three flavonoids (artemetin, luteolin, and vitexicarpin) were detected, with luteolin (about 35.85% of the flavonoid extract), having the highest concentration. Five carotenoids were detected, with carotene (56.76%), and lutein (21.80%) having the highest concentrations. Of the six phytosterols detected, the levels of stigmasterol (37.55%) and β-sitosterol (24.80%) were the highest. Myrcene (2.99%), β-amyrin (2.96%), lupeol (2.50%) and thujene (2.44%) were the highest amongst the twelve simple terpenes detected. These results indicate that the leaves are potential sources of allelochemicals and nutraceuticals, and in addition, justify their use in traditional medicine.

Stability assessment of gas mixtures containing terpenes at nominal 5 nmol/mol contained in treated aluminum gas cylinders

Abstract: Studies of climate change increasingly recognize the diverse influences exerted by terpenes in the atmosphere, including roles in particulates, ozone formation, and their oxidizing potential. Measurements of key terpenes suggest atmospheric concentrations ranging from low pmol/mol (parts per trillion) to nmol/mol (parts per billion), depending on location and compound. To accurately establish concentration trends, assess the role of terpenes in atmospheric chemistry, and relate measurement records from many laboratories and researchers, it is essential to have good calibration standards. The feasibility of preparing well-characterized, stable gas cylinder standards for terpenes at the nmol/mol level is not yet well established. Several of the world’s National Metrology Institutes (NMIs) are researching the feasibility of developing primary and secondary reference gas standards at the nmol/mol level for terpenes. The US NMI, the National Institute of Standards and Technology, has prepared several nmol/mol mixtures, in treated aluminum gas cylinders, containing terpenes in dry nitrogen at nominal 5 nmol/mol for stability studies. Overall, 11 terpenes were studied for stability. An initial gas mixture containing nine terpenes, one oxygenate, and six aromatic compounds, including benzene as an internal standard, was prepared. Results for four of the nine terpenes in this initial mixture indicate stability in these treated aluminum gas cylinders for over 6 months and project long term (years) stability. Interesting results were seen for β-pinene, which when using a linear equation rate decline predicts that it will reach a zero concentration level at day 416. At the same time, increases in α-pinene, d-limonene (R-(+)-limonene), and p-cymene were observed, including camphene, a terpene not prepared in the gas mixture, indicating a chemical transformation of β-pinene to these species. Additional mixtures containing combination of either α-pinene, camphor, α-terpinene, and benzene indicate a second-order quadratic rate decline for the α-pinene and α-terpinene, a linear rate decline for camphor, and a second-order quadratic rate increase of camphene.

Antimicrobial activity of constituents identified in essential oils from mentha and cinnamomum through gc-ms

Abstract: GS/MS of essential oils from Cinnamomum camphorum and Mentha piperita revealed the main chemical components, bornyl acetate, terpinen�4�ol, 1,8 cineole, camphor, eugenol, limonene, ά� pinene, β pinene, geraniol, cinnamaldehyde, linalool, borneol and menthol.GCMS studies of the essential oils of Mentha piperita and Cinnamomum camphorum have revealed the major constituents as menthol and camphor respectively as per the retention time (area 30.07% ,mol.wt. 156.26 for menthol and 67.66% area, mol.wt.142 for camphor). Two terpenoids were subjected for the study of their antimicrobial activity against E.coli and S.aureus. Menthol showed greater zone of inhibition in 24 hrs. at maximum 2% concentration , while less zone of inhibition in 24 hrs. was observed at 2% concentration with camphor.Structure - activity relationship has been observed in the following trend. Methoxy terpene > Alcoholic Terpene > Ketonic terpene On the basis of the above observation these terpenes can be used as natural medicines in the treatment of several diseases like cold & Flu, infectious diseases, bronchitis and also as flavouring liquors, cosmetics, fragrances etc.

Production of terpenes and terpenoids in glandular trichome-bearing plants

Abstract: Methods for producing heterologous terpenes, terpenoids and/or small molecules in transgenic glandular trichome-bearing plants are provided, as well as the transgenic glandular trichome-bearing plants capable of producing the heterologous terpenes, terpenoids and small molecules. The genetically engineered glandular trichome-bearing plants contain and express one or more genes which encode proteins active in the biosynthetic pathways which produce the terpenes, terpenoids and small molecules. As a result, the essential oil of the transgenic plant is enriched for the heterologous or homologous terpenes, terpenoids and/or small molecules Storage of the essential oil in the glandular trichomes of the plant reduces the volatility and cytotoxic capacity of the heterologous molecules, thereby increasing yield and decreasing damage to the transgenic plant.

Insight into C35 terpene Biosyntheses by Nonpathogenic Mycobacterium Species: Functional Analyses of Three Z-Prenyltransferases and Identification of Dehydroheptaprenylcyclines

Abstract: Nonpathogenic Mycobacterium species produce rare cyclic C(35) terpenes that are biosynthesized by cyclization of Z-type C(35) polyprenyl diphosphate. To provide deeper insight into the biosynthesis of C(35) terpenes, we carried out functional analyses of three Z-prenyltransferase homologues in M. vanbaalenii identified by genomic analysis. Mvan_3822, a novel bifunctional Z-prenyltransferase, biosynthesizes C(35)-heptaprenyl diphosphate as a main product from (E,E)-farnesyl diphosphate (E,E-FPP) and (E,E,E)-geranylgeranyl diphosphate (E,E,E-GGPP), but produces a C(50)-decaprenyl diphosphate from geranyl diphosphate. Mvan_1705 is a novel Z,E,E-GGPP synthase. In addition, novel cyclic C(35) terpenes, (14E)- and (14Z)-dehydroheptaprenylcycline, were identified as minor metabolites in nonpathogenic Mycobacterium cells. C(35) terpenes could be biosynthesized by two routes, in which E and Z geometric isomers of heptaprenyl diphosphate are produced from E,E-FPP and E,E,E-GGPP, and the prenylreductase responsible for the biosynthesis of C(35) terpenes could reduce both E and Z prenyl residues.

Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry.

Abstract: Starting from solid wastes from two-phase olive-oil extraction, the pentacyclic triterpenes oleanolic acid and maslinic acid were isolated. These natural compounds were transformed into methyl olean-12-en-28-oate (5), which then was transformed into several seco-C-ring triterpene compounds by chemical and photolytic modifications. The triene seco-products were fragmented through several oxidative procedures to produce, simultaneously, cis- and trans-decalin derivatives, both potential synthons for bioactive compounds. The chemical behavior of the isolated fragments was investigated, and a suitable approach to several low-molecular-weight terpenes was performed. These are interesting processes for the value-addition to solid waste from the olive-oil industry.

Biofuel production in prokaryotes and eukaryotes

Abstract: Terpene synthases are enzymes that directly convert IPP & DMAPP to terpenes, such as fusicoccadiene. Described herein are methods and compositions for the production of terpenes and terpenoids for use as fuel molecules or other useful components. Genetically engineered enzymes capable of producing terpenes and terpenoids are also described.

Methods of Blocking Ultraviolet Radiation and Promoting Skin Growth Using Terpenes and Terpenoids

Abstract: The present invention provides methods of treating humans and animals with terpenes and terpenoids in order to rejuvenate the skin and increase the protective layer against irradiation by ultraviolet radiation (UVR). More specifically it provides terpenes and terpenoids as ingredients that work as persistent UVR blockers. Terpenes and terpenoid compounds support the growth of skin, skin tissue and keratinocytes and additional UVR-blocking by reason of increased stratum corneum thickness and loricrin content. Both terpenes and terpenoids may be applied topically or orally at oral or topical concentrations from about 6 mg to about 600 mg per kilogram of body weight per day effective to stimulate growth of the skin layer and prevent damage from ultraviolet radiation (UVR).

Phenolic Compounds and Terpenes in the Green Parts of Glycine Hispida

Abstract: A study was conducted to determine the phenolic compounds and terpenes in the chloroform and water extracts of the green parts of Glycine hispida collected during the flowering stage. The organoleptic and physico-chemical parameters were defined. The phenolic and terpenoied component of chloroform and water extracts was studied using gas-chromatograph/mass spectrometer (Hewlett Packard HP-6890) with a mass-selective detector (HP-5972). The results showed that, chloroform and water extracts from the green parts of the Glycine hispida were 2.69 and 32.12% of the mass, respectively. The Gc/Mass analysis of the samples revealed that, the chloroform extract had components that are belong to terpenes, including megastigmatrienone I, phytol, isophytol and alpha-pinene. Megastigmatrienone I, is the one of the main components of the terpenes that has been found. The quantitative content of Megastigmatrienone I is 84.19 mg/kg. Megastigmatrienone I, has a specific tobacco-like odor and is the one of the main odor components of the chloroform extract. Pyrogallol and phenolic acids were found in the water extract of the green parts of Glycine hispida, .The phenolic acids in this water extract were ; isovanillic and salicylic acids (benzoic acid derivatives), and ferulic and m-coumaric acid (cinnamic acid derivatives). Salicylic acid has the greatest quantitative content in the water extract (71.43) mg/kg. The greatest quantitative content of the cinnamic acid derivatives is ferulic acid (77.9) mg/kg.

Method for synthesizing gallic acid terpene alcohol ester with auxiliary supersonic wave

Abstract: The invention discloses a method for ultrasound-assisted synthesis of gallic acid, terpene alcohol ester, comprising the following steps that compounds of a 3,4,5-triacetyl gallic acid and terpene alcohols are subjected to dehydration and esterification in acetonitrile through DCC(N,N'-dicyclohexylcarbodiimide) under conditions of ultrasound and room temperature to generate the 3,4,5-triacetyl gallic acid, terpene alcohol ester; and the 3,4,5-triacetyl gallic acid, terpene alcohol ester is subjected to deacetylation of hydrazine hydrate under the condition of room temperature to generate the gallic acid, terpene alcohol ester. The synthesis method has the advantages of low reaction temperature, short reaction time and easy separation of the product.

Increasing the concentration of terpene compounds in liquids

Abstract: A method for increasing the concentration of terpene compounds in liquids, especially beverages, comprises adding a flavor compound more polar than the terpene compound to the latter and forming a microemulsion in the presence of a surfactant.