Showing papers on "Terpene published in 2003"
TL;DR: The value of Arabidopsis for studies of the biosynthesis and ecological role of terpenoids is demonstrated and new insights into their metabolism in wild-type and transgenic plants are provided.
Abstract: Volatile components, such as terpenoids, are emitted from aerial parts of plants and play a major role in the interaction between plants and their environment. Analysis of the composition and emission pattern of volatiles in the model plant Arabidopsis showed that a range of volatile components are released, primarily from flowers. Most of the volatiles detected were monoterpenes and sesquiterpenes, which in contrast to other volatiles showed a diurnal emission pattern. The active terpenoid metabolism in wild-type Arabidopsis provoked us to conduct an additional set of experiments in which transgenic Arabidopsis overexpressing two different terpene synthases were generated. Leaves of transgenic plants constitutively expressing a dual linalool/nerolidol synthase in the plastids (FaNES1) produced linalool and its glycosylated and hydroxylated derivatives. The sum of glycosylated components was in some of the transgenic lines up to 40- to 60-fold higher than the sum of the corresponding free alcohols. Surprisingly, we also detected the production and emission of nerolidol, albeit at a low level, suggesting that a small pool of its precursor farnesyl diphosphate is present in the plastids. Transgenic lines with strong transgene expression showed growth retardation, possibly as a result of the depletion of isoprenoid precursors in the plastids. In dual-choice assays with Myzus persicae, the FaNES1-expressing lines significantly repelled the aphids. Overexpression of a typical cytosolic sesquiterpene synthase resulted in the production of only trace amounts of the expected sesquiterpene, suggesting tight control of the cytosolic pool of farnesyl diphosphate, the precursor for sesquiterpenoid biosynthesis. This study further demonstrates the value of Arabidopsis for studies of the biosynthesis and ecological role of terpenoids and provides new insights into their metabolism in wild-type and transgenic plants.
526 citations
TL;DR: The major MeJA-induced volatile terpenes appear to be synthesized de novo after treatment, rather than being released from stored terPene pools, because they are almost completely absent from needle oleoresin and are the major products of terpene synthase activity measured after MeJA treatment.
Abstract: Terpenoids are characteristic constitutive and inducible defense chemicals of conifers. The biochemical regulation of terpene formation, accumulation, and release from conifer needles was studied in Norway spruce [ Picea abies L. (Karst)] saplings using methyl jasmonate (MeJA) to induce defensive responses without inflicting physical damage to terpene storage structures. MeJA treatment caused a 2-fold increase in monoterpene and sesquiterpene accumulation in needles without changes in terpene composition, much less than the 10- and 40-fold increases in monoterpenes and diterpenes, respectively, observed in wood tissue after MeJA treatment (D. Martin, D. Tholl, J. Gershenzon, J. Bohlmann [2002] Plant Physiol 129: 1003–1018). At the same time, MeJA triggered a 5-fold increase in total terpene emission from foliage, with a shift in composition to a blend dominated by oxygenated monoterpenes (e.g. linalool) and sesquiterpenes [e.g. ( E )-β-farnesene] that also included methyl salicylate. The rate of linalool emission increased more than 100-fold and that of sesquiterpenes increased more than 30-fold. Emission of these compounds followed a pronounced diurnal rhythm with the maximum amount released during the light period. The major MeJA-induced volatile terpenes appear to be synthesized de novo after treatment, rather than being released from stored terpene pools, because they are almost completely absent from needle oleoresin and are the major products of terpene synthase activity measured after MeJA treatment. Based on precedents in other species, the induced emission of terpenes from Norway spruce foliage may have ecological and physiological significance.
417 citations
TL;DR: Findings reveal that the inhibitory activity of the oil results from a complex interaction between its constituents, which produce both synergistic and antagonistic responses between the component terpenes.
Abstract: In vitro anticholinesterase activities of eight commercially available terpenoid constituents of Salvia lavandulaefolia have been investigated. These included 1,8-cineole, camphor, alpha-pinene, beta-pinene, borneol, caryophyllene oxide, linalool and bornyl acetate. Dose-dependent inhibition of acetylcholinesterase (AChE) by these chemical constituents was determined using the method of Ellman [Biochem. Pharmacol. 7 (1961) 88]. The IC50 value of 1,8-cineole was 0.06+/-0.01 mg/ml similar to that of the essential oil (0.05+/-0.01 mg/ml). Analyses of the expected inhibitions based on the prediction of a zero interactive response of a combination at its naturally occurring ratios were carried out in comparison with observed inhibition. Minor synergy was apparent in 1,8-cineole/alpha-pinene and 1,8-cineole/caryophyllene oxide combinations, with interaction indexes not exceeding 0.5. In contrast, a combination of camphor and 1,8-cineole was antagonistic with an interaction index of 2. A combination of all eight compounds was zero interactive. A combination of six constituents, excluding 1,8-cineole and camphor, was used to compare the method of expected response of a combination with a method of summation. These findings reveal that the inhibitory activity of the oil results from a complex interaction between its constituents, which produce both synergistic and antagonistic responses between the component terpenes. Understanding such interactions is important in comparing species on the basis of chemical composition.
317 citations
TL;DR: Pines produce both enantiomers of alpha-pinene, which appear to arise through antipodal reaction mechanisms by distinct enzymes, and pinene synthases, which produce mirror-image products, share only 66% amino acid identity but are similar in general properties to other monoterpene synthase of gymnosperms.
128 citations
TL;DR: This work investigated whether hop terpenoids were transformed when an ale and lager yeast were cultured in the presence of a commercially available syrup, and found that oxygenated terpenoid persisted much longer than the alkenes.
Abstract: Terpenoids are important natural flavour compounds, which are introduced to beer via hopping. It has been shown recently that yeasts are able to biotransform some monoterpene alcohols. As a first step towards examining whether yeasts are capable of altering hop terpenoids during the brewing of beer, we investigated whether they were transformed when an ale and lager yeast were cultured in the presence of a commercially available syrup. Both yeasts transformed the monoterpene alcohols geraniol and linalool. The lager yeast also produced acetate esters of geraniol and citronellol. The major terpenoids of hop oil, however, were not biotransformed. Oxygenated terpenoids persisted much longer than the alkenes.
114 citations
TL;DR: This is the first report of the presence of a range of linalool derivatives in Actinidia, including 8 from flowers that are so closely related that they are either isomers of one compound or two or more closely related compounds.
110 citations
TL;DR: Levels of bound compounds, in particular monoterpenols and C(13) norisoprenoids, increased significantly with maturation.
Abstract: Glycosidically bound volatile constituents of yellow-fleshed clingstone nectarines (cv. Springbright) were identified and quantified at three stages of maturity. Glycoconjugates were isolated by LC on a C18 reversed phase column with methanol elution followed by hydrolysis with a commercial pectinase enzyme. Forty-five bound aglycons were identified for the first time in yellow-fleshed nectarine. Thirty were terpene derivatives, and the most abundant ones were (E)- and (Z)-furan linalool oxides, linalool, α-terpineol, (E)-pyran linalool oxide, 3,7-dimethylocta-1,5-diene-3,7-diol, linalool hydrate, 8-hydroxy-6,7-dihydrolinalool, (E)- and (Z)-8-hydroxylinalools, and (E)- and (Z)-8-hydroxygeraniols. The group of C13 norisoprenoids included 3-hydroxy-β-damascone, 3-hydroxy-7,8-dihydro-β-ionone, 3-oxo-α-ionol, 3-hydroxy-7,8-dihydro-β-ionol, 3-hydroxy-β-ionone, 3-oxo-7,8-dihydro-α-ionol, 3-hydroxy-5,6-epoxy-β-ionone, 3-oxo-retro-α-ionol (isomers I and II), 3-hydroxy-7,8-dehydro-β-ionol, 4,5-dihydrovomifoliol, a...
54 citations
TL;DR: The essential oils from leaves, aerial stems and underground organs of Aristolochia argentina Gris, a medicinal plant popularly known as "charrúa", were obtained by hydrodistillation and analyzed by GC and GC/MS.
51 citations
TL;DR: The monoterpene synthase activity in males can be induced by prior treatment with juvenile hormone III (JH III) or by feeding on phloem from the host trees, Jeffrey pine ( pinus jeffreyi Grev. & Balf.) or red pine (Pinus resinosa Ait.).
Abstract: Ecological interactions of conifers and coniferophagous bark beetles are determined in part by terpenoids (isoprenoids), which are major defense metabolites of conifer oleoresin Curiously, similar compounds are important aggregation pheromones of conifer-attacking bark beetles Terpene synthases are responsible for generating the enormous variety of terpenoid carbon skeletons found in nature These catalysts convert short-chain prenyl diphosphates to a diverse assortment of hemiterpene, monoterpene, sesquiterpene, and diterpene natural products While terpene synthases have frequently been characterized from plant and microbial sources, they have not yet been described in animals Here we report the discovery of a monoterpene synthase activity in an insect, the pine engraver, Ips pini (Say) (Coleoptera: Scolytidae) Cell-free assays of I pini revealed that geranyl diphosphate (GDP) is converted to the acyclic monoterpene myrcene in whole-body extracts from males, but not females Furthermore, the monoterpene synthase activity in males can be induced by prior treatment with juvenile hormone III (JH III) or by feeding on phloem from the host trees, Jeffrey pine (Pinus jeffreyi Grev & Balf) or red pine (Pinus resinosa Ait) The sex-specificity and endocrine induction of this activity argue for its involvement in the biosynthesis of monoterpenoid pheromones mediated by enzymes from insect tissue This discovery is the first example of a monoterpene synthase in the Metazoa and evokes exciting new questions about the origin, evolution, and occurrence of terpene synthases
43 citations
TL;DR: An unusual 29-nor-3,4-seco-friedelan-4(23),20(30)-dien-3-oic acid and a new 5-hydroxy-6,9-epoxyguaiane have been isolated along with other rare terpenes and lignans from Phyllanthus oxyphyllus roots as mentioned in this paper.
38 citations
TL;DR: Generally, neither absorption nor elimination can be directly correlated with the physicochemical parameters, despite of the fact that the least absorption was observed for the most lipophilic LA.
TL;DR: Optimization of the method was accomplished on the basis of some parameters involved in the extraction, such as heating temperature and extraction time, that provided the highest peak areas, 60 degrees C and 2 min being the optimal values.
Abstract: Enantiomeric compositions of chiral terpenes in commercial fruit beverages were examined by solid phase microextraction−gas chromatography (SPME-GC). Optimization of the method was accomplished on the basis of some parameters involved in the extraction, such as heating temperature and extraction time, that provided the highest peak areas, 60 °C and 2 min being the optimal values. With the proposed method relative standard deviation (RSD) values from three replicates ranging from 2 to 12% were obtained. The enantiomeric distribution of some terpenes remained constant, whereas other terpenes (linalool, terpinen-4-ol, and α-terpineol) exhibited a considerable variation among samples. This can be indicative of the eventual addition of aromas to some fruit beverages. Keywords: Chiral; SPME; fruit beverages; terpenes; enantiomeric distribution
TL;DR: The mode of interactions of terpenes with SC were different in two solvent systems, which was showed to provide the required therapeutic plasma concentration and daily-permeated amounts of the drug.
Abstract: In this study, two terpenes with the same functional group; limonene oxide and pinene oxide were used at 5% w/v concentration in 50% v/v ethanol and 100% v/v propylene glycol (PG) to enhance the in vitro permeation of haloperidol (HP) through the human epidermis (or stratum corneum, SC). The enhancement mechanism of terpenes from both solvents was elucidated with HP-SC binding studies, Fourier transform infrared spectroscopy and differential scanning calorimetry. The enhancement activity of these terpenes was higher in 50% v/v ethanol than in 100% v/v PG. These terpenes in 50% v/v ethanol were predicted to provide the required therapeutic plasma concentration and daily-permeated amounts of the drug. Limonene oxide showed higher enhancement in both solvents, which was attributed to its less bulky structure. The terpenes in both solvents did not increase the partition of HP. Instrumental studies showed that these terpenes in 50% v/v ethanol extracted the SC lipids, disrupted the bilayer packing and partially fluidised the lipids. Limonene oxide in 100% v/v PG possibly disrupted the lipid bilayer, whilst leaving the overall bilayer structure intact and pinene oxide in the same vehicle fluidised the lipids within the ordered environment. This study showed that the mode of interactions of terpenes with SC were different in two solvent systems.
TL;DR: In this paper, the catalytic system generated in situ from [RuCl2(p-cymene]2, 1,3-bis(mesityl)imidazolinium chloride and cesium carbonate is able to perform the transformation of silylated 1,7-enynes into cyclic siloxanes.
TL;DR: The contents of the paracloacal gland secretions of the alligatorids Alligator mississippiensis, A. sinensis, Paleosuchus palpebrosus, and P. trigonatus were investigated and novel acyclic hydrocarbon terpenes with a rare trisubstituted 2,4-diene system were identified.
Abstract: The contents of the paracloacal gland secretions of the alligatorids Alligator mississippiensis, A. sinensis, Paleosuchus palpebrosus, and P. trigonatus were investigated. Novel acyclic hydrocarbon terpenes with a rare trisubstituted 2,4-diene system were identified in the secretions of A. sinensis, P. palpebrosus, and P. trigonatus. The structures of the monoterpene (2E,4E)-3,7-dimethyl-2,4-octadiene (9) and the sesquiterpene (2E,4E,7S)-3,7,11-trimethyl-2,4-dodecadiene (14) were proven by synthesis and gas chromatography on a chiral phase. Several other new terpenes (11, 16, 17, 18, 19, and 20) related to these components also were present in the secretions, as well as the known compounds myrcene (6), (E)-β-farnesene (4), (E)-β-springene (3), squalene (5), cembrene A (1), and 11,12-dihydrocembren-10-one (2).
TL;DR: In this article, the enantiomeric distribution of aroma-active compounds resulting from stereospecific biosyn-thetic pathways was established using a multidimensional chromatographic system, which involves the on-line coupling of reversed-phase liquid chromatography and gas chromatography (RPLC-GC).
Abstract: The enantiomeric distribution of aroma-active compounds resulting from stereospecific biosyn-thetic pathways was established using a multidimensional chromatographic system, which involves the on-line coupling of reversed-phase liquid chromatography and gas chromatography (RPLC-GC). The proposed approach allowed the rapid determination of the enantiomeric composition of chiral terpenes such as α-pinene, limonene, linalool and α-terpineol in different products (that is, orange aroma, orange essential oils, and fruit beverage) without requiring the previous concentration of the sample. Relative standard deviation values lower than 7.5% were obtained for the investigated compounds. Applications to the authentication of fruit products based on both the R- and S-form contents of chiral terpenes were considered.
Patent•
05 Sep 2003
TL;DR: In this article, an insect repellent for grain and dry matter containing one or more terpene compounds such as [Selection figure] was proposed. But it was not shown to have sufficient effect against cereals and dry-matter pests.
Abstract: PROBLEM TO BE SOLVED: To develop an insecticide for cereals and dry matter that has sufficient insect repellent effect against cereals and dry matter pests, is highly safe for human bodies, and can be easily used in general households. SOLUTION: An insecticide for cereals and dry matter containing one or more terpene compounds as active ingredients, terpene alcohol, terpene alcohol fatty acid ester, terpene hydrocarbon, terpene aldehyde, terpene oxide, terpene ketone An insect repellent for grain and dry matter containing one or more terpene compounds such as [Selection figure] None
TL;DR: Using selective Cr(VI) oxidations with Jones reagent and PCC, a regioselective and direct access to different oxygenated 11-nordrimane skeletons was achieved, in good overall yield, starting from naturally occurring drimane terpenes as mentioned in this paper.
Abstract: Using selective Cr(VI) oxidations with Jones reagent and PCC, a regioselective and direct access to different oxygenated 11-nordrimane skeletons was achieved, in good overall yield, starting from naturally occurring drimane terpenes.
TL;DR: In this article, three cerebrosides and two terpene glycosides from the methanol extract of the root of Aster scaber have been determined as 3-O-β-D-glucuronopyranosyl-oleanolic acid methyl ester.
Abstract: Three cerebrosides2,3, and5 and two terpene glycosides1 and4 have been isolated from the methanol extract of the root ofAster scaber. Their structures were determined as 3-O-β-D-glucuronopyranosyl-oleanolic acid methyl ester (1), (2S, 3S, 4R, 2′R, 8Z, 15′Z)-N-2′-hydroxy-15′-tetracosenoyl-1-0-β-D-glucopyranosyl-4-hydroxy-8-sphingenine (2), (2S, 3S, 4R, 8Z)-N-octadecanoyl-1-O-β-D-glucopyranosyl-4-hydroxy-8-sphingenine (3), 1 α-hydroxy-6β-O-β-D-glucosyl-eudesm-3-ene (4), and (2S, 3S, 4R, 2′R, 8Z)-N-2′-hydroxy-hexadecanoyl-1-O-β-D-glucopyranosyl-4-hydroxy-8-sphingenine (5) on the basis of spectroscopic methods.
Patent•
23 Apr 2003
TL;DR: In this article, a terpene-containing liquid composition essentially comprises a polyglycerol fatty acid ester, the terpenes and water; wherein the terpes are made solubilizable through regulating the holding temperature of the composition.
Abstract: PROBLEM TO BE SOLVED: To obtain a liquid composition containing terpenes solubilizable in high concentrations, having long-term storage stability, scarcely affected by temperature, stable over a wide temperature range, with no limitation of application range, and high in safety SOLUTION: This terpene-containing liquid composition essentially comprises a polyglycerol fatty acid ester, the terpenes and water; wherein the terpenes are made solubilizable through regulating the holding temperature of the composition COPYRIGHT: (C)2005,JPO&NCIPI
Journal Article•
TL;DR: In this paper, the effect of p-menthane monoterpene enhancers on the penetration of propranolol HCl across newborn pig skin was investigated, and it was found that the greatest penetration enhancing activity was found when the aromatic terpenes, carvacrol and thymol, were used as enhancers.
Abstract: In this study, we investigated the effect of p-menthane monoterpene enhancers on the penetration of propranolol HCl across newborn pig skin. These permeation experiments showed that hydrocarbons had mild enhancing activity when compared with terpenes with polar functional groups, such as alcohol or ketones, but that the enhancing activity was stronger than that found with terpenes with added lipophilic groups, such as trifluoroacetate. The greatest penetration enhancing activity was found when the aromatic terpenes, carvacrol and thymol, were used as enhancers. The penetration enhancing activity of hydrocarbon terpenes was not affected by either the number or the position of the double bonds. In addition, there was no significant difference between the racemate and the pure enantiomers of menthol and carvone in enhancing permeation of propranolol HCl. Retention of the model drug in the skin was also promoted by the presence of terpenes. There was no clear correlation between permeability values and skin retention of the model drug. Partitioning of propranolol HCl into the stratum comeum was increased following treatment with terpenes in 40% ethanol. The increased partitioning of the model drug was possibly due to the effect of the terpenes dissolved in ethanol rather than a direct effect of terpenes themselves. The degree of skin partitioning of propranolol HCl correlated well with the permeability values but appeared to be unrelated to the amount of skin retention.
Patent•
18 Dec 2003
TL;DR: In this article, a solution of chlorpropham (3-chlorophenyl isopropyl carbamate) containing terpenes and/or terpene oils is new.
Abstract: Solution of chlorpropham (3-chlorophenyl isopropylcarbamate) containing terpenes and/or terpene oils is new. ACTIVITY : Sprouting inhibitor. MECHANISM OF ACTION : None given.
01 Jan 2003
TL;DR: Three cerebrosides 2, 3, and 5 and two terpene glycosides 1 and 4 have been isolated from the methanol extract of the root of Aster scaber on the basis of spectroscopic methods.
Abstract: Three cerebrosides 2, 3, and 5 and two terpene glycosides 1 and 4 have been isolated from the methanol extract of the root of Aster scaber. Their structures were determined as 3-O-beta-D-glucuronopyranosyl-oleanolic acid methyl ester (1), (2S, 3S, 4R, 2'R, 8Z, 15'Z)-N-2'-hydroxy-15'-tetracosenoyl-1-O-beta-D-glucopyranosyl-4-hydroxy-8-sphingenine (2), (2S, 3S, 4R, 8Z)-N-octadecanoyl-1-O-beta-D-glucopyranosyl-4-hydroxy-8-sphingenine (3), 1alpha-hydroxy-6beta-O-beta-D-glucosyl-eudesm-3-ene (4), and (2S, 3S, 4R, 2'R, 8Z)-N-2'-hydroxy-hexadecanoyl-1-O-beta-D-glucopyranosyl-4-hydroxy-8-sphingenine (5) on the basis of spectroscopic methods.
Journal Article•
TL;DR: In this article, the aerial parts of Chrysanthemum coronarium L. were extracted with MeOH, and the extract was partitioned using EtOAc, n-BuOH and.
Abstract: The aerial parts of Chrysanthemum coronarium L. were extracted with MeOH, and the extract was partitioned using EtOAc, n-BuOH, and . The repeated column chromatography of the EtOAc and n-BuOH fractions gave two terpenes, phytol and 8-hydroxylinalol 8-O--D-glucopyranoside, identified by several spectral analyses, including NMR and MS. This paper is the first report on the isolation of these terpenes from Chrysanthemum coronarium L.
TL;DR: In this paper, a bisnor cadinane 3a, 5β-dihydroxy-4α,11-epoxybisnorcadinane 1 and the other lipid constituent methyl-11, 12, 15-trihydroxy-13(14)-octadecanoate 3 have been isolated from the leaves of Artemisia annua.
Abstract: Two new compounds, a bisnor cadinane 3a, 5β-dihydroxy-4α,11-epoxybisnor cadinane 1 and the other lipid constituent methyl-11, 12, 15-trihydroxy-13(14)-octadecanoate 3 have been isolated from the leaves of Artemisia annua.Their structures have been established on the basis of their spectral and chemical studies.
TL;DR: In this article, previously unknown esters 1b-14b were prepared by reaction of cetyl alcohol 1a, terpene alcohols 2a-6a, sterols 7a-11a, and plant phenols 12a-14a with 4,5-dichloroisothiazol-3-carboxylic acid chloride.
Abstract: Previously unknown esters 1b-14b were prepared by reaction of cetyl alcohol 1a, terpene alcohols 2a-6a, sterols 7a-11a, and plant phenols 12a-14a with 4,5-dichloroisothiazol-3-carboxylic acid chloride.
01 Jan 2003
TL;DR: In this article, natural halogenated furanones, higher terpenes and steroids comprising three relatively small groups of natural compounds were isolated mainly from sea organisms, as well as from some plant species.
Abstract: Natural halogenated furanones, higher terpenes and steroids comprising three relatively small groups of natural compounds were isolated mainly from sea organisms, as well as from some plant species. The structures of about 90 compounds are considered and the data on the biological activity of some of them are presented. Contents