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At least 19 recordsLinked to original sources
PubMed2005

Hemiterpene glucosides with anti-platelet aggregation activities from Ilex pubescens.

Two new hemiterpene glucosides named pubescenosides A and B were isolated from the root of Ilex pubescens. Their structures were elucidated on the basis of spectroscopic and chemical evidence as 2-(trans-caffeoyloxy)methyl-3-hydroxy-1-butene-4-O-beta-D-glucopyranoside and 2-hydroxymethyl-3-caffeoyloxy-1-butene-4-O-beta-D-glucopyranoside, respectively. Pharmacological investigation on pubescenosides A and B indicated that both possess potent anti-platelet aggregation activities.

Animals↗
PubMed2001

Hymenosides A-F, six new hemiterpene glucosides from the Japanese fern Hymenophyllum barbatum.

In the course of investigation of the bitter-tasting substances of the Japanese fern Hymenophyllum barbatum belonging to the family Hymenophyllaceae, six new hemiterpene glucosides called hymenosides A-F (1-6) have been isolated from the methanol extract, together with an acyclic bis-bibenzyl derivative, perrottetin H. This paper deals with the structure elucidation of the newly isolated glucosides.

Carbohydrate Conformation↗
PubMed2006

A hemiterpene glucoside as a probing deterrent of the bean aphid, Megoura crassicauda, from a non-host vetch, Vicia hirsuta.

The bean aphid, Megoura crassicauda Mordvilko, feeds selectively on plants belonging to the genus Vicia (Fabaceae). However, it never infests the tiny vetch, V. hirsuta (L.) Gray. The aphid appeared to discriminate between host and non-host plants by tasting specific chemicals during penetration of its stylet into the plant tissues. The aphid, after being stimulated by specific probing stimulants, deposited characteristic proteinous stylet sheaths through a parafilm membrane, which has one side in contact with an extract solution of Vicia angustifolia. However, an addition of a V. hirsuta extract to the medium strongly inhibited the salivary sheath formation. A specific probing deterrent was isolated from a V. hirsuta extract by monitoring the inhibitory effect, and identified as (E)-2-methyl-2-butene-1,4-diol 4-O-beta-d-glucopyranoside. A mixture of the glycoside and the stimulatory V. angustifolia fraction in the same equivalency found in plants significantly decreased the probing activity in M. crassicauda. Since the stylet insertion process is a crucial step for the aphid's settlement on a plant, the glycoside seems to act as an effective chemical barrier for V. hirsuta.

Animals↗
PubMed2001

New bitter-tasting hemiterpene glycosides from the Japanese fern Hymenophyllum barbatum.

Hymenosides G--J were newly isolated from the Japanese fern Hymenophyllum barbatum, in addition to hymenosides A--F. The structures of hymenosides were elucidated by extensive two-dimensional nuclear magnetic resonance and/or chemical evidence. The structures of those aglycones were divided into three types, 1,4-dihydroxy-2-hydroxymethyl-but-2-ene, 1,4-dihydroxy-2-methyl-but-2-ene, and 3-hydroxy-5-hexanolide. The sugar moieties were also established by chemical and spectroscopic methods, which were acylated by phenylacetic acid derivatives. These glycosides had a bitter or weakly pungent taste.

Acetylation↗
PubMed2001

Biosynthesis of 2-methyl-3-buten-2-ol emitted from needles of Pinus ponderosa via the non-mevalonate DOXP/MEP pathway of isoprenoid formation.

The volatile hemiterpene 2-methyl-3-buten-2-ol (MBO) is emitted from the needles of several pine species from the Western United States and contributes to ozone formation in the atmosphere. It is synthesised enzymatically from dimethylallyl diphosphate (DMAPP). We show here that needles of Pinus ponderosa Laws. incorporated [1-2H1]-1-deoxy-D-xylulose (d-DOX) into the emitted MBO, but not D,L-[2-13C]mevalonic acid lactone. Furthermore, MBO emission was inhibited by fosmidomycin, a specific inhibitor of the second enzyme of the mevalonate-independent pathway of isopentenyl diphosphate and DMAPP formation, i.e. the 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) pathway. We thus prove that MBO emitted from needles of P. ponderosa is primarily formed via the DOXP/MEP pathway.

Hemiterpenes↗
PubMed2005

The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers.

Terpenoids, the largest class of plant secondary metabolites, play essential roles in both plant and human life. In higher plants, the five-carbon building blocks of all terpenoids, isopentenyl diphosphate (IPP) and dimethylallyl diphosphate, are derived from two independent pathways localized in different cellular compartments. The methylerythritol phosphate (MEP or nonmevalonate) pathway, localized in the plastids, is thought to provide IPP and dimethylallyl diphosphate for hemiterpene, monoterpene, and diterpene biosynthesis, whereas the cytosol-localized mevalonate pathway provides C5 units for sesquiterpene biosynthesis. Stable isotope-labeled, pathway-specific precursors (1-deoxy-[5,5-2H2]-D-xylulose and [2,2-2H2]-mevalolactone) were supplied to cut snapdragon flowers, which emit both monoterpenes and the sesquiterpene, nerolidol. We show that only one of the two pathways, the plastid-localized MEP pathway, is active in the formation of volatile terpenes. The MEP pathway provides IPP precursors for both plastidial monoterpene and cytosolic sesquiterpene biosynthesis in the epidermis of snapdragon petals. The trafficking of IPP occurs unidirectionally from the plastids to cytosol. The MEP pathway operates in a rhythmic manner controlled by the circadian clock, which determines the rhythmicity of terpenoid emission.

Antirrhinum↗
PubMed2003

Repeated exposure to isoprene oxidation products causes enhanced respiratory tract effects in multiple murine strains.

Ozone reacts with terpenes, common hydrocarbons in cleaning and consumer products as well as the ambient environment, to form particle- and gas-phase products; these have been shown to cause sensory irritation and airflow limitation in mice during single exposures. Isoprene, a hemiterpene emitted from both plants and animals as a bioeffluent, induces the largest effects. This study evaluated the effects of repeated exposures to isoprene oxidation products (OPs) on airway irritation, airflow limitation, and airway responsiveness. A secondary objective was to evaluate a genetic influence by examining multiple murine strains. Six strains (A/J, AKR/J, BALB/c, Swiss Webster, C57Bl/6, and C3H/HeN; total n = 35) were exposed to isoprene oxidation products (1080 +/- 155 ppb isoprene + 3227 +/- 157 ppb ozone at admixing) for 3 h/day for 4 consecutive days. Respiratory parameters were monitored on days 1 and 4 via head-out plethysmography, and airway responsiveness to aerosolized methacholine was evaluated 24 h before the first exposure and immediately after the fourth exposure. Sensory irritation was observed during exposure, as evidenced by a reduction in respiratory frequency (f). A reduction in peak expiratory flow normalized for tidal volume (PEF/VT) also occurred, indicating an airflow limitation effect. Marked enhancement of the effects on f and PEF/VT was observed with repeated exposures, suggesting a cumulative effect. Frequency was reduced from 46.0 +/- 2.3% of baseline during exposure 1 to 34.2 +/- 2.1% during exposure 4 (p =.00002; pooled values for all strains). Similarly, PEF/VT decreased from 75.6 +/- 3.9% of baseline during exposure 1 to 53.1 +/- 3.7% during exposure 4 (p <.00001). A significant reduction in airway responsiveness was observed following repeated exposures in most strains. Interstrain differences in responses were noted, indicating a genetic component. These findings have important implications for indoor environments, where isoprene concentrations can be high in buildings with high occupant densities. The findings are also relevant to outdoor environments, where isoprene emissions from vegetation lead to the formation of isoprene OPs, which may partition onto existing particulate matter (PM) in the atmosphere to contribute to secondary organic aerosol. Further, the genetic variability observed in the mouse strains examined suggests that interindividual differences in response may also exist in human populations, which may help to explain the high variability in symptom reporting in indoor environments.

Animals↗
PubMed2003

A novel sex-specific and inducible monoterpene synthase activity associated with a pine bark beetle, the pine engraver, Ips pini.

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.

Animals↗
PubMed2003

Volatile compounds from leaf-buds of Populus nigra L (Salicaceae).

Volatile components from fresh and air-dried leaf-buds of Populus nigra L. (Salicaceae) were isolated by Likens-Nickerson apparatus and analyzed using GC/MS. Forty-eight components (ca. 95% of the total isolate) were identified among black poplar bud volatiles. Sesquiterpene alcohols beta-eudesmol and alpha-eudesmol represented 26.3-28.7% of the oil. Other major sesquiterpene compounds were gamma-selinene (7.6-8.8%), delta-cadinene (7.8-8.6%), alpha-elemene (3.3-5.2%) and gamma-cadinene (3.9-4.2%). Hemiterpenes were also identified (2.2-7.6%). Monoterpenes were present in low percentages (1.6-5.7%). Aliphatic and aromatic alcohols, carbonyl compounds and aliphatic acids were identified among non-terpene volatiles (9.8-13.5%). The fresh buds contained 0.27% and dried 0.12% essential oil. Air-drying moderately effected the volatiles qualitative and quantitative composition.

Gas Chromatography-Mass Spectrometry↗
PubMed2002

New glycosides from the Japanese fern Hymenophyllum barbatum.

Thirteen glycosides and methyl (3R,5R)-5-hydroxy-(beta-D-glucopyranosyloxy)-hexanoate were newly isolated from the Japanese fern Hymenophyllum barbatum, although our previous work revealed the isolation of hemiterpene glycosides, hymenosides A-J, from the same species. The structures of the newly isolated glycosides were elucidated by extensive two-dimensional (2D) NMR and/or chemical evidence. The structures of those aglycones were divided into four types, 2-methyl-but-2-ene-1,4-diol, 2-hydroxymethyl-but-2-ene-1,4-diol, 2-methylene-butane-1,3,4-triol, and 3-hydroxy-5-hexanolide. The sugar moieties, which were acylated by phenylacetic acid derivatives, were also established by chemical and spectroscopic methods. Eight glucosides of the isolated compounds in the present investigation had a bitter or weakly pungent taste. It is clear that a phenylacetyl group attached to glucose or allose as an ester is necessary for the bitter taste.

Chromatography, Gel↗
PubMed1997

Detection of isoprene in expired air from human subjects using proton-transfer-reaction mass spectrometry.

A new analytical method using proton-transfer-reaction mass spectrometry (PTRMS) is described for the determination of trace constituents in human breath. PTRMS is sufficiently sensitive and specific that it does not require preconcentration or separation. At its present stage of development it is capable of detecting trace constituents present in air at the part-per-billion level. These capabilities are illustrated for isoprene, one of the most abundant endogenous hydrocarbons. Our results confirm recent observations of a diurnal level variation associated with sleep or wakefulness; a new finding is that young children have much lower levels of isoprene in breath than adults. To address the metabolic origin of human isoprene, we used PTRMS to analyze expired air for allylic C5 alcohols that have been proposed to be non-enzymatic precursors of isoprene. The lack of correlation between peak breath isoprene and these alcohols suggests that the hydrocarbon is formed by some other mechanism.

Adult↗
PubMed1999

Deconvolution gas chromatography/mass spectrometry of urinary organic acids--potential for pattern recognition and automated identification of metabolic disorders.

The National Institute of Standards and Technology (NIST) Automated Mass Spectral Deconvolution and Identification System (AMDIS) is applied to a selection of data files obtained from the gas chromatography/mass spectrometry (GC/MS) analysis of urinary organic acids. Mass spectra obtained after deconvolution are compared with a special user library containing both the mass spectra and retention indices of ethoxime-trimethylsilyl (EO-TMS) derivatives of a set of organic acids. Efficient identification of components is achieved and the potential of the procedure for automated diagnosis of inborn errors of metabolism and for related research is demonstrated.

Acyl-CoA Dehydrogenase↗
PubMed1999

Quantification of breath isoprene using the selected ion flow tube mass spectrometric analytical method.

We have used our selected ion flow tube mass spectrometric method (SIFT-MS) to study isoprene levels in the alveolar breath of 29 healthy volunteers during normal working hours at the varying states of nutrition occurring during this period. Quantification of the breath isoprene was achieved using O(2)(+) precursor ions to avoid complications which can arise when using H(3)O(+) precursor ions for isoprene analysis. The present data indicate that the spread of the alveolar isoprene levels in this sample of healthy individuals is 22 to 234 ppb and that the mean value is 83 ppb with a standard deviation of 45 ppb. These levels are compared with those previously determined using other techniques and are seen to be at the low end of the values previously reported. The present studies are a prelude to an investigation of the proposed correlation of breath isoprene levels with psychological, physical and biochemical stress.

Adult↗
PubMed1999

Engineered isoprenoid pathway enhances astaxanthin production in Escherichia coli.

The isoprenoid pathway is a versatile biosynthetic network leading to over 23,000 compounds. Similar to other biosynthetic pathways, the production of isoprenoids in microorganisms is controlled by the supply of precursors, among other factors. To engineer a host that has the capability to supply geranylgeranyl diphosphate (GGPP), a common precursor of isoprenoids, we cloned and overexpressed isopentenyl diphosphate (IPP) isomerase (encoded by idi) from Escherichia coli and GGPP synthase (encoded by gps) from the archaebacterium Archaeoglobus fulgidus. The latter was shown to be a multifunctional enzyme converting dimethylallyl diphosphate (DMAPP) to GGPP. These two genes and the gene cluster (crtBIYZW) of the marine bacterium Agrobacterium aurantiacum were introduced into E. coli to produce astaxanthin, an orange pigment and antioxidant. This metabolically engineered strain produces astaxanthin 50 times higher than values reported before. To determine the rate-controlling steps in GGPP production, the IDI-GPS pathway was compared with another construct containing idi, ispA (encoding farnesyl diphosphate (FPP) synthase in E. coli), and crtE (encoding GGPP synthase from Erwinia uredovora). Results show that the conversion from FPP to GGPP is the first bottleneck, followed sequentially by IPP isomerization and FPP synthesis. Removal of these bottlenecks results in an E. coli strain providing sufficient precursors for in vivo synthesis of isoprenoids.

Alkyl and Aryl Transferases↗
PubMed2000

Odorant molecular length: one aspect of the olfactory code.

Organic acid odorants of differing carbon number produce systematically different spatial patterns of [(14)C]2-deoxyglucose uptake in the glomerular layer of the olfactory bulb. Because increasing carbon number correlates with progressive increases in several molecular features, including hydrophobicity, length, and volume, we determined which of these properties was most associated with systematic changes in the location of an anterior, dorsomedial module responding to fatty acids. We exposed groups of rats to two series of organic acids that each had the same number of carbons, but differed in their hydrocarbon structures. These straight-chained, branched, cyclic, and double-bonded molecules differed independently in hydrophobicity, length, and volume. The only molecular property that was strongly correlated with the location of the module was molecular length, suggesting that this molecular feature is the principal determinant of the chemotopic organization of glomeruli within the module. We also found that distinct hydrocarbon structures produced large differences in spatial patterns of 2-deoxyglucose uptake in posterior parts of the bulb. Even subtly distinct structural isomers evoked posterior responses that differed greatly. The odorant 2-methylbutyric acid evoked much greater uptake in the posterior bulb than did its structural isomer 3-methylbutyric acid (isovaleric acid). These data suggest that posterior portions of the bulb may encode specific steric features of odorant molecules and that some odorant features may have an inherent or acquired greater representation than do others.

Animals↗