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At least 19 recordsLinked to original sources
PubMed2005

Traceability of Asiago mountain cheese: a rapid, low-cost analytical procedure for its identification based on solid-phase microextraction.

The traceability of Asiago mountain cheese was established by analyzing samples of herbaceous species, milk, and cheese of mountain origin using the head-space solid-phase microextraction sampling procedure coupled with gas chromatography-mass spectrometry. As preliminary work had highlighted the characteristic presence of sesquiterpenes in Asiago mountain cheese, these species were considered effective markers of mountain origin. Systematic qualitative analysis, carried out using a carboxen/polydimethylsiloxane fiber, revealed several sesquiterpenes in mountain herbage and milk, in particular beta-caryophyllene and alpha-humulene, in Asiago mountain cheese, confirming sesquiterpenes as markers of cheese produced from animals grazing on mountain pastures. Analysis was performed on 19 samples of herbage, 8 of milk, and 8 of cheese, collected in summer from 4 mountain farms on the Asiago plateau. For quantitative analysis of caryophyllene in cheese, polydimethylsiloxane fiber sampling, coupled with the standard addition method to eliminate matrix effect, was preferred. The amount of beta-caryophyllene found ranged from 21 to 65 microg/kg.

Altitude↗
PubMed1984

Cyclization of farnesyl pyrophosphate to the sesquiterpene olefins humulene and caryophyllene by an enzyme system from sage (Salvia officinalis).

A soluble enzyme preparation obtained from sage (Salvia officinalis) leaves was shown to catalyze the divalent metal-ion dependent cyclization of trans, trans-farnesyl pyrophosphate to the macrocyclic sesquiterpene olefins humulene and caryophyllene. The identities of the biosynthetic products were confirmed by radiochromatographic analysis and by preparation of crystalline derivatives, and the specificity of labeling in the cyclization reaction was established by chemical degradation of the olefins derived enzymatically from [1-3H2]farnesyl pyrophosphate. These results constitute the first report on the cyclization of farnesyl pyrophosphate to humulene and caryophyllene, two of the most common sesquiterpenes in nature, and the first description of a soluble sesquiterpene cyclase to be isolated from leaves of a higher plant.

Chemical Phenomena↗
PubMed1988

Partial purification and characterization of two sesquiterpene cyclases from sage (Salvia officinalis) which catalyze the respective conversion of farnesyl pyrophosphate to humulene and caryophyllene.

Humulene cyclase and caryophyllene cyclase, two enzymes which catalyze the cyclization of farnesyl pyrophosphate to the respective sesquiterpene olefins, have been partially purified from the supernatant fraction of a sage (Salvia officinalis) leaf epidermis extract and separated from each other by a combination of hydrophobic interaction, gel filtration, and ion-exchange chromatography. The molecular weight of both cyclases was estimated by gel filtration to be 57,000 and both cyclases exhibited a pH optimum of 6.5 and preferred Mg2+ (Km approximately 1.5 mM) as the required divalent metal cation. Both enzymes possessed a Km of about 1.7 microM for farnesyl pyrophosphate, were strongly inhibited by p-hydroxymercuribenzoate, and exhibited comparable sensitivities to a variety of other potential inhibitors. The properties of the two sesquiterpene olefin cyclases, which are the first from a higher plant source to be examined in detail, were very similar to each other and to other monoterpene, sesquiterpene, and diterpene cyclases previously described.

Chromatography, Gel↗
PubMed1962

Microbiological transformations of terpenes. III. Transformations of some mono- and sesqui-terpenes.

The action of Aspergillus niger on mono- and sesqui-terpenic hydrocarbons, such as carane, 3-carene, alpha-santalene, and humulene was studied in shake cultures. Carane, Delta3-carene, and humulene proved to be rather resistant to oxygenation by the experimental strain of A. niger. Carene yielded a hydroxyketone, C(10)H(14)O(2), in poor yields after prolonged fermentation. The sesqui-terpene hydrocarbon, alpha-santalene, was degraded mainly to an acid, tere-santalic acid. Two hydroxylated products were also obtained from alpha-santalene, viz., tere-santalol and an alcohol, C(15)H(24)O.

Alcohols↗
PubMed2006

Quantitative determination of eight components in rhizome (Jianghuang) and tuberous root (Yujin) of Curcuma longa using pressurized liquid extraction and gas chromatography-mass spectrometry.

Curcuma longa (Zingiberaceae) is a native plant of southern Asia and is cultivated extensively throughout the warmer parts of the world. Jianghuang and Yujin are rhizome and tuberous root of C. longa, respectively, which were traditionally used as two Chinese medicines. In this paper, pressurized liquid extraction (PLE) and gas chromatography-mass spectrometry (GC-MS) were developed for quantitative determination/estimation of eight characteristic compounds including beta-caryophyllene, ar-curcumene, zingiberene, beta-bisabolene, beta-sesquiphellandrenendrene, ar-turmerone, alpha-turmerone and beta-turmerone in Jianghuang and Yujin. A HP-5MS capillary column (30 m x 0.25 mm i.d.) coated with 0.25 microm film 5% phenyl methyl siloxane was used for separation and selected ion monitoring (SIM) method was used for quantitation. Hierarchical cluster analysis based on characteristics of eight identified peaks in GC-MS profiles showed that 10 samples were divided into two main clusters, Jianghuang and Yujin, respectively. Four components such as ar-curcumene, ar-turmerone, alpha-turmerone and beta-turmerone were optimized as markers for quality control of rhizome (Jianghuang) and tuberous root (Yujin), which are two traditional Chinese medicines, from Curcuma longa.

Chromatography, High Pressure Liquid↗
PubMed2026

Cytochrome P450- and Dehydrogenase-Mediated Regiospecific and Stereoselective Formation of β- and γ-Lactones in Drimane-Type Sesquiterpenoid Biosynthesis.

Lactone-containing natural products are important candidates for drug discovery. Drimane-type sesquiterpenes (DTSs), characterized by a bicyclic trans-decalin scaffold, can bear both β- and γ-lactone moieties. While γ-lactone-containing DTSs have frequently been reported, β-lactone-containing derivatives are rare, and their biosynthesis remains unexplored. Here, we identified a biosynthetic gene cluster (dri) in Aspergillus ustus and confirmed ustidrimane A (1), a β- and γ-lactone-containing DTS, as its product. Heterologous gene expression, precursor feeding, and enzymatic investigation provided evidence for the formation of both lactone rings. In both cases, the reaction cascade is initiated by regiospecific (and stereoselective) methyl hydroxylation, followed by regiospecific and stereoselective oxidation of one hydroxymethyl group to an aldehyde. The resulting hemiacetal was proven to be subsequently oxidized to a lactone. The β-lactone formation is catalyzed by two cytochrome P450 enzymes (DriE and DriF), followed by two oxidation steps catalyzed by two dehydrogenases (DriG and DriH). These findings differ entirely from the known β-lactone formation in fatty acid-, PKS-, and NRPS-derived metabolites. The subsequent γ-lactone formation is catalyzed by a P450 (DriJ) and a dehydrogenase (DriD). DriJ has been shown to be involved in both methyl hydroxylation and hemiacetal formation, while DriD is responsible for the hemiacetal oxidation and also contributes moderately to its formation. Collectively, these findings establish a sequential P450/dehydrogenase-mediated oxidative cascade for the construction of two distinct lactone motifs within a single DTS scaffold. Moreover, they provide the first insight into the β-lactone formation in terpenes, thus unveiling a new strategy for the construction of this structural motif.

Lactones↗
PubMed2004

[The crop-producing power and chemical composition of the essential oil of the cones of hop cultivars].

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.

Chromatography, Gas↗
PubMed2006

Simultaneous determination of aromatic and terpenic constituents of cloves by means of HPLC with diode array detection.

An HPLC method has been developed for the simultaneous determination of aromatic and terpenic constituents of cloves on a C8 RP column, with the mobile phase consisting of a pH 3.5 phosphate buffer-triethylamine (30%) and acetonitrile (70%); a flow rate of 1.2 mL/min and a diode-array detector were used. Complete separation of all analytes (eugenol (EUG), eugenol acetate (AEUG), beta-caryophyllene, a-humulene and caryophyllene oxide) was achieved within 7 min. Good linearity was found in the range 0.125-40.0 microg/mL for EUG and AEUG and in the range 0.250-20.0 microg/mL for the terpenic compounds. After validation, the method was successfully applied to the analysis of clove oil and clove extract samples. The results obtained indicate good accuracy (recovery percentage mean value corresponding to 99.9%) and satisfactory precision.

Calibration↗
PubMed2004

Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138.

Atherosclerosis is a vascular disorder involving inflammation, a narrowed vascular lumen in the entire tunica intima, and reduced elasticity of the arterial wall. It has been found that Hsp60 from Chlamydia pneumoniae, an obligate bacterial pathogen associated with atheroma lesions, mimics human Hsp60, thereby causing attacks by immune cells on stressed endothelial cells expressing endogenous Hsp60 on their surface. Furthermore, Hsp60 from C. pneumoniae has been shown to promote the growth of vascular smooth muscle cells (VSMCs). To explore probes that can be used for studying signal transduction elicited by the chlamydial Hsp60, we have tested several natural products for their inhibitory actions on the Hsp60-induced proliferation of rat arterial smooth muscle cells. Sesamol, vanillyl alcohol, and trans-ferulic acid exhibited moderate inhibitory actions on the Hsp60-induced cell proliferation; zerumbone, humulene, and caryophylene effectively inhibited it at low concentrations with IC(50) values of 529, 122, and 110 nM, respectively. The results indicated that the 11-membered alicyclic ring is favorable for interactions with receptors involved in the Hsp60-induced VSMC proliferation.

Animals↗
PubMed1990

[Miscellaneous contributions to the essential oils of plants from various territories. LI. On the components of essential oils of Torilis japonica (Houtt.) DC].

The essential oils of Torilis japonica (Houtt.) DC. (Japanese name, Yabujirami) of the family Umbelliferae were prepared from fresh whole herbs and fruits, and investigated by using gas chromatographic and mass spectrometric analyses. The fruits of this plant had been used as a substitute in Japan for a Chinese crude drug Zya-syo-si: Cnidii Monnieri Fructus. Fifty three components were positively identified in the essential oils. The main components of the essential oil were germacrene-D (57.9-71.8% in the oil), alpha-humulene (2.4-13.2%), bicyclogermacrene (1.9-5.4%), beta-caryophyllene (1.5-4.6%), and delta-cadinene (1.0-1.9%).

Monocyclic Sesquiterpenes↗
PubMed2006

Chemical composition and antioxidant properties of clove leaf essential oil.

The antioxidant activity of a commercial rectified clove leaf essential oil (Eugenia caryophyllus) and its main constituent eugenol was tested. This essential oil comprises in total 23 identified constituents, among them eugenol (76.8%), followed by beta-caryophyllene (17.4%), alpha-humulene (2.1%), and eugenyl acetate (1.2%) as the main components. The essential oil from clove demonstrated scavenging activity against the 2,2-diphenyl-1-picryl hydracyl (DPPH) radical at concentrations lower than the concentrations of eugenol, butylated hydroxytoluene (BHT), and butylated hydroxyanisole (BHA). This essential oil also showed a significant inhibitory effect against hydroxyl radicals and acted as an iron chelator. With respect to the lipid peroxidation, the inhibitory activity of clove oil determined using a linoleic acid emulsion system indicated a higher antioxidant activity than the standard BHT.

Antioxidants↗
PubMed1999

[Studies on the chemical constituents of essential oil from roots and rhizomes of Patrinia rupestris].

OBJECTIVE: To study the chemical constituents of the essential oil from the roots and rhizomes of Patrinia rupestris. METHOD: The essential oil was extracted by steam distillation. The components were separated and identified by gas chromatography mass spectrometry and elucidated on the standard mass spectral data. Gas chromatography showed their percentages by area normalization method. RESULTS: Seventeen constituents were identified which make up 74.57% of the oil. CONCLUSION: Transcaryophyllene (38.41%) was the main constituent, and other constituents include alpha-gurjunene, caryophyllene oxide, humulene, 9,12-octadecadienoic acid, etc.

Gas Chromatography-Mass Spectrometry↗
PubMed2006

Anti-inflammatory and anti-allergic properties of the essential oil and active compounds from Cordia verbenacea.

The anti-inflammatory and anti-allergic effects of the essential oil of Cordia verbenacea (Boraginaceae) and some of its active compounds were evaluated. Systemic treatment with the essential oil of Cordia verbenacea (300-600mg/kg, p.o.) reduced carrageenan-induced rat paw oedema, myeloperoxidase activity and the mouse oedema elicited by carrageenan, bradykinin, substance P, histamine and platelet-activating factor. It also prevented carrageenan-evoked exudation and the neutrophil influx to the rat pleura and the neutrophil migration into carrageenan-stimulated mouse air pouches. Moreover, Cordia verbenacea oil inhibited the oedema caused by Apis mellifera venom or ovalbumin in sensitized rats and ovalbumin-evoked allergic pleurisy. The essential oil significantly decreased TNFalpha, without affecting IL-1beta production, in carrageenan-injected rat paws. Neither the PGE(2) formation after intrapleural injection of carrageenan nor the COX-1 or COX-2 activities in vitro were affected by the essential oil. Of high interest, the paw edema induced by carrageenan in mice was markedly inhibited by both sesquiterpenic compounds obtained from the essential oil: alpha-humulene and trans-caryophyllene (50mg/kg, p.o.). Collectively, the present results showed marked anti-inflammatory effects for the essential oil of Cordia verbenacea and some active compounds, probably by interfering with TNFalpha production. Cordia verbenacea essential oil or its constituents might represent new therapeutic options for the treatment of inflammatory diseases.

Animals↗
PubMed2003

Synthesis of a highly hindered hydrindanone via alpha-carbonyl radical cyclization: enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene.

An enantiospecific synthesis of Schinzer's ketone 3 from (R)-(+)-pulegone via alpha-carbonyl radical cyclization was accomplished. This work also constitutes an enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene. The intermediate ketone 4 would be useful for the synthesis of other pinguisane-type sesquiterpenes.

Bridged Bicyclo Compounds↗
PubMed2006

Composition of the essential oil of Helichrysum chasmolycicum growing wild in Turkey.

The chemical compositions of the essential oil obtained from the aerial parts of Helichrysum chasmolycicum were analyzed by gas chromatography and gas chromatography-mass spectrometry. From the 57 identified constituents, representing 66.55% of the oil, the main constituents of the oil were beta-caryophyllene (27.6%), beta-selinene (8.9%), alpha-selinene (8.4%), caryophyllene oxide (7.3%), and carvacrol (2.4%). The essential oil was almost totally characterized by sesquiterpene hydrocarbons such as beta-caryophyllene and alpha- and beta-selinene.

Chromatography, Gas↗
PubMed1994

Sesquiterpenoid unsaturated dialdehydes increase the concentration of intracellular free Ca2+ in human neuroblastoma SH-SY5Y cells.

The effect of the three sesquiterpenoid unsaturated dialdehydes--polygodial, isovelleral, and epipolygodial--on intracellular free Ca2+ concentration, [Ca2+]i, was investigated in the human neuroblastoma cell line SH-SY5Y. [Ca2+]i was measured by the Fura-2 spectrophotofluorometric technique in multi-cell and single-cell experiments. Polygodial and isovelleral induced an increase in [Ca2+]i at low concentrations (0.1 and 0.5 micrograms/ml, respectively) but epipolygodial affected [Ca2+]i only at a high concentration (10 micrograms/ml). The results indicated that there was a relationship between the effect on [Ca2+]i and the pungency of the sesquiterpenes tested. Experiments in a Ca(2+)-free extracellular solution showed that Ca2+ was also released from intracellular calcium stores. Images from single-cell experiments indicated that polygodial induced fluctuations in the [Ca2+]i in some cells. The mechanism behind the sesquiterpene induced increase of the [Ca2+]i was not identified but a possible mobilization of inositol phosphates is considered.

Aldehydes↗
PubMed1994

Khusimol, a non-peptide ligand for vasopressin V1a receptors.

In the course of a random screen of various plant extracts, khusimol [1], a non-peptide molecule isolated from the root of Vetiveria zizanioides, was found to competitively inhibit the binding of vasopressin to rat liver V1a receptors (Ki = 50 microM). The 1H- and 13C-nmr spectra of this sesquiterpene alcohol were assigned unambiguously.

Animals↗
PubMed2004

Unusual sesquiterpene lactones from Ligularia virgaurea spp. oligocephala.

[structure: see text] [structure: see text] Sesquiterpene lactones, ligulolide A (1) and 6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide (2), were isolated from Ligularia virgaurea spp. oligocephala. Their structures were established by analysis of one- and two-dimensional NMR data. The relative stereostructures were determined on the basis of NOESY and single-crystal X-ray experiments. 1 represents a novel sesquiterpene carbon framework, and a possible biosynthetic process is proposed. 2 is a novel eremophilane-type sesquiterpene.

Antineoplastic Agents↗