Terpene

About: Terpene is a research topic. Over the lifetime, 2208 publications have been published within this topic receiving 51480 citations. The topic is also known as: terpenes.

Development of Gas-Chromatographic Method for Simultaneous Determination of Cannabinoids and Terpenes in Hemp

Abstract: An original gas chromatographic method has been developed for simultaneous determination of major terpenes and cannabinoids in plant samples and their extracts. The main issues to be addressed were the large differences in polarity and volatility between both groups of analytes, but also the need for an exhaustive decarboxylation of cannabinoid acidic forms. Sample preparation was minimised, also by avoiding any analyte derivatisation. Acetone was found to be the most appropriate extraction solvent. Successful chromatographic separation was achieved by using a medium polarity column. Limits of detection ranged from 120 to 260 ng/mL for terpenes and from 660 to 860 ng/mL for cannabinoids. Parallel testing proved the results for cannabinoids are comparable to those obtained from established HPLC methods. Despite very large differences in concentrations between both analyte groups, a linear range between 1 and 100 µg/mL for terpenes and between 10 and 1500 µg/mL for cannabinoids was determined.

Structural Requirements for Potent Direct Inhibition of Human Cytochrome P450 1A1 by Cannabidiol: Role of Pentylresorcinol Moiety

Abstract: Our recent work has shown that cannabidiol (CBD) exhibits the most potent direct inhibition of human cytochrome P450 1A1 (CYP1A1) among the CYP enzymes examined. However, the mechanism underlying this CBD inhibition remains to be clarified. Thus, to elucidate the structural requirements for the potent inhibition by CBD, the effects of CBD and its structurally related compounds on CYP1A1 activity were investigated with recombinant human CYP1A1. Olivetol, which corresponds to the pentylresorcinol moiety of CBD, inhibited the 7-ethoxyresorufin O-deethylase activity of CYP1A1; its inhibitory effect (IC50=13.8 µM) was less potent than that of CBD (IC50=0.355 µM). In contrast, d-limonene, which corresponds to the terpene moiety of CBD, only slightly inhibited CYP1A1 activity. CBD-2'-monomethyl ether (CBDM) and CBD-2',6'-dimethyl ether inhibited CYP1A1 activity with IC50 values of 4.07 and 23.0 µM, respectively, indicating that their inhibitory effects attenuated depending on the level of methylation on the free phenolic hydroxyl groups in the pentylresorcinol moiety of CBD. Cannabidivarin inhibited CYP1A1 activity, although its inhibitory potency (IC50=1.85 µM) was lower than that of CBD. The inhibitory effects of Δ(9)-tetrahydrocannabinol and cannabielsoin (IC50s ≈10 µM), which contain a free phenolic hydroxyl group and are structurally constrained, were less potent than that of CBDM, which contains a free phenolic hydroxyl group and is rotatable between pentylresorcinol and terpene moieties. These results suggest that the pentylresorcinol structure in CBD may have structurally important roles in direct CYP1A1 inhibition, although the whole structure of CBD is required for overall inhibition.

Regulation of Terpenoid Biosynthesis in Higher Plants

Abstract: Consider the following general facts in relation to the need for regulation of the pathways for biosynthesis of terpenoid compounds in higher plants. Higher plants produce a wide array of terpenoid compounds including monoterpenes, sesquiterpenes, diterpenes, triterpenes and sterols, tetraterpenoid carotenes and xanthophylls, long-chain polyprenyls, and mixed terpenoids that contain an isoprenoid moiety as an integral part of their structures. A single plant species may produce many terpenoid substances including representatives from most or all of these groups. Some terpenoids, such as sterols, gibberellins, carotenes, and the chlorophyll pigments with their polyprenyl side-chains, presumably are produced in all higher green plants. Other terpenoids are formed much more selectively by a few species. Some terpenoids are produced in large quantities and others only in traces.

Citrus Flavor. Volatile Constituents of the Essential Oil of the Orange (Citrus sinensis)a,b

Abstract: SUMMARY Analysis by gas-liquid chromatography (GLC) of the essential oil from California Valencia oranges revealed over 50 components. A preliminary separation of the intact oil into two major fractions, the terpenes and terpenoids, was made by liquid-solid chromatographic techniques. Examination of the terpene fraction by GLC revealed 15 constituents, of which a number were tentatively identified. The terpenoid fraction contained some 37 constituents, many of which were tentatively identified. These techniques increased resolution and permitted tentative identification of some 14 compounds not hitherto reported in Valencia orange oil. These compounds arc: 3-hepten-l- 01; n-octyl acetate; n-undecanal; hornyl acetate; isopulegol; n-decyl acetate; borneol; citronellol; neral; geranyl acetate; α -pinene; α -phellandrene; γ-terpinene; and p-cymene. The constituents were tentatively identified by calculating relative corrected retention volumes and comparing these with values for known compounds. Two stationary liquid phases used yielded data that lend credence to the tentative assignment of identities of the constituents isolated. In addition, infrared examination of some collected fractions made possible partial identification of the compounds.