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.

Preparation of Phosphatidylated Terpenes via Phospholipase D-Mediated Transphosphatidylation

Abstract: Terpenes such as geraniol, geranylgeraniol, farnesol, and phytol are known as functional compounds which exhibit anticancer effects and activate nuclear receptors. For the application of functional terpenes in various fields, including the cosmetic and food industries, we attempted to synthesize phosphatidylated terpenes (terpene-PLs) by using phospholipase D (PLD). Transphosphatidylation of phosphatidylcholine with terpenes was carried out using PLD in a biphasic system containing ethyl acetate/water or in an aqueous system without organic solvent. The yield of terpene-PL increased with the reaction time and the amount of PLD in both the biphasic and aqueous systems. Further, the yield of terpene-PL in the aqueous system was higher than that in the biphasic system. In addition, among four PLDs from Streptomyces sp., Streptomyces chromofuscus, cabbage, and peanut, only the PLD from Streptomyces sp. could synthesize terpene-PL. The reaction yield, based on substrate phospholipid, of phosphatidylgeraniol reached 90 mol% under the following optimal reaction conditions: 50 μmol soyPC; 2,000 μmol geraniol; 1.6 U PLD; 0.8 ml of 0.2 M sodium acetate buffer (pH 5.6); temperature, 37 °C ; and reaction time, 24 h. The reaction yields of phosphatidylfarnesol, phosphatidylgeranylgeraniol, and phosphatidylphytol were 73, 54, and 17 mol%, respectively.

Origin and early evolution of the plant terpene synthase family

Abstract: Significance Land plants produce numerous terpenoids that regulate development and mediate environmental interactions. Thus, how typical plant terpene synthase (TPS) genes originated and evolved to create terpenoid diversity is of fundamental interest. By investigating TPSs from the genomes and transcriptomes of diverse taxa of green plants, it was demonstrated here that the ancestral TPS gene originated in land plants after divergence from green algae and encoded a bifunctional ent-kaurene synthase for phytohormone biosynthesis. This ancestral TPS then underwent gene duplication at least twice early in land plant evolution, leading to three ancient TPS lineages reflecting sub-functionalization of class I and II activities for phytohormone biosynthesis and neo-functionalization from primary to secondary metabolism, followed in each case by dynamic functional divergence.

Photochemical hydroperoxidation of terpenes I. Synthesis and characterization of α-pinene, β-pinene and limonene hydroperoxides

Abstract: The photohydroperoxidation of the stereoisomers of three terpenes ((+) and (−) α-pinene, (+) and (−) β-pinene and (+) and (−) limonene) has been performed by using photocatalysts, such as zinc oxide, or sensitizers, such as anthracene or rose Bengal, supported on cross-linked polystyrene. Hydroperoxides accumulated alone in the first stages of sensitized oxidation but were always associated with alcoholic and carbonyl products in the case of ZnO. Secondary products obtained for longer exposure times in sensitized oxidations were identified by gas chromatography/mass spectrometry and mechanisms for their formation, deriving from the photolysis of parent hydroperoxides, were suggested.

Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum.

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.