Biotransformation of (1S)-2-Carene and (1S)-3-Carene by Picea abies Suspension Culture

Abstract

Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture led to the formation of oxygenated products. (1S)-2-Carene was transformed slowly and the final product was identified as (1S)-2-caren-4-one. On the other hand, the transformation of (1S)-3-carene was rapid and finally led to the formation of (1S)-3-caren-5-one and (1S)-2-caren-4-one as equally abundant major products. The time-course of the reaction indicates that some products abundant at the beginning of the reaction (e.g. (1S,3S,4R)-3,4-epoxycarane and (1R)-p-mentha-1(7),2-dien-8-ol) were consumed by a subsequent transformations. Thus, a precise selection of the biotransformation time may be used for a production of specific compounds.

Comparison of different extraction methods of Brazilian “pacová” (Renealmia petasites Gagnep.) oilseeds for the determination of lipid and terpene composition, antioxidant capacity, and inhibitory effect on neurodegenerative enzymes

“…Their findings suggested that the oil has a potential cytotoxic activity against DLA cells, where 50 μg of extract/mL was able to inhibit 89% of the cells. The biotransformation of the monoterpenes 2-carene and 3-carene originates oxygenated terpenes that find application in antifungal and antibacterial mechanisms, playing an essential role in plant defense ( Dvorakova, Valterova, Saman, & Vanek, 2011 ). In fact, oxygenated mono- and sesquiterpenes were found to be the main constituents in different species of Zingiberaceae family ( Mesomo et al, 2013 ).…”

Development of Mechanism-Based Structural Alerts for Respiratory Sensitization Hazard Identification

“…However, for these two chemicals an alternative mechanism involving the formation of a hydroperoxide cannot be ruled out (mechanism not shown). These oxidation reactions producing epoxides (or hydroperoxides) have been previously shown to occur in a variety of oxygenated systems. − It is therefore likely that such species will be readily produced in the lung. 1,2-Benzisothiazolin-3-one, 3-amino-5-mercapto-1,2,4-triazole, captafol, and penicillamine all contain sulfur atoms that can undergo covalent binding via disulfide exchange (Figure ).…”

Assessment of metabolome diversity in black and white pepper in response to autoclaving using MS- and NMR-based metabolomics and in relation to its remote and direct antimicrobial effects against food-borne pathogens

“…a-Phellandrene-8-ol (peak 28) constituted the major alcohol in autoclaved white pepper to originate from the thermal isomerization and oxidation of isoterpenoline, 39 enriched in raw white pepper. a-Phellandrene-8ol also known as p-mentha-1(7),2-dien-8-ol is an oxygenated monoterpene with potential antimicrobial effect 40 previously reported in pepper essential oil. 4 Likewise, linalool (peak 23) and 3-hexenol (peak 1) were detected at trace levels in black pepper and slightly increase upon autoclaving to reach 1.5 and 1.6%, respectively.…”