Bioconversion of (+)- and (-)-alpha-pinene to (+)- and (-)-verbenone by plant cell cultures of Psychotria brachyceras and Rauvolfia sellowii

Abstract

Financial support: CNPq, CAPES and FAPERGS.Keywords: alpha-pinene, biotransformation, verbenol, verbenone. This work describes the bioconversion of (-)-and (+)-alpha-pinene (2,6,6-trimethyl-bicyclo[3.1.1]hept-2-ene), targeted at the production of (-)-and (+)-verbenone (4,6,6-trimethyl-bicyclo (3.1.1) hept-3-en-2-one), respectively, using Psychotria brachyceras and Rauvolfia sellowii cell suspension cultures. P. brachyceras showed selectivity to (-)-alpha-pinene with 80.9% conversion (relative integrated area gas chromatography -mass *Corresponding author spectrometry (GC -MS)) of (-)-verbenone in 10-dayincubation, whereas R. sellowii was able to convert both pinene enantiomers (37.6% conversion of (-)-verbenone in 7-day-incubation and 32.2% conversion of (+)-verbenone in 10-day-incubation). In both systems transverbenol was formed as main product and then slowly biocatalyzed to verbenone. Verbenone were also present among the autoxidation products during control Abbreviations

Natural Carbon Isotope Composition Distinguishes Compound Groups of Biogenic Volatile Organic Compounds (BVOC) in Two Mediterranean Woody Species

“…Compared to all other monoterpenoids, verbenone and bornyl acetate were strongly depleted in 13 C. Verbenone is a monoterpene ketone enzymatically derived from α-pinene (Vanek et al, 2005;Pereira Limberger et al, 2007). In this context, isotope fractionation is surprising, as no carbon bondage or breakage is involved in the formation of verbenone (Figure 5).…”

“…In this context, isotope fractionation is surprising, as no carbon bondage or breakage is involved in the formation of verbenone (Figure 5). α-pinene is simply transformed by autoxidation at the allylic position to trans-verbenol, which slowly transforms to verbenone by oxidation (Lindmark-Henriksson et al, 2003;Pereira Limberger et al, 2007). As verbenone was mostly detected in C. ladanifer, the possibility of storage emissions cannot be fully excluded.…”

Effect of Extraction Technique on Composition of Volatile Constituents of Oleoresin from Pinus Brutia Ten.

“…α-pinene and β-pinene are the major constituents of turpentine. Pinenes are mostly used as starting materials to produce more valuable components (Jantam and Ahmad, 1999;McMorn et al, 2000;Rezzi et al, 2005;Wang et al, 2006;Limberger et al, 2007;Mercier et al, 2009). Besides pinenes, turpentine contains other terpenes such as camphene, Δ 3 -carene, tricyclene, myrcene, pcymene, limonene, β-caryophyllene and aromadendrene.…”

Alpha-pinene and dizocilpine (MK-801) attenuate kindling development and astrocytosis in an experimental mouse model of epilepsy

“…Essential oils, including α-pinene, have been used to treat various diseases ( Mercier et al, 2009 ). α-pinene is widely used as a food flavoring ingredient ( Pereira Limberger et al, 2007 ; Ana Cristina da Silva Rivas et al, 2012 ) and has been approved as a safe food additive by the U.S. Food and Drug Administration (FDA 2015). α-pinene has anti-inflammatory ( Martin et al, 1993 ; Zhou et al, 2004 ), anti-depressive ( Ahmad et al, 2013 ), anti-oxidative ( Singh et al, 2006 ), anti-tumor ( Eftekhar et al, 2004 ), and anti-nociceptive effects ( Him et al, 2008 ).…”