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

Abstract

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 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 experiments, but in much lower amounts and accompanied by several by-products, highlighting the usefulness of the biotransformation process.