Biotransformation of (-)-(R)-α-phellandrene: antimicrobial activity of its major metabolite.

Gökalp İşcan, Neşe Kirimer, Fatih Demirci, Betül Demirci, Yoshiaki Noma, K Hüsnü Can Başer

Index: Chem. Biodivers. 9(8) , 1525-32, (2012)

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Abstract

Terpene derivatives converted by microbial biotransformation constitute an important resource for natural pharmaceutical, fragrance, and aroma substances. In the present study, the monoterpene α-phellandrene was biotransformed by 16 different strains of microorganisms (bacteria, fungi, and yeasts). The transformation metabolites were initially screened by TLC and GC/MS, and then further characterized by NMR spectroscopic techniques. Among the six metabolites characterized, 6-hydroxypiperitone, α-phellandrene epoxide, cis-p-menth-2-en-1-ol, and carvotanacetone, which originated from (-)-(R)-α-phellandrene, are reported for the first time in this study. Additionally, the substrate and the metabolite 5-p-menthene-1,2-diol were subjected to in vitro antibacterial and anticandidal tests. The metabolite showed moderate-to-good inhibitory activities (MICs=0.125 to >4 mg/ml) against various bacteria and especially against Candida species in comparison with its substrate (-)-(R)-α-phellandrene and standard antimicrobial agents.Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich.