Biotransformation of (−)‐(R)‐α‐Phellandrene: Antimicrobial Activity of Its Major Metabolite

G İşcan, N Kırımer, F Demirci, B Demirci… - Chemistry & …, 2012 - Wiley Online Library
Chemistry & Biodiversity, 2012Wiley Online Library
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 …
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.
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