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Biotransformation of (−)‐( R )‐ α ‐Phellandrene: Antimicrobial Activity of Its Major Metabolite
Author(s) -
İşcan Gökalp,
Kırımer Neşe,
Demirci Fatih,
Demirci Betül,
Noma Yoshiaki,
Başer K. Hüsnü Can
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201100283
Subject(s) - metabolite , biotransformation , chemistry , antimicrobial , terpene , monoterpene , bacteria , microorganism , yeast , minimum inhibitory concentration , stereochemistry , biochemistry , organic chemistry , biology , enzyme , genetics
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 ( MIC s=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.