Biotransformation of (-)-(R)-α-phellandrene: antimicrobial activity of its major metabolite.
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.
Department of Pharmacognosy, Anadolu University, Faculty of Pharmacy, TR-26470, Eskişehir, Turkey. giscan@anadolu.edu.tr
Gökalp
G
İşcan
Neşe
N
Kirimer
Fatih
F
Demirci
Betül
B
Demirci
Yoshiaki
Y
Noma
K Hüsnü Can
KH
Başer
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects / Q000378:metabolism; D001424:Bacterial Infections / Q000188:drug therapy; D001711:Biotransformation; D002175:Candida / Q000187:drug effects; D002177:Candidiasis / Q000188:drug therapy; D000081005:Cyclohexane Monoterpenes; D005658:Fungi / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D009181:Mycoses / Q000188:drug therapy
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; C516209:p-menth-2-en-1-ol; C005403:alpha phellandrene