Biotransformation of (-)-(R)-a-Phellandrene: Antimicrobial Activity of Its Major Metabolite

İŞCAN G., KIRIMER N., DEMİRCİ F., DEMİRCİ B., Noma Y., BAŞER K. H. C.

CHEMISTRY & BIODIVERSITY, cilt.9, sa.8, ss.1525-1532, 2012 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 9 Sayı: 8
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1002/cbdv.201100283
  • Dergi Adı: CHEMISTRY & BIODIVERSITY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1525-1532
  • Anahtar Kelimeler: Biotransformation, (R)-a-Phellandrene, Menthene-1, 2-diol, Antibacterial activity, MICROBIAL TRANSFORMATIONS, ESSENTIAL OILS, BIOCATALYSIS, MS
  • Anadolu Üniversitesi Adresli: Evet

Özet

Terpene derivatives converted by microbial biotransformation constitute an important resource for natural pharmaceutical, fragrance, and aroma substances. In the present study, the monoterpene a-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, a-phellandrene epoxide, cis-p-menth-2-en-1-ol, and carvotanacetone, which originated from (-)-(R)-a-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)-a-phellandrene and standard antimicrobial agents.