Biotransformation of vulgarin

K Orabi; F El-Feraly; W Al-Sulmy; M Al-Yahya

doi:10.1055/s-0032-1320660

Planta Medica, Table of Contents

Biotransformation of vulgarin

K Orabi ¹, F El-Feraly ², W Al-Sulmy ², M Al-Yahya ²

¹Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Health Sciences Center, Kuwait University, Safat 13110, Kuwait
²Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

Abstract

Microbial transformation studies of the eudesmanolide vulgarin (1) have revealed that it was metabolized by a number of microorganisms. Using a standard two-stage fermentation technique, Beauvaria bassiana (ATCC 7159) produced one more polar metabolite 2. Moreover, Hansenula anomala (ATCC 20170) partially converted vulgarin into another less polar metabolite 3 and a more polar one 4. These metabolites were characterized on the basis of their spectral data as 1-epi-tetrahydrovulgarin (1α,4α-dihydroxy-5αH,6,11βH-eudesman-6,12-olide, 2), dihydrovulgarin (4α-hydroxy-1-oxo-5αH,6,11βH-eudesman-6,12-olide, 3), and 3α-hydroxydihydrovulgarin (3α,4α-dihydroxy-1-oxo-5αH,6,11βH-eudesman-6,12-olide, 4). Metabolite 4 identity was further confirmed through chemical synthesis.