Microbial Transformation of Isolongifolen‐4‐one
M. Iqbal ChoudharyH.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi‐75270, Pakistan (phone: +92‐21‐9243224, ‐9243211; fax: +92‐21‐9243190‐91)Syed Ghulam MusharrafH.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi‐75270, Pakistan (phone: +92‐21‐9243224, ‐9243211; fax: +92‐21‐9243190‐91)Mahmud Tareq Hassan KhanH.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi‐75270, Pakistan (phone: +92‐21‐9243224, ‐9243211; fax: +92‐21‐9243190‐91)Doaa AbdelrahmanDepartment of Chemistry, University of Calgary, Calgary, Alberta, Canada T2N 1N4M. ParvezDepartment of Chemistry, University of Calgary, Calgary, Alberta, Canada T2N 1N4Farzana ShaheenH.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi‐75270, Pakistan (phone: +92‐21‐9243224, ‐9243211; fax: +92‐21‐9243190‐91)Atta‐ur RahmanH.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi‐75270, Pakistan (phone: +92‐21‐9243224, ‐9243211; fax: +92‐21‐9243190‐91)
2003en
ABI
Abstract
Abstract The microbial transformation of (+)‐isolongifolen‐4‐one ( 4 ) by a number of fungi by means of a standard two‐stage fermentation technique afforded (7 R )‐12‐hydroxyisolongifolen‐4‐one ( 5 ), (7 S )‐13‐hydroxyisolongifolen‐4‐one ( 6 ), (11 R )‐11‐hydroxyisolongifolen‐4‐one ( 7 ), (10 R )‐10‐hydroxyisolongifolen‐4‐one ( 8 ), and (9 R )‐9‐hydroxyisolongifolen‐4‐one ( 9 ) ( Scheme ). All five metabolites were found to be new, and metabolites 6 and 9 showed potent tyrosinase inhibitory activity ( Table 1 ). The metabolites and their derivatives were characterized on the basis of spectroscopic and single‐crystal X‐ray‐diffraction techniques.
Identifiers
Citations and references
Cited by 20 references