title: Microbial transformation of (-)-guaiol and antibacterial activity of its transformed products.
abstract: Microbial transformation of the sesquiterpene (-)-guaiol (1) [1(5)-guaien-11-ol] was investigated using three fungi, Rhizopus stolonifer, Cunninghamella elegans, and Macrophomina phaseolina. Fungal transformation of 1 with Rhizopus stolonifer yielded a hydroxylated product, 1-guaiene-9 beta,11-diol (2). In turn, Cunninghamella elegans afforded two mono- and dihydroxylated products, 1-guaiene-3beta,11-diol (3) and 1(5)-guaiene-3beta,9 alpha,11-triol (4), while Macrophomina phaseolina produced two additional oxidative products, 1(5)-guaien-11-ol-6-one (5) and 1-guaien-11-ol-3-one (6). All metabolites were found to be new compounds as deduced on the basis of spectroscopic techniques. Compounds 1-6 were evaluated for their activity against several bacterial strains.
authors: H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. hej@cyber.net.pk
authors: Muhammad Iqbal
authors: MI
authors: Choudhary
authors: Iffat
authors: I
authors: Batool
authors: Muhammad
authors: M
authors: Atif
authors: Samreen
authors: S
authors: Hussain
authors: Atta-Ur-Rahman
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D020093:Cunninghamella / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000737:chemistry; D015394:Molecular Structure; D012233:Rhizopus / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D045789:Sesquiterpenes, Guaiane; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C469146:guaiol