Microbial transformation of (-)-guaiol and antibacterial activity of its transformed products.
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.
Choudhary
Muhammad Iqbal
MI
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. hej@cyber.net.pk
Batool
Iffat
I
Atif
Muhammad
M
Hussain
Samreen
S
Atta-Ur-Rahman
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
D000900:Anti-Bacterial Agents; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C469146:guaiol