Zeitschrift für Naturforschung C · 2004 · 20 citations · 0 references
Life SciencesBiochemistryMicrobiologyMetabolismMicrobial MetabolismMycologyFungal MetabolismFungal Secondary MetabolitesMetabolite IdentificationMicrobial BiotransformationMicrobial Natural Product BiosynthesisSecondary Metabolite BiosynthesisBioactive Fungal MetabolitesCarbon-carbon Bond FormationFungal Bioactive CompoundsFungal Metabolite BiosynthesisFungal Terpenoid BiosynthesisMicrobial Mediation Of Chemical TransformationsPlant-associated Fungal MetabolitesStructure Elucidation Of Fungal Metabolites
Fungal biotransformations of alpha-santonin (1) were conducted with Mucor plumbeus (ATCC 4740), Cunninghamella bainieri (ATCC 9244), Cunninghamella echinulata (ATCC 9245), Curvularia lunata (ATCC 12017) and Rhizopus stolonifer (ATCC 10404). Rhizopus stolonifer (ATCC 10404) metabolized compound 1 to afford 3,4-epoxy-alpha-santonin (2) and 4,5-dihydro-alpha-santonin (3) while Cunninghamella bainieri (ATCC 9244), Cunninghamella echinulata (ATCC 9245) and Mucor plumbeus (ATCC 4740) were capable of metabolizing compound 1 to give a reported metabolite, 1,2-dihydro-alpha-santonin (4). The structures of these transformed metabolites were established with the aid of extensive spectroscopic studies. These fungi regiospecifically reduced the carbon-carbon double bond in ring A of alpha-santonin.