Microbial transformations of natural antitumor agents. 7. 14-alpha-Hydroxylation of withaferin-A by Cunninghamella elegans (NRRL 1393).
Microbial transformation experiments were conducted with the steroidlactone, withaferin-A (1a). Cunninghamella elegans (NRRL 1393) converts withaferin-A into two major metabolites, one of which has been indentified as 14alpha-hydroxywithaferin-A (1b). The metabolite is obtained in 37% yield, and its structure was determined on the basis of pmr and mass spectral evidence. The metabolite has the same level of antitumor activity as withaferin-A against the Sarcoma-180 tumor test system in mice.
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000378:metabolism* / Q000627:therapeutic use; D001711:Biotransformation; D002782:Cholestenes / Q000378:metabolism*; D002783:Cholestenones / Q000378:metabolism* / Q000627:therapeutic use; D005658:Fungi / Q000378:metabolism*; D006900:Hydroxylation; D007783:Lactones / Q000378:metabolism / Q000627:therapeutic use; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D009090:Mucorales / Q000378:metabolism*; D012510:Sarcoma 180 / Q000188:drug therapy
D000972:Antineoplastic Agents, Phytogenic; D002782:Cholestenes; D002783:Cholestenones; D007783:Lactones