Microbial transformations of natural antitumor agents: conversion of lapachol to dehydro-alpha-lapachone by Curvularia lunata.
Microbial transformation of lapachol, a naturally occurring naphthoquinone, was carried out by Curvularia lunata (NRRL 2178). The fungus brings about oxidative cyclization of the substrate to dehydro-alpha-lapachone, which was isolated and characterized by nuclear magnetic resonance and mass spectral analyses; its structure was verified by chemical synthesis. The metabolite is a naturally occurring chromene possessing antibacterial and antitumor activities.
D000972:Antineoplastic Agents, Phytogenic / Q000378:metabolism*; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D003904:Mitosporic Fungi / Q000378:metabolism*; D009285:Naphthoquinones / Q000378:metabolism*
D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones; C008252:lapachol