Abstract
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.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Betts R. E., Walters D. E., Rosazza J. P. Microbial transformations of antitumor compounds. 1. Conversion of acronycine to 9-hydroxyacronycine by Cunninghamella echinulata. J Med Chem. 1974 Jun;17(6):599–602. doi: 10.1021/jm00252a006. [DOI] [PubMed] [Google Scholar]
- Driscoll J. S., Hazard G. F., Jr, Wood H. B., Jr, Goldin A. Structure-antitumor activity relationships among quinone derivatives. Cancer Chemother Rep 2. 1974 Apr;4(2):1–362. [PubMed] [Google Scholar]
- Otten S., Rosazza J. P. Microbial transformations of natural antitumor agents: oxidation of lapachol by Penicillium notatum. Appl Environ Microbiol. 1978 Mar;35(3):554–557. doi: 10.1128/aem.35.3.554-557.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Smith R. V., Rosazza J. P. Microbial models of mammalian metabolism. J Pharm Sci. 1975 Nov;64(11):1737–1759. doi: 10.1002/jps.2600641104. [DOI] [PubMed] [Google Scholar]
- da Consolaço M., Linardi F., de Oliveira M. M., Sampaio M. R. A lapachol derivative active against mouse lymphocytic leukemia P-388. J Med Chem. 1975 Nov;18(11):1159–1161. doi: 10.1021/jm00245a027. [DOI] [PubMed] [Google Scholar]
- de Lime O. G., Coêlho J. S., d' Albuquerque I. L., de Mello J. F., Martins D. G., Lacerda A. L., de Moraes e Souza M. A. Substâncias antimicrobianas de plantas superiores. XXXV. Atividade antimicrobiana e antitumoral de lawsona (2-hidroxi-1,4-naphthoquinone) em comparaço com o lapachol (2-hidroxi-3-(-3-metil-2-butenil)-1,4-naphthoquinone. Rev Inst Antibiot (Recife) 1971 Jun;11(1):21–26. [PubMed] [Google Scholar]