O-Methylsterigmatocystin is a natural product formed via methylation of sterigmatocystin. O-Methylsterigmatocystin is a xanthone metabolite isolated from several species of Aspergillus and Chaetomium. It is a precursor to aflatoxin G1 and B1 and, while it is considered mutagenic, teratogenic and carcinogenic, it is less potent than the aflatoxins. Research on this metabolite has focused on its genetic and phenotypic relationship to aflatoxins. O-Methylsterigmatocystin can be used to study the aflatoxin biosynthetic pathway.
O-Methylsterigmatocystin is soluble in DMSO and DMF, moderately soluble in ethanol and methanol, and practically insoluble in water.
| Microbiology Applications | O-Methylsterigmatocystin is converted to aflatoxin B1(AFB1) via an oxidoreductase gene (ord1) in the last step of the aflatoxin biosynthetic pathway in A. flavux and A. parasiticus. The ord1 gene encodes a cytochrome P-450-type monooxygenase, and the gene has been assigned to a new P-450 gene family named CYP64. Results suggest that this gene is responsible for this complex and crucial step of the pathway that is unique to aflatoxigenic fungal species. |
| References |
Burkhardt HJ and Forgacs J (1968) O-Methylsterigmatocystin, a new metabolite of Aspergillus flavus. Tetrahedron. 242):717-720 Fukuyama K et al (1976) The crystal structures of sterigmatocystin and O-Methylsterigmatocystin, metabolites of the genus Aspergillus. Bull. Chem. Soc. Japan 49(4):1153-1154 Prieto R and Woloshuk CP (1997) ord1, an oxidoreductase gene responsible for conversion of O-Methylsterigmatocystin to aflatoxin in Aspergillus flavus. Appl. Environ. Microbiol. 63(5):1661-1666 Udagawa S et al (1979) The production of chaetoglobosins, sterigmatocystin, O-Methylsterigmatocystin, and chaetocin by Chaetomium spp. and related fungi. Can. J. Microbiol. 25(2):170-177 |
