• O-methylsterigmatocystin packaged and labeled in glass vial.

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SKU: M052

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Description

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 is soluble in DMSO and DMF. Moderately soluble in ethanol and methanol.  Practically insoluble in water.

    CAS Number

    17878-69-2

    Molecular Formula

    C19H14O6

    Molecular Weight

    338.3

    Storage Conditions

    -20°C

Applications

    Application

    O-Methylsterigmatocystin can be used to study the aflatoxin biosynthetic pathway.

    Microbiology Applications

    An oxidoreductase gene (ord1) is sufficient to accomplish the last step of the aflatoxin biosynthetic pathway in A. flavux and A. parasiticus. It can convert O-methylsterigmatocystin to aflatoxin B1.(AFB1). 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.

Specifications

    Appearance

    Pale yellow solid

    Source

    Chaetomium

References

    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

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