Secondary metabolites, structure diagram: Trivial name - sterigmatocystin

Date: 26 November 2013

Secondary metabolites, structure diagram: Trivial name – sterigmatocystin

Notes:

Species: A. discophorus, A. flavus, A. multicolor, A. nidulans, A. olivicola, A. parasiticus, A. rambellii, A. ustus, A. versicolor, Emericella nidulans, Emericella venezuelensisSystematic name 7H-Furo[3′,2′:4,5]furo[2,3-c]xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR,12cS)-Molecular formulae: C18H12O6Molecular weight: 324.284Chemical abstracts number: 10048-13-2Selected references: Steyn M; Rabie C J Production of sterigmatocystin. Journal – Association of Official Analytical Chemists (1975), 58(3), 622-3. Tag, Andrew; Hicks, Julie; Garifullina, Gulnara; Ake, Charles, Jr; Phillips, T. D.; Beremand, Marian; Keller, Nancy (CORPORATE SOURCE Departments of Plant Pathology and Microbiology, Texas A and M University, College Station, TX 77843-2132, USA).Hamasaki, Takashi; Nakagomi, Takeo; Hatsuda, Yuichi; Fukuyama, Keiichi; Katsube, Yukiteru (Fac. Agric., Tottori Univ., Tottori 680, Japan). Agric. Biol. Chem., 44(5), 1149-55 (English) 1980.Frisvad JC, Skouboe P, Samson RA. Taxonomic comparison of three different groups of aflatoxin producers and a new efficient producer of aflatoxin B1, sterigmatocystin and 3-O-methylsterigmatocystin, Aspergillus rambellii sp. nov. Syst Appl Microbiol. 2005 Jul;28(5):442-53. Frisvad JC, Samson RA. Emericella venezuelensis, a new species with stellate ascospores producing sterigmatocystin and aflatoxin B1. Syst Appl Microbiol. 2004 Nov;27(6):672-80.Toxicity: Oral LD50 in albino male rat 166 mg/kg body-weight, intraperitoneal LD50 in male monkeys 32 mg/kg body-weight. It has been shown to cause liver and kidney damage including cirrhosis of the liver in primates. Hsieh DP, Atkinson DN. Bisfuranoid mycotoxins: their genotoxicity and carcinogenicity. Adv Exp Med Biol. 1991;283:525-32. Review. Produced by several Aspergillus spp, including Aspergillus nidulans, Aspergillus flavus, Aspergillus ustus and Aspergillus versicolor, the last of which is associated with the production of sterigmatocystin in cheeses stored at low temperatures for extended periods of time. It is also produced by Bipolaris sorokiniana, Monocillium nordinii, Chaetomium thielarioideum and Chaetomium udagawae.