3716 Sterigmatocystin Sterigmatocystin is a mycotoxin of Aspergillus versicolor and Chaetomium species Sterigmatocystin is a poison of the type dermatoxin, from the fungi genus Aspergillus. It appears on crusts of cheese with mold. Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins (compare general fact sheet number 2), and consists of a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor. It has been reported in mouldy grain, green coffee beans and cheese although information on its occurrence in foods is limited. It appears to occur much less frequently than the aflatoxins, although analytical methods for its determination have not been as sensitive until recently, and so it is possible that small concentrations in food commodities may not always have been detected. Although it is a potent liver carcinogen similar to aflatoxin B1, current knowledge suggests that it is nowhere near as widespread in its occurrence. If this is the true situation it would be justified to consider sterigmatocystin as no more than a risk to consumers in special or unusual circumstances. Sterigmatocystin is a number of closely related compounds such o-methyl sterigmatocystin are known and some may also occur naturally. The IARC-classification of sterigmatocystin is group 2B, which means it is possibly carcinogenic to humans. In practice, the risk is quite low however, because this substance only appears on cheese crusts with mold, and because of that the chance of daily exposure is very low. Sterigmatocystin is a molded crust is best not to be consumed in whole, but after removing the crust, the cheese can still be consumed. Sterigmatocystin is a different kind of mold than that which appears on cheese itself, which can simply be removed before further consumption. Sterigmatocystin belongs to the family of Sterigmatocystins. These are phenolic compounds whose structure is based on the sterigmatocystin skeleton, a polycyclic aromatic moiety characterized by a furo[3',2':4,5]furan fused to a xanthen-7-one. 10048-13-2 5284457 C18H12O6 White powder. 246°C Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Sterigmatocystin's carcinogenic properties are a result of its ability to form guanyl DNA adducts and bind to DNA. In addition, DNA adduct formation causes enhanced production of reactive oxygen species and an imbalance in antioxidant defense, leading to enhanced lipid peroxidation that causes cell damage. (A2888, A2958, A2959) The major urinary metabolite is identified as sterigmatocystin-beta-d-glucuronide. Another metabolite is 1,2-dihydro-2-(N7-guanyl)-1-hydroxysterigmatocystin. (A2889, A2890) LD50: 166 mg/kg (Rat, 10 days) (A733) LD50: >800 mg/kg (Mouse) (A733) LD50: 60-65 mg/kg (Intraperitoneal, Rat) (A733) 2B, possibly carcinogenic to humans. (L135) The occurrence of sterigmatocystin in raw materials and foods has not been reported often. The instances reported have usually been on mouldy, or poor quality materials such as wheat, maize, animal feed, hard cheese, pecan nuts and green coffee beans. (L1946) Sterigmatocystin is considered as a potent carcinogen, mutagen and teratogen. It causes necrosis of the liver and kidney. May also cause hepatocellular carcinoma, acute hepatitis, Reye's syndrome, bile duct cell proliferation, periportal fibrosis, hemorrhages, mucous membrane jaundice, fatty liver changes, cirrhosis in malnourished children, and kwashiorkor. (A704, L1946) The first clinical symptoms are anorexia and weight loss. It can also cause diarrhea. (A704, L1946) Phenobarbital may be administered to enhances hepatic transformation activities and protect against Sterigmatocystin-induced toxicity, carcinogenicity and DNA binding in vivo. In cases of ingestion, feeding large quantities of an adsorbent such as activated charcoal may be used. The hepatic function should be monitored. (A704) 2009-12-22T22:31:14Z 2026-04-03T09:13:56Z CYP3A4 CYP3A7 CYP2W1 (A2889, A2890) http://en.wikipedia.org/wiki/Sterigmatocystin C00961 18227 true COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2 C18H12O6 InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3 UTSVPXMQSFGQTM-UHFFFAOYSA-N 324.2843 324.063388116 Endogenous Solid HMDB30588 4447522 CHEM002632 DTXSID2021280 NS00021429 74.22000000000001 83.7026 31.50872591631195 1 5 1 8.382688883759405 -3.701431358515738 0 5 2.73 -3.27 1.74e-01 g/l