For research use only. Not for therapeutic Use.
Sterigmatocystin（Cat No.:R058417）is a mycotoxin produced by certain Aspergillus and Penicillium species, structurally related to aflatoxins. It is a potent secondary metabolite known for its toxicological and carcinogenic properties. Sterigmatocystin inhibits DNA, RNA, and protein synthesis by intercalating into DNA, leading to cellular damage and oxidative stress. It is widely studied in toxicology to understand its role in food contamination and its effects on human and animal health. Additionally, sterigmatocystin serves as a model compound for exploring mycotoxin biosynthesis, mechanisms of toxicity, and developing detection and mitigation strategies.
| Catalog Number | R058417 |
| CAS Number | 10048-13-2 |
| Synonyms | (3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3’,2’:4,5]furo[2,3-c]xanthen-7-one; 3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3’,2’:4,5]furo[2,3-c]xanthen-7-one; (3aR-cis)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3’,2’:4,5]furo[2,3-c]xanthen |
| Molecular Formula | C18H12O6 |
| Purity | ≥95% |
| Target | Anti-infection |
| Storage | -20°C |
| IUPAC Name | (3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one |
| InChI | 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/t8-,18+/m0/s1 |
| InChIKey | UTSVPXMQSFGQTM-DCXZOGHSSA-N |
| SMILES | COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=CC=CC(=C5C2=O)O |
| Reference | Studies in the biochemistry of micro-organisms. 99. Metabolic products of Aspergillus versicolor (Vuillemin) Tiraboschi. Birkinshaw J.H. & Hammady I.M.M., Biochem. J. 1957, 65, 162.<br/><br/>Sterigmatocystin-DNA interactions: Identification of a major adduct formed after metabolic activation in vitro. Essigmann J.M., Proc. Nat. Acad. Sci. USA 1979, 76, 179.<br/><br/>Inhibitory effect of sterigmatocystin and 5,6-dimethoxysterigmatocystin on ATP synthesis in mitochondria. Kawai K. et al. , Appl. Environ. Microbiol. 1984, 48, 1001.<br/><br/>Selective inhibition of acyl-CoA:cholesterol acyltransferase 2 isozyme by flavasperone and sterigmatocystin from Aspergillus species. Sakai K.J., Antibiot. 2008, 61, 568.</span></p> |
