13191-64-5
Chemical Structure
Aurofusarin
- CAS No.: 13191-64-5
- Formula:C30H18O12
- Molecular Weight:570.46
IUPAC Name: 5,5'-dihydroxy-8,8'-dimethoxy-2,2'-dimethyl-4H,4'H-[7,7'-bibenzo[g]chromene]-4,4',6,6',9,9'-hexaone
InChIKey: VSWWTKVILIZDGX-UHFFFAOYSA-N
SMILES: O=C(C=C(C)O1)C(C1=C2)=C(O)C(C(C(C(C(C3=C4C=C5C(C(C=C(C)O5)=O)=C3O)=O)=C(OC)C4=O)=C6OC)=O)=C2C6=O
Biological Activity: Aurofusarin is a secondary metabolite. Aurofusarin catalytically inhibits topoisomerase II alpha, induces CYP1A1, p53, oxidative stress, DNA damage, and glutathione redox shift, intercalates into DNA, and causes S phase reduction accompanied by cytoskeletal/nuclear condensation. Aurofusarin disrupts intestinal epithelial barrier integrity, acts additively with deoxynivalenol, reduces mitochondrial activity, is cytotoxic to colon cells, and inhibits probiotic Gram-positive bacteria through outer membrane penetration without affecting Gram-negative bacteria. Aurofusarin can be used in research on colon cancer and bacterial infections[1][2][3][4][5][6][7][8].
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Aurofusarin | Aurofusarin is a secondary metabolite. Aurofusarin catalytically inhibits topoisomerase II alpha, induces CYP1A1, p53, oxidative stress, DNA damage, and glutathione redox shift, intercalates into DNA, and causes S phase reduction accompanied by cytoskeletal/nuclear condensation. Aurofusarin disrupts intestinal epithelial barrier integrity, acts additively with deoxynivalenol, reduces mitochondrial activity, is cytotoxic to colon cells, and inhibits probiotic Gram-positive bacteria through outer membrane penetration without affecting Gram-negative bacteria. Aurofusarin can be used in research on colon cancer and bacterial infections. | |||||||||||||||||||||
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References
- [1]. Xu Y, et al. Bis-naphthopyrone pigments protect filamentous ascomycetes from a wide range of predators. Nature communications. 2019 Aug 08;10(1):3579.
- [2]. Springler A, et al. Effect of Fusarium-Derived Metabolites on the Barrier Integrity of Differentiated Intestinal Porcine Epithelial Cells (IPEC-J2). Toxins. 2016 Nov 19;8(11):345.
- [3]. Jarolim K, et al. The secondary Fusarium metabolite aurofusarin induces oxidative stress, cytotoxicity and genotoxicity in human colon cells. Toxicology letters. 2018 Mar 01;284:170-183.
- [4]. Sørensen JL, et al. Influence of carbohydrates on secondary metabolism in Fusarium avenaceum. Toxins. 2013 Sep 24;5(9):1655-63.
- [5]. Sondergaard TE, et al. Fast Screening of Antibacterial Compounds from Fusaria. Toxins. 2016 Nov 29;8(12):355.
- [6]. Malz S, et al. Identification of a gene cluster responsible for the biosynthesis of aurofusarin in the Fusarium graminearum species complex. Fungal genetics and biology : FG & B. 2005 May;42(5):420-33.
- [7]. Dvorska JE, et al. Effect of the mycotoxin aurofusarin on the antioxidant composition and fatty acid profile of quail eggs. British poultry science. 2001 Dec;42(5):643-9.
- [8]. Vejdovszky K, et al. Non-synergistic cytotoxic effects of Fusarium and Alternaria toxin combinations in Caco-2 cells. Toxicology letters. 2016 Jan 22;241:1-8.
