Alternariol

• CAT Number: R013243
• CAS Number: 641-38-3
• Molecular Formula: C14H10O5
• Molecular Weight: 258.229
• Purity: ≥95%
• Synonyms: 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one; NSC 638263
• Target: Topoisomerase
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• IUPAC Name: 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one
• InChI: InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
• InChIKey: CEBXXEKPIIDJHL-UHFFFAOYSA-N
• SMILES: CC1=CC(=CC2=C1C3=CC(=CC(=C3C(=O)O2)O)O)O

Alternariol(CAS 641-38-3) is a mycotoxin, topoisomerase I and II inhibitor and potential ER agonist found in Alternaria.

Reference

1:Microbial Natural Product Alternariol 5-O-Methyl Ether Inhibits HIV-1 Integration by Blocking Nuclear Import of the Pre-Integration Complex. Ding J, Zhao J, Yang Z, Ma L, Mi Z, Wu Y, Guo J, Zhou J, Li X, Guo Y, Peng Z, Wei T, Yu H, Zhang L, Ge M, Cen S.Viruses. 2017 May 10;9(5). pii: E105. doi: 10.3390/v9050105. PMID: 28489061 Free Article
2:Development of an Immunochromatographic Strip Test for the Rapid Detection of Alternariol Monomethyl Ether in Fruit. Man Y, Liang G, Jia F, Li A, Fu H, Wang M, Pan L.Toxins (Basel). 2017 Apr 29;9(5). pii: E152. doi: 10.3390/toxins9050152. PMID: 28468234 Free Article
3:In vitro combinatory effects of the Alternaria mycotoxins alternariol and altertoxin II and potentially involved miRNAs. Vejdovszky K, Sack M, Jarolim K, Aichinger G, Somoza MM, Marko D.Toxicol Lett. 2017 Feb 5;267:45-52. doi: 10.1016/j.toxlet.2016.12.011. Epub 2016 Dec 19. PMID: 28007639 Free Article
4:Development and Validation of a LC-ESI-MS/MS Method for the Determination of Alternaria Toxins Alternariol, Alternariol Methyl-Ether and Tentoxin in Tomato and Tomato-Based Products. Rodríguez-Carrasco Y, Mañes J, Berrada H, Juan C.Toxins (Basel). 2016 Nov 11;8(11). pii: E328. PMID: 27845716 Free PMC Article
5:Potent Selective Inhibition of Monoamine Oxidase A by Alternariol Monomethyl Ether Isolated from Alternaria brassicae. Lee HW, Kim YJ, Nam SJ, Kim H.J Microbiol Biotechnol. 2017 Feb 28;27(2):316-320. doi: 10.4014/jmb.1610.10053. PMID: 27840401 Free Article
6:Sulfoglucosides as Novel Modified Forms of the Mycotoxins Alternariol and Alternariol Monomethyl Ether. Soukup ST, Kohn BN, Pfeiffer E, Geisen R, Metzler M, Bunzel M, Kulling SE.J Agric Food Chem. 2016 Nov 23;64(46):8892-8901. Epub 2016 Nov 15. PMID: 27776211
7:Combinatory estrogenic effects between the isoflavone genistein and the mycotoxins zearalenone and alternariol in vitro. Vejdovszky K, Schmidt V, Warth B, Marko D.Mol Nutr Food Res. 2017 Mar;61(3). doi: 10.1002/mnfr.201600526. Epub 2016 Dec 19. PMID: 27739238
8:Genistein and delphinidin antagonize the genotoxic effects of the mycotoxin alternariol in human colon carcinoma cells. Aichinger G, Beisl J, Marko D.Mol Nutr Food Res. 2017 Feb;61(2). doi: 10.1002/mnfr.201600462. Epub 2016 Oct 14. PMID: 27628123
9:Effect of 1-methylcyclopropene on the development of black mold disease and its potential effect on alternariol and alternariol monomethyl ether biosynthesis on tomatoes infected with Alternaria alternata. Estiarte N, Crespo-Sempere A, Marín S, Sanchis V, Ramos AJ.Int J Food Microbiol. 2016 Nov 7;236:74-82. doi: 10.1016/j.ijfoodmicro.2016.07.001. Epub 2016 Jul 4. PMID: 27454782
10:Impact of phase I metabolism on uptake, oxidative stress and genotoxicity of the emerging mycotoxin alternariol and its monomethyl ether in esophageal cells. Tiessen C, Ellmer D, Mikula H, Pahlke G, Warth B, Gehrke H, Zimmermann K, Heiss E, Fröhlich J, Marko D.Arch Toxicol. 2017 Mar;91(3):1213-1226. doi: 10.1007/s00204-016-1801-0. Epub 2016 Jul 15. PMID: 27422292 Free PMC Article