Alternariol

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| PIN=3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one

| OtherNames=3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one

|Section1={{Chembox Identifiers

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| InChI = 1/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-UHFFFAOYAX

| SMILES1 = Cc1cc(cc2c1c3cc(cc(c3c(=O)o2)O)O)O

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| ChEBI = 64983

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| ChEMBL = 519982

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| StdInChI = 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

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| CASNo=641-38-3

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Alternariol (commonly abbreviated as AOH) is a toxic metabolite of Alternaria fungi.{{cite journal |vauthors =Davis VM, Stack ME |title=Evaluation of alternariol and alternariol methyl ether for mutagenic activity in Salmonella typhimurium |journal=Appl. Environ. Microbiol. |volume=60 |issue=10 |pages=3901–2 |date=1 October 1994|doi=10.1128/AEM.60.10.3901-3902.1994 |pmid=7986060 |url= |pmc=201908 |bibcode=1994ApEnM..60.3901D }} It is an important contaminant in cereals and fruits.{{cite journal |vauthors =Brugger EM, Wagner J, Schumacher DM |title=Mutagenicity of the mycotoxin alternariol in cultured mammalian cells |journal=Toxicol. Lett. |volume=164 |issue=3 |pages=221–30 |year=2006 |pmid=16464542 |doi=10.1016/j.toxlet.2006.01.001|display-authors=etal}}

Alternariol exhibits antifungal and phytotoxic activity. It is reported to inhibit cholinesterase enzymes.[http://www.fermentek.com/Alternariol Alternariol] product page from Fermentek It is also a mycoestrogen.

A 2017 in vitro assay study reported alternariol to be a full androgen agonist.{{cite journal|last1=Stypuła-Trębas|first1=Sylwia|last2=Minta|first2=Maria|last3=Radko|first3=Lidia|last4=Jedziniak|first4=Piotr|last5=Posyniak|first5=Andrzej|title=Nonsteroidal mycotoxin alternariol is a full androgen agonist in the yeast reporter androgen bioassay|journal=Environmental Toxicology and Pharmacology|volume=55|year=2017|pages=208–211|issn=1382-6689|doi=10.1016/j.etap.2017.08.036|pmid=28910742|bibcode=2017EnvTP..55..208S }}

The acute toxicity of AOH and AME is low, but in vitro the substances show a strong mutagenic and teratogenic effect. The substances are associated with the development of esophageal cancer.{{cite journal |vauthors =Saleh I, Zeidan R, Abu-Dieyeh M |title=The characteristics, occurrence, and toxicological effects of alternariol: a mycotoxin |journal=Arch Toxicol |volume=98|year=2024|issue=6|pages=1659–1683|doi=10.1007/s00204-024-03743-0|PMID=38662238|url=https://pubmed.ncbi.nlm.nih.gov/38662238/|hdl=10576/56642|hdl-access=free}}