Alternariol

Alternariol is a toxic metabolite of Alternaria fungi.[1] It is an important contaminant in cereals and fruits.[2] Alternariol exhibits antifungal and phytotoxic activity. It is reported to inhibit cholinesterase enzymes.[3] It is also a mycoestrogen.

Alternariol

Names
Preferred IUPAC name 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
Other names 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one
Identifiers
CAS Number	641-38-3^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:64983^N
ChEMBL	ChEMBL519982^Y
ChemSpider	4514301^Y
ECHA InfoCard	100.164.145
KEGG	C16838^Y
PubChem CID	5359485
UNII	KN9L4260JW^Y
CompTox Dashboard (EPA)	DTXSID80214305
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^Y Key: CEBXXEKPIIDJHL-UHFFFAOYSA-N^Y 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 Key: CEBXXEKPIIDJHL-UHFFFAOYAX
SMILES CC1=CC(=CC2=C1C3=CC(=CC(=C3C(=O)O2)O)O)O Cc1cc(cc2c1c3cc(cc(c3c(=O)o2)O)O)O
Properties
Chemical formula	C14H10O5
Molar mass	258.229 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Alternariol is reported to be a full androgen agonist in an in vitro assay.[4]

References

1. Davis VM, Stack ME (1 October 1994). "Evaluation of alternariol and alternariol methyl ether for mutagenic activity in Salmonella typhimurium". Appl. Environ. Microbiol. 60 (10): 3901–2. PMC 201908. PMID 7986060.
2. Brugger EM, Wagner J, Schumacher DM, et al. (2006). "Mutagenicity of the mycotoxin alternariol in cultured mammalian cells". Toxicol. Lett. 164 (3): 221–30. doi:10.1016/j.toxlet.2006.01.001. PMID 16464542.
3. Alternariol product page from Fermentek
4. Stypuła-Trębas, Sylwia; Minta, Maria; Radko, Lidia; Jedziniak, Piotr; Posyniak, Andrzej (2017). "Nonsteroidal mycotoxin alternariol is a full androgen agonist in the yeast reporter androgen bioassay". Environmental Toxicology and Pharmacology. 55: 208–211. doi:10.1016/j.etap.2017.08.036. ISSN 1382-6689.