Alternariol

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 (commonly abbreviated as AOH) and his monomethylether AME 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.

A 2017 in vitro assay study reported alternariol to be a full androgen agonist. ^[4]

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 ^[5] .

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. Bibcode:1994ApEnM..60.3901D. doi:10.1128/AEM.60.10.3901-3902.1994. 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 S, Minta M, Radko L, Jedziniak P, Posyniak A (2017). "Nonsteroidal mycotoxin alternariol is a full androgen agonist in the yeast reporter androgen bioassay". Environmental Toxicology and Pharmacology. 55: 208–211. Bibcode:2017EnvTP..55..208S. doi:10.1016/j.etap.2017.08.036. ISSN   1382-6689. PMID   28910742.
5. Saleh I, Zeidan R, Abu-Dieyeh M (2024). "The characteristics, occurrence, and toxicological effects of alternariol: a mycotoxin". Arch Toxicol. 98 (6): 1659–1683. doi:10.1007/s00204-024-03743-0. PMID   38662238.