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Alternariol

From Wikipedia, the free encyclopedia

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.164.145Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: CEBXXEKPIIDJHL-UHFFFAOYSA-N checkY
  • 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
  • CC1=CC(=CC2=C1C3=CC(=CC(=C3C(=O)O2)O)O)O
  • Cc1cc(cc2c1c3cc(cc(c3c(=O)o2)O)O)O
Properties
C14H10O5
Molar mass258.229 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Alternariol (commonly abbreviated as AOH) is a toxic metabolite ofAlternaria fungi.[1] It is an important contaminant in cereals and fruits.[2]Alternariol exhibitsantifungal andphytotoxic activity. It is reported to inhibitcholinesterase enzymes.[3] It is also amycoestrogen.

A 2017in vitroassay study reported alternariol to be afullandrogen agonist.[4]

The acute toxicity of AOH and AME is low, but in vitro the substances show a strongmutagenic andteratogenic effect. The substances are associated with the development of esophagealcancer.[5]

References

[edit]
  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 fromFermentek
  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.Bibcode:2024ArTox..98.1659S.doi:10.1007/s00204-024-03743-0.hdl:10576/56642.PMC 11106155.PMID 38662238.
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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