Alternariol
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| Names | |
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| 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) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.164.145 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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Alternariol (commonly abbreviated as AOH) 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
[edit]- ↑ 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.
- ↑ 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.
- ↑ Alternariol product page from Fermentek
- ↑ 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.
- ↑ 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.