Alternariol
Alternariol is a mycotoxin initially produced by species of Alternaria. Alternariol produces a weak estrogenic response in vitro and increases production of estradiol and progesterone. Alternariol is also cytotoxic; in macrophages, it increases DNA base oxidations and strand breaks. Also in macrophages, alternariol increases levels of cyclin B1 and p-cdc2, inducing G2/M phase cell cycle arrest. This compound also increases expression of DNA polymerase β through alterations in PKA-CREB signaling. Additionally, alternariol inhibits topoisomerase I and II, preventing DNA relaxation and cleavage. Warning: Highly toxic. May be mutagenic.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18837623
| Cas No. |
641-38-3 |
|---|---|
| Purity |
≥98% |
| Formula |
C14H10O5 |
| Formula Wt. |
258.23 |
| Chemical Name |
3,4,4-Trihydroxy-6-methyl-2-biphenylcarboxylic acid, gamma lactone |
| IUPAC Name |
3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one |
| Solubility |
Soluble in DMSO, ethanol and methanol, |
| Appearance |
Light blue-green powder |
Frizzell C, Ndossi D, Kalayou S, et al. An in vitro investigation of endocrine disrupting effects of the mycotoxin alternariol. Toxicol Appl Pharmacol. 2013 Aug 15;271(1):64-71. PMID: 23665424.
Solhaug A, Holme JA, Haglund K, et al. Alternariol induces abnormal nuclear morphology and cell cycle arrest in murine RAW 264.7 macrophages. Toxicol Lett. 2013 May 10;219(1):8-17. PMID: 23454835.
Broggi L, Reynoso C, Resnik S, et al. Occurrence of alternariol and alternariol monomethyl ether in beverages from the Entre Rios Province market, Argentina. Mycotoxin Res. 2013 Feb;29(1):17-22. PMID: 23334721.
Scott PM, Zhao W, Feng S, et al. Alternaria toxins alternariol and alternariol monomethyl ether in grain foods in Canada. Mycotoxin Res. 2012 Nov;28(4):261-6. PMID: 23087499.
Solhaug A, Vines LL, Ivanova L, et al. Mechanisms involved in alternariol-induced cell cycle arrest. Mutat Res. 2012 Oct-Nov;738-739:1-11. PMID: 23031795.
Zhao J, Liu K, Lu J, et al. Alternariol induces DNA polymerase β expression through the PKA-CREB signaling pathway. Int J Oncol. 2012 Jun;40(6):1923-8. PMID: 22406678.
Fehr M, Pahlke G, Fritz J, et al. Alternariol acts as a topoisomerase poison, preferentially affecting the IIalpha isoform. Mol Nutr Food Res. 2009 Apr;53(4):441-51. PMID: 18727009.
