3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE

Description

Alternariol is a mycotoxin, a toxic secondary fungal metabolite, produced by Alternaria molds. It is cytotoxic, fetotoxic, teratogenic, mutagenic, and genotoxic. It induces cytochrome P450 1A1 expression and apoptosis in mouse hepatoma cells (20-40 μM). Alternariol, whose synthesis is inhibited by light, naturally occurs on fruits, vegetables, and cereals, such as apples, tomatoes, and wheat.

Uses

An alternaria mycotoxin and genotoxin, found in common edible crops. It inhibits the activity of various DNA-topoisomerases, increasing he rate of DNA strand breaks.

Uses

Alternariol from Alternaria sp. may be used as a calibration standard in reverse phase high-performance liquid chromatography (HPLC) and UV-spectrum analysis. It may also be used to spike wholemeal wheat flour for wet baking studies

Definition

ChEBI: A benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alt rnaria species, which are the most common mycoflora infecting small grain cereals worldwide.

Synthesis Reference(s)

The Journal of Organic Chemistry, 70, p. 3275, 2005 DOI: 10.1021/jo050075r

General Description

Alternariol belongs to the dibenzo-pyrones chemical group. It is a mycotoxin present in indoor air, soil and plants.

Biochem/physiol Actions

Alternaria mycotoxins are generally associated with undried food grains post-harvest. The disease caused by Alternaria mycotoxin results in a discolored halo in fruits and spotting in leaves. Alternariol (AOH) is cytotoxic and fetotoxic to microbes and mammalian cells. AOH displays inhibitory effect on cell proliferation and has estrogenic functionality.

References

[1] tiemann u, tomek w, schneider f, et al. the mycotoxins alternariol and alternariol methyl ether negatively affect progesterone synthesis in porcine granulosa cells in vitro[j]. toxicology letters, 2009, 186(2): 139-145.
[2] sderhll k, svensson e, unestam t. light inhibits the production of alternariol and alternariol monomethyl ether in alternaria alternata[j]. applied and environmental microbiology, 1978, 36(5): 655-657.
[3] schreck i, deigendesch u, burkhardt b, et al. the alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome p450 1a1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbon receptor[j]. archives of toxicology, 2012, 86(4): 625-632.