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Alternariol.

ABSTRACT:

In the title compound (systematic name

3,7,9-trihydr-oxy-1-methyl-6H-benzo[c]chromen-6-one), C(14)H(10)O(5), the methyl group is shifted out of the molecular plane due to a steric collision, thus causing a slight twist of the benzene rings. The mol-ecular structure is stabilized by an intra-molecular O-H?O hydrogen bond, generating an S(6) ring. In the crystal, mol-ecules are connected by inter-molecular O-H?O hydrogen bonds into a three-dimensional network.

SUBMITTER: Siegel D

PROVIDER: S-EPMC2979420 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Alternariol.

Siegel David D Troyanov Sergey S Noack Johannes J Emmerling Franziska F Nehls Irene I

Acta crystallographica. Section E, Structure reports online 20100515 Pt 6

<h4>In the title compound (systematic name</h4>3,7,9-trihydr-oxy-1-methyl-6H-benzo[c]chromen-6-one), C(14)H(10)O(5), the methyl group is shifted out of the molecular plane due to a steric collision, thus causing a slight twist of the benzene rings. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond, generating an S(6) ring. In the crystal, mol-ecules are connected by inter-molecular O-H⋯O hydrogen bonds into a three-dimensional network. ...[more]

PMID: 21579450

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Alternariol 9-O-methyl ether.

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Identification of a polyketide synthase required for alternariol (AOH) and alternariol-9-methyl ether (AME) formation in Alternaria alternata.

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Alternariol exerts embryotoxic and immunotoxic effects on mouse blastocysts through ROS-mediated apoptotic processes.

Project description:Alternariol (AOH), a mycotoxin belonging to the genus Alternaria, has been shown to induce cytotoxicity, including apoptosis and cell cycle arrest, in several mammalian cell types. However, its effects on early-stage embryonic development require further investigation. Here, we have shown that AOH exerts embryotoxic effects on mouse blastocyst-stage embryos and long-term adverse effects on immunity in one-day-old newborn mice of the next generation. Significant apoptosis and decrease in total cell number, predominantly through loss of inner cell mass (ICM), and to a minor extent, trophectoderm (TE) cells, were observed in AOH-treated blastocysts. Moreover, AOH exerted detrimental effects on pre- and post-implantation embryo development potential and induced a decrease in fetal weight in in vitro development and embryo transfer assays. Injection of pregnant mice with AOH (1, 3 and 5 mg/kg body weight/day) for 4 days resulted in apoptosis of blastocyst-stage embryos and injurious effects on embryonic development from the zygote to blastocyst stage or embryo degradation and a further decrease in fetal weight. Furthermore, AOH exerted a long-term impact on the next generation, triggering a significant increase in total oxidative stress content and expression of genes encoding antioxidant proteins. Lower expression of CXCL1, IL-1β and IL-8 related to innate immunity was detected in liver tissue extracts obtained from one-day-old newborns of AOH-injected pregnant mice (5 mg/kg body weight/day) relative to their non-treated counterparts. In addition, ROS served as an upstream regulator of AOH-triggered apoptotic processes and impairment of embryonic development. Our collective results highlight the potential of AOH as an embryotoxic and immunotoxic risk factor during embryo and infant development stages in mice.

| S-EPMC8403814 | biostudies-literature

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