A mycotoxin
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Alternariol monomethyl ether

Item No. 11307

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,7-dihydroxy-9-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
CAS Number
23452-05-3
Synonyms
  • AME
  • NSC 638262
Molecular Formula
C15H12O5
Formula Weight
272.3
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleMethanol: soluble
SMILES
CC1=C(C2=C(C(O3)=O)C(O)=CC(OC)=C2)C3=CC(O)=C1
InChi Code
InChI=1S/C15H12O5/c1-7-3-8(16)4-12-13(7)10-5-9(19-2)6-11(17)14(10)15(18)20-12/h3-6,16-17H,1-2H3
InChi Key
LCSDQFNUYFTXMT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Alternariol monomethyl ether (AME) is a mycotoxin originally isolated from A. brassicae extracts. AME is a common contaminant in cereal grains such as wheat, barley, and sorghum that is cytotoxic to bacterial (MIC = 500 μg/disc for B. mycoides in a bacterial halo assay) and mammalian cells (IC50 = 120 μM in HCT116 cells).1,2 It inhibits human topoisomerase II and bacterial gyrase at initial inhibitory concentrations of 25 and 10 μM, respectively. AME selectively inhibits monoamine oxidase A (MOA-A; Ki = 0.34 μM).3,4 AME also provokes DNA damage that induces mitochondrial permeability transition pore-mediated activation of apoptosis.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pero, R.W., Posner, H., Blois, M., et al. Toxicity of metabolites produced by the "Alternaria". Environ. Health Perspect. 4, 87-94 (1973).

    2. Bensassi, F., Gallerne, C., el Dein, O.S., et al. Mechanism of Alternariol monomethyl ether-induced mitochondrial apoptosis in human colon carcinoma cells. Toxicology 290(2-3), 230-240 (2011).

    3. Jarolim, K., Del Favero, G., Ellmer, D., et al. Dual effectiveness of Alternaria but not Fusarium mycotoxins against human topoisomerase II and bacterial gyrase. Arch. Toxicol. 91(4), 2007-2016 (2016).

    4. Lee, H.W., Kim, Y.J., Nam, S.-J., et al. Potent selective inhibition of monoamine oxidase A by alternariol monomethyl ether isolated from Alternaria brassicae. J. Microbiol. Biotechnol. 27(2), 316-320 (2017).