Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H12O7 |
Molecular Weight | 328.273 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12OC=C[C@@]1(O)C3=C(O2)C=C(OC)C4=C3OC(=O)C5=C4CCC5=O
InChI
InChIKey=MJBWDEQAUQTVKK-IAGOWNOFSA-N
InChI=1S/C17H12O7/c1-21-9-6-10-13(17(20)4-5-22-16(17)23-10)14-12(9)7-2-3-8(18)11(7)15(19)24-14/h4-6,16,20H,2-3H2,1H3/t16-,17-/m1/s1
AFLATOXIN M1 is a 4-hydroxylated metabolite of AFLATOXIN B1, one of the MYCOTOXINS from ASPERGILLUS tainted food. It is associated with liver damage and cancer resulting from its P450 activation to the epoxide which alkylates DNA. Toxicity depends on the balance of liver enzymes that activate it (CYTOCHROME P-450) and others that detoxify it (GLUTATHIONE S TRANSFERASE). Primates and rat are sensitive while mouse and hamster are tolerant. Aflatoxin M1 (AFM1) is associated with carcinogenicity, genotoxicity, mutagenicity, and teratogenicity and as a result, represents a human health problem worldwide.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Glycine N-methyltransferase affects the metabolism of aflatoxin B1 and blocks its carcinogenic effect. | 2009 Mar 15 |
|
Cloning, expression and functional characterization of cytochrome P450 3A37 from turkey liver with high aflatoxin B1 epoxidation activity. | 2010 Aug 16 |
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Metabolism of aflatoxin B1 in turkey liver microsomes: the relative roles of cytochromes P450 1A5 and 3A37. | 2011 Aug 1 |
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Aflatoxins upregulate CYP3A4 mRNA expression in a process that involves the PXR transcription factor. | 2011 Aug 28 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: ftp://ftp.fao.org/codex/meetings/CCFAC/CCFAC33/56th%20JECFA%20Summary.pdf
Curator's Comment: Rats: groups of Fischer rats were maintained on diets containing natural aflatoxin M1 at 0, 0.5, 5, or 50 ug/kg and were killed between 18 and 22 months. Hepatocellular carcinomas were detected in 5% and neoplastic nodules in 15% of rats fed diets containing aflatoxin M1 at 50 ug/kg between 19 and 20 months. http://www.inchem.org/documents/jecfa/jecmono/v47je02.htm
The intake of aflatoxin M1 from milk was calculated to be 6.8 ng/person per day for the European diet, 3.5 ng/person per day for the Latin American diet, 12 ng/person
per day for the Far Eastern diet, 0.7 ng/person per day for the Middle Eastern diet, and 0.1 ng/person per
day for the African diet. Intake calculated from the European regional diet was used for the assessment
of cancer risk because this diet had the highest milk consumption. If all milk consumed were
contaminated with aflatoxin M1 at the proposed maximum levels of 0.05 µg/kg or 0.5 µg/kg, the intake of
aflatoxin M1 from milk in the European regional diet would be 15 ng/person per day or 150 ng/person per
day, respectively.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6802733
The lowest toxic dose of Aflatoxin M1 (AFM1) was 0.6 ug per adult-rat hepatocytes culture. The lowest genotoxic dose of AFM1 was 0.05 ug/culture.
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6795-23-9
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Aflatoxin M1
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SUBSTANCE RECORD