Methylation of deoxyribonucleic acid in the rat by the mushroom poison gyromitrin

Gyromitrin (acetaldehyde N-methyl-N-formylhydrazone) is the most preponderant of a group of hydrazone compounds found in the false morel mushroom Gyromitra esculenta . It decomposes to products considered to be metabolized to methylating agents in vivo. (N-methyl- super(3)H)Gyromitrin was synthesize...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1983-09, Vol.31 (5), p.1117-1120
Main Authors: Meier-Bratschi, Annelis, Carden, Brian M, Luethy, Juerg, Lutz, Werner K, Schlatter, Christian
Format: Article
Language:English
Subjects:
Acetaldehyde - administration & dosage
Acetaldehyde - analogs & derivatives
Animals
Basidiomycota
Carcinogens - administration & dosage
DNA - metabolism
Dose-Response Relationship, Drug
Liver - metabolism
Lung - metabolism
Male
Methylation
Models, Biological
Mycotoxins - administration & dosage
Rats
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Summary:Gyromitrin (acetaldehyde N-methyl-N-formylhydrazone) is the most preponderant of a group of hydrazone compounds found in the false morel mushroom Gyromitra esculenta . It decomposes to products considered to be metabolized to methylating agents in vivo. (N-methyl- super(3)H)Gyromitrin was synthesized from formylhydrazine by reaction with acetaldehyde in absolute alcohol and methylation of the resulting hydrazone with tritiated methyl iodide in tetrahydrofuran. ( super(3)H)Gyromitrin was administered orally to young adult male rats. After 6 h, DNA was isolated from liver and lung. Although all DNA samples were radiolabeled, analysis by HPLC of the purines liberated from the DNA upon acid hydrolysis revealed that only liver DNA contained 7-methylguanine as a result of DNA methylation. Most radioactivity coeluted with the natural purines and was the result of biosynthetic incorporation of radiolabeled breakdown products of gyromitrin. Expressed as DNA damage per dose in the units of a Covalent Binding Index, CBI, gyromitrin exhibited an average value of 15 for liver DNA, while the respective value for lung (CBI < 5) was below our limit of detection. Upon comparison with the unavoidable intake of the methylating carcinogen dimethylnitrosamine (CBI = 6000), it is concluded that the false morel mushroom should only be consumed occasionally.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf00119a048