Letter | Published:

Decomposition and Carcinogenic Activity of Azoxyglycosides

Naturevolume 207page632 (1965) | Download Citation

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Abstract

THE toxicity of leaves and seeds of cycads to animals and humans is well established (for review, see ref. 1). The toxic constituents are azoxyglycosides of which the simplest are cycasin (I; R = β-D-glucopyranosyl)2 and macrozamin (I; R = β-primeverosyl)3,4. More recently, liver damage5 and carcinogenesis6 have been observed to follow ingestion of the seeds or extracts containing the unstable aglycone, methylazoxymethanol (I; R = H) (ref. 5). The latter may theoretically decompose to the alkylating agent, diazomethane, a potent carcinogen7, and is indeed isomeric with hydroxydimethylnitrosamine through which dimethylnitrosamine may be transformed in vivo to the same active carcinogen8.

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References

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Affiliations

  1. Department of Organic Chemistry, University of New England, Armidale, New South Wales

    • N. V. RIGGS

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https://doi.org/10.1038/207632a0

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