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Mandelonitrile beta-glucuronide: synthesis and characterization.

C Fenselau, S Pallante, R P Batzinger

    Science (New York, N.Y.)
    |November 11, 1977
    PubMed
    Summary
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    Laetrile, or mandelonitrile beta-glucuronide, was synthesized and tested. Commercial Laetrile preparations contained amygdalin and neoamygdalin, and both these compounds and mandelonitrile glucuronide were found to be mutagenic.

    Area of Science:

    • Biochemistry
    • Pharmacology
    • Toxicology

    Background:

    • Laetrile, patented as mandelonitrile beta-glucuronide, is a compound investigated for therapeutic properties.
    • The precise composition and potential mutagenicity of Laetrile and its related compounds require thorough scientific evaluation.

    Purpose of the Study:

    • To synthesize and characterize mandelonitrile beta-glucuronide.
    • To analyze the composition of commercial Laetrile preparations.
    • To assess the mutagenic potential of synthesized mandelonitrile beta-glucuronide and related compounds.

    Main Methods:

    • Enzyme immobilization of rabbit liver uridine diphosphate-glucuronosyl transferase on beaded sepharose for synthesis.
    • Analysis using thin-layer chromatography, nuclear magnetic resonance, and gas chromatography-mass spectrometry.

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  • Mutagenicity testing using Salmonella typhimurium strains TA 98 and TA 100.
  • Main Results:

    • Mandelonitrile beta-glucuronide was successfully synthesized.
    • Commercial Laetrile preparations were found to contain amygdalin and neoamygdalin, lacking glucuronide.
    • Mandelonitrile, mandelonitrile glucuronide, and a mixture of amygdalin and neoamygdalin demonstrated mutagenic activity.

    Conclusions:

    • The synthesis and characterization of mandelonitrile beta-glucuronide were achieved.
    • Commercial Laetrile products may not contain the expected glucuronide compound.
    • Mandelonitrile, its glucuronide, and amygdalin/neoamygdalin mixtures exhibit mutagenic properties, raising safety concerns.