Neurotoxins in a Vetch Food: Stability to Cooking and Removal of γ-Glutamyl-β-cyanoalanine and β-Cyanoalanine and Acute Toxicity from Common Vetch (Vicia sativa L.) Legumes

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 1, 1997, Pages 189-194

  Ressler, Charlotte ^a   Tatake, Jayant G ^a   Kaizer, Ellen ^a   Putnam, Daniel H ^b  

^a UNIVERSITY OF CONNECTICUT HEALTH CENTER   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Chicks; Common vetch; Detoxification; Food toxins; Legumes; Nutrition; Pyroglutamic acid; Vicia sativa L; cyanoalanine; glutamyl cyanoalanine

Indexed keywords

VICIA; VICIA SATIVA SUBSP. NIGRA;

EID: 0000430783     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9603745     Document Type: Article

References (25)

1. Allen, G. Methods for the detection of peptides. In Sequencing of Proteins and Peptides; R. H. Burden, P. H. van Knippenberg, Eds.; Elsevier: New York, 1989; pp 194-195.
2. Arscott, G. H.; Harper, J. A. Relationship of 2,5-Diamino-4,6-diketopyrimidine, 2,4-Diaminobutyric Acid and a Crude Preparation of β-Cyano-L-alanine to the Toxicity of Common and Hairy Vetch Seed Fed to Chicks. J. Nutr. 1963, 80, 251-254.
3. Bell, E. A.; Tirimanna, A. S. L. Associations of Amino Acids and Related Compounds in the Seeds of Forty-seven Species of Vicia: Their Taxonomic and Nutritional Significance. Biochem. J. 1965, 97, 104-111.
4. Bhat, R. V.; Raghuram, T. C. Health and economic implications of imported toxic legumes. Curr. Sci. 1993, 65, 12-13.
5. Binkley, F.; Fugii, S.; Kimmel, J. R. Metabolism of glutathione II. Determination of glutathione and products of its hydrolysis in blood. J. Biol. Chem. 1950, 159-162.
6. Brown, E. G. Coping with toxic pulses. Nature 1992, 360, 9.
7. Cohen, S. A.; Meys, M.; Tarvin, T. L. The Pico-Tag Method, A Manual of Advanced Techniques for Amino Acid Analysis; Rev. 1; Waters Chromatograph Division, 34 Maple St., Milford, MA 01757, 1989; Publication WM02, pp 18-19.
8. Coon, J. M. Toxicology of Natural Food Chemicals: A Perspective. In Toxicants Occurring Naturally in Foods; National Academy of Sciences: Washington, DC, 1973; pp 579-580.
9. Falasca, A.; Franceschi, C.; Rossi, C. A.; Stirpe, F. Purification and Partial Characterization of a Mitogenic Lectin from Vicia sativa. Biochim. Biophys. Acta 1979, 577, 71-81.
10. Furst, P.; Pollack, T. A.; Godel, H.; Stehle, P. Appraisal of four pre-column derivatization methods for the high-performance liquid chromatographic determination of free amino acids in biological materials. J. Chromatogr. 1990, 499, 557-569.
11. Greenstein, J. P.; Winitz, M. Chemistry of the Amino Acids; Wiley: New York, 1961; Vol. 3, pp 1940-1941.
12. Harper, J. A.; Arscott, G. H. Toxicity of common and hairy vetch seeds for poults and chicks. Poult. Sci. 1962, 41, 1968-1974.
13. LeQuesne, W. J.; Young, G. T. The autohydrolysis of glutamyl-peptides. J. Chem. Soc. (London) 1952, 594-597.
14. Liener, I. E. The Nutritional Significance of the Plant Lectins. In Antinutrients and Natural Toxicants in Foods; Ory, R. L., Ed.; Food & Nutrition Press: Westport, CT, 1981; pp 143-153.
15. Marquardt, R. R. Vicine, Convicine, and their Aglycones-Divicine and Isouramil. In Toxicants of Plant Origin, Vol. 2, Glycosides; Cheeke, P. R., Ed.; CRC Press: Boca Raton, FL, 1988.
16. Pitz, W. J.; Sosulski, F. W.; Hogge, L. R. Occurrence of Vicine and Convicine in Seeds of Some Vicia Species and Other Pulses. Can. Inst. Food Sci. Technol. J. 1980, 13, 35-39.
17. Putnam, D.; Breene, W.; Somers, D. Vetching Vetch. BioOptions 1994, 4 (3), 8.
18. Ressler, C.; Nigam, S. N.; Giza, Y.-H.; Nelson, J. Isolation and Identification from Common Vetch of γ-L-Glutamyl-β-cyano-L-alanine, a Bound Form of the Neurotoxin β-Cyano-L-alanine. J. Am. Chem. Soc. 1963, 85, 3311-3312.
19. Ressler, C.; Nelson, J.; Pfeffer, M. Metabolism of β-Cyanoalanine. Biochem. Pharmacol. 1967, 16, 2309-2319.
20. Ressler, C.; Nigam, S. N.; Giza, Y.-H. Toxic principle in vetch. Isolation and identification of γ-glutamyl-β-cyanoalanine from common vetch seeds. Distribution in some legumes. J. Am. Chem. Soc. 1969, 91, 2758-2765.
21. Ressler, C.; Ratzkin, H. Synthesis of β-cyano-L-alanine and γ-cyano-α-L-aminobutyric acid, dehydration products of L-asparagine and L-glutamine: A new synthesis of amino acid nitriles. J. Org. Chem. 1961, 26, 3356-3360.
22. Taste, M. E.; Enneking, D. A mess of red pottage. Nature 1992, 359, 357-358.
23. Vickery, H. B.; Pucher, G. W.; Clark, H. E.; Chibnall, A. C.; Westall, R. G. The Determination of Glutamine in the Presence of Asparagine. Biochem. J. 1935, 2710-2720.
24. Wieland, T. Chemistry and properties of glutathione. In Glutathione, a Symposium; Colowick, S., Lazarow, A., Racker, E., Schwarz, D. R., Stadtman, E., Waelsch, H., Eds.; Academic Press: New York; 1950; pp 48-50.
25. Yang, M. G.; Michaelson, O. Cycads. In Toxic Constituents of Plant Foodstuffs; Liener, I. E., Ed.; Academic Press: New York, 1969; p 161.