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Vicianin, prunasin, and beta-cyanoalanine in common vetch seed as sources of urinary thiocyanate in the rat.

Abstract
When young rats were fed a diet containing common vetch seed for 1 month, they excreted in the urine approximately 7 times more thiocyanate than they had ingested. Vicianin, prunasin, and beta-cyanoalanine were identified as principal dietary sources of the excreted thiocyanate. Vicianin was isolated by chromatography and crystallization. Its structure was confirmed by mass spectrometry and by identification of its monosaccharides and aglycon. Prunasin was identified chromatographically by HPLC. The combined seed content of vicianin (0.68 micromol/g) and prunasin (0.16 micromol/g) corresponded to the cyanogen content of the seed (0.91 +/- 0.14 micromol/g; n = 7), determined as cyanide after autolysis. When vicianin was fed, the urinary thiocyanate output was 21% of the ingested amount of vicianin, whereas beta-cyanoalanine yielded a urinary thiocyanate output of < 0.2%. Calculations show that 73% of the thiocyanate can be derived from vicianin and prunasin, with 27% derived from beta-cyanoalanine. High urinary output of thiocyanate has been associated with endocrine and neurological disorders.
AuthorsC Ressler, J G Tatake
JournalJournal of agricultural and food chemistry (J Agric Food Chem) Vol. 49 Issue 10 Pg. 5075-80 (Oct 2001) ISSN: 0021-8561 [Print] United States
PMID11600069 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • Glucosides
  • Nitriles
  • Pyrimidinones
  • Thiocyanates
  • Toxins, Biological
  • prunasin
  • 3-cyanoalanine
  • vicine
  • Alanine
Topics
  • Alanine (administration & dosage, analogs & derivatives, analysis)
  • Animals
  • Diet
  • Fabaceae (embryology)
  • Glucosides (administration & dosage, analysis)
  • Male
  • Nitriles (administration & dosage, analysis)
  • Pyrimidinones (administration & dosage, analysis)
  • Rats
  • Rats, Sprague-Dawley
  • Seeds (chemistry)
  • Thiocyanates (urine)
  • Toxins, Biological (administration & dosage, analysis)
  • Weaning

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