Chemical Analysis and Hemolytic Activity of the Fava Bean Aglycon Divicine

David C. McMillan, Kevin L. Schey, G. Patrick Meier, David J. Jollow

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Divicine is an unstable aglycon metabolite of the fava bean pyrimidine β-glucoside vicine. Divicine has long been thought to be a mediator of an acute hemolytic crisis, known as favism, in susceptible individuals who ingest fava beans (Vicia faba). However, a recent report has questioned the chemical identity of the divicine that was used in most of the studies on divicine hemotoxicity. The present study was undertaken to examine the hemolytic potential of synthetic divicine. Divicine was synthesized and its identity and purity were confirmed by HPLC, mass spectrometry, and NMR spectroscopy. The stability and redox behavior of divicine, under physiological conditions, were examined by HPLC and cyclic voltammetry. The data indicate that divicine is readily oxidized under aerobic conditions; however, it was sufficiently stable at pH 7.4 to permit its experimental manipulation. When 51Cr-labeled rat erythrocytes were exposed in vitro to the parent glucoside, vicine (5 mM), and then readministered to rats, no decrease in erythrocyte survival was observed. In contrast, erythrocyte survival was dramatically reduced by in vitro exposure to divicine (1.5 mM). These data demonstrate that divicine is a direct-acting hemolytic agent and thus may be a mediator of the hemolytic crisis induced by fava bean ingestion.

Original languageEnglish (US)
Pages (from-to)439-444
Number of pages6
JournalChemical Research in Toxicology
Volume6
Issue number4
DOIs
StatePublished - Jan 1 1993

Fingerprint

Vicia faba
Chemical analysis
Erythrocyte Aging
Glucosides
Rats
Hemolytic Agents
Mass Spectrometry
Favism
High Pressure Liquid Chromatography
divicine
Metabolites
Nuclear magnetic resonance spectroscopy
Cyclic voltammetry
Oxidation-Reduction
Mass spectrometry
Magnetic Resonance Spectroscopy
Eating
Erythrocytes

ASJC Scopus subject areas

  • Toxicology

Cite this

Chemical Analysis and Hemolytic Activity of the Fava Bean Aglycon Divicine. / McMillan, David C.; Schey, Kevin L.; Meier, G. Patrick; Jollow, David J.

In: Chemical Research in Toxicology, Vol. 6, No. 4, 01.01.1993, p. 439-444.

Research output: Contribution to journalArticle

McMillan, David C. ; Schey, Kevin L. ; Meier, G. Patrick ; Jollow, David J. / Chemical Analysis and Hemolytic Activity of the Fava Bean Aglycon Divicine. In: Chemical Research in Toxicology. 1993 ; Vol. 6, No. 4. pp. 439-444.
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