Sulfation of genistein alters its antioxidant properties and its effect on platelet aggregation and monocyte and endothelial function

Gerald Rimbach, Peter D Weinberg, Sonia Pascual-Teresa, Maria Garcia Alonso, Ben A Ewins, Rufus Turner, Anne Marie Minihane, Nigel Peter Botting, Brian Fairley, Seiichi Matsugo

Research output: Contribution to journalArticlepeer-review

119 Citations (Scopus)

Abstract

Soy isoflavones have been extensively studied because of their possible benefits to human health. Genistein, the major isoflavone aglycone, has received most attention; however, it undergoes extensive metabolism (e.g. conjugation with sulfuric acid) in the gut and liver, which may affect its biological proper-ties. This study investigated the antioxidant activity and free radical-scavenging properties of genistein, genistein-4'-sulfate and genistein-4'-7-disulfate as well as their effect on platelet aggregation and monocyte and endothelial function. Electron spin resonance spectroscopy (ESR) and spin trapping data and other standard antioxidant assays indicated that genistein is a relatively weak antioxidant compared to quercetin and that its sulfated metabolites are even less effective. Furthermore, genistein-4'-sulfate was less potent than genistem, and genistein-4'-7-disulfate even less potent, at inhibiting collagen-induced platelet aggregation, nitric oxide (NO) production by macrophages, and secretion by primary human endothelial cells of monocyte chemoattractant protein 1 (MCP-1), intercellular adhesion molecule 1 (ICAM-1) and vascular cell adhesion molecule 1 (VCAM-1). The current data suggest that sulfation of genistein, with the associated loss of hydroxyl groups, decreases its antioxidant activity and its effect on platelet aggregation, inflammation, cell adhesion and chemotaxis. (C) 2004 Elsevier B.V All rights reserved.

Original languageEnglish
Pages (from-to)229-237
Number of pages9
JournalBiochimica et Biophysica Acta
Volume1670
Issue number3
DOIs
Publication statusPublished - 24 Feb 2004

Keywords

  • genistein
  • isoflavone
  • sulfation
  • cell adhesion
  • platelet aggregation
  • inflammation
  • RAW 264.7 MACROPHAGES
  • TNF-ALPHA SECRETION
  • CHEMOATTRACTANT PROTEIN-1
  • GENE-EXPRESSION
  • DAIDZEIN
  • MICE
  • ATHEROSCLEROSIS
  • BIOAVAILABILITY
  • ISOFLAVONOIDS
  • CONSUMPTION

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