Structural Changes of 6a-Hydroxy-Pterocarpans Upon Heating Modulate Their Estrogenicity

M.G.M. van de Schans, J.P. Vincken, T.F.H. Bovee, A.D. Cervantes, M.J. Logtenberg, H. Gruppen

Research output: Contribution to journalArticleAcademicpeer-review

12 Citations (Scopus)

Abstract

The isoflavonoid composition of an ethanolic extract of fungus-treated soybean sprouts was strongly altered by a combined acid/heat treatment. UHPLC-MS analysis showed that 6a-hydroxy-pterocarpans were completely converted to their respective, more stable, 6a,11a-pterocarpenes, whereas other isoflavonoids, from the isoflavone and coumestan subclasses, were affected to a much lesser extent (loss of ~15%). Subsequently, mixtures enriched in prenylated 6a-hydroxy-pterocarpans (pools of glyceollin I/II/III and glyceollin IV/VI) or prenylated 6a,11a-pterocarpenes (pools of dehydroglyceollin I/II/III and dehydroglyceollin IV/VI) were purified, and tested for activity on both human estrogen receptors (ERa and ERß). In particular, the response toward ERa changed, from agonistic for glyceollins to antagonistic for dehydroglyceollins. Toward ERß a decrease in agonistic activity was observed. These results indicate that the introduction of a double bond with the concomitant loss of a hydroxyl group in 6a-hydroxy-pterocarpans extensively modulates their estrogenic activity.
Original languageEnglish
Pages (from-to)10475-10484
JournalJournal of Agricultural and Food Chemistry
Volume62
DOIs
Publication statusPublished - 2014

Keywords

  • ionization mass-spectrometry
  • isoflavonoid composition
  • phytoestrogens
  • flavonoids
  • aglycones
  • genistein
  • seedlings
  • daidzein
  • soy

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