Structural changes of 6a-hydroxy-pterocarpans upon heating modulate their estrogenicity.

Autor: van de Schans MG; Laboratory of Food Chemistry, Wageningen University , P.O. Box 17, 6700 AA, Wageningen, The Netherlands., Vincken JP, Bovee TF, Cervantes AD, Logtenberg MJ, Gruppen H
Jazyk: angličtina
Zdroj: Journal of agricultural and food chemistry [J Agric Food Chem] 2014 Oct 29; Vol. 62 (43), pp. 10475-84. Date of Electronic Publication: 2014 Oct 17.
DOI: 10.1021/jf503127c
Abstrakt: 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 (ERα and ERβ). In particular, the response toward ERα changed, from agonistic for glyceollins to antagonistic for dehydroglyceollins. Toward ERβ 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.
Databáze: MEDLINE