Compositional changes in (iso)flavonoids and estrogenic activity of three edible Lupinus species by germination and Rhizopus-elicitation. (February 2016)

• Record Type: Journal Article
• Authors: Aisyah, Siti; Vincken, Jean-Paul; Andini, Silvia; Mardiah, Zahara; Gruppen, Harry
• Is Part Of: Phytochemistry. Volume 122(2016:Feb.)
• Page Start: 65
• Page End: 75
• Publication Date: 2016-02
• Subjects: Lupinus luteus -- Lupinus albus -- Lupinus angustifolius -- Fabaceae -- Genistein -- 2′-Hydroxygenistein -- Mass spectrometry -- Prenylation -- Deglycosylation; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2015.12.015
• Languages: English
• ISSNs: 0031-9422

Abstract

Graphical abstract: The (iso)flavonoid content and composition of lupine species changed during germination and Rhizopus -elicitation. The changes increased the agonistic activity towards the human estrogen receptors. Highlights: The isoflavonoid content of lupine seeds increased during germination. Three lupine species responded differently towards Rhizopus elicitation. Rhizopus elicitation particularly increased the content of 2′-OH genistein derivatives. The position of prenylation of isoflavonoids was species-dependent. Simultaneous germination and elicitation altered the estrogenic potential of lupine. Abstract: The effects of germination and elicitation on (iso)flavonoid composition of extracts from three edible lupine species ( Lupinus luteus, Lupinus albus, Lupinus angustifolius ) were determined by RP-UHPLC–MS n . The total (iso)flavonoid content of lupine increased over 10-fold upon germination, with the total content and composition of isoflavonoids more affected than those of flavonoids. Glycosylated isoflavones were the most predominant compounds found in lupine seedlings. Lesser amounts of isoflavone aglycones, including prenylated ones, were also accumulated. Elicitation with Rhizopus oryzae, in addition to germination, raised the content of isoflavonoids further: the total content of 2′-hydroxygenistein derivatives was increased considerably, without increasing that of genistein derivatives. Elicitation by fungus triggered prenylation of isoflavonoids, especially of the 2′-hydroxygenistein derivatives. The preferred positions of prenylation differed among the three lupine species. The change in isoflavone composition increased the agonistic activity of the extracts towards the human estrogen receptors, whereas no antagonistic activity was observed.