title: Compositional changes in (iso)flavonoids and estrogenic activity of three edible Lupinus species by germination and Rhizopus-elicitation.
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.
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands; Department of Chemistry Education, Indonesia University of Education, Setiabudi 229, Bandung 40154, Indonesia.
authors.forename: Siti
authors.initials: S
authors.lastname: Aisyah
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands.
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Vincken
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands; Department of Chemistry, Satya Wacana Christian University, Diponegoro 52-60, Salatiga 50211, Indonesia.
authors.forename: Silvia
authors.initials: S
authors.lastname: Andini
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands; Indonesian Agency for Agricultural Research and Development, Indonesian Ministry of Agriculture, Ragunan 29, Jakarta Selatan 12540, Indonesia.
authors.forename: Zahara
authors.initials: Z
authors.lastname: Mardiah
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands. Electronic address: harry.gruppen@wur.nl.
authors.forename: Harry
authors.initials: H
authors.lastname: Gruppen
mesh_terms: D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D005658:Fungi; D019833:Genistein / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018525:Germination; D006031:Glycosylation; D007529:Isoflavones / Q000032:analysis / Q000378:metabolism / Q000494:pharmacology*; D031297:Lupinus / Q000737:chemistry* / Q000235:genetics; D048789:Phytoestrogens / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D054876:Prenylation; D012233:Rhizopus / Q000187:drug effects / Q000254:growth & development*; D036226:Seedlings / Q000737:chemistry
chemical_list: D005419:Flavonoids; D007529:Isoflavones; D048789:Phytoestrogens; D019833:Genistein
keywords: 2′-Hydroxygenistein; Deglycosylation; Fabaceae; Genistein; Lupinus albus; Lupinus angustifolius; Lupinus luteus; Mass spectrometry; Prenylation