The flavonoid herbacetin diglucoside as a constituent of the lignan macromolecule from flaxseed hulls.
Lignans in flaxseed are known to be part of a macromolecule in which they are connected through the linker-molecule hydroxy-methyl-glutaric acid (HMGA). In this study, the lignan macromolecule was extracted from flaxseed hulls and degraded to its monomeric constituents by complete saponification. Besides secoisolariciresinol diglucoside (SDG), the phenolic compounds p-coumaric acid glucoside (CouAG) and ferulic acid glucoside (FeAG) were isolated, which was expected based on indications from the literature. Also the flavonoid herbacetin diglucoside (HDG) was found. The presence of HDG was confirmed by NMR following preparative RP-HPLC purification. Also the presence of the three other constituents (CouAG, FeAG and SDG) was confirmed by NMR. To prove that HDG is a substructure of the lignan macromolecule, the macromolecule was fragmented by partial saponification. A fragment consisting of HDG and HMGA was indicated. This fragment was isolated by preparative RP-HPLC and its identity was confirmed by NMR. It is concluded that the flavonoid HDG is a substructure of the lignan macromolecule from flaxseed hulls and that it is incorporated in the macromolecule via the same linker-molecule as SDG.
Struijs
Karin
K
Laboratory of Food Chemistry, Wageningen University, P.O. Box 8129, 6700 EV Wageningen, The Netherlands.
Vincken
Jean-Paul
JP
Verhoef
René
R
van Oostveen-van Casteren
Willemiek H M
WH
Voragen
Alphons G J
AG
Gruppen
Harry
H
D005591:Chemical Fractionation; D003373:Coumaric Acids / Q000737:chemistry / Q000302:isolation & purification; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification; D019597:Flax / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification; D019906:Nuclear Magnetic Resonance, Biomolecular; D011422:Propionates
D003373:Coumaric Acids; D005419:Flavonoids; D005960:Glucosides; D017705:Lignans; D011422:Propionates; C521875:herbacetin diglucoside; C495469:p-coumaric acid