Hydroxycinnamic acids are ester-linked directly to glucosyl moieties within the lignan macromolecule from flaxseed hulls

Phytochemistry
Karin StruijsHarry Gruppen

Abstract

In flaxseed hulls, lignans are present in an oligomeric structure. Secoisolariciresinol diglucoside (SDG), ester-linked to hydroxy-methyl-glutaric acid (HMGA), forms the backbone of this lignan macromolecule. The hydroxycinnamic acids p-coumaric acid glucoside (CouAG) and ferulic acid glucoside (FeAG) are also part of the lignan macromolecule. However, their position and type of linkage are still unknown. The aim of this study was to investigate how CouAG and FeAG are linked within the lignan macromolecule from flaxseed hulls. Fragments of the lignan macromolecule were obtained by partial saponification. After isolation of the fragments by preparative RP-HPLC, several key structures were identified by MS and NMR. Within the lignan macromolecule, CouAG is attached to the C-6 position of a glucosyl moiety of SDG. FeA is linked to the C-2 position of a glucosyl moiety of SDG. FeAG is ester-linked within the lignan macromolecule with its carboxyl group, but it remains unclear whether FeAG links to the C-2 or C-6 position of SDG. Attachment of HMGA to the glucosyl moiety of CouAG or FeAG was not observed. The results clearly show that within the lignan macromolecule, the hydroxycinnamic acids are linked directly via an ester bond to...Continue Reading

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Citations

Jul 19, 2011·Plant Foods for Human Nutrition·Agnieszka KosińskaRyszard Amarowicz
Oct 5, 2010·Nutrition Reviews·Julia PetersonMarjorie L McCullough
Dec 26, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Adriana Slavova-KazakovaRyszard Amarowicz
May 28, 2014·Fitoterapia·Li SongJian-Gong Shi
May 21, 2013·Phytochemistry·Evangelos C TatsisBernd Schneider
Aug 27, 2015·Fitoterapia·Qing-Yun YangChun-Suo Yao
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Aug 11, 2016·Food Chemistry·Zheng-Qun ZhouHao Gao
Jan 30, 2018·Journal of Asian Natural Products Research·Xiao-Xiao HuangShao-Jiang Song
Jan 17, 2020·The Plant Journal : for Cell and Molecular Biology·Benjamin ThiombianoRebecca Dauwe
Feb 23, 2021·Frontiers in Microbiology·Sandra M KellyDouwe van Sinderen
Oct 18, 2008·Journal of Agricultural and Food Chemistry·Jian-Ping YuanXin Liu
May 28, 2021·Journal of Natural Products·Xiaolei YangMartin J T Reaney
Jan 10, 2017·Journal of Agricultural and Food Chemistry·Fernanda Guimarães Drummond E SilvaFlavia Maria Netto

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