Related Experiment Video
Updated: Jul 8, 2026

Visualizing Lignification Dynamics in Plants with Click Chemistry: Dual Labeling is BLISS!
Published on: January 26, 2018
Hydroxycinnamic acids are ester-linked directly to glucosyl moieties within the lignan macromolecule from flaxseed
Karin Struijs1, Jean-Paul Vincken, René Verhoef
1Laboratory of Food Chemistry, Wageningen University, PO Box 8129, 6700 EV Wageningen, The Netherlands.
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 the glucosyl moiety of SDG.
More Related Videos
Related Concept Videos
Chemistry of Carbohydrates
Cellulose and Pectic Polysaccharides
As a cell matures, its cell wall specializes according to its type. For example, the parenchyma cells of...
Glycosaminoglycans
GAGS are found in the extracellular matrix of vertebrates, invertebrates, and bacteria. Due to their polar nature they attract water, and serve as excellent lubricants or shock absorbers in an animal body.
Hyaluronic...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Lipids as Anchors
The carboxy-terminal of most of the prenylated proteins, such as Ras proteins, contains the...

