jf9b06264_si_001.pdf (3.12 MB)
Structural Modifications of a Flaxseed Lignan in Pursuit of Higher Liposolubility: Evaluation of the Antioxidant and Permeability Properties of the Resulting Derivatives
journal contribution
posted on 2019-12-11, 13:08 authored by Ping Lan, Muxiang Du, Yinglai Teng, Martin G. Banwell, Hong Nie, Martin J. T. Reaney, Yong WangWhile lignans and their biogenetic precursors can have
various
health benefits, the poor liposolubilities of such phenolic systems
have restricted their application as antioxidants in the food industry.
The research reported here was aimed at addressing these matters through
derivatizing certain forms of such compounds and then assessing their
properties as potential nutraceuticals. In particular, crude flaxseed
lignan was purified to afford secoisolariciresinol diglucoside (SDG, 1) that was then subjected to structural modification. By
such means, the SDG long-chain fatty acid esters 4–9 and 11–13, the fully acetylated
SDG 10, secoisolariciresinol (SECO, 2),
and anhydrosecoisolariciresinol (ASECO, 14) were obtained.
The antioxidant activities of these derivatives were determined while
their permeability properties were evaluated. Such studies revealed
that certain SDG derivatives possessing useful liposolubilities also
retained their antioxidative properties, as well as being capable
of permeating Caco-2 cell monolayers while being nontoxic to them.
SDG fatty acid esters 4–9 and 11–13 could be developed into emulsifiers
with enhanced health benefits, especially considering their improved
antioxidative (ca. <11 000 μmol Trolox/g) and permeability
properties. This study thus highlights strategies for the structural
modification of SDG so as to generate derivatives with superior properties
in terms of their utility in the food and pharmaceutical industries.