Abstract

This study used alcoholic ammonium hydroxide to directly hydrolyze and extract secoisolariciresinol diglucoside (SDG) from flaxseed hull in a one pot reaction. The optimal extraction conditions, including the concentration of ammonium hydroxide, extraction time, and temperature, were examined in single factor experiments, followed by response surface methodology (RSM) with 3-level, 3-factor Box-Behnken experiments. As a result, the optimal extraction conditions were determined as follows: material-liquid ratio 1:20, percentage of reagent ammonium hydroxide (25–28% of NH3 in water) in ethanol 33.7% (pH = 12.9), extraction time 4.9 h, and extraction temperature 75.3 °C. Under these conditions, the yield of SDG, as measured by ultra-high-performance liquid chromatography-mass spectrometry, was 23.3 mg/g, consistent with the predicted content of SDG in flaxseed hull (23.0 mg/g). Further, 30.0 g of pulverized flaxseed hull was extracted under the optimal conditions, and the extract was subjected to a single run of macroporous resin chromatography to obtain 772.1 mg of a fraction with an SDG content exceeding 76.1%. Subsequent chromatography on Sephadex LH20, yielded 602.8 mg SDG of 98.0% purity, and the yield was 20.1 mg/g (2.0%) from flaxseed hulls. Thus, one-pot hydrolysis and extraction of SDG using alcoholic ammonium hydroxide is simple, and of high-yield.Graphical abstract

Highlights

  • Linum usitatissimum L. is an important oil crop

  • Single factor experiments At first, crushed (20 mesh) and non-crushed flaxseed hull were compared for the secoisolariciresinol diglucoside (SDG) yield

  • Effects of different extraction factors on the yield of SDG Crushed (20 mesh) and non-crushed flaxseed hull were compared for the SDG yield

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Summary

Introduction

Linum usitatissimum L. is an important oil crop. Its seed, commonly known as flaxseed, contains high levels of the omega-3 unsaturated fatty acid alphalinolenic acid (Shim et al 2014; Abuzaytoun, & Shahidi 2006), which has positive effects on human health (Goyal et al 2014; Lu et al 2020). Flaxseed contains significant amounts of lignans, especially secoisolariciresinol diglucoside (SDG), which is concentrated in the hull (Milder et al 2005; Imran et al 2015). SDG is converted into the mammalian lignans enterodiol and enterolactone with the involvement of intestinal bacteria (Jin, Kakiuchi, & Hattori 2007a; Jin et al 2007b). These mammalian lignans are phytoestrogens that showed inhibition on the development of hormone-related breast and prostate cancers (Begum et al 2004; Chen, & Thompson 2003)

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