High-yield production of secoisolariciresinol diglucoside from flaxseed hull by extraction with alcoholic ammonium hydroxide and chromatography on microporous resin

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: [Figure not available: see fulltext.]