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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

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The flavan-3-ols of 10 primarily plant food byproducts, including Muscat Hamburg grape seed, hawthorn sarcocarp, litchi pericarp, cocoa bean, peanut skin, lotus seedpod, Xinyang Maojian green tea, Cinnamomi cortex, Sargentodoxa cuneata stem, and Cyperus esculentus, leaves were analyzed. Ultrahigh-performance liquid chromatography-triple quadrupole mass spectrometry was used for the analysis. Cyperus esculentus leaves contained a high amount of procyanidin B1 (198.9 mg/100 g), second only to Muscat Hamburg grape seed (292.9 mg/100 g). Unlike grape seed that contained several procyanidin B isomers with very similar retention times, C. esculentus leaves contained primarily procyanidin B1 with few isomers. Procyanidin B1 was enriched in the ethyl acetate fraction of a 70% methanol extract of C. esculentus leaves and purified at 95% purity by two runs of open column chromatography. Direct chromatography of the plant extract on octadecylsilane and Sephadex LH20 open columns improved the yield of the resultant leaf procyanidin B1 (95% purity) to 0.21‰. The present research demonstrated that the leaves of C. esculentus, byproducts of tigernut, are ideal plant sources for isolating and providing high-purity procyanidin B1.