Abstract
A series of thiol-nucleophiles, captopril, l-cysteine, and tiopronin, were introduced to the degradation reaction of grape seed extracts and the eight new bioactive flavan-3-ol derivatives were observed. Then, these derivatives were successfully separated and prepared in large quantity by high-speed counter-current chromatography (HSCCC) and semi-preparative HPLC under the optimized separation conditions. The appropriate two solvent systems consisted of n-hexane–ethyl acetate–methanol–water (0.05:1.5:0.5:1.2, v/v/v/v) and n-hexane–ethyl acetate–water (1:10:10, v/v/v) with head–tail mode were used for HSCCC two-step separation of captopril degradation products. N-butanol–ethyl acetate–methanol–water (2:4:0.5:6, v/v/v/v) with a combination of tail–head and head–tail elution modes in HSCCC run of l-cysteine degradation products, and n-hexane–ethyl acetate–methanol–water (0.15:1.6:0.4:1, v/v/v/v) was applied with head–tail and tail–head elution modes in HSCCC separation of tiopronin degradation products. The structures of these derivatives were confirmed by MS and 1H NMR analysis. Moreover, a systematic comparison of antioxidant activity of all the eleven degradation products was first implemented and found that most of the derivatives had stronger antioxidant activity than free catechins.
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Acknowledgements
This work was supported by Liao Ning Revitalization Talents Program (XLYC1902040), the Excellent Youth Talent Support Program of Shenyang Pharmaceutical University (ZQN201817) and the program of The Educational Department of Liaoning Province (2019LQNO8).
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Tian, R., Suo, H., Zhang, S. et al. Separation of a family of antioxidants flavan-3-ol thio-conjugates from procyanidins by high-speed counter-current chromatography. Eur Food Res Technol 246, 1017–1029 (2020). https://doi.org/10.1007/s00217-020-03465-4
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DOI: https://doi.org/10.1007/s00217-020-03465-4