New N-acetyl-L-cysteine derivatives synthesized by the degradation of proanthocyanidins as high biological activity antioxidants  

作　　者：Yuxuan Wang Ruifang Bai Siqi Luo Meng Huang Yan Cui 

机构地区：[1]School of Pharmacy,Shenyang Pharmaceutical University,Shenyang 110016,China [2]Faculty of Functional Food and Wine,Shenyang Pharmaceutical University,Shenyang 110016,China

出　　处：《Journal of Polyphenols》2021年第1期14-31,共18页多酚杂志（英文）

基　　金：This work was supported by Guidance Plan of Natural Science Foundation of Liaoning in China(2019-ZD-0463).

摘　　要：A novel degradation method was investigated to synthesize highly biologically active flavan-3-ol derivatives in the presence of N-acetyl-L-cysteine(NAC)as a nucleophile under acidic conditions for polymerized proanthocyanidins degradation.The reaction conditions were optimized by the combination of single-factor test and central composite experimental design(CCD).Grape seed proanthocyanidins were reacted with NAC at a ratio of 1:3 with 0.3 M methanolic HC1,a temperature of 55°C,and a reaction time of 50 mins.Most of the degradation products were separated and prepared by one-step high-speed countercurrent chromatography(HSCCC)and preparative high-performance liquid chromatography(prep-HPLC).Three monomeric pro anthocyanidins and four new N-acetyl-L-cysteine derivatives were isolated from degradation products with total degradation yield of 55.44%and high purity over 95%.Furthermore,the neuroprotective abilities of these compounds to H2O2-treated PC-12 neuroblastoma cells were evaluated.NAC derivatives showed better antioxidant activity than their corresponding underivatized monomers and NAC,indicating that they had a better performance in protecting PC-12 cells from oxidative stress damage.

关 键 词：N-ACETYL-L-CYSTEINE PROANTHOCYANIDINS HSCCC antioxidant activity 

分 类 号：O62[理学—有机化学]