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Procyanidin B2-3′-O-Gallate Derived from Grape Seed Polymeric Procyanidins via the Galloyl-Attached Nucleophilic Degradation as a Potential Hepatoprotective Agent

文献类型： 外文期刊

作者： Zhang, Shuting 1 ; Wang, Fei 1 ; Yu, Yanxia 1 ; Jia, Yuxing 1 ; Sun, Baoshan 1 ; Wang, Fang 1 ;

作者机构： 1.Shenyang Pharmaceut Univ, Sch Funct Food & Wine, Shenyang 110016, Peoples R China

2.Heilongjiang Acad Agr Sci, Food Proc Res Inst, Harbin 150086, Peoples R China

3.Inst Natl Invest Agr & Vet, Polo Dois Portos, P-2565191 Dois Portos, Portugal

关键词： galloylated procyanidins; galloyl-attached nucleophilicdegradation; procyanidin B2-3 '-O-gallate; Nrf2-HO-1/NQO1 pathway; hepatoprotective agent

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.7； 五年影响因子：6.0 ）

ISSN： 0021-8561

年卷期： 2024 年 72 卷 34 期

页码：

收录情况： SCI

摘要： An effective method was developed for preparing galloylated procyanidins (GPCs) using galloyl-attached nucleophilic degradation. Under degradation conditions optimized through Box-Behnken design and single-factor experiments, two dimeric and three tetrameric GPCs were produced, with the yield of procyanidin B2-3 '-O-gallate (B2-3 '-G) reaching up to 232 mg/g (PPCs). The structure of B2-3 '-G was identified by UV, FTIR, NMR, CD, MS, and phloroglucinolysis. Furthermore, the protective effect of B2-3 '-G against alcohol-induced liver injury (ALI) was investigated. Compared with the parent compounds, B2-3 '-G exhibited a stronger capacity for inhibiting ALI, attributed to its polymerization degree and galloyl group. Subsequent experiments revealed that the pretreatment of BRL-3A cells with B2-3 '-G prior to ethanol improved ALI through activation of the Nrf2-HO-1/NQO1 pathway and initiation of enzymatic antioxidant systems. These findings suggest that GPC B2-3 '-G is a potential hepatoprotective agent, which provides a new perspective for functional development of GPCs.

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