Procyanidin B2-3′-O-Gallate Derived from Grape Seed Polymeric Procyanidins via the Galloyl-Attached Nucleophilic Degradation as a Potential Hepatoprotective Agent,Journal of Agricultural and Food Chemistry

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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
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-08-14 , DOI: 10.1021/acs.jafc.4c01704
Shuting Zhang ₁ , Fei Wang _{1,

2} , Yanxia Yu ₁ , Yuxing Jia ₁ , Baoshan Sun _{1,

3} , Fang Wang ₁

Affiliation

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.

中文翻译：

原花青素 B2-3'-O-没食子酸酯通过没食子酰基亲核降解从葡萄籽聚合原花青素中衍生，作为潜在的保肝剂

开发了一种利用没食子酰连接的亲核降解制备没食子酰化原花青素（GPC）的有效方法。在通过Box-Behnken设计和单因素实验优化的降解条件下，产生了两个二聚体和三个四聚体GPC，原花青素B2-3'- O-没食子酸酯（B2-3'-G）的产量高达232 mg /g（PPC）。 B2-3'-G 的结构通过 UV、FTIR、NMR、CD、MS 和间苯葡萄糖分解鉴定。此外，还研究了 B2-3'-G 对酒精性肝损伤 (ALI) 的保护作用。与母体化合物相比，B2-3'-G 由于其聚合度和没食子酰基而表现出更强的抑制 ALI 的能力。随后的实验表明，在乙醇之前用 B2-3'-G 预处理 BRL-3A 细胞可通过激活 Nrf2-HO-1/NQO1 途径和启动酶抗氧化系统来改善 ALI。这些发现表明GPC B2-3′-G是一种潜在的保肝剂，为GPC的功能开发提供了新的视角。

更新日期：2024-08-14

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