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

  • J Agric Food Chem. 2024 Aug 28;72(34):18918-18929. 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
Affiliations
  • 1. School of Functional Food and Wine, Shenyang Pharmaceutical University, Shenyang 110016, China.
  • 2. Food Processing Research Institute, Heilongjiang Academy of Agricultural Sciences, Harbin 150086, China.
  • 3. Pólo Dois Portos, Instituto National de Investigação Agrária e Veterinária, I.P., Quinta da Almoinha, Dois Portos 2565-191, Portugal.
PMID: 39140375 DOI: 10.1021/acs.jafc.4c01704
Abstract

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.

Keywords
Nrf2-HO-1/NQO1 pathway, hepatoprotective agent; galloyl-attached nucleophilic degradation; galloylated procyanidins; procyanidin B2-3′-O-gallate.
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