Novel l -Cysteine Incomplete Degradation Method for Preparation of Procyanidin B2-3′-O-Gallate and Exploration of its in Vitro Anti-inflammatory Activity and in Vivo Tissue Distribution

作者：Yanxia Yu, Chunying Zuo, Mingrui Li, Yuan‐Yuan Tang, Lingxi Li, Fang Wang, Shuting Zhang, Baoshan Sun · 发表于：Journal of Agricultural and Food Chemistry · 年份：2024 · DOI：10.1021/acs.jafc.3c05616 · 被引用次数：9 · 研究领域：Curcumin's Biomedical Applications、Enzyme Production and Characterization、Tannin, Tannase and Anticancer Activities

In this study, an effective method for preparation of bioactive galloylated procyanidin B2-3′- O -gallate (B2-3′-G) was first developed by incomplete depolymerization of grape seed polymeric procyanidins (PPCs) using l -cysteine (Cys) in the presence of citric acid. The structure–activity relationship of B2-3′-G was further evaluated in vitro through establishing lipopolysaccharide (LPS)-induced inflammation in RAW264.7 cells. The results suggested that the better protective effects of B2-3′-G against inflammation were attributed to its polymerization degree and the introduction of the galloyl group, compared to its four corresponding structural units. In vivo experiments demonstrated that the B2-3′-G prototype was distributed in plasma, small intestine, liver, lung, and brain. Remarkably, B2-3′-G was able to penetrate the blood–brain barrier and appeared to play an important role in improving brain health. Furthermore, a total of 18 metabolites were identified in tissues. Potential metabolic pathways, including reduction, methylation, hydration, desaturation, glucuronide conjugation, and sulfation, were suggested.