School of Health, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.
National Research and Development Center of Freshwater Fish Processing, College of Life Sciences, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.
Food Res Int. 2024 Oct;193:114860. doi: 10.1016/j.foodres.2024.114860. Epub 2024 Jul 31.
Grape seed proanthocyanidin (GSP), as a natural antioxidant, has great potential to be developed into a lipid-lowering agent, but its low lipophilicity and stability greatly limit its application. In this study, an enzymatic esterification strategy was developed to introduce fatty acid chains into GSP, resulting in the successful synthesis of a series of new GSP derivatives. The results showed that up to 85% conversion of GSP and 35% TAG inhibition rate of GSP derivatives were achieved. The structures of GSP derivatives were identified by UPLC-MS/MS, and seven derivatives were confirmed as catechin-3'-O-laurate, epicatechin-3'-O-laurate, epicatechin gallate-3″,5″-di-O-laurate, epicatechin gallate-3',3″,5″-tri-O-laurate, procyanidin B1-3',3″-di-O-laurate, procyanidin B2-3',3″-di-O-laurate and procyanidin C1-3',3″,3‴-tri-O-laurate by NMR. GSP derivatives exhibited higher inhibitory effects on lipid accumulation, intracellular TAG and TC than parent GSP. These results indicate that GSP derivatives have potential as lipid-lowering agents for utilization in the food industry.
葡萄籽原花青素（GSP）作为一种天然抗氧化剂，具有很大的开发潜力，可以作为降脂剂，但它的低亲脂性和不稳定性极大地限制了它的应用。在本研究中，开发了一种酶酯化策略，将脂肪酸链引入 GSP 中，成功合成了一系列新的 GSP 衍生物。结果表明，GSP 的转化率高达 85%，GSP 衍生物对 TAG 的抑制率达到 35%。通过 UPLC-MS/MS 鉴定了 GSP 衍生物的结构，通过 NMR 确认了其中 7 种衍生物为儿茶素-3'-O-月桂酸酯、表儿茶素-3'-O-月桂酸酯、表儿茶素没食子酸酯-3″,5″-二-O-月桂酸酯、表儿茶素没食子酸酯-3',3″,5″-三-O-月桂酸酯、原花青素 B1-3',3″-二-O-月桂酸酯、原花青素 B2-3',3″-二-O-月桂酸酯和原花青素 C1-3',3″,3‴-三-O-月桂酸酯。GSP 衍生物对脂质积累、细胞内 TAG 和 TC 的抑制作用均高于母体 GSP。这些结果表明，GSP 衍生物具有作为降脂剂应用于食品工业的潜力。
