Lipophilized Epigallocatechin Gal late (EGCG) Derivatives as Novel Antioxidants
Lipophilized Epigallocatechin Gal late (EGCG) Derivatives as Novel Antioxidants
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DOI：
10.1021/jf201050j
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发表时间：
2011-06-22
影响因子：
6.1
通讯作者：
Shahidi, Fereidoon
中科院分区：
文献类型：
--
作者：
Zhong, Ying;Shahidi, Fereidoon
表没食子儿茶素没食子酸酯（EGCG）是绿色茶中的主要多酚，并且已知提供与茶消费相关的许多健康益处。对表没食子儿茶素没食子酸酯进行结构修饰，以改善其亲脂性，扩大其在亲脂性介质中的应用，并增强其在体内的细胞吸收。水溶性的EGCG与选定的长链饱和和不饱和脂肪酸的酯化进行，然后通过纯化过程。制备了硬脂酸（SA）、二十碳五烯酸（EPA）和二十二碳六烯酸（DHA）与表没食子儿茶素没食子酸酯（EGCG）的酯衍生物，并通过辛醇-水分配系数证实了它们的亲脂性增强。通过HPLC-MS和H-1和C-13 NMR确定的EGCG衍生物的化学结构是SA、EPA和DHA的EGCG-3 '，5'，3“，5”-O-四酯（分别为化合物1、2和3）。表没食子儿茶素没食子酸酯衍生物在清除1，1-二苯基-2-苦基肼基（DPPH）自由基方面表现出比表没食子酸酯本身更强的抗氧化活性。结果表明，表没食子儿茶素没食子酸酯衍生物可作为潜在的亲脂性抗氧化剂在食品，化妆品和医药行业。
Epigallocatechin gallate (EGCG) is the major polyphenol in green tea and known to render many health benefits associated with tea consumption. EGCG was modified structurally to improve its lipophilicity, expand its application in lipophilic media, and enhance its cellular absorption in vivo. Esterification of the water-soluble EGCG with selected long-chain saturated and unsaturated fatty acids was carried out, followed by a purification process. Ester derivatives of EGCG with stearic acid (SA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA) were prepared, and their enhanced lipophilicity was confirmed by octanol water partition coefficient. The chemical structures of the EGCG derivatives, determined by HPLC-MS and H-1 and C-13 NMR, were EGCG-3',5',3 '',5 ''-O-tetraesters of SA, EPA, and DHA (compounds 1, 2, and 3, respectively). The lipophilized EGCG derivatives exhibited greater antioxidant activity in scavenging the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical than EGCG itself. The results suggest that EGCG derivatives may be used as potential lipophilic antioxidants in the food, cosmetic, and medicinal industries.