title: Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants.
abstract: 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 ¹H and ¹³C NMR, were EGCG-3',5',3'',5''-O-tetraesters of SA, EPA, and DHA. 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.
authors.affiliation: Department of Biochemistry, Memorial University of Newfoundland , St. John's, Newfoundland, Canada A1B 3X9.
authors.forename: Ying
authors.initials: Y
authors.lastname: Zhong
authors.forename: Fereidoon
authors.initials: F
authors.lastname: Shahidi
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D028241:Camellia sinensis / Q000737:chemistry*; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D012995:Solubility
chemical_list: D000975:Antioxidants; D005227:Fatty Acids; D010936:Plant Extracts; D002392:Catechin; C045651:epigallocatechin gallate