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Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants.
J Agric Food Chem. 2011 Jun 22; 59(12):6526-33.JA

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhong Y
Department of Biochemistry, Memorial University of Newfoundland , St. John's, Newfoundland, Canada A1B 3X9.
Shahidi F
No affiliation info available

MeSH

AntioxidantsCamellia sinensisCatechinFatty AcidsHydrophobic and Hydrophilic InteractionsMolecular StructurePlant ExtractsSolubility

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21526762

Citation

Zhong, Ying, and Fereidoon Shahidi. "Lipophilized Epigallocatechin Gallate (EGCG) Derivatives as Novel Antioxidants." Journal of Agricultural and Food Chemistry, vol. 59, no. 12, 2011, pp. 6526-33.
Zhong Y, Shahidi F. Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants. J Agric Food Chem. 2011;59(12):6526-33.
Zhong, Y., & Shahidi, F. (2011). Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants. Journal of Agricultural and Food Chemistry, 59(12), 6526-33. https://doi.org/10.1021/jf201050j
Zhong Y, Shahidi F. Lipophilized Epigallocatechin Gallate (EGCG) Derivatives as Novel Antioxidants. J Agric Food Chem. 2011 Jun 22;59(12):6526-33. PubMed PMID: 21526762.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants. AU - Zhong,Ying, AU - Shahidi,Fereidoon, Y1 - 2011/05/31/ PY - 2011/4/30/entrez PY - 2011/4/30/pubmed PY - 2011/10/13/medline SP - 6526 EP - 33 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 59 IS - 12 N2 - 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. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/21526762/Lipophilized_epigallocatechin_gallate__EGCG__derivatives_as_novel_antioxidants_ L2 - https://doi.org/10.1021/jf201050j DB - PRIME DP - Unbound Medicine ER -