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Molecules 2016, 21(5), 620; doi:10.3390/molecules21050620

Synthesis and Biological Testing of Novel Glucosylated Epigallocatechin Gallate (EGCG) Derivatives

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1
Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China
2
Tea Research Center of Yunnan, Kunming 650201, China
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Pu-er Tea Academy, Yunnan Agricultural University, Kunming 650201, China
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State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
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State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Kunming 650201, China
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Authors to whom correspondence should be addressed.
Academic Editors: Jean Jacques Vanden Eynde, Annie Mayence and Tien L. Huang
Received: 10 March 2016 / Revised: 2 May 2016 / Accepted: 4 May 2016 / Published: 11 May 2016
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Abstract

Epigallocatechin gallate (EGCG) is the most abundant component of green tea catechins and has strong physiological activities. In this study, two novel EGCG glycosides (EGCG-G1 and EGCG-G2) were chemoselectively synthesized by a chemical modification strategy. Each of these EGCG glycosides underwent structure identification, and the structures were assigned as follows: epigallocatechin gallate-4′′-O-β-d-glucopyranoside (EGCG-G1, 2) and epigallocatechin gallate-4′,4′′-O-β-d-gluco-pyranoside (EGCG-G2, 3). The EGCG glycosides were evaluated for their anticancer activity in vitro against two human breast cell lines (MCF-7 and MDA-MB-231) using MTT assays. The inhibition rate of EGCG glycosides (EGCG-G1 and EGCG-G2) is not obvious. The EGCG glycosides are more stable than EGCG in aqueous solutions, but exhibited decreasing antioxidant activity in the DPPH radical-scavenging assay (EGCG > EGCG-G2 > EGCG-G1). Additionally, the EGCG glycosides exhibited increased water solubility: EGCG-G2 and EGCG-G1 were 15 and 31 times as soluble EGCG, respectively. The EGCG glycosides appear to be useful, and further studies regarding their biological activity are in progress. View Full-Text
Keywords: epigallocatechin gallate (EGCG); glycosides; anticancer activity; DPPH; synthesis epigallocatechin gallate (EGCG); glycosides; anticancer activity; DPPH; synthesis
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Zhang, X.; Wang, J.; Hu, J.-M.; Huang, Y.-W.; Wu, X.-Y.; Zi, C.-T.; Wang, X.-J.; Sheng, J. Synthesis and Biological Testing of Novel Glucosylated Epigallocatechin Gallate (EGCG) Derivatives. Molecules 2016, 21, 620.

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