title: Synthesis and Biological Testing of Novel Glucosylated Epigallocatechin Gallate (EGCG) Derivatives.
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.
authors.affiliation: Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China. jeachris@sina.com.|Tea Research Center of Yunnan, Kunming 650201, China. jeachris@sina.com.|Pu-er Tea Academy, Yunnan Agricultural University, Kunming 650201, China. jeachris@sina.com.
authors.forename: Xin
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China. wangjingzb4321@163.com.|Tea Research Center of Yunnan, Kunming 650201, China. wangjingzb4321@163.com.
authors.forename: Jing
authors.initials: J
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. hujiangmiao@mail.kib.ac.cn.
authors.forename: Jiang-Miao
authors.initials: JM
authors.lastname: Hu
authors.affiliation: Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China. lichuangyewei100@163.com.|Tea Research Center of Yunnan, Kunming 650201, China. lichuangyewei100@163.com.
authors.forename: Ye-Wei
authors.initials: YW
authors.lastname: Huang
authors.affiliation: Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China. wuxiaoyun79@163.com.|Tea Research Center of Yunnan, Kunming 650201, China. wuxiaoyun79@163.com.|Pu-er Tea Academy, Yunnan Agricultural University, Kunming 650201, China. wuxiaoyun79@163.com.
authors.forename: Xiao-Yun
authors.initials: XY
authors.lastname: Wu
authors.affiliation: Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China. zichengting@126.com.|Tea Research Center of Yunnan, Kunming 650201, China. zichengting@126.com.|Pu-er Tea Academy, Yunnan Agricultural University, Kunming 650201, China. zichengting@126.com.
authors.forename: Cheng-Ting
authors.initials: CT
authors.lastname: Zi
authors.affiliation: Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China. wangxuanjun@gmail.com.|Tea Research Center of Yunnan, Kunming 650201, China. wangxuanjun@gmail.com.|Pu-er Tea Academy, Yunnan Agricultural University, Kunming 650201, China. wangxuanjun@gmail.com.|State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Kunming 650201, China. wangxuanjun@gmail.com.
authors.forename: Xuan-Jun
authors.initials: XJ
authors.lastname: Wang
authors.affiliation: Key Laboratory of Pu-er Tea Science, Ministry of Education, Yunnan Agricultural University, Kunming 650201, China. shengj@ynau.edu.cn.|Tea Research Center of Yunnan, Kunming 650201, China. shengj@ynau.edu.cn.|State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Kunming 650201, China. shengj@ynau.edu.cn.
authors.forename: Jun
authors.initials: J
authors.lastname: Sheng
mesh_terms: D000975:Antioxidants / Q000494:pharmacology; D002392:Catechin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D005947:Glucose / Q000378:metabolism*; D006801:Humans
chemical_list: D000975:Antioxidants; D002392:Catechin; C045651:epigallocatechin gallate; D005947:Glucose
keywords: DPPH; anticancer activity; epigallocatechin gallate (EGCG); glycosides; synthesis