epigallocatechin gallate 7,4'-bis-O-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: epigallocatechin gallate 7,4'-bis-O-α-D-glucopyranoside
• 英文别名: [(2R,3R)-2-[3,5-dihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5-hydroxy-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₃₄H₃₈O₂₁
• 分子量: 782.663
• InChiKey: MVFJPVYFZQOLSA-YUZCJUIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  356
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 、 蔗糖 在 Leuconostoc mesenteroides B-1299CB glucansucrase 作用下， 以 水 为溶剂， 反应 6.5h， 以19.9%的产率得到epigallocatechin gallate 7,4'-bis-O-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis, Structure Analyses, and Characterization of Novel Epigallocatechin Gallate (EGCG) Glycosides Using the Glucansucrase from Leuconostoc mesenteroides B-1299CB

  摘要：

  In this study, three epigallocatechin gallate glycosides were synthesized by the acceptor reaction of a glucansucrase produced by Leuconostoc mesenteroides B-1299CB with epigallocatechin gallate (EGCG) and sucrose. Each of these glycosides was then purified, and the structures were assigned as follows: epigallocatechin gallate 7-O-alpha-D-glucopyranoside (EGCG-G1); epigallocatechin gallate 4'-O-alpha-D-glucopyranoside (EGCG-G1'); and epigallocatechin gallate 7,4'-O-a-D-glucopyranoside (EGCG-G2). One of these compounds (EGCG-G1) was a novel compound. The EGCG glycosides exhibited similar or slower antioxidant effects, depending on their structures (EGCG >= EGCG-G1 > EGCG-G1' > EGCG-G2), and also manifested a higher degree of browning resistance than was previously noted in EGCG. Also, EGCG-G1, EGCG-G1', and EGCG-G2 were 49, 55, and 114 times as water soluble, respectively, as EGCG.

  DOI：

  10.1021/jf052359i

文献信息

• 신규한 EGCG 배당체 및 이의 제조방법
  申请人：Seoul National University R&DB Foundation 서울대학교산학협력단(120070509242) Corp. No ▼ 114371-0009224BRN ▼119-82-03684

  公开号：KR20180023595A

  公开（公告）日：2018-03-07

  본 발명은 신규한 EGCG 배당체 및 이의 제조방법에 관한 것이다. 보다 구체적으로, 본 발명은 수용해성 및 갈변억제 특성이 향상된 신규한 EGCG 배당체, 상기 EGCG 배당체의 제조 방법 및 상기 EGCG 배당체의 화장료 조성물, 약제학적 조성물 및 식품 조성물에서의 용도에 관한 것이다.

  本发明涉及一种新的EGCG衍生物及其制备方法。更具体地说，本发明涉及一种具有良好的溶解性和抗氧化特性的新型EGCG衍生物，以及该EGCG衍生物的制备方法、化妆品配方、药物配方和食品配方中的应用。
• Synthesis, Structure Analyses, and Characterization of Novel Epigallocatechin Gallate (EGCG) Glycosides Using the Glucansucrase from <i>Leuconostoc mesenteroides</i> B-1299CB
  作者：Young-Hwan Moon、Jin-Ha Lee、Joon-Seob Ahn、Seung-Hee Nam、Deok-Kun Oh、Don-Hee Park、Hyun-Ju Chung、Seongsoo Kang、Donal F. Day、Doman Kim

  DOI：10.1021/jf052359i

  日期：2006.2.1

  In this study, three epigallocatechin gallate glycosides were synthesized by the acceptor reaction of a glucansucrase produced by Leuconostoc mesenteroides B-1299CB with epigallocatechin gallate (EGCG) and sucrose. Each of these glycosides was then purified, and the structures were assigned as follows: epigallocatechin gallate 7-O-alpha-D-glucopyranoside (EGCG-G1); epigallocatechin gallate 4'-O-alpha-D-glucopyranoside (EGCG-G1'); and epigallocatechin gallate 7,4'-O-a-D-glucopyranoside (EGCG-G2). One of these compounds (EGCG-G1) was a novel compound. The EGCG glycosides exhibited similar or slower antioxidant effects, depending on their structures (EGCG >= EGCG-G1 > EGCG-G1' > EGCG-G2), and also manifested a higher degree of browning resistance than was previously noted in EGCG. Also, EGCG-G1, EGCG-G1', and EGCG-G2 were 49, 55, and 114 times as water soluble, respectively, as EGCG.