20-epi-urs-12,18-dien-28-oic acid 2'-O-acetyl-3β-O-α-L-arabinopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 20-epi-urs-12,18-dien-28-oic acid 2'-O-acetyl-3β-O-α-L-arabinopyranoside
• 英文别名: 20-epi-urs-12,18-dien-28-oic acid 3β-O-(2'-O-acetyl)-α-L-arabinopyranoside
• 化学式: C₃₇H₅₆O₈
• 分子量: 628.847
• InChiKey: QCRAMXSUFLHJEC-YWOACYLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  45.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  122.52
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  20-epi-urs-12,18-dien-28-oic acid 2'-O-acetyl-3β-O-α-L-arabinopyranoside 在 水 作用下， 生成 L-(+)-arabinose
  参考文献：
  名称：

  Seven new triterpenoids from the aerial parts of Ilex cornuta and protective effects against H2O2-induced myocardial cell injury

  摘要：

  Seven new triterpenoids (1-7), together with two known ones (8-9), were isolated from the aerial parts of Ilex cornuta. The leaves of I. cornuta are the major source of "Kudingcha", a popular herbal tea consumed in China and other countries. The structures of compounds 1-7 were determined as 20-epi-urs-12,18-dien-28-oic acid 3 beta-O-alpha-L-arabinopyranoside (1), 20-epi-urs-12,18-dien-28-oic acid 2'-O-acetyl-3 beta-O-alpha-L-arabinopyranoside (2), 20-epi-urs-12,18-dien-28-oic acid 3 beta-O-beta-D-glucuronopyranoside-6-O-methyl ester (3), 3 beta, 23-dihydroxy-20-epi-urs-12,18-dien-28-oic acid (4), 23-hydroxy-20-epi-urs12,18-dien-28-oic acid 3 beta-O-alpha-L-arabinopyranoside (5), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3 beta-O-beta-D-glucuronic acid (6), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3 beta-O-beta-D-glucuronopyranoside-6-O-methyl ester (7), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and chemical reactions. Protective effects against H2O2-induced H9c2 cardiomyocyte injury were tested in vitro for compounds 1-9, and the data showed that compound 4 had significant cell-protective effect. Compounds 1-9 did not show significant DPPH radical scavenging activity. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2015.10.010

文献信息

• Seven new triterpenoids from the aerial parts of Ilex cornuta and protective effects against H2O2-induced myocardial cell injury
  作者：Shanshan Li、Jianping Zhao、Wenlian Wang、Yuchen Lu、Qiongming Xu、Yanli Liu、Xiaoran Li、Ikhlas A. Khan、Shilin Yang

  DOI：10.1016/j.phytol.2015.10.010

  日期：2015.12

  Seven new triterpenoids (1-7), together with two known ones (8-9), were isolated from the aerial parts of Ilex cornuta. The leaves of I. cornuta are the major source of "Kudingcha", a popular herbal tea consumed in China and other countries. The structures of compounds 1-7 were determined as 20-epi-urs-12,18-dien-28-oic acid 3 beta-O-alpha-L-arabinopyranoside (1), 20-epi-urs-12,18-dien-28-oic acid 2'-O-acetyl-3 beta-O-alpha-L-arabinopyranoside (2), 20-epi-urs-12,18-dien-28-oic acid 3 beta-O-beta-D-glucuronopyranoside-6-O-methyl ester (3), 3 beta, 23-dihydroxy-20-epi-urs-12,18-dien-28-oic acid (4), 23-hydroxy-20-epi-urs12,18-dien-28-oic acid 3 beta-O-alpha-L-arabinopyranoside (5), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3 beta-O-beta-D-glucuronic acid (6), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3 beta-O-beta-D-glucuronopyranoside-6-O-methyl ester (7), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and chemical reactions. Protective effects against H2O2-induced H9c2 cardiomyocyte injury were tested in vitro for compounds 1-9, and the data showed that compound 4 had significant cell-protective effect. Compounds 1-9 did not show significant DPPH radical scavenging activity. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.