(1R)-1,4-epoxy-11α-hydroxy-3,4-seco-lup-20(30)-ene-3,28-dioic acid 3-methyl ester 28-O-β-D-glucopyranoside | 1381760-01-5

• 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: (1R)-1,4-epoxy-11α-hydroxy-3,4-seco-lup-20(30)-ene-3,28-dioic acid 3-methyl ester 28-O-β-D-glucopyranoside
• 英文别名: acanthosessilioside B；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,5R,8R,9R,10S,11R,13R,14R,15R,18S)-11-hydroxy-8-(2-methoxy-2-oxoethyl)-1,2,6,6,9-pentamethyl-15-prop-1-en-2-yl-7-oxapentacyclo[11.7.0.02,10.05,9.014,18]icosane-18-carboxylate
• CAS: 1381760-01-5
• 化学式: C₃₇H₅₈O₁₁
• 分子量: 678.861
• InChiKey: IXRYSFZKSCQFAA-BYRFBRAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1R)-1,4-epoxy-11α-hydroxy-3,4-seco-lup-20(30)-ene-3,28-dioic acid 3-methyl ester 28-O-β-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 葡萄糖
  参考文献：
  名称：

  Bioactive 3,4-seco-Triterpenoids from the Fruits of Acanthopanax sessiliflorus

  摘要：

  Eight new 3,4-seco-lupane triterpenes and glycosides, acanthosessiligenins I and II (1, 3) and acanthosessiliosides A-F (2, 4-8), as well as six known 3,4-seco-lupane triterpenes (9-14) were isolated from an ethanolic extract of Acanthopanax sessiliflorus fruits. The chemical structures of 1-8 were determined by spectroscopic data interpretation. All isolated compounds were tested for their cytotoxicity against six human cancer cell lines and their ability to inhibit LPS-induced nitric oxide production in RAW 264.7 macrophages.

  DOI：

  10.1021/np3002173

文献信息

• Bioactive 3,4-<i>seco</i>-Triterpenoids from the Fruits of <i>Acanthopanax sessiliflorus</i>
  作者：Dae-Young Lee、Kyeong-Hwa Seo、Dong-Sung Lee、Youn-Chul Kim、In-Sik Chung、Gye-Won Kim、Dae-Sung Cheoi、Nam-In Baek

  DOI：10.1021/np3002173

  日期：2012.6.22

  Eight new 3,4-seco-lupane triterpenes and glycosides, acanthosessiligenins I and II (1, 3) and acanthosessiliosides A-F (2, 4-8), as well as six known 3,4-seco-lupane triterpenes (9-14) were isolated from an ethanolic extract of Acanthopanax sessiliflorus fruits. The chemical structures of 1-8 were determined by spectroscopic data interpretation. All isolated compounds were tested for their cytotoxicity against six human cancer cell lines and their ability to inhibit LPS-induced nitric oxide production in RAW 264.7 macrophages.