3β,21β,22β,24-tetrahydroxyolean-12-en-3-O-α-L-rhamnopyranosyl-(1-3)-[α-L-rhamnopyranosyl-(1-2)]-β-D-galactopyranosyl-(1-2)-β-D-glucuronopyranoside

• 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: 3β,21β,22β,24-tetrahydroxyolean-12-en-3-O-α-L-rhamnopyranosyl-(1-3)-[α-L-rhamnopyranosyl-(1-2)]-β-D-galactopyranosyl-(1-2)-β-D-glucuronopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9S,10R,12aS,14aR,14bR)-9,10-dihydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxyoxane-2-carboxylic acid
• 化学式: C₅₄H₈₈O₂₃
• 分子量: 1105.28
• InChiKey: AERRIZLTJYUDAL-YOMPYYFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  77
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  374
• 氢给体数：
  14
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  3β,21β,22β,24-tetrahydroxyolean-12-en-3-O-α-L-rhamnopyranosyl-(1-3)-[α-L-rhamnopyranosyl-(1-2)]-β-D-galactopyranosyl-(1-2)-β-D-glucuronopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 D-吡喃葡萄糖醛酸 、 L-鼠李糖 、 口服葡萄糖
  参考文献：
  名称：

  Triterpene glycosides of Lupinus angustifolius

  摘要：

  Investigation of whole seeds of Lupinus angustifolius L. (Leguminosae) yielded the two triterpenoid saponins with branched monosaccharide chain 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (3) and 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside (4) along with the known compounds soyasaponin 1 (1) and 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside (2). The structures of the compounds were elucidated using hydrolysis, FAB-MS and extensive NMR experiments. Compounds 2-4 showed moderate antifungal activity against Candida albicans with MIC values of 25, 25 and 30 mug/ml, respectively. Only soyasaponin I was found weakly hemolytic (HC50 > 500 mug/ml). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(02)00112-7

文献信息

• Triterpene glycosides of Lupinus angustifolius
  作者：Girma M. Woldemichael、Michael Wink

  DOI：10.1016/s0031-9422(02)00112-7

  日期：2002.6

  Investigation of whole seeds of Lupinus angustifolius L. (Leguminosae) yielded the two triterpenoid saponins with branched monosaccharide chain 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (3) and 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside (4) along with the known compounds soyasaponin 1 (1) and 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside (2). The structures of the compounds were elucidated using hydrolysis, FAB-MS and extensive NMR experiments. Compounds 2-4 showed moderate antifungal activity against Candida albicans with MIC values of 25, 25 and 30 mug/ml, respectively. Only soyasaponin I was found weakly hemolytic (HC50 > 500 mug/ml). (C) 2002 Elsevier Science Ltd. All rights reserved.