medicagenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester

• 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: medicagenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester
• 化学式: C₅₂H₈₂O₁₈
• 分子量: 995.212
• InChiKey: ZEQHEUKTKGCRFE-ILMMPUAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  70.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  285.5
• 氢给体数：
  8.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  medicagenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester 在 水 、 potassium hydroxide 作用下， 反应 2.0h， 生成 (2R,3R)-3-羟基-2-甲基丁酸
  参考文献：
  名称：

  Acylated oleanane-type saponins from Ganophyllum giganteum

  摘要：

  Five oleanane-type saponins, 3-O-beta-D-glucuronopyranosylzanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (1), 3-O-beta-D-glucopyranosylzanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (2), zanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (3), zanhic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)3-hydroxy-2-methyl-butyroyloxyl]-beta-D-fucopyranosyl ester (4), medicagenic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-beta-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the beta-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.11.003

文献信息

• Acylated oleanane-type saponins from Ganophyllum giganteum
  作者：Elier Galarraga Montes、Anne-Claire Mitaine-Offer、Juan Manuel Amaro-Luis、Thomas Paululat、Clément Delaude、Laurent Pouységu、Stéphane Quideau、Luis B. Rojas、Stéphanie Delemasure、Patrick Dutartre、Marie-Aleth Lacaille-Dubois

  DOI：10.1016/j.phytochem.2013.11.003

  日期：2014.2

  Five oleanane-type saponins, 3-O-beta-D-glucuronopyranosylzanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (1), 3-O-beta-D-glucopyranosylzanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (2), zanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (3), zanhic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)3-hydroxy-2-methyl-butyroyloxyl]-beta-D-fucopyranosyl ester (4), medicagenic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-beta-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the beta-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated. (C) 2013 Elsevier Ltd. All rights reserved.