3β,23-dihydroxy-30-norolean-12,20(29)-dien-28-oic acid | 117654-06-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β,23-dihydroxy-30-norolean-12,20(29)-dien-28-oic acid
• 英文别名: 30-norhederagenin；quinatic acid；(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-6a,6b,9,12a-tetramethyl-2-methylidene-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 117654-06-5
• 化学式: C₂₉H₄₄O₄
• 分子量: 456.666
• InChiKey: FKUBIEWSGBVADJ-VZBPFLCRSA-N

物化性质

• 熔点：
  241-243 °C(Solv: acetone (67-64-1))
• 沸点：
  594.3±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-β-[(β-D-glucopyranosyl-(1->3)-O-α-L-arabinopyranosyl)-oxy]-23-hydroxy-30-norolean-12-en-28-oic acid α-L-rhamnopyranosyl(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester 在 三氟乙酸 作用下， 生成 3β,23-dihydroxy-30-norolean-12,20(29)-dien-28-oic acid
  参考文献：
  名称：

  Triterpenoid saponins and phenylethanoid glycosides from stem of Akebia trifoliata var. australis

  摘要：

  A detailed phytochemical study on the 70% aqueous ethanol extract of stems of Akebia trifoliata (Thunb.) Koidz. var. australis (Diels) Rehd led to isolation of five compounds, together with 12 known triterpenoid saponins and three known phenylethanoid glycosides. The structures of the five compounds were elucidated on the basis of analysis of spectroscopic data and physicochernical properties as: 2 alpha, 3 beta, 23-trihydroxy-30-norolean-12-en-28-oic acid beta-D-glucopyranosyl ester (1), 2 alpha, 3 beta, 23-trihydroxy-30-norolean-12-en-28-oic acid beta-D-xylopyranosyl-(1 -> 3)-O-alpha-D-rhamnopyranosyl-(1 -> 4)-O-beta-D-glueopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl ester (2), 2 alpha, 3 beta, 23-trihydroxyurs- 12-en-28-oic acid beta-D-xylopyranosyl-(1 -> 3)-O-alpha-L-rhanmopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 6)-O-beta-D-gluco-pyranosyl ester (3), 3-beta-[(beta-D-glucopyranosyl-(1 -> 3)-O-alpha-L-arabinopyranosyl)oxy]-23-hydroxy-30-norolean-12-en-28-oic acid alpha-L-rhamnopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl ester (4) and 3-beta-[(alpha-L-xylopyranosyl-(1 -> 2)-O-alpha[L-arabinopyranosyl)oxy]-30-norolean-12-en-28-oic acid alpha-L-rhamnopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl ester (5), named mutongsaponin A, B, C, D and E, respectively. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2006.09.003

文献信息

• Bidesmoside triterpenoid glycosides from Stauntonia chinensis and relationship to anti-inflammation
  作者：Hao Gao、Feng Zhao、Guo-Dong Chen、Shao-Dan Chen、Yang Yu、Zhi-Hong Yao、Brad W.C. Lau、Zhao Wang、Jin Li、Xin-Sheng Yao

  DOI：10.1016/j.phytochem.2009.04.005

  日期：2009.4

  Ten triterpenoid glycosides, yemuoside YM(26-35) (1-9 and 12), were isolated from a traditional Chinese medicine known as "Ye Mu Gua" (Stauntonia chinensis DC.) along with two known ones, kalopanax saponin C (10) and sieboldianoside A (11). Their structures, as elucidated by spectroscopic analyses and chemical methods, were either penta-saccharidic or hexa-saccharidic bidesmoside triterpenoid glycosides

  从名为“野木瓜”（Stauntonia chinensis DC.）的传统中药中分离出 10 种三萜苷类，即野木苷 YM(26-35)（1-9 和 12）以及两种已知的 kalopanax saponin C (10 ) 和 sieboldianoside A (11)。通过光谱分析和化学方法阐明，它们的结构是五糖或六糖双糖苷三萜糖苷。帮助解释“野木瓜”的抗炎作用、抑制炎症介质（一氧化氮、TNF-α和IL-6）释放的1-12及其相关苷元、常春藤苷配基的临床应用（13），在体外进行了评估。发现化合物13而非1-12表现出显着的抑制活性。“野木瓜”中丰富的三萜甙 因此可能转化为各自的苷元，从而抑制体内炎症因子的释放。这可以解释“野木瓜”在抗炎作用方面的临床价值。这种对“野木卦”可能产生作用的解释类似于化学药物的前药概念，可以扩展到一些传统药物。也就是说，主要成分可能不是直接具有生物活性，而是通
• Triterpenoid saponins and phenylethanoid glycosides from stem of Akebia trifoliata var. australis
  作者：Huimin Gao、Zhimin Wang

  DOI：10.1016/j.phytochem.2006.09.003

  日期：2006.12

  A detailed phytochemical study on the 70% aqueous ethanol extract of stems of Akebia trifoliata (Thunb.) Koidz. var. australis (Diels) Rehd led to isolation of five compounds, together with 12 known triterpenoid saponins and three known phenylethanoid glycosides. The structures of the five compounds were elucidated on the basis of analysis of spectroscopic data and physicochernical properties as: 2 alpha, 3 beta, 23-trihydroxy-30-norolean-12-en-28-oic acid beta-D-glucopyranosyl ester (1), 2 alpha, 3 beta, 23-trihydroxy-30-norolean-12-en-28-oic acid beta-D-xylopyranosyl-(1 -> 3)-O-alpha-D-rhamnopyranosyl-(1 -> 4)-O-beta-D-glueopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl ester (2), 2 alpha, 3 beta, 23-trihydroxyurs- 12-en-28-oic acid beta-D-xylopyranosyl-(1 -> 3)-O-alpha-L-rhanmopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 6)-O-beta-D-gluco-pyranosyl ester (3), 3-beta-[(beta-D-glucopyranosyl-(1 -> 3)-O-alpha-L-arabinopyranosyl)oxy]-23-hydroxy-30-norolean-12-en-28-oic acid alpha-L-rhamnopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl ester (4) and 3-beta-[(alpha-L-xylopyranosyl-(1 -> 2)-O-alpha[L-arabinopyranosyl)oxy]-30-norolean-12-en-28-oic acid alpha-L-rhamnopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl ester (5), named mutongsaponin A, B, C, D and E, respectively. (c) 2006 Published by Elsevier Ltd.