3α,11α,30-trihydroxylup-20(29)-en-23,28-dioic acid

• 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: 3α,11α,30-trihydroxylup-20(29)-en-23,28-dioic acid
• 英文别名: acankoreoside P；(1R,3aS,5aR,5bR,7aR,8S,9R,11aS,11bR,12R,13aR,13bS)-9,12-dihydroxy-1-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,11a-tetramethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid
• 化学式: C₃₀H₄₆O₇
• 分子量: 518.691
• InChiKey: WFZZZGSYDQKXLZ-DPPLFAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3α,11α,30-trihydroxylup-20(29)-en-23,28-dioic acid 28-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl]ester 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 可得然胶 、 L-(+)-鼠李糖 、 3α,11α,30-trihydroxylup-20(29)-en-23,28-dioic acid
  参考文献：
  名称：

  Structure–activity relationship of lupane-triterpene glycosides from Acanthopanax koreanum on spleen lymphocyte IL-2 and IFN-γ

  摘要：

  Phytochemical investigation resulted in the isolation of three new lupane-triterpene glycosides acankoreosides M-O (1, 2 and 8) together with eight known lupane-triterpene glycosides (3-7, 9-11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-gamma were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 mu M) significantly increased IFN-gamma and IL-2 release in spleen cells. Crown Copyright (c) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.044

文献信息

• Structure–activity relationship of lupane-triterpene glycosides from Acanthopanax koreanum on spleen lymphocyte IL-2 and IFN-γ
  作者：Nguyen Xuan Nhiem、Phan Van Kiem、Chau Van Minh、Bui Huu Tai、Nguyen Huu Tung、Do Thi Ha、Kwang Su Soung、Jun Ho Kim、Ji Young Ahn、Young-Mi Lee、Young Ho Kim

  DOI：10.1016/j.bmcl.2010.06.044

  日期：2010.8

  Phytochemical investigation resulted in the isolation of three new lupane-triterpene glycosides acankoreosides M-O (1, 2 and 8) together with eight known lupane-triterpene glycosides (3-7, 9-11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-gamma were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 mu M) significantly increased IFN-gamma and IL-2 release in spleen cells. Crown Copyright (c) 2010 Published by Elsevier Ltd. All rights reserved.