3-O-β-D-glucopyranosyl 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

• 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: 3-O-β-D-glucopyranosyl 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
• 英文别名: acankoreoside N；[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1R,3aS,5aR,5bR,7aR,9R,11aS,11bR,12R,13aR,13bS)-12-hydroxy-1-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a-pentamethyl-9-[(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• 化学式: C₅₄H₈₈O₂₄
• 分子量: 1121.28
• InChiKey: FTVLUTDSCPTFAR-WIFGCPSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  78
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  394
• 氢给体数：
  15
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  3-O-β-D-glucopyranosyl 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 、 三甲基硅咪唑 在 盐酸 、 吡啶 、 L-半胱氨酸甲酯盐酸盐 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.5h， 生成 (2S,3R,4S,5R,6R)-2,3,4,5-Tetrakis-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran 、 1,2,3,4-tetra-O-trimethysilyl-α-L-rhamnose
  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.