aesculioside II_e

• 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: aesculioside II_e
• 英文别名: Aesculioside IIe；(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-9-acetyloxy-7,8-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• 化学式: C₅₄H₈₄O₂₄
• 分子量: 1117.25
• InChiKey: HRCMJHBUDCRPJF-XUPRUOONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  78
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  388
• 氢给体数：
  13
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  aesculioside II_e 在 sodium hydroxide 作用下， 反应 4.0h， 以2.3 mg的产率得到aesculioside I_b
  参考文献：
  名称：

  Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.

  摘要：

  Continued chemical investigation on the fruits of North American Aesculus pavia L. resulted in the isolation and identification of 13 polyhydroxyoleanene pentacyclic triterpenoid saponins, named aesculiosides IIe-IIk (1-7), and IIIa-IIIf (8-13), together with 18 known compounds: aesculiosides la-le (14-18), IIa-IId (19-22), IVa-lVc (23-25), 3-O-[P-D-galactopyranosyl(I 2)]-alpha-L-arabinofuranosyl(1 -> 4)-beta-D-glucuronopyranosyl-21,22-O-diangeloyl-3 beta,15a,16ot,210,22oc,28-hexahydroxyolean-12-ene (26), 3-O-[D-D-glucopyranosy](1 -> 2)]-alpha-L-arabinofuranosyl(I -> 3)-beta-D-glucuronopyranosyl-21,22-O-diangeloyl-3 beta,16ot,210,22 alpha,240,28-hexahydroxyolean-12-ene (27), 3-O-[D-D-galactopyranosyl(I -> 2)]-alpha-L-arabinofuranosyl(13)-beta-D-glucuronopyranosyl-21,22-0-diangeloyl-3p,16ot,21 beta,22 alpha,28-pentahydroxyolean- I 2-ene (28), R I -barrigenol (29), scopolin (30), and 5-methoxyscopolin (31). The structures of these compounds were elucidated by spectroscopic and chemical analyses. Compounds 14-22 and 26-28 were tested in vitro for their activity against 59 cell lines from nine different human cancers including leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast. It was found that compounds with two-acyl groups at C-21 and C-22 had cytotoxic activity for all cell lines tested with GI(50) 0.1758.71 mu, while compounds without acyl groups at C-21 and C-22 had weak or no cytotoxic activity. These results suggest that the acyl groups at C-21 and C-22 are essential for their activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.05.020

文献信息

• Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.
  作者：Zhizhen Zhang、Shiyou Li

  DOI：10.1016/j.phytochem.2007.05.020

  日期：2007.8

  Continued chemical investigation on the fruits of North American Aesculus pavia L. resulted in the isolation and identification of 13 polyhydroxyoleanene pentacyclic triterpenoid saponins, named aesculiosides IIe-IIk (1-7), and IIIa-IIIf (8-13), together with 18 known compounds: aesculiosides la-le (14-18), IIa-IId (19-22), IVa-lVc (23-25), 3-O-[P-D-galactopyranosyl(I 2)]-alpha-L-arabinofuranosyl(1 -> 4)-beta-D-glucuronopyranosyl-21,22-O-diangeloyl-3 beta,15a,16ot,210,22oc,28-hexahydroxyolean-12-ene (26), 3-O-[D-D-glucopyranosy](1 -> 2)]-alpha-L-arabinofuranosyl(I -> 3)-beta-D-glucuronopyranosyl-21,22-O-diangeloyl-3 beta,16ot,210,22 alpha,240,28-hexahydroxyolean-12-ene (27), 3-O-[D-D-galactopyranosyl(I -> 2)]-alpha-L-arabinofuranosyl(13)-beta-D-glucuronopyranosyl-21,22-0-diangeloyl-3p,16ot,21 beta,22 alpha,28-pentahydroxyolean- I 2-ene (28), R I -barrigenol (29), scopolin (30), and 5-methoxyscopolin (31). The structures of these compounds were elucidated by spectroscopic and chemical analyses. Compounds 14-22 and 26-28 were tested in vitro for their activity against 59 cell lines from nine different human cancers including leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast. It was found that compounds with two-acyl groups at C-21 and C-22 had cytotoxic activity for all cell lines tested with GI(50) 0.1758.71 mu, while compounds without acyl groups at C-21 and C-22 had weak or no cytotoxic activity. These results suggest that the acyl groups at C-21 and C-22 are essential for their activity. (c) 2007 Elsevier Ltd. All rights reserved.