β-D-glucopyranosyl(1-2)-β-D-glucopyranosyl {3-O-β-D-glucopyranosyl(1-2)-[α-L-arabinopyranosyl(1-6)]-β-D-glucopyranosyl}oleanolate

• 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: β-D-glucopyranosyl(1-2)-β-D-glucopyranosyl {3-O-β-D-glucopyranosyl(1-2)-[α-L-arabinopyranosyl(1-6)]-β-D-glucopyranosyl}oleanolate
• 英文别名: 3-O-[α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl]-28-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]oleanolic acid；glaberrimoside B；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• 化学式: C₅₉H₉₆O₂₇
• 分子量: 1237.4
• InChiKey: JPNLVTCHCCRENP-UNIMZIJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  86
• 可旋转键数：
  15
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  433
• 氢给体数：
  16
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  β-D-glucopyranosyl(1-2)-β-D-glucopyranosyl {3-O-β-D-glucopyranosyl(1-2)-[α-L-arabinopyranosyl(1-6)]-β-D-glucopyranosyl}oleanolate 在 盐酸 、 水 作用下， 反应 2.0h， 生成 L-阿拉伯糖 、 葡萄糖 、 齐墩果酸
  参考文献：
  名称：

  Phenotype-specific apoptosis induced by three new triterpenoid saponins from Albizia glaberrima (Schumach. & Thonn.) Benth

  摘要：

  As part of our search of new bioactive saponins from Cameroonian medicinal plants, phytochemical investigation of the roots of Albizia glaberrima led to the isolation of three new oleanane-type saponins, named glaberrimosides A-C (1-3). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR (1 H, 13C NMR, and DEPT) and 2D NMR (COSY, ROESY, HSQC and HMBC) as 3-O-[alpha-L-arabinopyranosyl-(1 -> 6)-[beta-n-glucopyranosyl-(1-4 -> 2)]-O-n-glucopyranosyl]28-O-[(3-n-glucopyranosyl-(1 6)-[beta-D-glucopyranosyl-(1 -> 2)1-O-n-glucopyranosyl]-oleanolic acid (1), 3-O-[alpha-L-arabinopyranosyl-(1 -> 6)43-n-glucopyranosyl-(1 -> 2)]-(3-n-glucopyranosy1]-28-O-[3-D-glucopyranosyl-(1 -> 6)13-n-glucopyranosyl]-oleanolic acid (2), and 3-O-4[3-n-glucopyranosyl-(1 2)-beta-D-glucopyranosyl-28-O-D3-D-glucopyranosyl-(1 -> 6)-[beta-D-fucopyranosyl-(1 -> 2)]-beta-D-glucopyranosyll-oleanolic acid (3). The pro-apoptotic effect of the three saponins was evaluated on three human cell lines (pancreatic carcinoma AsPC-1, hematopoietic monocytic THP-1, and human fibroblast cell line BJ). Saponins 1-3 specifically induced apoptosis of pancreatic carcinoma cell (AsPC-1) in a dose -dependent manner. More interestingly, there were inactive on monocytic (THP-1) and normal human fibroblast (BJ) cell lines. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2015.12.012

文献信息

• Phenotype-specific apoptosis induced by three new triterpenoid saponins from Albizia glaberrima (Schumach. & Thonn.) Benth
  作者：Olivier Placide Noté、Sarah Ali Azouaou、Line Simo、Cyril Antheaume、Dominique Guillaume、Dieudonné Emmanuel Pegnyemb、Christian Dominique Muller、Annelise Lobstein

  DOI：10.1016/j.fitote.2015.12.012

  日期：2016.3

  As part of our search of new bioactive saponins from Cameroonian medicinal plants, phytochemical investigation of the roots of Albizia glaberrima led to the isolation of three new oleanane-type saponins, named glaberrimosides A-C (1-3). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR (1 H, 13C NMR, and DEPT) and 2D NMR (COSY, ROESY, HSQC and HMBC) as 3-O-[alpha-L-arabinopyranosyl-(1 -> 6)-[beta-n-glucopyranosyl-(1-4 -> 2)]-O-n-glucopyranosyl]28-O-[(3-n-glucopyranosyl-(1 6)-[beta-D-glucopyranosyl-(1 -> 2)1-O-n-glucopyranosyl]-oleanolic acid (1), 3-O-[alpha-L-arabinopyranosyl-(1 -> 6)43-n-glucopyranosyl-(1 -> 2)]-(3-n-glucopyranosy1]-28-O-[3-D-glucopyranosyl-(1 -> 6)13-n-glucopyranosyl]-oleanolic acid (2), and 3-O-4[3-n-glucopyranosyl-(1 2)-beta-D-glucopyranosyl-28-O-D3-D-glucopyranosyl-(1 -> 6)-[beta-D-fucopyranosyl-(1 -> 2)]-beta-D-glucopyranosyll-oleanolic acid (3). The pro-apoptotic effect of the three saponins was evaluated on three human cell lines (pancreatic carcinoma AsPC-1, hematopoietic monocytic THP-1, and human fibroblast cell line BJ). Saponins 1-3 specifically induced apoptosis of pancreatic carcinoma cell (AsPC-1) in a dose -dependent manner. More interestingly, there were inactive on monocytic (THP-1) and normal human fibroblast (BJ) cell lines. (C) 2015 Elsevier B.V. All rights reserved.