3-O-(β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl)-28-O-(α-L-rhamnopyranosyl-(1->3)[β-D-xylopyranosyl-(1->4)]-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-16α-hydroxyprotobassic 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: 3-O-(β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl)-28-O-(α-L-rhamnopyranosyl-(1->3)[β-D-xylopyranosyl-(1->4)]-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-16α-hydroxyprotobassic acid
• 英文别名: [(2S,3R,4S,5S)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-5-[(2S,3R,4R,5R)-3-hydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bR)-5,8,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• 化学式: C₆₉H₁₁₂O₃₇
• 分子量: 1533.63
• InChiKey: ODOAWXKRQVTYBL-LIBOUYBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.4
• 重原子数：
  106
• 可旋转键数：
  18
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  591
• 氢给体数：
  22
• 氢受体数：
  37

反应信息

• 作为反应物：
  描述：

  3-O-(β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl)-28-O-(α-L-rhamnopyranosyl-(1->3)[β-D-xylopyranosyl-(1->4)]-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-16α-hydroxyprotobassic acid 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 D-木糖 、 L-阿拉伯糖 、 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Triterpenoid saponins from a cytotoxic root extract of Sideroxylon foetidissimum subsp. gaumeri

  摘要：

  Evaluation of the cytotoxicity of an ethanolic root extract of Sideroxylon foetidissimum subsp. gaumeri (Sapotaceae) revealed activity against the murine macrophage-like cell line RAW 264.7. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which four saponins were isolated. Use of 1D (H-1, C-13, DEPT135) and 2D (COSY, TOCSY, HSQC, and HMBC) NMR, mass spectrometry and sugar analysis gave their structures as 3-O-(beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, 3-O-(beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, and the known compound, 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-protobassic acid. Two further saponins were obtained from the same fraction, but as a 5:4 mixture comprising 3-O-(beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid and 3-O-(beta-D-apiofuranosyl-(1 -> 3)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, respectively. This showed greater cytotoxicity (IC50 = 11.9 +/- 1.5 mu g/ml) towards RAW 264.7 cells than the original extract (IC50 = 39.5 +/- 4.1 mu g/ml), and the saponin-containing fraction derived from it (IC50 = 33.7 +/- 6.2 mu g/ml). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.03.014

文献信息

• Triterpenoid saponins from a cytotoxic root extract of Sideroxylon foetidissimum subsp. gaumeri
  作者：Alberto Sánchez-Medina、Philip C. Stevenson、Solomon Habtemariam、Luis M. Peña-Rodríguez、Olivia Corcoran、Anthony I. Mallet、Nigel C. Veitch

  DOI：10.1016/j.phytochem.2009.03.014

  日期：2009.4

  Evaluation of the cytotoxicity of an ethanolic root extract of Sideroxylon foetidissimum subsp. gaumeri (Sapotaceae) revealed activity against the murine macrophage-like cell line RAW 264.7. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which four saponins were isolated. Use of 1D (H-1, C-13, DEPT135) and 2D (COSY, TOCSY, HSQC, and HMBC) NMR, mass spectrometry and sugar analysis gave their structures as 3-O-(beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, 3-O-(beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, and the known compound, 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-protobassic acid. Two further saponins were obtained from the same fraction, but as a 5:4 mixture comprising 3-O-(beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid and 3-O-(beta-D-apiofuranosyl-(1 -> 3)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)[beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl)-16 alpha-hydroxyprotobassic acid, respectively. This showed greater cytotoxicity (IC50 = 11.9 +/- 1.5 mu g/ml) towards RAW 264.7 cells than the original extract (IC50 = 39.5 +/- 4.1 mu g/ml), and the saponin-containing fraction derived from it (IC50 = 33.7 +/- 6.2 mu g/ml). (C) 2009 Elsevier Ltd. All rights reserved.