(3β,15α,16α)-15,16-dihydroxy-3-{{O-β-D-xylopyranosyl-(1→3)-O-α-L-arabinopyranosyl-(1→6)-O-[β-D-glucopyranosyl-(1→4)]-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl}oxy}olean-12-en-28-oic acid 28-[O-D-apio-β-D-furanosyl-(1→3)-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl] ester | 1213706-03-6

• 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: (3β,15α,16α)-15,16-dihydroxy-3-{{O-β-D-xylopyranosyl-(1→3)-O-α-L-arabinopyranosyl-(1→6)-O-[β-D-glucopyranosyl-(1→4)]-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl}oxy}olean-12-en-28-oic acid 28-[O-D-apio-β-D-furanosyl-(1→3)-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl] ester
• 英文别名: rheediinoside B；3-O-β-D-glucopyranosyl-(1->4)-O-[β-D-xylopyranosyl-(1->3)-O-α-L-arabinopyranosyl-(1->6)]-2-acetylamino-2-deoxy-β-D-glucopyranosylentagenic acid 28-O-β-apiofuranosyl-(1->3)-β-D-xylopyranosyl-(1->2)-β-D-glucopyranoside；[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aR,5S,6R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,6-dihydroxy-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
• CAS: 1213706-03-6
• 化学式: C₇₀H₁₁₃NO₃₆
• 分子量: 1544.65
• InChiKey: DTMKQNBGHUUNKB-NRRDCTGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  107
• 可旋转键数：
  20
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  580
• 氢给体数：
  21
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  (3β,15α,16α)-15,16-dihydroxy-3-{{O-β-D-xylopyranosyl-(1→3)-O-α-L-arabinopyranosyl-(1→6)-O-[β-D-glucopyranosyl-(1→4)]-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl}oxy}olean-12-en-28-oic acid 28-[O-D-apio-β-D-furanosyl-(1→3)-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl] ester 在 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 entagenic acid 3-O-β-D-glucopyranosyl-(1->4)-O-[β-D-xylopyranosyl-(1->3)-O-α-L-arabinopyranosyl-(1->6)]-2-acetylamino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Rheediinosides A and B, two antiproliferative and antioxidant triterpene saponins from Entada rheedii

  摘要：

  Two triterpenoid saponins have been isolated from the seed kernels of Entada rheedii. Their structures have been established using 1D- and 2D-NMR and mass spectrometry as 3-O-beta-D-xylopyranosyl-(1 -> 3)-O-alpha-L-arabinopyranosyl-(1 -> 6)-2-acetylamino-2-deoxy-beta-D-glucopyranosylentagenic acid 28-O-beta-apiofuranosyl-(1 -> 3)-beta-D-xylopyranosy1-(1 -> 2)-beta-D-glucopyranoside (Rheediinoside A, 1) and 3-O-beta-D-glucopyranosyl-(1 -> 3)-O-[beta-D-xylopyranosyl-(1 -> 3)-alpha-L-arabinopyranosyl-(1 -> 6)]-2-acetylamino-2-deoxy-beta-D-glucopyranosylentagenic acid 28-O-beta-apiofuranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 2)-beta-D-glucopyranoside (Rheediinoside B, 2). Compounds 1 and 2 were tested for their antiproliferative activity against T98G, A431, PC3 and B16-F1 cell lines, and further for their antioxidant properties. Moderate cytotoxic potency and antioxidant properties were found for these compounds whereas Rheediinoside B was in all assays more active than Rheedimoside A. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.10.004