15,16-dihydroxy-3-[[O-β-D-xylopyranosyl-(1->2)-O-α-L-arabinopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,15α,16α)-olean-12-en-28-oic acid O-D-apio-β-D-furanosyl-(1->3)-O-β-D-xylopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->4)]-6-O-[(2E,6R)-6-hydroxy-2,6-dimethyl-1-oxo-2,7-octadienyl]-β-D-glucopyranosyl ester | 1307232-69-4

• 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: 15,16-dihydroxy-3-[[O-β-D-xylopyranosyl-(1->2)-O-α-L-arabinopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,15α,16α)-olean-12-en-28-oic acid O-D-apio-β-D-furanosyl-(1->3)-O-β-D-xylopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->4)]-6-O-[(2E,6R)-6-hydroxy-2,6-dimethyl-1-oxo-2,7-octadienyl]-β-D-glucopyranosyl ester
• 英文别名: polystachyasaponin；[(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-hydroxy-6-[[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]oxymethyl]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-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)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-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: 1307232-69-4
• 化学式: C₈₀H₁₂₇NO₃₈
• 分子量: 1710.87
• InChiKey: BBHCOCPAQRRKFE-ZCKCMRLGSA-N

物化性质

• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  119
• 可旋转键数：
  27
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  606
• 氢给体数：
  21
• 氢受体数：
  38

反应信息

• 作为反应物：
  描述：

  15,16-dihydroxy-3-[[O-β-D-xylopyranosyl-(1->2)-O-α-L-arabinopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,15α,16α)-olean-12-en-28-oic acid O-D-apio-β-D-furanosyl-(1->3)-O-β-D-xylopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->4)]-6-O-[(2E,6R)-6-hydroxy-2,6-dimethyl-1-oxo-2,7-octadienyl]-β-D-glucopyranosyl ester 在 水 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以35 mg的产率得到15,16-dihydroxy-3-[[O-β-D-xylopyranosyl-(1->2)-O-α-L-arabinopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,15α,16α)-olean-12-en-28-oic acid O-D-apio-β-D-furanosyl-(1->3)-O-β-D-xylopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->4)]-β-D-glucopyranosyl ester
  参考文献：
  名称：

  Polystachyasaponin with Adjuvant Activity from Entada polystachya

  摘要：

  一种新的复杂三萜皂苷，多穗豆皂苷，通过色谱方法从多穗豆（Entada polystachya（L.）DC.（豆科））的叶子中分离出来。其结构被确定为15,16-二羟基-3-[[O-β-D-木糖苷-(1→2)-O-α-L-阿拉伯糖苷-(1→6)-2-(乙酰氨基)-2-脱氧-β-D-葡萄糖苷基]氧]-(3β,15α,16α)-熊果-12-烯-28-酸O-D-阿匹酰-β-D-呋喃糖苷-(1→3)-O-β-D-木糖苷-(1→2)-O-[β-D-葡萄糖苷-(1→4)]-6-O-[(2E,6R)-6-羟基-2,6-二甲基-1-氧代-2,7-辛二烯基]-β-D-葡萄糖苷酯。通过详细分析1H和13C NMR光谱，包括2D NMR光谱技术和化学转化，进行了结构阐明。使用体外实验评估了皂苷的溶血活性，并使用体内实验调查了其对卵清蛋白抗原细胞免疫反应的佐剂潜力。

  DOI：

  10.1515/znb-2010-0514