3-O-[β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl]oleanolic acid 28-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl] ester | 85899-62-3

• 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→2)-α-L-arabinopyranosyl]oleanolic acid 28-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl] ester
• 英文别名: [(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-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-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
• CAS: 85899-62-3
• 化学式: C₅₃H₈₆O₂₂
• 分子量: 1075.25
• InChiKey: FNNMEJXCIARVCO-WGCVIKQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  75
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  354
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  3-O-[β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl]oleanolic acid 28-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl] ester 在 氢氧化钾 作用下， 反应 1.0h， 生成 3β-hydroxyoleane-12-en-28-oic acid 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside
  参考文献：
  名称：

  Studies on the saponins of Lonicera japonica THUNB.

  摘要：

  从忍冬科植物忍冬（Lonicera japonica THUNB.新皂甙 6、9、11 和 12 的结构被确定为 3-O-α-L-阿拉伯吡喃糖基-28-O-[β-D-吡喃葡萄糖基（1→6）-β-D-吡喃葡萄糖基] 齐墩果酸、3-O-[α-L-rahmnopyranosyl（1→2）-α-L-阿拉伯吡喃糖基]-28-O-β-D-吡喃葡萄糖基 hederagenin、3-O-[α-L-吡喃鼠李糖基(1→2)-α-L-阿拉伯呋喃糖基]-28-O-[β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖基] 烯醇酸和 3-O-[α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoyl]-28-O-[6-acetyl-β-D-giucopyranosyl (1→6)-β-D-glucopyranosyl] hederagenin、通过碳-13 核磁共振波谱和化学证据，分别对[1→6]-β-D-吡喃葡萄糖基]-28-O[6-乙酰基-β-D-吡喃葡萄糖基]赤芍苷进行了研究。本研究发现，不同地点采集到的材料的皂苷成分有显著差异。在这些皂甙中，单皂甙的溶血活性较强，而双皂甙的溶血活性较弱。

  DOI：

  10.1248/cpb.36.4769

文献信息

• Studies on the saponins of Lonicera japonica THUNB.
  作者：HIDEAKI KAWAI、MASANORI KUROYANAGI、KAORU UMEHARA、AKIRA UENO、MOTOYOSHI SATAKE

  DOI：10.1248/cpb.36.4769

  日期：——

  From the aerial parts of Lonicera japonica THUNB.(Caprifoliaceae), twelve triterpenoidalsaponins having oleanolic acid and hederagenin as aglycones, were isolated.The stnuctures of fournew saponins, 6, 9, 11 and 12, were established to be 3-O-α-L-arabinopyranosyl-28-O-[β-Dglucopyramosyl (1→6)-β-D-glucopyranosyl] oleanolic acid, 3-O-[α-L-rahmnopyranosyl (1→2)-α-L-arabinopyranosyl]-28-O-β-D-glucopyramosyl hederagenin, 3-O-[α-L-rhamnopyramosyl (1→2)-α-L-arabinopyramosyl]-28-O-[β-D-glucopyramosyl (1→6)-β-D-glucopyranosyl] oieanolic acid and 3-O-[α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoyl]-28-O-[6-acetyl-β-D-giucopyranosyl (1→6)-β-D-glucopyranosyl] hederagenin, respectively, by means of carbon-13 nuclear magneticresonance spectroscopy and chemical evidence.The present studies revealed that the saponin compositionsof the materials collected at different places were significantly different from each other. Among these sapomins, monodesmosides showed strong hemolytic activity, but bisdesmosidesshowed weak hemolytic activity.

  从忍冬科植物忍冬（Lonicera japonica THUNB.新皂甙 6、9、11 和 12 的结构被确定为 3-O-α-L-阿拉伯吡喃糖基-28-O-[β-D-吡喃葡萄糖基（1→6）-β-D-吡喃葡萄糖基] 齐墩果酸、3-O-[α-L-rahmnopyranosyl（1→2）-α-L-阿拉伯吡喃糖基]-28-O-β-D-吡喃葡萄糖基 hederagenin、3-O-[α-L-吡喃鼠李糖基(1→2)-α-L-阿拉伯呋喃糖基]-28-O-[β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖基] 烯醇酸和 3-O-[α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoyl]-28-O-[6-acetyl-β-D-giucopyranosyl (1→6)-β-D-glucopyranosyl] hederagenin、通过碳-13 核磁共振波谱和化学证据，分别对[1→6]-β-D-吡喃葡萄糖基]-28-O[6-乙酰基-β-D-吡喃葡萄糖基]赤芍苷进行了研究。本研究发现，不同地点采集到的材料的皂苷成分有显著差异。在这些皂甙中，单皂甙的溶血活性较强，而双皂甙的溶血活性较弱。