3-O-<α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl>-28-O-<β-D-glucopyranosyl(1->6)-β-D-glucopyranosyl>oleanolic acid | 120481-40-5

• 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-<α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl>-28-O-<β-D-glucopyranosyl(1->6)-β-D-glucopyranosyl>oleanolic acid
• 英文别名: 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]oleanolic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester；3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl oleanolic acid 28-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester；3-O-[β-D-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-28-O-[β-D-glucopyrannosyl-(1→6)-β-D-glucopyrannoside]oleanlic acid；3-O-[α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl]-28-O-[β-D-glucopyranosyl(1->6)-β-D-glucopyranosyl]oleanolic acid；[(2S,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] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-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: 120481-40-5
• 化学式: C₅₃H₈₆O₂₁
• 分子量: 1059.25
• InChiKey: NGKYAUZANWQMED-PGPCMFDVSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  74
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  334
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  3-O-<α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl>-28-O-<β-D-glucopyranosyl(1->6)-β-D-glucopyranosyl>oleanolic acid 在 氢氧化钾 作用下， 反应 1.0h， 以22 mg的产率得到beta-常春藤素
  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

• Comparison of Cytoprotective Effects of Saponins Isolated from Leaves of Aralia elata SEEM. (Araliaceae) with Synthesized Bisdesmosides of Oleanoic Acid and Hederagenin on Carbon Tetrachloride-Induced Hepatic Injury.
  作者：Setsuo SAITO、Jun EBASHI、Shigeya SUMITA、Takako FURUMOTO、Yoichi NAGAMURA、Keiji NISHIDA、Isao ISIGURO

  DOI：10.1248/cpb.41.1395

  日期：——

  acetate buffer (pH 4.7) gave compounds 28 and 29, respectively. Cytoprotective effects of the synthesized triterpenoidal saponins against CCl4-induced hepatic injury were compared with those of saponins isolated from the leaves of Aralia elata Seem. (Araliaceae) using isolated hepatocytes from rat liver. Although the monodesmosides 1-4 having neutral sugar components only at the O-3 position on the

  3-O-（2,3,4-三-O-乙酰基-α-L-鼠李糖基吡喃糖基（1-> 2）-3,4-二-O-乙酰基-α-L-阿拉伯吡喃糖基）-23的糖基化-O-乙酰基二十碳三烯（15）与单-（16），二-（17）和三糖溴化物（18）分别生成双desmoside过乙酸盐19、20和22，将其用5％KOH的MeOH处理得到bisdesmosides 25-27。在乙酸盐缓冲液（pH 4.7）中用β-D-葡糖苷酶水解具有β-D-吡喃葡萄糖作为末端糖组分的糖苷6和9，分别得到化合物28和29。将合成的三萜皂苷对CCl4诱导的肝损伤的细胞保护作用与从Aralia elata Seem叶片中分离的皂苷的细胞保护作用进行了比较。（菊科）使用从大鼠肝脏分离的肝细胞。尽管仅在糖苷配基的O-3位置具有中性糖成分的一糖苷1-4没有细胞保护作用，但是即使在糖苷配基的O-3和O-28位置均具有糖成分的双糖苷具有强效作用。糖成分的
• 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。