3β-hydroxyoleane-12-en-28-oic acid 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside | 117585-05-4

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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-hydroxyoleane-12-en-28-oic acid 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside
• 英文别名: 3β-[(O-β-D-glucopyranosyl-(1->2)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid；oleanolic acid 3-O-β-D-glucopyranosyl-(1->2)-O-α-L-arabinopyranoside；3-O-[β-D-glucopyranosyl-(1->2)-α-L-arabinopyranosyl]oleanolic acid；oleanolic acid 3-O-β-D-glucopyranosyl-(1->2)-α-L-arabinopyranoside；oleanolic acid-3-O-β-D-glucopyranosyl-(1->2)-α-L-arabinopyranoside；3-O-β-D-glucopyranosyl-(1->2)-α-L-arabinopyranosyl oleanolic acid；Saponin PE；(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-carboxylic acid
• CAS: 117585-05-4；60213-69-6
• 化学式: C₄₁H₆₆O₁₂
• 分子量: 750.968
• InChiKey: GXWUEMSASMVWKO-LFGJQLCQSA-N

物化性质

• 熔点：
  220-221℃
• 沸点：
  849.6±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3β-hydroxyoleane-12-en-28-oic acid 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 齐墩果酸
  参考文献：
  名称：

  摘要：

  The previously known triterpenoid 3-O-alpha -L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-alpha -L-rhamnopyranosyl-(1 -->4)-O-beta -D-glucopyranosyl-(1-6)-O-beta -D-glucopyranosyl ethers of the 3-O-alpha -L-arabinopyranoside of hederagenin, and 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arbinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical Methods and (CNMR)-C-13 spectroscopy.

  DOI：

  10.1023/a:1002891507725
• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以58 mg的产率得到3β-hydroxyoleane-12-en-28-oic acid 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside
  参考文献：
  名称：

  四种具有重要抗肿瘤活性的天然三萜皂苷的简便合成

  摘要：

  通过采用逐步糖基化，首次合成了四种具有显着抗肿瘤活性的天然三萜皂苷。关键中间体 13 是通过 Bu2SnO 介导的区域选择性苯甲酰化得到的。在目标化合物的制备过程中，发现中间体17和20中的α-L-阿拉伯吡喃糖基单元以异常的1 C 4 构象存在，去除苯甲酰基后，α-L-阿拉伯吡喃糖基单元在典型的 4 C 1 形式。

  DOI：

  10.1080/00397910903576602

文献信息

• Structures of 3,28-O-bisglycosidic triterpenoid saponins of Fatsia japonica
  作者：Tadashi Aokia、Kazumi Shido、Yutaka Takahashi、Takayuki Suga

  DOI：10.1016/s0031-9422(00)98554-6

  日期：——

  Abstract Four novel 3,28- O -bisglycosidic triterpenoid saponins were isolated from the mature fruits of F. japonica . They were characterized as the 28- O -α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranosyl-(1 → 4)-β- d -glucopyranosides of 3- O -α- l -arabinopyranosyl echinocystic acid, 3- O -α- l -arabinopyranosyl hederagenin, 3- O -β- d -glucopyranosyl-(1 → 2)-α- l -arabinopyranosyl oleanolic acid

  摘要 从粳稻成熟果实中分离得到4种新型3,28-O-双糖苷三萜皂苷。它们被表征为 28- O -α- l -rhamnopyranosyl-(1 → 4)-β- d -glupyranosyl-(1 → 4)-β-d -吡喃葡萄糖苷 3- O -α- l -arabinopyranosyl echinocystic acid , 3-O-α-l-阿拉伯吡喃常春藤苷配基, 3-O-β-d-吡喃葡萄糖基-(1→2)-α-l-阿拉伯吡喃齐墩果酸和3-O-β-d-吡喃葡萄糖基-(1→2) )-α-l-阿拉伯吡喃常春藤苷配基。
• 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。
• ——
  作者：E. A. Sobolev、V. I. Grishkovets、A. S. Shashkov、N. V. Tolkacheva、V. Ya. Chirva

  DOI：10.1023/a:1002868330015

  日期：——
• Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives
  作者：Shan Qian、Jiao Hai Li、Yu Wei Zhang、Xin Chen、Yong Wu

  DOI：10.1080/10286020903405456

  日期：2010.1.1

  Glucosidations of oleanolic acid (1) and its dihydroxy-olide derivatives (2) were carried out to provide eight glycosides. All synthesized compounds were evaluated by in vitro -glucosidase inhibitory activity assay. 3-Acetyl dihydroxy-olide oleanolic derivative 15 showed the most potent inhibitory effect. Structure-activity relationships within these compounds are discussed.
• KAWAI, HIDEAKI;KUROYANAGI, MASANORI;UMEHARA, KAORU;UENO, AKIRA;SATAKE, MO+, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4769-4775
  作者：KAWAI, HIDEAKI、KUROYANAGI, MASANORI、UMEHARA, KAORU、UENO, AKIRA、SATAKE, MO+

  DOI：——

  日期：——