beta-常春藤素 | 35790-95-5

• 物质功能分类: 生物化工 - 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
• 中文名称: beta-常春藤素
• 中文别名: Alpha-常春藤皂苷；a－常春藤苷；Α-常春藤素
• 英文名称: β-hederin
• 英文别名: 3-β-[(O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid；3β-[(O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid；3β-[(O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid；oleanolic acid 3-O-2)-O-α-L-arabinopyranoside>；oleanolic acid 3-O-2)-α-L-arabinopyranoside>；3-O-<α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranosyl> oleanolic acid；beta-Hederin；(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-carboxylic acid
• CAS: 35790-95-5
• 化学式: C₄₁H₆₆O₁₁
• 分子量: 734.968
• InChiKey: IBAJNOZMACNWJD-HVUPOBLPSA-N

物化性质

• 熔点：
  221-223℃
• 沸点：
  817.8±65.0 °C(Predicted)
• 密度：
  1.28
• 溶解度：
  甲醇（微量）、吡啶（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  52
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  11

安全信息

• 储存条件：
  2-8℃，避光，密封保存。

制备方法与用途

生物活性方面，β-胡萝Ix（β-Hederin）是一种从欧洲常春藤（Hedera helix L., 属于五加科）中分离出的皂苷，显示出抗利什曼原虫活性。在L. mexicana 原鞭毛体、L. mexicana 无鞭毛体和THP1细胞中的半数抑制浓度（IC50）分别为1.5 μM、68 nM 和4.57 μM。

反应信息

• 作为反应物：
  描述：

  beta-常春藤素 、 碘甲烷 在 sodium hydride 作用下， 反应 5.0h， 以37 mg的产率得到
  参考文献：
  名称：

  Triterpene glycosides and their genins fromThalictrum foetidum. I. The structure of foetoside C

  摘要：

  DOI：

  10.1007/bf00574329
• 作为产物：
  描述：

  ciwujianoside C₄ 在 2,6-二甲基吡啶 、 氢氧化钾 、 lithium iodide 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 beta-常春藤素
  参考文献：
  名称：

  Shao, Chun-Jie; Kasai, Ryoji; Xu, Jing-Da, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 2, p. 601 - 608

  摘要：

  DOI：

文献信息

• Triterpenoid saponins from Anemone raddeana
  作者：Fu Li、Cui-Rong Sun、Bin Chen、Li-Sheng Ding、Ming-Kui Wang

  DOI：10.1016/j.phytol.2012.01.007

  日期：2012.6

  Three new triterpenoid saponins, named raddeanoside R20 (1), raddeanoside R21 (2) and raddeanoside R22 (3), were isolated from the water soluble part of Anemone raddeana. The chemical structures of these new compounds were elucidated by chemical and spectroscopic methods.

  从银莲花的水溶性部分中分离出三种新的三萜皂苷，名为raddeanoside R 20（1），raddeanoside R 21（2）和raddeanoside R 22（3）。通过化学和光谱方法阐明了这些新化合物的化学结构。
• 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。
• [EN] MEDICAL USE OF PENTACYCLIC TRITERPENOID SAPONIN COMPOUND AND PHARMACEUTICAL COMPOSITION THEREOF<br/>[FR] UTILISATION MÉDICALE D'UN COMPOSÉ DE SAPONINE TRITERPÉNOÏDE PENTACYCLIQUE ET COMPOSITION PHARMACEUTIQUE ASSOCIÉE<br/>[ZH] 五环三萜皂苷化合物的医药用途及其药物组合物
  申请人：UNIV CHINA PHARMA

  公开号：WO2020244454A1

  公开（公告）日：2020-12-10

  五环三萜皂苷化合物的医药用途及其药物组合物，具体如式(I)～(XVI)所示的五环三萜皂苷在制备预防或治疗由AMPK和/或ERRα介导的疾病的药物中的用途，包括制备预防或治疗如肝脏疾病、呼吸系统疾病、代谢性疾病、自身免疫性疾病、心脑血管疾病、肾病、中枢神经系统疾病或肌营养不良症等疾病的药物。本发明预防和治疗AMPK和/或ERRα介导的疾病的药物组合物含有式(I)～(XVI)化合物或其药学上可接受的盐或溶剂化物作为活性成份和药学上可接受的辅料。
• Synthesis of β-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety
  作者：Mao-Sheng Cheng、Mao-Cai Yan、Yang Liu、Li-Gang Zheng、Jiao Liu

  DOI：10.1016/j.carres.2005.10.015

  日期：2006.1

  A facile synthetic approach toward oleanolic acid glycoside bearing alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl moiety, a unique oligosaccharide that strongly induces antitumor activity of oleanane-type triterpenoid saponins, was developed. Based on this approach P-hederin (oleanolic acid 3-0-Gt-L-rhamnopyranosyl-(1 -> 2)-alpha- L-arabinopyrano side) was efficiently prepared from oleanolic acid through stepwise glycosylation in linear eight steps with 52% overall yield, while Hederacolchiside A, (oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[beta-D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside) in linear 13 steps with 20% overall yield. (c) 2005 Published by Elsevier Ltd.
• Antiproliferative Triterpene Saponins from <i>Trevesia </i><i>p</i><i>almata</i>
  作者：Nunziatina De Tommasi、Giuseppina Autore、Aurora Bellino、Aldo Pinto、Cosimo Pizza、Raffaella Sorrentino、Pietro Venturella

  DOI：10.1021/np990231n

  日期：2000.3.1

  During the course of a study of plants of the family Araliaceae, antiproliferative activity was demonstrated by the crude saponin fraction of Trevesia palmata, After chromatographic purification, six near bisdesmosidic saponins (1-6), along with two known triterpenoid saponins, (7 and 8), were isolated. The structures of 1-6 were determined by H-1-H-1 correlation spectroscopy (COSY-DQF, 1D, TOCSY, 2D HOHAHA, 1D ROESY) and H-1-C-13 (HSQC, HMBC) spectroscopy. The antiproliferative activity of compounds 1-8 and of their prosapogenins (2a-7a) prepared by alkaline hydrolysis, was evaluated using three continuous culture cell lines.