3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid

• 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-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid
• 英文别名: Presapogenin-CP4；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-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
• 化学式: C₄₆H₇₄O₁₅
• 分子量: 867.085
• InChiKey: QDYPTQWAAOGCJD-OVCPMTGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  61
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以348 mg的产率得到齐墩果酸
  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：

  benzyl oleanolate 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1 → 3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以74%的产率得到3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid
  参考文献：
  名称：

  Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives

  摘要：

  Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of alpha-L-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C-3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, alpha-L-rhamnosyl moiety linked to C-2-OH of the first monosaccharide (alpha-L-alabinose, beta-D-xylose, beta-n-galactose or beta-D-glucose) in C-3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.016

文献信息

• Oleanane-type glycosides from the roots of Weigela florida “rumba” and evaluation of their antibody recognition
  作者：Anne-Sophie Champy-Tixier、Anne-Claire Mitaine-Offer、Feliciana Real Fernández、Tomofumi Miyamoto、Chiaki Tanaka、Anna-Maria Papini、Marie-Aleth Lacaille-Dubois

  DOI：10.1016/j.fitote.2018.04.017

  日期：2018.7

  Three triterpene glycosides were isolated from the roots of Weigela florida "rumba" (Bunge) A. DC.: two previously undescribed 3-O-beta-D-xylopyranosyl-(1 -> 2)-beta-D-xylopyranosyl-(1 -> 4)]-beta-D-xylopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-rharnnopyranosyl-(1 -> 2)-a-t-arabinopyranosyloleanolic acid (1) and 3-O-beta-D-xylopyranosyl-(1 -> 2)-[beta-D-glucopyranosyl-(1 -> 4)]-O-D-xylopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-rhamnopyr-anosyl-(1 -> 2)-alpha-L-arabinopyranosyloleanolic acid (2), and one isolated for the first time from a natural source 3-O-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyloleanolic acid (3). Their structures were elucidated mainly by 2D NMR spectroscopic analysis (COSY, TOCSY, NOESY, HSQC, HMBC) and mass spectrometry. Compounds 2 and 3 were further evaluated as antigens in enzyme-linked immunosorbent assay (ELISA) to recognize IgM antibodies in multiple sclerosis (MS) patients' sera.
• Triterpene glycosides and their genins fromThalictrum foetidum. I. The structure of foetoside C
  作者：T. V. Ganenko、M. I. Isaev、T. T. Gorovits、A. S. Gromova、V. I. Lutskii、A. A. Semenov、N. K. Abubakirov

  DOI：10.1007/bf00574329

  日期：1984.7
• Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives
  作者：Qingchao Liu、Hongchun Liu、Lei Zhang、Tiantian Guo、Peng Wang、Meiyu Geng、Yingxia Li

  DOI：10.1016/j.ejmech.2013.04.016

  日期：2013.6

  Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of alpha-L-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C-3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, alpha-L-rhamnosyl moiety linked to C-2-OH of the first monosaccharide (alpha-L-alabinose, beta-D-xylose, beta-n-galactose or beta-D-glucose) in C-3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.