(+)-3-O-β-D-fucopyranosylperiplogenin | 63813-72-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (+)-3-O-β-D-fucopyranosylperiplogenin
• 英文别名: 3-O-β-D-fucopyranosylperiplogenin；ledienoside；Ledienosid；3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 63813-72-9
• 化学式: C₂₉H₄₄O₉
• 分子量: 536.663
• InChiKey: RAWRNCRYFFPACC-PSFZZMHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+)-3-O-β-D-fucopyranosylperiplogenin 在 盐酸 、 (-)-α-methylbenzylamine 、 sodium cyanoborohydride 、 乙酸酐 作用下， 以 甲醇 、 水 、 吡啶 为溶剂， 反应 3.0h， 生成 D-Fucose
  参考文献：
  名称：

  Cardenolides from Saussurea stella with Cytotoxicity toward Cancer Cells

  摘要：

  Three new cardenolides, 3-O-beta-D-fucopyranosylstrophanthidin (1), 3-O-beta-D-quinovopyranosylperiplogenin (2), and 3-O-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosylcannogenin (3), together with seven known cardenolides (4-10), were isolated from a cytotoxic ethanol extract of the whole dried plants of Saussurea stella. The structures of these compounds were established by spectroscopic and chemical methods. When the cytotoxicity of compounds 2-10 toward Bel-7402 human hepatoma cells and BGC-823 human gastric cancer cells was evaluated, all compounds showed IC50 values of <1 mu M for both cell lines. This is the first report of cardenolides occurring in a species of the family Asteraceae.

  DOI：

  10.1021/np070150o

文献信息

• Die Glykoside der Samen vonStrophanthus Eminii Asch et Pax. 3. Mitteilung. Glykoside und Aglykone, 184. Mitteilung
  作者：R. Zelnik、O. Schindler

  DOI：10.1002/hlca.19570400711

  日期：——

  papierchromatographischer Kontrolle der einzelnen Isolierungsstufen untersucht. Als Hauptglykoside wurden die früher schon erhaltenen Glykoside Cymarin, Cymarol, Periplocymarin und Emicymarin isoliert. Von diesen waren Cymarin, Periplocymarin und Emicymarin von den entsprechenden Allo-( = 17 α-)-Verbindungen begleitet. Daneben wurden amorphe, papierchromatographisch einheitliche Glykoside erhalten, deren Konstitution

  Strophanthus Eminii Asch et Pax种子的洋地黄苷苷的组成。用纸色谱控制各个分离阶段进行了检测。分离先前获得的糖苷cymarin，cymarol，peripycymarin和emicymarin作为主要糖苷。其中，cymarin，periporcycymarin和emicymarin伴随有相应的同素（= 17α-）化合物。另外，获得了根据纸色谱法均匀的无定形糖苷，其结构无法阐明。获得结晶形式的来迪乐甙和相应的同素化合物，作为另一种次级糖苷。以前怀疑的组成是通过ledienoside的酸水解证实的。
• Cardenolides from <i>Saussurea stella</i> with Cytotoxicity toward Cancer Cells
  作者：Tian-Min Wang、Toshinari Hojo、Fu-Xiang Ran、Ru-Feng Wang、Rui-Qing Wang、Hu-Biao Chen、Jing-Rong Cui、Ming-Ying Shang、Shao-Qing Cai

  DOI：10.1021/np070150o

  日期：2007.9.1

  Three new cardenolides, 3-O-beta-D-fucopyranosylstrophanthidin (1), 3-O-beta-D-quinovopyranosylperiplogenin (2), and 3-O-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosylcannogenin (3), together with seven known cardenolides (4-10), were isolated from a cytotoxic ethanol extract of the whole dried plants of Saussurea stella. The structures of these compounds were established by spectroscopic and chemical methods. When the cytotoxicity of compounds 2-10 toward Bel-7402 human hepatoma cells and BGC-823 human gastric cancer cells was evaluated, all compounds showed IC50 values of <1 mu M for both cell lines. This is the first report of cardenolides occurring in a species of the family Asteraceae.