α-Peltatin 5-O-β-D-glucoside | 11024-58-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: α-Peltatin 5-O-β-D-glucoside
• 英文别名: α-peltatin β-D-glucoside；(5aR)-10-β-D-glucopyranosyloxy-5t-(4-hydroxy-3,5-dimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-one；(5aR)-10-β-D-Glucopyranosyloxy-5t-(4-hydroxy-3,5-dimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-on；(5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• CAS: 11024-58-1
• 化学式: C₂₇H₃₀O₁₃
• 分子量: 562.527
• InChiKey: HUCNZRPYZDCCEF-NSLKGFGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  183
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  α-Peltatin 5-O-β-D-glucoside 在 吡啶 、 甲醇 、 乙醚 作用下， 生成 (5aR)-10-(tetra-O-acetyl-β-D-glucopyranosyloxy)-5t-(3,4,5-trimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-one
  参考文献：
  名称：

  Lignanglucoside AUS鬼臼盾叶大号。7. Mitteilungübermitosehemmende Naturstoffe †

  摘要：

  从美洲鬼臼的根茎。可以分离并鉴定具有抗有丝分裂活性的四种木脂素葡糖苷：鬼臼毒素-β-D-葡糖苷（IX），β-类维生素A-β-D-葡糖苷（XI），4'-去甲基鬼臼毒素-β-D-葡糖苷（X）和α-peltatin-β-u-葡萄糖苷（XII）。根据以下事实推论β-类维生素A-β-D-葡萄糖苷的组成：用乳胶酶解产生D-葡萄糖和已知的β-类胡萝卜素。α-Peltatin-β-D-葡萄糖苷是鬼臼类中第一个以结晶形式分离的天然葡萄糖苷，经乳化酶水解后分解为D-葡萄糖和α-peltatin。可以通过甲基化为鬼臼毒素-β-D-葡萄糖苷和β-peltatin-β-D-的甲基化来确定4'-去甲基鬼臼毒素-β-D-葡萄糖苷和α-peletatin-β-D-葡萄糖苷中糖成分的位置。糖苷。

  DOI：

  10.1002/hlca.19570400525

文献信息

• Antitumor agents. 100. Inhibition of human DNA topoisomerase II by cytotoxic ether and ester derivatives of podophyllotoxin and .alpha.-peltatin
  作者：Lee S. Thurston、Yasuhiro Imakura、Mitsumasa Haruna、De Hua Li、Zong Chao Liu、Su Ying Liu、Yung Chi Cheng、Kuo Hsiung Lee

  DOI：10.1021/jm00123a016

  日期：1989.3

  A principal mechanism of action of the clinical antitumor drugs etoposide (1) and teniposide (2) is the inhibition of catalytic activity of type II DNA topoisomerase and concurrent enzyme-mediated production of lethal DNA strand breaks. Substitution of the glycosidic moiety of 1 or 2 by ester and ethers, as well as the esterification and etherification of alpha-peltatin (4) including its glucosidic ethylidene and thenylidene cyclic acetals (25 and 26), has afforded compounds of much less activity than that of 1. The in vitro cytotoxicity (KB) appears to have no correlation with the inhibitory activity of the human DNA topoisomerase II.
• THURSTON, LEE S.;IMAKURA, YASUHIRO;HARUNA, MITSUMASA;LI, DE-HUA;LIU, ZONG+, J. MED. CHEM., 32,(1989) N, C. 604-608
  作者：THURSTON, LEE S.、IMAKURA, YASUHIRO、HARUNA, MITSUMASA、LI, DE-HUA、LIU, ZONG+

  DOI：——

  日期：——