gynosaponin TN-2 | 77658-95-8

• 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: gynosaponin TN-2
• 英文别名: (2S,3R,4R,5R,6R)-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S)-6-methyl-2-[(2R,3R,5R,8R,9R,10R,12R,13S,14R,17S)-2,3,12-trihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-5-en-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 77658-95-8
• 化学式: C₄₂H₇₂O₁₃
• 分子量: 785.026
• InChiKey: UWUZNWOONZAPGM-IXFCREGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  55
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  gynosaponin TN-2 在 硫酸 、 对甲苯磺酸 作用下， 生成 2α-hydroxypanaxadiol
  参考文献：
  名称：

  Two glycosides of a novel dammarane alcohol from Gynostemma pentaphyllum.

  摘要：

  From the aerial parts of Gynostemma pentaphyllum MAKINO (Cucurbitaceae), two glycosides were isolated, namely gynosaponin TN-1 (III), C36H62O9·3/2H2O, mp 168-173°, [α]D+34.5°and gynosaponin TN-2 (IV), C42H72O13·1/2H2O, mp 236-240°, [α]D+11.6°. On acid hydrolysis, gynosaponin TN-1 (III) yielded glucose as its sugar moiety and 2α-hydroxypanaxadiol (II), C30H52O4 as an artificial genin, while gynosaponin TN-2 (IV) afforded rutinose and II. The structure of II was elucidated to be 20, 25-epoxydammarane-2α, 3β, 12β-triol on the basis of its mass spectrum, molecular optical rotation and nuclear magnetic resonance (NMR) spectra (1H, 13C) in comparison with those of panaxadiol (I). Carbon 13 NMR spectra of III and IV indicated that their aglycone moiety has a (20S)-dammar-24-en-20-ol partial structure. Their chemical structures were established as (20S)-dammar-24-ene-2α, 3β, 12β, 20-tetraol 20-O-β-D-glucopyranoside (III) and (20S)-dammar-24-ene-2α, 3β, 12β, 20-tetraol 20-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (IV).

  DOI：

  10.1248/cpb.29.779