26-O-β-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1β,3β,11α,26-tetrol 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-glucopyranoside | 1011527-17-5

• 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: 26-O-β-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1β,3β,11α,26-tetrol 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-glucopyranoside
• 英文别名: caucasicoside B；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(1S,2S,4S,8S,9S,11R,12S,13R,14R,16R)-11,14-dihydroxy-7,9,13-trimethyl-6-[3-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]but-3-enyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-6,18-dien-16-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1011527-17-5
• 化学式: C₄₅H₇₀O₁₉
• 分子量: 915.039
• InChiKey: GWNCJTZKIAESFW-OYZDMABCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  64
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  26-O-β-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1β,3β,11α,26-tetrol 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-glucopyranoside 在 盐酸 作用下， 反应 4.0h， 生成 L-rhamnopyranose
  参考文献：
  名称：

  Steroidal glycosides from the underground parts of Helleborus caucasicus

  摘要：

  Four polyhydroxylated and polyunsaturated furostanol glycosides (1-4), named caucasicosides A (1), B (2), C (3) and D (4), were isolated from the MeOH extract of the underground parts of Helleborus caucasicus, along with four spirostanol derivatives, a furostanol glycoside, a furospirostanol glycoside, 20-hydroxyecdysone and the bufadienolides hellebrigenin and deglucohellebrin. The structures of 1-4 were elucidated as furosta-5,20(22),25(27)-triene-1 beta,3tetrol,26-tetrol 26-O-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1 beta,3 beta,l11 alpha,26-tetrol 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside (2), 26-O-beta-D-glucopyranosyl (2) 22 alpha-methoxyfurosta-5,25(27)-diene-1 beta,3 beta,11,26-tetrol 3-O-beta-L-rhamnopyranosyl-(1 -> 3)-beta-D-glucopyranoside (3), 26-O-beta-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1 beta,3 beta,26-triol 3-O-beta-D-Xylopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-sulfo-alpha-L-arabinopyranoside (4). Structure elucidation was accomplished through the extensive use of 1D- and 2D NMR experiments including H-1-H-1 (COSY, 1D-TOCSY) and H-1-C-13 (HSQC, HMBC) spectroscopy along with ESI-MS and HR-ESI-MS. The aglycones of 1-4 have never been reported before. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.11.007