(6S,13S)-6-O-[4-O-acetyl-β-D-glucopyranosyl-(1->4)-α-L-rhamnopyranosyl]cleroda-3,14-dien-13-ol

• 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: (6S,13S)-6-O-[4-O-acetyl-β-D-glucopyranosyl-(1->4)-α-L-rhamnopyranosyl]cleroda-3,14-dien-13-ol
• 英文别名: [(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5R,6R)-6-[[(1S,3R,4R,4aR,8aR)-4-[(3S)-3-hydroxy-3-methylpent-4-enyl]-3,4,8,8a-tetramethyl-1,2,3,4a,5,6-hexahydronaphthalen-1-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] acetate
• 化学式: C₃₄H₅₆O₁₂
• 分子量: 656.811
• InChiKey: SLDGGCPOPCDAER-HEMLPZHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  185
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (6S,13S)-6-O-[4-O-acetyl-β-D-glucopyranosyl-(1->4)-α-L-rhamnopyranosyl]cleroda-3,14-dien-13-ol 在 盐酸 作用下， 反应 6.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Tetranorclerodanes and Clerodane-Type Diterpene Glycosides from Dicranopteris dichotoma

  摘要：

  The acetone extract of Dicranopteris dichotoma afforded two new tetranorclerodanes, 18-hydroxyaylthonic acid (1) and 18-oxo-aylthonic acid (2), and four new clerodane-type diterpene glycosides, (6S,13S)-6-O-[6-O-acetyl-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl]cleroda-3,14-dien-13-ol (3), (6S,13S)-6-O-[4-O-acetyl-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl]cleroda-3,14-dien-13-ol (4), 6-O-[6-O-acetyl-beta-D-glucopyranos-yl-(1 -> 4)-alpha-L-rhamnopyranosyl]-(13E)-cleroda-3,13-dien-15-ol (5), and 6-O-[beta-D-glucopyranosyl]-(1 -> 4)-alpha-L-rhamnopyranosyl-(13E)-cleroda-3,13-dien-15-ol (6), together with two known compounds, aylthonic acid (7) and (6S,13S)-cleroda-3,14-diene-6,13-diol (8). The structures of these new compounds were established by a combination of 1D and 2D NMR techniques, MS, and acid hydrolysis. Compound 8 showed modest anti-HIV-1 activity.

  DOI：

  10.1021/np0603166

文献信息

• Tetranorclerodanes and Clerodane-Type Diterpene Glycosides from <i>Dicranopteris dichotoma</i>
  作者：Xiao-Li Li、Liu-Meng Yang、Yu Zhao、Rui-Rui Wang、Gang Xu、Yong-Tang Zheng、Lin Tu、Li-Yan Peng、Xiao Cheng、Qin-Shi Zhao

  DOI：10.1021/np0603166

  日期：2007.2.1

  The acetone extract of Dicranopteris dichotoma afforded two new tetranorclerodanes, 18-hydroxyaylthonic acid (1) and 18-oxo-aylthonic acid (2), and four new clerodane-type diterpene glycosides, (6S,13S)-6-O-[6-O-acetyl-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl]cleroda-3,14-dien-13-ol (3), (6S,13S)-6-O-[4-O-acetyl-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl]cleroda-3,14-dien-13-ol (4), 6-O-[6-O-acetyl-beta-D-glucopyranos-yl-(1 -> 4)-alpha-L-rhamnopyranosyl]-(13E)-cleroda-3,13-dien-15-ol (5), and 6-O-[beta-D-glucopyranosyl]-(1 -> 4)-alpha-L-rhamnopyranosyl-(13E)-cleroda-3,13-dien-15-ol (6), together with two known compounds, aylthonic acid (7) and (6S,13S)-cleroda-3,14-diene-6,13-diol (8). The structures of these new compounds were established by a combination of 1D and 2D NMR techniques, MS, and acid hydrolysis. Compound 8 showed modest anti-HIV-1 activity.