batatin I

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: batatin I
• 英文别名: [(2S,3R,4R,5S,6S)-2-[(2S,3S,4R,5R,6S)-3-[(2S,3R,4S,5S,6S)-5-dodecanoyloxy-3-hydroxy-6-methyl-4-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-2-methyl-5-[(2R)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22S,23S,24S,26R)-4,5,26-trihydroxy-6,24-dimethyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-23-yl]oxy]oxan-4-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] (11R)-11-[(2R,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5S,6S)-5-[(2S,3R,4R,5R,6S)-5-dodecanoyloxy-4-hydroxy-6-methyl-3-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-6-methyl-3-[(2R)-2-methylbutanoyl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxyhexadecanoate
• 化学式: C₁₄₄H₂₃₂O₅₀
• 分子量: 2763.4
• InChiKey: FNNZMFHSSZQFKV-PPQUYDQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.8
• 重原子数：
  194
• 可旋转键数：
  76
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  678
• 氢给体数：
  14
• 氢受体数：
  50

反应信息

• 作为反应物：
  描述：

  batatin I 在 氢氧化钾 作用下， 反应 2.0h， 生成 月桂酸 、 simonic acid B methyl ester 、 (S)-(+)-2-甲基丁酸 、 肉桂酸
  参考文献：
  名称：

  Batatins I and II, Ester-Type Dimers of Acylated Pentasaccharides from the Resin Glycosides of Sweet Potato

  摘要：

  Batatins I (1) and II (2), two ester-type dimers of acylated pentasaccharides, have been isolated by recycling HPLC from the hexane-soluble extract of sweet potato (Ipomoea batatas var. batatas). The structures were elucidated by a combination of high-resolution NMR spectroscopy and mass spectrometry. Complete analysis and unambiguous assignments of the H-1 and C-13 NMR spectra of 1 and 2 were achieved by 2D shift correlation measurements. The glycosidic acid forming each branched pentasaccharide monomeric unit was confirmed as simonic acid B. Three different fatty acids esterify this core at the same positions in both batatins: C-2 on the second rhamnose unit and C-4 and C-2 (or C-3) on the third rhamnose moiety. The acylating residues were identified as (+)-(2S)-methylbutanoic, dodecanoic (lauric), and cinnamic acids. The site of lactonization by the aglycon in unit A was placed at C-3 of the second saccharide. The position for the ester linkage for monomeric unit B on the macrocylic unit A was identified as C-3 of the terminal rhamnose'''. Through spectroscopic simulation of these complex oligosaccharides, the chemical shifts and coupling constants were deduced for the overlapped proton resonances with a non-first-order resolution. The experimental NMR spectroscopic values registered for batatinoside I (3), a new polyacylated macroyclic pentasaccharide also isolated from this plant, were used as the starting point for spectral simulation of 1 and 2. Both polymers 1 and 2 represent dimers of compound 3.

  DOI：

  10.1021/np070093z