intrapilosine VII

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: intrapilosine VII
• 英文别名: intrapilosin VII；[(2S,3R,4R,5S,6S)-5-[(2S,3R,4S,5S,6S)-3-hydroxy-6-methyl-5-octanoyloxy-4-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-6-methyl-2-[[(1R,3S,5S,6R,7R,8R,20S,22R,24R,25R,26S)-7,25,26-trihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.03,8]hexacosan-6-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] dodecanoate
• 化学式: C₇₅H₁₂₂O₂₆
• 分子量: 1439.78
• InChiKey: IVMMSJHGYZIPPO-WMGFSQLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  101
• 可旋转键数：
  35
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  359
• 氢给体数：
  8
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  intrapilosine VII 在 potassium hydroxide 作用下， 以 水 为溶剂， 生成 月桂酸 、 辛酸 、 肉桂酸 、 (11S)-jalapinolic acid 11-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-[α-L-rhamnopyranosyl-(1->4)]-O-[α-L-rhamnopyranosyl-(1->2)]-β-D-fucopyranoside
  参考文献：
  名称：

  Resin glycosides from Ipomoea wolcottiana as modulators of the multidrug resistance phenotype in vitro

  摘要：

  Recycling liquid chromatography was used for the isolation and purification of resin glycosides from the CHCl3-soluble extracts prepared using flowers of Ipomoea wolcottiana Rose var. wolcottiana. Bioassay guided fractionation, using modulation of both antibiotic activity against multidrug-resistant strains of Gram-negative bacteria and vinblastine susceptibility in breast carcinoma cells, was used to isolate the active glycolipids as modulators of the multidrug resistance phenotype. An ester-type dimer, wolcottine I, one tetra- and three pentasaccharides, wolcottinosides I-IV, in addition to the known intrapilosin VII, were characterized by NMR spectroscopy and mass spectrometry. In vitro assays established that none of these metabolites displayed antibacterial activity (MIC > 512 mu g/mL) against multidrug-resistant strains of Escherichia coli, and two nosocomial pathogens: Salmonella enterica serovar Typhi and Shigella flexneri; however, when tested (25 mu g/mL) in combination with tetracycline, kanamycin or chloramphenicol, they exerted a potentiation effect of the antibiotic susceptibility up to eightfold (64 mu g/mL from 512 mu g/mL). It was also determined that these non-cytotoxic (CI50 > 8.68 mu M) agents modulated vinblastine susceptibility at 25 mu g/mL in MFC-7/Vin(+) cells with a reversal factor (RFMcF-7/Vin+) of 2-130 fold. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2016.01.004