1-O-β-D-glucopyranosyl-(2S,3R,4E,11E)-2-(2'R-hydroxyhexadecenoylamino)-4,11-octadecadiene-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 1-O-β-D-glucopyranosyl-(2S,3R,4E,11E)-2-(2'R-hydroxyhexadecenoylamino)-4,11-octadecadiene-1,3-diol
• 英文别名: pinelloside；(2R)-2-hydroxy-N-[(2S,3R,4E,11E)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,11-dien-2-yl]hexadecanamide
• 化学式: C₄₀H₇₅NO₉
• 分子量: 714.037
• InChiKey: IASCSWGEBWPMAV-RWPFLKGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  50
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-O-β-D-glucopyranosyl-(2S,3R,4E,11E)-2-(2'R-hydroxyhexadecenoylamino)-4,11-octadecadiene-1,3-diol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 生成 methyl (R)-2-hydroxyhexadecanoate 、 甲基 Β-D-吡喃葡萄糖苷 、 (4E,11E)-(2S,3R)-2-Amino-octadeca-4,11-diene-1,3-diol
  参考文献：
  名称：

  Pinelloside, an antimicrobial cerebroside from Pinellia ternata

  摘要：

  An antimicrobial cerebroside, pinelloside, was isolated from the air-dried tubers of Pinellia ternata (Thunb.) Breit. Its structure was determined as 1-O-beta-D-glucopyranosyl-(2S,3R,4E,11E)-2-(2'R-hydroxyhexadecenoylamino)-4,11-octadecadiene-1,3-diol by chemical transformation and extensive spectroscopic analyses (IR, MS, H-1 and C-13 NMR, DEPT as well as 2D NMR techniques HMBC, HMQC, H-1-H-1 COSY and NOESY). The antimicrobial assay showed that this compound was inhibitory to the growth of Bacillus subtilis, Staphylococcus aureus, Aspergillus niger and Candida albicans, with minimum inhibitory concentrations (MICs) of 20, 50, 30 and 10 mug/ml, respectively. The MICs of penicillin G against bacteria B. subtilis, S. aureus, E. coli, P.,fluorescens and H. pylori were 0.80, 0.34, 0.56, 1.34 and 0.92, and those of ketoconazole against fungi A. niger, C. albicans and T. rubrum 0.90, 0.65 and 1.0 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00421-7

文献信息

• Pinelloside, an antimicrobial cerebroside from Pinellia ternata
  作者：J.H Chen、G.Y Cui、J.Y Liu、R.X Tan

  DOI：10.1016/s0031-9422(03)00421-7

  日期：2003.10

  An antimicrobial cerebroside, pinelloside, was isolated from the air-dried tubers of Pinellia ternata (Thunb.) Breit. Its structure was determined as 1-O-beta-D-glucopyranosyl-(2S,3R,4E,11E)-2-(2'R-hydroxyhexadecenoylamino)-4,11-octadecadiene-1,3-diol by chemical transformation and extensive spectroscopic analyses (IR, MS, H-1 and C-13 NMR, DEPT as well as 2D NMR techniques HMBC, HMQC, H-1-H-1 COSY and NOESY). The antimicrobial assay showed that this compound was inhibitory to the growth of Bacillus subtilis, Staphylococcus aureus, Aspergillus niger and Candida albicans, with minimum inhibitory concentrations (MICs) of 20, 50, 30 and 10 mug/ml, respectively. The MICs of penicillin G against bacteria B. subtilis, S. aureus, E. coli, P.,fluorescens and H. pylori were 0.80, 0.34, 0.56, 1.34 and 0.92, and those of ketoconazole against fungi A. niger, C. albicans and T. rubrum 0.90, 0.65 and 1.0 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.