1,2-O-dilauroyl-3-O-β-D-glucopyranosyl-sn-glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-O-dilauroyl-3-O-β-D-glucopyranosyl-sn-glycerol
• 英文别名: 1,2-di-O-dodecanoyl-sn-glyceryl β-D-glucopyranoside；[(2S)-2-dodecanoyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl] dodecanoate；[(2S)-2-dodecanoyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] dodecanoate
• 化学式: C₃₃H₆₂O₁₀
• 分子量: 618.849
• InChiKey: BIOJTMVLNXQLNJ-XLGOUSFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  43
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-O-(β-D-2',3',4',6'-tetra-O-acetyl-glucopyranosyl)-sn-glycerol 在 4-二甲氨基吡啶 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1,2-O-dilauroyl-3-O-β-D-glucopyranosyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides

  摘要：

  Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types I and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5 +/- 0.5 and 18.5 +/- 1.5 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2003.09.008

文献信息

• Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: total synthesis and structure activity relationships
  作者：Mark B. Richardson、Shota Torigoe、Sho Yamasaki、Spencer J. Williams

  DOI：10.1039/c5cc04773k

  日期：——

  Gentiobiosyl diglycerides fromMycobacterium tuberculosisare shown to signal through Mincle; structure–activity relationships reveal analogues with enhanced potency.

  结核分枝杆菌中的甘露二糖基二甘油酸被证明通过Mincle信号传导；结构-活性关系揭示出具有增强效力的类似物。
• Synthesis of dihydrosterculic acid-based monoglucosyl diacylglycerol and its analogues and their biological evaluation
  作者：Vudhgiri Srikanth、R.B.N. Prasad、Y. Poornachandra、V.S. Phani Babu、C. Ganesh Kumar、B. Jagadeesh、Ram Chandra Reddy Jala

  DOI：10.1016/j.ejmech.2015.12.048

  日期：2016.2

  methodology. The β-configuration of the GL1 molecule was unambiguously assigned by NMR studies using 2D-ROESY (NOE) and J-coupling analysis. Dihydrosterculic acid was synthesized using Furukawa's reagent and the selective esterification of dihydrosterculic acid at C-3 position of glycerol was achieved with EDC-HCl at 0 °C. In vitro cytotoxicity of the GL1 molecule and its fatty acid analogues was

  在本研究中，使用三氯乙亚氨酸酯方法合成了β-构型的植物乳杆菌糖脂（GL1）分子及其脂肪酸类似物。使用2D-ROESY（NOE）和J耦合分析的NMR研究明确确定了GL1分子的β-构型。使用Furukawa试剂合成二氢硬脂酸，并在0°C下用EDC-HCl实现甘油在C-3位置的二氢硬脂酸的选择性酯化。评估了GL1分子及其脂肪酸类似物对DU145，A549，SKOV3和MCF7细胞系的体外细胞毒性。在所有合成的分子中，GL1分子和化合物7d表现出中等活性，而该化合物图7b显示了针对所有测试的细胞系的有希望的活性，其IC 50值分别为20.1、18.2、19.1和17.6μM。此外，所有测试的化合物对正常的HUVEC细胞均显示出较弱的细胞毒性。与未处理的细胞相比，当用化合物7b处理时，MCF7细胞显示出较低的溴脱氧尿苷掺入水平，表明化合物7b是高度有效的并且抑制了细胞增殖。此外，这些化合物通过诱导MCF
• Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides
  作者：Wicharn Janwitayanuchit、Khanit Suwanborirux、Chamnan Patarapanich、Sunibhond Pummangura、Vimolmas Lipipun、Tirayut Vilaivan

  DOI：10.1016/j.phytochem.2003.09.008

  日期：2003.12

  Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types I and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5 +/- 0.5 and 18.5 +/- 1.5 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.