6-O-palmitoyl-agnuside | 1105707-87-6

• 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: 6-O-palmitoyl-agnuside
• CAS: 1105707-87-6
• 化学式: C₃₈H₅₆O₁₂
• 分子量: 704.855
• InChiKey: NHSNRFKACVMVEU-LVJOBHEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  50.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  181.44
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  棕榈酸对硝基苯酯 、 牡荆油 在 Candida antarctica lipase B 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 以38%的产率得到6-O-palmitoyl-agnuside
  参考文献：
  名称：

  Synthesis of novel lipidated iridoid glycosides as vaccine adjuvants: 6-O-Palmitoyl Agnuside elicit strong Th1 and Th2 response to ovalbumin in mice

  摘要：

  Novel lipidated analogs of iridoids viz., Agnuside and Negundoside with different chain length were synthesized and tested for immune adjuvant activity in the presence of weak antigen ovalbumin. Based on in vitro assay, 6-O-palmitoyl Agnuside (AG-3) was further taken up for detailed in vivo activity and found to significantly enhance the production of anti OVA IgG titer, neutralizing antibody (IgG1 and IgG2a) titer as well as soluble mediators of a Th1 (IL-2, IFN-gamma)/Th2 response (IL-4) and proliferation of T lymphocyte subsets (CD4/CD8) and co stimulatory molecules CD80/CD86. Furthermore, the SAR studies revealed that presence of acyl group at aglycon moiety of these iridoid glycosides is crucial for immune adjuvant activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.intimp.2013.07.018