(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-18-((5E,9E)-(1S,2R,3S,7S,8R)-2,8-Dihydroxy-1,3,7-trimethyl-4-oxo-undeca-5,9-dienyl)-8,10-dihydroxy-3,17-dimethoxy-5,7,9,11,13-pentamethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-18-((5E,9E)-(1S,2R,3S,7S,8R)-2,8-Dihydroxy-1,3,7-trimethyl-4-oxo-undeca-5,9-dienyl)-8,10-dihydroxy-3,17-dimethoxy-5,7,9,11,13-pentamethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one
• 英文别名: (3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(2S,3R,4S,6E,8S,9R,10E)-3,9-dihydroxy-4,8-dimethyl-5-oxododeca-6,10-dien-2-yl]-8,10-dihydroxy-3,17-dimethoxy-5,7,9,11,13-pentamethyl-1-oxacyclooctadeca-3,5,13,15-tetraen-2-one
• 化学式: C₃₈H₆₀O₉
• 分子量: 660.889
• InChiKey: QPGTXBRGXJNRGI-JZCZIURLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  刀豆素B 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以46%的产率得到(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-18-((5E,9E)-(1S,2R,3S,7S,8R)-2,8-Dihydroxy-1,3,7-trimethyl-4-oxo-undeca-5,9-dienyl)-8,10-dihydroxy-3,17-dimethoxy-5,7,9,11,13-pentamethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one
  参考文献：
  名称：

  Concanamycin B Inhibits the Expression of Newly-synthesized MHC Class II Molecules on the Cell Surface.

  摘要：

  We screened natural chemical compounds which inhibit the expression of newly-synthesized MHC class II molecules on the cell surface. IFN-γ stimulates Colo 205 adenocarcinoma cells to induce the expression of MHC class I, MHC class II, and 1C AM-1 molecules on the cell surface. We show here that concanamycin B inhibits the expression of MHC class II molecules on Colo 205 cells, whereas it does not affect the expression of MHC class I and ICAM-1 molecules. Concanamycin B also abrogates the enhancement of the MHC class II expression by IL-4 on mouse lymphocytes. Furthermore, concanamycin B suppresses the antigen presentation by MHC class II molecules.

  DOI：

  10.7164/antibiotics.48.488

文献信息

• Concanamycin B Inhibits the Expression of Newly-synthesized MHC Class II Molecules on the Cell Surface.
  作者：KOUICHI ITO、TSUYOSHI KOBAYASHI、YOSHINORI MORIYAMA、KAZUNOBU TOSHIMA、KUNIAKI TATSUTA、TERUTAKA KAKIUCHI、MASAMITSU FUTAI、HIDDE L. PLOEGH、KIYOSHI MIWA

  DOI：10.7164/antibiotics.48.488

  日期：——

  We screened natural chemical compounds which inhibit the expression of newly-synthesized MHC class II molecules on the cell surface. IFN-γ stimulates Colo 205 adenocarcinoma cells to induce the expression of MHC class I, MHC class II, and 1C AM-1 molecules on the cell surface. We show here that concanamycin B inhibits the expression of MHC class II molecules on Colo 205 cells, whereas it does not affect the expression of MHC class I and ICAM-1 molecules. Concanamycin B also abrogates the enhancement of the MHC class II expression by IL-4 on mouse lymphocytes. Furthermore, concanamycin B suppresses the antigen presentation by MHC class II molecules.