fuscoside B | 133470-56-1

• 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: fuscoside B
• 英文别名: (2S,3S,4R,5R)-2-[(3E,5E)-6-[(3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-2-methylhepta-3,5-dien-2-yl]oxyoxane-3,4,5-triol
• CAS: 133470-56-1
• 化学式: C₂₅H₄₀O₅
• 分子量: 420.59
• InChiKey: NUXJYWUAZCOBLA-ZRCBPJAQSA-N

物化性质

• 沸点：
  541.5±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 fuscoside B 在 吡啶 作用下， 反应 3.0h， 以100%的产率得到Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-[(2E,4E)-5-((3R,4R)-3-isopropenyl-4-methyl-4-vinyl-cyclohexyl)-1,1-dimethyl-hexa-2,4-dienyloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Fuscosides A-D: anti-inflammatory diterpenoid glycosides of new structural classes from the caribbean gorgonian Eunicea fusca

  摘要：

  Four new diterpenoid arabinose glycosides, fuscosides A-D (1,3,5, and 6), have been isolated from the Caribbean gorgonian Eunicea fusca Duchassaing and Michelotti. Fuscoside A (1) is a diterpenoid 2'-O-acetylarabinose glycoside possessing a new bicyclic carbon skeleton related in biosynthetic origin to the eremophilane class of sesquiterpenoids. The structures of these new compounds were assigned on the basis of chemical and spectral studies. Fuscosides A and B (1, 3) are effective topical antiinflammatory agents with potencies equivalent to indomethacin and manoalide. Fuscoside B (3) selectively inhibits the synthesis of leukotrienes LTB4 and LTC4, but not PGE2, in the mouse peritoneal macrophage, suggesting it is a selective inhibitor of leukotriene synthesis.

  DOI：

  10.1021/jo00009a042

文献信息

• Fuscosides A-D: anti-inflammatory diterpenoid glycosides of new structural classes from the caribbean gorgonian Eunicea fusca
  作者：Jongheon Shin、William Fenical

  DOI：10.1021/jo00009a042

  日期：1991.4

  Four new diterpenoid arabinose glycosides, fuscosides A-D (1,3,5, and 6), have been isolated from the Caribbean gorgonian Eunicea fusca Duchassaing and Michelotti. Fuscoside A (1) is a diterpenoid 2'-O-acetylarabinose glycoside possessing a new bicyclic carbon skeleton related in biosynthetic origin to the eremophilane class of sesquiterpenoids. The structures of these new compounds were assigned on the basis of chemical and spectral studies. Fuscosides A and B (1, 3) are effective topical antiinflammatory agents with potencies equivalent to indomethacin and manoalide. Fuscoside B (3) selectively inhibits the synthesis of leukotrienes LTB4 and LTC4, but not PGE2, in the mouse peritoneal macrophage, suggesting it is a selective inhibitor of leukotriene synthesis.