hippolide C | 1309104-56-0

• 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: hippolide C
• 英文别名: 3-[(1R,3E,7E,11E)-1-hydroxy-4-(hydroxymethyl)-8,12,16-trimethylheptadeca-3,7,11,15-tetraenyl]-2H-furan-5-one
• CAS: 1309104-56-0
• 化学式: C₂₅H₃₈O₄
• 分子量: 402.574
• InChiKey: VILQISSGAQMQCL-QAXNIAIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hippolide C 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 生成 [(2E,5E,9E)-6,10,14-trimethyl-2-[(3R)-3-(5-oxo-2H-furan-3-yl)-3-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxypropylidene]pentadeca-5,9,13-trienyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Hippolides A–H, Acyclic Manoalide Derivatives from the Marine Sponge Hippospongia lachne

  摘要：

  Eight new acyclic manoalide-related sesterterpenes, hippolides A H (1-8), together with two known manoalide derivatives, (6E)-neomanoalide (9) and (6Z)-neomanoalide (10), were isolated from the South China Sea sponge Hippospongia lachne. The absolute configurations of 1-8 were established by the modified Mosher's method and CD data. Compound 1 exhibited cytotoxicity against A549, HeLa, and HCT-116 cell lines with IC50 values of 5.22 x 10(-2), 4.80 x 10(-2), and 9.78 mu M, respectively. Compound 1 also showed moderate PTP1B inhibitory activitiy with an IC50 value of 23.81 mu M, and compound 2 showed moderate cytotoxicity against the HCT-116 cell line and PTP1B inhibitory activity with IC50 values of 35.13 and 39.67 yM, respectively. In addition, compounds 1 and 5 showed weak anti-inflammatory activity, with IC50 values of 61.97 and 40.35 mu M for PKC gamma and PKC alpha, respectively.

  DOI：

  10.1021/np200227s