(Z)-15,18-dihydroxy-ent-labda-8(17),12-dien-16-oic acid | 1612240-59-1

• 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: (Z)-15,18-dihydroxy-ent-labda-8(17),12-dien-16-oic acid
• 英文别名: turraeanin I
• CAS: 1612240-59-1
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: LECJRFLSSUEICO-STTSWCNRSA-N

反应信息

• 作为反应物：
  描述：

  (Z)-15,18-dihydroxy-ent-labda-8(17),12-dien-16-oic acid 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以98%的产率得到turraeanin I diacetate
  参考文献：
  名称：

  Isolation and characterization of six labdane diterpenes and one pregnane steroid of Turraeanthus africanus

  摘要：

  Six labdane diterpene derivatives, named turraeanins F-J (3-6, 8) and epi-turraeanin J (7), and a pregnane steroid derivative named turraeasterodionene (2), were isolated by preparative high performance liquid chromatography together with thirteen known compounds from the Cameroonian medicinal plant Turraeanthus africanus. Their structures were elucidated by means of nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry in conjunction with the published data for the analogs, as well as the fragmentation patterns of each compound. Most of the known compounds were obtained for the first time from this plant. The compounds (2-7) were tested for their antibacterial efficacies against both Gram-positive and Gram-negative bacteria, including some clinically-important Risk group 2 human pathogens. Compound 4 exhibited the most pronounced antibacterial effectiveness comparable to standard reference streptomycin, with more potency against Gram-positive than Gram-negative bacteria. By comparing compounds 3, 4 and 5, a tentative structure-activity relationship could be drawn; selected oxidations at C-16 and C-18 drastically reduced the antibacterial efficacy of the parent compound (4). These results revealed the potential of compound 4 as a suitable antibacterial lead compound that might be used for further development of other derivatives to increase the antimicrobial efficacy.

  DOI：

  10.1016/j.phytochem.2014.03.022