Kandenol A | 1415238-86-6

• 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: Kandenol A
• 英文别名: (4aR,6R,7R,8aS)-7-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-1,4a,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 1415238-86-6
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: MEPRCLDIBSGQBP-KYEXWDHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Kandenol A 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 12.0h， 以0.3 mg的产率得到[(2R,3R,4aR,8aS)-3-(2-hydroxypropan-2-yl)-5,8a-dimethyl-7-oxo-1,2,3,4,4a,8-hexahydronaphthalen-2-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Kandenols A–E, Eudesmenes from an Endophytic Streptomyces sp. of the Mangrove Tree Kandelia candel

  摘要：

  Five novel eudesmene-type sesquiterpenes, kandenols A-E (1-5), have been isolated from Streptomyces sp. HKI0595 derived from the mangrove plant Kandelia candel. Their structures were established through NMR and mass spectrometry, and absolute configurations were established by the Mosher method and comparison of CD spectra with alpha-rotunol and beta-rotunol. The kandenols are reminiscent of various plant-derived eudesmenes, yet kandenols B and C are unusual because of their hydroperoxide moieties. Kandenol E is the first bacterial agarofuran, which belongs to an important group of antibiotics. Whereas the kandenols display no cytotoxicity against 12 human cell lines, weak to moderate antimicrobial activities were detected against Bacillus subtilis ATCC 6633 and Mycobacterium vaccae IMET 10670.

  DOI：

  10.1021/np300387n