(-)-(2Z,3R,4S)-2-(dodec-11-ynylidene)-3-hydroxy-4-methylbutanolide | 1196997-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (-)-(2Z,3R,4S)-2-(dodec-11-ynylidene)-3-hydroxy-4-methylbutanolide
• 英文别名: (-)-(2Z,3S,4S)-2-(dodec-11-ynylidene)-3-hydroxy-4-methylbutanolide；Lincomolide B；(3Z,4S,5S)-3-dodec-11-ynylidene-4-hydroxy-5-methyloxolan-2-one
• CAS: 1196997-40-6
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: ZOHSBTYPSYCTIC-CHQMYWLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(2Z,3R,4S)-2-(dodec-11-ynylidene)-3-hydroxy-4-methylbutanolide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成
  参考文献：
  名称：

  Chemical Constituents of the Bark of Machilus wangchiana and Their Biological Activities

  摘要：

  Eleven new metabolites, butanolides 1-6, lignan derivatives 7-9, sesquiterpene 10, and 3',4'-seco-flavane derivative 11, have been isolated from an ethanol extract of Machilus wangchiana. Twenty known compounds, including ginkgolides A and B (16 and 17), were also isolated. Their structures and absolute configurations were determined by spectroscopic and chemical methods. Compounds 7, 8a, 8b, 9, 11, (+)-guaiacin (12), meso-dihydroguaiaretic acid (13), and hamabiwalactone A (15) showed potent in vitro activities against the release of beta-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF), with 42.5-75.6% inhibition at 10(-5) M. Compounds 8, 8a, 8b, 9, and 11 reduced DL-galactosamine (GaIN)-induced hepatocyte (WB-F344 cells) damage with 39.4 +/- 6.3% to 53.6 +/- 3.5% inhibition at 10(-4) M. Isomahubannolide-23 (14) was cytotoxic against human stomach cancer (BGC-823) and ovarian cancer (A2780) cell lines, with IC50 values of 0.13 and 2.66 mu M, respectively.

  DOI：

  10.1021/np900504a

文献信息

• Chemical Constituents of the Bark of <i>Machilus wangchiana</i> and Their Biological Activities
  作者：Wei Cheng、Chenggen Zhu、Wendong Xu、Xiaona Fan、Yongchun Yang、Yan Li、Xiaoguang Chen、Wenjie Wang、Jiangong Shi

  DOI：10.1021/np900504a

  日期：2009.12.28

  Eleven new metabolites, butanolides 1-6, lignan derivatives 7-9, sesquiterpene 10, and 3',4'-seco-flavane derivative 11, have been isolated from an ethanol extract of Machilus wangchiana. Twenty known compounds, including ginkgolides A and B (16 and 17), were also isolated. Their structures and absolute configurations were determined by spectroscopic and chemical methods. Compounds 7, 8a, 8b, 9, 11, (+)-guaiacin (12), meso-dihydroguaiaretic acid (13), and hamabiwalactone A (15) showed potent in vitro activities against the release of beta-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF), with 42.5-75.6% inhibition at 10(-5) M. Compounds 8, 8a, 8b, 9, and 11 reduced DL-galactosamine (GaIN)-induced hepatocyte (WB-F344 cells) damage with 39.4 +/- 6.3% to 53.6 +/- 3.5% inhibition at 10(-4) M. Isomahubannolide-23 (14) was cytotoxic against human stomach cancer (BGC-823) and ovarian cancer (A2780) cell lines, with IC50 values of 0.13 and 2.66 mu M, respectively.