(+)-(2S,3R,1'S,6'R)-5,7-dihydroxy-3,6'-epoxy-1',2',3',4',5',6'-tetrahydro-3',4'-secoflava-4',1'-lactone-3'-oic acid | 1196997-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (+)-(2S,3R,1'S,6'R)-5,7-dihydroxy-3,6'-epoxy-1',2',3',4',5',6'-tetrahydro-3',4'-secoflava-4',1'-lactone-3'-oic acid
• 英文别名: 2-[(1R,10S,11S,15R)-4,6-dihydroxy-13-oxo-9,12,16-trioxatetracyclo[8.6.0.03,8.011,15]hexadeca-3,5,7-trien-11-yl]acetic acid
• CAS: 1196997-46-2
• 化学式: C₁₅H₁₄O₈
• 分子量: 322.271
• InChiKey: XYTOQCRKUMAHBC-FIXIBIHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+)-(2S,3R,1'S,6'R)-5,7-dihydroxy-3,6'-epoxy-1',2',3',4',5',6'-tetrahydro-3',4'-secoflava-4',1'-lactone-3'-oic acid 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以0.8 mg的产率得到(+)-(2S,3R,1'S,6'R)-5,7-dihydroxy-3,6'-epoxy-1',2',3',4',5',6'-tetrahydro-3',4'-secoflava-4',1'-lactone-3'-oic acid methyl ester
  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