salpichrolide B

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: salpichrolide B
• 英文别名: (1S,2S,3S,7R,9S,11R)-15-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-2-methyl-8-oxapentacyclo[9.8.0.02,7.07,9.012,17]nonadeca-4,12(17),13,15-tetraen-3-ol
• 化学式: C₂₈H₃₆O₅
• 分子量: 452.591
• InChiKey: AZHXVDZYIMFQPH-OCAGBKIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 以80.5 mg的产率得到salpichrolide B
  参考文献：
  名称：

  Lethal and Sublethal Effects of Withanolides from Salpichroa origanifolia and Analogues on Ceratitis capitata

  摘要：

  Biological effects on Ceratitis capitata were evaluated for several withanolides isolated from Salpichroa origanifolia (Solanaceae), (20S,22R,24S,25S,26R)-5alpha,6alpha:22,26:24,25-triepoxy-26-hydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1 -one (salpichrolide A, 1), (20S,22R,24S,25S,26R)-22,26:24,25-diepoxy-5alpha,6beta,26-trihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide C, 2), (20S,22R,24S,25S,26R)-5alpha,6alpha;22,26:24,25-triepoxy-15,26-dihydroxy-17(13-->18)abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide G, 3), and (20S,22R,24S,25S,26R)-5alpha,6alpha:22,26:24,25-triepoxy-1,26-dihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraene (salpichrolide B, 5), and for chemically modified analogues. Influence of chemical modifications on development delay was analyzed. The compounds were incorporated into the larval diet and the adults' drinking water. Significant development delays from larvae to puparia were observed in treatments with the natural withanolides salpichrolides A, C, and G (1-3) at a concentration of 500 ppm. Salpichrolide B (5) was the most toxic compound, the highest mortality (95%) being observed at the larval stage. Exposure of adults to drinking water containing natural withanolides 1-3 and 5 produced mortality in all cases.

  DOI：

  10.1021/jf035508a