Isolation, synthesis, and bioactivity of homoisoflavonoids from Caesalpinia pulcherrima

Chem Pharm Bull (Tokyo). 2009 Oct;57(10):1139-41. doi: 10.1248/cpb.57.1139.


One new homoisoflavonoid, (3E)-2,3-dihydro-6,7-dimethoxy-3[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and four naturally new analogues, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-methoxy-4H-1-benzopyran-4-one, (3E)-2,3-dihydro-7-hydroxy-3-[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and (3E)-2,3-dihydro-3-[(3,4-dimethoxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one, along with four known homoisoflavonoids, bonducellin, sappanone A, 2'-methoxybonducellin and 7-O-methylbonducellin were isolated from aerial parts of Caesalpinia pulcherrima. The structures of the new compounds were elucidated by interpretation of their 1D and 2D NMR spectra. Syntheses of the naturally new compounds and the known compounds have also been accomplished. The antibacterial and antifungal activities of the isolated homoisoflavonoids were studied.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Caesalpinia / chemistry*
  • Isoflavones / chemical synthesis*
  • Isoflavones / isolation & purification
  • Isoflavones / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation


  • Anti-Bacterial Agents
  • Antifungal Agents
  • Isoflavones