Cipadonoid A, a novel limonoid with an unprecedented skeleton, from Cipadessa cinerasecns

Org Lett. 2008 May 15;10(10):1905-8. doi: 10.1021/ol800415n. Epub 2008 Apr 23.

Abstract

Cipadonoid A ( 1), a novel limonoid with an unprecedented skeleton, was isolated from the leaves of Cipadessa cinerasecns. Its structure and relative configuration were determined by spectroscopic analysis and computer modeling. 1 represents a new type of limonoid, characterized by a rearranged tetrahydropyranyl ring B incorporating usually exocyclic C-30. A possible biosynthetic pathway of 1 was also proposed.

MeSH terms

  • Circular Dichroism / methods
  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / isolation & purification
  • Limonins / chemistry*
  • Limonins / isolation & purification
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Meliaceae / chemistry*
  • Models, Chemical
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Reference Standards
  • Spectrophotometry, Ultraviolet / methods

Substances

  • Drugs, Chinese Herbal
  • Limonins
  • cipadonoid A