D-ring-opened phragmalin-type limonoid orthoesters from the twigs of Swietenia macrophylla

J Nat Prod. 2009 Jul;72(7):1305-13. doi: 10.1021/np900139c.

Abstract

Sixteen new D-ring-opened phragmalin limonoid orthoesters, swietenitins A-M (1-6, 8, 10, 12-16), 2-acetoxyswietenialide D (7), 2,11-diacetoxyswietenialide D (9), and 11-deoxyswietenialide D (11), and four known compounds were isolated from the twigs of Swietenia macrophylla. The structures of 1-16 were established on the basis of spectroscopic methods, and 1 and 2 were confirmed by single-crystal X-ray diffraction. The (1)H NMR-based conformational analysis on the epimeric compounds 1 and 2 provided a general approach to determine the absolute configuration of the 2,3-epoxy-2-methylbutyryloxy unit at C-3 borne by a large group of the known phragmalin-type limonoid orthoesters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Limonins / chemistry
  • Limonins / isolation & purification*
  • Meliaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Stems / chemistry

Substances

  • Limonins