Limonoids from the leaves and stems of Toona ciliata

J Nat Prod. 2007 Aug;70(8):1268-73. doi: 10.1021/np070146c. Epub 2007 Jul 12.

Abstract

Three new norlimonoids, toonaciliatins A (1), F (6), and G (7), four new limonoids, toonaciliatins B-E (2-5), and five known compounds, 5alpha,6beta,8alpha-trihydroxy-28-norisotoonafolin (8), toonaciliatins H (9) and I (10), febrifugin (11), and khayasin T (12), were isolated from the leaves and stems of Toona ciliata. Compounds 1-3 have an unusual 1-en-3-one system with a 1,11-oxygen bridge, limonoids 11 and 12 have a mexicanolide-type structural frame, and others are typical A,B-seco- (4, 5, 9, and 10) or B-seco-29-nor- (3, 6, 7, and 8) limonoids. Toonaciliatins H (9) and I (10) were obtained for the first time as natural products. The structures were established by extensive spectroscopic methods, particularly 1D and 2D NMR techniques.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Limonins / chemistry
  • Limonins / isolation & purification*
  • Meliaceae / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plant Stems / chemistry

Substances

  • Drugs, Chinese Herbal
  • Limonins
  • toonaciliatin A
  • toonaciliatin F
  • toonaciliatin G