C-17 lactam-bearing limonoids from the twigs and leaves of Amoora tsangii

J Nat Prod. 2014 Apr 25;77(4):983-9. doi: 10.1021/np401089h. Epub 2014 Mar 12.

Abstract

Twelve new lactam-bearing limonoids, amooramides A-L (1-12), were isolated from the twigs and leaves of Amoora tsangii, and their structures fully elucidated by spectroscopic analysis. These compounds represent the first examples of rings A,B-seco-limonoids bearing unusual lactam side chains at C-17, including a 3-substituted 1,5-dihydro-2H-pyrrol-2-one moiety in 1-7 and a 4-substituted 1,5-dihydro-2H-pyrrol-2-one unit in 8-12. Compound 9 inhibited TNFα-induced NF-κB activity by 64% at a concentration of 10 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Hep G2 Cells
  • Humans
  • Lactams / chemistry
  • Lactams / isolation & purification*
  • Lactams / pharmacology
  • Limonins / chemistry*
  • Limonins / isolation & purification*
  • Limonins / pharmacology
  • Meliaceae / chemistry*
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Drugs, Chinese Herbal
  • Lactams
  • Limonins
  • NF-kappa B
  • Tumor Necrosis Factor-alpha