D-ring-opened phragmalin-type limonoids from Chukrasia tabularis var. velutina

Chem Biodivers. 2011 Dec;8(12):2261-9. doi: 10.1002/cbdv.201000285.

Abstract

Five new D-ring-opened phragmalin-type limonoids, tabulalins A-E (1-5, resp.), were isolated from the stem bark of Chukrasia tabularis var. velutina. In the structures of these new isolates, the D-ring (C(16)/C(17) δ-lactone ring) of phragmalins was cleaved, and rare C(16)/C(30) δ-lactone ring in 1-3 or C(16)/C(8) γ-lactone ring in 4 and 5 were formed. The structures of these new compounds were elucidated based on extensive 1D- and 2D-spectroscopic analyses (HSQC, HMBC, and ROESY) and HR-ESI-MS. The major compounds, 2, 3, and 5, were evaluated for their inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in a macrophage (RAW264.7) cell line with IC(50) values of 15.3±0.6, 13.0±0.5, and 17.1±0.7 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Anti-Inflammatory Agents, Non-Steroidal / toxicity
  • Cell Line
  • Cell Survival / drug effects
  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / isolation & purification*
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Limonins / chemistry*
  • Limonins / isolation & purification
  • Limonins / pharmacology
  • Limonins / toxicity
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Plant Bark / chemistry
  • Plant Stems / chemistry
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Drugs, Chinese Herbal
  • Lactones
  • Limonins
  • Nitric Oxide