Nitric Oxide Inhibitory Activity and Absolute Configurations of Arylalkenyl α,β-Unsaturated δ/γ-Lactones from Cryptocarya concinna

J Nat Prod. 2016 Jan 22;79(1):196-203. doi: 10.1021/acs.jnatprod.5b00839. Epub 2016 Jan 7.

Abstract

During an ongoing exploration of potential anti-inflammatory agents from medicinal plants, eight new arylalkenyl α,β-unsaturated δ-lactones, cryptoconcatones A-H (1-8), and two unusual arylalkenyl α,β-unsaturated γ-lactones, cryptoconcatones I and J (9 and 10), were identified from the leaves and twigs of Cryptocarya concinna. The structures of these compounds were established based on spectroscopic data (MS, 1D/2D NMR), and their absolute configurations were determined with Riguera's method, the modified Mosher's method, chemical derivatization, and the Snatzke chirality rule. Compounds 4-6 and 8-10 showed inhibitory activity toward nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages, particularly compounds 4 and 8-10, with IC50 values of 3.2, 4.2, 3.4, and 7.5 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology*
  • Cryptocarya / chemistry*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology*
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Components, Aerial / chemistry
  • Stereoisomerism

Substances

  • Anti-Inflammatory Agents
  • Drugs, Chinese Herbal
  • Lactones
  • Lipopolysaccharides
  • Nitric Oxide