Structure of a Coumaric Acid Analogue with a Monoterpene Moiety from the Flowers of Osmanthusfragrans var. aurantiacus and Evaluation of Cinnamic Acid Analogues as Nitric Oxide Production and Degranulation Inhibitors

Nat Prod Commun. 2016 Aug;11(8):1123-1128.

Abstract

A coumaric acid analogue with a monoterpene moiety named floraosmanol A (1) was isolated from the flowers of Osmanthisfragrans var. aurantiacus. The chemical structure was elucidated on the basis of chemical and physicochemical evidence. Floraosmanol A (1) significantly inhibited nitric oxide .(NO) production in lipopolysaccharide- (LPS) activated RAW264.7 macrophages and the release of P-hexosaminidase as a marker of degranulation from rat basophile leukemia (RBL-2H3) cells. In addition, several cinnamic acid analogues were conjugated with geraniol and 3-methyl-2-buten-1-ol through an ester linkage. The inhibitory effects on NO production and the release of P-hexosaminidase of the synthesized compounds were examined for structure-activity relationships.

MeSH terms

  • Animals
  • Cinnamates / chemistry*
  • Coumaric Acids / chemistry*
  • Flowers / chemistry*
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Monoterpenes / chemistry*
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / metabolism*
  • Oleaceae / chemistry*
  • RAW 264.7 Cells

Substances

  • Cinnamates
  • Coumaric Acids
  • Lipopolysaccharides
  • Monoterpenes
  • cinnamic acid
  • Nitric Oxide