Absolute stereostructures of three new sesquiterpenes from the fruit of Alpinia oxyphylla with inhibitory effects on nitric oxide production and degranulation in RBL-2H3 cells

J Nat Prod. 2002 Oct;65(10):1468-74. doi: 10.1021/np020078o.

Abstract

The 80% aqueous acetone extract and the ethyl acetate-soluble portion from the dried fruit of Alpinia oxyphylla MIQUEL were found to show inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages and antigen-induced degranulation in RBL-2H3 cells. A new eudesmane-type sesquiterpene, oxyphyllol A, and two eremophilane-type sesquiterpenes, oxyphyllols B and C, were isolated from the ethyl acetate-soluble portion, together with 16 known constituents. The absolute stereostructures of oxyphyllols A, B, and C were determined on the basis of chemical and physicochemical evidence. The effects of isolated components on nitric oxide production were examined, and nine constituents including oxyphyllol A and nootkatone were found to show inhibitory activity. On the other hand, five constituents inhibited the release of beta-hexosaminidase from RBL-2H3 cells.

MeSH terms

  • Alpinia / chemistry*
  • Animals
  • Cell Degranulation / drug effects*
  • Cell Line
  • Male
  • Mice
  • Nitric Oxide / biosynthesis*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Spectrum Analysis
  • Stereoisomerism
  • beta-N-Acetylhexosaminidases / metabolism

Substances

  • Sesquiterpenes
  • Nitric Oxide
  • beta-N-Acetylhexosaminidases