Antiallergic agents from natural sources. 3. Structures and inhibitory effects on nitric oxide production and histamine release of five novel polyacetylene glucosides from Bidens parviflora WILLD

Chem Pharm Bull (Tokyo). 2001 Aug;49(8):938-42. doi: 10.1248/cpb.49.938.

Abstract

Five new polyacetylene glucosides, bidensyneosides A1, A2, B, C (1-4), and 3-deoxybidensyneoside B (5), have been isolated from the air-dried whole plant of Bidens parviflora WILLD. The structures were identified based on spectroscopic analysis, physicochemical properties, and application of the modified Mosher method to be 3(R),8(E)-8-decene-4,6-diyne-1,3-diol 1-O-beta-D-glucopyranoside (1), deca-3(R),8(Z) 8-decene-4,6-diyne-1,3-diol 1-O-beta-D-glucopyranoside (2), 3(R)-deca-4,6,8-triyne-1,3-diol 1-O-beta-D-glucopyranoside (3), 3(R),8(E)-8-decene-4,6-diyne-1,3,10-triol 1-O-beta-D-glucopyranoside (4), and 8(E)-8-decene-4,6-diyne-1,10-diol 1-O-beta-D-glucopyranoside (5), respectively. These compounds inhibited nitric oxide (NO) production in lipopolysaccharide and interferon-gamma activated murine macrophages (RAW264.7) and also inhibited histamine release from rat mast cells stimulated by the antigen-antibody reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry
  • Acetylene / isolation & purification
  • Acetylene / pharmacology*
  • Animals
  • Anti-Allergic Agents / chemistry
  • Anti-Allergic Agents / isolation & purification
  • Anti-Allergic Agents / pharmacology*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification
  • Drugs, Chinese Herbal / pharmacology*
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glucosides / pharmacology*
  • Histamine Release / drug effects*
  • Histamine Release / physiology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Male
  • Mast Cells / drug effects
  • Mast Cells / metabolism
  • Medicine, Chinese Traditional
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Polymers / chemistry
  • Polymers / isolation & purification
  • Polymers / pharmacology*
  • Polyynes
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship

Substances

  • Anti-Allergic Agents
  • Drugs, Chinese Herbal
  • Glucosides
  • Polymers
  • Polyynes
  • Nitric Oxide
  • Acetylene