Bioactive constituents from Chinese natural medicines. XI. inhibitors on NO production and degranulation in RBL-2H3 from Rubia yunnanensis: structures of rubianosides II, III, and IV, rubianol-g, and rubianthraquinone

Chem Pharm Bull (Tokyo). 2003 Jun;51(6):654-62. doi: 10.1248/cpb.51.654.

Abstract

Three new arborinane-type triterpene glycosides, rubianosides II, III, and IV, a new arborinane-type triterpene, rubianol-g, and a new anthraquinone, rubianthraquinone, were isolated from a Chinese natural medicine, the roots of Rubia yunnanensis. The structures of the new constituents including their absolute configurations were determined on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined. Among them, a cyclic peptide constituent, RA-XII and its aglycon, RA-V (deoxybouvadin), potently inhibited overproduction of nitric oxide and induction of inducible nitric oxide synthase. In addition, an anthraquinone constituent, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone, was found to show inhibitory effects on the release of beta-hexosaminidase in RBL-2H3 cells.

MeSH terms

  • Animals
  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology
  • Cell Degranulation / drug effects*
  • Cell Line, Tumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages, Peritoneal / drug effects
  • Macrophages, Peritoneal / metabolism
  • Magnetic Resonance Spectroscopy
  • Mast Cells / drug effects
  • Mast Cells / metabolism
  • Mast Cells / physiology
  • Medicine, Chinese Traditional*
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis*
  • Nitric Oxide Synthase / antagonists & inhibitors
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology
  • Plant Roots / chemistry
  • Rats
  • Rubia / chemistry*
  • Stereoisomerism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Anthraquinones
  • Drugs, Chinese Herbal
  • Glycosides
  • Lipopolysaccharides
  • Peptides, Cyclic
  • Triterpenes
  • rubianol-g
  • rubianoside II
  • rubianthraquinone
  • RA XII
  • Nitric Oxide
  • RA V
  • Nitric Oxide Synthase