3-Desoxyanthocyanidins from Arrabidaea chica

Phytochemistry. 2001 Apr;56(8):831-5. doi: 10.1016/s0031-9422(01)00038-3.

Abstract

The new 3-desoxyanthocyanidins 6,7,3'-trihydroxy-5,4'-dimethoxy-flavylium and 6,7,3',4'-tetrahydroxy-5-methoxy-flavylium and the known 6,7-dihydroxy-5,4'-dimethoxy-flavylium (Carajurin) were isolated by bioguided fractionation from the leaves of Arrabidaea chica, with transcription factor NF-kappaB as target. The structure of Carajurone was revised to be 6,7,4'-trihydroxy-5-methoxy-flavylium. Additionally, the flavone acacetin was found. All structures were mainly established on the basis of MS- and NMR data (1H, 1H-1H COSY and partly 13C, GHMQCR and GHSQCR). Carajurin, which failed to give a positive result in the DPPH TLC assay completely inhibited NF-kappaB, but not NF-AT at a 500 microM concentration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Humans
  • Jurkat Cells / drug effects
  • Jurkat Cells / metabolism
  • Magnetic Resonance Spectroscopy
  • Magnoliopsida / chemistry*
  • NF-kappa B / metabolism
  • Xanthenes / chemistry
  • Xanthenes / isolation & purification*
  • Xanthenes / pharmacology

Substances

  • Anti-Inflammatory Agents
  • NF-kappa B
  • Xanthenes