Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum

Chem Pharm Bull (Tokyo). 2008 Nov;56(11):1628-31. doi: 10.1248/cpb.56.1628.

Abstract

The methanolic extract from the flowers of Punica granatum L. (Punicaceae) was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha, 1 ng/ml)-induced cytotoxicity in L929 cells. By bioassay-guided separation, a new taraxastane-type triterpene, punicanolic acid (1), was isolated from the active fraction (ethyl acetate-soluble fraction) together with four triterpenes (2--5), two galloyl glucoses (6, 7), two flavones (8, 9), and beta-sitosterol. Among the constituents, 1, oleanolic acid (2), maslinic acid (4), 1,2,6-tri-O-galloyl beta-D-glucopyranoside (6), 1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl beta-D-glucopyranoside (7), and luteolin (8) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Flowers / chemistry
  • Humans
  • Lythraceae / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Plant Extracts / pharmacology
  • Spectrophotometry, Ultraviolet
  • Tetrazolium Salts
  • Thiazoles
  • Triterpenes / chemical synthesis
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*

Substances

  • Plant Extracts
  • Tetrazolium Salts
  • Thiazoles
  • Triterpenes
  • Tumor Necrosis Factor-alpha
  • punicanolic acid
  • thiazolyl blue