Four di-O-caffeoyl quinic acid derivatives from propolis. Potent hepatoprotective activity in experimental liver injury models

Purusotam Basnet, Katsumichi Matsushige, Koji Hase, Shigetoshi Kadota, Tsuneo Namba

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The water extract of propolis (PWE) showed a strong hepatoprotective activity against CCl4-toxicity in rats and D-galactosamine (GaIN)/lipopolysaccharide (LPS)-induced liver injury in mice. The PWE also showed a significant hepatoprotective activity against CCl4-induced liver cell injury in cultured rat hepatocytes. The in vitro hepatoprotective activity guided fractionation and chemical analysis led to the isolation of four dicaffeoyl quinic acid derivatives from the PWE. The structure of these isolates was determined to be methyl 3,4-di-O-caffeoyl quinate (1), 3,4-di- O-caffeoyl quinic acid (2), methyl 4,5-di-O-caffeoyl quinate (3), and 3,5- di-O-caffeoyl quinic acid (4) by spectroscopic methods. These compounds were more potent hepatoprotective agents than glycyrrhizin at a concentration of 10 μg/ml and 1 was the most potent among the four compounds in the cultured hepatocytes. Quinic acid (5) alone did not show hepatoprotective effects in cultured rat hepatocytes against CCl'4-toxicity. On the other hand, chlorogenic acid (6) or caffeic acid alone was found to be less potent than the dicaffeoyl quinic acid derivatives.

Original languageEnglish
Pages (from-to)1479-1484
Number of pages6
JournalBiological and Pharmaceutical Bulletin
Issue number11
Publication statusPublished - 1996 Nov
Externally publishedYes



  • D-galactosamine-lipopolysaccharide
  • carbon tetrachloride
  • dicaffeoyl quinic acid
  • hepatoprotective effect
  • propolis

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

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