Antifungal chromans inhibiting the mitochondrial respiratory chain of pea seeds and new xanthones from Calophyllum caledonicum

Planta Med. 2003 Dec;69(12):1130-5. doi: 10.1055/s-2003-818004.

Abstract

Two new xanthones, caledonixanthone M 1 and caloxanthone L 2, and one new acid, caledonic acid 6 were isolated from the hexane-soluble extract of the stem bark of Calophyllum caledonicum. In the course of this phytochemical study, seven other known compounds - calothwaitesixanthone, calozeyloxanthone, allanxanthone, isoapetalic acid 3, calolongic acid 4, apetalic acid 5 and isocalolongic acid 7 - were isolated. Their antifungal activity against the growth of the human pathogenic fungus Aspergillus fumigatus was then investigated. The results indicated that the crude extract, calolongic acid 4 and isocalolongic acid 7 exhibited strong inhibitory effects with MIC (80) values of 8, 4, 2 microg/mL, respectively. Besides, calolongic acid 4, its lactone derivative 4a and isocalolongic acid 7 markedly reduced the respiration of pea seed mitochondria.

MeSH terms

  • Antifungal Agents / administration & dosage
  • Antifungal Agents / pharmacology*
  • Antifungal Agents / therapeutic use
  • Aspergillus fumigatus / drug effects
  • Calophyllum*
  • Chromans / administration & dosage
  • Chromans / pharmacology*
  • Chromans / therapeutic use
  • Electron Transport / drug effects*
  • Humans
  • Microbial Sensitivity Tests
  • Mitochondria / drug effects
  • Phytotherapy*
  • Pisum sativum / metabolism
  • Plant Bark
  • Plant Extracts / administration & dosage
  • Plant Extracts / pharmacology
  • Plant Extracts / therapeutic use
  • Seeds

Substances

  • Antifungal Agents
  • Chromans
  • Plant Extracts