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Cucurbitane triterpenoids from Leucopaxillus gentianeus.

Marco Clericuzio1, Mariella Mella, Paola Vita-Finzi

  • 1Dipartimento di Chimica Generale ed Organica Applicata, Università di Torino, Via P. Giuria 7, 10125 Torino, Italy. marco.clericuzio@unito.it

Journal of Natural Products
|December 1, 2004
PubMed
Summary

Two new cucurbitane triterpenoids, leucopaxillones A and B, were isolated from Leucopaxillus gentianeus. Cucurbitacin B demonstrated significant in vitro antitumor activity against human tumor cell lines.

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Area of Science:

  • Natural Product Chemistry
  • Mycology
  • Chemical Ecology

Background:

  • The mushroom Leucopaxillus gentianeus (syn. L. amarus) is a source of bioactive compounds.
  • Cucurbitacins are a class of triterpenoids known for their diverse biological activities.
  • Understanding the chemical defense mechanisms of fungi is crucial for ecological and pharmaceutical research.

Purpose of the Study:

  • To isolate and characterize new cucurbitane triterpenoids from Leucopaxillus gentianeus.
  • To evaluate the in vitro cytotoxic effects of isolated compounds against human tumor cell lines.
  • To investigate the ecological role and evolutionary significance of these compounds.

Main Methods:

  • Isolation and purification of compounds using chromatographic techniques.

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  • Structure elucidation by spectroscopic methods (NMR, MS) and X-ray diffraction.
  • In vitro cytotoxicity assay (MTT assay) against A549, CAKI-1, HepG2, and MCF-7 cell lines.

    • Main Results:

    • Isolation of cucurbitacin B (1) and two new cucurbitane triterpenoids, leucopaxillones A (3) and B (4), with a novel oxygenation pattern.
    • Cucurbitacin B (1) exhibited high in vitro activity against all tested human tumor cell lines.
    • Compounds 1-4 showed structural similarities to plant-derived cucurbitacins, suggesting convergent evolution.

    Conclusions:

    • Leucopaxillus gentianeus produces unique cucurbitane triterpenoids, including leucopaxillones A and B.
    • Cucurbitacin B acts as a potent cytotoxic agent, likely serving as a chemical defense mechanism for the mushroom.
    • The findings highlight secondary metabolite convergence between fungi and plants, with cucurbitacin B as a key example.