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Pretrichodermamides D-F from a Marine Algicolous Fungus Penicillium sp. KMM 4672

Anton N Yurchenko1, Olga F Smetanina2, Elena V Ivanets3

  • 1G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. yurchant@ya.ru.

Marine Drugs
|June 30, 2016
PubMed

Insights

Researchers discovered three new compounds, pretrichodermamides D-F, from a marine fungus. One compound, N-methylpretrichodermamide B, demonstrated potent cytotoxicity against drug-resistant prostate cancer cells.

Area of Science:

  • Natural Product Chemistry
  • Marine Microbiology
  • Pharmacology

Background:

  • Marine-derived fungi are a rich source of novel bioactive compounds.
  • Penicillium species are known producers of diverse secondary metabolites.
  • Epidithiodiketopiperazines represent a class of fungal compounds with potential therapeutic applications.

Purpose of the Study:

  • To isolate and characterize new epidithiodiketopiperazines from a marine fungus.
  • To investigate the cytotoxic activity of isolated compounds against cancer cell lines.

Main Methods:

  • Lipophilic extraction of fungal biomass.
  • Isolation and purification using chromatographic techniques.
  • Structure elucidation via comprehensive spectroscopic methods (NMR, MS).
  • Determination of absolute configuration using modified Mosher's method and NOESY data.

Main Results:

  • Three new epidithiodiketopiperazines, pretrichodermamides D-F (1-3), were identified.
  • Two known compounds, N-methylpretrichodermamide B (4) and pretrichodermamide C (5), were also isolated.
  • The absolute configuration of pretrichodermamide D (1) was successfully determined.
  • N-Methylpretrichodermamide B (5) exhibited significant cytotoxicity against 22Rv1 human prostate cancer cells, including those resistant to androgen receptor targeted therapies.

Conclusions:

  • The marine fungus Penicillium sp. KMM 4672 produces novel epidithiodiketopiperazines.
  • Pretrichodermamide D possesses a defined absolute configuration.
  • N-Methylpretrichodermamide B shows promise as a potential therapeutic agent for drug-resistant prostate cancer.
Keywords:
cytotoxicitydiketopiperazinemarine-derived fungusoxazadecalinesecondary metabolites

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