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Epipolythiodiketopiperazine and trichothecene derivatives from the NaI-containing fermentation of marine-derived

Hiroyuki Yamazaki1, Ohgi Takahashi2, Ryota Kirikoshi2

  • 1Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai, 981-8558, Japan. yamazaki@tohoku-mpu.ac.jp.

The Journal of Antibiotics
|May 20, 2020
PubMed

Insights

Marine fungus Trichoderma sp. TPU199 yields novel epipolythiodiketopiperazine derivatives and trichothecene sesquiterpenes. These compounds expand the known chemical diversity of fungal secondary metabolites, particularly those with unique disulfide bridge structures.

Area of Science:

  • Natural Product Chemistry
  • Mycology
  • Organic Chemistry

Background:

  • Marine-derived fungi are a rich source of structurally unique secondary metabolites.
  • The fungus Trichoderma sp. TPU199 is known to produce epipolythiodiketopiperazines (ETPs) with disulfide bridges.
  • Previous work identified halogenated ETPs from this strain under sodium halide fermentation.

Purpose of the Study:

  • To isolate and characterize new metabolites from Trichoderma sp. TPU199.
  • To investigate the chemical diversity of ETPs and sesquiterpenes produced by this fungus.
  • To elucidate the structures and absolute configurations of novel compounds.

Main Methods:

  • Fermentation of Trichoderma sp. TPU199 in the presence of sodium iodide.
  • Isolation and purification of secondary metabolites using chromatographic techniques.
  • Structure elucidation using extensive spectroscopic data (NMR, ECD) and comparison with known compounds.

Main Results:

  • Isolation of two new ETP derivatives (11 and 12) and three new trichothecene sesquiterpenes (13-15).
  • Compound 11 is a C-5 epimer of pretrichodermamide A (1).
  • Compound 12 is a trithio-derivative of 11.
  • Structures and absolute configurations of compounds 11-15 were determined.

Conclusions:

  • The study expands the known structural diversity of fungal ETPs and trichothecenes.
  • Fermentation with sodium iodide induces the production of novel sulfur-containing ETPs.
  • The findings highlight the potential of marine-derived fungi as sources of bioactive natural products.

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