<p>Three new pyridone alkaloids, tolypyrone A (<b>1</b>), tolypyrosides A (<b>2</b>) and B (<b>3</b>), and a new tetramic acid 2<i>′</i>-epitolypoalbin (<b>4</b>), along with ten known compounds, were obtained from <i>Tolypocladium</i> sp. CPCC 401485 isolated from an unidentified Antarctic lichen specimen. Structural elucidation of new compounds was achieved by analyses of HRESIMS and NMR spectroscopic data combined with X-ray crystallography, advanced Marfey’s method, and ECD calculation. Tolypyrone A (<b>1</b>) was the first 4-pyridone alkaloid with an unusual octahydro-1<i>H</i>-isochromeno[3,4-<i>b</i>]pyridin-4-one triheterocyclic ring system. Compounds <b>1</b>, <b>4</b> and <b>6</b> exhibited antimicrobial activities with the minimum inhibition concentration of 16−64&#xa0;μg/mL.</p> Graphical Abstract <p></p>

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Pyridone alkaloids from an Antarctic endolichenic Tolypocladium sp.

  • Shasha Li,
  • Ting Yu,
  • Jianju Feng,
  • Yue Shang,
  • Tao Zhang,
  • Shuzhen Chen,
  • Liyan Yu,
  • Maoluo Gan

摘要

Three new pyridone alkaloids, tolypyrone A (1), tolypyrosides A (2) and B (3), and a new tetramic acid 2-epitolypoalbin (4), along with ten known compounds, were obtained from Tolypocladium sp. CPCC 401485 isolated from an unidentified Antarctic lichen specimen. Structural elucidation of new compounds was achieved by analyses of HRESIMS and NMR spectroscopic data combined with X-ray crystallography, advanced Marfey’s method, and ECD calculation. Tolypyrone A (1) was the first 4-pyridone alkaloid with an unusual octahydro-1H-isochromeno[3,4-b]pyridin-4-one triheterocyclic ring system. Compounds 1, 4 and 6 exhibited antimicrobial activities with the minimum inhibition concentration of 16−64 μg/mL.

Graphical Abstract