Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

Mar Drugs. 2019 Jul 3;17(7):394. doi: 10.3390/md17070394.

Abstract

Four phenylfuropyridone racemates, (±)-tersones A-C and E (1-3, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs 8 and 9 were isolated from the deep-sea fungus Phomopsis tersa. Their structures and absolute configurations were characterized on the basis of comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Moreover, compounds 1-9 were evaluated for in vitro antimicrobial and cytotoxic activity. Compounds 5b and 8b exhibited antibacterial activity against S. aureus with the MIC value of 31.5 μg/mL, while compound 5b showed cytoxic activities against SF-268, MCF-7, HepG-2 and A549 cell lines with IC50 values of 32.0, 29.5, 39.5 and 33.2 μM, respectively.

Keywords: Phomopsis tersa; antibacterial activity; cytotoxic activity; diastereoisomers; pyridone alkaloids.

MeSH terms

  • A549 Cells
  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Aquatic Organisms / chemistry*
  • Cell Line, Tumor
  • Fungi / chemistry*
  • Hep G2 Cells
  • Humans
  • MCF-7 Cells
  • Microbial Sensitivity Tests / methods
  • Pyridones / chemistry*
  • Pyridones / pharmacology
  • Staphylococcus aureus / drug effects

Substances

  • Alkaloids
  • Anti-Infective Agents
  • Pyridones