Two new benzophenones and one new natural amide alkaloid isolated from a mangrove-derived Fungus Penicillium citrinum

Nat Prod Res. 2019 Apr;33(8):1127-1134. doi: 10.1080/14786419.2018.1460832. Epub 2018 Apr 15.

Abstract

Two new compounds penibenzophenones A-B (1-2), and the synthetic α,β-unsaturated amide alkaloid (E)-tert-butyl(3-cinnamamidopropyl)carbamate (4), newly identified as a natural product, alone with three known ones (3, 5-6) were isolated from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Compound 1 was a chlorinated benzophenone. The structures of 1-6 were elucidated by extensive NMR spectral interpretation, MS data and X-ray analysis. The new compound 2 displayed cytotoxic activity against human A549 cell lines with an IC50 value of 15.7 μg/mL, and 1 showed antibacterial activity against Staphylococcus aureus with a MIC value of 20 μg/mL.

Keywords: amide alkaloid; antibacterial activity; cytotoxic activity; penibenzophenone.

Publication types

  • Video-Audio Media

MeSH terms

  • A549 Cells
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Amides / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Benzophenones / isolation & purification
  • Benzophenones / pharmacology*
  • Crystallography, X-Ray
  • Drug Evaluation, Preclinical / methods
  • Endophytes / chemistry
  • Humans
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Penicillium / chemistry*
  • Rhizophoraceae / microbiology
  • Staphylococcus aureus / drug effects
  • Wetlands

Substances

  • Alkaloids
  • Amides
  • Anti-Bacterial Agents
  • Benzophenones