4-Phenyl-3,4-dihydroquinolone derivatives from Aspergillus nidulans MA-143, an endophytic fungus isolated from the mangrove plant Rhizophora stylosa

J Nat Prod. 2013 Oct 25;76(10):1896-901. doi: 10.1021/np4004646. Epub 2013 Oct 7.

Abstract

Six new 4-phenyl-3,4-dihydroquinolone derivatives (1-6) along with the related aflaquinolone A (7) were isolated and identified from the cultures of Aspergillus nidulans MA-143, an endophytic fungus obtained from the fresh leaves of the marine mangrove plant Rhizophora stylosa. Their structures including absolute configurations were determined by spectroscopic analysis and electronic circular dichroism experiments, and the structure of compound 1 was confirmed by single-crystal X-ray crystallographic analysis. In bioscreening experiments, none of the isolated compounds showed potent antibacterial or cytotoxic activity. However, compounds 2, 3, and 7 exhibited lethality against brine shrimp (Artemia salina), with LD50 values of 7.1, 4.5, and 5.5 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Artemia / drug effects
  • Aspergillus nidulans / chemistry*
  • Circular Dichroism
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Escherichia coli / drug effects
  • Female
  • HL-60 Cells
  • Humans
  • K562 Cells
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / microbiology
  • Quinolones / chemistry
  • Quinolones / isolation & purification*
  • Quinolones / pharmacology
  • Rhizophoraceae / microbiology*
  • Staphylococcus aureus / drug effects

Substances

  • Quinolones
  • aflaquinolone A