Bioactive Polyketide and Diketopiperazine Derivatives from the Mangrove-Sediment-Derived Fungus Aspergillus sp. SCSIO41407

Molecules. 2021 Aug 11;26(16):4851. doi: 10.3390/molecules26164851.

Abstract

Ten polyketide derivatives (1-10), including a new natural product named (E)-2,4-dihydroxy-3-methyl-6-(2-oxopent-3-en-1-yl) benzaldehyde (1), and five known diketopiperazines (11-15), were isolated from the mangrove-sediment-derived fungus Aspergillus sp. SCSIO41407. The structures of 1-15 were determined via NMR and MS spectroscopic analysis. In a variety of bioactivity screening, 3 showed weak cytotoxicity against the A549 cell line, and 2 exhibited weak antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Compounds 3, 5, and 6 showed inhibition against acetylcholinesterase (AChE) with IC50 values of 23.9, 39.9, and 18.6 μM. Compounds 11, 12, and 14 exhibited obvious inhibitory activities of lipopolysaccharide (LPS)-induced nuclear factor-κB (NF-κB) with IC50 values of 19.2, 20.9, and 8.7 μM, and they also suppressed RANKL-induced osteoclast differentiation in bone marrow macrophages cells (BMMCs), with the concentration of 5 μM. In silico molecular docking with AChE and NF-κB p65 protein were also performed to understand the inhibitory activities, and 1, 11-14 showed obvious protein/ligand-binding effects to the NF-κB p65 protein.

Keywords: Aspergillus; NF-κB; acetylcholinesterase; diketopiperazines; mangrove-sediment-derived fungus; polyketides.

MeSH terms

  • A549 Cells
  • Acetylcholinesterase / metabolism
  • Aspergillus / drug effects*
  • Cell Death / drug effects
  • Cell Differentiation / drug effects
  • Cholinesterase Inhibitors / pharmacology
  • Diketopiperazines / chemistry
  • Diketopiperazines / pharmacology*
  • Geologic Sediments / microbiology*
  • Humans
  • Lipopolysaccharides / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • NF-kappa B / metabolism
  • Osteoclasts / cytology
  • Osteoclasts / drug effects
  • Polyketides / chemistry
  • Polyketides / pharmacology*
  • Proton Magnetic Resonance Spectroscopy
  • RANK Ligand / pharmacology
  • Rhizophoraceae / chemistry*

Substances

  • Cholinesterase Inhibitors
  • Diketopiperazines
  • Lipopolysaccharides
  • NF-kappa B
  • Polyketides
  • RANK Ligand
  • Acetylcholinesterase