Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus

Molecules. 2019 Dec 23;25(1):61. doi: 10.3390/molecules25010061.

Abstract

Seven known echinulin-related indolediketopiperazine alkaloids (1-7) were isolated from the Vietnamese sediment-derived fungus Aspergillus niveoglaucus. Using chiral HPLC, the enantiomers of cryptoechinuline B (1) were isolated as individual compounds for the first time. (+)-Cryptoechinuline B (1a) exhibited neuroprotective activity in 6-OHDA-, paraquat-, and rotenone-induced in vitro models of Parkinson's disease. (-)-Cryptoechinuline B (1b) and neoechinulin C (5) protected the neuronal cells against paraquat-induced damage in a Parkinson's disease model. Neoechinulin B (4) exhibited cytoprotective activity in a rotenone-induced model, and neoechinulin (7) showed activity in the 6-OHDA-induced model.

Keywords: 6-OHDA; Aspergillus niveoglaucus; NMR data; cryptoechinuline; cytotoxic activity; echinulin; neoechinulin; neuroprotective activity; paraquat; rotenone; urease inhibition.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Aspergillus / chemistry*
  • Chromatography, High Pressure Liquid
  • Geologic Sediments / chemistry
  • Geologic Sediments / microbiology
  • Humans
  • Neurons / drug effects
  • Neurons / pathology
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / isolation & purification
  • Neuroprotective Agents / pharmacology*
  • Paraquat / toxicity
  • Parkinson Disease, Secondary / chemically induced
  • Parkinson Disease, Secondary / drug therapy
  • Piperazine / analogs & derivatives
  • Piperazine / chemistry
  • Piperazine / isolation & purification
  • Piperazine / pharmacology*

Substances

  • Alkaloids
  • Neuroprotective Agents
  • Piperazine
  • echinuline
  • Paraquat