Asperorydines N-P, three new cyclopiazonic acid alkaloids from the marine-derived fungus Aspergillus flavus SCSIO F025

Fitoterapia. 2021 Apr:150:104839. doi: 10.1016/j.fitote.2021.104839. Epub 2021 Jan 26.

Abstract

Three new tricyclic cyclopiazonic acid (CPA) related alkaloids asperorydines N-P (1-3), together with six known compounds (4-9) were isolated and characterized from the fungus Aspergillus flavus SCSIO F025 derived from the deep-sea sediments of South China Sea. The structures including absolute configurations of 1-3 were deduced from spectroscopic data, X-ray diffraction analysis, and electronic circular dichroism (ECD). All compounds were evaluated for the antioxidative activities against DPPH, cytotoxic activities against four tumor cell lines (SF-268, HepG-2, MCF-7, and A549), and antimicrobial activities. Compound 9 showed significant radical scavenging activities against DPPH with an IC50 value of 62.23 μM and broad-spectrum cytotoxicities against four tumor cell lines with IC50 values ranging from 24.38 to 48.28 μM. Furthermore, compounds 4-9 exhibited weak antimicrobial activities against E scherichia coli, and compound 9 also showed antibacterial activity against Bacillus thuringiensis, Micrococcus lutea, Staphylococcus aureus, Bacillus subtilis, Methicillin resistant Staphylococcus aureus.

Keywords: Antioxidative, cytotoxic, and antimicrobial activity; Aspergillus flavus; Cyclopiazonic acid; Deep-sea sediments.

MeSH terms

  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Aquatic Organisms / chemistry
  • Aspergillus flavus / chemistry*
  • Bacillus / drug effects
  • Cell Line, Tumor
  • China
  • Escherichia coli / drug effects
  • Geologic Sediments / microbiology
  • Humans
  • Indoles / isolation & purification
  • Indoles / pharmacology*
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Micrococcus / drug effects
  • Molecular Structure
  • Seawater / microbiology

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Indoles
  • cyclopiazonic acid