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

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 IC 50 value of 62.23 μM and broad-spectrum cytotoxicities against four tumor cell lines with IC 50 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. [Display omitted] • Nine compounds were isolated from the deep-sea derived fungus Aspergillus flavus SCSIO F025. • Three new tricyclic cyclopiazonic acids (CPAs) with an open-ring indole are reported. • Their structures were determined by spectroscopic data, X-ray diffraction analysis, and electronic circular dichroism (ECD). • All the compounds were tested for their antioxidative activities , cytotoxic activities , and antimicrobial activities. [ABSTRACT FROM AUTHOR]