A new cyclic hexapeptide and a new isocoumarin derivative from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013

• Published in: Marine drugs Vol. 13; no. 3; pp. 1432 - 1450
• Main Authors: Prompanya, Chadaporn, Fernandes, Carla, Cravo, Sara, Pinto, Madalena M M, Dethoup, Tida, Silva, Artur M S, Kijjoa, Anake
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01-03-2015; MDPI
• Subjects: Animals; Aspergillus; Aspergillus - isolation & purification; Aspergillus - metabolism; Aspergillus similanensis; Bacteria - drug effects; Cell Line, Tumor; Chromatography, High Pressure Liquid; cyclic hexapeptide; Humans; isocoumarin; Isocoumarins - chemistry; Isocoumarins - isolation & purification; Isocoumarins - pharmacology; Magnetic Resonance Spectroscopy; Marine; MCF-7 Cells; Neoplasms - drug therapy; Neoplasms - pathology; Peptides, Cyclic - chemistry; Peptides, Cyclic - isolation & purification; Peptides, Cyclic - pharmacology; Porifera - microbiology; pyripyropene T; similanamide; similanpyrone C
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md13031432

A new isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 2 the stereochemistry of its amino acid constituents was determined by chiral HPLC analysis of the hydrolysate by co-injection with the d and l amino acids standards. Compounds 2 and 3 were evaluated for their in vitro growth inhibitory activity against MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A373 (melanoma) cell lines, as well as antibacterial activity against reference strains and the environmental multidrug-resistant isolates (MRS and VRE). Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity.