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Mar. Drugs 2015, 13(3), 1432-1450; doi:10.3390/md13031432

A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013

1
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, Portugal
3
Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP), Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
4
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand
5
Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal
*
Author to whom correspondence should be addressed.
Academic Editor: Johannes F. Imhoff
Received: 27 January 2015 / Revised: 4 March 2015 / Accepted: 9 March 2015 / Published: 17 March 2015
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Abstract

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. View Full-Text
Keywords: Aspergillus similanensis; cyclic hexapeptide; similanamide; isocoumarin; similanpyrone C; pyripyropene T Aspergillus similanensis; cyclic hexapeptide; similanamide; isocoumarin; similanpyrone C; pyripyropene T
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Prompanya, C.; Fernandes, C.; Cravo, S.; Pinto, M.M.M.; Dethoup, T.; Silva, A.M.S.; Kijjoa, A. A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013. Mar. Drugs 2015, 13, 1432-1450.

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