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

Prompanya C, Fernandes C, Cravo S, Pinto MM, Dethoup T, Silva AM, Kijjoa A - Mar Drugs (2015)

Bottom Line: 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.Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity.

View Article: PubMed Central - PubMed

Affiliation: ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. chadaporn@buu.ac.th.

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.

No MeSH data available.


Related in: MedlinePlus

Secondary metabolites from Aspergillus similanensis KUFA0013.
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marinedrugs-13-01432-f001: Secondary metabolites from Aspergillus similanensis KUFA0013.

Mentions: In our ongoing search for new natural products with antibacterial and anticancer activities produced by the marine-derived fungi of the genera Neosartorya and Aspergillus, we have recently reported the isolation of new isocoumarins similanpyrones A and B, a new chevalone (chevalone E), and a new natural product pyripyrone S; besides the previously reported chevalone B and C, a meroterpenoid S14-95, and pyripyropene E, from the crude ethyl acetate extract of the undescribed marine sponge-associated fungus Aspergillus similanensis KUFA 0013 [29]. Reexamination of the fractions remaining from the previous study of this fungus led to the isolation of a new 8-hydroxy-3-methylisocoumarin derivative, which we have named similanpyrone C (1), a new cyclic hexapeptide, similanamide (2), and a new pyripyropene analog, pyripyropene T (3) (Figure 1). Hydrolysis of compound 2, followed by HPLC analysis of its hydrolysate using a chiral column, led to the elucidation of its amino acid constituents. Compounds 2 and 3 were evaluated for their antibacterial activity as well their cytotoxicity against three human cancer cell lines.


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

Prompanya C, Fernandes C, Cravo S, Pinto MM, Dethoup T, Silva AM, Kijjoa A - Mar Drugs (2015)

Secondary metabolites from Aspergillus similanensis KUFA0013.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4377992&req=5

marinedrugs-13-01432-f001: Secondary metabolites from Aspergillus similanensis KUFA0013.
Mentions: In our ongoing search for new natural products with antibacterial and anticancer activities produced by the marine-derived fungi of the genera Neosartorya and Aspergillus, we have recently reported the isolation of new isocoumarins similanpyrones A and B, a new chevalone (chevalone E), and a new natural product pyripyrone S; besides the previously reported chevalone B and C, a meroterpenoid S14-95, and pyripyropene E, from the crude ethyl acetate extract of the undescribed marine sponge-associated fungus Aspergillus similanensis KUFA 0013 [29]. Reexamination of the fractions remaining from the previous study of this fungus led to the isolation of a new 8-hydroxy-3-methylisocoumarin derivative, which we have named similanpyrone C (1), a new cyclic hexapeptide, similanamide (2), and a new pyripyropene analog, pyripyropene T (3) (Figure 1). Hydrolysis of compound 2, followed by HPLC analysis of its hydrolysate using a chiral column, led to the elucidation of its amino acid constituents. Compounds 2 and 3 were evaluated for their antibacterial activity as well their cytotoxicity against three human cancer cell lines.

Bottom Line: 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.Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity.

View Article: PubMed Central - PubMed

Affiliation: ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. chadaporn@buu.ac.th.

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.

No MeSH data available.


Related in: MedlinePlus