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Mar. Drugs 2017, 15(7), 209; doi:10.3390/md15070209

Bistratamides M and N, Oxazole-Thiazole Containing Cyclic Hexapeptides Isolated from Lissoclinum bistratum Interaction of Zinc (II) with Bistratamide K

1
Medicinal Chemistry Department, PharmaMar S. A., Polígono Industrial La Mina Norte, Avenida de los Reyes 1, 28770 Madrid, Spain
2
Department of Chemistry, Faculty of Sciences and Center for Advanced Scientific Research (CICA), University of A Coruña, 15071 A Coruña, Spain
*
Authors to whom correspondence should be addressed.
Received: 24 May 2017 / Revised: 17 June 2017 / Accepted: 26 June 2017 / Published: 1 July 2017
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Abstract

Two novel oxazole-thiazole containing cyclic hexapeptides, bistratamides M (1) and N (2) have been isolated from the marine ascidian Lissoclinum bistratum (L. bistratum) collected in Raja Ampat (Papua Bar, Indonesia). The planar structure of 1 and 2 was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 and 2 was determined by the application of the Marfey’s and advanced Marfey’s methods after ozonolysis followed by acid-catalyzed hydrolysis. The interaction between zinc (II) and the naturally known bistratamide K (3), a cyclic hexapeptide isolated from a different specimen of Lissoclinum bistratum, was monitored by 1H and 13C NMR. The results obtained are consistent with the proposal that these peptides are biosynthesized for binding to metal ions. Compounds 1 and 2 display moderate cytotoxicity against four human tumor cell lines with GI50 values in the micromolar range. View Full-Text
Keywords: cytotoxic; sponge; Lissoclinum bistratum; cyclic hexapeptides; bistratamides; Zn complex cytotoxic; sponge; Lissoclinum bistratum; cyclic hexapeptides; bistratamides; Zn complex
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Urda, C.; Fernández, R.; Rodríguez, J.; Pérez, M.; Jiménez, C.; Cuevas, C. Bistratamides M and N, Oxazole-Thiazole Containing Cyclic Hexapeptides Isolated from Lissoclinum bistratum Interaction of Zinc (II) with Bistratamide K. Mar. Drugs 2017, 15, 209.

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