European Journal of Organic Chemistry · 1998 · 64 citations · 21 references
PharmacyMedicinal ChemistryPharmacologyCancer PharmacologyDrug DiscoveryMass Spectrometric AnalysisMarine Bioactive CompoundsMarine Natural ProductsPeptide AnalysisPeptide ChemistryPeptide Drug DiscoveryPeptide IdentificationBioactive Compounds From Marine SpongesBioactive Marine MetabolitesMarine Compound Structure ElucidationMarine Sponge MetabolitesSponges-derived MetabolitesStructure Elucidation Of Marine Natural ProductsTandem Mass SpectrometryTandem Mass Spectrometry Analysis
Two new bioactive cyclopeptides, named axinellins A (1) and B (2) have been isolated from the marine sponge Axinella carteri. Their structure elucidation was based on two-dimensional (2D) NMR (500 MHz) as well as HRFABMS and ESMS/MS data. All amino acid residues derived from axinellins A and B were found to possess L configuration at Cα by HPLC analysis of their FDAA derivatives (Marfey's method). The amino acid sequence of 1 and 2 was established on the basis of tandem mass spectrometry data (ESMS/MS) and on 1H-1H through-space connectivities observed in NOESY and ROESY spectra. Axinellins A (1) and B (2) exhibited moderate in vitro antitumor activity against human broncopulmonary non-small-cell-lung-carcinoma lines (NSCLC-N6) with IC50 values of 3.0 and 7.3 μg/ml, respectively.
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