Axinellins A and B: New proline-containing antiproliferative cyclopeptides from the vanuatu sponge Axinella carteri

Antonio Randazzo, Fabrizio Dal Piaz, Stefania Orrù, Cécile Debitus, Christos Roussakis, Piero Pucci, Luigi Gomez-Paloma

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)2659-2665
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number11
Publication statusPublished - Nov 1998

Keywords

  • 2D NMR
  • Amino acids
  • Axinella carteri
  • Cyclopeptides
  • ESMS
  • Macrocycles
  • MS
  • Natural products
  • Peptides
  • Sponge

ASJC Scopus subject areas

  • Organic Chemistry

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