Callyaerins A-F and H, new cytotoxic cyclic peptides from the Indonesian marine sponge Callyspongia aerizusa

S.R.M. Ibrahim, C.C. Min, F. Teuscher, R. Ebel, C. Kakoschke, W. Lin, V. Wray, R. Edrada-Ebel, P. Proksch

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75 Citations (Scopus)


Bioassay guided fractionation of the EtOAc fraction of the sponge Callyspongia aerizusa yielded seven new cytotoxic cyclic peptides callyaerins A-F (1-6) and H (8). Their structures were determined using extensive 1D ( H, C and DEPT) and 2D (COSY, HMQC, HMBC, TOCSY, and ROESY) NMR and mass spectral (ESI and HRESI-TOF) data. All compounds were cyclic peptides containing ring systems of 5-9 amino acids and side chains of 2-5 amino acids in length. An unusual (Z)-2,3-diaminoacrylic acid unit provided the template for ring closure and afforded the linkage to the peptidic side chain which was always initiated with a proline moiety. All peptides contained three or more proline residues and the remaining residues were predominantly hydrophobic residues with all amino acids present in the l form. Callyaerins A-F (1-6) and H (8) showed biological activity in antibacterial assays and in various cytotoxicity assays employing different tumour cell-lines (L5178Y, HeLa, and PC12). Callyaerins E (5) and H (8) exhibited strong activity against the L5178Y cell line with ED values of 0.39 and 0.48 µM, respectively. On the other hand, callyaerin A (1) showed strong inhibitory properties towards C. albicans.
Original languageEnglish
Pages (from-to)4947-4956
Number of pages10
JournalBioorganic & Medicinal Chemistry
Issue number14
Early online date11 Jun 2010
Publication statusPublished - 15 Jul 2010

Bibliographical note

S. R. M. Ibrahim wishes to thank the Egyptian Government for a scholarship. We are indebted to Professor Dr. W. E. G. Müller (Institute für Physiologische Chemie, Duesbergweg 6, D-55099 Mainz, Germany) for cytotoxicity testing. This project was supported by grants of the BMBF and MOST awarded to Professor Peter Proksch and Professor Wenhan Lin.


  • Callyspongia aerizusa
  • Callyaerins
  • Proline-rich cyclic peptides
  • Cytotoxicity
  • Antibacterial
  • Antifungal


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