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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Abstract

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
Volume18
Issue number14
Early online date11 Jun 2010
DOIs
Publication statusPublished - 15 Jul 2010

Keywords

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

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    Ibrahim, S. R. M., Min, C. C., Teuscher, F., Ebel, R., Kakoschke, C., Lin, W., Wray, V., Edrada-Ebel, R., & Proksch, P. (2010). Callyaerins A-F and H, new cytotoxic cyclic peptides from the Indonesian marine sponge Callyspongia aerizusa. Bioorganic & Medicinal Chemistry, 18(14), 4947-4956. https://doi.org/10.1016/j.bmc.2010.06.012