Koshikamide B, a cytotoxic peptide lactone from a marine sponge Theonella sp

J Org Chem. 2008 Oct 17;73(20):7889-94. doi: 10.1021/jo801032n. Epub 2008 Sep 24.

Abstract

Koshikamide B (1) has been isolated from two separate collections of the marine sponge Theonella sp. as the major cytotoxic constituent. Koshikamide B is a 17-residue peptide lactone composed of six proteinogenic amino acids, two D-isomers of proteinogenic amino acids, seven N-methylated amino acids, and two unusual amino acid residues. The unusual amino acids are N(delta)-carbamoylasparagine and 2-(3-amino-2-hydroxy-5-oxopyrrolidin-2-yl)propionic acid (AHPP); the former is first found as the constituent of peptides, whereas the latter is a new amino acid residue. The N-terminus of koshikamide B is blocked by a methoxyacetyl group. The structure of koshikamide B (1) has been determined by interpretation of spectral data and analysis of chemical degradation products. Koshikamide B (1) exhibits cytotoxicity against P388 murine leukemia cells and the human colon tumor (HCT-116) cell line with an IC50 value of 0.45 and 7.5 microg/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Asparagine / analogs & derivatives
  • Asparagine / chemistry
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Lactones / chemistry
  • Mice
  • Oligopeptides / chemistry*
  • Oligopeptides / toxicity*
  • Propionates / chemistry
  • Pyrrolidines / chemistry
  • Theonella / chemistry*
  • Theonella / metabolism
  • Tumor Cells, Cultured

Substances

  • 2-(3-amino-2-hydroxy-5-oxopyrrolidin-2-yl)propionic acid
  • Lactones
  • N(delta)-carbamoylasparagine
  • Oligopeptides
  • Propionates
  • Pyrrolidines
  • koshikamide B
  • Asparagine