Gymnangiamide, a cytotoxic pentapeptide from the marine hydroid Gymnangium regae

J Org Chem. 2004 Apr 30;69(9):3036-42. doi: 10.1021/jo0303113.

Abstract

A cytotoxic aqueous extract from the marine hydroid Gymnangium regae provided a novel linear pentapeptide, designated gymnangiamide (1). The planar structure of 1 was elucidated by interpretation of spectral data as well as chemical degradation and derivatization studies. In addition to the amino acids isoleucine and phenylserine, this peptide contained N-desmethyldolaisoleuine, O-desmethyldolaproine, and alpha-guanidino serine, three residues that have not previously been reported in a natural product. The absolute configurations of the constituent amino/guanidino acids were determined by chemical degradation and derivatization, followed by HPLC and LC-MS comparison with authentic standards. Gymnangiamide (1) was moderately cytotoxic against a number of human tumor cell lines in vitro.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acids / chemistry
  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • Gas Chromatography-Mass Spectrometry
  • Guanidines / chemistry
  • Humans
  • Hydra / chemistry*
  • Magnetic Resonance Spectroscopy
  • Marine Biology
  • Mass Spectrometry
  • Molecular Structure
  • Oligopeptides / chemistry*
  • Oligopeptides / isolation & purification
  • Stereoisomerism

Substances

  • Amino Acids
  • Antineoplastic Agents
  • Guanidines
  • Oligopeptides
  • gymnangiamid