title: A novel aryl-hydrazide from the marine lichen Lichina pygmaea: isolation, synthesis of derivatives, and cytotoxicity assays.
abstract: A new aryl-hydrazide l-glutamic acid derivative, pygmeine (3), was isolated from a methanolic extract of Lichina pygmaea, a marine lichen. Synthetic derivatives obtained via a two-step coupling of l-glutamic acid with phenylhydrazine moieties were useful to elucidate the structure of 3 and to carry out biological assays. Thus, the cytotoxicity of the ortho-, meta-, and para-hydroxyl isomers along with their respective benzyl intermediates, and a natural methoxylated analog, were evaluated on murine and human melanoma cells (B16, A375). The para-hydroxyl isomer 6 was found to be the most active (IC(50)=1.6 microM) on B16 cells.
authors.affiliation: EA 4090 'Substances licheniques et photoprotection', Faculté des Sciences pharmaceutiques et Biologiques, Université Européenne de Bretagne, Université de Rennes, Rennes Cedex, France.
authors.forename: Catherine
authors.initials: C
authors.lastname: Roullier
authors.forename: Marylène
authors.initials: M
authors.lastname: Chollet-Krugler
authors.forename: Pierre van de
authors.initials: Pv
authors.lastname: Weghe
authors.forename: Françoise Lohézic-Le
authors.initials: FL
authors.lastname: Devehat
authors.forename: Joël
authors.initials: J
authors.lastname: Boustie
mesh_terms: D000818:Animals; D001593:Benzyl Compounds / Q000737:chemistry; D045744:Cell Line, Tumor; D018698:Glutamic Acid / Q000737:chemistry; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000627:therapeutic use; D007536:Isomerism; D008011:Lichens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008546:Melanoma, Experimental / Q000188:drug therapy; D051379:Mice; D008968:Molecular Conformation; D010659:Phenylhydrazines / Q000737:chemistry
chemical_list: D001593:Benzyl Compounds; D006834:Hydrazines; D010659:Phenylhydrazines; C553439:pygmeine; C030299:phenylhydrazine; C029424:hydrazine; D018698:Glutamic Acid