A novel aryl-hydrazide from the marine lichen Lichina pygmaea: isolation, synthesis of derivatives, and cytotoxicity assays.
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.
Roullier
Catherine
C
EA 4090 'Substances licheniques et photoprotection', Faculté des Sciences pharmaceutiques et Biologiques, Université Européenne de Bretagne, Université de Rennes, Rennes Cedex, France.
Chollet-Krugler
Marylène
M
Weghe
Pierre van de
Pv
Devehat
Françoise Lohézic-Le
FL
Boustie
Joël
J
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
D001593:Benzyl Compounds; D006834:Hydrazines; D010659:Phenylhydrazines; C553439:pygmeine; C030299:phenylhydrazine; C029424:hydrazine; D018698:Glutamic Acid