Bioorganic & Medicinal Chemistry Letters 2010-08-01

A novel aryl-hydrazide from the marine lichen Lichina pygmaea: isolation, synthesis of derivatives, and cytotoxicity assays.

Catherine Roullier, Marylène Chollet-Krugler, Pierre van de Weghe, Françoise Lohézic-Le Devehat, Joël Boustie

Index: Bioorg. Med. Chem. Lett. 20(15) , 4582-6, (2010)

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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.Copyright 2010 Elsevier Ltd. All rights reserved.