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Bioorg Med Chem. 2010 Aug 15;18(16):6006-11. doi: 10.1016/j.bmc.2010.06.066. Epub 2010 Jun 25.

New bioactive halenaquinone derivatives from South Pacific marine sponges of the genus Xestospongia.

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Laboratoire des Molécules de Communication et Adaptation des Micro-organismes, FRE 3206 CNRS, Muséum National d'Histoire Naturelle, Paris, France.


Bioassay-directed fractionation of South Pacific marine sponges of the genus Xestospongia has led to the isolation of a number of halenaquinone-type polyketides, including two new derivatives named xestosaprol C methylacetal 7 and orhalquinone 8. Chemical characterization of these two new compounds was achieved by extensive 1D and 2D NMR spectroscopic studies. Evaluation of anti-phospholipase A(2), anti-farnesyltransferase and antiplasmodial activities of this series is presented and structure/activity relationships are discussed. Orhalquinone 8 displayed a significant inhibition of both human and yeast farnesyltransferase enzymes, with IC(50) value of 0.40 microM and was a moderate growth inhibitor of Plasmodium falciparum.

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