Peyssonenynes a and B, novel enediyne oxylipins with DNA methyl transferase inhibitory activity from the red marine alga peyssonneliacaulifera

Journal of Natural Products
Kerry L McPhailWilliam H Gerwick

Abstract

Two novel omega3 fatty acids, obtained as monoacyl glycerol derivatives, were isolated as DNA methyl transferase inhibitors following bioassay-guided fractionation of the Fijian red marine alga Peyssonnelia caulifera. Both active metabolites, peyssonenynes A (1) and B (2), possess an unusual enediyne motif, whereas an inactive co-metabolite, peyssopyrone (3), contains an unusual gamma-pyrone functionality. The molecular structures of all three compounds were determined by NMR spectroscopy in combination with UV, IR, and MS data analysis. The instability of the enediyne monoacyl glycerol derivatives prevented their complete stereochemical assignments.

References

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Citations

Feb 3, 2006·Natural Product Reports·John W BluntMichèle R Prinsep
Jun 26, 2014·Cancer Letters·Michael SchnekenburgerMarc Diederich
Jan 26, 2016·Marine Drugs·Mariana BarbosaPaula B Andrade
Jul 27, 2015·Applied Biochemistry and Biotechnology·Meenakshi JhaAnju Shrivastava
Dec 24, 2011·Natural Product Reports·John W BluntMichèle R Prinsep
Sep 15, 2012·Natural Product Reports·Klaus-Dieter FeussnerChris M Ireland
Dec 25, 2012·Natural Product Reports·John W BluntMichèle R Prinsep
Aug 11, 2010·Molecular Diversity·Jose L Medina-FrancoFrank Lyko
Oct 11, 2012·ChemMedChem·Patricia García-DomínguezÁngel R de Lera
Dec 12, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Santiago LascanoPaola B Arimondo
Dec 16, 2006·ACS Chemical Biology·Aaron T DosseyArthur S Edison
Jan 14, 2009·Journal of Natural Products·Maria KladiVassilios Roussis
Dec 20, 2014·Chemical Reviews·Zhen-Fang ZhouYue-Wei Guo

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