Chemo-diversification of plant extracts using a generic bromination reaction and monitoring by metabolite profiling

Article Article scientifique Article Chemo-diversification of plant extracts using a generic bromination reaction and monitoring by metabolite profiling eng 2019 author Righi Davide 816112 author Marcourt Laurence 729234 author Koval Alexey 0000-0002-8920-4426 910996 author Ducret Verena 596806 author Pellissier Léonie 856801 author Mainetti Alice 780240 author Katanaev Vladimir 0000-0002-7909-5617 910192 author Perron Karl 45679 author Wolfender Jean-Luc 135649 author Ferreira Queiroz Emerson 135675 171-182 10.1021/acscombsci.8b00132 30607939 2156-8944 A generic procedure for direct bromination of polyphenol in crude plant extracts was developed to generate multiple "unnatural" halogenated natural products for further bioassay evaluation. To better control the halogenation procedure, the bromination was optimized with a flavonoid standard, and the reactions were monitored by high-performance liquid chromatography photometric diode array coupled to the evaporative light scattering detection (ELSD). ELSD detection was successfully used for a relative yield estimation of the compounds obtained. From the halogenation of hesperitin (11), five brominated compounds were obtained. After optimization, the reaction was successfully applied to the methanolic extract of Citrus sinensis peels, a typical waste biomass and also to the methanolic extract of the medicinal plant Curcuma longa. In both cases, the methanolic extracts were profiled by NMR for a rapid estimation of the polyphenol versus primary metabolite content. An enriched secondary metabolites extract was obtained using vacuum liquid chromatography and submitted to bromination. Metabolite profiling performed by ultrahigh purity liquid chromatography time-of-flight high-resolution mass spectrometry revealed the presence of various halogenated products. To isolate these compounds, the reactions were scaled up, and six halogenated analogues were isolated and fully characterized by NMR and high-resolution electrospray ionization mass spectrometry analyses. The antibacterial properties of these compounds were evaluated using in vitro bioassays against multiresistant strains of Staphylococcus aureus and Pseudomonas aeruginosa. Some of the halogenated derivatives obtained presented moderate antibacterial properties. Animals Cell Line Frizzled Receptors/metabolism High-Throughput Screening Assays/methods Humans Neoplasms/metabolism Dewey 580 Dewey 612 Dewey 615 Swiss National Science Foundation SNF R'Equip Grant No. 316030_164095 CH 45 Département des sciences végétales 163 31 Section des sciences pharmaceutiques 17 134 Département de physiologie cellulaire et métabolisme 21C false 1264 Voies de signalisation oncogéniques 998 ACS Combinational Science 21 3 07c59be6-6647-41b6-bb40-b458763f5132 Article (Published version) Restricted acscombsci.8b00132.pdf 1788586 application/pdf restrictedAccess Faculté des sciences / Section de biologie / Département des sciences végétales Faculté des sciences / Section des sciences pharmaceutiques Faculté de médecine / Section de médecine fondamentale / Département de physiologie cellulaire et métabolisme

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Chemo-diversification of plant extracts using a generic bromination reaction and monitoring by metabolite profiling	ACS Combinational Science			2019	412	0

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