title: Inactivation of lipoxygenase and cyclooxygenase by natural betalains and semi-synthetic analogues.
abstract: Betalains are natural pigments characteristic of plants of the order Caryophyllales. In this work, the role of betalains in the anti-inflammatory activity described for plant extracts is analysed in terms of the inactivation of the enzymes involved in the biochemical response (lipoxygenase and cyclooxygenase). Pure natural betalains and semi-synthetic analogues are demonstrated to promote a significant reduction of the enzymes activity. Reactions were followed spectrophotometrically and by HPLC-DAD. Phenethylamine-betaxanthin was the most potent in the inactivation of cyclooxygenase, with a reduction of 32% of the control activity at 125μM, while the natural pigment betanidin and a betalain analogue derived from indoline resulted as the most potent inactivators of lipoxygenase, with IC50 values of 41.4 and 40.1μM, respectively. Molecular docking studies revealed that betalains interact with the lipoxygenase amino acids involved in substrate binding and with Tyr-385 and Ser-530 close to the cyclooxygenase active site, interfering in enzyme catalysis.
authors: Departamento de Bioquímica y Biología Molecular A, Unidad Docente de Biología, Facultad de Veterinaria, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, Murcia, Spain.
authors: Pedro J
authors: PJ
authors: Vidal
authors: Departamento de Bioquímica y Biología Molecular A, Unidad Docente de Biología, Facultad de Veterinaria, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, Murcia, Spain; Murcia Biomedical Research Institute (IMIB), Murcia, Spain.
authors: José M
authors: JM
authors: López-Nicolás
authors: Departamento de Bioquímica y Biología Molecular A, Unidad Docente de Biología, Facultad de Veterinaria, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, Murcia, Spain; Murcia Biomedical Research Institute (IMIB), Murcia, Spain. Electronic address: fgandia@um.es.
authors: Fernando
authors: F
authors: Gandía-Herrero
authors: Departamento de Bioquímica y Biología Molecular A, Unidad Docente de Biología, Facultad de Veterinaria, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, Murcia, Spain; Murcia Biomedical Research Institute (IMIB), Murcia, Spain.
authors: Francisco
authors: F
authors: García-Carmona
mesh_terms: D027461:Beta vulgaris / Q000737:chemistry; D050858:Betalains / Q000138:chemical synthesis / Q000737:chemistry*; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D004789:Enzyme Activation; D006801:Humans; D007700:Kinetics; D008084:Lipoxygenase / Q000737:chemistry*; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry*; D011451:Prostaglandin-Endoperoxide Synthases / Q000737:chemistry*
chemical_list: D016861:Cyclooxygenase Inhibitors; D016859:Lipoxygenase Inhibitors; D010936:Plant Extracts; D050858:Betalains; D008084:Lipoxygenase; D011451:Prostaglandin-Endoperoxide Synthases
keywords: Anti-inflammatory; Betalain; Biological activity; Docking; Structure–activity