title: Maackiain 3-O-(6'-O-malonyl-beta-D-glucopyranoside) from Oudneya africana, a powerful inhibitor of porcine kidney acylase I.
abstract: The inhibitory effect of phenolic extracts of several plants from the Algerian Atlas used traditionally in Arab folk medicine was tested on the porcine kidney acylase I activity. An endemic Saharan plant of the Brassicaceae family, Oudneya africana, has shown a strong inhibitory effect. The active compound was isolated and purified by semi-preparative HPLC and HPLC-photodiode array detection, and structurally determined using 1H, 13C NMR and mass spectroscopy methods. Results indicate that maackiain 3-O-(6'-O-malonyl-beta-D-glucopyranoside) showed a competitive inhibition of porcine kidney acylase I with a Ki value of 11 microM. The malonyl moiety appeared to be a structural key element for the inhibitory activity. This observation indicates interesting structure-activity relationships for the inhibitory action of this compound on the acylase I and its potential role in the toxicity of haloalkene-derived mercapturates and that of the enzyme in detoxication and bioactivation.
authors.affiliation: Université Paul Cézanne, Institut méditerranéen de recherche en nutrition, Faculté des sciences de St-Jérôme, avenue escadrille Normandie Niemen, 13397 Marseille cedex 20, France. p.stocker@univ.u-3mrs.fr
authors.forename: P
authors.initials: P
authors.lastname: Stocker
authors.forename: M
authors.initials: M
authors.lastname: Yousfi
authors.forename: C
authors.initials: C
authors.lastname: Salmi
authors.forename: J
authors.initials: J
authors.lastname: Perrier
authors.forename: J M
authors.initials: JM
authors.lastname: Brunel
authors.forename: A
authors.initials: A
authors.lastname: Moulin
mesh_terms: D000581:Amidohydrolases / Q000037:antagonists & inhibitors*; D000818:Animals; D019607:Brassicaceae / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005960:Glucosides / Q000302:isolation & purification* / Q000494:pharmacology*; D007668:Kidney / Q000201:enzymology*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D036343:Pterocarpans / Q000302:isolation & purification* / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship; D013552:Swine; D000094162:Phytoalexins
chemical_list: D000581:Amidohydrolases; D005960:Glucosides; D036343:Pterocarpans; C503154:maackiain 3-O-(6'-O-malonyl-beta-D-glucopyranoside); D000094162:Phytoalexins; C019672:aminoacylase I