Maackiain 3-O-(6′-O-malonyl-β-D-glucopyranoside) from Oudneya africana, a powerful inhibitor of porcine kidney acylase I

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-β-d-glucopyranoside) showed a competitive inhibition of porcine kidney acylase I with a Ki value of 11 μM. 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.