The in vitro antioxidant properties of the Al-quercetin/beta CD and Al-catechin/beta CD inclusion compounds, rationalized in terms of their electrochemical behaviour

Inclusion compounds of Al-quercetin and Al-catechin complexes with beta-cyclodextrin (beta CD) were investigated. The complex and the inclusion compound of quercetin are more effective DPPHaEuro cent scavengers than the corresponding catechin compounds and the inclusion does not compromise their scavenging abilities, with only a slight decrease in the EC50 values. This is in accordance with the electrochemical data, which revealed that the inclusion compounds have lower diffusion coefficients in aqueous solution than the non-included compounds. For the quercetin compounds, some spectroscopic properties were also addressed by means of UV-visible and NMR measurements in aqueous media.

Synthesis and characterization of [Ru(eta(6)-C10H14)(dppf)X][PF6] (X = Cl, Br, I, SnF3) compounds: The X-ray structure of [Ru(eta(6)-C10H14)(dppf)Cl][SnCl3]center dot 0.45CH(2)Cl(2)

The arene-ruthenium complex [Ru(eta(6)-C10H14)(dppf)Cl]PF6 (1) was used as a precursor for the syntheses of the [Ru(eta(6)-C10H14)(dppf)Br]PF6 (2), [Ru(eta(6)-C10H14)(dppf)I]PF6 (3). [Ru(eta(6)-C10H14)(dppf)SnF3]PF6 (4) and [Ru(eta(6)-C10H14)(dppf)Cl][SnCl3]center dot 0.45CH(2)Cl(2) (5) complexes by its reactions with KBr, Kl, SnF2 and SnCl2. respectively. All of the compounds were characterized by NMR, IR, Fe-57 and Sn-119-Mossbauer spectroscopy, and cyclic voltammetry. The single-crystal X-ray structure analysis of the [Ru(eta(6)-C10H14)(dppf)Cl] [SnCl3]center dot 0.45CH(2)Cl(2) complex revealed the expected piano-stool geometry. Cyclic voltammograms of the complexes showed only one quasi-reversible electrochemical process, involving the oxidation of Fe(II) and Ru(II) at the same potential, which was confirmed by exhaustive electrolysis experiments. Fe-57-Mossbauer parameters obtained for the complexes (1-5) were fitted with one doublet corresponding to a site of one iron(II). The Sn-119-Mossbauer parameters of the complex (4) indicate that tin is tetra covalent. (c) 2012 Elsevier Ltd. All rights reserved.

Biomimetic in vitro oxidation of lapachol: A model to predict and analyse the in vivo phase I metabolism of bioactive compounds

The bioactive naphtoquinone lapachol was studied in vitro by a biomimetic model with Jacobsen catalyst (manganese(III) salen) and iodosylbenzene as oxidizing agent. Eleven oxidation derivatives were thus identified and two competitive oxidation pathways postulated. Similar to Mn(III) porphyrins, Jacobsen catalyst mainly induced the formation of para-naphtoquinone derivatives of lapachol, but also of two ortho-derivatives. The oxidation products were used to develop a GC MS (SIM mode) method for the identification of potential phase I metabolites in vivo. Plasma analysis of Wistar rats orally administered with lapachol revealed two metabolites, alpha-lapachone and dehydro-alpha-lapachone. Hence, the biomimetic model with a manganese salen complex has evidenced its use as a valuable tool to predict and elucidate the in vivo phase I metabolism of lapachol and possibly also of other bioactive natural compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.