A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation †
David Mathiron,
Renato Iori,
Serge Pilard,
Thangavelu Soundara Rajan,
David Landy,
Emanuela Mazzon,
Patrick Rollin,
Florence Djedaïni-Pilard
Affiliations
David Mathiron
Plateforme Analytique, Institut de Chimie de Picardie FR 3085 CNRS, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France
Renato Iori
Consiglio per la Ricerca in Agricoltura e L’analisi Dell’economia Agraria, Centro di Ricerca Agricoltura e Ambiente (CREA-AA), Via di Corticella 133, 40128 Bologna, Italy
Serge Pilard
Plateforme Analytique, Institut de Chimie de Picardie FR 3085 CNRS, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France
Thangavelu Soundara Rajan
Istituti di Ricovero e Cura a Carattere Scientifico, IRCCS Centro Neurolesi “Bonino-Pulejo”, Via Provinciale Palermo, Contrada Casazza, 98124 Messina, Italy
David Landy
Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV, EA 4492), ULCO, F-59140 Dunkerque, France
Emanuela Mazzon
Istituti di Ricovero e Cura a Carattere Scientifico, IRCCS Centro Neurolesi “Bonino-Pulejo”, Via Provinciale Palermo, Contrada Casazza, 98124 Messina, Italy
Patrick Rollin
Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans et CNRS, UMR 7311, BP 6759, F-45067 Orléans, France
Florence Djedaïni-Pilard
Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources UMR 7378, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France
Moringin, obtained via enzymatic conversion of the glucosinolate precursor glucomoringin, is an uncommon member of the isothiocyanate class, and has been proven to possess a broad range of biological activities such as antitumor activity, protection against neurodegenerative disorders and bactericidal effects. Since moringin is weakly soluble in water and unstable in aqueous medium, cyclodextrins (CDs) were considered for the development of a new moringin formulation, with a view to improving its solubility and stability in aqueous solution for use as an anti-inflammatory. A combined structural study using proton nuclear magnetic resonance (1H-NMR), diffusion-ordered spectroscopy (DOSY) and ion mobility mass spectrometry (IM-MS) is reported, highlighting the formation of a 1:1 α-CD/moringin inclusion complex. The association constant K was determined (1300 M−1 at 300 K). Completion of the structural characterization was performed by T-ROESY and MS/MS experiments, which evidenced the mode of penetration of moringin into α-CD. Finally, the “chaperone-like” properties of α-CD with respect to the stability of moringin have been highlighted.
