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Molecules 2018, 23(7), 1714; https://doi.org/10.3390/molecules23071714

A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation

1
Plateforme Analytique, Institut de Chimie de Picardie FR 3085 CNRS, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France
2
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
3
Istituti di Ricovero e Cura a Carattere Scientifico, IRCCS Centro Neurolesi “Bonino-Pulejo”, Via Provinciale Palermo, Contrada Casazza, 98124 Messina, Italy
4
Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV, EA 4492), ULCO, F-59140 Dunkerque, France
5
Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans et CNRS, UMR 7311, BP 6759, F-45067 Orléans, France
6
Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources UMR 7378, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France
Dedicated to Dr. Bruno Perly in recognition of his constant inspiration, a great scientist and our friend, who prematurely passed away in 2009.
*
Authors to whom correspondence should be addressed.
Academic Editor: Bernard Martel
Received: 6 June 2018 / Revised: 30 June 2018 / Accepted: 10 July 2018 / Published: 13 July 2018
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Abstract

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. View Full-Text
Keywords: Moringa oleifera; cyclodextrin; moringin; isothiocyanate; anti-inflammatory; nuclear magnetic resonance (NMR); mass spectrometry (MS) Moringa oleifera; cyclodextrin; moringin; isothiocyanate; anti-inflammatory; nuclear magnetic resonance (NMR); mass spectrometry (MS)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Mathiron, D.; Iori, R.; Pilard, S.; Soundara Rajan, T.; Landy, D.; Mazzon, E.; Rollin, P.; Djedaïni-Pilard, F. A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation . Molecules 2018, 23, 1714.

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