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

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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.

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          The power of ion mobility-mass spectrometry for structural characterization and the study of conformational dynamics.

          Mass spectrometry is a vital tool for molecular characterization, and the allied technique of ion mobility is enhancing many areas of (bio)chemical analysis. Strong synergy arises between these two techniques because of their ability to ascertain complementary information about gas-phase ions. Ion mobility separates ions (from small molecules up to megadalton protein complexes) based on their differential mobility through a buffer gas. Ion mobility-mass spectrometry (IM-MS) can thus act as a tool to separate complex mixtures, to resolve ions that may be indistinguishable by mass spectrometry alone, or to determine structural information (for example rotationally averaged cross-sectional area), complementary to more traditional structural approaches. Finally, IM-MS can be used to gain insights into the conformational dynamics of a system, offering a unique means of characterizing flexibility and folding mechanisms. This Review critically describes how IM-MS has been used to enhance various areas of chemical and biophysical analysis.
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            The isothiocyanate produced from glucomoringin inhibits NF-kB and reduces myeloma growth in nude mice in vivo.

            Glucosinolates (GLs), natural compounds extracted from Brassicaceae and precursors of isothiocyanates (ITCs), have been studied in the last decades mostly due to their chemopreventive activity and, more recently, for their potential use as novel chemotherapeutics. The aim of the present study was to investigate the in vitro and in vivo activity of glucomoringin (GMG), an uncommon member of the GLs family, and to compare it with glucoraphanin (GRA), one of the most studied GL. We have evaluated the potency of both compounds in inducing cell death, cell cycle perturbations, apoptosis, NF-kB inhibition and GST-pi activity in human carcinoma cells with different GST-pi contents as well as in human multiple myeloma and leukaemia cell lines. GMG-derived ITC (GMG-ITC) showed to be more effective compared to GRA-derived ITC (Sulforaphane), especially in inhibiting NF-kB activity and inducing apoptosis through a caspase-dependent pathway; these effects were more pronounced in myeloma cells, in which we could also observe a long lasting growth inhibitory effect, probably due to NF-kB inhibition, which is considered essential for myeloma cell survival. Both GLs were able to induce cell death in the muM range in all tested cell lines but caused cell cycle perturbations only in myeloma cells; they were also able to modulate the GST/GSH pathway by causing a 3-fold increase in GST-pi activity in MCF7 cells. In vivo study showed that pure GMG-ITC was only slightly active in a carcinoma mice model, whereas it had significant antitumoral activity in a myeloma model, causing little toxicity. 2009 Elsevier Inc. All rights reserved.
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              Antiinflammatory activity of glucomoringin isothiocyanate in a mouse model of experimental autoimmune encephalomyelitis.

              Glucomoringin (4(α-L-rhamnosyloxy)-benzyl glucosinolate) (GMG) is an uncommon member of glucosinolate group belonging to the Moringaceae family, of which Moringa oleifera Lam. is the most widely distributed. Bioactivation of GMG with the enzyme myrosinase forms the corresponding isothiocyanate (4(α-L-rhamnosyloxy)-benzyl isothiocyanate) (GMG-ITC), which can play a key role in antitumoral activity and counteract the inflammatory response. The aim of this study was to assess the effect of GMG-ITC treatment in an experimental mouse model of multiple sclerosis (MS), an inflammatory demyelinating disease with neurodegeneration characterized by demyelinating plaques, neuronal, and axonal loss. For this reason, C57Bl/6 male mice were injected with myelin oligodendrocyte glycoprotein35-55 which is able to evoke an autoimmune response against myelin fibers miming human multiple sclerosis physiopatogenesis. Results clearly showed that the treatment was able to counteract the inflammatory cascade that underlies the processes leading to severe MS. In particular, GMG-ITC was effective against proinflammatory cytokine TNF-α. Oxidative species generation including the influence of iNOS, nitrotyrosine tissue expression and cell apoptotic death pathway was also evaluated resulting in a lower Bax/Bcl-2 unbalance. Taken together, this work adds new interesting properties and applicability of GMG-ITC and this compound can be suggested as a useful drug for the treatment or prevention of MS, at least in association with current conventional therapy.
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                Author and article information

                Contributors
                Role: Academic Editor
                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                13 July 2018
                July 2018
                : 23
                : 7
                : 1714
                Affiliations
                [1 ]Plateforme Analytique, Institut de Chimie de Picardie FR 3085 CNRS, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France; serge.pilard@ 123456u-picardie.fr
                [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; renato.iori48@ 123456gmail.com
                [3 ]Istituti di Ricovero e Cura a Carattere Scientifico, IRCCS Centro Neurolesi “Bonino-Pulejo”, Via Provinciale Palermo, Contrada Casazza, 98124 Messina, Italy; tsrajanpillai@ 123456gmail.com (T.S.R.); emazzon.irccs@ 123456gmail.com (E.M.)
                [4 ]Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV, EA 4492), ULCO, F-59140 Dunkerque, France; david.landy@ 123456univ-littoral.fr
                [5 ]Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans et CNRS, UMR 7311, BP 6759, F-45067 Orléans, France; patrick.rollin@ 123456univ-orleans.fr
                [6 ]Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources UMR 7378, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France
                Author notes
                [* ]Correspondence: david.mathiron@ 123456u-picardie.fr (D.M.); florence.pilard@ 123456u-picardie.fr (F.D.-P.); Tel.: +33-322-828-856 (D.M.)
                [†]

                Dedicated to Dr. Bruno Perly in recognition of his constant inspiration, a great scientist and our friend, who prematurely passed away in 2009.

                Author information
                https://orcid.org/0000-0002-2493-6941
                https://orcid.org/0000-0001-8728-6176
                https://orcid.org/0000-0002-5073-717X
                https://orcid.org/0000-0002-2841-0023
                Article
                molecules-23-01714
                10.3390/molecules23071714
                6099948
                30011859
                6cd1813e-4dcd-47f9-b8a3-5764e2d4047f
                © 2018 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 06 June 2018
                : 10 July 2018
                Categories
                Article

                moringa oleifera,cyclodextrin,moringin,isothiocyanate,anti-inflammatory,nuclear magnetic resonance (nmr),mass spectrometry (ms)

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