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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
JournalMolecules
Volume23
Issue number7
DOIs
Publication statusPublished - Jul 13 2018

Keywords

  • Animals
  • Isothiocyanates/chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • RAW 264.7 Cells
  • alpha-Cyclodextrins/chemistry

Fingerprint Dive into the research topics of 'A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation †'. Together they form a unique fingerprint.

Cite this