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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
David MathironFlorence Djedaïni-Pilard

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.

References

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Citations

Feb 27, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gigliola BorgonovoAngela Bassoli
Feb 26, 2020·Biomolecules·Estefania OlivaFlorence Djedaini-Pilard
Aug 24, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Letizia RomeoEmanuela Mazzon
Sep 10, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jae-Ung LeeHan Bin Oh
Jan 11, 2021·Journal of Pharmaceutical and Biomedical Analysis·Keabetswe MasikeAndré de Villiers

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Methods Mentioned

BETA
NMR
nuclear magnetic resonance
electron capture dissociation
light microscopy
solubility

Software Mentioned

ERETIC
dosy2d
MOR
Abalone
MassLynx
TOPSPIN

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