Structural characterization of inclusion complexes between cyanidin-3-0-glucoside and beta-cyclodextrin

• Type: Article in International Scientific Journal
• Date: 2014

Authors

Ana Fernandes (Author) Other; Galya Ivanova (Author) Other; Natercia F Bras (Author) FCUP; Nuno Mateus (Author) FCUP; Maria J Ramos (Author) FCUP; Maria Rangel (Author) ICBAS; Victor de Freitas (Author) FCUP

Journal

Title: Carbohydrate Polymers

Vol. 102

Pages: 269-277

ISSN: 0144-8617

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 61 Citations

Scopus - 65 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-008-K75

DOI: 10.1016/j.carbpol.2013.11.037

Abstract (EN): Inclusion complex formation between the multiple equilibrium forms of cyanidin-3-O-glucoside (cy3gIc) and p-cyclodextrin (beta-CD) was investigated using a combined approach of NMR spectroscopy and Molecular Dynamics simulation. Diffusion ordered NMR spectroscopy (DOSY) and study of nuclear Overhauser effects (NOE) were used to determine the selective intermolecular interactions and structure of these complexes in aqueous solution. The observed chemical shift displacements of resonance signals of protons from the interior of beta-CD cavity and protons belonging to the hemiketal (B) and cis-chalcone forms (Cc), the diffusion measurements using DOSY and the NOE studies have anticipated the formation of an inclusion complex between these two forms and beta-CD. The analysis of the NMR spectral data has shown no evidence of internal interaction between beta-CD and the flavylium cation (AH(+)) or trans-chalcone (Ct) forms of cy3gIc. The hemiketal formed a 1:1 inclusion complex with beta-cyclodextrin in which the pyranic C ring is deeply included inside the beta-CD cavity while B ring lies on the plane of the wider rim of beta-CD. The structure of the complexes was also clarified through a theoretical approach by Molecular Dynamics simulation.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9