Issue 16, 2014

An inelastic neutron scattering study of dietary phenolic acids

Abstract

The conformational preferences and hydrogen-bonding motifs of several potential chemopreventive hydroxycinnamic derivatives were determined by inelastic neutron scattering spectroscopy. The aim is to understand their recognized beneficial activity and establish reliable structure–activity relationships for these types of dietary phytochemicals. A series of phenolic acids with different hydroxyl/methoxyl ring substitution patterns were studied: trans-cinnamic, p-coumaric, m-coumaric, trans-caffeic and ferulic acids. Their INS spectra were completely assigned by theoretical calculations performed at the Density Functional Theory level, for the isolated molecule, dimeric centrosymmetric species and the solid (using plane-wave expansion approaches). Access to the low energy vibrational region of the spectra enabled the identification of particular modes associated with intermolecular hydrogen-bonding interactions, which are the determinants of the main conformational preferences and antioxidant capacity of these systems.

Graphical abstract: An inelastic neutron scattering study of dietary phenolic acids

Article information

Article type
Paper
Submitted
22 Jan 2014
Accepted
03 Mar 2014
First published
03 Mar 2014

Phys. Chem. Chem. Phys., 2014,16, 7491-7500

Author version available

An inelastic neutron scattering study of dietary phenolic acids

M. P. M. Marques, L. A. E. Batista de Carvalho, R. Valero, N. F. L. Machado and S. F. Parker, Phys. Chem. Chem. Phys., 2014, 16, 7491 DOI: 10.1039/C4CP00338A

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