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Solid‐state NMR spectroscopic studies on the interaction of sorbic acid with phospholipid membranes at different pH levels
Author(s) -
Chu Shidong,
Hawes John W.,
Lorigan Gary A.
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2444
Subject(s) - chemistry , sorbic acid , decanoic acid , nmr spectra database , nuclear magnetic resonance spectroscopy , phospholipid , magic angle spinning , crystallography , proton nmr , membrane , analytical chemistry (journal) , stereochemistry , spectral line , organic chemistry , biochemistry , physics , astronomy
Abstract 2 H, 31 P, and 1 H‐magic‐angle‐spinning (MAS) solid‐state NMR spectroscopic methods were used to elucidate the interaction between sorbic acid, a widely used weak acid food preservative, and 1,2‐dimyristoyl‐ sn ‐glycero‐3‐phosphocholine (DMPC) bilayers under both acidic and neutral pH conditions. The linewidth broadening observed in the 31 P NMR powder pattern spectra and the changes in the 31 P longitudinal relaxation time ( T 1 ) indicate interaction with the phospholipid headgroup upon titration of sorbic acid or decanoic acid into DMPC bilayers over the pH range from 3.0 to 7.4. The peak intensities of sorbic acid decrease upon addition of paramagnetic Mn 2+ ions in DMPC bilayers as recorded in the 1 H MAS NMR spectra, suggesting that sorbic acid molecules are in close proximity with the membrane/aqueous surface. No significant 2 H quadrupolar splitting (Δν Q ) changes are observed in the 2 H NMR spectra of DMPC‐ d 54 upon titration of sorbic acid, and the change of pH has a slight effect on Δν Q , indicating that sorbic acid has weak influence on the orientation order of the DMPC acyl chains in the fluid phase over the pH range from 3.0 to 7.4. This finding is in contrast to the results of the decanoic acid/DMPC‐ d 54 systems, where Δν Q increases as the concentration of decanoic acid increases. Thus, in the membrane association process, sorbic acids are most likely interacting with the headgroups and shallowly embedded near the top of the phospholipid headgroups, rather than inserting deep into the acyl chains. Thus, antimicrobial mode of action for sorbic acid may be different from that of long‐chain fatty acids. Copyright © 2009 John Wiley & Sons, Ltd.