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Chemical exchange of hydroxyl protons in quercetin measured by pulsed field gradient NMR

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Abstract

The diffusion behavior of hydroxyl protons (OH) in quercetin in 100% DMSO-d6 (deuterium dimethylsulfoxide) and a 90% DMSO-d6 solution containing 10% H2O was investigated with 600 MHz 1H pulsed field gradient (PFG) nuclear magnetic resonance (NMR). Only resonances of the 5-hydroxyl protons (OH5) were well resolved in NMR spectra of quercetin for all solutions under study. This phenomenon is explained by the intramolecular hydrogen bonding between OH5 protons and the 4-carbonyl oxygen (CO4). During diffusion experiments, the OH5 protons showed a biexponential diffusion decay, indicating an exchange process with water. As water content in the solvents increased, the lifetime (τ q) of the OH5 protons decreased from 96.7±10.0 ms in 100% DMSO-d6 to 14.3±1.4 ms in the 90% DMSO-d6 solution containing 10% H2O, indicating an increase in the exchange rate (k q = l/τ q) of the OH5 protons. This study demonstrates that the diffusion approach with PFG-NMR is much faster and easier for estimating the short lifetime or fast exchange rate of hydroxyl protons in quercetin.

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Authors and Affiliations

  1. School of Life Science and Biotechnology, Korea University, Seoul, 136-701, Korea

    Y. -S. Hong & C. -H. Lee

  2. Magnetic Resonance Team, Korea Basic Science Institute, Cheongwon, Korea

    K. S. Hong & J. -H. Cho

  3. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Russian Federation

    V. I. Volkov

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  1. Y. -S. Hong
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  2. K. S. Hong
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  3. J. -H. Cho
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  5. C. -H. Lee
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Correspondence to C. -H. Lee.

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Hong, Y.S., Hong, K.S., Cho, J.H. et al. Chemical exchange of hydroxyl protons in quercetin measured by pulsed field gradient NMR. Appl Magn Reson 35, 261–270 (2009). https://doi.org/10.1007/s00723-008-0160-2

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