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Molecules 2016, 21(4), 372; doi:10.3390/molecules21040372

NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones

1
School of Food and Chemical Engineering, Beijing Engineering and Technology Research Center of Food Additives, Beijing Higher Institution Engineering Research Center of food additives and Ingredients, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing 100048, China
2
Department of Chemistry and Biotechnology, Uppsala BioCenter, Swedish University of Agricultural Sciences, P. O. Box 7015, Uppsala SE-750 07, Sweden
3
College of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, China
*
Author to whom correspondence should be addressed.
Academic Editor: Isabel C. F. R. Ferreira
Received: 29 January 2016 / Revised: 11 March 2016 / Accepted: 11 March 2016 / Published: 28 March 2016
(This article belongs to the Collection Bioactive Compounds)
View Full-Text   |   Download PDF [2148 KB, uploaded 29 March 2016]   |  

Abstract

The structure of the inclusion complexes of β-cyclodextrin (β-CD) with daidzein and daidzin in D2O were investigated using NMR spectroscopy. For the β-CD and daidzein system, two types of 1:1 complexes were formed with the daidzein deeply inserted into the CD cavity with different orientations. For the β-CD/daidzin system, a 1:1 complex was formed with the flavonoid part of daidzin entering the CD cavity from the wide rim. The inclusion complexes determined by NMR were constructed using molecular docking. Furthermore, the mixture of puerarin, daidzein and daidzin, which are the major isoflavonoid components present in Radix puerariae, was analyzed by diffusion-ordered spectroscopy (DOSY) alone and upon addition of β-CD in order to mimic chromatographic conditions and compare their binding affinities. View Full-Text
Keywords: β-cyclodextrin; flavonoids; NMR; interaction β-cyclodextrin; flavonoids; NMR; interaction
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Zhao, R.; Sandström, C.; Zhang, H.; Tan, T. NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones. Molecules 2016, 21, 372.

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