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

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

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...

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Bibliographic Details
Main Authors: Rui Zhao, Corine Sandström, Haiyang Zhang, Tianwei Tan
Format: Article
Language:English
Published: MDPI AG 2016-03-01
Series:Molecules
Subjects:
β-cyclodextrin
flavonoids
NMR
interaction
Online Access:http://www.mdpi.com/1420-3049/21/4/372
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spelling doaj-1477db4d34214be8b8a56d97deb5729a2020-11-24T23:47:22ZengMDPI AGMolecules1420-30492016-03-0121437210.3390/molecules21040372molecules21040372NMR Study on the Inclusion Complexes of β-Cyclodextrin with IsoflavonesRui Zhao0Corine Sandström1Haiyang Zhang2Tianwei Tan3School 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, ChinaDepartment of Chemistry and Biotechnology, Uppsala BioCenter, Swedish University of Agricultural Sciences, P. O. Box 7015, Uppsala SE-750 07, SwedenCollege of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, ChinaCollege of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, ChinaThe 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.http://www.mdpi.com/1420-3049/21/4/372β-cyclodextrinflavonoidsNMRinteraction
collection DOAJ
language English
format Article
sources DOAJ
author Rui Zhao
Corine Sandström
Haiyang Zhang
Tianwei Tan
spellingShingle Rui Zhao
Corine Sandström
Haiyang Zhang
Tianwei Tan
NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones
Molecules
β-cyclodextrin
flavonoids
NMR
interaction
author_facet Rui Zhao
Corine Sandström
Haiyang Zhang
Tianwei Tan
author_sort Rui Zhao
title NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones
title_short NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones
title_full NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones
title_fullStr NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones
title_full_unstemmed NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones
title_sort nmr study on the inclusion complexes of β-cyclodextrin with isoflavones
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2016-03-01
description 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.
topic β-cyclodextrin
flavonoids
NMR
interaction
url http://www.mdpi.com/1420-3049/21/4/372
work_keys_str_mv AT ruizhao nmrstudyontheinclusioncomplexesofbcyclodextrinwithisoflavones
AT corinesandstrom nmrstudyontheinclusioncomplexesofbcyclodextrinwithisoflavones
AT haiyangzhang nmrstudyontheinclusioncomplexesofbcyclodextrinwithisoflavones
AT tianweitan nmrstudyontheinclusioncomplexesofbcyclodextrinwithisoflavones
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