Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups

Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups

Proton NMR signals of the phenolic hydroxyl groups of the substituted catechins were successfully collected. The identities of these signals were elucidated and confirmed by a combination of computational and experimental investigations including GIAO-B3LYP NMR chemical shift calculation, kinetic an...

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Main Authors: Shan Hong, Shanshan Wu, He Cai, Yimin Wang, Songbai Liu
Format: Article
Language:English
Published: Elsevier 2017-10-01
Series:Journal of Functional Foods
Subjects:
Catechin
Chemical shift
Quantum chemical computation
Substitution pattern
Structure elucidation
Online Access:http://www.sciencedirect.com/science/article/pii/S1756464617304243
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spelling doaj-6d7da0cbcb6844e2b3a367afed219fb12021-04-30T07:11:15ZengElsevierJournal of Functional Foods1756-46462017-10-01375865Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groupsShan Hong0Shanshan Wu1He Cai2Yimin Wang3Songbai Liu4Department of Food Science and Nutrition, Fuli Institute of Food Science, Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, China; Dept. of Food Science and Technology, The University of Tennessee, 2510 River Drive, Knoxville, TN 37996-4539, USADepartment of Food Science and Nutrition, Fuli Institute of Food Science, Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, ChinaDepartment of Food Science and Nutrition, Fuli Institute of Food Science, Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, ChinaCherry L. Emerson Center for Scientific Computation and Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USADepartment of Food Science and Nutrition, Fuli Institute of Food Science, Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, China; Corresponding author.Proton NMR signals of the phenolic hydroxyl groups of the substituted catechins were successfully collected. The identities of these signals were elucidated and confirmed by a combination of computational and experimental investigations including GIAO-B3LYP NMR chemical shift calculation, kinetic analysis of acylation, and NOESY correlation. Furthermore, the reliability of chemical shifts of hydrogens of phenolic hydroxyl groups was confirmed by evaluation of the influence of acidic, basic and water residues. Finally, the chemical shift profiles of phenolic hydroxyl groups were developed for instant structural recognition. This study demonstrated the feasibility of application of chemical shifts of hydrogens of phenolic hydroxyl groups as fingerprint for structural determination and the concept could be extended to other polyphenols.http://www.sciencedirect.com/science/article/pii/S1756464617304243CatechinChemical shiftQuantum chemical computationSubstitution patternStructure elucidation
collection DOAJ
language English
format Article
sources DOAJ
author Shan Hong
Shanshan Wu
He Cai
Yimin Wang
Songbai Liu
spellingShingle Shan Hong
Shanshan Wu
He Cai
Yimin Wang
Songbai Liu
Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups
Journal of Functional Foods
Catechin
Chemical shift
Quantum chemical computation
Substitution pattern
Structure elucidation
author_facet Shan Hong
Shanshan Wu
He Cai
Yimin Wang
Songbai Liu
author_sort Shan Hong
title Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups
title_short Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups
title_full Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups
title_fullStr Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups
title_full_unstemmed Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups
title_sort instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups
publisher Elsevier
series Journal of Functional Foods
issn 1756-4646
publishDate 2017-10-01
description Proton NMR signals of the phenolic hydroxyl groups of the substituted catechins were successfully collected. The identities of these signals were elucidated and confirmed by a combination of computational and experimental investigations including GIAO-B3LYP NMR chemical shift calculation, kinetic analysis of acylation, and NOESY correlation. Furthermore, the reliability of chemical shifts of hydrogens of phenolic hydroxyl groups was confirmed by evaluation of the influence of acidic, basic and water residues. Finally, the chemical shift profiles of phenolic hydroxyl groups were developed for instant structural recognition. This study demonstrated the feasibility of application of chemical shifts of hydrogens of phenolic hydroxyl groups as fingerprint for structural determination and the concept could be extended to other polyphenols.
topic Catechin
Chemical shift
Quantum chemical computation
Substitution pattern
Structure elucidation
url http://www.sciencedirect.com/science/article/pii/S1756464617304243
work_keys_str_mv AT shanhong instantstructureprofilingofsubstitutedcatechinsbychemicalshiftfingerprintofhydrogensofphenolichydroxylgroups
AT shanshanwu instantstructureprofilingofsubstitutedcatechinsbychemicalshiftfingerprintofhydrogensofphenolichydroxylgroups
AT hecai instantstructureprofilingofsubstitutedcatechinsbychemicalshiftfingerprintofhydrogensofphenolichydroxylgroups
AT yiminwang instantstructureprofilingofsubstitutedcatechinsbychemicalshiftfingerprintofhydrogensofphenolichydroxylgroups
AT songbailiu instantstructureprofilingofsubstitutedcatechinsbychemicalshiftfingerprintofhydrogensofphenolichydroxylgroups
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