Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques
Bitterness often associated with whole wheat products may be related to phenolics in the bran. Cyclodextrins (CDs) are known to form inclusion complexes. The objective was to form inclusion complexes between <i>β</i>-CD and wheat phenolics. Pure phenolic acids (trans-ferulic acid (FA), c...
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MDPI AG
2020-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/18/4275 |
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| author | Tuba Simsek Bakhtiyor Rasulev Christian Mayer Senay Simsek |
| author_facet | Tuba Simsek Bakhtiyor Rasulev Christian Mayer Senay Simsek |
| author_sort | Tuba Simsek |
| collection | DOAJ |
| description | Bitterness often associated with whole wheat products may be related to phenolics in the bran. Cyclodextrins (CDs) are known to form inclusion complexes. The objective was to form inclusion complexes between <i>β</i>-CD and wheat phenolics. Pure phenolic acids (trans-ferulic acid (FA), caffeic acid (CA), and <i>p</i>-coumaric acid (CO)) and phenolic acids from wheat bran were used to investigate complex formation potential. Complexes were characterized by spectroscopy techniques, and a computational and molecular modeling study was carried out. The relative amount of complex formation between <i>β</i>-CD and wheat bran extract was CA > CO > FA. The phenolic compounds formed inclusion complexes with <i>β</i>-CDs by non-covalent bonds. The quantum-mechanical calculations supported the experimental results. The most stable complex was CO/<i>β</i>-CD complex. The Δ<i>H</i> value for CO/<i>β</i>-CD complex was −11.72 kcal/mol and was about 3 kcal/mol more stable than the other complexes. The QSPR model showed good correlation between binding energy and <sup>1</sup>H NMR shift for the H<sup>5</sup> signal. This research shows that phenolics and <i>β</i>-CD inclusion complexes could be utilized to improve the perception of whole meal food products since inclusion complexes have the potential to mask the bitter flavor and enhance the stability of the phenolics in wheat bran. |
| first_indexed | 2024-03-10T16:14:53Z |
| format | Article |
| id | doaj.art-c71ec0524ff74356ae2d6834d2d9422b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T16:14:53Z |
| publishDate | 2020-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c71ec0524ff74356ae2d6834d2d9422b2023-11-20T14:11:58ZengMDPI AGMolecules1420-30492020-09-012518427510.3390/molecules25184275Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational TechniquesTuba Simsek0Bakhtiyor Rasulev1Christian Mayer2Senay Simsek3Department of Physical Chemistry, Duisburg-Essen University, Universitätsstr. 2, 45141 Essen, GermanyDepartment of Coatings and Polymeric Materials, North Dakota State University, Fargo, ND 58102, USADepartment of Physical Chemistry, Duisburg-Essen University, Universitätsstr. 2, 45141 Essen, GermanyDepartment of Plant Sciences, North Dakota State University, Fargo, ND 58102, USABitterness often associated with whole wheat products may be related to phenolics in the bran. Cyclodextrins (CDs) are known to form inclusion complexes. The objective was to form inclusion complexes between <i>β</i>-CD and wheat phenolics. Pure phenolic acids (trans-ferulic acid (FA), caffeic acid (CA), and <i>p</i>-coumaric acid (CO)) and phenolic acids from wheat bran were used to investigate complex formation potential. Complexes were characterized by spectroscopy techniques, and a computational and molecular modeling study was carried out. The relative amount of complex formation between <i>β</i>-CD and wheat bran extract was CA > CO > FA. The phenolic compounds formed inclusion complexes with <i>β</i>-CDs by non-covalent bonds. The quantum-mechanical calculations supported the experimental results. The most stable complex was CO/<i>β</i>-CD complex. The Δ<i>H</i> value for CO/<i>β</i>-CD complex was −11.72 kcal/mol and was about 3 kcal/mol more stable than the other complexes. The QSPR model showed good correlation between binding energy and <sup>1</sup>H NMR shift for the H<sup>5</sup> signal. This research shows that phenolics and <i>β</i>-CD inclusion complexes could be utilized to improve the perception of whole meal food products since inclusion complexes have the potential to mask the bitter flavor and enhance the stability of the phenolics in wheat bran.https://www.mdpi.com/1420-3049/25/18/4275cyclodextrinwheatphenolicsbioactive compoundsinclusion complexinteraction |
| spellingShingle | Tuba Simsek Bakhtiyor Rasulev Christian Mayer Senay Simsek Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques Molecules cyclodextrin wheat phenolics bioactive compounds inclusion complex interaction |
| title | Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques |
| title_full | Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques |
| title_fullStr | Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques |
| title_full_unstemmed | Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques |
| title_short | Preparation and Characterization of Inclusion Complexes of <i>β</i>-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques |
| title_sort | preparation and characterization of inclusion complexes of i β i cyclodextrin and phenolics from wheat bran by combination of experimental and computational techniques |
| topic | cyclodextrin wheat phenolics bioactive compounds inclusion complex interaction |
| url | https://www.mdpi.com/1420-3049/25/18/4275 |
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