Journal
MOLECULES
Volume 25, Issue 18, Pages -Publisher
MDPI
DOI: 10.3390/molecules25184275
Keywords
cyclodextrin; wheat; phenolics; bioactive compounds; inclusion complex; interaction
Funding
- North Dakota State University
- Center for Computationally Assisted Science and Technology (CCAST)
- Department of Energy [DE-SC0001717]
- National Science Foundation through the ND EPSCoR Award [IIA-1355466]
- State of North Dakota
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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 beta-CD and wheat phenolics. Pure phenolic acids (trans-ferulic acid (FA), caffeic acid (CA), and p-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 beta-CD and wheat bran extract was CA > CO > FA. The phenolic compounds formed inclusion complexes with beta-CDs by non-covalent bonds. The quantum-mechanical calculations supported the experimental results. The most stable complex was CO/beta-CD complex. The Delta H value for CO/beta-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 H-1 NMR shift for the H-5 signal. This research shows that phenolics and beta-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.
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