Combined spectroscopic, molecular docking and quantum mechanics study of β-casein and p-coumaric acid interactions following thermal treatment

Kaur, Jasmeet; Katopo, Lita; Hung, Andrew; Ashton, John; Kasapis, Stefan

doi:10.1016/j.foodchem.2018.01.091

Cited by 65 publications

(20 citation statements)

References 41 publications

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“…They are found in wine, vegetables, fruits, seeds, and sugarcane-sugar [25]. p -Coumaric acid is a phenolic secondary metabolite abundant in nature [26,27,28,29,30]. It is of great importance for presenting antioxidant, anti-inflammatory, anticancer, chemo-protectant, anti-diabetic, and antimicrobial properties [31].…”

Section: Introductionmentioning

confidence: 99%

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Lopes

Castillo

Monteiro

et al. 2019

IJMS

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Trypanosoma species are responsible for chronic and systemic infections in millions of people around the world, compromising life quality, and family and government budgets. This group of diseases is classified as neglected and causes thousands of deaths each year. In the present study, the trypanocidal effect of a set of 12 ester derivatives of the p-coumaric acid was tested. Of the test derivatives, pentyl p-coumarate (7) (5.16 ± 1.28 μM; 61.63 ± 28.59 μM) presented the best respective trypanocidal activities against both epimastigote and trypomastigote forms. Flow cytometry analysis revealed an increase in the percentage of 7-AAD labeled cells, an increase in reactive oxygen species, and a loss of mitochondrial membrane potential; indicating cell death by necrosis. This mechanism was confirmed by scanning electron microscopy, noting the loss of cellular integrity. Molecular docking data indicated that of the chemical compounds tested, compound 7 potentially acts through two mechanisms of action, whether by links with aldo-keto reductases (AKR) or by comprising cruzain (CZ) which is one of the key Trypanosoma cruzi development enzymes. The results indicate that for both enzymes, van der Waals interactions between ligand and receptors favor binding and hydrophobic interactions with the phenolic and aliphatic parts of the ligand. The study demonstrates that p-coumarate derivatives are promising molecules for developing new prototypes with antiprotozoal activity.

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Section: Introductionmentioning

confidence: 99%

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Lopes

Castillo

Monteiro

et al. 2019

IJMS

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“…In addition, the PVG levels upon incorporation of SMP and sucrose could feasibly be affected by the interaction between oxidized ferulic acid, forming a semi-quinone, and SMP leading to a reduction in the availability of ferulic acid (precursor of PVG) for the thermal decarboxylation process. Recently, Kaur et al. (2018) stated that in milk protein-phenolic acid solutions, heat treatment oxidized phenolic acids leading to the formation of covalent bonds between sulfhydryl or amino groups of the protein and quinones.…”

Section: Resultsmentioning

confidence: 99%

Shelf-life studies of flavour characteristics in model UHT liquid systems enriched with wholegrain oat

Alqahtani

Ashton

Katopo

et al. 2018

Heliyon

Self Cite

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Development of malodourous compounds, hexanal and p-vinyl guaiacol (PVG), in UHT model liquid systems fortified with wholegrain oat were evaluated. Single and mixed systems using oat powder (3, 5, and 7% w/w), skim milk powder (SMP, 2.8% w/w) and sucrose (6.7% w/w) were subjected to UHT treatment and 29 days ambient storage. Both chromatographic analyses and panellists' perceived aroma intensity show a positive relationship between the content of hexanal and PVG, storage time and oat concentrations trialled. Ratio of the odour activity values (OAV) plotted against time shows that although PVG aroma initially is dominant, hexanal aroma, with a ratio of about 0.5, has twice the intensity of the PVG aroma for the remaining 29 days. Oat samples (with skim milk) were unacceptable when hexanal concentration was 3–5 times its threshold whilst the PVG level was still below its threshold in the same samples.

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“…For static quenching, the value of the association constant (K a ) and the number of binding sites (n) were calculated by using the modified Stern–Volmer equation given below in the logarithmic form [ 53 ]:

…”

Section: Methodsmentioning

confidence: 99%

“…[Q] is the concentration of quencher; K q is the bimolecular quenching constant; and τ 0 is the lifetime of the fluorophore when the quencher is absent, and the value typically equals to 10 −8 s. For static quenching, the value of the association constant (K a ) and the number of binding sites (n) were calculated by using the modified Stern-Volmer equation given below in the logarithmic form [53]:…”

Section: Fluorescence Spectroscopymentioning

confidence: 99%

Elucidation of Interaction between Whey Proteins and Proanthocyanidins and Its Protective Effects on Proanthocyanidins during In-Vitro Digestion and Storage

2021

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Whey proteins and oligomeric proanthocyanidins have nutritional value and are widely used in combination as food supplements. However, the effect of the interactions between proanthocyanidins and whey proteins on their stability has not been studied in depth. In this work, we aimed to characterize the interactions between β-Lactoglobulin (β-LG) and α-lactalbumin (α-LA) and oligomeric proanthocyanidins, including A1, A2, B1, B2, B3, and C1, using multi-spectroscopic and molecular docking methods. Fluorescence spectroscopic data revealed that all of the oligomeric proanthocyanidins quenched the intrinsic fluorescence of β-LG or α-LA by binding-related fluorescence quenching. Among the six oligomeric proanthocyanidins, A1 showed the strongest affinity for β-LG (Ka = 2.951 (±0.447) × 104 L∙mol−1) and α-LA (Ka = 1.472 (±0.236) × 105 L∙mol−1) at 297 K. β-LG/α-LA and proanthocyanidins can spontaneously form complexes, which are mainly induced by hydrophobic interactions, hydrogen bonds, and van der Waals forces. Fourier-transform infrared spectroscopy (FTIR) and circular dichroism spectroscopy showed that the secondary structures of the proteins were rearranged after binding to oligomeric proanthocyanidins. During in vitro gastrointestinal digestion, the recovery rate of A1 and A2 increased with the addition of WPI by 11.90% and 38.43%, respectively. The addition of WPI (molar ratio of 1:1) increased the retention rate of proanthocyanidins A1, A2, B1, B2, B3, and C1 during storage at room temperature by 14.01%, 23.14%, 30.09%, 62.67%, 47.92%, and 60.56%, respectively. These results are helpful for the promotion of protein–proanthocyanidin complexes as functional food ingredients in the food industry.

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Combined spectroscopic, molecular docking and quantum mechanics study of β-casein and p-coumaric acid interactions following thermal treatment

Cited by 65 publications

References 41 publications

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Shelf-life studies of flavour characteristics in model UHT liquid systems enriched with wholegrain oat

Elucidation of Interaction between Whey Proteins and Proanthocyanidins and Its Protective Effects on Proanthocyanidins during In-Vitro Digestion and Storage

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