Elucidating the interaction mechanism of eriocitrin with β-casein by multi-spectroscopic and molecular simulation methods

Cao, Xiangyu; He, Yonglin; Kong, Yuchi; Mei, Xueying; Huo, Yapeng; Yin, He; Liu, Jianli

doi:10.1016/j.foodhyd.2019.03.006

Cited by 80 publications

(34 citation statements)

References 40 publications

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“…The structures of α S1 -casein and β-casein were predicted using the I-TASSER protein structure server (). Out of the five predicted models by I-TASSER of the submitted sequence, the α S1 -casein and β-casein models with the highest confidence score of −4.87 and −4.56 were chosen to carry out further docking [24]. The three dimensional structure files of galangin and genistein were also retrieved from the NCBI database of PubChem in SDF file format.…”

Section: Methodsmentioning

confidence: 99%

The Non-Covalent Interactions and In Vitro Radical Scavenging Activities of the Caseinate-Galangin and Caseinate-Genistein Complexes

Zhao

2019

Antioxidants

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Non-covalent interactions and in vitro radical scavenging activities of the complexes formed by the commercial milk protein product caseinate and one of the two polyphenols (galangin and genistein) were assessed by the multi-spectroscopic techniques, molecular docking, and detection of scavenging activities against the 1,1–diphenyl-2-picryl-hydrazyl (DPPH), 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and hydroxyl radicals. The caseinate bound with the two polyphenols showed conformational changes and increased scavenging activities, compared with original caseinate. The caseinate-polyphenol binding was driven by the hydrophobic interaction and hydrogen-bonds, while hydrophobic interaction was the main binding force. Meanwhile, sodium dodecyl sulfate and urea could damage the essential hydrophobic interaction and hydrogen-bonds, respectively, and thus led to decreased apparent binding constants for the caseinate-polyphenol binding. Based on the measured values of several apparent thermodynamic parameters like ΔH, ΔS, ΔG, and donor–acceptor distance as well as the detected radical scavenging activity, galangin having more planar stereochemical structure and random B-ring rotation always had higher affinity for caseinate than genistein having location isomerism and twisted stereochemical structure, while the caseinate-galangin complex showed higher radical scavenging activity than the caseinate-genistein complex. It is thus concluded that both chemical and stereochemical structures of polyphenols are crucial to the affinity of polyphenols for protein and antioxidant activities of the protein-polyphenol complexes.

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Section: Methodsmentioning

confidence: 99%

The Non-Covalent Interactions and In Vitro Radical Scavenging Activities of the Caseinate-Galangin and Caseinate-Genistein Complexes

Zhao

2019

Antioxidants

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“…Moreover, different flavanones showed antiproliferative and apoptotic activities (Abd El-Hafeez et al, 2019;Koosha et al, 2019). Specifically, hesperidin and eriocitrin are known as anti-cancer agents (Birsu Cincin et al, 2015;Julius et al, 2017;Cao et al, 2019). Recently, hesperidin was found able to potentiate, along with two other natural compounds, the effect of tamoxifen against the breast tumour (Khamis et al, 2018) while eriocitrin to reduce the incidence of oral squamous cell carcinoma induced in hamsters (Baldasquin-Caceres et al, 2014).…”

Section: Discussionmentioning

confidence: 99%

Anticancer Effects of Wild Mountain Mentha longifolia Extract in Adrenocortical Tumor Cell Models

et al. 2020

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Mint [Mentha longifolia (L.) Hudson] is an aromatic plant that belongs to Lamiaceae family. It is traditionally used as herbal tea in Europe, Australia and North Africa and shows numerous pharmacological effects, such as spasmolytic, antioxidant, antimicrobial and anti-hemolytic. Recently, its antiproliferative role has been suggested in a small number of tumor cell models, but no data are available on adrenocortical carcinoma, a malignancy with a survival rate at 5 years of 20%-30% which frequently metastasize. This work aimed to study the effects of Mentha longifolia L. crude extract (ME) on two adrenocortical tumor cell models (H295R and SW13 cells). Chemical composition of ME was assessed by gaschromatography/mass spectrometry and NMR spectroscopy analysis. Brine shrimp lethality assay showed ME effects at >0.5 µg/µl (p < 0.05). Cell viability and vitality were determined by MTT, SRB, and trypan blue assays in H295R and SW13 cells. The antiproliferative effects of ME were more evident in SW13 cells at 72 h (ME > 0.5 µg/µl, p < 0.05). Combination of ME with mitotane (approved drug for adrenocortical carcinoma) seemed not to reinforce the efficacy of the herb. As control, human fibroblasts were treated with ME with no effect on cell viability. Clonogenic assay was concordant with previous cell viability tests (ME > 0.5 µg/µl, p < 0.05), while Wright staining demonstrated the presence of both necrotic and apoptotic cells. Cell cycle analysis showed a strong increase in subG0/G1 phase, related to cell death. Furthermore, MAPK and PI3k/Akt pathways were modulated by Western blot analysis when treating cells with ME alone or combined with mitotane. The crude methanolic extract of wild mountain mint can decrease cell viability, vitality and survival of adrenocortical tumor cell models, in particular of SW13 cells. These data show the potential anticancer effects of ME, still more work is needed to corroborate these findings.FIGURE 7 | Representative Western blot analysis for SW13 and H295R cells. Lines 1 and 5: untreated control. Lines 2 and 6: 0.5 mg/ml ME. Lines 3 and 7: mitotane 10 mM. Lines 4 and 8: ME 0.5 mg/ml + mitotane 10 mM. Experiments performed in triplicate.Patti et al.

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“…Compared with other delivery vehicles, casein self‐assembly has the following advantages: firstly, low toxicity and high safety; secondly, the prepared nanomicelles have high stability and targeted delivery of active ingredients in the inner environment; thirdly, nanomicelles can prolong the residence time of the carrier and promote the absorption of drugs [23]. Therefore, casein micelles can be exploited as a natural delivery vehicle for various hydrophobic compounds such as quercetin [24], eriocitrin [25], curcumin [26, 27], Glimepiride [28], (−)‐epigallocatechin gallate [29].…”

Section: Introductionmentioning

confidence: 99%

Method for enhancing bioavailability of myricetin based on self‐assembly of casein–myricetin nanomicelles

Guo

Chen

Tang

et al. 2020

IET nanobiotechnol.

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In order to expand the application in the medical field and enhance pharmacological effects, casein-myricetin nanomicelles were prepared by the self-assembly method and characterised by ultraviolet-visible spectroscopy and Fourier transform infrared spectroscopy. The parameters in self-assembly were optimised according to the factors of particle size, encapsulation yield, and drug loading. The result showed a pH of 5.5, a casein concentration of 2 mg/ml, a mass ratio of casein to myricetin of 8:1, ultrasonic power of 300 W, ultrasonic time of 5 min and ethanol volume of 7 ml were the optimal conditions. The situ cycle intestinal perfusion methods indicated that casein-myricetin nanomicelles can be more easily absorbed by small intestine than myricetin standard sample. Therefore, casein micelles are effective for improving the water solubility of myricetin.

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Elucidating the interaction mechanism of eriocitrin with β-casein by multi-spectroscopic and molecular simulation methods

Cited by 80 publications

References 40 publications

The Non-Covalent Interactions and In Vitro Radical Scavenging Activities of the Caseinate-Galangin and Caseinate-Genistein Complexes

The Non-Covalent Interactions and In Vitro Radical Scavenging Activities of the Caseinate-Galangin and Caseinate-Genistein Complexes

Anticancer Effects of Wild Mountain Mentha longifolia Extract in Adrenocortical Tumor Cell Models

Method for enhancing bioavailability of myricetin based on self‐assembly of casein–myricetin nanomicelles

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