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Molecules 2017, 22(8), 1317; doi:10.3390/molecules22081317

Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods

1
School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China
2
Shandong Institute of Environmental Science, Jinan 250012, China
3
Jinan Institute of Measurement and Testing, Jinan 250002, China
4
Department of Pharmacy, Shandong Provincial Hospital Affiliated to Shandong University, Jinan 250021, China
5
Faculty of Pharmaceutical Sciences, University of Iceland, Reykjavik 107, Iceland
*
Author to whom correspondence should be addressed.
Received: 6 July 2017 / Revised: 31 July 2017 / Accepted: 4 August 2017 / Published: 9 August 2017
(This article belongs to the Special Issue Natural Products: Anticancer Potential and Beyond)
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Abstract

Phytochemical investigation on the methanol extract of Woodwardia unigemmata resulted in the isolation of seven flavonoids, including one new flavonol acylglycoside (1). The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis and comparison of literature data. The multidrug resistance (MDR) reversing activity was evaluated for the isolated compounds using doxorubicin-resistant K562/A02 cells model. Compound 6 showed comparable MDR reversing effect to verapamil. Furthermore, the interaction between compounds and bovine serum albumin (BSA) was investigated by spectroscopic methods, including steady-state fluorescence, synchronous fluorescence, circular dichroism (CD) spectroscopies, and molecular docking approach. The experimental results indicated that the seven flavonoids bind to BSA by static quenching mechanisms. The negative ΔH and ΔS values indicated that van der Waals interactions and hydrogen bonds contributed in the binding of compounds 26 to BSA. In the case of compounds 1 and 7 systems, the hydrophobic interactions play a major role. The binding of compounds to BSA causes slight changes in the secondary structure of BSA. There are two binding sites of compound 6 on BSA and site I is the main site according to the molecular docking studies and the site marker competitive binding assay. View Full-Text
Keywords: Woodwardia unigemmata; multidrug resistance; doxorubicin-resistant K562/A02 cells; bovine serum albumin; molecular docking Woodwardia unigemmata; multidrug resistance; doxorubicin-resistant K562/A02 cells; bovine serum albumin; molecular docking
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ma, R.; Pan, H.; Shen, T.; Li, P.; Chen, Y.; Li, Z.; Di, X.; Wang, S. Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods. Molecules 2017, 22, 1317.

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