Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods
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 da...
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MDPI AG
2017-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/8/1317 |
| _version_ | 1818538693988712448 |
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| author | Rui Ma Hong Pan Tao Shen Peng Li Yanan Chen Zhenyu Li Xiaxia Di Shuqi Wang |
| author_facet | Rui Ma Hong Pan Tao Shen Peng Li Yanan Chen Zhenyu Li Xiaxia Di Shuqi Wang |
| author_sort | Rui Ma |
| collection | DOAJ |
| description | 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 2–6 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. |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T21:32:15Z |
| publishDate | 2017-08-01 |
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| series | Molecules |
| spelling | doaj.art-7efe75466d9b44e3bf5aa7f4b98fecc02022-12-22T00:50:07ZengMDPI AGMolecules1420-30492017-08-01228131710.3390/molecules22081317molecules22081317Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling MethodsRui Ma0Hong Pan1Tao Shen2Peng Li3Yanan Chen4Zhenyu Li5Xiaxia Di6Shuqi Wang7School of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaSchool of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaSchool of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaShandong Institute of Environmental Science, Jinan 250012, ChinaJinan Institute of Measurement and Testing, Jinan 250002, ChinaDepartment of Pharmacy, Shandong Provincial Hospital Affiliated to Shandong University, Jinan 250021, ChinaFaculty of Pharmaceutical Sciences, University of Iceland, Reykjavik 107, IcelandSchool of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaPhytochemical 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 2–6 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.https://www.mdpi.com/1420-3049/22/8/1317Woodwardia unigemmatamultidrug resistancedoxorubicin-resistant K562/A02 cellsbovine serum albuminmolecular docking |
| spellingShingle | Rui Ma Hong Pan Tao Shen Peng Li Yanan Chen Zhenyu Li Xiaxia Di Shuqi Wang Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods Molecules Woodwardia unigemmata multidrug resistance doxorubicin-resistant K562/A02 cells bovine serum albumin molecular docking |
| title | Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods |
| title_full | Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods |
| title_fullStr | Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods |
| title_full_unstemmed | Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods |
| title_short | Interaction of Flavonoids from Woodwardia unigemmata with Bovine Serum Albumin (BSA): Application of Spectroscopic Techniques and Molecular Modeling Methods |
| title_sort | interaction of flavonoids from woodwardia unigemmata with bovine serum albumin bsa application of spectroscopic techniques and molecular modeling methods |
| topic | Woodwardia unigemmata multidrug resistance doxorubicin-resistant K562/A02 cells bovine serum albumin molecular docking |
| url | https://www.mdpi.com/1420-3049/22/8/1317 |
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