Structure-activity relationship study between baicalein and wogonin by spectrometry, molecular docking and microcalorimetry

Food Chemistry

Volumn 208, Issue , 2016, Pages 192-198

  Tu, Bao ^a   Li, Rong Rong ^a   Liu, Zhi Juan ^a   Chen, Zhi Feng ^a   Ouyang, Yu ^a   Hu, Yan Jun ^a  

^a HUBEI NORMAL UNIVERSITY   (China)

Author keywords

Antibacterial activity; Antioxidant activity; Baicalein; Structure activity relationship; Wogonin

Indexed keywords

ANTIOXIDANTS; BIOACTIVITY; CALORIMETERS; FLAVONOIDS; MOLECULAR MODELING; SPECTROMETRY; STRUCTURES (BUILT OBJECTS);

ANTI-BACTERIAL ACTIVITY; ANTI-OXIDANT ACTIVITIES; BAICALEIN; STRUCTURE ACTIVITY RELATIONSHIPS; WOGONIN;

CATALYST ACTIVITY;

AMINO ACID; BAICALEIN; BOVINE SERUM ALBUMIN; HYDROXYL GROUP; IBUPROFEN; WARFARIN; WOGONIN; ANTIINFECTIVE AGENT; ANTIOXIDANT; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; COMPARATIVE STUDY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DRUG MECHANISM; ESCHERICHIA COLI; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; MICROCALORIMETRY; MOLECULAR DOCKING; NONHUMAN; STATIC ELECTRICITY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; TEMPERATURE; CALORIMETRY; CHEMISTRY; DRUG EFFECTS; METABOLISM; MOLECULAR MODEL; PROCEDURES; PROTEIN CONFORMATION; SPECTROSCOPY;

ANTI-BACTERIAL AGENTS; ANTIOXIDANTS; CALORIMETRY; ESCHERICHIA COLI; FLAVANONES; FLAVONES; MODELS, MOLECULAR; MOLECULAR DOCKING SIMULATION; PROTEIN CONFORMATION; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84962859553     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2016.04.006     Document Type: Article

References (37)

1. L.E. Alcaraz, S.E. Blanco, O.N. Puig, F. Tomas, and F.H. Ferretti Antibacterial activity of flavonoids against methicillin-resistant Staphylococcus aureus strains Journal of Theoretical Biology 205 2000 231 240
2. M.S. Blois Antioxidants determination by the use of a stable free radical Nature 181 1958 1199 1200
3. L.S. Chen, W. Xu, R. Shao, and X.F. Du Bioactivities of phytochemicals in Araiostegia yunnanensis (Christ) Food Chemistry 186 2014 37 45
4. Y.H. Chen, Z.S. Yang, C.C. Wen, Y.S. Chang, B.C. Wang, C. Hsiao, and T. Shih Evaluation of the structure-activity relationship of flavonoids as antioxidants and toxicants of zebrafish larvae Food Chemistry 134 2012 717 724
5. V. Cheynier, F. Tomas-Barberan, and K. Yoshida Polyphenols: from plants to a variety of food and non-food uses Journal of Agricultural and Food Chemistry 63 2015 7589 7594
6. L.L. Dong, Y.J. Fu, Y.G. Zu, M. Luo, W. Wang, C.Y. Li, and P.S. Mu An enhanced preparation and purification of the major antioxidants baicalein and wogonin from Scutellariae radix Food Chemistry 133 2012 430 436
7. J. Feng, W. Xu, X. Tao, H. Wei, F. Cai, B. Jiang, and W.S. Chen Simultaneous determination of baicalin, baicalein, wogonin, berberine, palmatine and jatrorrhizine in rat plasma by liquid chromatography-tandem mass spectrometry and application in pharmacokinetic studies after oral administration of traditional Chinese medicinal preparations containing scutellaria-coptis herb couple Journal of Pharmaceutical and Biomedical Analysis 53 2010 591 598
8. E.F. Grant, D.C. Terry, G.S.S. Daryl, D.W. Lisa, and J.W.J. Michael Investigation of the differences in thermal stability of two recombinant human serum albumins with 1,2-Dipalmitoyl-snglycero-3-phosphocholine liposomes by UV circular dichroism spectropolarimetry Journal Physical Chemistry B 116 2012 4661 4670
9. W.J. Kong, Y.L. Zhao, X.H. Xiao, J.B. Wang, H.B. Li, and Z.L. Li Y. Liu Spectrum-effect relationships between ultra performance liquid chromatography fingerprints and anti-bacterial activities of Rhizoma coptidis Analytica Chimica Acta 634 2009 279 285
10. W.J. Kong, Y.L. Zhao, X.Y. Xing, X.P. Ma, X.J. Sun, M.H. Yang, and X.H. Xiao Antibacterial evaluation of flavonoid compounds against E. coli by microcalorimetry and chemometrics Applied Microbiology and Biotechnology 99 2015 6049 6058
11. D.H. Lee, T.H. Lee, C.H. Jung, and Y.H. Kim Wogonin induces apoptosis by activating the AMPK and p53 signaling pathways in human glioblastoma cells Cellular Signalling 24 2012 2216 2225
12. K.A. Majorek, P.J. Porebski, A. Dayal, M.D. Zimmerman, K. Jablonska, and A.J. Stewart W. Minor Structural and immunologic characterization of bovine, horse, and rabbit serum albumins Molecular Immunology 52 2012 174 182
13. R. Mi, X.T. Bai, B. Tu, and Y.J. Hu Unraveling the coptisine-ctDNA binding mechanism by multispectroscopic, electrochemical and molecular docking methods RSC Advances 5 2015 47367 47376
14. E. Moghaddam, B.T. Teoh, S.S. Sam, R. Lani, P. Hassandarvish, and Z. Chik K. Zandi Baicalin, a metabolite of baicalein with antiviral activity against dengue virus Scientific Reports 4 2014 5452
15. J.D. Nadpal, M.M. Lesjak, F.S. Sibul, G.T. Anackov, D.D. Cetojevic-Simin, N.M. Mimica-Dukic, and I.N. Beara Comparative study of biological activities and phytochemical composition of two rose hips and their preserves: Rosa canina L. and Rosa arvensis Huds Food Chemistry 192 2016 907 914
16. S. Naveenraj, and S. Anandan Binding of serum albumins with bioactive substances - Nanoparticles to drugs Journal of Photochemistry and Photobiology C 14 2013 53 71
17. L.P. Peng, S. Nagarajan, S. Rasheed, and C.H. Zhou Synthesis and biological evaluation of a new class of quinazolinone azoles as potential antimicrobial agents and their interactions with calf thymus DNA and human serum albumin MedChemCommun 6 2015 222 229
18. W. Peng, F. Ding, Y.T. Jiang, Y. Sun, and Y.K. Peng Evaluation of the biointeraction of colorant flavazin with human serum albumin: insights from multiple spectroscopic studies, in silico docking and molecular dynamics simulation Food & Function 5 2014 1203 1217
19. G. Polierl, M. Giaisi, R. Kohler, W.W. Muller, C. Lutz, and E. Buss M. Li-Weber Targeting CDK9 by wogonin and related natural flavones potentiates the anti-cancer efficacy of the Bcl-2 family inhibitor ABT-263 International Journal of Cancer 136 2015 688 698
20. N. Quijada-Morín, J.M. Hernández-Hierro, J.C. Rivas-Gonzalo, and M.T. Escribano-Bailón Extractability of low molecular mass flavanols and flavonols from red grape skins. Relationship to cell wall composition at different ripeness stages Journal of Agricultural and Food Chemistry 63 2015 7654 7662
21. P.D. Ross, and S. Subramanian Thermodynamics of protein association reactions: forces contributing to stability Biochemistry 20 1981 3096 3102
22. M. Singh, M. Kaur, and O. Silakari Flavones: an important scaffold for medicinal chemistry European Journal of Medicinal Chemistry 84 2014 206 239
23. Y.G. Song, Y.P. Liu, W.B. Liu, F.A. Villamenabc, and J.L. Zweier Characterization of the binding of the Finland trityl radical with bovine serum albumin RSC Advances 4 2014 47649 47656
24. G. Sudlow, D.J. Birkett, and D.N. Wade Further characterization of specific drug binding sites on human serum albumin Molecular Pharmacology 12 1976 1052 1061
25. B. Tu, Z.F. Chen, Z.J. Liu, L.Y. Cheng, and Y.J. Hu Interaction of flavones with DNA in vitro: structure-activity relationships RSC Advances 5 2015 33058 33066
26. B. Tu, Z.F. Chen, Z.J. Liu, R.R. Li, Y. Ouyang, and Y.J. Hu Study of the structure-activity relationship of flavonoids based on their interaction with human serum albumin RSC Advances 5 2015 73290 73300
27. B. Tu, Y. Wang, R. Mi, Y. Ouyang, and Y.J. Hu Evaluation of the interaction between naringenin and human serum albumin: insights from fluorescence spectroscopy, electrochemical measurement and molecular docking Spectrochimica Acta part A 149 2015 536 543
28. I. Vints, and S. Rozen Fluorination of flavones and chromones using elemental fluorine Journal of Organic Chemistry 79 2014 7261 7265
29. J. Wang, C. Xiang, F.F. Tian, Z.Q. Xu, F.L. Jiang, and Y. Liu Investigating the interactions of a novel anticancer delocalized lipophilic cation and its precursor compound with human serum albumin RSC Advances 4 2014 18205 18216
30. Y.J. Wang, E. Han, Q.H. Xing, J. Yan, A. Arrington, and C. Wang J.H. Yim Baicalein upregulates DDIT4 expression which mediates mTOR inhibition and growth inhibition in cancer cells Cancer Letters 358 2015 170 179
31. C.L. Xie, H.K. Tang, Z.H. Song, S.S. Qu, Y.T. Liao, and H.S. Liu Microcalorimetric study of bacterial growth Thermochimica Acta 123 1988 33 41
32. D. Yan, J.X. Li, Y. Xiong, C.E. Zhang, J.Y. Luo, and Y.M. Han X.H. Xiao Promotion of quality standard of herbal medicine by constituent removing and adding Scientific Reports 4 2013 3668
33. M.T. Yasuda, K. Fujita, T. Hosoya, S. Imai, and K. Shimoi Absorption and metabolism of luteolin and its glycosides from the extract of Chrysanthemum morifolium flowers in rats and Caco-2 cells Journal of Agricultural and Food Chemistry 63 2015 7693 7699
34. Y. Zhang, and Q.X. Zhong Probing the binding between norbixin and dairy proteins by spectroscopy methods Food Chemistry 139 2013 611 616
35. Y. Zhang, and Q.X. Zhong Effects of thermal denaturation on binding between bixin and whey protein Journal of Agricultural and Food Chemistry 60 2012 7526 7531
36. Y.L. Zhao, L. Jia, J.B. Wang, M. Gong, P. Zhang, and J.Y. Li X.H. Xiao Microcalorimetry with correspondence analysis for studying the antibacterial effect of ephedrine on Escherichia coli Thermochimica Acta 557 2013 50 54
37. Y.L. Zhao, J.B. Wang, X.J. Sun, L. Jia, J.Y. Li, and L.M. Shan X.H. Xiao Microcalorimetry coupled with chemometric techniques for toxicity evaluation of Radix Aconiti Lateralis Preparata (Fuzi) and its processed products on Escherichia coli Applied Microbiology and Biotechnology 98 2014 437 444