References
- 1. P. Knekt, R. Jarvinen, A. Reunanen and J. Maatela, Flavonoid intake and coronary mortality in Finland: a cohort study, Brit. Med. J.312 (1996) 478–481; https://doi.org/10.1136/bmj.312.7029.478
- 2. M. L. McCullough, J. J. Peterson, R. Patel, P. F. Jacques, R. Shah and J. T. Dwyer, Flavonoid intake and cardiovascular disease mortality in a prospective cohort of US adults, Am. J. Clin. Nutr.95 (2012) 454–464; https://doi.org/10.3945/ajcn.111.016634
- 3. M. L. Liang, X. W. Da, A. D. He, G. Q. Yao, W. Xie, G. Liu, J. Z. Xiang and Z. Y. Ming, Pentamethylquercetin (PMQ) reduces thrombus formation by inhibiting platelet function, Sci. Rep.5 (2015) 11142 (11 pages); https://doi.org/10.1038/srep11142
- 4. Y. Wang, J. Tang, H. Zhu, X. Jiang, J. Liu, W. Xu, H. Ma, Q. Feng, J. Wu, M. Zhao and S. Peng, Aqueous extract of Rabdosia rubescens leaves: forming nanoparticles, targeting P-selectin, and inhibiting thrombosis, Int. J. Nanomed.10 (2015) 6905–6918; https://doi.org/10.2147/IJN.S91316
- 5. S. Vaiyapuri, H. Roweth, M. S. Ali, A. J. Unsworth, A. R. Stainer, G. D. Flora, M. Crescente, C. I. Jones, L. A. Moraes and J. M. Gibbins, Pharmacological actions of nobiletin in the modulation of platelet function, Br. J. Pharmacol. 172 (2015) 4133–4145; https://doi.org/10.1111/bph.13191
- 6. E. S. Park, Y. Lim, S. H. Lee, B. M. Kwon, H. S. Yoo, J. T. Hong and Y. P. Yun, Antiplatelet activity of obovatol, a biphenolic component of Magnolia obovata, in rat arterial thrombosis and rabbit platelet aggregation, J. Atheroscler. Thromb. 18 (2011) 659–669; https://doi.org/10.5551/jat.7427
- 7. Y. R. Jin, X. H. Han, Y. H. Zhang, J. J. Lee, Y. Lim, J. H. Chung and Y. P. Yun, Antiplatelet activity of hesperetin, a bioflavonoid, is mainly mediated by inhibition of PLC-gamma2 phosphorylation and cyclooxygenase-1 activity, Atherosclerosis194 (2007) 144–152; https://doi.org/10.1016/j.atherosclerosis.2006.10.011
- 8. P. Pignatelli, F. M. Pulcinelli, A. Celestini, L. Lenti, A. Ghiselli, P. P. Gazzaniga and F. Violi, The flavonoids quercetin and catechin synergistically inhibit platelet function by antagonizing the intracellular production of hydrogen peroxide, Am. J. Clin. Nutr. 72 (2000) 1150–1155; https://doi.org/10.1093/ajcn/72.5.1150
- 9. A. B. Hendrich, Flavonoid-membrane interactions: possible consequences for biological effects of some polyphenolic compounds, Acta. Pharmacol. Sin. 27 (2006) 27–40; https://doi.org/10.1111/j.1745-7254.2006.00238.x
- 10. P. I. Oteiza, A. G. Erlejman, S. V. Verstraeten, C. L. Keen and C. G. Fraga, Flavonoid-membrane interactions: a protective role of flavonoids at the membrane surface? Clin. Dev. Immunol. 12 (2005) 19–25; https://doi.org/10.1080/10446670410001722168
- 11. T. Lhermusier, H. Chap and B. Payrastre, Platelet membrane phospholipid asymmetry: from the characterization of a scramblase activity to the identification of an essential protein mutated in Scott syndrome, J. Thromb. Haemost. 9 (2011) 1883–1891; https://doi.org/10.1111/j.1538-7836.2011.04478.x
- 12. C. A. Lipinski, F. Lombardo, B. W. Dominy and P. J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev. 46 (2001) 3–26; https://doi.org/10.1016/S0169-409X(00)00129-0
- 13. G. L. Biagi, A. M. Barbaro, O. Gandolfi, M. C. Guerra and G. Cantelli-Forti, Rm values of steroids as an expression of their lipophilic character in structure-activity studies, J. Med. Chem. 18 (1975) 873–883; https://doi.org/10.1021/jm00243a003
- 14. E. Kłosińska-Szmurło, F. A. Pluciński, M. Grudzień, K. Betlejewska-Kielak, J. Biernacka and A. P. Mazurek, Experimental and theoretical studies on the molecular properties of ciprofloxacin, norfloxacin, pefloxacin, sparfloxacin, and gatifloxacin in determining bioavailability, J. Biol. Phys.40 (2014) 335–345; https://doi.org/10.1007/s10867-014-9354-z
- 15. B. J. Bennion, N. A. Be, M. W. McNerney, V. Lao, E. M. Carlson, C. A. Valdez, M. A. Malfatti, H. A. Enright, T. H. Nguyen, F. C. Lightstone and T. S. Carpenter, Predicting a drug’s membrane permeability: A computational model validated with in vitro permeability assay data, J. Phys. Chem. B.121 (2017) 5228–5237; https://doi.org/10.1021/acs.jpcb.7b02914
- 16. A. Daina, O. Michielin and V. Zoete, SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Sci. Rep. 7 (2017) 42717 (13 pages); https://doi.org/10.1038/srep42717
- 17. M. Bojić, Ž. Debeljak, M. Tomičić, M. Medić-Šarić and S. Tomić, Evaluation of antiaggregatory activity of flavonoid aglycone series, Nutrition J. 10 (2011) 73 (8 pages); https://doi.org/10.1186/1475-2891-10-73
- 18. A. Brocchieri, L. Pacchiarini, A. Saporiti and G. Grignani, In vitro effect of verapamil on platelet activation induced by ADP, collagen or thrombin, Platelets6 (1995) 195–199; https://doi.org/10.3109/09537109509078454
- 19. S. A. Saeed, H. Rasheed, F. A. Fecto, M. I. Achakzai, R. Ali, J. D. Connor and A. U. Gilani, Signalling mechanisms mediated by G-protein coupled receptors in human platelets, Acta Pharmacol. Sin. 25 (2004) 887–889.
- 20. J. W. Heemskerk, R. W. Farndale and S. O. Sage, Effects of U73122 and U73343 on human platelet calcium signalling and protein tyrosine phosphorylation, Biochim. Biophys. Acta1355 (1997) 81–88; https://doi.org/10.1016/S0167-4889(96)00113-9
- 21. T. Wu, M. He, X. Zang, X. Zhou, T. Qiu, S. Pan and X. Xu, A structure-activity relationship study of flavonoids as inhibitors of E. coli by membrane interaction effect, Biochim. Biophys. Acta1828 (2013) 2751–2756; https://doi.org/10.1016/j.bbamem.2013.07.029
- 22. M. Shichijo, N. Yamamoto, H. Tsujishita, M. Kimata, H. Nagai and T. Kokubo, Inhibition of syk activity and degranulation of human mast cells by flavonoids, Biol. Pharm. Bull. 26 (2003) 1685–1690; https://doi.org/10.1248/bpb.26.1685
- 23. A. Oliveira Filho, H. M. Fernandes, T. J. C. Assis, D. R. Meireles, O. Edeltrudes, E. Lima and H. L. F. Pêssoa, Pharmacological and toxicological analysis of flavonoid 5,7,4’-trimethoxyflavone: An in silico approach, IJPPR7 (2015) 431–434.
- 24. C. van Dijk, A. J. Driessen and K. Recourt, The uncoupling efficiency and affinity of flavonoids for vesicles, Biochem. Pharmacol. 60 (2000) 1593–1600; https://doi.org/10.1016/S0006-2952(00)00488-3
- 25. A. Arora, T. M. Byrem, M. G. Nair and G. M. Strasburg, Modulation of liposomal membrane fluidity by flavonoids and isoflavonoids, Arch. Biochem. Biophys. 373 (2000) 102–109; https://doi.org/10.1006/abbi.1999.1525
- 26. S. Kitagawa, M. Orinaka and H. Hirata, Depth-dependent change in membrane fluidity by phenolic compounds in bovine platelets and its relationship with their effects on aggregation and adenylate cyclase activity, Biochim. Biophys. Acta1179 (1993) 277–282; https://doi.org/10.1016/0167-4889(93)90083-2
- 27. N. Vlasic, M. S. Medow, S. M. Schwarz, K. A. Pritchard and M. B. Stemerman, Lipid fluidity modulates platelet aggregation and agglutination in vitro, Life Sci.53 (1993) 1053–1060; https://doi.org/10.1016/0024-3205(93)90258-5
- 28. K. Yoshida, S. Nagatoishi, D. Kuroda, N. Suzuki, T. Murata and K. Tsumoto, Phospholipid membrane fluidity alters ligand binding activity of a G protein-coupled receptor by shifting the conformational equilibrium, Biochemistry58 (2019) 504–508; https://doi.org/10.1021/acs.biochem.8b01194 (in press)
- 29. M. Bojić, Ž. Debeljak, M. Medić-Šarić and M. Tomičić, Interference of selected flavonoid aglycons in platelet aggregation assay, Clin. Chem. Lab. Med.50 (2012) 1403–1408; https://doi.org/10.1515/cclm-2011-0960
- 30. L. M. Ostertag, N. O’Kennedy, G. W. Horgan, P. A. Kroon, G. G. Duthie and B. de Roos, In vitro anti-platelet effects of simple plant-derived phenolic compounds are only found at high, non-physiological concentrations, Mol. Nutr. Food Res. 55 (2011) 1624–1636; https://doi.org/10.1002/mnfr.201100135
- 31. S. Vaiyapuri, M. S. Ali, L. A. Moraes, T. Sage, K. R. Lewis, C. I. Jones and J. M. Gibbins, Tangeretin regulates platelet function through inhibition of phosphoinositide 3-kinase and cyclic nucleotide signalling, Arterioscler. Thromb. Vasc. Biol. 33 (2013) 2740–2749; https://doi.org/10.1161/ATVBAHA.113.301988
- 32. T. Gremmel, R. Koppensteiner and S. Panzer, Comparison of aggregometry with flow cytometry for the assessment of agonists’-induced platelet reactivity in patients on dual antiplatelet therapy, PLoS One10 (2015) e0129666 (13 pages); https://doi.org/10.1371/journal.pone.0129666
- 33. K. Koltai, G. Kesmarky, G. Feher, A. Tibold and K. Toth, Platelet aggregometry testing: Molecular mechanisms, techniques and clinical implications, Int. J. Mol. Sci.18 (2017) 1803 (21 pages); https://doi.org/10.3390/ijms18081803