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Stern-Volmer Plot (Dopac-BSA) A Comparative Study of the Binding Constants of Several Polyphenols with BSA and LDL-VLDL through Fluorescence Quenching: A Potential Tool in the Fight against Atherosclerosis A thesis presented to the faculty of the Chemistry Department of the University of Scranton as a prerequisite for the degree of Master of Arts in Biochemistry By: Dana Poloni Date: June 9, 2015 Table of Contents Table of Contents………………………………………………………………………...III List of Figures………………………………………………………………………….VIII List of Tables………………………………………………………………………..........X Acknowledgements………………………………………………………………………XI Abstract…………………………………………………………………………………XII 1.0 Introduction……………………………………………………………………………1 1.1 Phenolic acids: Benzoic Acids and their Derivatives…………………………5 1.2 Phenolic acids: Phenylacetic Acids and their Derivatives…………………...12 1.3 Phenolic acids: Cinnamic Acids and their Derivatives………………………15 1.4 Stilbenoids: Stilbenes………………………………………………………...25 1.5 Flavonoids: Flavones………………………………………………………...28 1.6 Flavonoids: Isoflavones……………………………………………………...30 1.7 Flavonoids: Flavonols………………………………………………………..32 1.8 Flavonoids: Anthocyanidins…………………………………………………34 1.9 Thesis Overview……………………………………………………………..35 2.0 Materials and Methods……………………………………………………………….41 2.1 Reagents……………………………………………………………………...41 2.2 Polyphenols…………………………………………………………………..41 2.3 Materials……………………………………………………………………..42 2.4 PBS Solution Preparation……………………………………………………43 2.5 Polyphenol Standards Preparation…………………………………………...44 2.6 BSA Standard Preparation…………………………………………………...44 2.7 Isolation of Porcine Plasma………………………………………………….44 2.8 Storage of Porcine Plasma…………………………………………………...45 2.9 LDL-VLDL Extraction Method……………………………………………...45 2.10 Column Regeneration………………………………………………………47 2.11.0 Bradford Method – Preparation of Coomassie Reagent………………….47 2.11.1 Stock Reagent…………………………………………………………….47 2.11.2 Assay Reagent…………………………………………………………….48 2.12 Quantitative Determination of Protein in LDL-VLDL from Porcine Plasma via Bradford Method……………………………………………………..48 2.13 FT-IR Spectroscopy………………………………………………………...50 2.14.0 Fluorescence Quenching Method………………………………………...51 2.14.1 Instrumentation and Parameters…………………………………………..51 2.14.2 Procedure…………………………………………………………………51 2.15 Statistical Analysis………………………………………………………….52 3.0 Binding Constant Calculations………………………………………………………53 3.1 Overview……………………………………………………………………..53 3.2 Stern-Volmer Plots…………………………………………………………...56 3.3 Double-Logarithm Plots……………………………………………………...58 3.4 Quadratic Equation…………………………………………………………..59 3.5 Scatchard’s Treatment……………………………………………………….60 3.6 Benesi-Hildebrand’s Treatment……………………………………………...62 4.0 Results and Discussion………………………………………………………………64 4.1 Determination of LDL-VLDL Plasma Source……………………………….64 4.2.0 Incorporation of Polyphenol into BSA and LDL-VLDL…………………..66 4.2.1 Bimolecular Rate Constants (kqs)……...…………………………………..66 4.2.2 Incorporation of Polyphenol into Protein/Lipoprotein via FT-IR………….68 4.3 Binding Constants (Kas).………………………………………………..……69 4.4.0 Correlation between Calculated Binding Constants and Other Theoretical/Calculated Properties and Factors…………………………..80 4.4.1 Polar Surface Area…………………………………………………………81 4.4.2 n (Hill-affinity/binding sites) ……………………………………………...81 4.4.2.1 Outlier- n Value of Ellagic acid, and KDL-BSA, All Polyphenols and PAs……………………………………………………………………….82 4.4.2.2 Outlier- n Value of p-Hydroxyphenylacetic acid, and KDL-LDL-VLDL, All Polyphenols and PAs………………………………………………...82 4.4.3 Hydrogen Bond Acceptors/Donors………………………………………...83 4.4.4 Log P (Partition Coefficient) and Log D (Distribution Coefficient)………83 4.4.5 Log P (Partition Coefficient) and Log D (Distribution Coefficient) vs Log Ka……………………………………………………………………85 4.5.0 Comparison between the Calculated Binding Constants of both the Stern- Volmer and Double-Logarithm Method, for BSA and LDL-VLDL, and the Structural Characteristics of a Given Polyphenol……………………86 4.5.1.0 Comparison of the Stilbenes Resveratrol and Pterostilbene……………..87 4.5.1.1 Resveratrol and Pterostilbene with BSA…………………………………87 4.5.1.2 Resveratrol and Pterostilbene with LDL-VLDL…………………………88 4.5.2.0 Comparison of the Flavonols Quercetin, Quercetin-3-glucuronide, and Quercetin-3-glucoside……………………………………………………89 4.5.2.1 Quercetin, Quercetin-3-glucuronide, and Quercetin-3-glucoside with BSA………………………………………………………………………90 4.5.2.2 Quercetin, Quercetin-3-glucuronide, and Quercetin-3-glucoside with LDL-VLDL………………………………………………………………91 4.5.3.0 Comparison of the Flavones Flavone, Chrysin, Baicalein, and Baicalin…………………………………………………………………..92 4.5.3.1 Flavone, Chrysin, Baicalein, and Baicalin with BSA……………………93 4.5.3.2 Flavone, Chrysin, Baicalein, and Baicalin with LDL-VLDL……………94 4.5.4.0 Comparison of the Phenylacetic acid Derivatives Dopac, m- Hydroxyphenylacetic acid, p-Hydroxyphenylacetic acid, and Homogentisic acid……………………………………………………….95 4.5.4.1 Phenylacetic acid Derivatives Dopac, m- Hydroxyphenylacetic acid, p- Hydroxyphenylacetic acid, and Homogentisic acid with BSA…………..96 4.5.4.2 Phenylacetic acid Derivatives Dopac, m- Hydroxyphenylacetic acid, p- Hydroxyphenylacetic acid, and Homogentisic acid with LDL-VLDL…..97 4.5.5.0 Comparison of the Benzoic acid Derivatives Gallic acid, p- Hydroxysalicylic acid, Protocatechuic acid, m-Hydroxybenzoic acid, and p-Hydroxybenzoic acid…………………………………………………..98 4.5.5.1 Benzoic acid Derivatives Gallic acid, p-Hydroxysalicylic acid, Protocatechuic acid, m-Hydroxybenzoic acid, and p-Hydroxybenzoic acid with BSA……………………………………………………………99 4.5.5.2 Benzoic acid Derivatives Gallic acid, p-Hydroxysalicylic acid, Protocatechuic acid, m-Hydroxybenzoic acid, and p-Hydroxybenzoic acid with LDL-VLDL…………………………………………………..100 4.5.6.0 Comparison of the Benzoic acid Derivatives Gallic acid, Eudesmic acid, Syringic acid, Vanillic acid, and Apocynin…………………………….102 4.5.6.1 Benzoic acid Derivatives Gallic acid, Eudesmic acid, Syringic acid, Vanillic acid, and Apocynin with BSA…………………………………102 4.5.6.2 Benzoic acid Derivatives Gallic acid, Eudesmic acid, Syringic acid, Vanillic acid, and Apocynin with LDL-VLDL…………………………103 4.5.7.0 Comparison of the Cinnamic acid Derivatives Chlorogenic acid, Caffeic acid, Caffeic acid-3-o-glucuronide, and Caffeic acid-4-o- glucuronide…………………………………………………………..…105 4.5.7.1 Cinnamic acid Derivatives Chlorogenic acid, Caffeic acid, Caffeic acid-3- o-glucuronide, and Caffeic acid-4-o-glucuronide with BSA…………...105 4.5.7.2 Cinnamic acid Derivatives Chlorogenic acid, Caffeic acid, Caffeic acid-3- o-glucuronide, and Caffeic acid-4-o-glucuronide with LDL-VLDL…...106 4.5.8.0 Comparison of the Cinnamic acid Derivatives Caffeic acid, Dihydrocaffeic acid, Dihydrocaffeic acid-3-o-glucuronide, and Dihydrocaffeic acid-3-o-sulfate………………………………………...108 4.5.8.1 Cinnamic acid Derivatives Caffeic acid, Dihydrocaffeic acid, Dihydrocaffeic acid-3-o-glucuronide, and Dihydrocaffeic acid-3-o- sulfate with BSA………………………………………………………..108 4.5.8.2 Cinnamic acid Derivatives Caffeic acid, Dihydrocaffeic acid, Dihydrocaffeic acid-3-o-glucuronide, and Dihydrocaffeic acid-3-o- sulfate with LDL-VLDL………………………………………………..109 4.5.9.0 Comparison of the Cinnamic acid Derivatives Caffeic acid, Ferulic acid, Isoferulic acid, Isoferulic acid-3-o-glucuronide, and Dihydroferulic acid……………………………………………………………………...111 4.5.9.1 Cinnamic acid Derivatives Caffeic acid, Ferulic acid, Isoferulic acid, Isoferulic acid-3-o-glucuronide, and Dihydroferulic acid with BSA….111 4.5.9.2 Cinnamic acid Derivatives Caffeic acid, Ferulic acid, Isoferulic acid, Isoferulic acid-3-o-glucuronide, and Dihydroferulic acid with LDL- VLDL…………………………………………………………………...112 4.5.10.0 Comparison of the Cinnamic acid Derivatives o-Coumaric acid and p- Coumaric acid, the Benzoic acid Derivative p-Hydroxybenzoic acid, and the Phenylacetic acid derivative p-Hydroxyphenylacetic acid…………114 4.5.10.1 Cinnamic acid Derivatives o-Coumaric acid and p- Coumaric acid, the Benzoic acid Derivative p-Hydroxybenzoic acid, and the Phenylacetic acid derivative p-Hydroxyphenylacetic acid with BSA………………...114 4.5.10.2 Cinnamic acid Derivatives o-Coumaric acid and p- Coumaric acid, the Benzoic acid Derivative p-Hydroxybenzoic acid, and the Phenylacetic acid derivative p-Hydroxyphenylacetic acid with LDL-VLDL………...115 4.6 Conclusion………………………………………………………………….117 References………………………………………………………………………………123 Appendix A: Ka Statistics and Correlations between Methods………………………...129 Appendix B: Ka Correlations among Other Factors……………………………………138 Appendix C: Ka Plots of BSA…………………………………………………………..280 Appendix D: Ka Plots of LDL-VLDL, Fluorescence Spectra, and λmax Shifts…………361 List of Figures Figure 1: Generic phenolic acid structures………………………..………………………5 Figure 2: Ellagic acid………………………………………………………………...……5 Figure 3: Eudesmic acid………………………………………………………...………...6 Figure 4: Syringic acid………………………………………………….………………...7 Figure 5: Gallic acid………………………………………………………………………8 Figure 6: Protocatechuic acid………………………………...…………………………...8 Figure 7: m-Hydroxybenzoic acid…………………………………………….…………..9 Figure 8: p-Hydroxybenzoic acid……………………………..…………………………10 Figure 9: p-Hydroxysalicylic…………………………………….………………………10 Figure 10: Apocynin………………………………………………..……………………11 Figure 11: Vanillic acid…………………………………….……………………………12 Figure 12: Dopac…………………………………………………………………………13 Figure 13: m-Hydroxyphenylacetic acid…………………………………………………13 Figure 14: p-Hydroxyphenylacetic acid…………………………….……………………14 Figure 15: Homogentisic acid……………………………………………………………15 Figure 16: Chlorogenic acid……………………………………………...………………16 Figure 17: Ferulic acid……………………………………………………...……………17 Figure 18: Isoferulic
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