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COLOR STABILITY of SORGHUM 3-DEOXYANTHOCYANINS AGAINST SULFITE and ASCORBIC ACID DEGRADATION; Ph INFLUENCE

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COLOR STABILITY of SORGHUM 3-DEOXYANTHOCYANINS AGAINST SULFITE and ASCORBIC ACID DEGRADATION; Ph INFLUENCE COLOR STABILITY OF SORGHUM 3-DEOXYANTHOCYANINS AGAINST SULFITE AND ASCORBIC ACID DEGRADATION; pH INFLUENCE A Thesis presented to the Faculty of the Graduate School at the University of Missouri-Columbia In Partial Fulfillment of the Requirements for the Degree Master of Science by LEONNARD ODHIAMBO OJWANG Dr. Joseph Awika, Thesis Supervisor DECEMBER 2007 The undersigned, appointed by the dean of the Graduate School, have examined the thesis entitled COLOR STABILITY OF SORGHUM 3-DEOXYANTHOCYANINS AGAINST SULFITE AND ASCORBIC ACID DEGRADATION; pH INFLUENCE presented by Leonnard Odhiambo Ojwang, a candidate for the degree of Master of Science, and hereby certify that, in their opinion, it is worthy of acceptance. _______________________________________________________________ Joseph Awika, Ph.D., Department of Food Science _______________________________________________________________ Ingolf Gruen, Ph.D., Department of Food Science _______________________________________________________________ Mark Ellersieck, Ph.D., Department of Statistics DEDICATION To my dad Mr. John W. O. Ojwang and mum Mrs. Martha A. Ojwang. Your constant motivation and faith has always given me hope. Now, this is was your dream, through me. Thank you. ACKNOWLEDGEMENTS My heartfelt gratitude goes to Dr. Joseph Awika for all his help, encouragement and dedication in helping me advance my knowledge and making this work possible. Also, I wish to extend pure thanks to Dr. Ingolf Gruen and Dr. Mark Ellersieck, for their counsel, time and guidance. They offered the critique that strengthened this work. Gratitude is also extended to JoAnn Lewis for carefully editing this thesis and her attention to finer details; and to Elizabeth Melanson, Liz Fenner, Victoria B. Spradling and Liyi Yang of the Department of Food Science and Nutrition for their hearty willingness to offer assistance and encouragement during the entire research work. ii TABLE OF CONTENTS ACKNOWLEDGEMENTS …………………..……………………....…………..………ii LIST OF FIGURES …………………………………………..……..…………..….……vi LIST OF TABLES ……………………………………..…………………...…………....ix ABSTRACT ……………………………………..…………………………..……..…….x Chapter 1. INTRODUCTION ……………………...…………………………..……………..1 1.1. Need for research ……………….………………………..………..……….....1 1.2. Objectives of research …………………….………………………....….…….4 2. REVIEW OF LITERATURE ………………...…………………..…………….…5 2.1. Background information ………………………………..……..…….……..…5 2.2. Factors contributing to anthocyanin instability ……………………..……….10 2.2.1. pH …………...……………………………………….…………...…..10 2.2.2. Light …………………………………………………..……….…......12 2.2.3. Temperature ………………………………………..……….…...…...14 2.2.4. Oxygen ……………………………………………..…………....…...16 2.2.5. Enzymes ……………………………………………..………....…….18 2.2.5.1. Pectic enzyme………….……………………..…….....……..18 2.2.5.2. Polyphenol Oxidase (PPO) Enzyme…………..……..…..…..18 2.2.6. Presence of co-pigments including flavonoids, polyphenols, alkaloids, amino acids, metals and organic acids…......……..……..19 2.2.7. Solvent ………………………………………………..…………...…22 2.2.8. Substitution on the chromane ring (A and C rings) …………..…..….22 2.3. The Chromatic behavior of anthocyanins in presence of SO2 and ascorbic acid ………………….......……………………….……….……..25 2.3.1. Sulfur dioxide, SO2 ……………...……………….……..…….……. 25 2.3.2. Ascorbic acid (Vitamin C) …………...…..………………………….27 2.3.3. Improving on the available knowledge in the study of 3-deoxyanthocyanin pigments…………….…….……………...….29 3. MATERIALS AND METHODS ……………………………...………..……......30 3.1. Chemicals, samples and reference compounds ………………...……..……..30 3.1.1. Chemicals ……………………………...………….….……....………30 3.1.2. Sample and reference compounds.…….……...…….…..............…....30 3.1.3. Sorghum bran handling ………………………….….…...…..……….30 3.1.4. The 3-deoxyanthocyanin pigment extraction ..…….……....…...…….31 3.1.5. Model solutions……………………...……………….……………….32 3.1.6. Synthesis of anthocyanidin-pyruvic acid adducts ….…….....…..……32 iii 3.2. Methods for the objectives ……………………………….…....…………….33 3.2.1. Research objective 1. Establish stability of sorghum 3- deoxyanthocyanins against SO2 and ascorbic acid bleaching at different pH levels relative to commercial anthocyanin pigments ………….………….……………………………………..33 3.2.1.1. SO2 assay ………..…………………………..……………….33 3.2.1.2. Ascorbic acid assay ………..………..………………………..34 3.2.1.3. UV-Vis absorption spectra ……..………..……...……………34 3.2.2. Research objective 2. Determine effectiveness of pyruvic acid addition on sorghum 3-deoxyanthocyanin stability against SO2 and ascorbic acid bleaching ………………………....………...……35 3.2.2.1. HPLC-DAD analysis ……………..………..………………...35 3.2.2.2. LC-MS analysis …………………………………..………….35 3.2.2.3. UV-Vis absorption spectra …….…...………………………...36 3.2.2.4. Data analysis …...…………..……...…………………………36 3.2.3. Research objective 3. Determine effects of commercial Sterilization conditions on 3-deoxyanthocyanins stability...…..….37 3.2.3.1. Autoclaving process …………….…………….……….…..…37 3.2.3.2. Sample analysis ……………………………..………..………37 4. RESULTS AND DISCUSSION …………………………....…………………...38 4.1. Crude black sorghum pigments …………….…….……..……………….…38 4.2. Effect of SO2 and ascorbic acid on 3-deoxyanthocyanin pigments stability at different pH levels ……………………………………..…...…39 4.2.1. Stability of 3-deoxyanthocyanins pigments …...…..……….…..….…40 4.2.2. Effect of SO2 on stability of the control samples.....…………….……41 4.2.3. Effect of ascorbic acid on stability of the control samples .…….……45 4.3. Synthesis of 3-deoxyanthocyanin-pyruvic acid adducts ………..……...……47 4.3.1. Significance of pyruvic acid addition ………………….………….….47 4.3.2. HPLC-DAD/MS analysis ……………………....……..………..….…47 4.3.3. Possible mechanisms of 3-deoxyanthocyanin-pyruvic acid reactions.……...…………..………………………………………...52 4.3.3.1. Apigeninidin, luteolinidin and 7-methoxyapigeninidin……....52 4.3.3.2. The dimethoxylated 3-deoxyanthocyanin pigments……….…54 4.3.4. Effect of pyruvic acid on stability of 3-deoxyanthocyanin pigments ….....................................................................................…55 4.3.5. Effect of SO2 on samples with pyruvic acid ………...……….….……56 4.3.6. Effect of ascorbic acid on samples with pyruvic acid ……..…….....…63 4.4. Effect of high temperature processing ……………………………....……...69 4.4.1. Spectroscopic analysis of heat treated samples …………………..….69 4.4.2. HPLC analysis of heat treated samples ……….…...……………........71 4.4.2.1. Crude sorghum pigment ……………………….……….....…71 4.4.2.2. Non- and mono- methoxylated 3-deoxyathocyanin standards ….….……….……………………………..……72 4.4.2.3. The dimethoxylated 3-deoxyanthocyanin pigments ……...…74 iv 5. CONCLUSIONS, RECOMMENDATIONS AND SUMMARY …...…………75 5.1. Conclusions ……………………...…………………………………….…..75 5.2. Recommendations for further research ………...……………..……….…..79 5.3. Summary ……………..……………………….……………..……….……80 APPENDIX………………………………………………………………………...…….82 1. SAS DATA…………………………………………………………………..82 1.1. ANOVA tables for samples with SO2…………………………………82 1.2. ANOVA tables for samples with ascorbic acid……….…………...…..86 REFERENCES ……………………………………………………...…………..………91 v LIST OF FIGURES Figure Page 1. Chemical structure of (A), the six common anthocyanidins, and (B), the 3-deoxyanthocyanins …………………...……………………………….….6 2. Mechanism for the formation of anthocyanin-pyruvic acid adducts: cyanidin, 1; pyruvic acid, 2; and cyanidin-pyruvic acid adducts, 3 ……..….….8 3. Structural transformations of anthocyanins. R1 and R2 are usually H, OH, or OCH3 ……………………………………………………………………...…11 4. Structural re-arrangement of anthocyanins due to the effect of light ……...…….13 5. Transformation of a Flavylium salt, (I) into an O-benzoyloxyphenylacetic acid, (II) during ozonolysis ……………………….…..…...………………......17 6. Proposed reaction mechanism for the formation of new pyranoanthocyanin adduct with pelargonidin 3-glucoside and ferulic acid (co-pigment). R = glucoside residue ……………………..…………...………………....……21 7. Bisulfite addition on carbon 2 or 4 on the anthocyanin molecule …………….....26 8. Ascorbic acid ……………………..…...…………………………………..……..27 9. HPLC chromatogram of crude sorghum pigment ……………..……..………….39 10. Sulfite addition reaction: 3-deoxyanthocyanin molecules, (I); and resultant colorless sulfonates, (II) ………………..…….………...…….....44 11(a): HPLC profile of apigeninidin, before (I); and after reaction with pyruvic acid (A), (II), pH 3.2, after 10 days at λmax (nm)…….….….….………...….48 11(b): HPLC profile of luteolinidin, before (I); and after reaction with pyruvic acid (A), (II), pH 3.2, after 10 days at λmax (nm).……….…...…...…............49 11(c): HPLC profile of 7-methoxyapigeninidin, before (I); and after reaction with pyruvic acid (A), (II), pH 3.2, after 10 days at λmax (nm) ………..…...50 vi 11(d): HPLC profile of 5,7-dimethoxyluteolinidin, before (I); and after reaction with pyruvic acid (A), (II), pH 3.2, after 10 days at λmax (nm)…....51 12. Proposed scheme for the formation of 3-deoxyanthocyanin-pyruvic acid adducts: apigeninidin, luteolinidin or 7-methoxyapigeninidin molecule, 1; pyruvic acid, 2; and the 3-deoxyanthcyanin-pyruvic acid adducts, 3………....53 13. Proposed mechanism for the formation of dimethoxylated 3-deoxyanthocyanin- pyruvic acid adducts following reaction mechanism proposed by Jurd (1964b)....................................................................................................…54 14(a): Effect of 60 ppm SO2 and pyruvic acid on stability of sorghum, red cabbage and 3-deoxyanthocyanin standards after 21 days (27°C) at pH 2.0……………...…………………………...….……………………...57 14(b): Effect of 60 ppm SO2 and pyruvic acid on stability of sorghum and 3-deoxyanthocyanin standards after 21
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