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Fractionation of Egg Yolk Lípids Usíng Supercrítícal Carbon Díoxíde and Entrainer

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Fractionation of Egg Yolk Lípids Usíng Supercrítícal Carbon Díoxíde and Entrainer Fractionation of Egg Yolk Lípids Usíng Supercrítícal Carbon Díoxíde and Entrainer by Lucia T. Labay subm¡ßed to tll Fdr*, {,!1ì)1, in Pañal Fulfillnent oÍ"¡or**l thc Requiremcnts for the Degree of MASTER oF SCIENCE Dcpøtnæu of Food Science Universit, of Manitoba Winnipeg , Maniøba, Canada @ April 1991 A.M.D,G. FR.A,CTIONATION OF EGG YOLK LIPIDS USING SUPERCRITICAL CARBON DIOXIDE AND ENTRAINER BY LUCIA T, LABAY A ¡hesis subntined to thc Faculty of Craduate Studies of the Univcrsily of M¿nitoba in partiel fullìllment of the requirenrerrls of the degrec of I'ÍASTER OF SCIENCE o r99r Permission has bccn granted to thc LIBRARY OF THE UNIVER- S¡TY OF MANITOBA to lend or scll copics of this rhesis. ro IhC NATIONA! LIBRARY OF CANADA tO fNJCfOfiIM this thesis and to lend o¡ scll copies oí th! ,ìlm, and UNIVERSITY MICROF¡LMS to publish an abstract of rhis thesis. The autho¡ ¡escrvcs other publication rights, and neither thc tlcsis nor cxtensivc extracts from it may be pnnlcC or other. wisc rcproduccd without the author's writtcn permission. Abstract The efficacy of egg yolk lipid fractionation with supercritical ca¡bon dioxide and enEainers was studied. The principal aims we¡e to study the feasibility of cholesterol removal and to determine the effects of extraction pressure and temperature and entrainer type and concentration upon extraction rate and lipid fractionation. Analysis for phosphatidylcholine (PC) was also performed. A Superpressure Supercritical Screening unit was used to extract freeze- dried egg yolk samples. Extraction pressure was varied from 15 to 36 MPa at 40"C and extraction temperature was varied from 40'C to 75'C at 36 MPa. Ethanol at 3 wtVo and. methanol at 3 or 5 wt 70 concentration were tried as enÍaine¡s. Extracted samples were analyzed by HPLC for cholesterol content and FAME-CLC for fatty acid profiles. Phospholipid determinations were made using the enzymatic procedure outlined by Boehringer Mannheim. Solubility of extracted lipids was found to be strongly dependent on extraction pressue. Maximum solubility (10 mg,/g CG¿) at 36 MPa, 40'C dropped to a near negligble 0.67 mglg COz at 15 MPa, 40'C. Solubilities were found to dec¡ease wirh increasing tempeÌatue, however, the difference in solubility between 40'C and 55'C was not significant. The inclusion of ethanol and methanol as entrainers also increased solubility significantly; however, at a 37o concentation these two enraine¡s had roughly equivalent effects on increasing solubility. Abstract Lipid recovery, approximating 7 jVo total extractable lipid, appeared to remain constant over the range of pressures and temperatures tested in this study. When an entrained system was run to exhaustion, higher percent recoveries of total lipid were obtained, more so, with entrained systems of higher concentrations. The rate of removal was a function of extraction temperature and pressure and was enhanced significantly by the addition of methanol or ethanol co-solvents. The apparent solubility of cholesterol was found to be dependent on pressure and the addition of entrainer. An increase in CO2 density increased the apparent solubility of cholesterol. The effect of a change in the temperature at constant pressure on the apparent solubility of cholesterol was insignificant over the temperatures studied. The apparent solubility of cholesterol was inc¡eased more by the presence of 3-5 Vo concentrations of entrainer than by changes in the pressure of several MPa. The relative concentration of cholesterol as a percent of egg yolk lipid was found to be affected by the extraction parameters, An increase in temperature increased the relative concentration of cholesterol in the extract. Likewise, a decrease in pressure increased the relative concent¡ation of cholesterol in the extract. The fatty acid composition of the extractions was independent of temperature, pressure and presence of entrainer and remai¡ed constant throughout the extraction. lVhen no entrainer was present, the CO2 extracted lipid was essentially free from phospholipid content (( 0.27o) at both early and late stages of an extraction trial. No appreciable quantities of phospholipids were detected in the exEacts obtained at the onset of an entrained extraction run. However, significant phospholipid levels were found in the entrainer-enhanced SC-CO2 lipid extracts collected in the latter part of the run. 111 Acknowledsements My sincerest thanks is expressed to my two supervisors, Dr. N.R. Bulley and Dr. S. Arntfield. A thank-you to Dr. N.R. Bulley for his financial support and for his advice during the cou¡se of this ¡esea¡ch. Thank-you to Dr. S. Amtfield, your corûnitment to high quality and attention to detail challenged me and pushed me to achieve my personal best; you¡ help was mosl encouraging at all times. I am grateful to Dr. E.D. Murray and the Department of Food Science for providing me with testing facilities. Sincere appreciation is extended to Dr. E.D. Murray for his encouragement during our consultations and for his guidance of my M.Sc. program. Special thanks are due to J. Rogers and M. Szczygiel who kindly provided technical advice on many occasions. Deepest appreciation is extended to W.J. Crera¡ who helped me throughout the course of this endeavour by providing both unfailing moral support and technical support, I was fortunate, to say the least, to have my brother, Vladimir, as my closest companion and colleague during our years of study together at the University of Manitoba. Heartfelt thanks are given to my husband, Kevin, for his enthusiasm and waÍn encouragement during my studies. Lastly, I would like to thank my parents, Rudolph and Dorothy Labay. You have brought me to this day and the g¡eatest lesson I leamed has not b€en from academia - most of all you have taught me that knowledge is not won by human effort but is a gift from God Alrnighty. Ad Majorem Dei Gloriam! lv Table of Contents A B STRA CT 1r ACKNOWLEDGEMENTS lV LIST OF TABLES viï LIST oF FIGURES xi 1.0 INTRoDUCTToN 2,0 LITERATURE REvIE\ry 8 2.I The chemical compostion and structure of eggs (Gallus domesticus) 8 2. I . i Composition of egg yolk 8 2.1.1.1 Egg yolk lipids 10 2,2 The role of eggs in health IJ 2.2.1 Nutritive value of eggs 15 2.2.2 Cholesterol 16 2.2.2.1 Structwe t6 2.2.2.2 Biomedical Importance 16 2.2.2.3 Diet and rískfactors ín cornary heart disease 18 2 .3 Lecithin 26 2. 3. 1 Strucrure, nomenclatu¡e, composition, sources 26 List ofTables 2.3.2 Commercial lecithin products and food use of soybean lecithin 29 2.3.3 Therapeutic and research applications of lecithin 29 2.4 Isolation of egg components 33 2.4.1 Conventional methods of exuaction 33 2.4.2 Supercritical exraction 34 2.4.2.1 Supercritical carbon dioxide as a solvent 34 2.4.2.2 Solubiliry of organic compounds in SC--COz 38 2.4.2.3 Supercrical extractíon of lipids 40 3.0 EXPERIMENTAL EQUIPMENT AND PROCEDURES 42 3, 1 Experimental Equipment 42 3.1.1 Extraction apparatus 42 3. 1. 1 . 1 Extraction vessel, temperature & pressure regulation 44 3.1 .l .2 FIow control 44 3.1.1.3 Fbw ra¡e 44 3.1.1 .4 Sample Collection 44 3. I .2 Experimental extraction procedu¡es 46 3.1 .2.1 Operating conditions, pressure, temperature entrainer, flow rate 46 3.1 .2.2 Vessel loading procedure 47 3.1.2.3 System start-up and pressurization 47 3.1.2.4 Extractsanpling 48 3.1.2.5 Shat-downandpost-extractîon 48 3.2 Maferials 48 3.2.1 Egg Yolk 48 3 .2.2 Exvaction solvents 49 3.2.2.1 Carbon díoxide 49 vi List ofTables 3.2.2.2 Entrainedmixwes 49 3.2.3 Analytical standa¡ds, chemica-ls, solvents 51 3.3 Extract ânalysis 51 3. 3. 1 Compositional analysis 51 3.3.2 Analysis of fatty acids 51 3.3.2.1 Transesterificatíon 52 3 .3.2.2 G.C . identification and quantification 52 3.3.3 Extraction and quantification of cholesterol by FIPLC 53 3.3.4 Phospholipid analysis 56 3.4 Data calculations 58 3.4.1 ExFaction data 58 3.4.1. I Mass Balance 60 3.4.1.2 Solubility determinatiors 60 3.4.1.3 Lipid Recovery 65 3.4.2 Component analysis of extracts 66 3.4.2.1 Fatty acid data standarization 66 3.4.2.2 Triglyceride solubiliry 68 3.4.2.3 Cfutlesterol 68 4.0 RESULTS AND DISCUSSION 70 4.1 Introduction 70 4.2 Lipid Solubility 70 4.2,1 EggLipid Solubility as a Function of Temperature and Pressure 7l 4.2.2 EggLipid Solubility as a Function of Entrainer Type and Concentration 74 4.3 Lipid Recovery 78 4.3.1 Effect of Temperature, P¡essu¡e and Entrainer 78 List ofTables 4 ,4 Chemical Analysis of Extracts 81 4.4.1 Triglycerides 82 4.4.1,I Effect of temperature, pressure, and entrainer on solubility 82 4.4.1.2 Fatty acid compositíon of CO2 exrracts 84 4.4.1.2.1 Fatry acid compositíon of sequential CO2 extacts 84 4.4.1.2.2 Effect of temperature, pressure and use of entraíner on fatty acid compositíon 87 4.4.2 Cholesterol 89 4.4.2.1 Effect of temperature, presswe, an¿ entrainer oft solubílíty and recovery 89 4.4.2.2 Effect of extraction time 96 4.4.3 Phospholipid recovery 96 4.5 Chemical Analysis of Residue 99 5.0 CoNCLUSIONS AND RECoMMENDATIONS r02 5.1 Conclusions r02 5.2 Recommendations 105 REFERENCES t07 APPENDIX A Lt7 VUI List ofTables Líst of Tables TABLE 2.1: Constituents of egg yolk.
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