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JOEL BITMAN Status Report on the Alteration of Fatly Acid and Stero! Composition in Lipids in Meat, Milk' and Eggs Demonstration of the high positive correlation between saturated fat intake and heart disease (Figure 1) and between blood cholesterol levels and heart disease (Figure 2) has made the American consumer wary of the fat in meat, milk, and eggs. The percentage of fat con- tributed by these food groups over a 20-year period is shown in Table 1 (Economic Research Service, 1965; Agricultural Statistics, 1969~. A 50% decline in butter consumption and 20% decline in egg consump- tion were especially meaningful trends. The American consumer has maintained a high consumption of beef, but that portion that is fat is an unwanted obesity-inducing nutrient. Thus, in 1973 approximately 2.5 billion pounds of excess fat, valued at 1.15 billion dollars, were trimmed from beef carcasses (Hendricks, 19741. The animal scientist, reluctantly and belatedly, has finally recognized and accepted this message from the marketplace. Within the last few years, research has been directed towards altering animal fats to make them more acceptable to the consumer, i.e., to in- crease the polyunsaturated fats in meat and milk and to lower the cholesterol in eggs. The task that faces the scientist who wants to change the lipid composition of the ruminant is considerably more difficult than it is to change the body fat composition of the nonruminant. In mono- gastric animals, such as man, pig, and chicken, body fat can be changed readily by changing the composition of the diet. Many experiments 200

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Alteration of Fatty Acid and Sterol Composition in Lipids 201 40 20 20 10 _ CHD DEATH RATE PER 1000 n n n n ~ CALORIES FROM SATURATED FATS ~n 11 GR JAP NETH FIN YUGO IT US FIGURE 1 Coronary heart disease deaths and percentage of total calories provided by saturated fats in the diet of men from seven countries (Keys, 1970). have demonstrated that if higher levels of dietary polyunsaturated fats are fed to pigs and chickens, these polyunsaturated dietary lipids will be absorbed and incorporated into body fat. In ruminants, however, if increased amounts of polyunsaturated fats are fed, they are utilized by microorganisms in the rumen or metabolized by these organisms to form saturated and mono-unsaturated fatty acids; as a result, the meat and milk fat do not show any increase in polyunsaturated fat. The data in Table 2 demonstrate that although the normal plant diet of the ruminant is primarily polyunsaturated, both meat and milk fat normally TABLE 1 Contribution of Fat from Various Food Groups a Percentage of Fat Contributed by 1947-19491968 Change (% ) - Meat, including fish 33.5%35.2% +S Milk and dairy products, including butter 21.6%17.1% -20 Eggs 4.3 %3.4% -20 Total 59.4%55.7% -6 a Data from ERS, 1965; and Agricultural Statistics, 1969.

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202 o o to Cal LL JOEL BITMAN 200 50 00 50 FIRST MAJOR CORONARY EVENT _ MEN 40-59 ~ :,n,n,n,J,Q,: 175 200 225 250 275 300 SERUM CHOLESTEROL mg 96 FIGURE 2 Relationship between serum cholesterol level and incidence rate of the first major coronary event (Intersociety Commission for Heart Disease Re- sources, 1970). contain only 2%-4% polyunsaturated fat (Hilditch and Williams, 1964; Bitman et al., 1974b). Recently, a process was developed that represents a breakthrough in the attempt to increase the polyunsaturated, fatty-acid content of TABLE 2 Fatty Acid Composition of Pasture Grass and Bovine Milk and Meat Fat a Weight in Lipid ( % ) Fatty Acid Grass Milk Meat Myristic 14 01 12 3 Palmitic 16:011 31 26 Stearic 18:02 11 14 Oleic 18:15 24 47 Linoleic 18:212 3 3 Linolenic 18:362 1 1 Others 7b 18c 64 a SOURCE: grass (Hilditch and Williams, 1964); mild and meat fat (Bitmap e' al., 1974a). b Primarily 12:0 and 16: 1. c 4:0-12:0 comprise, 11%; 14:! and 16:1, 4%; minor acids, 3%. Primarily 16:1.

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Alteration of Fatty Acid and Sterol Composition in Lipids 203 ruminant meat and milk. T. W. Scott and his colleagues in Australia (Scott et al., 1970) coated polyunsaturated oils with a protein and then protected these particles from microbial attack in the rumen by treat- ment with formaldehyde. The coated oils passed through the rumen (pH 6-7) and into the abomasum and omasum (ply 2-3), where the more acid conditions hydrolyzed the protein-formaldehyde coat, re- leasing the intact dietary polyunsaturated oil, which could then be ab- sorbed and incorporated into body and milk lipid. The process had earlier been utilized by Ferguson et al. (1967) to increase wool growth of sheep by protecting dietary casein from microbial degradation in the rumen. This innovative technique has been the subject of intensive research within the last 4 years and has, for the first time, provided a range of new polyunsaturated ruminant foods. An attempt has been made in this review to summarize research di- rected towards altering the fatty-acid and sterol composition of meat, milk, and eggs. The typical fatty-acid composition of the foods of animal origin is shown in Table 3. This is the base upon which the experimental alterations have been made. It can be seen that ruminant fat contains more saturated fatty acids and less polyunsaturated fatty acids than do swine and poultry fat. Of the three major dietary components fats, pro- teins, and carbohydrates most attention has been given to the effects of feeding fats upon the fatty-acid and cholesterol composition of the animal. The tables are intended to group typical experimental findings and are not necessarily comprehensive and complete. TABLE 3 Typical Fatty-Acid Composition (Weight Percent) of Fat from Different Animal Sources a Ruminant Nonruminant Fatty Acid Milk Beef Pork Poultry Eggs Saturated Lower C`-C1. 11 Myristic 14:0 12 3 1 1 1 Palmitic 16:0 31 26 25 25 23 Stearic 18:0 11 14 14 4 4 Unsaturated Palmitoleic 16:1 4 3 3 7 5 Oleic 18:1 24 47 47 43 47 Linoleic 18:2 3 3 8 18 16 Linolenic 18 :3 1 1 - 2 Others 3 3 2 2 2 a Data from Hilditch and Williams ( 1964) and Bitman et al. (1974a).

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204 A SYNOPSIS OF ALTERATIONS IN THE LIPID COMPOSITION OF SWINE JOEL BITMAN A summary of the changes brought about in fatty-acid composition by experimental dietary alterations in swine is presented in Table 4. The data clearly demonstrate the ready capacity of the pig to store fat of the type present in its diet. A wide variety of plant and fish oils, con- taining large quantities of polyunsaturated fatty acids, were fed to pigs; and the polyunsaturated fats were promptly absorbed and incorporated into their body fat. Most of these studies were conducted with growing pigs (8-28 weeks); end the depot fat alterations, although rapid, re- quired several months to achieve equilibrium. Experiments during the twenties and thirties, in which polyunsaturated fats were added to the diet, produced a soft or oily pork, characterized by a high linoleic ( 18: 2) and a low palm~tic ( 16: 0) and low stearic ( 18: 0) content.* Consumer acceptability was poor. While Table 4 may appear to indicate that alterations in the fatty-acid composition of swine have been well explored, I would suggest that this table, based upon approximately twenty reports, instead shows that fat ~ The first number refers to the length of the carbon chain in the fatty acid; the second, to the number of double bonds in the chain. TABLE 4 Fatty Acid Changes in Pig Fat a Diet 18:2 18:1 18:0 16:0 16:1 20-22 References Plant Lipids Corn, corn oil + 67, 68, 69, 71, 82, 123 Soybeans, soybean oil + - - - 16, 68, 69 Peanuts + - - - 68, 69 Cottonseed oil + - + - 70 Fish Lipids Menhaden oil Whale oil Cod liver oil-lard Animal Lipids Tallow Cholesterol VFA High carbohydrate Vitamin D Copper 17, 18 83 + + 84 O O O O + + + O + - O 123 113 14 66 113 2, 30, 142, 212 a CODE: ~ = increase,-= decrease, and 0 = no change.

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Alteration of Fatty Acid and Sterol Composition in Lipids 205 modification research in pigs is relatively limited when compared to the number of studies on the role of fat in cardiovascular disease, where literature references run into the hundreds. The advent of modern gas-liquid chromatography has made investigation in this area much more practicable. Thus, the mechanism for control of fat composition in swine would seem to be susceptible to more exact elucidation. There are some additional, scattered literature references that indicate that several other factors affect fatty-acid composition (sex, age, breed, starvation, temperature), but this limited information was not included. A SYNOPSIS OF ALTERATIONS IN THE LIPID COMPOSITION OF POULTRY DEPOT AND EGG LIPIDS Summaries of the changes that can be effected in fatty-acid composition of poultry depot fat and egg lipids are presented in Tables 5 and 6. Several major features are apparent: 1. Alterations in egg lipids are complete within 16 days, while depot fat changes are much slower, requiring several months to reach an equilibrium. This difference reflects ovum maturation time in the egg-laying cycle and a relatively rapid transfer of blood lipids to a small fat compartment (egg lipids) in contrast to a much slower balance between blood lipids and a large lipid compartment (depot fat). 2. The chicken stores fat of the type present in its diet: dietary saturated or unsaturated fat causes the deposition of lipids of that re- spective type in the depot fat. 3. Dietary unsaturated fats pass readily into egg lipids, thus ingestion of a wide variety of unsaturated plant oils results in the appearance of the characteristic unsaturated fatty acids in the egg. Dietary saturated fats, however, have relatively little influence upon the composition of egg lipids. 4. An approximate inverse relationship exists between linoleic acid and oleic acids in egg and tissue lipids in response to dietary unsaturated fat ingestion. Particularly because of the marked resistance to change of the saturated fatty acids in egg lipids, most compositional changes in response to dietary fats occur in the relative proportions of 18:2 and 18:1. To the extent that generalizations between species are valid in these two monogastric animals, the chicken and the pig, it is apparent that the body fat of swine and poultry will reflect either greater saturation or unsaturation, depending upon the composition of the diet. Egg lipid composition, however, can be altered readily only in the direction of more unsaturated lipids.

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208 SYNOPSIS OF ALTERATIONS IN EGG CHOLESTEROL CONTENT JOEL BITMAN Table 7 presents a summary of factors that can alter egg cholesterol content. Such limited studies as have been carried out on age and season as factors influencing egg cholesterol have not been included. A large number of studies dealing with changes in serum cholesterol and liver cholesterol in poultry, but which do not contain data on egg cholesterol, are not discussed in this review. Cholesterol, like the other lipids in eggs, can be altered by dietary means. Studies with labeled acetate (Kritchevsky and Kirk, 1951, Kritchevsky et al., 1951), cholesterol (Andrews et al., 1965, 1968; Connor e! al., 1965), and triglycerides (Budowski et al., 1961) and the experiments with cholesterol inhibitors in which desmosterol builds up in the egg (Burgess et al., 1962) have demonstrated that changes in egg cholesterol occur within hours of treatment. The time course of egg cholesterol changes thus appears to agree well with the time course of changes in egg fatty-acid composition (Reiser, l951b). Data from studies with dietary lipids disclose a large number of un- certainties. Thus, there is no agreement on whether or not corn oil, safflower oil, linseed oil, soybean oil, or coconut oil will increase egg cholesterol. Use of almost every oil at the same level by different workers has yielded different results. At the present time there is no good explanation for these serious discrepancies in research results by reputable, competent scientists. The inclusion of cholesterol in the diet of the hen promptly causes increased amounts of cholesterol in the egg. Addition of fat to the diet along with the cholesterol rather uniformly produces a doubling in egg cholesterol, probably by increasing the absorption of dietary cholesterol in the gut. Agents that influence (a) the intestinal absorption or (b) the enterohepatic circulation of cholesterol alter egg cholesterol. Thus, surface-active agents such as Tween or lecithin improve cholesterol adsorbability and increase egg cholesterol. Conversely, the plant sterol, ,3-sitosterol, promotes the fecal excretion of cholesterol and conse- quently decreases egg cholesterol. Sitosterol quantitatively replaces cholesterol in the egg. Two published reports, which disagree, are inadequate to determine whether dietary fiber reduces or increases egg cholesterol. The few studies with vitamins do not demonstrate striking or consistent effects. D-thyroxine was found to increase egg cholesterol, apparently by stimu lating cholesterol turnover and excretion via the egg.

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Alteration of Fatty Acid and Sterol Composition in Lipids TABLE 7 Effect of Dietary Agents on Egg Cholesterola 209 Group Agent Effect References Oils Corn Safflower Linseed + o 39 32,63,80,122,143, 158, 220 7, 80, 209, 219, 220 220,222 80, 219 222 Soybean + 80, 209 0 7,51 Coconut + 7, 220 0 32 Cottonseed 0 167 Lard 0 32,63 Tallow 0 39, 51, 63, 80, 122, 158, 220 Rapeseed 0 122 Sterols Cholesterol + 32, 52, 53, 60, 64, 90, 102, 135, 182, 220, 226 0 121, 136 Sitosterol - 36 0 220 Protein 0 39, 63, 143, 158 Surface Active Tween 0 220 Lecithin 0 220 Cholestyramine 0 111, 134 Tween-cholesterol + 220 Lecithin-cholesterol + 220 Fiber Cellulose + 135 Cellulose - 216 Pectin - 216 Vitamins Niacin 0 220 Vitamin C 0 155 Vitamin A + 182 0 60, 220 Drugs Clofibrate 0 220 MER-29 - 25 Azasterols - 184 Diethyl-aminoethyl diphenyl valerate - 146 Probucol - 146, 147 Hormones D-thyroxine + 220 a CODE: + = increase,-= decrease, and 0 = no change.

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210 JOEL BITMAN Drugs that inhibit the biosynthesis of cholesterol at the reductive step in the pathway from desmosterol to cholesterol have been successful in lowering egg cholesterol, but there is an accompanying quantitative replacement of cholesterol by desmosterol. This alteration raises several questions: 1. Are eggs containing large quantities of desmosterol satisfactory as human foods? 2. What level of cholesterol is necessary in the developing ovum to permit satisfactory egg production? 3. What levels of desmosterol can the chicken successfully cope with? What are the long-range physiological consequences for the hen of in- creased levels of desmosterol? A number of studies have demonstrated that egg cholesterol concen- tration varies genetically. Eggs from broiler-breeder strains contained more cholesterol than did those from commercial layer strains (Edwards et al., 1960; Miller and Denton, 1962; Harris and Wilcox, 1963a; Col- lins et al., 1968; Turk and Barnett, 1971; Marks and Washburn, 1973; Cunningham et al., 1974; Washburn and Nix, 1974~. Whether these differences are large enough to be nutritionally and physiologically meaningful to humans has not yet been determined. Many of the substances that have been used in attempts to alter egg cholesterol are agents that reduce serum cholesterol in other species. Review of the serum cholesterol changes of the studies summarized in Table 7 indicated that there was no simple direct relationship between plasma and egg cholesterol concentration. Thus, both D-thyroxine and ,3-sitosterol lowered blood cholesterol; thyroxine increased egg cho- lesterol, while sitosterol lowered it. Cholestyramine caused a very large decrease in serum cholesterol but had no effect upon egg cholesterol. Feeding dietary oils or oils with cholesterol raised serum cholesterol and also raised egg cholesterol. A diagrammatic representation of major cholesterol compartments of the laying hen is shown in Figure 3. The lack of consistent results and the lack of understanding of cholesterol relationships in the laying hen suggest that the time has arrived for complete metabolic balance studies in egg cholesterol reduction research. Although studies of this type would be expensive, the many studies listed in Table 7 attest to the large amount of money already expended on this problem. Measure- ment of cholesterol levels in the diet, plasma, fat, liver, body, egg, and excrete; the use of labeled cholesterol; and gas chromatography to identify egg sterols could bring order to the cholesterol picture order

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Alteration of Fatty Acid and Sterol Composition in Lipids 227 casein-sa~ower oil supplement for dairy cows. II. Effect on the fatty-acid composition of plasma and milk lipids. J. Dairy Res. 39:211. 42. Cook, L. J., T. W. Scott, G. J. Faichney, and H. Lloyd Davies. 1972b. Fatty acid interrelationships in plasma, liver, muscle, and adipose tissues of cattle fed safflower oil protected from ruminal hydrogenation. Lipids 72:83. 43. Cook, L. J., T. W. Scott, K. A. Ferguson, and I. W. McDonald. 1970. Pro- duction of polyunsaturated ruminant body fats. Nature 228: 178. 44. Coppock, J. B. M. 1962. Some aspects of the influence of diet and husbandry on the nutritional value of the hen's egg. Chem. Ind., May, p. 886. 45. Couch, J. R., B. M. Cornett, T. M. Ferguson, and C. R. Creger. 1970. Effect of dietary fat on the fatty acid composition of turkey egg yolks. Nutr. Rep. Int. 1:83. 46. Crouse, J. D., J. D. Kemp, J. D. Fox, D. G. Ely, and W. G. Moody. 1972. Effect of castration, testosterone and slaughter weight on fatty acid content of ovine adipose tissue. J. Anim. Sci. 34:384. 47. Cruickshank, E. M. 1934. CXXXVI. Studies in fat metabolism in the fowl. I. The composition of the egg fat and depot fat of the fowl as affected by the ingestion of large amounts of different fats. Biochem. J. 28:965. 48. Cunningham, D. L., W. F. Kruger, R. C. Fanguy, and J. W. Bradley. 1974. Preliminary results of bidirectional selection for yolk cholesterol level in laying hens. Poult. Sci. 53:384. 49. Czulak, J., L. A. Hammond, and J. F. Horwood. 1974a. Cheese and cultured dairy products from milk with high linoleic acid content. I. Manufacture and physical and flavor characteristics. Aust. J. Dairy Technol. 29:124. 50. Czulak, J., L. A. Hammond, and J. F. Horwood. 1974b. Cheese and cultured dairy products from milk with high linoleic acid content. II. Effect of added lipase on the flavor of the cheese. Aust. J. Dairy Technol. 29: 128. 51. Daghir, N. J., W. W. Marion, and S. L. Balloun. 1960. Influence of dietary fat and choline on serum and egg yolk cholesterol in the laying chicken. Poult. Sci. 39:1459. 52. Dam, H. 1928. Die Synthese und Resorption des Cholesterins beluchet durch Versuch an Huhnereiern. Biochem. Z. 194:188. 53. Dam, H. 1929. Cholesterinstoffwechsel in Huhnereiern und Huhnehen. Bio- chem Z. 215:475. 54. Devier, C. V., and W. H. Pfander. 1974. Source and level of dietary fat on fatty acid and cholesterol in lambs. J. Anim. Sci. 38:669. 55. Dinius, D. A., R. R. Oltjen, and L. D. Satter. 1974a. Influence of abomasally administered safflower oil on fat composition and organoleptic evaluation of bovine tissue. J. Anim. Sci. 38:887. 56. Dinius, D. A., R. R. Oltjen, C. K. Lyon, G. O. Kohler, and H. G. Walker, Jr. 1974b. Utilization of a formaldehyde treated casein-safflower oil com- plex by growing and finishing steers. J. Anim. Sci. 39: 124. 57. Dryden, F. D., and J. A. Marchello. 1973. Influence of dietary fats upon carcass lipid composition in the bovine. J. Anim. Sci. 37:33. 58. Dryden, F. D., J. A. Marchello, W. C. Figroid, and W. H. Hale. 1973. Composition changes in bovine subcutaneous lipid as influenced by dietary fat.J.Anim.Sci.36:19. 59. Dryden, L. P., J. Bitman, T. R. Wrenn, J. R. Weyant, R. W. Miller, and L.

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228 JOEL BITMAN F. Edmondson. 1974. Effect of Triundecanoin upon lipid metabolism in the cow. J. Am. Oil Chem. Soc. 51:302. 60. Dua, P. N., B. C. Dilworth, E. J. Day, and J. E. Hill. 1967. Effect of dietary vitamin A and cholesterol on cholesterol and carotenoid content of plasma and egg yolk. Poult. Sci. 46:530. 61. Edmondson, L. F., R. A. Yoncoskie, N. H. Rainey, F. W. Douglas, Jr., and J. Bitman. 1974. Feeding encapsulated oils to increase the polyunsatura- tion in milk and meat fats. J. Am. Oil Chem. Soc. 51 :72. 62. Edwards, H. M., Jr., J. C. Driggers, R. Dean, and J. L. Carmon. 1960. Studies on the cholesterol content of eggs from various breeds and/or strains of chickens. Poult. Sci. 39:487. 63. Edwards, H. M., Jr., J. E. Marion, and J. C. Driggers. 1962. Serum and egg cholesterol levels in mature hens as influenced by dietary protein and fat changes. Poult. Sci. 41 :713. 64. Edwards, H. M., Jr., and V. Jones. 1964. Effect of dietary cholesterol on serum and egg cholesterol levels over a period of time. Poult. Sci. 43 :877. 65. Edwards, R. L., S. B. Tove, T. N. Blumer, and E. R. Barrick. 1961. Effects of added dietary fat on fatty acid composition and carcass characteristics of fattening steers. J. Anim. Sci. 20:712. 66. Ellis, N. R. 1933. Changes in quantity and composition of fat in hogs fed a peanut ration followed by a corn ration. USDA Tech. Bull. 368. 67. Ellis, N. R., and O. G. Hankins. 1925. Formation of fat in the pig on a ration moderately low in fat. J. Biol. Chem. 66: 101. 68. Ellis, N. R., and PI. S. Isbell. 1926a. Soft pork studies. II. The influence of the character of the ration upon the composition of the body fat of hogs. J. Biol. Chem. 69:219. 69. Ellis, N. R., and H. S. Isbell. 1926b. The effect of food fat upon body fats, as shown by the separation of the individual fatty acids of the body fat. J. Biol. Chem. 69:239. 70. Ellis, N. R., C. S. Rothwell, and W. O. Pool, Jr. 1931. The effect of ingested cottonseed oil on the composition of body fat. J. Biol. Chem. 92:385. 71. Ellis, N. R., and J. H. Zeller. 1930. The influence of a ration low in fat upon the composition of the body fat of hogs. J. Biol. Chem. 89: 185. 72. Ellis, R., W. I. Kimoto, J. Bitman, and L. F. Edmondson. 1974. Effect of induced high linoleic acid and tocopherol content on the oxidative stability of rendered veal fat. J. Am. Oil Chem. Soc. 51 :4. 73. Economic Research Service. 1965. U.S. Food Consumption Stat. Bull. No. 364. U.S. Department of Agriculture, Washington, D.C. 74. Erwin, E. S., W. Sterner, and G. J. Marco. 1963. Effect of type of oil and site of administration on the fate of fatty acids in sheep. J. Am. Oil Chem. Soc. 40:344. 75. Evans, R. J., S. L. Bandemer, and J. A. Davidson. 1960. Fatty acid distribu- tion in lipids from eggs produced by hens fed cottonseed oil and cotton- seed fatty acid fractions. Poult. Sci. 39: 1199. 76. Faichney, G. J., PI. Lloyd Davies, T. W. Scott, and L. J. Cook. 1972. The incorporation of linoleic acid into the tissues of growing steers offered a dietary supplement of formaldehyde-treated casein-safflower oil. Aust. J. Biol. Sci. 25:205. 77. Feigenbaum, A. S., and H. Fisher. 1959. The influence of dietary fat on the

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Alteration of Fatty Acid and Sterol Composition in Lipids 229 incorporation of fatty acids into body and egg fat of the hen. Arch. Biochem. Biophys. 79:302. 78. Feeley, R. M., P. E. Criner, and B. K. Watt. 1972. Cholesterol content of foods. J. Am. Dietet. Assoc. 61 :134. 79. Ferguson, K. A., J. A. Hemsley, and P. J. Reis. 1967. Nutrition and wool growth. The effect of protecting dietary protein from microbial degrada- tion in the rumen. Aust. J. Sci. 30:215. 80. Fisher, H., and G. A. Leveille. 1957. Observations on the cholesterol, linoleic and linolenic acid content of eggs as influenced by dietary fats. J. Nutr. 63:119. 81. Ford, A. L., P. V. Harris, J. J. Macfarlane, R. J. Park, and W. R. Shorthose. 1974. Effeet of protected lipid supplement on organoleptie and other prop- erties of ovine muscle. Meat Research Report No. 2, CSIRO. Queensland, Australia. 82. Garton, G. A. 1969. Lipid metabolism of farm animals. In D. Cuthbertson, ed. Nutrition of Animals of Agricultural Importance. Part I. The Science of Nutrition of Farm Livestock. Pergamon Press, New York. 83. Garton, G. A., T. P. Hilditch, and M. L. Meara. 1952. The composition of the depot fats of a pig fed on a diet rich in whale oil. Biochem. J. 50:517. 84. Garton, G. A., and W. R. H. Duncan. 1954. Dietary fat and body fat: the composition of the back fat of pigs fed on a diet rich in cod-liver oil and lard. Bioehem. J. 57:120. 85. Goering, H. K., T. R. Wrenn, J. Bitman, L. P. Dryden, C. H. Gordon, and F. W. Douglas, Jr. 1973. Formaldehyde-easein protected by soy oil and cottonseed oil fed to lactating cows. J. Anim. Sei. 37:343. 86. Gooden, J. M., and A. K. Laseelles. 1973. Effeet of feeding protected lipid on the uptake of precursors of milk fat by the bovine mammary gland. Aust. J. Biol. Sei. 26:1201. 87. Guenter, W., D. B. Bragg, and P. A. Kondra. 1971. Effeet of dietary linoleie acid on fatty acid composition of egg yolk, liver, and adipose tissue. Poult. Sci. 50:845. 88. Harrap, B. S. 1973. Recent developments in the production of dairy products with increased levels of polyunsaturation. Aust. J. Dairy Technol. 28:101. 89. Harris, P. C., and F. H. Wilcox. 1963a. Studies on egg yolk cholesterol. 1. Genetic variation and some phenotypic correlations in a random bred population. Poult. Sci. 42:178. 90. Harris, P. C., and F. H. Wilcox. 1963b. Studies on egg yolk cholesterol. 3. Effect of dietary cholesterol. Poult. Sci. 42: 186. 91. Hendricks, H. 1974. The Drovers Journal, June 27, p. 10. 92. Herbert, L. S., and K. J. Kearney. 1975. The production of polyunsaturated tallows and their utilization in margarine manufacture. J. Food Technol. (In press). 93. Hilditch, T. P., and H. Jasperson. 1943. The influence of dietary fat of vary- ing unsaturation on the component acids of cow milk fats. Biochem. J. 37:238. 94. Hilditch, T. P., and J. J. Sleightholme. 1930. Variations in the component fatty acids of butter due to changes in seasonal and fasting conditions. Biochem. J. 24: 1098.

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