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1.
The maize triglycerides were resolved into species by silver nitrate thin layer chromatography. The distribution of the fatty acids among the 1, 2 and 3 positions of each triglyceride species was determined by stereospecific analysis. From these data the relative amounts of each positional isomer were calculated. The results indicate that esterification of the fatty acids at each position proceeds with a specificity that is correlated with the composition of the other positions of the triglyceride.  相似文献   

2.
Slakey SP  Lands WE 《Lipids》1968,3(1):30-36
The fatty acid compositions at the 1-, 2-, and 3-positions3 of rat liver triglycerides were determined by using pancreatic lipase and diglyceride kinase. The distribution of acids between the 1- and 3-positions is not random; rather each position has a characteristic composition. The relative abundance of species and positional isomers in the triglyceride mixture was predicted by using values from the stereospecific analysis and assuming that the composition of each position is independent of the other two. The total triglyceride was resolved into species by using TLC with silver nitrate and Silica Gel G, and the relative amounts corresponded closely with those predicted on the basis of this assumption. The major species were isolated, and the distribution of their fatty acids among the three glyceride positions was determined. From these data the relative amount of each positional isomer was calculated. The results indicate that the esterification of fatty acids at each position proceeds with a specificity that is not correlated with the composition of the other positions with the molecule. The relative abundance of the different liver triglyceride species is also found to be related in part to the composition of the 1,2-diglyceride units found in the lecithins of this tissue. Presented at the AOCS Meeting, Philadelphia, October 1966.  相似文献   

3.
W. W. Christie  J. H. Moore 《Lipids》1970,5(11):921-928
Forty-five triglyceride samples with a wide range of fatty acid compositions were selected from a large number of pig adipose tissue samples (inner and outer back fats and perenephric fat) available from nutritional experiments. These samples were subjected to stereospecific analysis to determine the changes occurring in the positional distribution of the component fatty acids. The oleic acid content of the triglycerides was taken as the standard of comparison and as this increased, the proportions of the other unsaturated fatty acids also increased in a linear manner and the concentrations of the saturated components decreased proportionately. In position 1, the palmitic acid concentration remained constant while the stearic acid concentration decreased linearly and the concentrations of the unsaturated fatty acids increased. In position 2 the stearic acid concentration remained almost constant while the palmitic acid concentration decreased linearly in response to increases in the concentrations of the unsaturated acids. The least change occurred in position 3 where there were slight decreases in the concentrations of saturated acids as the concentrations of unsaturated acids increased. The precise quantitative relationships depended on the tissue examined. Constant proportions of the available myristic and palmitoleic acids were found in all three positions and constant proportions of the available stearic and oleic acids were found in position 1. These results are discussed in relation to possible pathways of triglyceride biosynthesis in pig adipose tissues.  相似文献   

4.
Dietary fats which were protected from ruminal metabolism were fed to ruminants, and the constituent fatty acids subsequently appeared in the glycerides of tissues and secretory products. These dietary fat induced alterations in tissue lipid composition were particularly apparent when the fat source was enriched with linoleic acid. Similarly, when pigs were fed linoleic-enriched fats, the linoleic acid was incorporated into the adipose tissue triglycerides. Stereospecific analyses were carried out on triglycerides from various tissues and secretory products obtained from animals fed control or linoleate-enriched diets. The analysis of adipose tissue triglycerides showed that linoleate and oleate were preferentially esterified to positions 2 and 3 (cattle and sheep), and positions 1 and 3 (pigs). Of the other major adipose tissue fatty acids, palmitate was preferentially esterified at position 1 (ruminants) and position 2 (pigs), and stearate was preferentially esterified at positions 1 and 3 (ruminants), and position 1 (pigs). Stereospecific analysis of high mol wt milk triglycerides showed that linoleate was either evenly distributed on all three positions (goats), or predominantly on position 3 (cows). Furthermore, the incorporation of this linoleate did not markedly alter the positional specificity of the other major milk triglyceride fatty acids. Of these fatty acids, the short and medium chain length acids (butyratelaurate) were mainly on position 3, myristate and palmitate on positions 1 and 2, and stearate and oleate evenly distributed. Thoracic duct lymph triglycerides from sheep tended to show preferential incorporation of linoleate at position 3, palmitate at position 2, and stearate at position 1 and 3; oleate, on the other hand, tended to be evenly distributed on all three positions of the lymph triglyceride. The stereospecific arrangement of fatty acids in sheep liver triglycerides was similar to that of lymph triglycerides, and this may reflect the uptake of intact or partially hydrolysed chylomicron and/or very low density lipoprotein triglycerides by the liver. There were also some analogies in the stereospecific arrangement of fatty acids on ruminant lymph and milk triglycerides and this may reflect an incomplete hydrolysis of chylomicron and/or very low density lipoprotein triglycerides prior to uptake by the mammary gland. An unusual feature of lymph from sheep fed linoleate was the presence of phospholipids which contained large amounts of linoleate in ca. equal proportion at both positions 1 and 2 of the phospholipid molecule.  相似文献   

5.
The Influence of Fatty Acids in Triglycerides on the Digestion of Dietary Fats by Pancreatic Lipase The digestion of dietary fats by pancreatic lipase was studied in in-vitro-experiments. We tested the following fats: coconut, butterfat, cocoabutter, lard and oil of corn germ. The breakdown of triglycerides was followed up by monitoring the free fatty acids and glycerol. Additionally we analyzed the fatty acid distribution by gas-liquid chromatography of triglycerides, 1,2-diglycerides and 2-monoglycerides. Fatty acids with a chain length from C10C20 were determined by gas chromatography. Short chain fatty acids were not regarded separately. As pancreatic lipase has a positional specificity for the 1- and 3-position of a triglyceride there is information on the distribution of fatty acids in fats and of their digestion by such experiments. For the resorption of the fatty acids it may be of a certain importance in which position it is esterified in the fat when it is hydrolysed in gut. The hydrolysis of fats used in these experiments was quite different. This can be explained by the fatty acid distribution, the chain length and by a varying rate of emulsification of fats in an aqueous phase.  相似文献   

6.
J. N. Roehm  O. S. Privett 《Lipids》1970,5(3):353-358
Soybeans of the Hawkeye variety were picked at eleven periods from 30 to 111 days after flowering and extracted with chloroform-methanol. The triglyceride fraction of five pickings, selected 35 to 91 days after flowering (when synthesis of lipid was most active), were isolated by silicic acid thin layer chromatography (TLC) and species composition determined using argentation TLC and lipase hydrolysis. The triglyceride content of the total lipid increased from 6.5% at 30 days after flowering to 85% in the mature bean (111 days). The major changes in fatty acid composition of the triglycerides occurred during the first 52 days after flowering. During this period linolenic acid decreased from 34.2% to 11.7%, the percentages of linoleic and oleic acids increased, stearic remained fairly constant and palmitic decreased slightly. Large quantitative changes occurred in the molecular species of the triglycerides of the bean during maturation; some triglycerides containing linolenic acid could not be detected approximately 66 days after flowering. Although changes occurred in the percentage and amount of each triglyceride species, the positional distribution of fatty acids remained virtually unchanged throughout maturation. Linolenic acid was distributed fairly uniformly between the β-position and the α-positions, linoleate favored esterification in the β-position, and oleate the α-positions. Most of the stearic and palmitic acids were esterified in the α-positions. The consistency of the positional arrangement of the fatty acids indicated that the mode of glyceride synthesis was established very early during maturation and molecular species composition was controlled by the fatty acids available for synthesis.  相似文献   

7.
Pistachio kernel oil has been analyzed by separating the triglycerides according to their degree of unsaturation by means of thin layer chromatography on silica gel plates impregnated with silver nitrate. The total fatty acids and the fatty acid on position 2 of each individual triglyceride were determined. The distribution of oleic acid on the different positions of triglycerides varies according to the unsaturation of these triglycerides. Oleic acid in the case of the less unsaturated triglycerides locates in the 2-position, and, as the degree of unsaturation increases due to linolenic or linoleic acids, it tends to be on external positions. Linoleic and linolenic acids usually are esterified in the middle position.  相似文献   

8.
Randall Wood 《Lipids》1975,10(7):404-408
Triglycerides from normal liver, host liver, and hepatoma of rats maintained on chow and fat-free diets were subjected to stereospecific analysis. Normal and host liver triglycerides from animals on the same diet did not exhibit significant differences. Fat-free diet reduced polyunsaturated fatty acids in normal and host liver triglycerides, but had no effect upon hepatoma triglycerides. Each position of hepatoma and liver triglyceride glycerol exhibited a characteristic fatty acid composition. Palmitate concentrations were reduced dramatically and stearate levels were increased significantly at the 1 position of hepatoma triglycerides, relative to the corresponding position of liver triglycerides which were affected little by diet or tumor. Except for higher percentages of C-20 and higher fatty acids, common to all three positions, the composition of hepatoma triglycerides at the 2 position appeared normal. The 3 position of hepatoma triglycerides contained significantly higher percentages of stearate than liver. Data obtained previously for Ehrlich ascites cell triglycerides were in good agreement with this hepatoma. Data from these two neoplasms suggest that the metabolic system that regulates or controls the fatty acid composition at the 1 and 3 positions of normal tissue triglycerides does not function normally in neoplasms.  相似文献   

9.
Peter W. Parodi 《Lipids》1982,17(6):437-442
Milk triglycerides from the echidna, koala, Tammar wallaby, guinea pig, dog, cat, Weddell seal, horse, pig and cow were subjected to fatty acid and stereospecific analysis to determine the positional distribution of the fatty acids in the triglycerides. The samples presented a wide range of fatty acids, most of which varied in content among species. The compositions of the acids at the 3 positions also varied among species, reflecting the content of these acids in the triglycerides. However, there was a general similarity in fatty acid positional distribution patterns for all the species with the exception of the echidna. The echidna exhibited a completely different fatty acid positional distribution pattern. The saturated acids were preferentially esterified at thesn-1-position whereas the unsaturated acids were selectively esterified at thesn-2-position. The triglyceride carbon number distribution of milk from the above species (with the exception of the Weddell seal) was determined by gas liquid chromatography and compared to that predicted by the 1-random-2-random-3-random fatty acid distribution hypothesis. Agreement was excellent between observed and predicted composition for echidna, koala, Tammar wallaby, guinea pig and pig milk, and agreement was reasonable for dog, cat, horse and cow milk. Results are discussed in relation to biochemical mechanisms.  相似文献   

10.
This is the first report of stereospecific analyses of plant triglycerides isolated from seeds of distinct genotypes rather than from commerically refined oils. Triglycerides from six maize inbreds were analyzed. The strains exhibited a wide range of fatty acid compositions (palmitic acid 7.8–19.1%, oleic acid 17.0–43.0%, linoleic acid 41.6–68.3%). The distribution of the fatty acids among the 1, 2 and 3 positions of the triglycerides was clearly nonrandom for all six strains. At the 2 position of the triglycerides over 98% of the fatty acids were unsaturated. More plamitic and stearic acids were found in position 1 than in 3. The general fatty acid pattern of maize triglycerides was similar to that found in most animal triglycerides.  相似文献   

11.
Evelyn J. Weber 《Lipids》1973,8(5):295-302
Kernels of corn inbred H51 were collected at five intervals after hand pollination. The triglyceride content of the total lipids increased from 8.6% at 10 days after pollination to 78.3% at 60 days. The most active period of triglyceride synthesis occurred from 20 to 45 days after pollination, when the weight of triglycerides per kernel increased from 1.1 to 7.5 mg. Over all the collection periods the percentages of palmitic, linoleic and linolenic acids decreased while oleic acid increased, but from 30 to 60 days after pollination the fatty acid composition of the triglycerides was nearly constant. Stereospecific analysis revealed a general fatty acid pattern for the triglycerides, in which the concentration of the saturated acids was highest in position 1, linoleic acid in 2 and oleic acid in 3. From 20 to 60 days after pollination there was little change in the fatty acid composition at the 1 position, but the largest changes occurred at the 3 position where palmitic and oleic acids decreased 5.1% and 7.3%, respectively, and linoleic acid increased 13.4%. The variations in the molecular species of the triglycerides were determined by silver nitrate thin layer chromatography and were found to be small from 20 to 60 days after pollination, except for an increase in trilinolein from 5.2 to 11.9%. Stereospecific analyses of four major triglycerides species, SMD, M2D, SD2, and MD2, revealed larger changes in fatty acid distribution at individual positions during maturation than were apparent from analyses of the total triglycerides. Presented in part at the AOCS Meeting, Ottawa, September 1972.  相似文献   

12.
Phylogeny of lipase specificity   总被引:6,自引:0,他引:6  
Lipase preparations from 19 animal species, representing nine of the animal phyla, were studied. Acetone powders were prepared from the pancreas, hepatopancreas, gastrointestinal tract or whole animal, and the preparations were screened for lipolytic activity by tributyrin agar clearing. The pH optimum of each preparation was determined by using both tributyrin and corn oil emulsions. The positional specificity at the pH optimum of each lipase preparation was determined from the fatty acids released by a 2–5 min reaction with cocoa butter and lard. The vertebrate lipases behaved analogously to hog pancreatic lipase by showing a high specificity for the 1 and 3 positions of long chain triglycerides. Invertebrate preparations that did hydrolyze long chain triglycerides did so randomly, with no strong positional or fatty acid specificity. Journal Paper No. J-6311 of the Iowa Agriculture and Home Economics Experiment Station, Ames, Iowa, Project 1517. Presented at the AOCS-AACC Joint Meeting, Washington, D.C., April 1968.  相似文献   

13.
The positional distribution of fatty acids in the choline and ethanolamine phosphoglycerides of the L1210 murine leukemia cells was determined and compared to that of normal mouse lymphocytes. The major phospholipids of both cell types had appreciable degrees of positional specificity as evident from the higher percentage of saturated fatty acids in position 1 and of polyunsaturated fatty acids in position 2. The L1210 cells had less arachidonate and more linoleate in position 2 of choline and ethanolamine phosphoglycerides as compared to the normal lymphocytes. However, there were similar proportions of saturated, monoenoic and polyenoic fatty acids in positions 1 and 2 of the phospholipids of the L1210 leukemia cells and the lymphocytes. These data demonstrate that fatty acid positional specificity is retained in the major phospholipids of this rapidly growing tumor.  相似文献   

14.
Randall Wood  John Falch 《Lipids》1974,9(12):979-986
Minimal deviation hepatoma 7288C cells were cultured in a modified Swim's medium supplemented with decreasing levels of serum, lipid-free serum, lipid-free serum plus fatty acids, and other additives. Cellular and media neutral lipid classes were quantitated, the fatty acids of triglycerides and sterol esters analyzed, and the carbon number distribution of triglycerides determined. Cellular triglyceride biosynthesis virtually was inhibited when the medium was supplemented with bovine serum alone. This inhibition was not observed when the medium was supplemented with fetal calf serum alone or mixtures of fetal calf serum and bovine serum. Cells cultivated on medium supplemented with lipid-free serum plus palmitic or linoleic acids had much lower levels of free and esterified cholesterol. The fatty acid composition of cellular triglycerides and cholesterol esters differed dramatically from the corresponding media lipid classes. Except when linoleic acid was added to the medium, changes in the media serum and lipid levels had only marginal effects upon the fatty acid composition of cellular triglycerides and cholesterol esters. These data, in conjunction with earlier data that showed the media neutral lipid levels did not decrease during cell growth, indicate that these hepatoma cells utilize little or no serum triglycerides and cholesterol esters. Linoleic acid added to the medium dramatically reduced the level of 18∶1 acids in cellular triglycerides and cholesterol esters. Palmitic acid added to the medium did not change the fatty acid compositions significantly. Comparison of experimentally determined and calculated triglyceride carbon number percentages indicated a random distribution of fatty acids in this glyceride. The fatty acid composition of cellular triglycerides was similar to the composition of the cholesterol esters. The lack of characteristic and distinguishable compositions of these two classes that occur in most normal tissues suggests a loss of specificity in the lipid metabolism of this neoplasm at the class level.  相似文献   

15.
Pork, enriched in linoleic acid content, was compared with conventional pork in the diet of three human subjects with respect to the plasma cholesterol concentration and the excretion in feces of neutral sterols and bile acids. Since the fatty acids in pork glyceride have an unusual positional distribution, the redistribution that might occur during the absorption and disposition of a fat meal was also studied. The plasma cholesterol was lower with polyunsaturated pork, the difference, 14 mg/100 ml plasma, being of the order expected from the change in polyunsaturated to saturated fatty acid ratio. On average, the excretion of neutral sterols was 57% greater with polyunsaturated than with conventional pork in all three subjects, and in this respect the results resembled the findings with polyunsaturated ruminant fats. During the absorption of pork fat, the high proportion of palmitate in the 2 position of lard triglyceride served as a useful marker, since human triglyceride carries mainly unsaturated fatty acids in that position. There were stepwise changes in the fatty acid composition at the 2 position of triglyceride as the fat was absorbed, transported through, and cleared from plasma, the palmitate being gradually replaced by oleate and linoleate. By contrast, the total fatty acid profile in the triglyceride changed relatively little, implying selective reacylation with palmitate at the 1 and/or 3 position. During the clearing of dietary triglyceride, the porcine triglyceride was thus converted to the form occurring in humans.  相似文献   

16.
Sampugna J  Jensen RG 《Lipids》1968,3(6):519-529
A procedure is described for determining the stereospecific structure of triacid triglycerides containing oleic acid. The method utilizes the unique specificity of the lipase system fromGeotricum candidum for hydrolyzing fatty acids which containcis-9-unsaturation.The procedure involves a pancreatic lipase hydrolysis of 10-20 mg of substrate to determine the fatty acids in the beta-position and the incubation of another 50 mg of triglyceride withG. candidum lipase to obtain diglyceride for further treatment. The alpha,alpha- and alpha,beta-diglycerides are collected separately, converted to phenyl phosphatides and treated with phospholipase A. The analysis of the monoglycerides, produced with pancreatic lipase and the analysis of the beta-lysophosphatides allows the determination of the ratios of the original 2 position oleic acidsn-triglycerides while the analysis of the alpha-lysophosphatides aids in the determination of the originalsn-triglycerides which contained oleic acid in the 3 position. The 1 position oleic acidsn-triglycerides are calculated by difference.Racemic and enantiomeric triglycerides containing palmitic, stearic and oleic acids were synthesized and used to establish the limits of the new method. The good agreement between the actual and observed values for a mixture of isomers indicates that the procedure will be useful in the analysis of triacid triglycerides which contain oleic acid. The application of the procedure to triacid triglycerides which contain other unsaturated fatty acids is discussed.  相似文献   

17.
Grimsgaard S  Bønaa KH  Bjerve KS 《Lipids》2000,35(11):1185-1193
Little is known about the association between dietary fatty acids and serum triglyceride concentrations. Plasma fatty acids may reflect dietary intake and can be used to study the relationship between concentrations of individual fatty acids and serum lipids. We examined the cross-sectional relationship of plasma fatty acids with serum nonfasting triglyceride and total cholesterol concentrations. Relative concentrations of individual plasma phospholipid fatty acids were determined by gas-liquid chromatography among 4,158 men aged 40–42 yr, who participated in a population study. The pattern of associations between individual fatty acids and cholesterol was different from that between individual fatty acids and triglyceride concentrations. All fatty acids displayed positive associations with total cholesterol concentration except linoleic acid, which was inversely related to cholesterol. In contrast, associations between individual fatty acids and triglyceride concentrations differed in strength and direction depending on both carbon chain length and the degree of unsaturation. Concentrations of very long chain (20 carbon atoms or more) saturated, monounsaturated, and n-3 polyunsaturated fatty acids showed significant inverse associations with triglycerides, whereas shorter fatty acids within these classes were positively associated with triglyceride concentrations. The present data suggest that the associations between concentrations of serum triglycerides and plasma phospholipid fatty acids depend on both fatty acid chain length and the degree of unsaturation.  相似文献   

18.
I. M. Morrison  J. C. Hawke 《Lipids》1977,12(12):1005-1011
A stereospecific distribution of fatty acids in bovine milk fat containing 15.5% linoleic acid has been compared with the distribution in bovine milk fat containing a normal level (1.8%) of linoleic acid. The positional distribution was obtained by the separate analysis of milk fat triglycerides of high, medium, and low molecular weight. The order of preference for linoleic acid in the high molecular weight triglycerides was position 3>position 2 >position 1. There was an accompanying altered distribution of myristic acid and palmitic acid in favor of position 1 at the expense of position 3. However, the proportions of myristic acid and palmitic acid in position 2, relative to positions 1 and 3 were identifical in the high molecular weight fractions of the two milk fats. The distribution of linoleic acid in the medium molecular weight triglycrides of linoleic-rich milk fat was position 1=position 2>position 3. This resulted in a change in the distribution of 18 carbon monounsaturated fatty acids in favor of position 2 at the expense of position 1, but the distribution of myristic acid and palmitic acid was virtually unaltered. The distribution of linoleic acid in the low molecular weight triglycerides was position 2>position 1>position 3. The amounts of myristic acid and palmitic acid in position 2 and of palmitic acid in position 1 decreased in the low molecular weight triglycerides of the milk fat containing elevated levels of linoleic acid. Changes in the distribution of fatty acids which were observed in the separate analysis of the high, medium, and low molecular weight triglycerides were not apparent when comparing the distribution in the total milk fats. For example, the distribution of myristic acid and palmitic acid appeared to be unchanged, while the distribution of 18 carbon monounsaturated fatty acids was slightly altered in favor of positions 2 and 3. Moreover, linoleic acid showed an almost equal preference for the three positions of the glycerol moiety in milk fat containing elevated levels of this fatty acid with some concentration at position 2.  相似文献   

19.
The serum fatty acid profiles of patients receiving either intravenous medium or long chain triglycerides were studied. Seventeen hospitalized patients, dependent on total parenteral nutrition, were randomly enrolled into a prospective study. The total parenteral nutrition (TPN) delivered amino acids and glucose and either a 75% medium chain triglyceride and 25% long chain triglyceride (MCT group) physical mixture or all long chain triglyceride (LCT group), as the respective fat sources. The amino acids and glucose were given continously, and the lipid was given for 10 hours each day over five days. Fatty acid profiles on serum triglycerides and free fatty acids were done in the morning before any lipid was given and also later in the afternoon, near the end of the lipid administration, on days 1, 3 and 5. Medium chain fatty acids rose quickly in the triglyceride fraction in patients given MCT. Rapid MCT hydrolysis occurred as evidenced by the appearance of medium chain fatty acids in the free fatty acid fraction in the afternoon sampling. Clearance of the hydrolyzed medium chain free fatty acids (MCFFA) occurred so that little, if any, were present in the morning sampling one day later. Long chain fatty acids, as either triglycerides or free fatty acids, showed expected increases during the daily infusion, but not of such relative magnitude as the medium chain fatty acids. Medium chain fatty acid incorporation into the phospholipid or cholesterol ester fractions by the end of the five-day feeding period was present but minimal. As opposed to conventional long chain triglycerides, intravenously administered medium chain triglycerides are hydrolyzed and cleared rapidly and do not accumulate in other lipid fractions, and are therefore a more readily available lipid fuel.  相似文献   

20.
J. R. Couch  A. E. Saloma 《Lipids》1973,8(7):385-392
Hens were fed a practical diet supplemented and unsupplemented with 5% menhaden oil and a synthetic fat-free diet for a period of 90 days. Egg yolks from hens fed each of the three diets were analyzed for fatty acid composition and positional distribution of the fatty acids by successive chromatographic techniques. The triglycerides were resolved into fractions containing, 0, 1, 2 and 3+ double bonds per molecule. Each of these types was quantitated and analyzed for fatty acid distribution. The positional distribution was determined with the aid of pancreatic lipase hydrolysis. The feeding of the practical diet supplemented with 5% menhaden oil produced an increase in the 14∶0 acid in the intact triglycerides, 2-monoglycerides and 1,3-diglycerides with the majority of this acid being bound in the 1,3 positions. In the monounsaturated triglycerides the 16∶0 acid was linked predominantly at the 1,3 positions. The feeding of the fat-free diet produced a decrease in the 16∶1 acid content of the egg yolk lipids in the monounsaturated series, in the intact triglycerides, the 2-monoglycerides and the 1,3-diglycerides. The 18∶0 acid was linked more often at the 1,3 positions than at the 2 position, and was not affected by the diet consumed by the hens. Hens fed the fat-free diet produced more monounsaturated and diunsaturated triglycerides than those fed the other diets. Linoleic acid exhibited the greatest degree of preference for the 2 position, which was followed in turn by oleic acid. All other major acyl components were found to be preferentially esterified at the 1,3 positions. The difference observed in the fatty acid composition of egg yolk neutral and polar lipids was attributable to the fatty acid content of the diet. In the case of the oleic and linoleic acids, there was less variation in the saturated fatty acid content, which could be traced to the type of diet fed.  相似文献   

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