Dietary fat and the fatty acid composition of tissue lipids

Some characteristics of the fatty acid composition of animal tissue lipids are described and the origins of tissue fatty acids are discussed briefly. The effect of dietary fat on composition of tissue lipids is discussed. Types of dietary fatty acids for which experimental work is described include polyunsaturated fatty acids, short-chain fatty acids, fatty acids with chain length greater than C₁₈,trans unsaturated fatty acids, fatty acids with conjugated double bonds, acetylenic fatty acids, branched-chain fatty acids and oxygenated fatty acids. The individuality of fatty acids is discussed in relation to their roles as components of tissue lipids.     

Zusammensetzung und Anwendungen von Isostearinsäure

Composition and Application of Isostearic Acid The clay catalysed oligomerisation of unsaturated fatty acids yields C36 dimer fatty acids, C54 trimer fatty acids and C18 monomer fatty acids. Monomer fatty acids, which consists mainly of straight, branched, saturated and unsaturated fatty acids, can be distilled from the higher molecular weight products and after hydrogenation separated into solid stearic acid are mono- and polybranched C18 fatty acids whose branching points are mainly concentrated in the center of the molecule. Depending on the nature of the used raw materials and the degree of refinery, straight chain fatty acids, cyclic fatty acids, γ-lactones, unsaponifiable and even rosin acids are found as impurities. The low cloudpoint, comparable with oleic acid, as well as the excellent temperature- and oxidation stability gives isostearic acid and their derivatives excellent opportunities in applications as cosmetics, lubricants and plastics.     

Fatty acid chain length and degree of unsaturation are inversely associated with serum triglycerides

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.     

Metabolism of odd-numbered fatty acids and even-numbered fatty acids in mouse

Fatty acids are converted into energy via beta-oxidation. Although almost all natural occurring fatty acids are even-numbered, there are some odd-numbered fatty acids too. The details of the metabolism rate of odd-numbered fatty acids, however, are not clear. In the present study, we simultaneously administered a triacylglycerol containing four types of labeled even-numbered (palmitic acid and stearic acid) and odd-numbered (pentadecanoic acid and heptadecanoic acid) fatty acids to mice to compare the rates of their metabolism. The rates of metabolism were evaluated based on the accumulation of the labeled fatty acids in the small intestine epithelium, liver, and epididymal fat. Odd-numbered fatty acids accumulated mainly in the epididymal fat. In contrast, there was no accumulation of even-numbered fatty acids observed in the small intestine epithelium, liver, or epididymal fat. These results suggest that odd-numbered fatty acids might not be favorable substrates for beta-oxidation-related enzymes.     

气相色谱法测定食品油脂中的十八碳反式脂肪酸

反式脂肪酸是在油脂的加氢反应或高温精炼过程中伴随产生的一类不饱和脂肪酸,过多的食用这些成分可能会对人体健康产生危害。食品油脂中以十八碳反式脂肪酸最为常见。采用气相色谱法对食品中十八碳反式脂肪酸的检测进行了实验摸索,获得了一套准确度高、精确度好的方法,可应用于日常监督检测。     

Detection of 430 Fatty Acid Methyl Esters from a Transesterified Butter Sample

Milk fat is known to contain one of the highest number of fatty acids of all edible oils. Some of these fatty acids are known to be valuable (e.g. conjugated linoleic acids, furan fatty acid) and other as undesirable (e.g. saturated and some trans-fatty acids) food ingredients. However, a comprehensive picture on the presence of many trace fatty acids has not been achieved. For this reason we have developed an analysis scheme based on the conversion of the fatty acids into methyl esters. The fatty acid methyl esters were then fractionated by urea complexation. Both the filtrate of the urea complexation (~4 % of the sample weight) and the original sample were fractionated by high-speed counter-current chromatography (HSCCC). The resulting fractions were analyzed by GC/MS analysis. With this method 430 fatty acids were detected in one single butter sample. More than 230 fatty acids had two or more double bonds. In addition to the widely known spectrum of fatty acids we also detected a range of cyclohexyl fatty acids (five homologues) and methyl-branched fatty acids (including short chain and even-numbered anteiso-fatty acids), conjugated tetradecadienoic acids along with the novel ω-oxo-fatty acids (seven homologues). The reported relative retention time on the polar column may serve as a data base for the screening of other samples for this profusion of fatty acids.     

Use of acetyl chloride/methanol for assumed selective methylation of plasma nonesterified fatty acids results in significant methylation of esterified fatty acids

The albumin-bound nonesterified fatty acid pool in plasma, which represents a very small percentage of total plasma fatty acids, has previously been quantitated by a variety of methods. In the present study we determined that the nonesterified fatty acid concentrations in the plasma, quantitated by a popular method using acetyl chloride and methanol which is reported to be specific for methylation of nonesterified fatty acids in the presence of esterified fatty acids (i.e., without prior isolation of the plasma non-esterified fatty acids), were significantly overestimated due to cleavage and methylation of esterified fatty acids. Quantitation of the contaminating fatty acid from the esterified pool demonstrated that the amount of fatty acid cleaved from the esterified pool was enough to exceed the entire mass of nonesterified fatty acids. As an established method for comparison, we isolated nonesterified fatty acids from the plasma by thin-layer chromatography prior to methylation, using a number of simple precautions to limit oxidation. By performing all thin-layer chromatography steps in an atmosphere of nitrogen and by including fatty acid standards in the plasma with 0,1, 2 or 4 double bounds, we were able to accurately and reproducibly determine the concentration of nonesterified fatty acids in the plasma, including arachidonate. We demonstrated that no oxidation occurred in the thin-layer chromatographic isolation of homonesterified fatty acids and that the coefficients of variation for repeat measurements of the same sample were <11% using our reference method. Our data indicate that the use of acetyl chloride and methanol for assumed selective methylation of plasma nonesterified fatty acids results in significant methylation of esterified fatty acids.     

Produkte der Dimerisierung ungesättigter Fettsäuren XII: Die Dimerisierung von Konjuensäure

Products of Dimerisation of Unsaturated Fatty Acids XII: The Dimerisation of Conjugated Fatty Acids Dimeric fatty acids obtained by the clay-catalyzed dimerisation of the conjugated fatty acid (mixture of 9,11-octadecadienoic acid and 10,12-octadecadienoic acid) can be separated via HPLC in form of their dimethylates in three fractions in accordance with results obtained by separation of dimeric fatty acids of linoleic acid. The first fraction of aromatic dimeric fatty acids with the molecular weight 586 mainly contains compounds with a tetrasubstituted ring system. The second fraction, consisting of alicyclic unsaturated dimeric fatty acids, is characterized by the molecular weight 590 and a cyclohexene ring system. The third fraction corresponds to alicyclic saturated dimeric fatty acids. Dimeric fatty acids resulting of a Diels-Alder-reaction were detected neither in the end products nor as products in the early phase of the dimerisation. The results obtained by the investigation of the dimerisation of conjugated fatty acids are similar to those of the dimerisation of linoleic acid. Consequently a Diels-Alder-reaction is not involved in the formation of dimeric fatty acids. Although conjugated fatty acids are predominated to undergo a Diels-Alder-reaction no such products could be detected. This result strengthens the thesis that the dimerisation of unsaturated fatty acids is initiated by a cationic mechanism. The composition of the dimeric fatty acid using conjugated fatty acids is more uniform than that of usual mixtures of linoleic and linolenic acid. This provides evidence that a modification of the educt fatty acids can yield new structures of the dimerisation products.     

Fatty acid chain length combinations in ascitic fluid triglycerides containing lymphatic absorbed medium-chain fatty acids

Information on the fatty acid chain length combinations in lymph triglycerides containing medium-chain fatty acids was obtained combining the fatty acid composition and the carbon number composition of triglycerides from ascitic fluid of patients on medium-chain triglyceride-containing diets. In these triglycerides, the major part of the medium-chain fatty acids was present in combination with long-chain fatty acids. These results indicate that part of the lymphatic absorbed medium-chain fatty acids are absorbed as triglycerides which also contain long-chain fatty acids.     

Intake of ruminant versus industrial trans fatty acids and risk of coronary heart disease – what is the evidence?

Several studies have reported a positive association between intake of trans fatty acids and risk of heart disease. It has been suggested that trans fatty acids from ruminant sources are less detrimental than trans fatty acids from industrial sources. Legislation or advice on limiting trans fatty acids has, in some instances, been restricted to trans fatty acids from industrial sources. However, comparisons of ruminant and industrial trans fatty acids have been based on few studies using relative intake data (e.g. quintiles of intakes). Therefore, we have reviewed data describing the associations between absolute intake (g eaten per day) of ruminant and industrial trans fatty acids and risk of coronary heart disease, and examined the associations graphically. Where direct comparison is possible, there are no differences in risk of coronary heart disease between total, ruminant and industrial trans fatty acids for intakes up to 2.5 g/d. At higher intakes (more than 3 g/d) total and industrial trans fatty acids are associated with an increased risk of coronary heart disease but there is insufficient data available on ruminant trans fatty acids at this level of intake. The scarce data do not support discrimination between ruminant and industrial trans fatty acids in dietary recommendations or legislation.     

Fatty acid composition of the cellular slime mold Polysphondylium pallidum

The cellular slime mold Polysphondylium pallidum was grown upon Escherichia coli B/r, and the fatty acid compositions of total lipids obtained from vegetative amebae and aggregation-competent cells were compared. Fatty acids isolated from vegetative cells included C-17 and C-19 cyclopropane fatty acids and also straight-chain, saturated fatty acids. The cyclopropane fatty acids were derived from the ingested bacteria. Development of amebae to aggregation-competent cells was accompanied by a substantial decrease in saturated cyclopropane fatty acids and a concomitant increase in unsaturated fatty acids and unsaturated cyclopropane fatty acids, mostly as 18∶3 (5,9,12). We report here the fatty acid composition and identify the occurrence of Δ5 desaturation of cyclopropane fatty acids, namely, 9,10-methylene 5-hexadecenoic acid and 11,12-methylene 5-octadecenoic acid. These fatty acids have not been reported previously in the related species Dictyostelium discoideum, which also feeds on E. coli B/r and has Δ5-desaturation activity.     

Changes of fatty acid composition of phospholipids in liver mitochondria and microsomes of the rat during growth

The fatty acid patterns of rat liver mitochondrial and microsomal phospholipids were analyzed from term fetuses, 1 and 4 days old, and adult rats. The main fatty acids of phosphatidylethanolamine and-choline were stearic and palmitic acids, although the patterns differed slightly. The fatty acid composition of corresponding phospholipids in mitochondria and microsomes was similar. The fatty acid pattern of cardiolipin was dominated by linoleic acid. The most consistent feature of the developmental changes in the fatty acid patterns of all phospholipids studied was a decrease in the relative amount of monounsaturated fatty acids. The percentages of saturated fatty acids in phosphatidyl-ethanolamine and-choline increased during neonatal development. It is suggested that the high levels of fetal monounsaturated fatty acids were due to low availability of polyunsaturated fatty acids.     

代谢工程改造酵母生产多不饱和脂肪酸的研究进展

多不饱和脂肪酸因其在食品和医药领域的广泛作用而得到人们极大的关注,当前利用微生物发酵生产多 不饱和脂肪酸具有诸多优点,由于酵母生产迅速且生物量较高,利用酵母生产多不饱和脂肪酸已成为人们关注 的热点。本文综述了代谢工程改造酵母生产多不饱和脂肪酸的研究进展,以常规酵母-酿酒酵母和非常规酵母- 解脂耶氏酵母为例,介绍了酵母菌中多不饱和脂肪酸的代谢途径、酵母产油脂的生化机制、代谢工程改造酵母 产多不饱和脂肪酸以及不饱和脂肪酸积累对酵母耐受性的影响。以后研究工作的重点是进一步加强对酵母生产 多不饱和脂肪酸的机理研究,并以此为来指导代谢工程改造酵母生产多不饱和脂肪酸。     

Fatty acid composition of carotenoid esters in soybean and rapeseed oils

The amounts of the different carotenoids (lutein, lutein monoesters and diesters) in soybean and rapeseed oil were determined through a combination of column chromatography and UV spectrometry. The lutein diesters in the oils have been isolated by a combination of column and thin layer chromatography. Identification and determination of the amount of the various fatty acids of the lutein diesters have been carried out by means of gas chromatography after transesterification of the fatty acids to their methyl esters. Comparison of the fatty acids of the lutein diesters with those of the triglycerides of the oils revealed a striking difference. First, the fatty acids of the lutein diesters have shorter chains than the triglycerides acids. Secondly, the lutein fatty acids are more saturated than the fatty acids of the triglycerides of the corresponding oils. However the amount of linoleic acid in the case of the fatty acids of the lutein diesters in rapeseed oil is greater than that in the fatty acids of the triglycerides in rapeseed oil. Deceased, October 26, 1971.     

DC-Trennung von Ricinusölfettsäure-Partialglyceriden

Thin-Layer Chromatographic Separation of Partial Glycerides of Castor Oil Fatty Acids Partial glycerides of castor oil fatty acids and hydrogenated castor oil fatty acids were prepared by esterification or glycerolysis and fractionated, together with commercial products, by TLC (especially by two-dimensional technique) on silicagel 60 precoated plates. By comparison of the two-dimensional chromatograms of the partial esters of castor oil fatty acids with synthetic standards, such as partial glycerides of ricinoleic, di- and tri-ricinoleic acids, estolides of castor oil fatty acids esterified to partial glycerides, and partial esters of castor oil fatty acids with 1,3-propanediol, the substances that could be identified were partial glycerides of ricinoleic, diricinoleic and triricinoleic and tetraricinoleic acids as well as partial glycerides, which contained, in addition to ricinoleic, diricinoleic and triricinoleic acids, fatty acids without hydroxyl groups as terminal estolide chain. The TLC enables an insight into the complex character of the glyceride composition of partial glycerides of castor oil fatty acids.     

A quantitation problem in the open tubular gas chromatography of fatty acid esters from cod liver lipids

Methyl esters of fatty acids of marine origin contain large amounts of highly unsaturated long-chain fatty acids. It is shown that, although esters of saturated and monounsaturated fatty acids can be quantitatively analyzed on open tubular columns with a flame ionization detector there are serious losses of the long-chain highly unsaturated fatty acids of marine oils on the column. Through comparison of chain-length composition and iidine value some correction factors are suggested for the highly unsaturated fatty acids which permit reasonably accurate analyses.     

Comparison of catabolism rate of fatty acids to carbon dioxide in mice

The catabolism rates of a medium chain fatty acid (octanoic acid), an even‐numbered fatty acid (palmitic acid), and odd‐numbered fatty acids (pentadecanoic acid and heptadecanoic acid) in mice were compared using stable isotope (¹³C) labeled fatty acids and isotope‐ratio MS (IRMS). The catabolism rates of respective fatty acids were evaluated by the ratio of ¹³C and ¹²C in carbon dioxide expired from mice. The results show that the catabolism rate of octanoic acid is three times faster than that of palmitic acid. This result is in agreement with previous knowledge that medium chain fatty acids are easily beta‐oxidized as compared to long chain fatty acids. The catabolism rates of odd‐numbered fatty acids such as pentadecanoic acid and heptadecanoic acid were significantly lower as compared to those of even‐numbered fatty acids such as palmitic acid. This finding supports our previous report that odd‐numbered fatty acids are easily accumulated into body fat. The high accumulation of odd‐numbered fatty acids in body fat would be a direct result of their low beta‐oxidizability. Practical applications: ¹³C‐labeled fatty acids were administered to mice and the rates of ¹³CO₂ formation were compared among medium chain, even‐numbered, and odd‐numbered fatty acids using IRMS. We found that the catabolism rates of odd‐numbered fatty acids such as pentadecanoic acid and heptadecanoic acid were significantly lower in comparison to those of even‐numbered fatty acids such as palmitic acid. These findings could be valuable for the development of the lipid metabolism field.     

Different metabolism of saturated and unsaturated long chain plasma free fatty acids by intestinal mucosa of rats

During fat absorption, unsaturated long chain fatty acids are esterified at a higher rate than saturated fatty acids of similar chain length. This phenomenon has been attributed to differences in the binding affinity of fatty acids to a cytosolic fatty acid-binding protein. As intestinal mucosa utilizes plasma free fatty acids as well, we investigated whether long chainplasma free fatty acids of different degree of saturation are metabolized also at different rates.³H-Palmitic and¹⁴C-linoleic acid complexed to rat serum were injected rapidly into a tail vein of fasting rats. One, 2 and 4 min later there was no difference between³H and¹⁴C-radioactivity in intestinal mucosa, suggesting equal initial uptake of the two labeled fatty acids from plasma. Despite their equal uptake, the incorporation of the isotopes into ester lipids was significantly different, however: at 2 min, 53.1±3.9% of³H and 73.8±4.6% of¹⁴C were recovered in ester lipids. Phospholipids and triglycerides accounted for most of the mucosal³H and¹⁴C. At 4 min, a similar distribution of isotopes in intestinal mucosal metabolites was found. These data show that despite equal initial uptake by intestinal mucosa unsaturated long chain fatty acids taken up from plasma are esterified to a higher and oxidized to a lower extent than saturated plasma free fatty acids. Unsaturated plasma free fatty acids, therefore, may provide a more important source of fatty acids for endogenous intestinal lipoprotein lipids than saturated plasma free fatty acids. It is speculated that the fatty acid binding protein might be operative not only in the intracellular transport and metabolism of luminal fatty acids but of plasma free fatty acids as well.     

Fatty Acids of Soyabean Phosphatides and Glycerides with Special Reference to the Oxidised Fatty Acids

The fatty acid composition of the triglycerides, glycerophospholipids and glycophospholipids of soyabean was compared. The fatty acids of the glycophospholipids, which are derivatives of phytosphingosine, are composed of 80% α-hydroxy long chain acids (chain length >18) and 20% non-substituted fatty acids, about two third of which were long chain ones. The glycerides and the glycerophospholipids contained only about 1% each of oxidised and long chain fatty acids. Among the oxidised fatty acids of the glycerides and glycerophospholipids some hydroxy acids were found, which carried the hydroxy group not at the α-position, but rather in the middle of the chain. All the fatty acids of the glycophospholipids were - contrary to the fatty acids of the glycerides and glycerophospholipids - completely saturated and include appreciable amounts of odd numbered components.     

n−3 polyunsaturated fatty acids and coronary thrombosis

Studies of Greenland Eskimos showed that a very high intake of marine n?3 fatty acids markedly inhibited platelet reactivity and suggested that intake of these fatty acids might prevent coronary thrombosis. Later studies with lower, more practical doses of n?3 fatty acids also have shown a platelet inhibitory effect of n?3 fatty acids, albeit fairly marginal. Furthermore, n?3 fatty acids have little effect on measures of blood coagulability and may slightly decrease fibrinolysis. In animal models, n?3 fatty acids often have been shown to inhibit thrombosis, but again the doses have tended to be very high. Finally, there has been little effect of (low-dose) n?3 fatty acids in clinical trials in humans on the incidence of myocardial infarction. Overall, there is little evidence for a major antithrombotic effect of practical doses of n?3 fatty acids on coronary thrombosis. This does not exclude a beneficial effect of n?3 fatty acids on coronary heart disease as suggested from clinical trials, but the major effect may be antiarrhythmic rather than antithrombotic.