Lipid metabolism of the yellow clam,Mesodesma mactroides: 3-Saturated fatty acids and acetate metabolism

The fate of labeled palmitate, stearate, and acetate administered to the yellow clam,Mesodesma mactroides, was investigated. 1-¹⁴C palmitic and 1-¹⁴C stearic acids were oxidized to CO₂ to a limited extent. They were mainly incorporated in diacylglycerols and triacylglycerols and were converted to higher homologs. After administration, palmitic acid was converted to stearic and oleic acids, whereas administered stearic acid was converted to 18∶1, 18∶2, 20∶1, and 20∶2 acids. Labeled acetate was readily included by the clam in 12∶0, 14∶0, 14∶1, 15∶0, 16∶1, 16∶1, 16∶2, 18∶2, 18∶1, 18∶2, 20∶1, 20∶2, and 20∶3 acids.     

Lipid metabolism of the yellow clam,Mesodesma mactroides: 2-Polyunsaturated fatty acid metabolism

The fate of labeled linoleic, α-linolenic, and higher homologs of α-linolenic acid administered to the yellow clam,Mesodesma mactroides, was investigated. It was found that the clam incorporated the acids dissolved in sea water and converted 18∶2 (n−6) into 20∶2 (n−6) and 18∶3 (n−3) into 18∶4 (n−3) and 20∶3 (n−3). The addition of casein hydrolysate to the sea water increased the desaturation capacity of the clam and allowed the conversion of 18∶2 (n−6) into 18∶3 (n−6) to be demonstrated. An enhanced desaturation of 18∶3 (n−3) into 18∶4 (n−3) was also demonstrated. After 12 hr administration of the acid, no radioactivity was found in arachidonic, 20∶5 (n−3), or 22∶6 (n−3). Feeding the clams a culture ofPhaeodactylum tricornutum previously incubated with 1-¹⁴C-α-linolenic acid demonstrated that all the homologs of the α-linolenic series were found in the clam without any important changes. Six hour administration of labeled linolenic acid resulted in the incorporation of the acid into diglycerides and phospholipids. Member of the carrera del Investigador Cientifico of the Consejo Nacional de Investigaciones Cientificas y Tecnicas     

Lipid metabolism of the yellow clam,Mesodesma mactroides: I. Composition of the lipids

The lipid composition of the yellow clam,Mesodesma mactroides, that lives in the northern beaches of the Buenos Aires province of Argentina was studied. The main nonpolar lipids are triglycerides and alkoxyglycerides. Phosphatidyl choline, phosphatidyl ethanolamine, and phosphatidyl serine are the main phospholipids. The predominant fatty acids are 16∶0, 16∶1ω7, 18∶0, 18∶1ω9, 20∶5ω3, and 22∶6ω3. The are mainly provided by the clam's food and stored in the hepatopancreas. The content of polyunsaturated acids increases in summer together with an increase in nonpolar lipids and is correlative with an increase in phytoplankton in the sea water. Sexual maturity modifies the lipid composition of gametes.     

The metabolism of polyenoic fatty acids

Feeding experiments with C¹⁴-labeled and unlabeled unsaturated fatty acids have been used to study the possible routes of formation of the C₂₀- and C₂₂-polyenoic fatty acids of rat liver phosphatides. The acids of the palmitoleate, oleate, linoleate, and linolenate types (considered on the basis of the position of the double bond closest to the methyl end) are apparently formed from the C₁₆ and C₁₈ unsaturated acids of the corresponding types. The results rule out possible transformations of the C₂₀- and C₂₂-polyenoic acids from one type to another, and demonstrate the exclusive introduction of new double bonds toward the carboxyl group. Isomers of linoleate or linolenate in which the double bonds were shifted by one carbon atom toward the carboxyl or methyl groups were incorporated into the phosphatides only to a negligible extent in the form of polyenoic acids.     

Reduction of unsaturated fatty acids and fatty alcohols with diimide from hydroxylamine-ethyl acetate

Hydroxylamine has been recently found to react with ethyl acetate to generate diimide in situ. This reaction was used to reduce 10-undecenoic, oleic, linoleic, stearolic, concentrates of ricinoleic, cyclopentene and cyclopropene fatty acids (FA), dehydrated castor oil FA, 10-undecen-1-ol, oleyl alcohol and castor fatty alcohols. Unsaturated FA and their corresponding alcohols reacted in a similar manner. Terminally unsaturated, cyclopropene and cyclopentene FA were more reactive than oleic acid, which, in turn, was more reactive than hydroxymonoenoic acids. Conjugated dienoic FA reduced faster than nonconjugated dienoic acids. Partial hydrogenation using this reagent is particularly advantageous in determining geometry and the position of double bonds in the polyunsaturated FA, as it can be carried out in the absence of oxygen or oxidizing agents unlike hydrazine reductions.     

Potential synthetic lubricants: Esters of C18-saturated cyclic acids

A series of 16 esters of C₁₈-saturated cyclic acids (HCal) were prepared, and partial evaluation showed that several have qualities that recommend them as potential low-temp lubricants. Starting materials used were primary, straight, and branched chain alcohols C₄–C₇; perfluoro alcohols; phenol; cyclohexanol; and C₁₈-saturated cyclic alcohols prepared from cyclic acids. Viscosities were measured at −40, 100, and 210F. Their viscosity indexes ranged from 26 to 143. Pour points or melting points of the esters ranged from −27 to −96F. The oxidative stability of these esters measured at 347F according to a modification of the test method for military specification MIL-L-7808 was in nearly all cases equal or superior to the control bis-2-ethylhexyl sebacate. More severe oxidation tests showed the esters of HCal to be slower than the control in the development of acidic decomposition products. Presented at AOCS meeting, New Orleans, La., April 1964. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA.     

Fatty acid metabolism in young oysters,Crassostrea gigas: Polyunsaturated fatty acids

Tetraselmis suecica andDunaliella tertiolecta were grown for 24 hr in the presence of¹⁴C sodium bicarbonate and then fed separately to batches of juvenile oysters,Crassostrea gigas, for 3 days.D. tertiolecta contained fatty acids no longer than C₁₈; 22∶6ω3 was absent inT. suecica. Analysis of the oyster fatty acids by radio gas chromatography (GC) showed that oysters were able to incorporate some of the dietary¹⁴C label into long-chain fatty acids not supplied in the diet, e.g., C₂₀ and C₂₂ mono- and polyunsaturated fatty acids, and particularly 20∶5ω3. However, the low¹⁴C incorporation into fatty acids longer or more unsaturated than those supplied in the diet suggests that elongation and desaturation activity in young oysters is not sufficient to sustain optimum growth.     

n-3 fatty acids: Antiatherosclerotic effects

The low incidence of cardiovascular disease associated epidemiologically with high consumption of food rich in n-3 fatty acids suggests the possibility that part of the beneficial cardiovascular effects of these natural substances may be due to a reduction of atherosclerosis. This has been recently confirmed in autoptic data and in at least one prospective trial evaluating the progression of coronary atherosclerosis in humans. This paper reviews published literature on n-3 fatty acids and atherosclerosis in animal models and in humans and in vitro experimental data yielding suport to the hypothesis of antiatherosclerotic effects of these substances.     

Biosynthesis of fatty acids from acetate in soybean suspension cultures

Suspension cultures of finely divided soybean cells established from callus were incubated with sodium [1(14)C] acetate for periods up to 86 hr. Lipids and fatty acids were analyzed for radioactivity in samples harvested at logarithmic time periods. Incorporation of acetate into cell lipid was directly proportional to the logarithm of time up to 32 hr, after an initial lag of 4-6 hr. Most of the lipid radioactivity was found in the phospholipid fraction, and all common soybean fatty acids became labeled within 6 hr. The order of labeling and distribution of radioactivity with time were essentially the same as in tissues from intact growing plants. These results support the concept of sequential desaturation of oleic acid in the cells. It was concluded that valid studies of the biosynthesis of common lipids in the soybean can be carried out for extended periods of time by use of undifferentiated cells in suspension cultures.     

Potential synthetic lubricants: Diol ester of C18-saturated cyclic acids

Monoalkyl esters of linseed-oil-derived C₁₈-saturated cyclic acids (HCal), described in earlier work, showed promise as lubricant base stocks for turbine aircraft as set forth in the military specification MIL-L-7808E. These esters, however, did not exhibit the increased oxidative stability and higher viscosity required by the more recent specification MIL-L-23699. Six diol esters of HCal have now been prepared. Both hindered and unhindered dihydric alcohols were used, including ethylene glycol, 1,4-cyclohexanedimethanol, 1,4-benzenedimethanol, 2,3-dimethyl-1,3-propanediol and 2,2,4,4-tetramethyl-1,3-cyclobutanediol (I). The viscosities of these esters at 210F ranged from 10.1 to 19.6 centistokes and the pour points, from −35 to −62F. Oxidative stabilities at 400F were determined with 0.5% each of phenyl-a-napthylamine (PANA) andp,p’-dioctyldiphenylamine as inhibitors. The esters of the unhindered diols had poor stability, whereas esters of the hindered diols, in particular I, exhibited excellent resistance to the formation of acidic decomposition products and sludge. Although the HCal ester of I by itself is too viscous to meet specification MIL-L-23699, its ASTM slope (0.650) is excellent. Blends of this material with less viscous hindered esters, commercially available, may find application as lubricants for high-performance turbine engines used in various aircraft. Presented at the AOCS Meeting in Los Angeles, 1966. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Uptake and metabolism of fatty acids by Soybean suspension cells

Soybean suspension cultures very rapidly take up C₁₆ and C₁₈ fatty acids by a nonspecific, nonenzymic binding of exogeneously added fatty acids to cell walls and by a subsequent transfer into the cell where they are rapidly incorporated into triacylglycerols, phosphatidylcholines, and phosphatidylethanolamines.¹⁴C-Palmitic and¹⁴C-stearic acids follow this sequence but are not desaturated, wherease¹⁴C-oleic and¹⁴C-linoleic acids are transferred more rapidly than the saturated fatty acids and are then further modified. All the data fit a sequence of events by which free oleic acid is first activated to a CoA thioester, and then desaturated to linoleyl-CoA; both thioesters are then transferred to triacylglycerols, phosphatidylcholine, and phosphatidylethanolamine.     

Effect of phospholipid n‐3 polyunsaturated fatty acids on rat lipid metabolism

It has been demonstrated that the amount and type of dietary fat are factors involved in the risk of arteriosclerosis and coronary or cerebral artery disease through lipid metabolism. In this study, we investigated the effects of phospholipids (PLs) containing n‐3PUFAs on lipid metabolism in rats. PLs containing n‐3PUFAs were prepared from squid (Todarodes pacificus) mantle muscle. Groups of male Wistar rats were fed AIN93G diet containing soybean oil (SO, 7%), fish oil (1.2%) + SO (5.8%), soybean PLs (1.8%) + SO (5.2%), or PLs containing n‐3PUFAs (1.8%) + SO (5.2%). The following indicators were assayed as indexes of lipid metabolism: TAG and cholesterol in serum and liver, fecal cholesterol, bile‐acid excretion, and liver mRNA expression levels of genes encoding proteins involved in cholesterol homeostasis. Serum and liver TAG contents decreased significantly in the group fed PLs containing n‐3PUFAs as compared to other groups, accompanied by a significant decline in the expression level of sterol regulatory element binding protein‐1c. The decrease in cholesterol content in the group fed PLs containing n‐3PUFAs was due to the increase in fecal cholesterol excretion and the increase of mRNA expression levels of ATP‐binding cassette (ABC) G5 and ABCG8 in liver. Practical applications : PLs containing n‐3PUFAs decreased serum and liver TAG contents compared with that induced by soybean PLs. Further, PLs containing n‐3PUFAs can induce a reduction in serum and liver cholesterol concentrations as well as the triglyceride‐reducing effect of conventional n‐3PUFAs containing TAG. In other words, dietary n‐3PUFAs contained in PLs can prevent life‐style diseases such as hyperlipidemia, arteriosclerosis and coronary, or cerebral artery disease more effectively than TAG containing n‐3PUFAs. Therefore, it is expected that the risk of lifestyle diseases would be decreased if PL containing n‐3PUFAs can be supplied routinely. In this study, PLs containing n‐3PUFAs were prepared from squid mantle muscle. On an industrial scale, such PLs can be produced from various unused resources and waste materials of fisheries. We conclude that highly functional foods could be developed based on the findings of this study, and would be available for health promotion worldwide.     

An interaction of DDT in the metabolism of essential fatty acids

The growth of female rats was depressed further by the incorporation of DDT into a ration deficient in essential fatty acids (EFA). With female rats fed a ration supplemented with EFA, DDT produced a slight stimulation in growth. DDT also produced an increase in the 20∶3ω9/20∶4ω6 ratio in liver lipids of male rats fed a ration deficient in EFA. These data indicate an effect in EFA nutrition. Substantial changes in the fatty acid composition of liver lipids resulted from the feeding of DDT. The proportion of 16∶0 was decreased, while that of 18∶0 was increased. With rats on the supplemented rations an increase in the proportion of 20∶4ω6 was observed, while in the deficient rats a comparable increase was observed in the proportion of 20∶3ω9. These changes in fatty acid composition have been related to the proliferation of hepatic smooth endoplasmic reticulum induced by the DDT, and it is suggested that this effect could increase the demand for EFA by the liver, thus influencing EFA nutrition. Technical Paper No. 3156, Oregon Agricultural Experiment Station.     

Role of oleic acid in the metabolism of essential fatty acids

Groups of young male guinea pigs were fed diets containing corn oil, coconut oil, coconut oil plus elaidic acid, and coconut oil plus oleic acid. The oleic acid-fed group showed signs of essential fatty acid deficiency after four weeks and severe signs after eight weeks. The elaidic acid-fed group did not show these symptoms. It is proposed that oleic acid competes competitively with linoleic acid as a substrate for the enzymes involved in linoleate transformations when only a very limited supply of linoleic acid is available to the animals and oleic acid is made available in relatively large amounts. A detailed analysis of the serum, liver, and adipose tissue lipid and a study of the incorporation of acetate-1-C¹⁴ into different lipids is presented. This paper is based on work supported in part by United States Public Health Grant No. HTS 5306 and by a grant from the Nutrition Foundation Inc., New York.     

Fat metabolism in higher plants: Metabolism of medium chain fatty acids

Cell free preparations of avocado mesocarp and spinach leaf tissue rapidly convert lauryl CoA to DL-3-hydroxyl lauric acid as well as 2-, and 3-dodecanoic acids. The conversion does not occur under anaerobic conditions unless a suitable redox carrier such as ferredoxin is present. H2 18O is incorporated into the 3-hydroxyl function, but O2(18) is not. The characteristics of this system are presented and a possible function of this system is proposed.     

Epoxidized esters of fatty acids as internal and external plasticizers for polyvinyl acetate

Summary Fatty acid esters modified with epoxy or acetoxy groups were found to be compatible with polyvinyl acetate. These esters are good plasticizers for polyvinyl acetate compositions and may be used for plasticizing polyvinyl acetate in latex form. The use of a good swelling agent, such as toluene, was found desirable for permitting plasticization of these emulsions. The epoxidized oils may also assist in reducing container corrosion and in stabilizing the emulsions by reacting with the acetic acid formed by the hydrolysis of residual vinyl acetate. Emulsions of copolymers of vinyl acetate and vinyl epoxystearate were prepared, yielding clear, hard films which were internally plasticized. The epoxy group in these interpolymers is a potential source for cross-linking vinyl acetate polymer films. The epoxy group of the co-polymers (internal-phase stabilization) and the epoxidized oils (external-phase stabilization) were found to be virtually equivalent for removal of acetic acid from polyvinyl acetate emulsions. Presented at the Fall Meeting, American Oil Chemists' Society, Philadelphia, Pa., October 11, 1955. A laboratory of the Eastern Utilization Research Branch, Agricultural Research Service, U. S. Department of Agriculture.     

New branched-chain fatty acids from the senegalese gorgonianLeptogorgia piccola (white and yellow morphs)

Fatty acids from total lipids of the gorgonianLeptogorgia piccola (white and yellow morphs), collected from the same area at two different periods with regard to the average water temperature, were studied. More than fifty fatty acids were identified as methyl esters andN-acyl pyrrolidides by gas chromatography and gas chromatography/mass spectrometry. Three new, branched-chain unsaturated fatty acids were identified in addition to the unusual 7-methyl-6-hexadecenoic acid, namely 10-methyl-6-hexadecenoic, 7,9-dimethyl-6-hexadecenoic, and 10-methyl-6,9-heptadecadienoic acids. Also 6,9-heptadecadienoic acid was identified. The fatty acid patterns of specimens harvested in colder waters were quite different from those harvested in warmer waters in that the former contained high amounts of methylene-interrupted polyunsaturated acids, including tetracosapolyenoic acids, especially 6,9,12,15,18–24∶5 (up to 15.8% of the total acid mixture) and 6,9,12,15,18,21–24∶6 (up to 5.3%). Arachidonic acid was, nevertheless, a major component in all the fatty acid mixtures studied (13.6–20.5%). Based on gas chromatography/Fourier transform infrared experiments, the double bonds were assigned the (Z) configuration. Several fatty aldehydes and their dimethyl acetals were also detected, of which the most abundant was octadecanal.     

Marine n-3 fatty acids: Basic features and background

There is some evidence from epidemiology that intake of n-3 polyunsaturated fatty acids (PUFA) from seafood may protect against coronary artery disease (CAD). This hypothesis is further supported from animal data showing a beneficial effect of n-3 PUFA on thrombosis and atherosclerosis in animals fed fish oils in most, but not all, studies. There are several mechanisms by which an increased intake of marine n-3 PUFA may protect against CAD; the most universal finding is a reduction of plasma triglycerides. It is puzzling, however, that a very low amount of n-3 PUFA, with no known beneficial biochemical effects, seems to be cardioprotective. It has therefore been of paramount interest to perform clinical trials. Such evidence and trials are discussed in later chapters, and the results have been very encouraging.