Component fatty acids ofAspergillus terreus fat

The component fatty acids of the fat elaborated byAspergillus terreus Thom, which was found to be a promising mold for the production of fat, have been studied. The fat has, based on gas liquid chromatographic evidence, 0.1% lauric, 1.9% myristic, 23.4% palmitic, 0.1% palmitoleic, 0.3% stearic, 14.1% oleic, 39.4% linoleic and 20.7% linolenic acids. The presence of large proportions of linoleic and linolenic acids suggests technological interest for the fat.     

Dietary trans α‐linolenic acid does not inhibit Δ5‐ and Δ6‐desaturation of linoleic acid in man

Dietary trans monoenes have been associated with an increased risk of heart disease in some studies and this has caused much concern. Trans polyenes are also present in the diet, for example, trans α‐linolenic acid is formed during the deodorisation of α‐linolenic acid‐rich oils such as rapeseed oil. One would expect the intake of trans α‐linolenic acid to be on the increase since the consumption of rapeseed oil in the western diet is increasing. There are no data on trans α‐linolenic acid consumption and its effects. We therefore carried out a comprehensive study to examine whether trans isomers of this polyunsaturated fatty acid increased the risk of coronary heart disease. Since inhibition of Δ6‐desaturase had also been linked to heart disease, the effect of trans α‐linolenic acid on the conversion of [U‐¹³C]‐labelled linoleic acid to dihomo‐γ‐linolenic and arachidonic acid was studied in 7 healthy men recruited from the staff and students of the University of Edinburgh. Thirty percent of the habitual fat was replaced using a trans ‘free’‐ or ‘high’ trans α‐linolenic acid fat. After at least 6 weeks on the experimental diets, the men received 3‐oleyl, 1,2‐[U‐¹³C]‐linoleyl glycerol (15 mg twice daily for ten days). The fatty acid composition of plasma phospholipids and the incorporation of ¹³C‐label into n‐6 fatty acids were determined at day 8, 9 and 10 and after a 6‐week washout period by gas chromatography‐combustion‐isotope ratio mass spectrometry. Trans α‐linolenic acid of plasma phospholipids increased from 0.04 ? 0.01 to 0.17 ? 0.02 and cis ? ‐linolenic acid decreased from 0.42 ? 0.07 to 0.29 ? 0.08 g/100 g of fatty acids on the high trans diet. The composition of the other plasma phospholipid fatty acids did not change. The enrichment of phosphatidyl ¹³C‐linoleic acid reached a plateau at day 10 and the average of the last 3 days did not differ between the low and high trans period. Both dihomo‐γ‐linolenic and arachidonic acid in phospholipids were enriched in ¹³C, both in absolute and relative terms (with respect to ¹³C‐linoleic acid). The enrichment was slightly and significantly higher during the high trans period (P<0.05). Our data suggest that a diet rich in trans α‐linolenic acid (0.6% of energy) does not inhibit the conversion of linoleic acid to dihomo‐γ‐linolenic and arachidonic acid in healthy middle‐aged men consuming a diet rich in linoleic acid.     

Geometrical isomerization of polyunsaturated fatty acids in physically refined rapeseed oil during plant‐scale deodorization

The effect of the operating temperature (between 220 and 270 °C) on the formation of trans isomers of linoleic and linolenic acids in physically refined rapeseed oil during deodorization in a plant‐scale semicontinuous tray‐type deodorizer (capacity 10 t/h) was investigated. The industrial procedures of physical refining consisted of a two‐step bleaching and deodorization process. The degree of isomerization of linoleic acid ranged from 0.33 to 4.77% and that of linolenic acid from 4.43 to 45.22% between 220 and 270 °C, respectively. A relation between the logarithm of the degree of isomerization and the deodorization temperature can be approximated by statistically highly significant linear functions for both linoleic and linolenic acids. Oleic acid was resistant to the heat‐induced geometrical isomerization. The values found for the ratio between the degrees of isomerization of linolenic and linoleic acids, slightly decreasing with increasing temperature, were equal to 13.6 and 12.9 at 230 and 240 °C, respectively. Two trans isomers of linoleic acid, exclusively with one double bond isomerized into trans configuration, and four trans isomers of linolenic acid, mostly with one double bond isomerized into trans configuration, were determined in deodorized rapeseed oils. Linolenic acid was observed to be the main source responsible for the formation of nearly all trans fatty acids in physically refined rapeseed oil. At 235 °C, a deodorization temperature considered as a reasonable technological compromise, the content of trans fatty acids in plant‐scale physically refined rapeseed oil was less than 1% of total fatty acids, which would be acceptable for further application.     

Ernährungsphysiologische Wirkung unterschiedlicher Gemische von Öl-, Linol- und Linolensäure bei wachsenden Schweinen. 1. Einfluß auf Wachstum,Futterverwertung und Schlachtkörper-Zusammensetzung der Tiere

Physiological Effect of Various Mixtures of Oleic, Linoleic and Linolenic Acids on Growing Pigs: 1. Influence on Growth, Feed Conversion and Carcass Composition of the Animals The influence of increasing concentrations of oleic acid (25-43%), linoleic acid (19-34%) and linolenic acid (2-31%) on growth, feed conversion, carcass quality and the development of some internal organs has been investigated by a feeding trial over a range of 19 to 100 kg live weight with 72 pigs (male castrates, German Land Race) divided into 12 groups. Increasing amounts of oleic acid resulted in increasing daily gain and improved feed conversion. In the linoleic and linolenic acid series however performance (daily gain and feed conversion) was improved only up to 24% or 20% respectively, followed by a drastic decrease of performance at higher concentrations of these fatty acids. Investigation of carcass quality showed alterations in total fat content (decrease of back fat as well as lean to fat ration in the section at the 14^th thoratic vertebra) in the groups of the highest concentration of linolenic and linoleic acids. Effects on the development of the internal organs (enlargement of heart, liver, kidneys, thyroid glands and adrenal glands) were especially found in the groups with highest concentration of linolenic acid. In nearly all groups with a linolenic acid amount of 20% and more several cases - partly very serious ones - of yellow fat disease occurred.     

Varietal difference in lipid content and fatty acid composition of highbush blueberries

Lipids from five cultivars of highbush blueberries (Vaccinium corymbosum L.) were extracted and fractionated into neutral lipids (60–66%), glycolipids (20–22%) and phospholipids (14–18%). The major fatty acids in all fractions were palmitic (16∶0), oleic (18∶1), linoleic (18∶2), and linolenic (18∶3) acids. All lipid classes had a large concentration of C₁₈ polyunsaturated acids (84–92%), indicating that blueberries are a rich source of linoleic and linolenic acids. Changes in the fatty acid composition of neutral lipids and phospholipids were not significantly different among the five cultivars, but significant differences were noted in the ratios of linoleic and linolenic acids in the glycolipids fraction.     

Fat content and fatty acid composition of oils extracted from selected wild-gathered tropical plant seeds from Nigeria

As the search for alternative sources of food to alleviate hunger continues, this study was undertaken to determine the fat content and the fatty acid composition of 15 lesser-known wild tropical seeds gathered in Nigeria. Results were contrasted with five tropical soybean varieties (Glycine max). The fat content varies from less than 1% (Pterocarpus santalinoides, Daniellia ogea) to 59% (Entandrophragma angolense). The fatty acid composition of most of the wild and mostly leguminous seeds differed considerably, compared to the composition of tropical soybeans. The oil of Adansonia digitata, Prosopis africana, Afzelia lebbeck, Enterolobium cyclocarpium, and Sesbania pachycarpa contained high proportions of linoleic and oleic acid as well as palmitic and linolenic acid. Seeds of Milletia thonningii, Lonchocarpus sericeus, and S. pachycarpa were much higher in linolenic acid and relatively poor in linoleic acid, compared to soybeans. The content of saturated fatty acids was higher than that of soybeans, resulting in lower polyunsaturated/saturated (P/S) ratios (0.83–2.12) than observed in soybeans (P/S=3.4), with the exception of the composition of S. pachycarpa (P/S=3.15). Some of these less familiar wild seeds could be used as sources for industrial or edible oils, provided that possible toxic constituents could be removed.     

Chemical and nutritional studies on hanshi (perilla frutescens), a traditional oilseed from northeast india

Perilla frutescens, an edible oilseed of Northeast India, was evaluated for its nutrient composition and protein quality. It was found to be a rich source of protein (17.0%) and fat (51.7%). The fatty acid profile indicated that perilla oil is rich in polyunsaturated fatty acids, such as linolenic (56.8%) and linoleic (17.6%). The amino acid composition showed that valine was the limiting amino acid of perilla protein. The protein efficiency ratio of the seed protein (2.07) was lower than that of casein (2.99), but comparable to common oilseeds. True digestibility of the seed protein (82.6%) was also lower than that of casein (89.3%).     

Isomerization of linoleic,linolenic, and other polyunsaturated acids with potassium tertiary butoxide and its application in the spectrophotometric estimation of these acids

Summary It has been shown that potassium tertiary butoxide isomerizes such unsaturated fatty acids as linoleic, linolenic, arachidonic, and pentaenoic at a temperature of 90°. With 5% potassium-t-butanol reagent conjugation of linoleic acid attains a maximum at the end of 2 hrs. and remains steady thereafter even up to 10 hrs. while with linolenic, arachidonic, and pentaenoic acids it is still occurring at the end of such long times of reaction as 48 and 10 hrs., respectively. This continuance of reaction at the end of such long periods with these higher unsaturated acids demonstrates that the isomerization with the tertiary butoxide reagent at 90° is not complicated by side reactions, such as polymerization and deisomerization. All the methods studied give high absorption coefficients in the lower regions of maxima—233 mμ with linolenic, 233 mμ and 268 mμ with arachidonic acids—showing thereby that isomerizations of these acids occur stepwise. Based on this study, a method using 5% potassium-t-butanol as reagent, at 90° with a time of reaction of 4 hrs., has been proposed for the estimation of linoleic and linolenic acids. The k₂₃₃ value for linoleic acid (94.0) obtained by this method compares very well with those by the 6.6% KOH-glycol and 21% KOH-glycol methods while with linolenic acid the k₂₃₃ value (63.2) is higher and k₂₆₈ value (74.2) lies intermediate between those by the other methods. The proposed method is shown to estimate the linoleic and linolenic acid contents of several typical oils with about the same degree of accuracy as either the 6.6% KOH-glycol or 21% KOH-glycol methods. Appendix. When this paper was ready to be submitted, a note (27) describing the use of tertiary butoxide reagent on the kinetic study of isomerization of linoleic and linolenic acids came to our attention. Extinction coefficients at 235 mμ and 268 mμ are reported for linolenic acid and the values (61.4, 74.2) obtained by isomerization with a molar solution of the reagent at 99.5° and 180 minutes’ time of reaction are about the same order as those reported in this paper. It is of interest to note that these authors have also noted that no destruction of the product occurs at this temperature and time of heating. Post-doctoral Fellow in Physiological Chemistry. This work was supported in part from funds granted by the Ohio State University Research Foundation to the University for aid in fundamental research.     

Lipids and human milk

To support the growth and development of the breast‐fed infant, human milk provides the dietary essential fatty acids, linoleic acid (LA; 18:2n‐6), α‐linolenic acid (ALA, 18:3n‐3), as well as longer‐chain polyunsaturated fatty acids including arachidonic acid (20:4n‐6) and docosahexanoic (DHA 22:6n‐3). The linoleic acid, alpha‐linolenic acid, DHA and arachidonic acid concentration of pasteurized and unpasteurized human milk remains stable during the first month of storage at –20°C and –80°C. However after the first month, a slow decrease in concentration progresses until the end of 6 months of storage at both temperatures. The levels of n‐6 and n‐3 fatty acids, particularly linoleic acid, alpha‐linolenic acid and DHA, in human milk vary widely within and among different populations, and are readily changed by maternal dietary intake of the respective fatty acid. The present paper reviews recent understanding from key researchers of maternal diet and human milk fat composition and form our work the effect of milk fat composition on storage conditions. It is important to understand that maternal diet can affect human milk fat composition and subsequently infant development and growth.     

Determination of the fatty acid profile by 1H‐NMR spectroscopy

The common unsaturated fatty acids present in many vegetable oils (oleic, linoleic and linolenic acids) can be quantitated by ¹H‐nuclear magnetic resonance spectroscopy (¹H‐NMR). A key feature is that the signals of the terminal methyl group of linolenic acid are shifted downfield from the corresponding signals in the other fatty acids, permitting their separate integration and quantitation of linolenic acid. Then, using the integration values of the signals of the allylic and bis‐allylic protons, oleic and linoleic acids can be quantitated. The procedure was verified for mixtures of triacylglycerols (vegetable oils) and methyl esters of oleic, linoleic and linolenic acids as well as palmitic and stearic acids. Generally, the NMR (400 MHz) results were in good agreement with gas chromatographic (GC) analyses. As the present ¹H‐NMR‐based procedure can be applied to neat vegetable oils, the preparation of derivatives for GC would be unnecessary. The present method is extended to quantitating saturated (palmitic and stearic) acids, although in this case the results deviate more strongly from actual values and GC analyses. Alternatives to the iodine value (allylic position equivalents and bis‐allylic position equivalents) can be derived directly from the integration values of the allylic and bis‐allylic protons.     

Chemical investigation of the seeds of brassica oleracea var. acephala

Fatty acid composition of the seed fat ofBrassica oleracea Var.acephala (Cruciferae) has been determined. Erucic acid has been found to be the major component followed by linoleic, oleic, linolenic, arachidic and palmitic acids. Traces of stearic and eico-senoic acids have also been detected. The unsaponifiable matter contained β-sitosterol, and defatted seeds showed the presence of sucrose.     

trans-Polyunsaturated fatty acids in French edible rapeseed and soybean oils

The fatty acid compositions of rapeseed and soybean oils marketed in France have been determined by gas liquid chromatography on a fused-silica capillary column coated with a 100% cyanopropyl polysiloxane stationary phase. Under the operating conditions employed, methyl esters of linolenic acid geometrical isomers could be separated and quantitated easily without any other complementary technique. With only one exception, all samples under study (eight salad oils and five food samples) contain geometrical isomers of linolenic acid in measurable, although variable, amounts. Totaltrans-18:3 acids may account for up to 3% of total fatty acids. This value corresponds to a degree of isomerization (percentage oftrans isomers relative to total octadecatrienoic acids) of 30%. Examination of our data indicates that the distribution pattern of linolenic acid geometrical isomers does not depend on the degree of isomerization. The two main isomers always have thec,c,t and thet,c,c configurations. These isomers occur in the almost invariable relative proportions of 47.8±1.7% and 41.1±1.0%, respectively. The third mono-trans isomer is present in lower amounts−6.5±0.7%. The only di-trans isomer that can be quantitated with sufficient accuracy is thet,c,t isomer (4.9±1.5%). Mono-trans isomers of linoleic acid are also present in these oils. However, their maximum percentages are lower than those determined for linolenic acid geometrical isomers. In the oils showing the highest degrees of isomerization,trans isomers of linoleic acid account for 0.5% (rapeseed oils) and 1% (soybean oils) of total fatty acids. Taking into account all data, it would appear that the probability of isomerization of linolenic acid is about 13–14 times that of linoleic acid.     

Deodorization of vegetable oils: Prediction of trans polyunsaturated fatty acid content

Kinetics of the formation of trans linoleic acid and trans linolenic acid were compared. Pilot plant-scale tests on canola oils were carried out to validate the laboratory-scale kinetic model of geometrical isomerization of polyunsaturated fatty acids described in our earlier publication. The reliability of the model was confirmed by statistical calculations. Formation of the individual trans linoleic and linolenic acids was studied, as well as the effect of the degree of isomerization on the distribution of the trans fatty acid isomers. Oil samples were deodorized at temperatures from 204 to 230°C from 2 to 86 h. Results showed an increase in the relative percentage of isomerized linolenic and linoleic acid with an increase in either the deodorization time or the temperature. The percentage of trans linoleic acid (compared to the total) after deodorization ranged from <1 to nearly 6%, whereas the percentage of trans linolenic acid ranged from <1 to >65%. Applying this model, the researchers determined the conditions required to produce a specially isomerized oil for a nutritional study. The practical applications of these trials are as follows: (i) the trans fatty acid level of refined oils can be predicted for given deodorization conditions, (ii) the conditions to meet increasingly strict consumer demands concerning the trans isomer content can be calculated, and (iii) the deodorizer design can be characterized by the deviation from the theoretical trans fatty acid content of the deodorized oil.     

Ernährungsphysiologische Wirkung unterschiedlicher Gemische von Öl-, Linol- und Linolensäure bei wachsenden Schweinen. 2. Einfluß auf Depotfette und Blutlipide

Physiological Effect of Various Mixtures of Oleic, Linoleic and Linolenic Acids on Growing Pigs: 2. Influence on Depot Fats and Blood Lipids At the end of the feeding trials described extensively in the first contribution, from all animals saddle bacon and leaf fat as well as serum lipids have been investigated on effects of the various food fats. Earlier results have been confirmed according to which the increased supply of unsaturated fatty acids results in an increase of the content in depot fat and in a decrease of palmitic and stearic acid. The storage of linoleic and linolenic acids is linked to the consumed amount of these acids in a linear way. Some hints have been found for the occurrence of yellow fat desease that besides the deficiency of vitamin E an enzyme activating effect of higher amounts of linolenic acid may be responsible. Furthermore the attacked animals showed a linear dependence of the fat content in the yellow tissue from its peroxide value. As well linolenic acid as oleic acid led to a significant decrease of the serum triglycerides. Besides, linolenic acid lowered the content of serum cholesterol, whereas linoleic acid caused a significant increase of the HDL content.     

Effects of Supercritical Fluid Extraction Parameters on Unsaturated Fatty Acid Yields of Pistacia terebinthus Berries

Utilization of renewable resources and development of new processes aimed at converting these materials into value added bio-products are gaining more emphasis. The scope of this study was to optimize supercritical CO₂ extraction (SFE) parameters such as pressure, temperature and flow rate for the yields of unsaturated fatty acids from Pistacia terebinthus berries by a Box-Behnken statistical design. All samples were analyzed for fatty acids by GC-FID. The most effective variables were pressure (P < 0.005) and flow rate (P ≤ 0.005). Maximizing the evaluative criteria for dependent variables (oleic acid, linoleic acid and linolenic acid), optimal conditions were determined to be 240 bar, 60 °C and a flow rate of 16 g/min yielding 51.2% oleic acid, 26.5% linoleic acid and 1.0% linolenic acid. The amounts of unsaturated fatty acids in SFE samples (81.3%) were higher than the hexane (74.3%) and were similar to that of cold press samples (80.1%). High concentrations of unsaturated fatty acids can indicate the utilization of the berries as a major dietary source and demonstrate challenges for industrial application of SFE as a green technology.     

Pithecolobium dulce II: Lipoids from the Seed

The component fatty acids of P. dulce seed fat has been found to be palmitic 7.2%, stearic 7.1%, arachidic 1.4%, behenic 6.9%, lignoceric 6.2%, oleic 47.3%, linoleic 21.7% and linolenic 1.7%. The phosphatide fatty acids also showed the presence of behenic and lignoceric acids.     

Triacylglycerols from viper bugloss (Echium vulgare L.) seed bio‐oil

Triacylglycerols (TAG) in viper bugloss oil were isolated from raw pressed oil by silicic acid column chromatography. The obtained blend of TAG was separated by silver ion thin‐layer chromatography (TLC Ag⁺) into nine fractions, varying in terms of unsaturation level and molecular polarity. The composition of TAG in viper bugloss oil was determined by HPLC coupled with a diode‐array detector and an evaporative light‐scattering detector. The results showed that the first three fractions were combinations of TAG containing palmitic, oleic and linoleic acids. Fractions 4 and 6 contained TAG of a similar acid composition as above, but with the addition of γ‐linolenic acid. The remaining fractions (7–9) were the most varied in acid composition. They were found to contain 26–39% palmitic acid, 12–15% oleic acid, 13–41% linoleic acid 8–24% γ‐linolenic acid, 1.5–5.5% α‐linolenic acid and 1–5% stearidonic acid. The analysis of fatty acid allocation in TAG of viper bugloss lipids revealed that linoleic acid (ranging from 2 to 100%) was the only acid found in all isolated fractions. In the investigated oil, the predominant TAG included: LnLnG (11.38%), LnLnSt (11.17%), LnGSt (7.71%), LnStSt (6.19%) and LnLnLn (5.44%). Almost 86% of the TAG contained α‐linolenic acid, while γ‐linolenic and stearidonic acids amounted to 49 and 38%, respectively.     

Cis-trans isomerization of oleic,linoleic and linolenic acids

The equilibrium composition ofcis andtrans isomers obtained by isomerizing oleic, linoleic, and linolenic acids with selenium or nitrous acid has been studied using gas chromatography and infrared spectroscopy. The oleic/elaidic equilibrium mixture was found to contain 75–80% elaidic acid instead of the generally accepted 66% value. It is felt that the greater accuracy of gas chromatography and infrared analyses over older methods allows this equilibrium to be defined with greater precision. Similar studies on thecis-trans isomerization of linoleic and linolenic acids indicated that their equilibrium mixtures also contained 75–80%trans double bonds. With linoleic acid, thesetrans bonds were shown to be randomly distributed among the double bonds present. Cis-trans isomerization of linoleic or linolenic acids with selenium produced by-products having elution times equivalent to 18∶2, 18∶1, and 18∶0 on a gas chromatograph. No such by-products were observed when oleic acid was isomerized. Apparently some type of hydrogen-transfer reaction accompanies thecis-trans isomerization of polyunsaturated acids with selenium. Presented at the AOCS meeting in Toronto, Canada, 1962.     

Borage and evening primrose oil

The paper gives a short overview about the production and composition of borage (Borago officinalis) and evening primrose (Oenothera biennis) oil considering special aspects of the production as cold‐pressed oil. Both oils are characterized by a remarkable amount of γ‐linolenic acid, which has some nutritional advantages. The fatty acid composition of evening primrose oil is dominated by linoleic acid with about 72% and about 13% γ‐linolenic acid, while borage oil consists of twice the amount of γ‐linolenic acid and only 38% linoleic acid. The amount of saturated fatty acids is higher in borage oil. The tocopherol composition of both oils is dominated by γ‐tocopherol, with borage oil containing twice the amount compared to evening primrose oil.     

Modifying milk fat composition of dairy cows to enhance fatty acids beneficial to human health

There is increased consumer awareness that foods contain microcomponents that may have beneficial effects on health maintenance and disease prevention. In milk fat these functional food components include EPA, DHA, and CLA. The opportunity to enhance the content of these FA in milk has improved as a result of recent advances that have better defined the interrelationships between rumen fermentation, lipid metabolism, and milk fat synthesis. Dietary lipids undergo extensive hydrolysis and biohydrogenation in the rumen. Milk fat is predominantly TG, and de novo FA synthesis and the uptake of circulating FA contribute nearly equal amounts (molar basis) to the FA in milk fat. Transfer of dietary EPA and DHA to milk fat is very low (<4%); this is, to a large extent, related to their extensive biohydrogenation in the rumen, and also partly due to the fact that they are not transported in the plasma lipid fractions that serve as major mammary sources of FA uptake (TG and nonesterified FA). Milk contains over 20 isomers of CLA but the predominant one is cis-9,trans-11 (75–90% of total CLA). Biomedical studies with animal models have shown that this isomer has anticarcinogenic and anti-atherogenic activities. cis-9,trans-11-CLA is produced as an intermediate in the rumen biohydrogenation of linoleic acid but not of linolenic acid. However, it is only a transient intermediate, and the major source of milk fat CLA is from endogenous synthesis. Vaccenic acid, produced as a rumen biohydrogenation intermediate from both linoleic acid and linolenic acid, is the substrate, and Δ9-desaturase in the mammary gland and other tissues catalyzes the reaction. Diet can markedly affect milk fat CLA content, and there are also substantial differences among individual cows. Thus, strategies to enhance milk fat CLA involve increasing rumen outflow of vaccenic acid and increasing Δ9-desaturase activity, and through these, several-fold increases in the content of CLA in milk fat can be routinely achieved. Overall, concentrations of CLA, and to a lesser extent EPA and DHA, can be significantly enhanced through the use of diet formulation and nutritional management of dairy cows.