Enzymatic hydrolysis of oat and soya lecithin: Effects on functional properties

Enzymatic hydrolysis of oat and soy lecithins and its effects on the functional properties of lecithins were investigated. The phospholipase used was most efficient at low enzyme and substrate concentrations. More fatty acids were released from soy lecithin than from oat lecithin. The maximum degree of hydrolysis was 760 μmol free fatty acids per gram soy lecithin and 170 μmol free fatty acids per gram oat lecithin. On the basis of the total carbohydrate and phosphorus contents in the polar fractions of the lecithins, oat lecithin contained more glycolipids and less phospholipids than soy lecithin. With regard to functional properties, the stability of oil-in-water emulsions was enhanced by hydrolyzed soy lecithin and by crude and hydrolyzed oat lecithins, but only hydrolyzed soy lecithin prevented the recrystallization of barley starch. The dissociation enthalpy of amylose-lipid-complex (AML-complex) was significantly higher when hydrolyzed soy lecithin was present. Hydrolyzed oat lecithin slightly affected the dissociation enthalpy of AML-complex. The other lecithins had no effect on recrystallization or dissociation enthalpies in the barley-starch matrix.     

Growth potential for soybean oil products as industrial materials

Crude soybean oil, as a major source of edible oil for the world, is available on such a scale that it serves additionally as the origin for many industrial applications and for such materials as phospholipids (lecithins, cephalins), tocopherols (for vitamin E), sterols (for pharmaceuticals) and recovered fatty acids from acidulated soapstocks. The latter always have offered the oleochemicals manufacturer a low cost source of valuable fatty acids, and soybean oil itself, after hydrogenation, serves as the most readily available, lowest cost source of 90% stearic acid from among all fats and oils. As an alternative to alkali refining and the soapstock produced, physical refining of the degummed soybean oil is a potential source for fatty acids and for recovery of larger amounts of valuable sterols and tocopherols, but this process severely degrades the oxidation stability of the fatty acids. The largest potentials for growth in industrial applications are for soybean oil itself in pesticide dispersion and grain dust control; triglycerides and fatty acids split therefrom for 90% stearate oleochemicals and selected food additivies; fatty acids from soapstocks up-graded medium-grade oleochemicals, medium-grade soaps for industrial cleaning operations, and in animal feeds and pet foods; phospholipid gums in fractionated and modified lecithins and cephalins; soy deodorizer distillates containing α-to copherol (vitamin E) and sterol-derived sex hormones. Inclusion of food additives, feed and pet food additives with the more usual industrial markets results in the conclusion that industrial utilization of soybean oil could reach 12% of total consumption in the U.S. within five years.     

Effect of degumming reagents on the recovery and nature of lecithins from crude canola,soybean and sunflower oils

Six reagents (water, citric acid, phosphoric acid, oxalic acid, acetic anhydride and maleic anhydride) were evaluated for their effectiveness in degumming three crude vegetable oils (canola, soybean and sunflower). All chemical reagents tested were found to be significantly more effective than water in removing lecithin material from all three oils except for acetic anhydride degumming of canola. Citric and phosphoric acids were found to be very effective in reducing phosphorus levels in canola oil (91 and 93% removal, respectively). For soybean oil, all reagents except water showed excellent degumming ability by removing 98% phosphorus, while in the case of sunflower oil, maleic anhydride and oxalic acid produced the highest level of phosphorus removal (95 and 90%, respectively). Both citric acid and acetic anhydride were effective in removing Fe from all three oils during degumming (84 to 94%), while phosphoric acid showed slightly lower values (73 to 87%). No significant changes in the phospholipid composition or fatty acid profiles of the phospholipid classes were observed as a result of degumming with the various chemical reagents. In general, canola phospholipids were lowest in palmitic, stearic and linoleic acid and contained the highest levels of oleic acid when compared to soybean and sunflower phospholipids. Both citric and acetic anhydride were found to influence the removal of an unknown glycolipid significantly. Canola lecithin was shown to contain a greater amount of glycolipids than sunflower and soybean lecithins.     

Frying stability of soybean and canola oils with modified fatty acid compositions

Pilot plant-processed samples of soybean and canola (lowerucic acid rapeseed) oil with fatty acid compositions modified by mutation breeding and/or hydrogenation were evaluated for frying stability. Linolenic acid contents were 6.2% for standard soybean oil, 3.7% for low-linolenic soybean oil and 0.4% for the hydrogenated low-linolenic soybean oil. The linolenic acid contents were 10.1% for standard canola oil, 1.7% for canola modified by breeding and 0.8% and 0.6% for oils modified by breeding and hydrogenation. All modified oils had significantly (P<0.05) less room odor intensity after initial heating tests at 190°C than the standard oils, as judged by a sensory panel. Panelists also judged standard oils to have significantly higher intensities for fishy, burnt, rubbery, smoky and acrid odors than the modified oils. Free fatty acids, polar compounds and foam heights during frying were significantly (P<0.05) less in the low-linolenic soy and canola oils than the corresponding unmodified oils after 5 h of frying. The flavor quality of french-fried potatoes was significantly (P<0.05) better for potatoes fried in modified oils than those fried in standard oils. The potatoes fried in standard canola oil were described by the sensory panel as fishy.     

trans fatty acids. 4. Effects on fatty acid composition of colostrum and milk

trans Isometric fatty acids of partially hydrogenated fish oil (PHFO) consist oftrans 20∶1 andtrans 22∶1 in addition to thetrans isomers of 18∶1, which are abundant in hydrogenated vegetable oils, such as in partially hydrogenated soybean oil (PHSBO). The effects of dietarytrans fatty acids in PHFO and PHSBO on the fatty acid composition of milk were studied at 0 (colostrum) and 21 dayspostpartum in sows. The dietary fats were PHFO (28%trans), or PHSBO (36%trans) and lard. Sunflower seed oil (4%) was added to each diet. The fats were fed from three weeks of age throughout the lactation period of Experiment 1. In Experiment 2 PHFO or “fully” hydrogenated fish oil (HFO) (19%trans), in comparison with coconut oil (CF) (0%trans), was fed with two levels of dietary linoleic acid, 1 and 2.7% from conception throughout the lactation period. Feedingtrans-containing fats led to secretion oftrans fatty acids in the milk lipids. Levels oftrans 18∶1 andtrans 20∶1 in milk lipids, as percentages of totalcis+trans 18∶1 andcis+trans 20∶1, respectively, were about 60% of that of the dietary fats, with no significant differences between PHFO and PHSBO. The levels were similar for colostrum and milk. Feeding HFO gave relatively lesstrans 18∶1 andtrans 20∶1 fatty acids in milk lipids than did PHFO and PHSBO. Only low levels ofcis+trans 22∶1 were found in milk lipids. Feedingtrans-containing fat had no consistent effects on the level of polyenoic fatty acids but reduced the level of saturated fatty acids and increased the level ofcis+trans monoenoic fatty acids. Increasing the dietary level of linoleic acid had no effect on the secretion oftrans fatty acids but increased the level of linoleic acid in milk. The overall conclusion was that the effect of dietary fats containingtrans fatty acids on the fat content and the fatty acid composition of colostrum and milk in sows were moderate to minor.     

Low erucic acid canola oil does not induce heart triglyceride accumulation in neonatal pigs fed formula

Canola oil is not approved for use in infant formula largely because of concerns over possible accumulation of triglyceride in heart as a result of the small amounts of erucic acid (22∶1n−9) in the oil. Therefore, the concentration and composition of heart triglyceride were determined in piglets fed from birth for 10 (n=4–6) or 18 (n=6) d with formula containing about 50% energy fat as 100% canola oil (0.5% 22∶1n−9) or 100% soybean oil, or 26% canola oil or soy oil (blend) with palm, high-oleic sunflower and coconut oil, providing amounts of 16∶0 and 18∶1 closer to milk, or a mix of soy, high-oleic sunflower and flaxseed oils with C₁₆ and C₁₈ fatty acids similar to canola oil but without 22∶1. Biochemical analysis found no differences in heart triglyceride concentrations among the groups at 10 or 18 d. Assessment of heart triglycerides using Oil Red O staining in select treatments confirmed no differences between 10-d-old piglets fed formula with 100% canola oil (n=4), 100% soy oil (n=4), or the soy oil blend (n=2). Levels of 22∶1n−9 in heart triglyceride and phospholipid, however, were higher (P<0.01) in piglets fed 100% canola oil or the canola oil blend, with higher levels found in triglycerides compared with phospholipids. The modest accumulation of 22∶1n−9 associated with feeding canola oil was not associated with biochemical evidence of heart triglyceride accumulation at 10 and 18 d.     

Trans fatty acids. 3. Fatty acid composition of the brain and other organs in the newborn piglet

The effects of dietarytrans fatty acids on tissue fatty acid composition were studied in newborn piglets delivered from sows fed partially hydrogenated fish oil (PHFO) (28%trans) or partially hydrogenated soybean oil (PHSBO) (36%trans) in comparison with lard (0%trans) from 3 wk of age and through gestation in Experiment 1, or fed PHFO or “fully” hydrogenated fish oil (HFO) (19%trans) in comparison with coconut oil (CF) (0%trans) with two levels, 1 and 2.7%, of dietary linoleic acid from conception through gestation in Experiment 2. The piglets were sampled immediately after delivery, without having access to mothers' milk. Incorporation oftrans fatty acids into brain PE (phosphatidylethanolamine) were non-detectable or very low (less than 0.1%). The incorporation of 18∶1trans into heart-PE, liver mitochondria-PE, total plasma lipids and adipose tissue was low, and 20∶1trans was not detected. Dietarytrans fatty acids had no consistent effects on the overall fatty acid composition of the different tissue lipids. It is conclude thattrans fatty acids from PHFO, HFO and PHSBO have no significant effects on the fatty acid accretion in the fetal piglet.     

Trans fatty acid isomers in Canadian human milk

The fatty acid composition, totaltrans content (i.e., sum of all the fatty acids which may have one or moretrans double bonds) and geometric and positional isomer distribution of unsaturated fatty acids of 198 human milk samples collected in 1992 from nine provinces of Canada were determined using a combination of capillary gas-liquid chromatography and silver nitrate thin-layer chromatography. The mean totaltrans fatty acid content was 7.19±3.03% of the total milk fatty acids and ranged from 0.10 to 17.15%. Twenty-five of the 198 samples contained more than 10% totaltrans fatty acids, and thirteen samples contained less than 4%. Totaltrans isomers of linoleic acid were 0.89% of the total milk fatty acids with 18∶2Δ9c, 13t being the most prevalent isomer, followed by 18∶2Δ9c, 12t and 18∶2Δ9t, 12c. Using the totaltrans values in human milk determined in the present study, the intake of totaltrans fatty acids from various dietary sources by Canadian lactating women was estimated to be 10.6±3.7 g/person/d, and in some individuals, the intake could be as high as 20.3 g/d. The 18∶1trans isomer distribution differed from that of cow's milk fat but was remarkably similar to that in partially hydrogenated soybean and canola oils, suggesting that partially hydrogenated vegetable oils are the major source of thesetrans fatty acids.     

Compositions of commercial corn and soybean lecithins

The lipid and fatty acid compositions of commercial corn and soybean lecithins were compared. The types of lipids were similar, but the proportions varied. The ratio of glycolipids to phospholipids was 0.36 for corn lecithin and 0.14 for soybean. Phosphatidylcholine and phosphatidylinositol were major phospholipids in both lecithins. In soybean lecithin, the percentage of phosphatidyleth-anolamine equaled that of phosphatidylinositol, but in corn, the percentage of phosphatidylethanolamine was only about one-fourth the percentage of phosphatidylinositol. High levels of phosphatidic acid in both the corn and soybean preparations indicated some degradation of the phospholipids during processing. The major differences in fatty acid compositions were a higher percentage of oleic acid and lower percentages of stearic and linolenic acids in corn compared to soybean. The lower level of linolenic acid should give corn lecithin greater resistance toward autoxidation and the development of off-flavors.     

Human erythrocyte phosphoglycerides. II. Diet and lecithin structure

Lecithins (separated on basic silicic acid columns) were obtained from humans fed three different diets: eitherad-libitum or diets containing 40% of calories from linoleic acid (as corn oil) or from oleic acid (as triolein). Four lecithin subfractions were studied from each dietary group. Lecithin fractions eluting earliest (and apparently the least polar) contained the highest molar ratios of unsaturated fatty acids and the highest proportion of C-20 to C-22 polyunsaturated fatty acids. A slight increase in proportions of diunsaturated molecules occurred in corn oil and triolein groups. However, over 90% of lecithins of each dietary group were maintained as themonosaturated - monounsaturated type. Therefore, in contrast to human adipose tissue triglycerides, the saturated/unsaturated fatty acid ratio of lecithins of the erythrocyte membrane is largely unaffected by immense increases in dietary unsaturated fatty acid. Major shifts of oleic and linoleic acid occurred but proportions were unaltered of longer chain length (>C-18) polyunsaturated fatty acids. The relevance of these findings to membrane structure and function and to glycerophosphatide biosynthesis is discussed.     

Determination of the structure of lecithins via the formation of acetylated 1,2-diglycerides

A detailed procedure for quantitative determinations of molecular species of lecithins is described and applied to several lecithins isolated from natural sources. The method is based on the conversion of lecithin to acetylated 1,2-diglycerides and analysis of these compounds by methodology used for the determination of triglyceride structure. The preparation of the acetylated 1,2-diglycerides was carried out via hydrolysis with phospholipase C and acetylation of the resultant, 1,2-diglycerides with pyridine-acetic anhydride. Preparation of acetylated 1,2-diglycerides from lecithin by acetolysis with acetic acid-acetic anhydride was shown to be accompanied by intermolecular as well as intramolecular rearrangement of the fatty acids. The structure of the acetylated 1,2-diglycerides was determined by a combination of argentation-TLC and pancreatic lipase hydrolysis using internal standards for quantification. The method was applied to lecithins isolated from milk serum, egg, soybean, safflower seed and wheat germ lipids.     

Microalgae as a Feedstock for Sustainable Fatty Acids: Factorial Design Study

Microalgal oil from Nannochloropsis gaditana cultivated in a laboratory-scale photobioreactor was submitted to enzymatic hydrolysis using Candida rugosa lipase. A 2² full factorial design was performed to evaluate the effects of the soy lecithin emulsifier concentration and the lipase loading on the formation of free fatty acids. As control, a similar set of reactions was carried out with macaw palm oil. The results showed similar hydrolysis yields for both feedstocks. The highest value was reached when the concentrations of soy lecithin and lipase were taken at their lowest and highest levels, respectively. The hydrolysate from microalgal oil showed that the majority of the fatty acids released by C. rugosa consisted of palmitic, oleic, and linoleic acids.     

Polymorphic and microstructural behaviors of palm oil/lecithin blends crystallized under shear

There has been much work on polymorphism and crystal habit of quiescently crystallized palm oil. However, researchers have found it difficult to probe the process of sheared crystallization. The effect of surface-active molecules as nucleation agents or habit modifiers was demonstrated in quiescent systems. The aim of this work is to explore the effects of shear and specific lecithins (soy and sunflower) on palm oil crystallization by monitoring crystallization under shear using a synchrotron radiation source, as well as microscopy and DSC. It was found that increasing shear led to increasing β′ stabilization in all situations. Soybean lecithin had little effect on behavior. Sunflower lecithin led to even greater β′ stabilization. The different lecithins interact with the crystallizing fat changing rates of nucleation and crystal growth. Thus, the structure of the overall system can be dramatically altered. Microscopy revealed very different structures even if the polymorphism of the different systems was similar. Consequently, specific interactions can be manipulated in order to control the system. In particular, control of lecithin composition affects the stability of the different polymorphs. Palm oil crystallization under realistic processing conditions has been characterized. Under these conditions, increasing shear rates give higher β′ stability. Specific lecithins have different effects. In particular, soybean lecithin is β′ stabilizing, whereas sunflower lecithin has limited effects. Thus the overall structure of lecithin is important in determining the efficacy. This can be applied to control the structure and properties of different systems such as shortenings or spreads where crystalline interactions create the macro-structure that determines product properties.     

Effects of superfatting agents on cracking phenomena in toilet soap

Palm stearin (POs) is one of the cheapest sources of C16–C18 fatty acids for use in soap making. Toilet-soap formulations containing a high content of POs, however, would result in hard soaps with a tendency to form cracks on the surface. This phenomenon can be overcome by addition of superfatting agents to increase plasticity of the finished product. In this study, two different blends of soap made from distilled POs, palm oil (PO), and palm kernel oil (PKO) fatty acids in the ratio of 40POs/40PO/20PKO and 70POs/30PKO were evaluated. The soaps were superfatted with glycerin, palm kernel olein, coconut oil, olive oil and canola oil. The levels of incorporation of each superfatting material were 1, 2, 4, and 6%, respectively. The samples were subsequently tested for both wet and dry crackings using the Hewitt Soap Company methods (numbers 78 and 79, respectively). The superfatted soaps had a total fatty matter of 73–83% and an average moisture content of 10%. The penetration value which indicates hardness increased with increasing amount of superfatting agents. Foaming or lathering property was good with the exception of the formulation using palm kernel olein and canola oil as superfatting agents. At all the above levels of superfatting agents added, no cracks were observed during both wet and dry cracking tests. A sample of soap superfatted with 2% canola oil, however, developed cracks during the wet cracking test. This resulted in a test score of 7. Superfatting soaps with 1–2% neutral oils or glycerin resulted in better quality soaps that were free of cracks.     

<Emphasis Type="Italic">Trans</Emphasis>–<Emphasis Type="Italic">trans</Emphasis> Conjugated Linoleic Acid Enriched Soybean Oil Reduces Fatty Liver and Lowers Serum Cholesterol in Obese Zucker Rats

Conjugated linoleic acid (CLA) is a collection of octadecadienoic fatty acids that have been shown to possess numerous health benefits. The CLA used in our study was produced by the photoisomerization of soybean oil and consists of about 20% CLA; this CLA consists of 75% trans–trans (a mixture of t8,t10; t9,t11; t10,t12) isomers. This method could be readily used to increase the CLA content of all soybean oil used as a food ingredient. The objective of this study was to determine the effects of trans–trans CLA-rich soy oil, fed as a dietary supplement, on body composition, dyslipidemia, hepatic steatosis, and markers of glucose control and liver function of obese fa/fa Zucker rats. The trans–trans CLA-rich soy oil lowered the serum cholesterol and low density lipoprotein–cholesterol levels by 41 and 50%, respectively, when compared to obese controls. Trans–trans CLA-rich soy oil supplementation also lowered the liver lipid content significantly (P < 0.05) with a concomitant decrease in the liver weight in the obese rats. In addition, glycated hemoglobin values were improved in the group receiving CLA-enriched soybean oil in comparison to the obese control. PPAR-γ expression in white adipose tissue was unchanged. In conclusion, trans–trans CLA-rich soy oil was effective in lowering total liver lipids and serum cholesterol.     

Indian ricebran lecithin

In view of the high potential of ricebran oil in India, lecithins recovered from crude and dewaxed Indian ricebran oil were analyzed and different classes characterized with the objective of effectively utilizing this valuable by- product. Lipid classes and individual phospholipid components were identified and estimated. Dewaxing was found to have a considerable effect on composition of the derived lecithin. The lecithin obtained from crude or dewaxed Indian ricebran oil consisted mainly of phosphatidylcholine, phosphatidylethanolamine, phosphatidylnositol and triglycerides, along with carbohydrates, free fatty acid, sterols and waxes (in case of crude oil). The major fatty acids of individual phospholipids were found to be palmitic, oleic and linoleic. Analytical characteristics of ricebran lecithin were shown to be comparable to local soybean lecithin. It can be expected that the gummy materials in the oil, presently lost with the soapstock during refining, could find important applications.     

Lecithins in oil-continuous emulsions. Fat crystal wetting and interfacial tension

Lecithin is a powerful emulsifier widely used in foods, feeds and pharmaceuticals. Several analytical methods have been proposed to characterize lecithins, but they are often inadequate to determine the industrial functionality. The purpose of this study was to find a relationship between the interfacial properties of lecithins (adsorption to oil/water and fat crystal/oil/water interfaces), phospholipid composition and functionality. Results show that all lecithins adsorb to fat crystals at the triglyceride oil/water interface, making their surface more polar (observed as an increase in the contact angle measured through the oil at the interface: fat crystal/oil/water). This adsorption process is quick (less than five minutes) for relatively polar lecithins, such as soybean phosphatidylcholine (PC), and results in highly polar surfaces (contact angle ∼180°). Less polar lecithins give slow adsorption (some hours) and less polar crystals (contact angle ≤90°). The adsorption of different lecithins to the oil/water interface, observed as a decrease in interfacial tension, follows the adsorption pattern to the fat crystals. We found a relation between high-fat crystal polarity and poor lecithin functionality in margarine (margarines spatters during frying), and also between high-fat crystal polarity and a high polar to nonpolar phospholipids [Σ(PI + PA + LPC)/ΣPE; PI, phosphatidylinositol; PA, phosphatidic acid; LPC, lysoPC, PE, phosphatidylethanolamine] ratio in lecithin. The correlations might bevia aggregation properties of lecithin in the oil. We found also that monoolein shifted the adsorption kinetics of lecithin (soybean PC) to fat crystals and the hydrophilicity of adsorbed layers probably due to formation of mixed aggregates between monoolein and soybean PC.     

Soy lecithin-monoester interchange reaction by microbial lipase

Modification of the fatty acid composition of soy lecithin, principally at its 1-position, was investigated by interchange reaction with the methyl ester of individual fatty acids and a lipase as the catalyst. The consequent effect on the surface activity of soy lecithin was also examined. The interchange reaction was carried out by heating a mixture of soy lecithin and methyl ester of a fatty acid at 60°C for 48 h with 10% (by weight of the reactants) Mucor miehei lipase. The lipase was filtered from the reaction mixture, and the product was isolated by combination of acetone extraction, which removed the methyl ester fraction, and by preparative thin-layer chromatography separation. The soy lecithin showed distinct change in its fatty acid composition in the sn-1 position. Capric acid was incorporated by 8.4%, while lauric acid and myristic acid were introduced at 14.1 and 15.7%, respectively. The linolenic acid percentage was increased by about 10 units. The interfacial tension of soy lecithin changed significantly after incorporation of various saturated fatty acids.     

Mapping the Chemical Variability of Vegetable Lecithins

There is an increasing interest in vegetable lecithins because of their broad usage in many food and cosmetic applications. In this research, the chemical variability of commercial lecithins from soy, sunflower and rapeseed were mapped. The acetone insoluble matter, total phospholipid content and their compositions were determined. Significant correlation coefficients were observed between phosphatidylcholine and phosphatidic acid (?0.84), phosphatidylethanolamine and phosphatidylinositol (?0.86), monounsaturated fatty acid and polyunsaturated fatty acid (?0.97). Principal component analysis was used to group the lecithins according to their sources. Rapeseed lecithin was found to be the most different product compared to soy and sunflower lecithin.     

Canola Proteins Used as Co‐Emulsifiers with Phospholipids Influence Oil Oxidability,Enzymatic Lipolysis,and Fatty Acid Absorption in Rats

The objective of this study is to formulate and characterize oil‐in‐water emulsions with plant‐derived ingredients only, that is, proteins extracted from canola oil bodies, used as co‐emulsifiers with a canola lecithin, and to assess their suitability for food applications. Using the protein extract increases the chemical stability of rapeseed oil emulsions toward oxidation, based on the delay in conjugated diene formation under accelerated storage conditions, and favors pancreatic lipase activity. Bioaccessibility of rapeseed fatty acids is compared in lymph‐duct‐cannulated rats fed oil or emulsion. Fatty acid absorption by the intestine is increased by 78% when the oil is emulsified with canola proteins as co‐emulsifier: 28.7 mg mL^?1 versus 16.1 mg mL^?1 for oil (p < 0.05). In vitro lipolysis results are in overall agreement with fatty acid absorption in vivo. Practical Applications: Results obtained for rapeseed oil emulsified with canola proteins and phospholipids suggest that increased bioaccessibility of n‐3 polyunsaturated fatty acids could be offered in vegan food products.