Influence of feeding soybean oil on conjugated linoleic acid content in beef

Forty-eight steers were used to study the influence of feeding soybean oil (SO) on the conjugated linoleic acid (CLA) content of beef. Steers were fed either a control diet containing 954 g/kg of dry matter (DM) corn-based concentrate (CTL) or a control diet supplemented with SO at 20 (SO2) or 40 g/kg (SO4) of diet DM for 105 days. Adipose tissue samples were collected from the M. longissimus dorsi (LD) and from the M. semitendinosus (ST) on days 0 and 63 of the experiment. Adipose and muscle tissue samples were collected from the LD and ST immediately after slaughter. Feeding 40 g/kg of DM as SO increased the proportions of trans-C(18:1) in beef lipid as compared to CTL and SO2 treatments. The C(18:2) cis-9, trans-11 isomer of CLA as a proportion of total fat was not different in adipose and muscle across treatments. Supplementing SO increased C(18:2) trans-10, cis-12 CLA in adipose tissue of the LD. Supplementing high-grain finishing diets with SO is not an effective strategy to enhance the C(18:2) cis-9, trans-11 isomer of CLA in beef.     

Effect of antioxidants on soy oil conjugated linoleic acid production and its oxidative stability

Conjugated linoleic acid (CLA)-rich soy oil can be produced by photoisomerization of soy oil linoleic acid to produce a soy oil with up to 20% CLA. Recent studies indicate that mixed soy tocopherols added to refined bleached deodorized (RBD) oil produced significant increase in soy CLA yield during soy oil linoleic acid photoisomerization. However, the effect of common synthetic free radical scavenging antioxidants and specific tocopherols on CLA yield and its oxidative stability is not known. Therefore, this investigation evaluated the effects of various antioxidant systems on soy oil CLA yield and oxidative stability. Soy oil with added antioxidants consisting of combinations of mixed tocopherols (MT), ascorbyl palmitate (AP), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and tert-butylhydroquinone (TBHQ) was photoisomerized to produce CLA- rich soy oil. The CLA content was determined by GC-FID analysis and oxidative stability by peroxide value (PV). The soy oil in the presence of TBHQ, MT alone and MT with 500 ppm of AP produced significantly greater CLA yields and improved oxidative stability compared to a control without added antioxidants (p < 0.05). However, added mixed tocopherols produced the greatest CLA yield and also reduced PV relative to the control. Tocopherols in the form of α-, γ- and δ-tocopherols were then each examined as to their relative effect on CLA yields and PV. The largest increase in CLA yield was obtained with 1800 ppm of γ-tocopherols with reduced PV. Mixed tocopherols, TBHQ and γ-tocopherols can be used to increase CLA yield and reduce PV of soy oil during linoleic acid photoisomerization.     

Photocatalytic production and processing of conjugated linoleic acid-rich soy oil

Daily intake of conjugated linoleic acid (CLA), an anticarcinogenic, antiatherosclerotic, antimutagenic agent, and antioxidant, from dairy and meat products is substantially less than estimated required values. The objective of this study was to obtain CLA-rich soybean oil by a customized photochemical reaction system with an iodine catalyst and evaluate the effect of processing on iodine and iodo compounds after adsorption. After 144 h of irradiation, a total CLA yield of 24% (w/w) total oil was obtained with 0.15% (w/w) iodine. Trans,trans isomers (17.5%) formed the majority of the total yield and are also associated with health benefits. The isomers cis-9,trans-11 and trans-10,cis-12 CLA, associated with maximum health benefits, formed approximately 3.5% of the total oil. This amount is quite significant considering that total CLA obtained from dairy sources is only 0.6%. ATR-FTIR, 1H NMR, and GC-MS analyses indicated the absence of peroxide and aldehyde protons, providing evidence that secondary lipid oxidation products were not formed during the photochemical reaction. Adsorption processing vastly reduced the iodine and iodocompounds without CLA loss. Photocatalysis significantly increased the levels of CLA in soybean oil.     

Partial inhibition of biohydrogenation of linoleic acid can increase the conjugated linoleic acid production of Butyrivibrio fibrisolvens A38

Butyrivibrio fibrisolvens A38, one of the most active rumen bacteria in conjugated linoleic acid (CLA) production, was characterized in vitro. Previous findings that some inhibitory levels of substrate for biohydrogenation (BH) by B. fibrisolvens A38 resulted in more CLA accumulation led to a prediction that partial inhibition of BH could increase ruminal CLA production. The inhibitory conditions for bacterial growth were less effective on the isomerization step than on the following reduction step. Linoleic acid (LA) was inhibitory not only to cell growth but also to LA hydrogenation, and this effect was greater at high concentrations. The reduction step, converting CLA to hydrogenated products (trans-C18:1 and C18:0), was significantly inhibited, and more CLA accumulated during aerobic incubation when LA was added along with a glycolytic inhibitor, iodoacetate (IAA), to cells that were pre-adapted to LA (1 g/OD at 600 nm/L, P < 0.05). Monensin was more inhibitory than IAA to cell growth but less effective for CLA accumulation. Rumen fluid in the culture medium appeared to activate BH even in an aerobic condition, resulting in a lower CLA level than the control group (P < 0.05). Because the isomerization and reduction steps are coupled reactions in BH of most hydrogenating bacteria including B. fibrisolvens A38 cells, both positive and negative modulations of the reduction steps could be key determinants for CLA accumulation in the rumen.     

Antioxidant evaluation and oxidative stability of structured lipids from extravirgin olive oil and conjugated linoleic acid

Structured lipid (SL) was synthesized from extravirgin olive oil (EVOO) and conjugated linoleic acid (CLA) via a lipase-catalyzed reaction. CLA provides a variety of health benefits, but it is not consumed in free fatty acid form. The synthesized SL olive oil contained 42.5 mol % CLA isomers, and the major isomers were cis-9,trans-11-CLA (16.9 mol %) and trans-10,cis-12-CLA (24.2 mol %). The antioxidant activity determined by the radical scavenging capacity with the 2,2-diphenyl-1-picrylhydrazyl radical was lower in SL olive oil than in EVOO. The oxidative stability was also lower in SL olive oil since it had a higher peroxide value, rho-anisidine value, and 2-thiobarbituric acid reactive substances values during 20 days of storage at 60 degrees C. This observation could be due to the reduction in the natural phenolic compounds (97%) and tocopherols (56%), and the incorporated CLA with two conjugated double bonds in the SL olive oil. The oxidative stability of SL olive oil was increased by added rosemary extracts at concentrations of 100, 200, and 300 ppm. The present study suggests that the SL olive oil may be a suitable way to incorporate or deliver CLA into human diets. However, the addition of a proper antioxidant would be required for improving its oxidative stability.     

Effect of the degree of processing on soy oil conjugated linoleic acid yields

Photoirradiation processing can be used to rapidly synthesize conjugated linoleic acid (CLA) in large quantities in soy oil. The objective of this study was to evaluate the effect of the level of refining of soy oil on CLA yields and oxidative properties after photoirradiation. Crude, alkali-refined, alkali-refined bleached, and alkali-refined bleached and deodorized (RBD) soy oils were photoirradiated in a pilot-plant processing system for 12 h with 0.35% iodine catalyst at 47 degrees C. RBD soy oil gave the highest total CLA yield of 16.3% of total oil with 4.3% cis, trans- and trans, cis-CLA isomers. Oxidative stability as measured by weight gain during incubation at 64 degrees C showed that iodine decreased the induction time of soy oil samples by 2-4 days. Photoirradiation processing further decreased the induction time by 2 days as a result of loss of total tocopherols. Iodine addition increased the titratable acidity in all the samples of soy oil. However, the level of refining affects this increase of titratable acidity, and RBD soy oil was found to be the most stable. The study indicates that RBD soy oil was the most suitable candidate for photoirradiation processing. Thus, soy oil should be alkali-refined, bleached, deodorized, and then photoprocessed followed by a secondary adsorption step to remove the iodine catalyst to obtain a RBD CLA-rich soy oil.     

Oxidative stability of conjugated linoleic acid isomers

Conjugated linoleic acids (CLAs) have been shown to be a strong anticarcinogen in a number of animal models. Our previous study demonstrated that CLA as a whole was extremely unstable in air. The present study was undertaken further to examine the oxidative stability of individual CLA isomers using the combination of gas-liquid chromatography (GLC) and silver ion high-performance liquid chromatography (Ag-HPLC). It was found that CLA as a whole oxidized rapidly and more than 80% was degraded within 110 h in air at 50 degrees C. Four c,c-CLA isomers were most unstable followed by four c,t-CLA isomers. In contrast, four t,t-CLA isomers were relatively stable under the same experimental conditions. Both the oxygen consumption and the GLC analysis revealed that 200 ppm jasmine green tea catechins (GTCs) exhibited protection to CLA and were even stronger than 200 ppm butylated hydroxytoluene (BHT) when added to either CLA or canola oil containing 10% CLA. The present study emphasized that oxidative unstability of CLA should not be overlooked although CLA has many biological effects.     

Formation of conjugated linoleic acids in soybean oil during hydrogenation with a nickel catalyst as affected by sulfur addition

The effects of sulfur addition on the formation of conjugated linoleic acid (CLA) isomers were studied during the hydrogenation of soybean oil with a nonselective type nickel catalyst. Sulfur addition greatly promoted CLA formation in soybean oil during hydrogenation. As the amount of sulfur increased to a certain level, the maximal quantity of CLA in soybean oil during hydrogenation increased greatly. However, further increase in sulfur addition above the certain level decreased CLA formation. The optimal sulfur level for the promotion of CLA formation differed greatly with the amount of nickel used. It was of great interest to find that the optimal ratio of sulfur to nickel for the promotion of CLA formation was always 0.06:1, regardless of the nickel amount used. At the same ratio of sulfur to nickel, higher nickel content induced significantly higher production of CLA (p < 0.05). At the optimal sulfur to nickel ratio, an increase in the nickel amount from 0.05 to 0.15% produced approximately 1.5 times higher levels of CLA during hydrogenation under the tested conditions. The CLA isomer compositions were greatly affected by both sulfur addition and amounts of nickel used for treatment. This is the first report of the possibility that the total quantity of CLA and their isomer composition could be manipulated during hydrogenation by controlling the amounts of sulfur and nickel.     

Effects of rhodium heterogeneous catalyst and isomerization conditions on linoleic acid conjugation of soybean oil

Rhodium heterogeneous catalyst was used to catalyze isomerization of linoleic acid in soybean oil to conjugated linoleic acid (CLA). A central composite rotatable design with five levels of three variables, namely, reaction temperature, stirring speed, and reaction time, was used to determine the maximum CLA yield. The formation of CLA during isomerization was greatly dependent on the reaction temperature and time. The CLA content of soybean oil increased from 0.63 to 202.42 mg/g oil when isomerization was done at 200 degrees C, with a stirring speed of 200 rpm for 49 min. Analysis of triacylglycerol positions showed that linoleic acid at any position in a triacylglyceride could possibly be isomerized to CLA.     

Effects of temperature and agitation rate on the formation of conjugated linoleic acids in soybean oil during hydrogenation process.

The effects of hydrogen temperature and agitation rate on the formation of total conjugated linoleic acids (CLA) and CLA isomers were studied during hydrogenation with a selective Ni catalyst. The CLA isomers were identified by using a 100-m cyano-capillary column gas chromatograph and a silver ion-impregnated HPLC. Reaction temperature and agitation rate greatly affected the quantities of total CLA and individual CLA isomers, and the time to reach the maximum quantity of CLA in the partially hydrogenated soybean oil. As the hydrogenation temperature increased, the maximum quantity of CLA in soybean oil increased, but the time to reach the maximum CLA content decreased. By increasing the hydrogenation temperature from 170 to 210 degrees C, the quantity of CLA obtained was about 2.6 times higher. As the agitation rate decreased, the CLA formation in soybean oil increased, and the time to reach the maximum CLA content also increased. The maximum CLA contents in soybean oil obtained during hydrogenation at 210 degrees C with agitation rates of 300, 500, and 700 rpm were 162.82, 108.62, and 66.15 mg total CLA/g oil, respectively. The present data showed that it is possible to produce high-CLA-content soybean oil without major modification of fatty acid composition by short-time (10 min) selective hydrogenation under high temperature and low agitation rate conditions.     

Microbially safe utilization of non-inactivated oats (Avena sativa L.) for production of conjugated linoleic acid

A microbially safe process for the enrichment of conjugated linoleic acid (CLA) in oats was developed. The process consists of hydrolysis of oat lipids by non-inactivated oat flour, followed by propionibacterium-catalyzed isomerization of the resulting free linoleic acid to CLA. The first stage was performed at water activity (a(w)) 0.7, where hydrolysis of triacylglycerols progressed efficiently without growth of the indigenous microflora of flour. Thereafter, the flour was incubated as a 5% (w/v) aqueous, sterilized slurry with Propionibacterium freudenreichii ssp. shermanii. The amount of CLA produced in 20 h was 11.5 mg/g dry matter corresponding to 116 mg/g lipids or 0.57 mg/mL slurry. The oat flour had also the capability to hydrolyze exogenous oils at a(w) 0.7. Sunflower oil, added to increase linoleic acid content in triacylglycerols 2.7-fold, was hydrolyzed rapidly. Isomerization of this oil-supplemented flour as a 5% slurry gave final CLA content of 22.3 mg/g dry matter after 50 h of fermentation, corresponding to 118 mg/g lipids or 1.14 mg/mL slurry. Storage stability of CLA in fermented oat slurries at 4 degrees C was good.     

Conjugated linoleic acid isomers in partially hydrogenated soybean oil obtained during nonselective and selective hydrogenation processes

Partially hydrogenated soybean oil samples were collected during selective and nonselective hydrogenation processes. The formation of conjugated linoleic acids (CLAs) during hydrogenation was greatly dependent on the types and duration of hydrogenation processes. During hydrogenation processes, CLA contents increased initially. After reaching maximum CLA content, the content decreased during hydrogenation. Selective hydrogenation was much more favorable for the formation of conjugated linoleic acids. With nonselective hydrogenation process, the total CLA content was a maximum (9.06 mg total CLA/g oil) at 35 min. However, with the selective hydrogenation process, the total CLA content was a maximum (98.27 mg total CLA/g oil) at 210 min. The CLA contents in some of the tested selectively hydrogenated soybean oils were among the highest ever reported in foods.     

Positional distribution of conjugated linoleic acid in triacylglycerol of Saccharomyces cerevisiae

Saccharomyces cerevisiae was cultivated in the presence of cis-9,trans-11 or trans-10,cis-12 isomers of free conjugated linoleic acid (CLA), and the effects of the isomers on the regioisomerisms of triacylglycerol (TAG) of the yeast were elucidated. Both isomers constituted about 34% of all fatty acids and increased drastically the number of different TAG species. Nearly all of the species contained CLA in at least one sn-position. In the most abundant species analyzed (20% of total species), the cis-9,trans-11 isomer appeared in combination with monounsaturated fatty acids (C16:1, C:18:1) whereas trans-10,cis-12 isomer was most frequently present with a medium chain fatty acid (C10:0 or C12:0) in the sn-2 position and C16:0 in one of the end positions (14% of total species). With either isomer, the amount of TAG species in which CLA encompassed all sn-positions was ca. 4%. Thus, S. cerevisiae can be used to produce edible single cell oil characterized by very heterogeneous distribution of CLA among the different TAG species.     

Differential incorporation of conjugated linoleic acid isomers into egg yolk lipids

The incorporation pattern of conjugated linoleic acids (CLA) isomers into the egg yolk of hens in relation to that in the diet was studied. Silver-ion high-performance liquid chromatography (Ag-HPLC) was used to separate individual CLA isomers. It was found that the isomeric distribution pattern in the egg yolk lipids was different from that in the dietary fat. Total cis/trans isomers accounted for 81.2% of total CLA incorporated into the egg yolk, which was in contrast to the value of 92.0% of total CLA in the diet. Total cis/cis isomers accounted for 3.8% total CLA in the diet but they were 6.6% of the total CLA in the egg yolk lipids. In contrast, total trans/trans isomers were 12.2% of the total CLA isomers in the egg yolk lipids, whereas they were only 4.2% of total CLA in the diet. The results showed that total trans/trans-CLA was preferentially incorporated into the egg yolk, whereas the incorporation of total cis/trans-CLA isomers was partially discriminated. Within each group, the incorporation of individual isomers into the egg yolk lipids was also selective. cis-9,trans-11/trans-9,cis-11 and cis-10,trans-12/trans-10,cis-12 were the two major isomers in the diet. Ag-HPLC analysis showed that the former was preferentially transferred into the egg yolk compared with the latter. It was observed that supplementation of CLA in the diet of laying hens decreased the concentration of oleic acid (18:1n-9), arachidonic acid (20:4n-6), and docosahexaenoic acid (22:6n-3) but increased that of linolenic acid (18:3n-3), stearic acid (18:0), and palmitic acid (16:0) in the egg yolk, suggesting that CLA may inhibit Delta6 and Delta9 desaturases.     

Inclusion complex of conjugated linoleic acid (CLA) with cyclodextrins

Conjugated linoleic acid (CLA) inclusion complexes with alpha-cyclodextrin (alpha-CD), beta-cyclodextrin (beta-CD), and gamma-cyclodextrin (gamma-CD) (designated CLA/CDs inclusion complexes) were prepared to determine the mole ratio of CLA complexed with CDs and the oxidative stability of CLA in the CLA/CDs inclusion complexes. When measured by GC, (1)H NMR, and T(1) value analyses, 1 mole of CLA was complexed with 5 mol of alpha-CD, 4 mol of beta-CD, and 2 mol of gamma-CD. The oxidation of CLA induced at 35 degrees C for 80 h was completely prevented by the formation of CLA/CDs inclusion complexes.     

Dietary combination of conjugated linoleic acid (CLA) and pine nut oil prevents CLA-induced fatty liver in mice

Conjugated linoleic acid (CLA) strongly prevents fat accumulation in adipose tissue of mice, even if hepatic fat deposition and insulin resistance are concomitantly observed. This study investigated the possibility of maintaining the antiadiposity properties of CLA while preventing adverse effects such as liver steatosis and hyperinsulinemia. To this end, mice were divided into three groups and fed a standard diet (control) or a diet supplemented with 1% CLA (CLA) or a mixture of 1% CLA plus 7.5% pine nut oil (CLA + P). The combination of CLA + P preserved the CLA-mediated antiadiposity properties (70% fat reduction), preventing hepatic steatosis and a sharp increase in plasmatic insulin starting from the eighth week of CLA treatment. The assay of both fatty acid synthesis and oxidation in the CLA + P mice revealed a time-dependent biphasic behavior of the corresponding enzymatic activities. A sudden change in these metabolic events was indeed found at the eighth week. A strong correlation between the changes in key enzymes of lipid metabolism and in insulin levels apparently exists in CLA-fed mice. Furthermore, lower levels of lipids, in comparison to values found in CLA-fed mice, were observed in the liver and plasma of CLA + P-fed animals.     

Determination of conjugated linoleic acid (CLA) concentrations in milk chocolate

The fatty acids from a series of milk-chocolate-based confectionery samples were analyzed as methyl esters by GC to determine the presence and amount of conjugated linoleic acid (CLA). A single peak corresponding to the 9-cis,11-trans isomer and ranging from less than 0.1% to nearly 0.2% of the total fatty acids, corresponding to up to 0.3 mg per g of chocolate, was observed. One of the chocolate extracts and a milk extract were subjected to silver ion HPLC and GC-MS in order to confirm the identity of the major isomer and tentatively identity minor isomers.     

Identification of conjugated linoleic acids in hydrogenated soybean oil by silver ion-impregnated HPLC and gas chromatography-ion impacted mass spectrometry of their 4,4-dimethyloxazoline derivatives

Hydrogenated soybean oil was obtained after 10 min of hydrogenation with 0.5% selective type Ni catalyst at 230 degrees C, a hydrogenation pressure of 0.049 MPa, and an agitation rate of 300 rpm. The conjugated linoleic acid isomers in the hydrogenated soybean oil were isolated by using a silver ion-impregnated HPLC. Gas chromatography-mass spectrometry of 4,4-dimethyloxazoline (DMOX) derivatives of the isolated conjugated linoleic acid isomers were carried out for the identification of their chemical structures. By interpreting the mass spectra of the DMOX derivatives of conjugated linoleic acid isomers isolated by silver ion-impregnated HPLC, 20 different conjugated linoleic acid isomers present in hydrogenated soybean oil were identified. This is the first report for the mass spectrometric identification of the conjugated linoleic acid isomers present in hydrogenated vegetable oil.     

Utilization of monolinolein as a substrate for conjugated linoleic acid production by Bifidobacterium breve LMC 520 of human neonatal origin

This study was designed to isolate bifidobacteria from human intestines that efficiently converts monolinolein, a monoglyceride form of linoleic acid, into conjugated linoleic acid (CLA), as well as to optimize culture conditions for improving CLA production during milk fermentation. Among 150 screened neonatal bifidobacteria, Bifidobacterium breve LMC 520 showed the highest CLA-producing ability and was tested with different types of fat substrates at various concentrations to determine the optimal conditions for CLA production. Monolinolein was tested as a substrate for CLA production. The incubation time optimized for CLA production was 24 h, and CLA production was proportionally increased with monolinolein concentration. The incubation of LMC 520 with commercial starter strains caused minimal reduction in CLA production. Our results demonstrate that the CLA-producing ability of B. breve LMC 520 could offer beneficial effects when utilized as a starter culture for the development of functional dairy products.     

共轭亚油酸水包油型乳液的物理化学稳定性

共轭亚油酸（conjugated linoleic acid, CLA）是一种具有多重生理功效的不饱和脂肪酸,其氧化稳定性较差,对光、热、氧气很不稳定。以亲水胶体为乳化剂制备CLA的水包油（O/W）型乳液可改善其氧化稳定性,扩大其在食品中的应用。该研究采用改性阿拉伯胶EM2为乳化剂、2种不同黏度的CLA为油相,通过测定乳液颗粒的粒径和粒径分布以及乳液在40℃贮存过程中的过氧化值和茴香胺值,研究了CLA的水包油（O/W）型乳液的物理化学稳定性。结果表明,高质量分数的EM2有利于形成粒径更小且分布均一的乳液颗粒。乳液的氧化稳定性很大程度上依赖于其物理稳定性。对于黏度较小的CLA,在各测试EM2质量分数下,CLA乳液具有较好的物理稳定性,且随着EM2质量分数的增大,乳液氧化稳定性提高。对于黏度较大的CLA,EM2质量分数为5%时,乳液具有较好的物理化学稳定性;增大EM2的质量分数,其稳定性下降。该研究可为今后研究基于乳液技术的功能性因子保护和增效提供参考,有利于CLA在食品行业中的推广应用。