Effects of conjugated linoleic acid (CLA) isomers on oxygen diffusion-concentration products in liposomes and phospholipid solutions

Conjugated linoleic acids (CLAs) are a group of octadecadienoic acids (18:2) that are naturally present in food products and may have beneficial health effects. Liposomes and ethanol solutions were prepared by mixing synthetic phosphatidylcholines (PCs) with c9,t11-CLA, t10,c12-CLA, and linoleic acid (LA) in the sn-2 position into natural PCs from soybean, egg yolk, rat brain, and rat heart at 5 mol %. The oxygen diffusion-concentration products were measured using electron spin resonance spin-label oximetry methods. Individual synthetic PCs, the phospholipid matrix, and the tested lipid systems all exhibited influence on oxygen diffusion-concentration products during lipid peroxidation. Incorporating 5 mol % PC(c9,t11-CLA) into soy and egg yolk PC increased oxygen consumption in liposome suspensions while it was decreased in rat heart and brain PCs. On the other hand, PC(t10,c12-CLA) increased oxygen consumption in mixtures with egg yolk and rat heart PC but decreased it in soybean and rat brain PC. By comparison, PC(LA) decreased oxygen consumption in every case. In ethanol solutions, all of the synthetic PCs suppressed the capacity to generate peroxide radicals in the order of LA > c9,t11-CLA > t10,c12-CLA. In addition, PCs containing individual CLA isomers and LA differed in their capacities to react with and quench DPPH radicals in both ethanol solution and liposome, suggesting differences between CLA isomers and LA in DPPH radical-fatty acid interactions. Incorporation of CLA isomers and LA into dimyristyl-PC reduced the phase transition temperature from 23.6 to 23.1 and 23.3 degrees C, respectively. The results of this study provide evidence that the behavior of CLA isomers differs in the microenvironment of membranes possibly due to structural differences that affect the permeability of membranes to oxygen and lipid peroxidation.     

Free radical scavenging properties of conjugated linoleic acids.

Conjugated linoleic acids (CLA) were investigated for free radical scavenging properties against the stable 2,2-diphenyl-1-picryhydrazyl radical (DPPH.) by electron spin resonance (ESR) spectrometry and spectrophotometric methods. ESR results demonstrated that CLA directly reacted and quenched free DPPH radicals in benzene, while spectrophotometric analysis showed the radical scavenging capacity of CLA in ethanol. Dose and time effects of CLA-DPPH. reactions were observed in both tests. The ED(50) of CLA was 18 mg/mL under experimental conditions. CLA are much weaker radical scavengers as compared to vitamin E, vitamin C, and BHT. Kinetics of CLA-DPPH. reactions was different to that of linoleic acid (LA)-DPPH. reactions. CLA reacted and quenched DPPH radicals at all tested levels without a lag phase, while LA had a lag phase and showed no radical quenching activity at levels of 5-80 mg/mL in 30 min. These data indicated that CLA can provide immediate protection against free radicals, but LA cannot.     

trans-10,cis-12-conjugated linoleic acid isomer exhibits stronger oxyradical scavenging capacity than cis-9,trans-11-conjugated linoleic acid isomer

Although studies have been performed to test whether conjugated linoleic acid (CLA) acts as an antioxidant, the results were not conclusive. In addition, the CLA widely used in previous research contains 43% cis-9,trans-11 isomer, 45% trans-10,cis-12 isomer, and 10 other minor isomers. The objective of this study was to investigate the antioxidant activity of cis-9,trans-11- and trans-10, cis-12-CLA isomers using high-purity CLA isomers (>98%) by total oxyradical scavenging capacity assay (Winston, G. W.; Regoli, F.; Dugas, Jr., A. J.; Fong, J. H.; Blanchard, K. A. Free Radical Biol. Med. 1998, 24, 480-493). At all concentrations (2-200 microM), t10, c12-CLA performed as an antioxidant with a 15-min lag phase, which was more effective than c9,t11-CLA and alpha-tocopherol at lower concentrations (2 and 20 microM). On the other hand, c9,t11-CLA possessed weak antioxidant activity at 2 and 20 microM, whereas at 200 microM it acted as a strong pro-oxidant, which suggests that discrepancies of the results of the previous studies on the antioxidant properties of CLA may be due to the balance of the antioxidant properties of t10,c12-CLA and the pro-oxidant properties of c9,t11-CLA in different oxidation conditions.     

Attenuation of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced gap junctional intercellular communication (GJIC) inhibition in MCF-10A cells by c9,t11-conjugated linoleic acid

The protective effect of c9,t11-conjugated linoleic acid (CLA) on the inhibition of gap junctional intercellular communication (GJIC) was examined in a human mammary epithelial cell line (MCF-10A) treated with 12-O-tetradecanoylphorbol-13-acetate (TPA), relative to t10,c12-CLA isomer. TPA inhibited GJIC in a dose-dependent and reversible manner and was associated with connexin 43 phosphorylation. Pretreatment of 20 μM c9,t11-CLA for 24 h prior to 60 nM TPA for 1 h prevented the inhibition of GJIC by reducing the phosphorylation of connexin 43 via suppressing extracellular signal-regulated kinases (ERK1/2) activation. Reactive oxygen species (ROS) accumulation by TPA was attenuated by c9,t11-CLA. The efficacy of c9,t11-CLA in protecting inhibition of GJIC, connexin 43 phosphorylation, and ROS production was superior to that of t10,c12-CLA. These results suggest that c9,t11-CLA, including t10,c12-CLA, prevents the carcinogenesis of MCF-10A cells by protecting down-regulation of GJIC during the cancer promotion stage, and lack of their toxicities could be an excellent indicator for the chemoprevention of breast cancer.     

Conjugated linoleic acid, cis-9,trans-11, is a substrate for pulmonary 15-lipoxygenase-1 in rat

The objective of this study was to determine whether two of the major conjugated linoleic acid (CLA) isomers, cis-9,trans-11 (c9,t11) and trans-10,cis-12 (t10,c12), are possible substrates for pulmonary 15-lipoxygenase-1 (15-LOX-1) and, therefore, they are also involved in the production of 13(S)-hydroxyoctadecadienoic acid [13(S)-HODE] in biological systems. 13(S)-HODE, a major bioactive metabolite of linoleic acid, is an important intracellular signal agent and is involved in cell proliferation and differentiation in various biological systems. Nordihydroguaiaretic acid (NDGA), a known LOX inhibitor, was used as a control for measuring 15-LOX-1 enzyme activity. It was found that c9,t11-CLA was 25% as active as linoleic acid as a substrate for 15-LOX-1; however, t10,c12-CLA was not a substrate for 15-LOX-1 as measured by 13(S)-HODE production. The authenticity of the production of 13(S)-HODE from c9,t11 as a substrate was established by isolation and cochromatography with pure standard on HPLC using non-radioactive and [14C]-c9,t11-CLA.     

Preventive effect of t,t-conjugated linoleic acid on 12-O-tetradecanoylphorbol-13-acetate-induced inhibition of gap junctional intercellular communication in human mammary epithelial MCF-10A cells

The anti-tumor promotional effects of t9,t11-conjugated linoleic acid (t9,t11-CLA) and t10,t12-CLA were evaluated on the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inhibition of gap junctional intercellular communication (GJIC) in the human mammary epithelial cell line MCF-10A. The results were compared to those obtained from c9,t11-CLA, which is a more effective anti-tumor promoter on TPA-induced GJIC inhibition in MCF-10A cells than t10,c12-CLA. Cells were treated with 20 μM t9,t11-CLA, t10,t12-CLA, or c9,t11-CLA for 24 h followed by 60 nM TPA for 1 h. Both t9,t11-CLA and t10,t12-CLA equally protected MCF-10A cells from TPA-induced inhibition of GJIC with inferior efficacy to c9,t11-CLA.The protection was due to the ameliorated phosphorylation of connexin43 via suppression of extracellular signal-regulated kinases (ERK1/2) activation. Suppression of TPA-induced reactive oxygen species (ROS) generation by t9,t11-CLA and t10,t12-CLA was less effective, relative to c9,t11-CLA. The results suggest that the anti-promotional activities of t9,t11-CLA and t10,t12-CLA are equal but less potent than c9,t11-CLA in TPA-treated MCF-10A cells. The activity might be mediated by the attenuation of ROS production in MCF-10A cells by preventing the downregulation of GJIC during the cancer promotion stage.     

Preparation of a t,t conjugated linoleic acid methylester (CLA-Me) isomers mixture from synthetic CLA by methylation with BF3/methanol

Mixtures of t,t conjugated linoleic acid methylester (t,t CLA-Me) isomers were prepared from synthetic CLA, consisting of 47.8% t10,c12 CLA; 45.5% c9,t11 CLA; 2.0% t,t CLA; and 4.7% others, by methylation with BF(3)/methanol (designated TT-TC/CT) in conjunction with purification at -68 degrees C for 24 h. The amount or composition of the TT-TC/CT was greatly affected by the concentration of BF(3) in methanol and the duration of methylation. The methylation of 50 mg of synthetic CLA for 30 min with 1 mL of 7.0% BF(3)/methanol produced a TT-TC/CT (21.54 mg) with the composition of 1.3% t12,t14; 5.9% t11,t13; 42.7% t10,t12; 44.0% t9,t11; 5.0% t8,t10; and 1.1% t 7,t9 CLA, whereas the methylation for 60 min with 14.0% BF(3)/methanol produced a TT-TC/CT (28.62 mg) with the composition of t,t CLA isomers different from that of TT-TC/CT by methylation for 30 min with 7.0% BF(3)/methanol. A large quantity of TT-TC/CT (14.15 g) with the composition similar to that of TT-TC/CT prepared from 50 mg of synthetic CLA was also prepared from 25 g of synthetic CLA. The purity of TT-TC/CT samples was greater than 98%. These results suggest that TT-TC/CT with a purity greater than 98% was easily prepared from synthetic CLA by BF(3)-catalyzed methylation, and the amount and composition of t,t CLA isomers of TT-TC/CT samples could be controlled by methylation conditions.     

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.     

Total antioxidant capacity of arginine-conjugated linoleic acid (CLA) complex

Conjugated linoleic acids (CLA) have shown diverse biological activities, including anti-carcinogenic, anti-atherosclerotic, anti-adipogenic, and anti-diabetogenic effects. Recent reports also showed that CLA has free radical scavenging capacity, which may give health benefits to human beings. However, the application of CLA as a bioactive ingredient has been limited due to its insolubility in water. To overcome this problem, we investigated antioxidant activities of arginine (Arg)-CLA, a water-soluble CLA salt, using both 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assays. CLA, Arg, and Arg-CLA all exerted radical scavenging activities in a dose-dependent manner in both assays. Arg-CLA at 20 mM scavenged 89 and 55% of ABTS and DPPH radicals in 3 h, respectively, whereas CLA alone quenched only 48 and 26% of them under the same conditions. The antioxidant activity of the Arg-CLA complex was found to be synergistic in ABTS assay and comparable to that of vitamin E in DPPH assay.     

Elucidation of structural isomers from the homogeneous rhodium-catalyzed isomerization of vegetable oils

The structural isomers formed by the homogeneous rhodium-catalyzed isomerization of several vegetable oils have been elucidated. A detailed study of the isomerization of the model compound methyl linoleate has been performed to correlate the distribution of conjugated isomers, the reaction kinetics, and the mechanism of the reaction. It has been shown that [RhCl(C8H8)2]2 is a highly efficient and selective isomerization catalyst for the production of highly conjugated vegetable oils with a high conjugated linoleic acid (CLA) content, which is highly desirable in the food industry. The combined fraction of the two major CLA isomers [(9Z,11E)-CLA and (10E,12Z)-CLA] in the overall CLA mixture is in the range from 76.2% to 93.4%. The high efficiency and selectivity of this isomerization method along with the straightforward purification process render this approach highly promising for the preparation of conjugated oils and CLA. Proposed improvements in catalyst recovery and reusability will only make this method more appealing to the food, paint, coating, and polymer industries in the future.     

Free radical scavenging properties of wheat extracts

Three hard winter wheat varieties (Akron, Trego, and Platte) were examined and compared for their free radical scavenging properties and total phenolic contents (TPC). Free radical scavenging properties of wheat grain extracts were evaluated by spectrophotometric and electron spin resonance (ESR) spectrometry methods against stable 2,2-diphenyl-1-picryhydrazyl radical (DPPH*) and radical cation ABTS*+ (2,2'-azino-di[3-ethylbenzthiazoline sulfonate]). The results showed that the three wheat extracts differed in their capacities to quench or inhibit DPPH* and ABTS*+. Akron showed the greatest activity to quench DPPH radicals, while Platte had the highest capacity against ABTS*+. The ED50 values of wheat extracts against DPPH radicals were 0.60 mg/mL for Akron, 7.1 mg/mL for Trego, and 0.95 mg/mL for Platte under the experimental conditions. The trolox equivalents against ABTS*+ were 1.31 +/- 0.44, 1.08 +/- 0.05, and 1.91 +/- 0.06 micromol/g of grain for Akron, Trego, and Platte wheat, respectively. ESR results confirmed that wheat extracts directly reacted with and quenched free radicals. The TPC were 487.9 +/- 927.8 microg gallic acid equivalents/g of grain. No correlation was observed between TPC and radical scavenging capacities for DPPH* and ABTS*+ (p = 0.15 and p > 0.5, respectively).     

Isomeric distribution of conjugated linoleic acids (CLA) in the tissues of layer hens fed a CLA diet

The isomeric distribution of conjugated linoleic acids (CLA) in the tissue lipids of hens in relation to that in the diet was examined. Silver-ion high-performance liquid chromatography was used to quantify individual CLA isomers in total tissue lipids, phospholipids, and triacylglycerols. It was found that the deposition of CLA isomers in hen tissues was selective. All tissues including serum, liver, heart, kidney, abdominal fat, and leg and breast muscles had lesser amounts of total cis/trans isomers ranging from 75.87 to 89.13% of total CLA, which was in contrast to the value of 92% of total CLA in the dietary lipids. Total trans/trans isomers in all tissue lipids ranging from 6.11 to 18.02% of total CLA were greater than that in the diet (4.19%). Among the individual trans/trans isomers, all tissues except for adipose tissue and brain incorporated greater amounts of t-12,t-14-18:2, t-11,t-13-18:2,t-10,t-12-18:2, t-9,t-11-18:2, and t-18,t-10-18:2 compared with the values of the diet. Within the cis/trans group, lesser amounts of c-10,t-12/t-10,c-12-18:2 were found to incorporate into all tissues compared with the value of the diet. Serum and liver had higher percentages of c-9,t-11/t-9,c-11, whereas the other tissues had similar levels of this isomer compared with that of the diet. It was also observed that supplementation of CLA in the diet of layer hens decreased the concentration of docosahexaenoic acid (22:6n-3) in all of the tissue lipids. It is concluded that dietary CLA can transfer to the tissue but that incorporation of CLA isomers into the tissue is selective in hens.     

Determination of the conjugated linoleic acids in cow's milk fat by Fourier transform Raman spectroscopy

The collective term "conjugated linoleic acid" or "CLA" generally refers to a mixture of conjugated positional and geometric isomers of linoleic (cis-9,cis-12-octodecadienoic) acid. In nature, these isomers are mainly formed in the rumen by biohydrogenation of polyunsaturated fatty acids. This study concerns a first trial of CLA determination in cow's milk fat by Raman spectroscopy. The spectra of pure cis-9-oleic, cis-9,cis-12-linoleic, cis-9,trans-11-linoleic, and trans-10,cis-12-linoleic acids have been examined in comparison with the spectra of selected milk-fat samples containing between 0 and 3% of CLA. The trial of CLA determination by Raman spectroscopy on cow milk fat has reached its objective with the two following results. First, the examination of the Raman spectra allows to identify three specific Raman signals of the chemical bonds associated to the cis,trans conjugated C=C in the rumenic and trans-10,cis-12-octodecadienoic acids at 1652, 1438, and 3006 cm(-1). Second, the calibration of Raman spectrometer for the CLA determination has indicated that these three specific signals suit very well for the accurate and reliable measurement of CLA concentration in milk fat. To our knowledge, the present study is the first successful attempt to determine the CLA content of milk fat by a spectrophotometric method.     

Effect of diet and dietary fatty acids on the transformation and incorporation of C18 fatty acids in double-muscled Belgian Blue young bulls

Three groups of double-muscled Belgian Blue young bulls were fed during different stages of production diets differing in the proportions of linolenic and linoleic acid by including linseed in the concentrate or giving grass silage as main linolenic acid suppliers. Samples of rumen and abomasal contents and of the longissimus thoracis, subcutaneous fat, and liver were taken to analyze the fatty acid pattern with emphasis on the individual trans (t) C18:1 fatty acids and cis-9,trans-11 conjugated linoleic acid (c9t11CLA). Trans C18:1 isomers represented up to 20 g/100 g of total fatty acids in rumen and abomasal contents, whereas the accumulation of c9t11CLA was limited. Total trans C18:1 content in subcutaneous fat and intramuscular fat of the longissimus thoracis comprised 8.4 and 5.2 g/100 g of total fatty acids, respectively, with t11C18:1 being the most abundant one. Compared to rumen contents, subcutaneous and intramuscular fat were enriched in c9t11CLA and contained fewer tC18:1 isomers, resulting in a higher c9t11CLA/t11C18:1 ratio (0.04, 0.22, and 0.22, respectively). This result suggests that the endogenous synthesis of c9t11CLA in adipose tissue by the Delta(9)-desaturase was more important than its ruminal production.     

A mixture of trans, trans conjugated linoleic acid induces apoptosis in MCF-7 human breast cancer cells with reciprocal expression of Bax and Bcl-2

The growth inhibitory effect of a mixture of trans, trans conjugated linoleic acid isomers (t, t CLA) was investigated in a human breast cancer cell line, MCF-7, with references to c9, t11 CLA, t10, c12 CLA, and linoleic acid. The t, t CLA treatment effectively induced a cytotoxic effect in a time-dependent (0-6 days) and concentration-dependent (0-40 microM) manner, as compared to the reference and control treatments. The apoptotic parameters were measured on cells treated with 40 microM t, t CLA for 4 days. The occurrence of the characteristic morphological changes and DNA fragmentation confirmed apoptosis. The t, t CLA treatment led to an increase in the level of p53 tumor suppressor protein and Bax protein, but suppressed the expression of Bcl-2 protein. In addition, cytochrome c was released from the mitochondria into the cytosol, and the activation of caspase-3 led to the cleavage of poly(ADP-ribose) polymerase (PARP). Moreover, the composition of the linoleic and arachidonic acids was decreased in cellular membranes. These findings suggest that incorporation of t, t CLA in the membrane induces a mitochondria-mediated apoptosis that can enhance the antiproliferative effect of t, t CLA in MCF-7 cells.     

Production of silkworms with conjugated linoleic acid (CLA) incorporated into their lipids by dietary CLA

Silkworms with conjugated linoleic acid (CLA) incorporated into their lipids (designated CLA silkworms) were produced to enhance the quality of silkworms having a synergistic effect with CLA functions by dietary synthetic CLA. Silkworm larvae were fed fresh mulberry leaves (control diet) until the third instar stage and were then subjected to various levels (0%, 0.1%, 1%, 5%, and 10%) of CLA-sprayed mulberry leaves (designated CLA diet) beginning on the first day of the fourth instar stage and continuing to the third day of the fifth instar stage. CLA contents in CLA silkworms increased proportionally with increasing CLA levels of CLA diets. CLA silkworms on a 1% CLA diet contained 2.2 g CLA/100 g lipid without body weight reduction, whereas CLA silkworms on a 10% CLA diet contained 14.8 g CLA/100 g lipid with a significant reduction of body weight, relative to the control silkworms. The CLA content in the lipids of CLA silkworms on a 10% CLA diet was significantly higher than that of CLA silkworms on a 5% CLA diet. A 0.1% CLA diet was not sufficient to accumulate CLA in the silkworms. Most of the CLA (approximately 99%) of silkworm lipids was present in triglyceride (TG) with a similar ratio of c9,t11 and t10,c12 CLA isomers. These results suggest that a 1% CLA diet was suitable for the production of CLA silkworms.     

Green tea polyphenols react with 1,1-diphenyl-2-picrylhydrazyl free radicals in the bilayer of liposomes: direct evidence from electron spin resonance studies

Free radical scavenging reactions of green tea polyphenols (GTP) were investigated with electron spin resonance (ESR) spectroscopy in the phospholipid bilayer of liposomes, using 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical as a model. The results showed that (1) GTP reacts with DPPH radicals in the bilayer of liposomes of both 1-hexadecanoyl-2-[(cis,cis,cis,cis,cis,cis)-4,7,10, 13,16,19-docosahexaenoyl]-sn-glycero-3-phosphocholine (DHAPC) and 1, 2-di[cis-9-hexadecenoyl]-sn-glycero-3-phosphocholine) (DPPC); and (2) GTP protects DHAPC liposomes effectively from the oxidation initiated by DPPH radicals. These results provide direct evidence that GTP reacts with free radicals in the model membrane and support the hypothesis that GTP protects unsaturated phospholipids from oxidation by reacting directly with the radicals.     

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.     

Free radical scavenging activity of chitooligosaccharides by electron spin resonance spectrometry

The radical scavenging effects of chitooligosaccharides (COSs) on hydroxyl radical, superoxide radical, alkyl radical, and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were investigated using a spin-trapping electron spin resonance (ESR) method and compared with the ESR signal intensity. COSs exhibited strong scavenging activity on hydroxyl radical and superoxide radical and weak scavenging activity on alkyl radical and DPPH radical. The radical scavenging activity of COSs increased with increment of concentration, and it was also dependent on molecular weight. These results suggest that the scavenging activity of COSs is dependent on their molecular weights and tested radicals.     

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.