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PubMed2001

Conjugated linoleic acid: a review.

Conjugated linoleic acid (CLA) refers to a group of positional and geometric isomers of the omega-6 essential fatty acid linoleic acid (cis-9, cis-12, octadecadienoic acid). In humans evidence is currently ambiguous as to whether CLA supplementation has a significant effect on body composition. Despite favorable changes in lipid levels in animal models, a beneficial effect in humans has not yet been established. While some of the changes reported are consistent with an improved lipid profile, declines in HDL and increases in lipoprotein (a) have also been observed in some subjects. Available evidence suggests CLA supplementation has no impact on immune system performance in healthy subjects.

Animals↗
PubMed1997

Effect of feeding on conjugated cis delta 9, trans delta 11-octadecadienoic acid and other isomers of linoleic acid in bovine milk fats.

Almost 2000 bovine milk fats were analysed by gas chromatography to investigate the influence of typical barn and pasture feeding of cows on trans-C18:2 isomers (with at least one trans double bond) including the conjugated linoleic acid cis delta9, trans delta11 (c9,t11) as well as the cis delta9, cis delta12 linoleic acid. Moreover, small cow herds were used to determine the influence of pasture Feeding with young and older grass as well as the impact of an energy deficit or the variation of quantity and technical treatment of fed rape-seed on the content of C18:2 isomers in milk fat. The contents of trans-C18:2 (w/o c9,t11) and c9,t11 in 1756 milk fats on average amounted to 0.63% resp. 0.75%. These contents increased from barn feeding, in winter with 0.46% resp. 0.45% over the transiton period in spring and late autumn with 0.66% resp. 0.76% to pasture feeding in summer with 0.87% resp. 1.20%. Milk fat samples from bulk milk obtained weekly during one year from 4 large West German milk collection areas confirmed and completed the data found for the 1756 milk fats. The percentage of linoleic acid with a mean value of 1.24 (n = 1756) varied irregularly during the different feeding periods. The content of the conjugated linoleic acid c9,t11 could be raised considerably up to triple the normal amount by different changes in feeding. However, the content of trans-C18:1 fatty acids was strongly increased as well, respectively.

Animals↗
PubMed1999

Bile diversion in rats leads to a decreased plasma concentration of linoleic acid which is not due to decreased net intestinal absorption of dietary linoleic acid.

Decreased bile secretion into the intestine has been associated with low plasma concentrations of essential fatty acids (EFA) in humans. We studied the mechanism behind this relationship by determining the status and absorption of the major dietary EFA, linoleic acid (LA), in control and 1-week bile-diverted rats. The absorption of LA was quantified by a balance method and by measuring plasma concentrations of [13C]LA after its intraduodenal administration. Absolute and relative concentrations of LA in plasma were decreased in bile-diverted rats (P<0.01 and P<0.001, respectively). Fecal excretion of LA was increased at least 20-fold in bile-diverted rats (0.72+/-0.11 vs. 0.03+/-0.00 mmol/day; P<0.0001). Due to increased chow ingestion by bile-diverted rats, net intestinal absorption of LA was similar between bile-diverted and control rats (1.96+/-0.14 vs. 1.91+/-0.07 mmol/day, respectively; P>0.05). After intraduodenal administration of [13C]LA, plasma concentrations were approximately 3-4-fold lower in bile-diverted rats for at least 6 h (P<0.001). Plasma concentrations of both [12C]arachidonic acid and [13C]arachidonic acid were increased in bile-diverted rats (P<0.05). We conclude that decreased plasma concentrations of LA in 1-week bile-diverted rats are not due to decreased net intestinal absorption of LA, but may be related to increased metabolism of LA.

Animals↗
PubMedDate not supplied

[Characteristics of the aggregative state of the substrate in the reaction of 5-lipoxygenase oxidation of linoleic acid].

5-lipoxygenase (EC 1.13.11.12) oxidizes polyunsaturated fatty acids by molecular oxygen. The enzyme acts in close contact with the cell membranes, which main components are ionic and non-ionic lipids. In order to investigate the kinetic parameters of 5-lipoxygenase reaction in vitro, extremely hydrophobic fatty acid substrate (linoleic acid) should be solubilized in the reaction mixture. We used Lubrol PX ("Sigma" Chem. Co), as a non-ionic detergent consisted of oligoethylene glycol and fatty alcohol. Linoleic acid and Lubrol PX formed mixed micelles thus solubilizing the fatty acid substrate in a buffer with appropriate pH. We have studied the sizes and shapes of mixed micelles Lubrol PX/linoleic acid (aggregates type 1) and Lubrol PX/linoleic acid/SDS (aggregates type 2; SDS was an effective activator of potato tuber 5-lipoxygenase) by means of gel-filtration and laser light scattering techniques. The parameters under investigation were molecular weights, Stocks radii and shapes of the mixed micelles. The average molecular weights and Stocks radii of the mixed micelles type 1 determined by mean of gel-filtration on Sephadex G-200 were 95,142 +/- 5184 Da and 3.45 +/- 0.11 nm, respectively. The same parameters for the mixed micelles type 2 were 73,694 +/- 893 Da and 3.02 +/- 0.02 nm, respectively. The strong similarity in physicochemical parameters for both types of mixed micelles indicated that SDS did not influence the size and shape of mixed micelles of Lubrol PX and linoleic acid. The activatory action of SDS on potato tuber lipoxygenase may be a result of electrostatic effect or direct participation of SDS in enzymatic catalysis. The laser light scattering technique allowed to determine two main fraction of particles in type 1 system with hydrodynamic diameters 2.6 and 5.7 nm and relative contribution to light scattering 13 and 87%, respectively. The particles with d = 5.7 nm were interpreted as the mixed micelles. The particles with d = 2.6 nm were interpreted as isolated molecules of Lubrol PX, linoleic acid and (or) their premicellar aggregates. The data obtained are to be used in creation of reliable physical and mathematical models of 5-lipoxygenase.

Arachidonate 5-Lipoxygenase↗
PubMed2005

Maternal dietary Alpine butter intake affects human milk: fatty acids and conjugated linoleic acid isomers.

Consumption of CLA by lactating women affects the composition of their milk, but the pattern of the different CLA isomers is still unknown. We determined the effects of short maternal supplementation with CLA-rich Alpine butter on the occurrence of FA and CLA isomers in human milk. In an open randomized controlled study with a two-period cross-over design, milk FA and CLA isomer concentrations were measured on postpartum days > or = 20 in two parallel groups of lactating women before, during, and after consumption of defined quantities of Alpine butter or margarine with comparable fat content (10 d of butter followed by 10 d of margarine for one group, and vice versa in the other). In the 16 women who completed the study (8/group), Alpine butter supplementation increased the C16 and C18 FA, the sum of saturated FA, the 18:1 trans FA, and the trans FA with CLA. The CLA isomer 18:2 c9,t11 increased by 49.7%. Significant increases were also found for the isomers t9,t11, t7,c9, t11,c13, and t8,c10 18:2. The remaining nine of the total 14 detectable isomers showed no changes, and concentrations were <5 mg/100 g fat. A breastfeeding mother can therefore modulate the FA/CLA supply of her child by consuming Alpine butter. Further studies will show whether human milk containing this FA and CLA isomer pattern acts as a functional food for newborns.

Adult↗
PubMed2005

Distribution of polyunsaturated fatty acids including conjugated linoleic acids in total and subcellular fractions from healthy and cancerous parts of human kidneys.

Differences in the FA composition of subcellular fractions from healthy and cancerous kidney tissues from the same patients were examined. Only minor differences in CLA content were found between the healthy and the cancerous tissue portions. Regarding the distribution pattern, CLA incorporation into nuclei and cytosol was significantly higher than incorporation into plasma membranes and mitochondria, which could be correlated to the neutral lipid content of these fractions. The subcellular distribution pattern of CLA was similar to that observed with monounsaturated FA but unlike that found with 18:2n-6, which underlines the different physiological properties of CLA and 18:2n-6. Because PUFA have been suggested to have an effect on cancer risk, the contents of n-3 and n-6 PUFA were determined in kidney and renal cell carcinoma (RCC). The 18:2n-6 content and delta5 desaturase activity were significantly lower, and the 18:3n-6, 20:3n-6, and 20:5n-3 contents and delta6 desaturase activity were significantly higher in RCC than in healthy renal tissue, indicating a changed PUFA metabolism in RCC. Previous research has suggested that CLA inhibits the elongation and desaturation of 18:2n-6 into 20:4n-6. In that case, one might speculate that a diet enriched in CLA would be a useful tool in preventing RCC. However, the involvement of CLA in preventing renal cancer could not be demonstrated definitively from the design of this experiment. Further understanding of the cause and/or consequence of the difference in FA metabolism may lead to a better understanding of RCC.

Fatty Acids, Unsaturated↗
PubMed1988

Linoleic acid requirement of rats fed trans fatty acids.

The amount of linoleic acid required to prevent undesirable effects of C18 trans fatty acids was investigated. In a first experiment, six groups of rats were fed diets with a high content of trans fatty acids (20% of energy [en%]), and increasing amounts of linoleic acid (0.4 to 7.1 en%). In a second experiment, four groups of rats were fed diets designed to compare trans fatty acids with saturated and cis-monounsaturated fatty acids of the same chain length at the 2 en% linoleic acid level. After 9-14 weeks, the oxygen uptake, lipid composition and ATP synthesis of heart and liver mitochondria were determined. The phospholipid composition of the mitochondria did not change, but the fatty acid compositions of the two main mitochondrial phospholipids were influenced by the dietary fats. Trans fatty acids were incorporated in all phospholipids investigated. The linoleic acid level in the phospholipids, irrespective of the dietary content of linoleic acid, increased on incorporation of trans fatty acids. The arachidonic acid level had decreased in most phospholipids in animals fed diets containing 2 en% linoleic acid. At higher linoleic acid intakes, the effect of trans fatty acids on the phospholipid arachidonic acid level diminished. However, in heart mitochondrial phosphatidylethanolamine, trans fatty acids significantly increased the arachidonic acid level. Despite these changes in composition, neither the amount of dietary linoleic acid nor the addition of trans fatty acids influenced the mitochondrial function. For rats, a level of 2 en% of linoleic acid is sufficient to prevent undesirable effects of high amounts of dietary C18 trans fatty acids on the mitochondrial function.

Animals↗
PubMed2000

An isomeric mixture of conjugated linoleic acids but not pure cis-9, trans-11-octadecadienoic acid affects body weight gain and plasma lipids in hamsters.

We report the effect of an atherogenic diet supplemented with cis-9, trans-11-octadecadienoic acid (c9t11), linoleic acid (LA) or an isomeric mixture of conjugated linoleic acids (CLA) on plasma lipids, weight gain and food intake of male Golden Syrian hamsters. Animals were assigned to three diet groups (n = 10), and fed nonpurified diet, supplemented with 10% hydrogenated coconut oil and 0.05% cholesterol for 6 wk. The first diet group was further supplemented with 1% CLA (CLA group), the second diet group with 0.2% c9t11 (c9t11 group) and the third group with 0.2% LA (LA group). The diets were designed to have equivalent levels of c9t11 in the CLA and c9t11 groups. At 2 and 6 wk of feeding, the CLA group had significantly lower plasma triglyceride and total cholesterol concentrations than either the c9t11 or the LA groups. HDL-cholesterol did not differ among diet groups. The CLA group had significantly lower weight gain but greater food intake than either the c9t11 or the LA groups. There were no significant differences between the c9t11 and the LA groups in any of the variables measured. We conclude that under our experimental conditions of short-term feeding, c9t11, thought to be the active compound in CLA, does not produce the same effect as the isomer mixture.

Analysis of Variance↗
PubMed2002

Trans-10,cis-12 conjugated linoleic acid suppresses the desaturation of linoleic and alpha-linolenic acids in HepG2 cells.

The objective of this study was to determine the effects of cis-9,trans-11 and trans-10,cis-12 CLA on the fatty acid desaturation in a human hepatoma cell line, HepG2. Therefore, experiments were conducted in which HepG2 cells were incubated with various concentrations of those fatty acids and the concentrations of fatty acids in various lipid fractions of HepG2 cells were determined. In the presence of linoleic acid as substrate, cells treated with 25 micromol/L of trans-10,cis-12 CLA had lower ratios of dihomo-gamma-linoleic acid to linoleic acid and of arachidonic acid to linoleic acid in phospholipids than control cells; with alpha-linolenic acid as substrate, they had a lower ratio of eicosapentaenoic acid to alpha-linolenic acid in phospholipids than control cells. Cells treated with cis-9,trans-11 CLA did not differ in these ratios from control cells. Cells treated with trans-10,cis-12 CLA had also a markedly lower ratio of monounsaturated fatty acids (MUFA) to saturated fatty acids (SFA) in lipids than control cells; cells treated with cis-9,trans-11 CLA had a slightly lower MUFA:SFA ratio than control cells. These findings suggest that trans-10,cis-12 CLA suppresses Delta9-, Delta6- and Delta5-desaturation in HepG2 cells; cis-9,trans-11 CLA slightly reduces Delta9-desaturation but does not inhibit Delta6- and Delta5-desaturation. Moreover, HepG2 cells treated with 100 micromol/L of trans-10,cis-12 CLA released larger amounts of 6-keto-prostaglandin F(1alpha) and prostaglandin F(2alpha) than control cells. Treatment of cells with cis-9,trans-11 CLA did not alter the release of these eicosanoids compared with control cells. In conclusion, this study suggests that trans-10,cis-12 CLA has significant effects on the metabolism of essential fatty acids in HepG2 cells, whereas cis-9, trans-11 CLA does not have any effect in this respect.

Eicosanoids↗
PubMed2005

Lipid class distribution of fatty acids including conjugated linoleic acids in healthy and cancerous parts of human kidneys.

In this study the FA compositions of healthy and cancerous human renal tissues from the same patients are compared with special reference to the CLA and PUFA content. CLA was preferentially incorporated into neutral lipid compared with phospholipid classes. Its distribution profile was similar to that of monounsaturated FA, but unlike that found with 18:2n-6. Different incorporation patterns were found for individual CLA isomers. Comparing renal cell carcinoma (RCC) and healthy kidney, the total CLA content was significantly lower in the cholesterylester fraction and significantly higher in the PE and PS fractions from RCC. The most significant differences between healthy and cancerous renal tissue were in the content of t10,c12-CLA. Furthermore, the lipid class distributions of n-6 PUFA were determined, and several significant differences between RCC and healthy renal tissue were found. This is of interest, as it has been proposed that the anticarcinogenic properties of dietary CLA are associated with their interference in the metabolism of 20:4n-6. The involvement of CLA in preventing renal cancer cannot be definitively demonstrated from the design of this study, nor was it intended, but the complete determination of the FA composition of adjacent healthy and cancerous tissues may provide an insight if lipids are involved in this disease.

Aged↗
PubMed2002

Purification of lipoxygenase from Chlorella: production of 9- and 13-hydroperoxide derivatives of linoleic acid.

Oxygenation of linoleic acid by the enzyme lipoxygenase (LOX) that is present in the microalga Chlorella pyrenoidosa is known to produce the corresponding 9- and 13-hydroperoxide derivatives of linoleic acid (9- and 13-HPOD, respectively). Previous work with this microalga indicated that partially purified LOX, present in the 30-45 and 45-80% saturated (NH4)2SO4 precipitate fractions, produced both HPOD isomers but in different ratios. It was not clear, however, if the observed activity in the two isolates represented the presence of one or more isozymes. In the present work, LOX isolated from the intracellular fraction of Chlorella by (NH4)2SO4 precipitation (35-80% saturated) was purified by ion exchange and hydrophobic interaction chromatography to apparent homogeneity. Analysis of the purified protein by SDS-PAGE and subsequent native size exclusion chromatography demonstrated that LOX in Chlorella is a single monomeric protein with a molecular mass of approximately 47 kDa. The purified LOX produced both the 9-HPOD and 13-HPOD isomers from linoleic acid in equal amounts, and the isomer ratio was not altered over the pH range of 6 to 9. Optimal activity of LOX was at pH 7.5.

Chlorella↗
PubMed2002

Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide.

A reaction of 13-hydroperoxide octadecadienoic acid (13-HPODE) with cytochrome c was analysed using ESR, HPLC-ESR and HPLC-ESR-MS by the combined use of the spin-trapping technique. The ESR, HPLC-ESR and HPLC-ESR-MS analyses showed that cytochrome c catalyses formation of pentyl and octanoic acid radicals from 13-HPODE. On the other hand, only the alpha-(4-pyridyl-1-oxide)-N-t-butylnitrone/octanoic acid radical adduct was detected in the elution profile of HPLC-ESR for a mixture of 13-HPODE with haematin, indicating that haematin catalyses the formation of octanoic acid radical. In addition, the reaction of 13-HPODE with cytochrome c was inhibited by chlorogenic acid, caffeic acid and ferulic acid via two possible mechanisms, i.e. reducing cytochrome c (chlorogenic acid and caffeic acid) and scavenging the radical intermediates (chlorogenic acid, caffeic acid and ferulic acid).

Animals↗
PubMed2006

Micellar oleic and eicosapentaenoic acid but not linoleic acid influences the beta-carotene uptake and its cleavage into retinol in rats.

Improving the bioavailability of beta-carotene is vital to manage vitamin A deficiency. The influence of micellar oleic (OA), linoleic (LA) and eicosapentaenoic (EPA) acids on plasma beta-carotene response and its conversion to retinol has been studied in rats employing single (9 h time course) and repeated (10 days) dose administrations. After a single dose, the levels (area under the curve) of plasma beta-carotene and retinyl palmitate in OA and EPA groups were higher (p < 0.05) by 13, 7 and 11, 6 folds than LA group. The liver beta-carotene level in OA and EPA groups were higher (p < 0.05) by 3 and 1.2 folds than LA group. After repeated dose, the plasma beta-carotene and retinyl palmitate levels in OA (6.2%, 51.7%) and EPA (25.4%, 17.23%) groups were higher (p < 0.05) than LA group. The liver beta-carotene level in OA (21.2%) and EPA (17.6%) groups were higher (p < 0.05) than LA group. In both the experiments, the activity of beta-carotene 15,15'-dioxygenase in the intestinal mucosa and plasma triglyceride levels were also higher in OA and EPA groups than LA group. beta-Carotene excreted through urine and feces of OA and EPA groups was lower than the LA group. These results demonstrate an improved absorption and metabolism of beta-carotene when fed mixed micelles with OA or EPA compared with LA. Although the mechanism involved in selective absorption of fatty acids needs further studies, intestinal beta-carotene uptake and its conversion to vitamin A can be modulated using specific fatty acids.

Animals↗