Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “LINOLEIC ACID”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 1,099 records · Page 61Linked to original sources
PubMedDate not supplied

Methods for analysis of conjugated linoleic acids and trans-18:1 isomers in dairy fats by using a combination of gas chromatography, silver-ion thin-layer chromatography/gas chromatography, and silver-ion liquid chromatography.

Conjugated linoleic acids (CLA) are octadecadienoic acids (18:2) that have a conjugated double-bond system. Interest in these compounds has expanded since CLA were found to be associated with a number of physiological and pathological responses such as cancer, metastases, atherosclerosis, diabetes, immunity, and body fat/protein composition. The main sources of these conjugated fatty acids are dairy fats. Rumen bacteria convert polyunsaturated fatty acids, especially linoleic and linolenic acids, to CLA and numerous trans- containing mono- and diunsaturated fatty acids. It has been established that an additional route of CLA synthesis in ruminants and monogastric animals, including humans, occurs via delta9 desaturation of the trans-18:1 isomers. To date, a total of 6 positional CLA isomers have been found in dairy fats, each occurring in 4 geometric forms (cis,trans; trans,cis; cis,cis; and trans,trans) for a total of 24. All of these CLA isomers can be resolved only by a combination of gas chromatography (GC), using 100 m highly polar capillary columns, and silver-ion liquid chromatography, using 3 of these 25 cm columns in series. Complete analysis of all the trans-18:1 isomers requires prior isolation of trans monoenes by silver-ion thin-layer chromatography (TLC), followed by GC analysis using the same 100 m capillary columns operated at low temperatures starting from 120 degrees C. These analytical techniques are required to assess the purity of commercial CLA preparations, because their purity will affect the interpretation of any physiological and/or biochemical response obtained. Prior assessment of CLA preparations by TLC is also recommended to determine the presence of any other impurities. The availability of pure CLA isomers will permit the evaluation and analysis of individual CLA isomers for their nutritional and biological activity in model systems, animals, and humans. These techniques are also essential to evaluate dairy fats for their content of specific CLA isomers and to help design experimental diets to increase the level of the desired CLA isomers in dairy fats. These improved techniques are further required to evaluate the CLA profile in monogastric animals fed commercial CLA preparations for CLA enrichment of animal products. This is particularly important because absorption and metabolism will alter the ingested-CLA profile in the animal fed.

Animals↗
PubMed2004

Decreased aortic early atherosclerosis and associated risk factors in hypercholesterolemic hamsters fed a high- or mid-oleic acid oil compared to a high-linoleic acid oil.

Currently, diets higher in polyunsaturated fat are believed to lower blood cholesterol concentrations, and thus reduce atherosclerosis, greater than diets containing high amounts of saturated or possibly even monounsaturated fat. The present study was designed to investigate the effect of diets containing mid- or high-linoleic oil versus the typical high-linoleic sunflower oil on LDL oxidation and the development of early atherosclerosis in a hypercholesterolemic hamster model. Animals were fed a hypercholesterolemic diet containing 10% mid-oleic sunflower oil, high-oleic olive oil, or high-linoleic sunflower oil (wt/wt) plus 0.4% cholesterol (wt/wt) for 10 weeks. After 10 weeks of dietary treatment, only the animals fed the mid-oleic sunflower oil had significant reductions in plasma LDL-C levels (-17%) compared to the high-linoleic sunflower oil group. The high-oleic olive oil-fed hamsters had significantly higher plasma triglyceride levels (+41%) compared to the high-linoleic sunflower oil-fed hamsters. The tocopherol levels in plasma LDL were significantly higher in hamsters fed the mid-oleic sunflower oil (+77%) compared to hamsters fed either the high-linoleic sunflower or high-oleic olive oil. Measurements of LDL oxidation parameters, indicated that hamsters fed the mid-oleic sunflower oil and high-oleic olive oil diets had significantly longer lag phase (+66% and +145%, respectively) and significantly lower propagation rates (-26% and -44%, respectively) and conjugated dienes formed (-17% and -25%, respectively) compared to the hamsters fed the high-linoleic sunflower oil. Relative to the high-linoleic sunflower oil, aortic cholesterol ester was reduced by -14% and -34% in the mid-oleic sunflower oil and high-oleic olive oil groups, respectively, with the latter reaching statistical significance. Although there were no significant associations between plasma lipids and lipoprotein cholesterol with aortic total cholesterol and cholesterol esters for any of the groups, the lag phase of conjugated diene formation was inversely associated with both aortic total and esterified cholesterol in the high-oleic olive oil-fed hamsters (r = -0.69, P < 0.05). The present study suggests that mid-oleic sunflower oil reduces risk factors such as lipoprotein cholesterol and oxidative stress associated with early atherosclerosis greater than the typical high-linoleic sunflower oil in hypercholesterolemic hamsters. The high-oleic olive oil not only significantly reduced oxidative stress but also reduced aortic cholesterol ester, a hallmark of early aortic atherosclerosis greater than the typical high-linoleic sunflower oil.

Animals↗
PubMed1990

Epidermal growth factor stimulates linoleic acid metabolism in BALB/c 3T3 fibroblasts.

One response of BALB/c 3T3 cells to epidermal growth factor (EGF) is the release and subsequent metabolism of arachidonic acid. Prostaglandins generated from EGF treatment appear to play a role in the mitogenic signal. Lipoxygenase inhibitors (nordihydroguaiaretic acid and 5,8,11,14-eicosatetraynoic acid) were previously shown to be very effective in blocking EGF-stimulated DNA synthesis; however, only low levels of lipoxygenase-derived arachidonate metabolites were detected. In an extension of these investigations, we have now found that EGF stimulates lipoxygenase metabolites of linoleic acid in BALB/c 3T3 fibroblasts. In the presence of EGF (10 ng/ml), the cells converted 10-15% of exogenous linoleic acid (10 microM) to hydroxy fatty acids that were isolated on reverse phase high performance liquid chromatography. No linoleate metabolites were detected in the absence of EGF. The isolated compounds were characterized further by straight phase high performance liquid chromatography, UV spectroscopy, and gas chromatography-mass spectrometry analyses, and they were identified as 13-hydroxyoctadecadienoic acid and 9-hydroxyoctadecadienoic acid. The hydroxy metabolites and their hydroperoxy precursors produced a 2- to 4-fold potentiation of EGF-stimulated [3H]thymidine incorporation in BALB/c 3T3 cells. These linoleate derivatives stimulated DNA synthesis at concentration ranges of 10(-8) to 10(-6) M. Thus, linoleic acid metabolism might be an important element in the EGF-regulated cascade of biochemical events leading to fibroblast mitogenesis.

Animals↗
PubMed1988

Effects of dietary linoleic acid on beta-adrenergic responsiveness of the guinea pig respiratory system.

Respiratory autonomic beta-adrenergic receptor function was investigated in isolated tracheal spirals of guinea pigs receiving different diets. Comparison was made between control and Haemophilus influenzae treated animals; this latter group serving as animal model for atopy. The different semi-synthetic diets (35 energy%) varying in their linoleic acid contents (5.85, 11.25 and 22.05 en%), exerted profound effects on membrane fatty acid composition. No influence of these diets on either food intake or growth could be detected. Isoprenaline induced relaxation of guinea pig tracheal spirals was maximal in the dietary group receiving moderate linoleic acid (11.25 en%). Both the addition and the withdrawal of linoleic acid to this diet resulted in a significant impairment of beta-adrenergic receptor function, to the same extent as can be induced by Haemophilus influenzae. The results are discussed in view of current concepts for atopy.

Animals↗
PubMed1998

Linoleic acid and tumor necrosis factor-alpha increase manganese superoxide dismutase activity in intestinal cells.

Manganese superoxide dismutase (MnSOD) protects mitochondria from oxidative damage. Alterations in the regulation of MnSOD plays an important role in the development of many types of cancer. Activity of this enzyme is induced by inflammatory cytokines and other conditions that increase oxygen radical production. High levels of dietary lipid have been shown to decrease MnSOD activity. This study was designed to define the effect of various type of fatty acids on MnSOD activity and MnSOD induction. IEC-6 cells were treated with 40 micromol/l of either linoleic acid (LA), eicosapentaenoic acid (EPA), or oleic acid (OA) in the presence or absence of 10 ng/ml tumor necrosis factor-alpha (TNF-alpha). Fatty acid supplementation increased MnSOD activity. MnSOD activity was greater in the LA group than in the EPA or OA groups. TNF-alpha induced MnSOD activity equally in all fatty acid-supplemented groups. High levels of MnSOD activity may be an indicator of chronic inflammation resulting from fatty acid, particularly LA, supplementation.

Animals↗
PubMed1996

The relationships between dietary alpha-linolenic:linoleic acid and rat platelet eicosapentaenoic and arachidonic acids.

Increased dietary intake of alpha-linolenic acid (ALA) may be desirable to enrich tissue eicosapentaenoic acid (EPA; 20:5n-3) but competition between n-3 and n-6 fatty acids for enzymes involved in elongation and subsequent acylation will determine the relative proportions of phospholipid fatty acids. The aim of the present study was to examine the effects of altering the dietary ALA:linoleic acid (LA) ratio on rat platelet EPA and arachidonic acid (AA; 20:4n-6) concentrations. Sprague-Dawley rats were fed on diets containing 30% total energy as fat with approximately 10% each of saturated, monounsaturated and polyunsaturated fatty acids with one of the following ALA:LA values; 1:7, 1:4, 1:1 or 1.3:1 (nine rats per group). After 4 weeks, blood was withdrawn from the abdominal aorta and platelet fatty acids analysed. The proportion of EPA was greater at the 1:1 and 1.3:1 ratios compared with the 1:7 and 1:4 (P < 0.05), and a decrease in AA was observed (P < 0.05) at the higher ratios. It was established that the platelet EPA:AA value increased (P < 0.05) as the dietary ALA:LA value increased.

Animals↗
PubMed1979

Influence of elevated levels of linoleic acid on the thermal properties of bovine milk fat.

The thermal properties of bovine milk fat containing 15.5% linoleic acid have been compared with those of milk fat containing a normal level (1.8%) of linoleic acid in order to examine the influence of altered triglyceride (TG) composition on their physical characteristics. The total TGs of 18:2-rich milk fat melted over the range -38 to 30 C compared with the range -33 to 34 C for control milk fat. Polymorphism exhibited by the high mol wt TGs of control milk fat was absent in the same fraction of 18:2-rich milk fat. Similarly, the complex melting thermogram of the low mol wt TGs of control milk fat and its obvious polymorphic behavior contrasted with the single broad melting peak of the low mol wt TGs of 18:2-rich milk fat. This solid miscibility in the 18:2-rich milk fat could be a consequence of the lower proportion of saturated TGs or the presence of high proportions of diene and triene TGs containing 18:2 instead of monoene and diene TGs containing 18:1.

Animals↗
PubMed1994

Intestinal absorption of octanoic, decanoic, and linoleic acids: effect of triglyceride structure.

The influence of triglyceride structure on the intestinal absorption of specific triglycerides was investigated. A bolus of either a structured or a randomized oil was given to lymph-cannulated rats. The structured oil contained medium-chain fatty acids (MCFA) in the sn-1 and sn-3 position of the triglyceride, and linoleic acid (C18:2 n-6) in the sn-2 position, whereas in the randomized oil the same fatty acids were distributed randomly between the three positions. The absorption of MCFA was highest from the randomized oil, where approximately 33% of the MCFA were located in the sn-2 position. The absorption of C18:2 n-6 was highest from the structured oil, where C18:2 n-6 is located in the sn-2 position, indicating that the intestinal absorption is influenced by triglyceride structure, and that the absorption is enhanced for fatty acids located in the sn-2 position. Prior to lymph collection, the rats were fed either a fish oil or a vegetable oil diet. The absorption of C18:2 n-6 was highest in the rats previously fed the fish oil diet. The incorporation of the highly unsaturated fatty acids from the fish oil into the membrane phospholipids may thus influence the absorption of fat.

Animals↗
PubMed2005

Linoleic acid hydroperoxide reacts with hypochlorous acid, generating peroxyl radical intermediates and singlet molecular oxygen.

The reaction of hypochlorous acid (HOCl) with hydrogen peroxide is known to generate stoichiometric amounts of singlet molecular oxygen [O2 (1Deltag)]. This study shows that HOCl can also react with linoleic acid hydroperoxide (LAOOH), generating O2 (1Deltag) with a yield of 13 +/- 2% at physiological pH. Characteristic light emission at 1,270 nm, corresponding to O2 (1Deltag) monomolecular decay, was observed when HOCl was reacted with LAOOH or with liposomes containing phosphatidylcholine hydroperoxides, but not with cumene hydroperoxide or tert-butyl hydroperoxide. The generation of O2 (1Deltag) was confirmed by the acquisition of the spectrum of the light emitted in the near-infrared region showing a band with maximum intensity at 1,270 nm and by the observation of the enhancing effect of deuterium oxide and the quenching effect of sodium azide. Mechanistic studies using 18O-labeled linoleic acid hydroperoxide (LA18O18OH) showed that its reaction with HOCl yields 18O-labeled O2 (1Deltag) [18O2 (1Deltag)], demonstrating that the oxygen atoms in O2 (1Deltag) are derived from the hydroperoxide group. Direct analysis of radical intermediates in the reaction of LAOOH with HOCl by continuous-flow electron paramagnetic resonance spectroscopy showed a doublet signal with a g-value of 2.014 and a hyperfine coupling constant from the alpha-hydrogen of a(H) = 4.3 G, indicating the formation of peroxyl radicals. Taken together, our results clearly demonstrate that HOCl reacts with biologically relevant lipid hydroperoxides, generating O2 (1Deltag). In addition, the detection of 18O2 (1Deltag) and peroxyl radicals strongly supports the involvement of a Russell mechanism in the generation of O2 (1Deltag).

Hydrogen Peroxide↗
PubMed2000

Effect of calcium on the oxidation of linoleic acid by potato (Solanum tuberosum var. Desiree) tuber 5-lipoxygenase.

When the effect of calcium on the oxidation of linoleic acid by potato tuber 5-lipoxygenase (LOX) was investigated, it was seen to promote the enzyme's activity at pH values higher than the optimum pH of 6.3, resulting in an enzyme activation at alkaline pH. Kinetic analysis of calcium activation at different pH values revealed that the cation abolished the inhibition by high substrate concentration, which occurs in the absence of Ca(2+), thus leading to activation at high substrate concentration. Studies were conducted to investigate the influence of Ca(2+) on the physicochemical nature of the substrate and its effect on the LOX activity expression. It was concluded that the aggregation mode rather than the aggregation state of linoleic acid is responsible for potato 5-LOX changes.

Arachidonate 5-Lipoxygenase↗
PubMed1989

Effect of dietary linoleic acid level on lodgement, proliferation and survival of mammary tumor metastases.

High levels of dietary linoleic acid (18:2) have been shown to increase the spontaneous metastasis of line 4526 mouse mammary tumors. In this report, the influence of 18:2 on specific events of tumor metastasis, namely, lodgement, proliferation and survival, were studied using spontaneous and experimental metastasis assays with line 4526 cells. A significantly greater number of radiolabeled tumor cells lodged in the lungs of mice fed 4, 8 and 12% 18:2 when compared with mice fed lower levels of 18:2. The effect of dietary 18:2 appeared to be on the host tissue (lungs) and not the tumor cells. Lodgement of tumor cells first cultured in serum of mice fed 18:2 then injected into mice fed 1% 18:2 was not affected. There were no significant differences in the percentage of [3H]thymidine labeled metastatic cells from lungs of mice fed different levels of 18:2. However, the number of surface lung nodules that appeared in mice 21 days after injection of unlabeled line 4526 cells increased in mice fed 8 and 12% 18:2 compared with those fed lower levels of 18:2. Thus, dietary 18:2 may increase metastasis by influencing the lodgement, implantation and survival but not proliferation of line 4526 mouse mammary tumor cells.

Animals↗
PubMed2003

The effect of breed, parity, and stage of lactation on conjugated linoleic acid (CLA) in milk fat from dairy cows.

Dairy products are the main source of conjugated linoleic acid (CLA), a functional food component with health benefits. The major source of cis-9, trans-11 CLA in milk fat is endogenous synthesis via delta9-desaturase from trans-11 18:1, with the remainder from incomplete rumen biohydrogenation of linoleic acid. Diet has a major influence on milk fat CLA; however, effects of physiological factors have received little attention. Our objectives were to examine milk fat content of CLA and the CLA-desaturase index with regard to: 1) effect of breed, parity, and stage of lactation, and 2) variation among individuals and the relationship to milk and milk fat. Holstein (n = 113) and Brown Swiss (n = 106) cows were fed a single diet and milk sampled on the same day to avoid confounding effects of diet and season. Frequency distributions demonstrated that milk fat content of CLA and CLA-desaturase index varied over threefold among individuals, and this needs to be considered in the design of experiments. Holsteins had a higher milk fat content of CLA and CLA-desaturase index, but breed differences were minor. Parity and days in milk also had little or no relationship to the individual variation for these two CLA variables. Breed, parity, and days in milk accounted for < 0.1, < 0.3, and < 2.0% of total variation in CLA concentration in milk fat, respectively. Milk fat content of CLA and CLA-desaturase index were essentially independent of milk yield, milk fat percent, and milk fat yield. We speculate that the basis for the genetic variation among individuals is related to rumen output of trans-11 18:1 and to a lesser extent cis-9, trans-11 CLA, and to the tissue amount and activity of delta9-desaturase.

Animals↗
PubMed1988

Dietary linoleic acid, gastric acid, and prostaglandin secretion.

Basal and pentagastrin-stimulated gastric acid secretion, fasting serum gastrin concentrations, and the gastric output of prostaglandin E and its major metabolite 13,14-dihydro 15-keto prostaglandin E2 were measured in 9 normal subjects before and after 14-20 days of dietary supplementation with linoleic acid. Mean maximal gastric acid output fell from 36.0 +/- 3.3 (SEM) to 30.1 +/- 2.9 mmol/h (p less than 0.05), although mean basal acid output was not significantly affected (8.3 +/- 2.1 and 7.2 +/- 1.7 mmol/h, respectively). Mean fasting serum gastrin concentrations increased from 19.2 +/- 3.1 to 30.9 +/- 3.8 ng/L (p less than 0.01) after linoleic acid, probably because of acid suppression. The mean output of prostaglandin E increased from 498 +/- 110 to 1254 +/- 465 ng/h (p less than 0.05); that of its metabolite increased from 165 +/- 18 to 1168 +/- 645 ng/h (p less than 0.01). These findings show that in normal subjects essential fatty acid weakly inhibits gastric acid secretion, but considerably increases gastric prostaglandin output.

Adult↗
PubMed1990

Inhibition of benzo(a)pyrene-induced mouse forestomach neoplasia by conjugated dienoic derivatives of linoleic acid.

Grilled ground beef contains factors that inhibit the initiation of mouse epidermal carcinogenesis by 7,12-dimethylbenz(a)anthracene. Previously we isolated an active principal and characterized it as an isomeric mixture of conjugated dienoic derivatives of linoleic acid (CLA). We now show that synthetic CLA inhibits the initiation of mouse forestomach tumorigenesis by benzo(a)pyrene. Four and 2 days prior to p.o. treatment with benzo(a)pyrene, female ICR mice were given (a) CLA in olive oil, (b) linoleic acid in olive oil, or (c) olive oil alone or plus 0.85% saline (control groups). Three days later the cycle was repeated for a total of 4 times. At 30 wk of age, the mice were sacrificed. In three independent experiments, mice treated with CLA developed only about half as many neoplasms/animal as mice in the control groups (P less than 0.025); in two of the experiments tumor incidence was also reduced (P less than 0.05). There were no significant differences in food intake or body weight among the groups. High-performance liquid chromatography/gas chromatography analysis established that, following intubation, only the c-9, t-11 CLA isomer was incorporated into forestomach phospholipids. In studies aimed at elucidating the mechanism of action, we found that CLA is an effective antioxidant. Under the conditions of the test CLA was more potent than alpha-tocopherol and almost as effective as butylated hydroxytoluene. These observations indicate that CLA might serve as an in situ defense mechanism against membrane attack by free radicals and may, at least in part, explain the anticarcinogenic properties of CLA.

Animals↗
PubMed2002

Conjugated linoleic acid isomers and mammary cancer prevention.

There is increasing evidence that individual isomers of conjugated linoleic acid (CLA) may have unique biological or biochemical effects. A primary objective of this study was to determine whether there might be differences in the anticancer activity of 9,11-CLA and 10,12-CLA. This was achieved by evaluating the reduction in premalignant lesions and carcinomas in the mammary gland of rats that had been treated with a single dose of methylnitrosourea and given 0.5% of either highly purified CLA isomer in the diet. Our results showed that the anticancer efficacies of the two isomers were very similar. At 6 wk after carcinogen administration, the total number of premalignant lesions was reduced by 33-36%. At 24 wk, the total number of mammary carcinomas was reduced by 35-40%. The concentration of each CLA isomer and its respective metabolites was analyzed in the mammary fat pad. Tissue level of 10,12-CLA was much lower than that of 9,11-CLA. The pool of metabolites from each isomer was very similar between the two groups and represented only a small fraction of total conjugated diene fatty acids. Feeding of 9,11-CLA resulted in minimal changes in other unsaturated fatty acids. In contrast, feeding of 10,12-CLA produced a wider spectrum of perturbations. Small but significant increases in 16:1 and 16:2 were detected; these were accompanied by decreases in 20:2, 20:3, 20:4, 22:4, and 22:6. The above observation suggests that 10,12-CLA might be more potent than 9,11-CLA in interfering with elongation and desaturation of linoleic and linolenic acids. In summary, our study showed that, at the 0.5% dose level, the anticancer activity of 9,11-CLA and 10,12-CLA was very similar, even though accumulation of 10,12-CLA in the mammary tissue was considerably less than that of 9,11-CLA. These confounding changes of the other unsaturated fatty acids in contributing to the effect of 10,12-CLA need to be clarified.

Animals↗
PubMed2001

The biologically active isomers of conjugated linoleic acid.

Numerous physiological effects are attributed to conjugated linoleic acid (CLA). The purpose of this presentation is to consider these effects with respect to the cis-9,trans-11 and trans-10,cis-12 CLA isomers. We review previously published data and present new findings that relate to underlying biochemical mechanisms of action. Both isomers are natural products. The cis-9,trans-11 isomer is the principal dietary form of CLA, but the concentrations of this isomer and the trans-10,cis-12 isomer in dairy products or beef vary depending on the diet fed to cows or steers, respectively. The trans-10,cis-12 CLA isomer exerts specific effects on adipocytes, in particular reducing the uptake of lipid by inhibiting the activities of lipoprotein lipase and stearoyl-CoA desaturase. The trans-10,cis-12 CLA isomer also affects lipid metabolism in cultured Hep-G2 human liver cells, whereas both the cis-9,trans-11 and trans-10,cis-12 CLA isomers appear to be active in inhibiting carcinogenesis in animal models. We present new findings indicating that the cis-9,trans-11 CLA isomer enhances growth and probably feed efficiency in young rodents. Accordingly, the effects of CLA on body composition (induced by trans-10,cis-12 CLA) and growth/feed efficiency (induced by cis-9,trans-11 CLA) appear to be due to separate biochemical mechanisms. We also show that a 19-carbon CLA cognate (conjugated nonadecadienoic acid, CNA) inhibits lipoprotein lipase activity as effectively as CLA in cultured 3T3-L1 adipocytes. Presumably, CNA is metabolized differently than the 18-carbon CLA isomers, so this finding indicates direct activity of the administered compound as opposed to acting via a metabolite.

Adipocytes↗
PubMed1999

Lipase-catalyzed fractionation of conjugated linoleic acid isomers.

The abilities of lipases produced by the fungus Geotrichum candidum to selectively fractionate mixtures of conjugated linoleic acid (CLA) isomers during esterification of mixed CLA free fatty acids and during hydrolysis of mixed CLA methyl esters were examined. The enzymes were highly selective for cis-9,trans-11-18:2. A commercial CLA methyl ester preparation, containing at least 12 species representing four positional CLA isomers, was incubated in aqueous solution with either a commercial G. candidum lipase preparation (Amano GC-4) or lipase produced from a cloned high-selectivity G. candidum lipase B gene. In both instances selective hydrolysis of the cis-9,trans-11-18:2 methyl ester occurred, with negligible hydrolysis of other CLA isomers. The content of cis-9, trans-11-18:2 in the resulting free fatty acid fraction was between 94 (lipase B reaction) and 77% (GC-4 reaction). The commercial CLA mixture contained only trace amounts of trans-9,cis-11-18:2, and there was no evidence that this isomer was hydrolyzed by the enzyme. Analogous results were obtained with these enzymes in the esterification in organic solvent of a commercial preparation of CLA free fatty acids containing at least 12 CLA isomers. In this case, G. candidum lipase B generated a methyl ester fraction that contained >98% cis-9,trans-11-18:2. Geotrichum candidum lipases B and GC-4 also demonstrated high selectivity in the esterification of CLA with ethanol, generating ethyl ester fractions containing 96 and 80%, respectively, of the cis-9,trans-11 isomer. In a second set of experiments, CLA synthesized from pure linoleic acid, composed essentially of two isomers, cis-9,trans-11 and trans-10,cis-12, was utilized. This was subjected to esterification with octanol in an aqueous reaction system using Amano GC-4 lipase as catalyst. The resulting ester fraction contained up to 97% of the cis-9,trans-11 isomer. After adjustment of the reaction conditions, a concentration of 85% trans-10,cis-12-18:2 could be obtained in the unreacted free fatty acid fraction. These lipase-catalyzed reactions provide a means for the preparative-scale production of high-purity cis-9,trans-11-18:2, and a corresponding CLA fraction depleted of this isomer.

Chemical Fractionation↗
PubMed1976

The enzymic cleavage of linoleic acid to C9 carbonyl fragments in extracts of cucumber (Cucumis sativus) fruit and the possible role of lipoxygenase.

1. Homogenates and acetone powders of cucumber fruits catalyse the enzymic conversion of linoleic acid to aldehyde and oxoacid fragments in high yield, up to 60% with acetone powder extracts. 2. The major products are trans2-nonenal--a major component of the characteristic odour of cucumber--and 9-oxononanoic acid. 3. The cleavage reaction is a heat-labile, aerobic process, optimal at pH 6 (approx.). 4. Substrate specificity studies indicate that a lipoxygenase-type of reaction is involved in the cleavage process. 5. The acetone powder extracts have lipoxygenase activity and the proportion of linoleic acid hydroperoxide to carbonyl fragments depends upon incubation conditions. 6. Linoleic acid hydroperoxide isomers are also converted to carbonyl fragments by acetone powder extracts; the 9-hydroperoxide is cleaved at the 9-10 position whereas 12-13 cleavage is predominant with the 13-hydroperoxide isomer.

Chromatography, Gas↗