The effects of cyclic fatty acid monomers on cultured porcine endothelial cells

Flickinger, B. D.; McCusker, Robert H.; Perkins, E. G.

doi:10.1007/s11745-997-0119-8

Cited by 11 publications

(10 citation statements)

References 43 publications

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“…The increased CFAM concentration caused a decreased ratio of cellular lipids/protein, which may contribute to the reduced order of membrane lipids observed. Hence, prolonged CFAM presence in the diet might affect endothelium injury and degeneration in vitro (Flickinger et al, 1997). However, CFAM concentration in oxidized oil of poor quality is less than 0.5%, hence, the actual consumed concentration is rather low.…”

Section: Trans Fatty Acidsmentioning

confidence: 99%

Frying of Nutritious Foods: Obstacles and Feasibility.

Dana

Saguy

2001

FSTR

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Frying is an important cooking process due to the unique palatability and sensory characteristics of fried foods. Fried foods contain a considerable amount of fat, and have a negative perceived image due to their high caloric value and increased consumer awareness of the relationship between food, nutrition, and health. Oil consumption and especially saturated fat, is considered as one of the principal factors increasing health risks of heart disease, cancer, diabetes, and hypertension. The mechanism of oil uptake during frying is complex and affected by numerous factors, such as product and oil composition, surface-active agents, etc. Frying oil undergoes three main deleterious reactions: oxidation, hydrolysis and thermal decomposition, resulting in the formation of numerous constituents. The latter affect the organoleptic characteristics of the fried product, and could pose health risks. Frying has a significant role in the overall nutritional value of the product. Compared to other cooking methods, retention of water-soluble vitamins and vitamin E could be higher after frying. Due to the deterioration of oil after prolonged frying, regulations on the maximum levels of polar compounds and polymer concentration have been utilized. Nevertheless, an alarming number of oil samples collected from restaurants and fast food outlets in Europe failed to comply with regulations. Frying has only a marginal affect on the concentration of trans fatty acids. Yet, due to their possible connection with heart disease, the initial concentration of hydrogenated fats (that could reach 50%) should be considered. The relationships between frying and carcinogenesis and mutagenesis are inconclusive. Cyclic fatty acid monomers, which can be formed during frying, were proven harmful only in some studies. Exposure to malondialdehyde (MDA) during typical consumption of fried food constituted no actual health hazard, although MDA is known to be a very potent mutagen and carcinogen. Heterocyclic amines, formed during fish and meat frying, were related to higher cancer incidence, but only in concentrations which were higher by several orders of magnitude than those formed in typical frying. It is concluded that based on information to date, and using good manufacturing practices, fried foods pose no significant health hazard in a balanced diet.

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Section: Trans Fatty Acidsmentioning

confidence: 99%

Frying of Nutritious Foods: Obstacles and Feasibility.

Dana

Saguy

2001

FSTR

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“…It was suggested that incorporation of lipid peroxidation products apart from alterations of membrane lipid composition could account for the altered membrane fluidity observed in animals fed oxidized oils (3). A recent study investigating the effects of cyclic fatty acid monomers reported a decreased lipid packing order of membrane bilayers of cultured aortic endothelial cells associated with a reduced activity of Ca 2+ ATPase (33). These studies demonstrate that dietary treatment of animals with oxidized oils as well as incubation of isolated cells with lipid peroxidation products has profound effects on membrane structure and function.…”

Section: Tablementioning

confidence: 99%

The effects of a dietary oxidized oil on lipid metabolism in rats

Eder

1999

Lipids

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This study was carried out to investigate the effects of a dietary oxidized oil on lipid metabolism in rats, particularly the desaturation of fatty acids. Two groups of rats were fed initially for a period of 35 d diets containing 10% of either fresh oil or thermally treated oil (150 degrees C, 6 d). The dietary fats used were markedly different for lipid peroxidation products (peroxide value: 94.5 vs. 3.1 meq O2/kg; thiobarbituric acid-reactive substances: 230 vs. 7 micromol/kg) but were equalized for their fatty acid composition by using different mixtures of lard and safflower oil and for tocopherol concentrations by individual supplementation with DL-alpha-tocopherol acetate. In the second period which lasted 16 d, the same diets were supplemented with 10% linseed oil to study the effect of the oxidized oil on the desaturation of alpha-linolenic acid. During the whole period, all the rats were fed identical quantities of diet by a restrictive feeding system in order to avoid a reduced food intake in the rats fed the oxidized oil. Body weight gains and food conversion rates were only slightly lower in the rats fed the oxidized oil compared to the rats fed the fresh oil. Hence, the effects of lipid peroxidation products could be studied without a distortion by a marked reduced food intake and growth. To assess the rate of fatty acid desaturation, the fatty acid composition of liver and heart total lipids and phospholipids was determined and ratios between product and precursor of individual desaturation reactions were calculated. Rats fed the oxidized oil had reduced ratios of 20:4n-6/18:2n-6, 20:5n-3/18:3n-3, 20:4n-6/20:3n-6, and 22:6n-3/22:5n-3 in liver phospholipids and reduced ratios of 20:4n-6/18:2n-6, 22:5n-3/18:3n-3, and 22:6n-3/18:3n-3 in heart phospholipids. Those results suggest a reduced rate of desaturation of linoleic acid and alpha-linolenic acid by microsomal delta4-, delta5-, and delta6-desaturases. Furthermore, liver total lipids of rats fed the oxidized oil exhibited a reduced ratio between total monounsaturated fatty acids and total saturated fatty acids, suggesting a reduced delta9-desaturation. Besides those effects, the study observed a slightly increased liver weight, markedly reduced tocopherol concentrations in liver and plasma, reduced lipid concentrations in plasma, and an increased ratio between phospholipids and cholesterol in the liver. Thus, the study demonstrates that feeding an oxidized oil causes several alterations of lipid and fatty acid metabolism which might be of great physiologic relevance.

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“…Although the presence of CFAM in processed oils is observed at very low concentrations (0.01-0.7%), [5,6] it has been demonstrated that these compounds can affect the fatty acids metabolism [7,8] and are therefore potentially toxic to human health. [9,10] Other studies showed that the free or esterified forms of CFAM have a great influence on the intestinal metabolism and their lymphatic recovery. [11] The identification of the CFAM structures formed during the frying of vegetable oils was reported by Sebedio and Grandgirard, Dobson and Sebedio.…”

Section: Introductionmentioning

confidence: 99%

“…These compounds appear under the action of high temperatures (>200 °C). Although the presence of CFAM in processed oils is observed at very low concentrations (0.01–0.7%), it has been demonstrated that these compounds can affect the fatty acids metabolism and are therefore potentially toxic to human health . Other studies showed that the free or esterified forms of CFAM have a great influence on the intestinal metabolism and their lymphatic recovery .…”

Section: Introductionmentioning

confidence: 99%

GC‐MS Characterization of Cyclic Fatty Acid Monomers and Isomers of Unsaturated Fatty Acids Formed During the Soybean Oil Heating Process

Chérif

Boukhchina

Angers

2019

Euro J Lipid Sci & Tech

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In this work, the possibility of formation and isolation of cyclic fatty acid monomers (CFAM) from polyunsaturated fatty acids via prolonged heat treatment of soybean oil are studied. The structures of CFAM are determined using Gas chromatography‐Mass spectrometry (GC‐MS) of their 4, 4‐dimethyloxazoline (DMOX) derivatives, the yield of derivatization is 98%. Among CFAM, the cyclohexyl fatty acids with ring from C12 to C17 and the cyclohexneyl with ring from C10 to C15 formed acid are detected by GC‐MS. The new cyclopentyl with ring at C14 position or between C13 to C17 are detected from linoleic acid. Also, the variation of major fatty acids composition of soybean oil during heated treatment at 150, 180, 210, and 240 °C for 60 h are analyzed. The results indicate that after heating, soybean oil contains four isomers of conjugated linoleic acid (CLA), four isomers of C18:1 and four isomers of C18:3. The heating process, the enrichment steps, and CFAM concentration can modify the profile of CFAM and permit the emergence of new compounds, which can be useful to know the edible oil structural changes during the phases of extraction and analysis. Practical Applications: When heated at high temperature for a long time, soybean oil undergoes isomerization and cyclization reactions. In fact, CFAM structures with five and six membered carbon rings are identified from heated oil. A new mass spectrum of the CFAM derivative from the intramolecular C18:2 cyclization is also described. Although CFAM are present at very low concentrations in heated oils, these compounds are the most toxic metabolites produced in soybean oil heated at high temperature. In addition to the four isomers of conjugated linoleic acid, four isomers of C18:1 and four of C18:3 are detected during the heating process. The data clearly show that it is necessary to avoid heating the soybean oil to a temperature above 210 °C for a period of more than 60 h which can minimize the production of CFAM. The gap of 68 amu between the molecular ion (333) and m/z 265 indicate the location of cyclopentyl ring at C14, which is first determined in heated soybean oil.

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The effects of cyclic fatty acid monomers on cultured porcine endothelial cells

Cited by 11 publications

References 43 publications

Frying of Nutritious Foods: Obstacles and Feasibility.

Frying of Nutritious Foods: Obstacles and Feasibility.

The effects of a dietary oxidized oil on lipid metabolism in rats

GC‐MS Characterization of Cyclic Fatty Acid Monomers and Isomers of Unsaturated Fatty Acids Formed During the Soybean Oil Heating Process

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