Role and Detection of 9 and 13-Hydroxyoctadecadienoic Acids

Spindler, Stephen A.; Clark, Kristi S.; Callewaert, Denis M.; Reddy, Ramesh G.

doi:10.1007/978-1-4899-1813-0_70

Cited by 3 publications

(3 citation statements)

References 8 publications

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“…The formation of these compounds could be related to the limited amount of oxygen in contact with the oil in this process in comparison to the process at 70 °C with aeration, in which only hydroperoxides were detected. The formation of hydroxy primary oxidation compounds in endogenous oxidation processes of lipids, detected in urine and serum , , is known. It is considered as a clinical marker of lipid peroxidation and oxidative stress.…”

Section: Resultsmentioning

confidence: 99%

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and ¹H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

Guillén

Goicoechea

2007

J. Agric. Food Chem.

101

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The oxidation of sunflower oil, stored in closed receptacles at room temperature for a period of 10 years, was monitored using Fourier transform infrared spectroscopy (FTIR) and 1H nuclear magnetic resonance (NMR). The objective was to understand the evolution of the oxidation process in sunflower oil under the conditions above mentioned. These techniques provide information about the oxidative status of several oil samples and the primary and some of the secondary oxidation products formed in the oxidation process. The results obtained show that, under these conditions, sunflower oxidation takes place in a different way to that at higher temperatures with aeration. The 1H NMR spectra show that in the first oxidation stages of the process only hydroperoxides supporting cis, trans-conjugated double bonds are formed and that at more advanced stages hydroperoxides having trans, trans-conjugated double bonds are generated, with the latter always being in a smaller proportion than the former. In addition, the presence of hydroxy derivatives supporting cis, trans-conjugated double bonds among the primary oxidation compounds is shown for the first time. Also, from early oxidation stages onward and unlike the process at 70 degrees C with aeration, it is noticeable that 4-hydroxy- trans-2-alkenals are formed in much higher proportions than 4-hydroperoxy- trans-2-alkenals. This fact could be associated with the presence of hydroxy derivatives with cis, trans-conjugated double bonds among the primary oxidation products and the limited concentration of oxygen during the oxidation. Furthermore, relationships between some oxidation conditions and the oxidation level of the samples were statistically analyzed.

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Section: Resultsmentioning

confidence: 99%

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and ¹H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

Guillén

Goicoechea

2007

J. Agric. Food Chem.

101

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“…As far as we know, only 1 previous paper has reported the formation, in SF oil after prolonged storage, of ( Z,E )‐conjugated diene primary oxidation products having hydroxy groups (Mikolajczak and others ). The formation of this kind of compounds is known to occur in in vivo oxidation processes, and, in fact, they are considered as clinical markers of lipid peroxidation and oxidative stress, usually detected in urine and serum (Spindler and others ; Browne and Armstrong ). Similarly, the formation of either ( Z,E )‐ or ( E,E )‐conjugated dienic systems related to hydroperoxy groups is highly dependent on the conditions to which the oil is submitted.…”

Section: H Nmr As a Tool For The Study Of Food Lipid Thermo‐oxidatiomentioning

confidence: 99%

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

Martínez‐Yusta

Goicoechea

Guillén

2014

Comp Rev Food Sci Food Safe

146

153

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This review summarizes present-day knowledge provided by proton nuclear magnetic resonance ( 1 H NMR) concerning food lipid thermo-oxidative degradation. The food lipids considered include edible oils and fats of animal and vegetable origin. The thermo-oxidation processes of food lipids of very different composition, occurring at low, intermediate, or high temperatures, with different food lipid surfaces exposed to oxygen, are reviewed. Mention is made of the influence of both food lipid nature and degradative conditions on the thermo-oxidation process. Interest is focused not only on the evolution of the compounds that degrade, but also on the intermediate or primary oxidation compounds formed, as well as on the secondary ones, from both qualitative and quantitative points of view. Very valuable qualitative and quantitative information is provided by 1 H NMR, which can be useful for metabolomic and lipidomic studies. The chemical shift assignments of spectral signals of protons of primary (hydroperoxides and hydroxides associated with conjugated dienes) and secondary, or further (aldehydes, epoxides, among which 9,10-epoxy-12-octadecenoate [leukotoxin] can be cited, alcohols, ketones) oxidation compounds is summarized. It is worth noting the ability of 1 H NMR to detect toxic oxygenated α,β-unsaturated aldehydes, like 4-hydroperoxy-, 4,5-epoxy-, and 4-hydroxy-2-alkenals, which can be generated in the degradation of food lipids having omega-3 and omega-6 polyunsaturated groups in both biological systems and foodstuffs. They are considered as genotoxic and cytotoxic, and are potential causative agents of cancer, atherosclerosis, and Parkinson's and Alzheimer's diseases.

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“…Other species of monohydroxy fatty acids are the hydroxyoctadecadienoic acids (HODEs), which are generated enzymatically by COX and LOX and cytochrome P450 pathways directly from LA; however the bulk of linoleic acid peroxidation occurs by non-enzymatic processes. HODEs are excellent indicators of free-radical-mediated lipid peroxidation (14). …”

Section: Introductionmentioning

confidence: 99%

HDL lipid composition is profoundly altered in patients with type 2 diabetes and atherosclerotic vascular disease

Morgantini

Meriwether

Baldi

et al. 2014

Nutrition, Metabolism and Cardiovascular Diseases

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Background and Aims We have previously shown that the anti-inflammatory and anti-oxidant functions of HDL are impaired in T2D patients. In this study, we examined whether HDL from T2D patients contains elevated levels of oxidized fatty acids and whether those levels correlate with cardiovascular disease (CVD). Methods and Results HETEs and HODEs on HDL were determined by LC-MS/MS in 40 non-diabetic controls (ND), 40 T2D without CVD (D+CVD−) and 38 T2D with known history of CVD (D+CVD+). HDL oxidant index was evaluated by a cell-free assay using dichlorofluorescein. Twenty-six randomly selected subjects from the three groups underwent coronary calcium score evaluation (CAC). Major cardiovascular risk factors were similar among the groups. HETEs and HODEs content were significantly increased in HDL from D+CVD+ when compared to D+CVD− and ND patients. HDL oxidant index was not different among the three groups; however, it was significantly higher in patients with CAC score >100 when compared to patients with CAC score <100. Conclusion Patients with D+CVD− and D+CVD+ are characterized by a severe, graded enrichment of oxidized fatty acids on HDL. In the present study, a loss of HDL function (as estimated by the HDL oxidant index) is observed only in patients with more advanced atherosclerosis.

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Role and Detection of 9 and 13-Hydroxyoctadecadienoic Acids

Cited by 3 publications

References 8 publications

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and ¹H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and ¹H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

HDL lipid composition is profoundly altered in patients with type 2 diabetes and atherosclerotic vascular disease

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Role and Detection of 9 and 13-Hydroxyoctadecadienoic Acids

Cited by 3 publications

References 8 publications

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and 1H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and 1H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by 1H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

HDL lipid composition is profoundly altered in patients with type 2 diabetes and atherosclerotic vascular disease

Contact Info

Product

Resources

About

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and ¹H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

Detection of Primary and Secondary Oxidation Products by Fourier Transform Infrared Spectroscopy (FTIR) and ¹H Nuclear Magnetic Resonance (NMR) in Sunflower Oil during Storage

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature