Linoleic acid peroxidation products are metabolized by hydrogenation in porcine liver tissue

Hecht, Stefan; Spiteller, Gerhard

doi:10.1255/ejms.238

Cited by 7 publications

(3 citation statements)

References 33 publications

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“…A minor contribution to this ion may result from secondary cleavage of the m/z 259 ion by loss of CH 3 OH. Location of the double bond between C-12 and C-13 was confirmed based on the presence of the fragment ion at m/z 124 corresponding to 1,3-nonadiene, as described previously [23]. a Trimethylsilyl-ether of isoricinoleic acid FAME, b 9oxo-cis-12-octadecenoic acid FAME, c Dimethyl disulfide adduct of 9-oxo-cis-12octadecenoic acid FAME.…”

Section: Identification Of Fasmentioning

confidence: 95%

Identification and Distribution of Oxygenated Fatty Acids in Plantago Seed Lipids

Smith

Zhang

Purves

2014

J Americ Oil Chem Soc

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Plant oils rich in oxygenated fatty acids (FAs) are of interest as renewable raw materials for industry. Previous studies reported unusual oxygenated FAs in the seed lipids of Plantago major and P. ovata. To determine if oxygenated FAs are a common component of Plantago seed oils, seed fatty acyl quality and quantity were determined for 23 Plantago species. Fatty acyl content, as a percentage of dry weight, ranged from 4.9 % in P. sempervirens to 18.8 % in P. coronopus. Oxygenated FAs were a frequent, but not ubiquitous component of Plantago seed lipids, reaching a level of almost 15 % in the seeds of P. nivalis. The oxygenated FAs were identified as isoricinoleic acid (9-hydroxy-cis-12-octadecenoic acid, IR) and 9-oxo-cis-12-octadecenoic acid (OX). When present, most species contained both IR and OX. FAs containing oxo groups have not been reported as components of the seed oil of other plant species that synthesize IR or ricinoleic acid (12-hydroxy-cis-9-octadecenoic acid), suggesting unique aspects to the pathway of oxygenated FA biosynthesis in Plantago. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) demonstrated that IR and OX are components of triacylglycerol, and triacylglycerol estolides are a minor component of the seed oil of P. lanceolata with secondary acylation by oxygenated FAs.FA nomenclature X:Y Dz where X is the chain length, Y is the number of double bonds and Dz is the double bond position relative to the carboxyl end of the molecule Tricylglycerol nomenclature TAG (A:B) where A is the number of carbon atoms in the acyl groups and B is the total number of double bonds IntroductionDue to the unique properties conferred by the hydroxyl group, oils containing hydroxy fatty acids (HFAs) have considerable potential as sources of sustainable feedstocks

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Section: Identification Of Fasmentioning

confidence: 95%

Identification and Distribution of Oxygenated Fatty Acids in Plantago Seed Lipids

Smith

Zhang

Purves

2014

J Americ Oil Chem Soc

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“…The position of the double bond between C12 and C13 has previously been confirmed for IR from N. oleander by oxidative cleavage [8]. It has also been suggested that the ion at m/z 124 seen in the mass spectrum of TMS-IR-FAMES corresponds to ionized 1,3 nonadiene, a fragment from the methyl end of IR resulting from cleavage αto the OTMS group, placing the double bond between carbons 12 and 13 [22]. The acyl composition of seeds of W. natalensis and S. speciosus (syn.…”

Section: Seed Acyl Compositionmentioning

confidence: 67%

Apocynaceae Seed Lipids: Characterization and Occurrence of Isoricinoleic Acid and Triacylglycerol Estolides

Smith

Zhang

2015

J Americ Oil Chem Soc

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“…Nevertheless they suffer slow degradation. They are mainly degraded primarily by hydrogenation and not by oxidation, as might be assumed 32. The ability to remove LOH by reduction decreases with increasing age.…”

Section: Markers For Lipid Peroxidation Processesmentioning

confidence: 91%

Are Changes of the Cell Membrane Structure Causally Involved in the Aging Process?

Spiteller

2002

Annals of the New York Academy of Sciences

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Lipid peroxidation is recognized by proliferation, wounding, and aging. The connecting link between these different events is a change in cell wall structure, which activates membrane bound phospholipases. These cleave phospholipids. Thus liberated polyunsaturated fatty acids (PUFAs) are substrates for lipoxygenases, which accept equally well linoleic acid and arachidonic acid and generate lipid hydroperoxides (LOOHs). If the amount of free PUFAs exceeds a certain amount, lipoxygenases commit suicide. The consequence is liberation of free iron ions that react with LOOHs by formation of radicals. These start a chain reaction. LOO* radicals produced in the course of this process attack proteins, nucleic acids, and also double bonds of all unsaturated compounds by epoxidation. Morever LOOHs are decomposed to toxic epoxy acids and alphabetagammadelta-unsaturated aldehydes. Both species react with glutathione. The resulting products seem to induce apoptosis. Since the products generated by wounding or aging are formed by decomposition of LOOHs the investigation of the aging processes can be simplified by studying the physiological action of artificially generated lipid peroxidation products derived from pure PUFAs. Degradation products of LOOHs are generated by thermal decomposition of fat-containing PUFAs. These products are induced into the body by adsorption in the intestine. They are at least partly incorporated in low density lipoproteins (LDLs). Primarily investigations seem to indicate that an overload of a diet rich in PUFAs induces only after two days an increase in oxidized LDL/PUFAs for a factor up to two in young people and for a factor of more than two in old individuals.

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Linoleic acid peroxidation products are metabolized by hydrogenation in porcine liver tissue

Cited by 7 publications

References 33 publications

Identification and Distribution of Oxygenated Fatty Acids in Plantago Seed Lipids

Identification and Distribution of Oxygenated Fatty Acids in Plantago Seed Lipids

Apocynaceae Seed Lipids: Characterization and Occurrence of Isoricinoleic Acid and Triacylglycerol Estolides

Are Changes of the Cell Membrane Structure Causally Involved in the Aging Process?

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