Struktur der F‐Säuren enthaltenden Plasmalipide

Puchta, Volker; Spiteller, Gerhard

doi:10.1002/jlac.198819881207

Cited by 20 publications

(7 citation statements)

References 17 publications

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“…F-acids were also found in marine bacteria (43)(44)(45), algae (46,47), plants (48)(49)(50), yeast (49) and fungi (49), food fats such as butter (51) and virgin olive oil (52), mammalian tissue (53), and blood in-cluding that of humans (54)(55)(56). Thus, F-acids seem to be widely distributed in all living matter.…”

Section: Occurrencementioning

confidence: 99%

“…In liver tissue of mammals, F-acids are enriched in the cholesterol ester and in the TG fraction (53), but in mammalian (54) and human blood plasma (54) they are found mainly in the choline and ethanolamine phospholipids (55). Thus, F-acids are not equally distributed in the different organs in either fish or mammals.…”

Section: Occurrencementioning

confidence: 99%

“…Diet-derived F-acids are incorporated into the tissue and blood of mammals, especially into phospholipids (54,55) where they partly substitute for PUFA. As a consequence, they are localized exactly at sites where LPO reactions occur in atherosclerosis and where they are needed to trap radicals.…”

Section: Reactions Of F-acidsmentioning

confidence: 99%

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Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Spiteller

2005

Lipids

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170

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Furan FA (F-acids) are tri- or tetrasubstituted furan derivatives characterized by either a propyl or pentyl side chain in one of the alpha-positions; the other is substituted by a straight long-chain saturated acid with a carboxylic group at its end. F-acids are generated in large amounts in algae, but they are also produced by plants and microorganisms. Fish and other marine organisms as well as mammals consume F-acids in their food and incorporate them into phospholipids and cholesterol esters. F-acids are catabolized to dibasic urofuran acids, which are excreted in the urine. The biogenetic precursor of the most abundant F-acid, F6, is linoleic acid. Methyl groups in the beta-position are derived from adenosylmethionine. Owing to the different alkyl substituents, synthesis of F-acids requires multistep reactions. F-acids react readily with peroxyl radicals to generate dioxoenes. The radical-scavenging ability of F-acids may contribute to the protective properties of fish and fish oil diets against mortality from heart disease.

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Section: Occurrencementioning

confidence: 99%

Section: Occurrencementioning

confidence: 99%

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Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Spiteller

2005

Lipids

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170

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“…However, there are also natural sources for furan fatty acids as from fish liver at 4000 mg/100 g and fish fillet at 900 mg/100 g down to plant oils at 5–42 mg/100 g . In addition furan fatty acids are known to be present in cholesterol esters and TAGs of ruminant liver and in human phospholipids like phosphatidyl ethanolamine and ‐choline . Furan fatty acids from fresh fish contain a methyl group at the ring carbons, while furan fatty acids from oxidative degradation do not contain these groups.…”

Section: Introductionmentioning

confidence: 99%

Fatty acid alterations in oils and fats during heating and frying*

Brühl

2014

Euro J Lipid Sci & Tech

113

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Oils and fats degrade during the frying process and many reactions with numerous fatty acid alteration products have been examined. The geometrical isomerisation of double bonds leads to the formation of trans fatty acids. At frying temperatures also conjugated double bond systems are detected. The reaction of oxygen with unsaturated fatty acids results in hydroperoxides, which immediately degrade in further radical reactions at frying temperature. A set of oxygenated fatty acids has been detected including epoxy-, keto-and hydroxyl fatty acids. Another route leads to b-scission at the carbonyl-or the alkyl side of the oxygen bearing carbon atom in the fatty acid chain. In this case short chain fatty acids, aldehydic, keto, and hydroxyl acids appear together with volatile compounds. Also the formation of cyclic and furan fatty acids was detected. As a reaction between fatty acids also dimeric and polymerised fatty acids can be observed. Taking into account the different amounts of these fatty acid degradation products the physiological relevance has to be discussed. Due to high concentrations of dimeric and polymerised molecules these substances can lower significantly the digestibility of fried foods, while oxidised fatty acid monomers are readily absorbed and raise concern about their effect on lipid metabolism. These two different effects of altered TAGs and fatty acids have to be considered separately.

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“…Long-chain fatty acids containing a furan nucleus, referred to as furan acids, have been identified in small amounts as constituents of triglycerides, phospholipids and sterol esters in certain species of fish (1,2) and plants (3), in soft corals (4), as well as in reptiles and amphibians (2). Furan fatty acids have been found to accumulate in different tissues of mammalian animals (5,6). Not much is known about the biological activity of furan fatty acids and their derivatives (7)(8)(9), and their biological role is not clear either.…”

mentioning

confidence: 99%

Inhibition of bacterial urease by autoxidation of furan C‐18 fatty acid methyl ester products

Rosenblat

Tabak

Jie

et al. 1993

J Americ Oil Chem Soc

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501Autoxidation products of synthetic methyl 9,12-epoxyoctadeca-9,11-dienoate (MEFA) were investigated by gas chromatography-mass spectrometry analysis and tested for bacterial urease inhibition. A suspension of oxidized MEFA in 10% Tween 80 was an effective inhibitor for bacterial urease extract from Helicobacter pylori (I50 --1.3 raM) and for commercial urease from Bacillus pasteurii (I50 --0.06 mM}. The urease inhibitory effect was cancelled by adding cysteine to the reaction mixture. The total content of biologically active oxidized products in the mixture was found to be 6.2%. Dioxo-ene derivatives of MEFA on the thin-layer chromatography plate surface were converted into more stable compounds, whose formation in the mixture reduced inhibition of B. pasteurii to about 2% of the former level. The mechanism of urease inhibition is supposed to involve the interaction of the thiol groups of the enzyme's active center with the inhibitor molecules.

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Struktur der F‐Säuren enthaltenden Plasmalipide

Cited by 20 publications

References 17 publications

Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Fatty acid alterations in oils and fats during heating and frying*

Inhibition of bacterial urease by autoxidation of furan C‐18 fatty acid methyl ester products

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