Effects of soybean lipoxygenase‐1 on phosphatidylcholines containing furan fatty acids

Batna, Andreas; Spiteller, Gerhard

doi:10.1007/bf02537308

Cited by 22 publications

(10 citation statements)

References 64 publications

(22 reference statements)

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“…141 These compounds, instead of PUFAs, are incorporated into the phospholipids of mammals 142 and therefore seem to fulfill the requirements to act as potent scavengers in humans. Another scavenger molecule with these properties containing an enlarged resonance system is vitamin E.…”

Section: Radical Scavengersmentioning

confidence: 99%

Is Lipid Peroxidation of Polyunsaturated Acids the Only Source of Free Radicals That Induce Aging and Age-Related Diseases?

Spiteller

2010

Rejuvenation Research

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The increase in free radicals is hypothesised to cause aging and age-related diseases. The most common source of free radicals is thought to be superoxide. This superoxide is claimed to be released from mitochondria during the enzymatic transformation of oxygen to water by a "leakage" process. This article presents evidence that leakage does not occur. Instead, protonated superoxide radicals are generated by lipid peroxidation processes. In nature, polyunsaturated fatty acids (PUFAs) represent particularly oxygen-sensitive compounds. Apparently, nature uses this sensitivity for signalling processes by producing lipidhydroperoxides (LOOHs) by any change to cell membrane structure. LOOHs easily undergo further enzymatic transformations to compounds which contribute to activation of genes. Bivalent metal ions within the active site of lipoxygenases catalyse LOOH production. The metal ions generate radicals which are transformed within the enzyme complex to non-radical molecules. Thus radicals never leave the enzyme complex except in severe stress situations. In this case the radical intermediates attack bonds, keeping the metal ion in its complex state. Thus, metal ions are released and react in a Fenton reaction with LOOH molecules produced earlier by lipoxygenase to form LO. radicals. Radicals are typically four orders of magnitude more reactive than non-radical molecules. Their action is not under genetic control, they attack nearly all biological molecules, destroying lipids, proteins, nucleic acids, hormones and enzymes until the radicals are quenched by scavenger molecules. The principal degradation routes are outlined in this review. Lysophospholipids are generated in large amounts after stress by activation of phospholipases and are transformed to LO. radicals. These can abstract a hydrogen radical from a lysophospholipid. The radical thus formed adds oxygen and decomposes to a 2-oxolysophospholipid and a HOO. radical (protonated superoxide). HOO. radicals in turn abstract hydrogen atoms from other molecules and produce H(2)O(2). Since any cell preparation method causes membrane destruction, it is inevitable that protonated superoxide is generated, explaining why H(2)O(2) molecules are found as "byproducts" of many reactions.

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Section: Radical Scavengersmentioning

confidence: 99%

Is Lipid Peroxidation of Polyunsaturated Acids the Only Source of Free Radicals That Induce Aging and Age-Related Diseases?

Spiteller

2010

Rejuvenation Research

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“…The oxidation of furanoid fatty acids has been studied by Boyer et al (10), Zabolotsky et al (11), and Batna and Spitellar (4,12). These studies indicated that the furan ring in furanoid acids could be co-oxidized by linoleate hydroperoxide with the ring opening to form a conjugated dioxoene.…”

mentioning

confidence: 96%

“…The dioxoene formed from dialkylfuranoids was more stable that those of tri-and tetraalkylfuranoids, which underwent further reaction. Tetraalkyl-substituted furanoid acids were also capable of scavenging free radicals generated during oxidation reactions and suppressing the oxidation of linoleic acid (12,13). The trialkyl furanoids were about one-half as effective as the tetraalkyl varieties in retarding oxidation, and the dialkyl showed no significant activity.…”

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confidence: 98%

Analysis of furanoid esters in soybean oil and the effect of variety and environment on furanoid ester content

Hammond

White

et al. 1997

J Americ Oil Chem Soc

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An improved method was developed to analyze the major furanoid esters in soybean oil. The method is based on urea fractionation of the methyl esters, silver ion chromatography, and gas chromatography of the furanoid concentrate. Activation of the soybean lipoxygenase decreased the amount of furanoid ester recovered from the oil, but the degumming of crude soybean oil and the choice of solvent used to extract soybean lipids caused no change in furanoid ester content. Fifty-six soybean varieties, representing a wide range in maturity group and geographical origin, were grown in Puerto Rico and used to determine the range of furanoid ester contents. Furanoid ester II ranged from 0.033-0.29 mg/g, and ester III ranged from 0.058-0.27 mg/g. The two major furanoid esters were positively correlated with each other and with maturity group. Growth environment as well as variety caused significant differences in furanoid content. JAOCS 74, 1099-1103 (1997). KEY WORDS:Analysis, effect of growth environment, effect of variety, furanoid fatty acids.Fatty acids containing a furan ring, or furanoid fatty acids, were first discovered by Morris et al. (1) in the seed oil of Exocarpus cupressiformis. More than 30 furanoid acids have been reported in a variety of animal and plant sources.The physiological role of these acids remains a matter of speculation. They may be involved in animal reproductive rhythms (2) and embryo development (3). Batna and Spitellar (4) suggest that they may act as antioxidants in plants. Furanoid acids inhibit lysyl oxidase and may be useful in the treatment of diseases that entail excess collagen and elastin deposition (5). Their biosynthetic pathway is not clear.Besides the seed oil of E. cupressiformis, furanoid esters have been found in algae (Chlorophyta sp.), mushroom (Agaricus bisporus), and yeast (Saccharomyces cerevisiae); they are also found in the roots and shoots of grasses (Poaceae sp.), clover (Trifolium pratense), dandelion (Taraxacum officinale), chive (Allium sativum), wheat (Triticum aestivum), rice (Oryza sativa), potato (Solanum tuberosum), cabbage (Brassica oleracea), orange (Citrus sinensis osbeck), lemon (Citrus limon), strawberries (Fragaria sp.), and birch leaves (Betula pendula) (6) as well as the latex of Hevea brasiliensis (7). Furanoid esters occur in greater amounts in the green parts of plants than in the stems, roots, and seeds.Three furanoid acids were identified in soybean oil by Guth and Grosch (8) and are shown in Figure 1. Guth and Grosch (8) reported that the three furanoid esters totaled 250-390 mg/kg in soybean oil, 70-120 mg/kg in wheat germ oil, 13-36 mg/kg in rapeseed oil, and 17-24 mg/kg in corn oil. Furanoid esters were absent in olive and sunflower oils. Analyses of the soybean cultivar Century and five soybean genotypes that lacked one or two of the three lipoxygenase isoenzymes revealed that their seed oils contained 190-225 mg/kg of furanoid ester II and 91-132 of ester III (9). The concentrations of furanoid esters were not correlated with lipoxygenase ...

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“…A detailed study [39] of this reaction revealed that it was inhibited if an iron chelator (EDTA) was added. The only available source of iron ions in this experiment was LOX, consequently proving the decomposition of LOX in the course of the reaction.…”

Section: Lpo Processes Are Involved In Cell Damagementioning

confidence: 98%

“…The LOXs are destroyed after some cycles due to the high content of LA and this liberates the iron ions required for cleavage of LOOH molecules. The thus generated LO9 radicals then attack the F-acids to convert these into dioxoenes and serve therefore as radical scavengers [39,40].…”

Section: Lpo Processes Are Involved In Cell Damagementioning

confidence: 99%

The relation of lipid peroxidation processes with atherogenesis: A new theory on atherogenesis

Spiteller¹

2005

Mol. Nutr. Food Res.

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The extremely high sensitivity of polyunsaturated fatty acids (PUFAs) to oxygen is apparently used by nature to induce stepwise appropriate cell responses. It is hypothesized that any alteration in the cell membrane structure induces influx of Ca2+ ions. Ca2+ ions are required to activate degrading enzymes, such as phospholipases and lipoxygenases (LOX) that transform PUFAs bound to membrane phospholipids to lipidhydroperoxides (LOOHs). Enzymatic reduction products of LOOHs seem to serve as ligands of proteins, which induce gene activation to initiate a physiological response. Increasing external impact on cells is connected with deactivation of LOX, liberation of the iron ion in its active center followed by cleavage of LOOH molecules to LO * radicals. LO * radicals induce a second set of responses leading to generation of unsaturated aldehydic phospholipids and unsaturated epoxyhydroxy acids that contribute to induction of apoptosis. Finally peroxyl radicals are generated by attack of LO * radicals on phospholipids. The latter attack nearly all types of cell constituents: Amino- and hydroxyl groups are oxidized to carbonyl functions, sugars and proteins are cleaved, molecules containing double bonds such as unsaturated fatty acids or cholesterol suffer epoxidation. LOOH molecules and iron ions at the cell wall of an injured cell are in tight contact with phospholipids of neighboring cells and transfer to these reactive radicals. Thus, the damaging processes proceed and cause finally necrosis except the chain reaction is stopped by scavengers, such as glutathione. Consequently, PUFAs incorporated into phospholipids of the cell wall are apparently equally important for the fate of a single organism as the DNA in the nucleus for conservation of the species. This review intends to demonstrate the connection of cell alteration reactions with induction of lipid peroxidation (LPO) processes and their relation to inflammatory diseases, especially atherosclerosis and a possible involvement of food. Previously it was deduced that food rich in cholesterol and saturated fatty acids is atherogenic, while food rich in n-3 PUFAs was recognized to be protective against vascular diseases. These deductions are in contradiction to the fact that saturated fatty acids withstand oxidation while n-3 PUFAs are subjected to LPO like all other PUFAs. Considering the influence of minor food constituents a new theory about atherogenesis and the influence of n-3 PUFAs is represented that might resolve the contradictory results of feeding experiments and chemical experiences. Cholesterol-PUFA esters are minor constituents of mammalian derived food, but main components of low density lipoprotein (LDL). The PUFA part of these esters occasionally suffers oxidation by heating or storage of mammalian derived food. There are indications that these oxidized cholesterol esters are directly incorporated into lipoproteins and transferred via the LDL into endothelial cells where they induce damage and start the sequence of events outlined above. The d...

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Effects of soybean lipoxygenase‐1 on phosphatidylcholines containing furan fatty acids

Cited by 22 publications

References 64 publications

Is Lipid Peroxidation of Polyunsaturated Acids the Only Source of Free Radicals That Induce Aging and Age-Related Diseases?

Is Lipid Peroxidation of Polyunsaturated Acids the Only Source of Free Radicals That Induce Aging and Age-Related Diseases?

Analysis of furanoid esters in soybean oil and the effect of variety and environment on furanoid ester content

The relation of lipid peroxidation processes with atherogenesis: A new theory on atherogenesis

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