The Specificity of Lipoxygenase-Catalyzed Lipid Peroxidation and the Effects of Radical- Scavenging Antioxidants

2002 ◽  
Vol 383 (3-4) ◽  
pp. 619-626 ◽  
Author(s):  
N. Noguchi ◽  
H. Yamashita ◽  
J. Hamahara ◽  
A. Nakamura ◽  
H. Kühn ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Linoleic Acid ◽  
Free Acid ◽  
Radical Scavenging ◽  
Density Lipoprotein ◽  
Side Reaction ◽  
Oxidation Products ◽  
Soybean Lipoxygenase ◽  
Reaction Products ◽  
Specific Product

Abstract The oxidation of low density lipoprotein (LDL) by lipoxygenase has been implicated in the pathogenesis of atherosclerosis. It has been known that lipoxygenasemediated lipid peroxidation proceeds in general via regio, stereo and enantiospecific mechanisms, but that it is sometimes accompanied by a share of random hydroperoxides as side reaction products. In this study we investigated the oxidation of various substrates (linoleic acid, methyl linoleate, phosphatidylcholine, isolated LDL, and human plasma) by the arachidonate 15-lipoxygenases from rabbit reticulocytes and soybeans aiming at elucidating the effects of substrate, lipoxygenase and reaction milieu on the contribution and mechanism of random oxidation and also the effect of antioxidant. The specific character of the rabbit 15-lipoxygenase reaction was confirmed under all conditions employed here. However, the specificity by soybean lipoxygenase was markedly dependent on the conditions. When phosphatidylcholine liposomes and LDL were oxygenated by soybean lipoxygenase, the product pattern was found to be exclusively regio, stereo, and enantiorandom. When free linoleic acid was incorporated into PC liposomes and oxidized by soybean lipoxygenase, the free acid was specifically oxygenated, whereas esterified linoleate gave random oxidation products exclusively. Radicalscavenging antioxidants such as αtocopherol, ascorbic acid and 2-carboxy-2,5,7,8-tetramethyl-6-chromanol selectively inhibited the random oxidation but did not influence specific product formation. It is assumed that the random reaction products originate from free radical intermediates, which have escaped the active site of the enzyme and thus may be accessible to radical scavengers. These data indicate that the specificity of lipoxygenasecatalyzed lipid oxidation and the inhibitory effects of antioxidants depend on the physicochemical state of the substrate and type of lipoxygenase and that they may change completely depending on the conditions.

scholarly journals Antioxidant Activity of Date Palm Fruit (Phoenix dactylifera L.) Extract for Oxidative Stabilisation of Butter Oil at Ambient Temperature

2015 ◽  
Vol 58 (2) ◽  
pp. 59-64
Author(s):  
Fazal Rahman ◽  
Muhammad Nadeem ◽  
Sabir Khan ◽  
Shakeel Ahmad ◽  
Yasir Zahoor
Keyword(s):  
Linoleic Acid ◽  
Ambient Temperature ◽  
Date Palm ◽  
Radical Scavenging ◽  
Phoenix Dactylifera ◽  
Oxidation Products ◽  
Total Phenolic ◽  
Palm Fruit ◽  
Butter Oil ◽  
Phoenix Dactylifera L

In this study, long term preservation of butter oil was achieved through ethanolic extract of date palm fruit (Phoenix dactylifera L.). Butter oil was supplemented with date palm fruit extract (DPFE) at three different concentrations i.e. 250, 500 and 750 ppm (T1, T2 and T3) and compared with a control. Total phenolic content, DPPH free radical scavenging activity and inhibition of linoleic acid peroxidation of the DPFE was 5.19 GAE, 74.2 and 81%, respectively. IC50 value of date extract for the inhibition of DPPH and linoleic acid peroxidation was 2.45 and 0.82 mg/mL, respectively. The loss of oleic acid and linoleic acid in control after six months of storage was 16 and 52% as compared to T3 which was 4% and 14%. T3 yielded the lowest concentration of primary and secondary oxidation products with no effect on sensory attributes. DPFE can be used to enhance the shelf life of  butter oil at ambient temperature. 

scholarly journals Antioxidant Activity and Chemical Composition of Essential Oils of some Aromatic and Medicinal Plants from Albania

2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Entela Hodaj-Çeliku ◽  
Olga Tsiftsoglou ◽  
Lulëzim Shuka ◽  
Sokol Abazi ◽  
Dimitra Hadjipavlou-Litina ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Essential Oils ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Stable Radical ◽  
In Vitro Assays ◽  
Bornyl Acetate ◽  
Soybean Lipoxygenase ◽  
Chemical Compositions ◽  
Caryophyllene Oxide

The chemical compositions have been investigated of the volatile oils of nine populations of six species from Albania, namely Artemisia absinthium, Calamintha nepeta, Hypericum perforatum, Sideritis raeseri subsp. raeseri, Origanum vulgare subsp. hirtum from two wild populations, and Salvia officinalis (sage) from two wild and one cultivated population,. The essential oils were obtained by hydrodistillation and their analyses were performed by GC–MS. The major constituents were: A. absinthium: neryl isovalerate (19.5%), geranyl isobutanoate (16.4%) and carvacrol (8.8%); C. nepeta: pulegone (31.7%), spathulenol (20.0%) and isomenthone (12.7%); H. perforatum: caryophyllene oxide (31.0%), δ-selinene (10.5%) and carvacrol (10.4%); O. vulgare: carvacrol (81.0, 78.6%), γ-terpinene (5.5, 7.1%) and p-cymene (4.9, 4.1%) for O. vulgare originating from Tepelena and Vlora, respectively; S. raeseri: carvacrol (36.7%), caryophyllene oxide (17.8%), β-caryphyllene (8.7%), spathulenol (7.7%) and myrtenol (6.4%); S. officinalis: camphor (40.2, 47.8, 45.9%), α-thujone (19.2, 22.2, 13.7%), eucalyptol (5.4, 2.6, 6.0%), camphene (5.8, 6.1, 3.9, %), borneol (2.1, 2.9, 5.7%) and bornyl acetate (3.3, 1.4, 5.6%) for samples originating from Tepelena, Tirana and Vlora, respectively. The essential oils were also tested for their free radical scavenging activity using the following in vitro assays: i) interaction with the free stable radical of DPPH (1,1-diphenyl-2-picrylhydrazyl), and ii) inhibition of linoleic acid peroxidation with 2,2'-azobis-2-methyl-propanimidamide, dihydrochloride (AAPH). Finally, their inhibitory activity toward soybean lipoxygenase was evaluated, using linoleic acid as substrate. The essential oil of O. vulgare (OV-VL) presented the highest interaction with the stable radical DPPH (76.5%), followed by that of A. absinthium (54.7%). O. vulgare (OV-TP) and A. absinthium showed high anti-lipid peroxidation activity, 97.5% and 96.5%, respectively, higher than that of the reference compound trolox (73.0%). Only the tested sample of O. vulgare (OV-VL) significantly inhibited soybean lipoxygenase (54.2%).

scholarly journals 6-Methoxyflavonol Glycosides with In Vitro Hepatoprotective Activity from Chenopodium Bonus-henricus Roots

2015 ◽  
Vol 10 (8) ◽  
pp. 1934578X1501000
Author(s):  
Zlatina Kokanova-Nedialkova ◽  
Magdalena Kondeva-Burdina ◽  
Dimitrina Zheleva-Dimitrova ◽  
Virginia Tzankova ◽  
Stefan Nikolov ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Linoleic Acid ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Rat Hepatocytes ◽  
2D Nmr ◽  
Cellular Damage ◽  
Flavonoid Glycosides ◽  
Frap Assay

One new, namely 6-methoxykaempferol 3- O-[β-apiofuranosyl(1→2)]-β-glucopyranosyl(1→6)-β-glucopyranoside (2), and two known flavonoid glycosides, spinacetin 3- O-[β-apiofuranosyl(1→2)]-β-glucopyranosyl(1→6)-β-glucopyranoside (1) and spinacetin 3- O-gentiobioside (3), were isolated from the roots of Chenopodium bonus-henricus L. Their structures were determined by means of spectroscopic methods (1D, 2D NMR, UV, IR) and HR-ESI-MS. Radical scavenging and anti-oxidant activities of 1 and 3 were established using DPPH and ABTS free radicals, FRAP assay and inhibition of lipid peroxidation (LP) in a linoleic acid system by the ferric thiocyanate method. Compound 3 was found to possess stronger DPPH and ABTS radical scavenging activity (IC50 0.44 ± 0.008 mM and 0.089 ± 0.002 mM, respectively) compared with 1 (IC50 1.22 ± 0.010 mM and 0.11 ± 0.004 mM, respectively). Both flavonoids inhibited the lipid peroxidation of linoleic acid significantly. Additionally, 1 and 3 significantly reduced the cellular damage caused by the hepatotoxic agent CCl4 in rat hepatocytes and preserved cell viability and GSH level, decreased LDH leakage and reduced lipid damage. Effects were similar to those of the positive control silymarin. Control of self-toxic effects made in a MTT based assay using HepG2 cells revealed statistically significant cytotoxic effects only in very high concentrations (exceeding mM) and an incubation time of 72 h, making flavonoid glycosides with a 6-methoxykaempferol skeleton a promising and safe class of hepatoprotective compounds.

Lipid Peroxidation Inhibitory Effects of Hizikia Fusiformis Methanolic Extract on Fish Oil and Linoleic Acid

2004 ◽  
Vol 10 (2) ◽  
pp. 65-72 ◽  
Author(s):  
Nalin Siriwardhana ◽  
K. -W. Lee ◽  
S. -H. Kim ◽  
J. -H. Ha ◽  
G. -T. Park ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Linoleic Acid ◽  
Fish Oil ◽  
Methanolic Extract ◽  
Uv Light ◽  
Lipid Peroxide ◽  
Oxidation Products ◽  
Butylated Hydroxytoluene ◽  
Inhibitory Effects ◽  
Hizikia Fusiformis

The lipid peroxidation inhibitory effects of Hizikia fusiformis methanolic extract (HME) on fish oil and linoleic acid were studied by means of peroxide value (PV), thiobarbituric acid-reactive substances (TBARS), conjugated diene hydroperoxides (CDH) and weight gaining assays. Heat and UV light stability were determined by DPPH assay. HME significantly (p<0.05) reduced the lipid peroxidation in a dosedependent manner. Increasing the level of HME from 0.01 to 0.1% caused a higher antioxidative effect than the one produced by butylated hydroxytoluene (BHT) (BHT reported the best effect compared to -tocopherol and butylated hydroxyanisole). HME reduced the formation of primary oxidation products as showed by the lower CDH values compared to its control counterpart. HME reduced also the addition of oxygen to form lipid peroxyl radicals that indicated a low weight gaining in HME-treated oils. Moreover, it could reduce the formation of lipid peroxide. Furthermore, it diminished the total lipid peroxidation resulting in low TBARS values. The heat and UV light study showed that H. fusiformis contained heat- and UV-light resistant antioxidants. These results indicated that the H. fusiformis antioxidants could be useful in preventing oxidative damages of food oils.

Antiatherogenic activity of extracts of Argania spinosa L. pericarp: beneficial effects on lipid peroxidation and cholesterol homeostasisThis article is one of a selection of papers published in this special issue (part 1 of 2) on the Safety and Efficacy of Natural Health Products.

2007 ◽  
Vol 85 (9) ◽  
pp. 918-927 ◽  
Author(s):  
Hicham Berrougui ◽  
Mounia Cherki ◽  
Geremy Abdull Koumbadinga ◽  
Maxim Isabelle ◽  
Jasmin Douville ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Cholesterol Efflux ◽  
Radical Scavenging ◽  
Density Lipoprotein ◽  
Inhibitory Effect ◽  
Ldl Oxidation ◽  
Lag Phase ◽  
Progression Rate ◽  
Natural Health Products ◽  
Dependent Manner

Prevention of lipoprotein oxidation by natural compounds may prevent atherosclerosis via reducing early atherogenesis. In this study, we investigated for the first time the beneficial properties of methanolic extract of argania pericarp (MEAP) towards atherogenesis by protecting human low-density lipoprotein (LDL) against oxidation while promoting high-density lipoprotein (HDL)-mediated cholesterol efflux. By measuring the formation of malondialdehyde (MDA) and conjugated diene as well as the lag phase and the progression rate of lipid peroxidation, the MEAP was found to possess an inhibitory effect. In addition, MEAP reduced the rate of disappearance of α-tocopherol as well as the apoB electrophoretic mobility in a dose-dependent manner. These effects are related to the free radical scavenging and copper-chelating effects of MEAP. In terms of cell viability, MEAP has shown a cytotoxic effect (0–40 μg/mL). Incubation of3H-cholesterol-loaded J774 macrophages with HDL in the presence of increasing concentrations of MEAP enhanced HDL-mediated cholesterol efflux independently of ABCA1 receptor pathways. Our findings suggest that argania seed pericarp provides a source of natural antioxidants that inhibit LDL oxidation and enhance cholesterol efflux and thus can prevent development of cardiovascular diseases.

Conversion of linoleic acid hydroperoxide by soybean lipoxygenase in the presence of guaiacol: Identification of the reaction products

Lipids ◽  
1975 ◽  
Vol 10 (12) ◽  
pp. 847-854 ◽  
Author(s):  
Günter Streckert ◽  
Hans-Jürgen Stan
Keyword(s):  
Linoleic Acid ◽  
Soybean Lipoxygenase ◽  
Linoleic Acid Hydroperoxide ◽  
Reaction Products ◽  
Acid Hydroperoxide

Melatonin Improves Lipid Profile and Ameliorates Lipid Peroxidation in Patients with Chronic Kidney Disease.

2018 ◽  
pp. 38-45
Keyword(s):  
Lipid Peroxidation ◽  
Placebo Group ◽  
Lipid Profile ◽  
Kidney Diseases ◽  
Oxidized Ldl ◽  
Low Density Lipoprotein ◽  
Density Lipoprotein ◽  
Before And After ◽  
Inhibit Lipid Peroxidation ◽  
Controlled Clinical Study

Dyslipidemia and oxidative modifications of lipid are frequently associated in patients with chronic kidney diseases (CKD) and considered the most important risk factors for cardiovascular events. Melatonin is a well-known potent antioxidant and has beneficial effect on lipid metabolism. the study was designed to evaluate if Melatonin could improve lipid profile and ameliorates lipid peroxidation. This single blind placebo controlled clinical study carried out on 41 patients with CKD who were randomized into two groups, control groups (n=20) those who received placebo cap and melatonin group those who received 5mg melatonin (n=21). Lipid profile [total cholesterol (TC), triglyceride (TG), high-density lipoprotein (HDL-C), low-density lipoprotein (LDL-C)] and parameters of lipid peroxidation [oxidized LDL (oxLDL) and malondialdehyde (MDA) were measured before and after 12 weeks of the treatment. After 12 weeks of treatment, melatonin significantly increased HDL-C and decreased LDL-C compared to the initial value. The elevation in HDL-C and reduction in LDL-C were significantly different from that in placebo group. Also, both oxLDL and MDA levels significantly lowered by melatonin compared to the baseline and to the placebo group. Collectively, the results of our study showed that melatonin has advantageous effect on lipid profile and inhibit lipid peroxidation in patients with CKD.

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