Preparative, enzymic synthesis of linoleic acid (13S)-hydroperoxide using soybean lipoxygenase-1

1990 ◽  
Vol 55 (5) ◽  
pp. 1690-1691 ◽  
Author(s):  
Gilles Iacazio ◽  
Georges Langrand ◽  
Jacques Baratti ◽  
Gerard Buono ◽  
Christian Triantaphylides
Keyword(s):  
Linoleic Acid ◽  
Soybean Lipoxygenase ◽  
Enzymic Synthesis

ChemInform Abstract: Preparative, Enzymatic Synthesis of Linoleic Acid (13S)-Hydroperoxide (I) Using Soybean Lipoxygenase-1.

ChemInform ◽  
1990 ◽  
Vol 21 (31) ◽  
Author(s):  
G. IACAZIO ◽  
G. LANGRAND ◽  
J. BARATTI ◽  
G. BUONO ◽  
C. TRIANTAPHYLIDES
Keyword(s):  
Linoleic Acid ◽  
Enzymatic Synthesis ◽  
Soybean Lipoxygenase

scholarly journals Steady-state kinetics of the anaerobic reaction of soybean lipoxygenase-1 with linoleic acid and 13-l-hydroperoxylinoleic acid

1978 ◽  
Vol 529 (3) ◽  
pp. 369-379 ◽  
Author(s):  
Jan Verhagen ◽  
Gerrit A. Veldink ◽  
Maarten R. Egmond ◽  
Johannes F.G. Vliegenthart ◽  
Jan Boldingh ◽  
...  
Keyword(s):  
Steady State ◽  
Linoleic Acid ◽  
Soybean Lipoxygenase ◽  
Steady State Kinetics ◽  
Hydroperoxylinoleic Acid ◽  
Kinetics Of ◽  
Anaerobic Reaction

The Steady-State Kinetics of the Oxygenation of Linoleic Acid Catalysed by Soybean Lipoxygenase

1976 ◽  
Vol 61 (1) ◽  
pp. 93-100 ◽  
Author(s):  
Maarten R. EGMOND ◽  
Maurizio BRUNORI ◽  
Paolo M. FASELLA
Keyword(s):  
Steady State ◽  
Linoleic Acid ◽  
Soybean Lipoxygenase ◽  
Steady State Kinetics ◽  
Kinetics Of

Oxidation of furan fatty acids by soybean lipoxygenase-1 in the presence of linoleic acid

1994 ◽  
Vol 70 (2) ◽  
pp. 179-185 ◽  
Author(s):  
Andreas Batna ◽  
Gerhard Spiteller
Keyword(s):  
Fatty Acids ◽  
Linoleic Acid ◽  
Soybean Lipoxygenase ◽  
Furan Fatty Acids

Evaluation of Lipoxygenase Inhibitory Activity of Anacardic Acids

2008 ◽  
Vol 63 (7-8) ◽  
pp. 539-546 ◽  
Author(s):  
Isao Kubo ◽  
Kazuo Ha ◽  
Kazuo Tsujimoto ◽  
Felismino E. Tocoli ◽  
Ivan R. Green
Keyword(s):  
Linoleic Acid ◽  
Inhibitory Activity ◽  
Specific Activity ◽  
Anacardium Occidentale ◽  
Side Chain ◽  
Soybean Lipoxygenase ◽  
Anacardic Acids ◽  
Alkyl Side Chains ◽  
Inhibitory Activities

6-Alkylsalicylic acids inhibit the linoleic acid peroxidation catalyzed by soybean lipoxygenase- 1 (EC 1.13.11.12, type 1) competitively and without pro-oxidant effects. This activity is largely dependent on the nature of their alkyl side chains. Inhibitory activities of anacardic acids, viz. 6-pentadec(en)ylsalicylic acids, isolated from the cashew Anacardium occidentale, were initially used for comparison because their aromatic head portions are the same. Consequently, the data should be interpreted to mean that changes in the hydrophobic side chain tail portions of the molecules evaluated correlate with the specific activity determined.

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 Radical adducts of nitrosobenzene and 2-methyl-2-nitrosopropane with 12,13-epoxylinoleic acid radical, 12,13-epoxylinolenic acid radical and 14,15-epoxyarachidonic acid radical. Identification by h.p.l.c.-e.p.r. and liquid chromatography-thermospray-m.s

1991 ◽  
Vol 276 (2) ◽  
pp. 447-453 ◽  
Author(s):  
H Iwahashi ◽  
C E Parker ◽  
R P Mason ◽  
K B Tomer
Keyword(s):  
Liquid Chromatography ◽  
Linoleic Acid ◽  
Hyperfine Splitting ◽  
Spin Trapping ◽  
Soybean Lipoxygenase ◽  
Acid Radical ◽  
Radical Adduct ◽  
The Masses ◽  
Hydroperoxylinoleic Acid ◽  
Additional Hyperfine

Linoleic acid-derived radicals, which are formed in the reaction of linoleic acid with soybean lipoxygenase, were trapped with nitrosobenzene and the resulting radical adducts were analysed by h.p.l.c.-e.p.r. and liquid chromatography-thermospray-m.s. Three nitrosobenzene radical adducts (peaks I, II and III) were detected; these gave the following parent ion masses: 402 for peak I, 402 for peak II, and 386 for peak III. The masses of peaks I and II correspond to the linoleic acid radicals with one more oxygen atom [L(O).]. The radicals are probably carbon-centred, because the use of 17O2 did not result in an additional hyperfine splitting. Computer simulation of the peak I radical adduct e.p.r. spectrum also suggested that the radical is carbon-centred. The peak I radical was also detected in the reaction of 13-hydroperoxylinoleic acid with FeSO4. From the above results, peak I is probably the 12,13-epoxylinoleic acid radical. An h.p.l.c.-e.p.r. experiment using [9,10,12,13-2H4]linoleic acid suggested that the 12,13-epoxylinoleic acid radical is a C-9-centred radical. Peak II is possibly an isomer of peak I. Peak III, which was observed in the reaction mixture without soybean lipoxygenase, corresponds to a linoleic acid radical (L.). The 12,13-epoxylinoleic acid radical, 12,13-epoxylinolenic acid radical and 14,15-epoxyarachidonic acid radical were also detected in the reactions of linoleic acid, linolenic acid and arachidonic acid respectively, with soybean lipoxygenase using nitrosobenzene and 2-methyl-2-nitrosopropane as spin-trapping agents.

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.

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