scholarly journals An anaerobic reaction between lipoxygenase, linoleic acid and its hydroperoxides

1971 ◽  
Vol 122 (3) ◽  
pp. 327-332 ◽  
Author(s):  
G. J. Garssen ◽  
J. F. G. Vliegenthart ◽  
J. Boldingh
Keyword(s):  
Linoleic Acid ◽  
Dienoic Acid ◽  
Structural Rearrangement ◽  
Soya Bean ◽  
Acid Radical ◽  
Hydrogen Radical ◽  
Anaerobic Reaction ◽  
Anaerobic System

In an anaerobic system soya-bean lipoxygenase together with linoleic acid induces a structural rearrangement of 13-hydroperoxyoctadeca-cis-9-trans-11-dienoic acid leading to the formation of 13-oxotrideca-cis(trans)-9-trans-11-dienoic acid and n-pentane as well as 13-oxo-octadeca-9,11-dienoic acid. It is proposed that the 13-peroxyoctadeca-cis-9-trans-11-dienoic acid radical formed through hydrogen radical abstraction by the linoleic acid radical is the key intermediate for these reactions.

scholarly journals The origin and structures of dimeric fatty acids from the anaerobic reaction between soya-bean lipoxygenase, linoleic acid and its hydroperoxide

1972 ◽  
Vol 130 (2) ◽  
pp. 435-442 ◽  
Author(s):  
G. J. Garssen ◽  
J. F. G. Vliegenthart ◽  
J. Boldingh
Keyword(s):  
Fatty Acids ◽  
Linoleic Acid ◽  
Carbonyl Compounds ◽  
Dienoic Acid ◽  
Soya Bean ◽  
Linoleic Acid Hydroperoxide ◽  
Acid Hydroperoxide ◽  
Epoxy Groups ◽  
Anaerobic Reaction ◽  
Anaerobic System

In an anaerobic system soya-bean lipoxygenase catalyses in the presence of linoleic acid and l-13-hydroperoxyoctadeca-cis-9-trans-11-dienoic acid the formation of dimeric fatty acids and of carbonyl compounds. The analogous reaction does not take place when d-9-hydroperoxyoctadeca-trans-10-cis-12-dienoic acid is used instead of the 13-hydroperoxy isomer. Non-oxygenated dimers stem directly from linoleic acid and have C(11)–C(13′) or –C(9′) and C(13)–C(13′) or –C(9′) linkages. Dimers that contain oxygen originate from linoleic acid and linoleic acid hydroperoxide. It is most likely that the oxygen is present in epoxy groups.

scholarly journals The enzymic conversion of linoleic acid hydroperoxide by flax-seed hydroperoxide isomerase

1970 ◽  
Vol 120 (1) ◽  
pp. 55-60 ◽  
Author(s):  
G. A. Veldink ◽  
J. F. G. Vliegenthart ◽  
J. Boldingh
Keyword(s):  
Linoleic Acid ◽  
Functional Relationship ◽  
Dienoic Acid ◽  
Soya Bean ◽  
Isomerization Reaction ◽  
Spectroscopic Methods ◽  
Linoleic Acid Hydroperoxide ◽  
Flax Seed ◽  
Acid Hydroperoxide

1. The mode of action of flax-seed hydroperoxide isomerase was studied in vitro by using as substrates linoleic acid hydroperoxides formed by soya-bean lipoxygenase. 2. The enzyme converts only 13-hydroperoxyoctadeca-cis-9-trans-11-dienoic acid, whereas the 9-hydroperoxy isomer does not react. 3. The isomerization product was identified by chemical and spectroscopic methods as 13-hydroxy-12-oxo-octadec-cis-9-enoic acid. 4. 12,13-Epoxyoleic acid isomers do not act as intermediates in the isomerization reaction. 5. Suggestions for a functional relationship between hydroperoxide isomerase and lipoxygenase are discussed.

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.

scholarly journals The enzymic conversion of linoleic acid into 9-(nona-1′,3′-dienoxy)non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers

1972 ◽  
Vol 129 (3) ◽  
pp. 743-753 ◽  
Author(s):  
T. Galliard ◽  
D. R. Phillips
Keyword(s):  
Solanum Tuberosum ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Fatty Acid Derivative ◽  
Dienoic Acid ◽  
Enoic Acid ◽  
Ph Optimum ◽  
Ether Derivative ◽  
Unsaturated Ether ◽  
Acid Hydroperoxide

1. A major component of the lipids in aqueous (pH7.5) homogenates of tuber tissue from Solanum tuberosum was isolated and characterized as 9-(nona-1′,3′-dienoxy)non-8-enoic acid. 2. This novel unsaturated ether fatty acid derivative, which contains a butadienylvinyl ether function, has the structure: [Formula: see text] and is formed from linoleic acid by a sequence of enzymic reactions. 3. A precursor of the unsaturated ether derivative is 9-d-hydroperoxyoctadeca-10,12-dienoic acid, formed by the action of S. tuberosum lipoxygenase on linoleic acid. 4. An enzyme that converts the fatty acid hydroperoxide into the unsaturated ether derivative was isolated from S. tuberosum. The pH optimum of this enzyme is approx. 9, although the overall conversion of linoleic acid into the ether derivative is maximal at pH7.5. 5. An unusual feature of this pathway is the insertion of an oxygen atom into the alkyl chain of a fatty acid. 6. This novel mechanism may play a role in the breakdown of polyunsaturated fatty acids to volatile products in plants.

Purification and Some Properties of Potato Tuber Lipoxygenase and Detection of Linoleic Acid Radical in the Enzyme Reaction

1977 ◽  
Vol 41 (5) ◽  
pp. 827-832 ◽  
Author(s):  
Jiro Sekiya ◽  
Hitoshi Aoshima ◽  
Tadahiko Kajiwara ◽  
Tamotsu Togo ◽  
Akikazu Hatanaka
Keyword(s):  
Linoleic Acid ◽  
Potato Tuber ◽  
Enzyme Reaction ◽  
Acid Radical

scholarly journals Purification and some properties of potato tuber lipoxygenase and detection of linoleic acid radical in the enzyme reaction.

1977 ◽  
Vol 41 (5) ◽  
pp. 827-832 ◽  
Author(s):  
Jiro SEKIYA ◽  
Hitoshi AOSHIMA ◽  
Tadahiko KAJIWARA ◽  
Tamotsu TOGO ◽  
Akikazu HATANAKA
Keyword(s):  
Linoleic Acid ◽  
Potato Tuber ◽  
Enzyme Reaction ◽  
Acid Radical
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