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 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 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 Interaction between Mitochondrial Cytochromes and Linoleic Acid Hydroperoxide

1982 ◽  
Vol 69 (6) ◽  
pp. 1308-1314 ◽  
Author(s):  
Jacques Dupont ◽  
Pierre Rustin ◽  
Claude Lance
Keyword(s):  
Linoleic Acid ◽  
Linoleic Acid Hydroperoxide ◽  
Acid Hydroperoxide ◽  
Mitochondrial Cytochromes

scholarly journals Flavonoids Suppress the Cytotoxicity of Linoleic Acid Hydroperoxide toward PC12 Cells

2002 ◽  
Vol 25 (8) ◽  
pp. 1093-1096 ◽  
Author(s):  
Naoko Sasaki ◽  
Takeshi Toda ◽  
Takao Kaneko ◽  
Naomichi Baba ◽  
Mitsuyoshi Matsuo
Keyword(s):  
Linoleic Acid ◽  
Pc12 Cells ◽  
Linoleic Acid Hydroperoxide ◽  
Acid Hydroperoxide
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