Journal ArticleDOI
A new reaction of unsaturated fatty acid hydroperoxides: Formation of 11-hydroxy-12,13-epoxy-9-octadecenoic acid from 13-hydroperoxy-9,11-octadecadienoic acid
Mats Hamberg,Birgitta Gotthammar +1 more
Reads0
Chats0
TLDR
One of the main compounds formed from 13L-hydroperoxy-9cis,11trans-octadecadienoic acid anaerobically at 100 C in aqueous ethanol was found to bethreo-11-hydroxy-12,13-epoxy-nine-decadecenoic acid.Abstract:
One of the main compounds formed from 13L-hydroperoxy-9cis,11trans-octadecadienoic acid anaerobically at 100 C in aqueous ethanol was found to bethreo-11-hydroxy-12,13-epoxy-9-octadecenoic acid. The major part (ca. 90%) of this compound was formed from the fatty acid hydroperoxide in a reaction involvingcis-addition to the Δ11 double bond of the proximally linked hydroperoxide oxygen and hydroxyl ion or hydroxyl radical from the solvent. A small part (ca. 10%) was formed bycis-addition of the two hydroperoxide oxygens to the Δ11 double bond. 11-Hydroxy-12,13-epoxy-9-octadecenoic acid and its isomer, tentatively identified as 11-hydroxy-9,10-epoxy-12-octadecenoic acid, also were isolated from a sample of autoxidized linoleic acid.read more
Citations
More filters
Journal ArticleDOI
Oxygen radical chemistry of polyunsaturated fatty acids
TL;DR: Although homolytic reactions of PUFA hydroperoxides have received the most attention, hydroper oxides are also susceptible to heterolytic transformations, such as nucleophilic displacement and acid-catalyzed rearrangement.
Journal ArticleDOI
Chemistry of free radical and singlet oxidation of lipids
TL;DR: Structural studies of primary and secondary products of lipid oxidation are reviewed, further elucidating the structures of complex volatile and non-volatile decomposition products and in the mechanistic pathways for their formation.
Journal ArticleDOI
Allene oxide cyclase dependence of the wound response and vascular bundle-specific generation of jasmonates in tomato - amplification in wound signalling.
Irene Stenzel,Bettina Hause,Helmut Maucher,Andrea Pitzschke,Otto Miersch,Jörg Ziegler,Clarence A. Ryan,Claus Wasternack +7 more
TL;DR: The activation of systemin-dependent AOC and JA biosynthesis occurring only upon substrate generation and the tissue-specific generation of JA suggest an amplification in the wound response of tomato leaves allowing local and rapid defense responses.
Journal ArticleDOI
Linoleic acid peroxidation--the dominant lipid peroxidation process in low density lipoprotein--and its relationship to chronic diseases.
TL;DR: Modern separation and identification methods enable detailed insight in lipid peroxidation (LPO) processes and it is shown that HODEs, derived from LA, hydroxyoctadecadienoic acids (HODEs), surmount other markers of LPO.
Journal ArticleDOI
Allene oxide synthases of barley (Hordeum vulgare cv. Salome) : tissue specific regulation in seedling development
TL;DR: The properties of both barley AOSs, their up-regulation of their mRNAs and their tissue specific expression suggest a role during seedling development and jasmonate biosynthesis.
References
More filters
Journal ArticleDOI
On the Specificity of the Oxygenation of Unsaturated Fatty Acids Catalyzed by Soybean Lipoxidase
Mats Hamberg,Bengt Samuelsson +1 more
TL;DR: The conversion of [13l-3H, 3-14C]8,11,14-eicosatrienoic acid is accompanied by an isotope effect, suggesting that the hydrogen removal occurs as the initial step of the reaction, and only the hydrogen of the l configuration is removed by the enzyme during the conversion.
Journal ArticleDOI
Steric analysis of hydroperoxides formed by lipoxygenase oxygenation of linoleic acid.
TL;DR: Gas-liquid chromatography allowed separation of the diastereoisomeric derivatives and thus provided a sensitive means for determination of the absolute configuration of the parent unsaturated hydroxy ester.
Journal ArticleDOI
Determination of double bond position in monounsaturated fatty acid esters by mass spectrometry of their trimethylsilyloxy derivatives
Pompeo. Capella,C. M. Zorzut +1 more
Journal ArticleDOI
Enzymatic oxidations of linoleic acid and glycerol-1-monolinoleate in doughs and flour-water suspensions
TL;DR: In this paper, the products formed by enzymatic oxidations of linoleic acid and glycerol-1-monolinoleate, and the products of these oxidations in flour-water suspensions and doughs were studied.