87984-82-5Relevant academic research and scientific papers
Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA
Liu, Miao,Chen, Ping,Vericel, Evelyne,Lelli, Moreno,Beguin, Laetitia,Lagarde, Michel,Guichardant, Michel
, p. 2083 - 2094 (2013)
We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E , Z , E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from α-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10 E ,12 E ,14 E -octadecatrienoic acid, 9(S),16(S)-dihydroxy-10 E ,12 E ,14 E -octadecatrienoic acid, 9(S),16(S)-dihydroxy-10 E ,12 Z ,14 E -octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10 E ,12 Z ,14 E -octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX. Copyright
Regiospecificity of a novel bacterial lipoxygenase from Myxococcus xanthus for polyunsaturated fatty acids
An, Jung-Ung,Hong, Seung-Hye,Oh, Deok-Kun
, p. 823 - 833 (2018/05/14)
Lipoxygenase (LOX) is the key enzyme involved in the synthesis of oxylipins as signaling compounds that are important for cell growth and development, inflammation, and pathogenesis in various organisms. The regiospecificity of LOX from Myxococcus xanthus, a gram-negative bacterium, was investigated. The enzyme catalyzed oxygenation at the n-9 position in C20 and C22 polyunsaturated fatty acids (PUFAs) to form 12S- and 14S-hydroxy fatty acids (HFAs), respectively, and oxygenation at the n-6 position in C18 PUFAs to form 13-HFAs. The 12S-form products of C20 and C22 PUFAs by M. xanthus LOX is the first report of bacterial LOXs. The residues involved in regiospecificity were determined to be Thr397, Ala461, and Ile664 by analyzing amino acid alignment and a homology model based on human arachidonate 15-LOX with a sequence identity of 25%. Among these variants, the regiospecificity of the T397Y variant for C20 and C22 PUFAs was changed. This may be because of the reduced size of the substrate-binding pocket by substitution of the smaller Thr to the larger Tyr residue. The T397Y variant catalyzed oxygenation at the n-6 position in C20 and C22 PUFAs to form 15- and 17-hydroperoxy fatty acids, respectively. However, the oxygenation position of T397Y for C18 PUFAs was not changed. The discovery of bacterial LOX with novel regiospecificity will facilitate the biosynthesis of regiospecific?oxygenated signaling compounds.
Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
Anterola, Aldwin,G?bel, Cornelia,Hornung, Ellen,Sellhorn, George,Feussner, Ivo,Grimes, Howard
experimental part, p. 40 - 52 (2009/07/11)
Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 α-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering p
Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus
Schulz, Stefan,Yildizhan, Selma,Stritzke, Katja,Estrada, Catalina,Gilbert, Lawrence E.
, p. 3434 - 3441 (2008/09/19)
The four major components present in scent gland extracts of the male Costa Rica longwing butterflies Heliconius cydno and Heliconius pachinus were identified as 12- and 14-membered macrolides containing a C18-carbon skeleton. By use of micro-reactions and spectrometric examinations, structural proposals were made and subsequently proven by synthesis, using ring-closing-metathesis as the key steps. These macrolides, (9Z,11E,13S)- octadeca-9,11-dien-13-olide (5, S-coriolide), (9Z,11E,13S,15Z)-octadeca-9,11,15- trien-13-olide (6), (9Z,13S)-octadec-9-en-13-olide (13), and (9Z,11S)-octadec-9-en-11-olide (25), are biosynthetically obviously derived from oleic, linoleic, and linolenic acids. Their absolute configurations were determined by gas chromatographic investigations on chiral phases, showing all to possess (S)-configuration. The Royal Society of Chemistry.
Efficient syntheses of (10E,12Z,15Z)-9-oxo- and (9Z,11E,15E)-13-oxo-octadecatrienoic acids; two stress metabolites of wounded plants
Koch, Thomas,Hoskovec, Michal,Boland, Wilhelm
, p. 3271 - 3274 (2007/10/03)
Configurationally pure 9-oxo-10E,12Z,15Z- and 13-oxo-9Z,11E,15E-octadecatrienoic acid are available from linolenic acid via regioselective functionalisation using lipoxygenases from soybean or tomato at specific pH conditions. Reduction of the resulting hydroperoxides followed by oxidation of the resulting allylic alcohols with Bobbitt's reagent yields the configurationally pure but labile ketotrienoic acids 4 and 5 without concomitant isomerisation.
Oxidation of Octadecatrienoic Acids in the Red Alga Lithothamnion corallioides: Structural and Stereochemical Studies of Conjugated Tetraene Fatty Acids and Bis Allylic Hydroxy Acids
Hamberg, Mats
, p. 3065 - 3072 (2007/10/02)
Enzymatic oxidation of (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid (γ-linolenic acid; 1a) in a preparation of the red alga Lithothamnion corallioides Crouan led to the formation of (6Z,8E,10E,12Z)-octadeca-6,8,10,12-tetraenoic acid 2a and (11R,6Z,9Z,12Z)-hydroxyoctadeca-6,9,12-trienoic acid 3a as the main products. (9Z,12Z,15Z)-Octadeca-(9,12,15)-trienoic acid (α-linolenic acid; 4a) was oxidized in an analogous way to yield (9Z,11E,13E,15Z)-octadeca-9,11,13,15-tetraenoic acid (α-parinaric acid; 5a), (11S,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid 6a, and (14R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid 7a.Isotope studies demonstrated that enzymatic conversion of the acid 1a into the tetraene 2a was accompanied by stereospecific eliminations of the pro-S and pro-R hydrogens from C-8 and C-11, respectively.The bis-allylic hydroxy acid 3a was formed from acid 1a by a reaction involving stereospecific elimination of the pro-S hydrogen from C-11 and incorporation of 1 atom of oxygen from water in the C-11 hydroxy group.Although the bis allylic hydroxy esters 3b, 6b, and 7b were chemically convertible into conjugated tetraenes by rapid acid-catalysed dehydration, enzymatic formation of conjugated tetraenes and hydroxy acids in Lithothamnion occured by independent pathways.
Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids: Selfdefensive substances against rice blast disease
Yadav,Deshpande,Sharma
, p. 4465 - 4474 (2007/10/02)
A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd°-CuI catalysed coupling of (S )-halovinylalcohol with acetylenic moiety is described. The required optically pure chlor
