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Etheroleic Acid Sale

目录号 : GC49778

A divinyl ether oxylipin

Etheroleic Acid Chemical Structure

Cas No.:169217-38-3

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25 µg
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50 µg
¥4,378.00
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产品描述

Etheroleic acid is a divinyl ether oxylipin.1,2 It is a metabolite of linolenic acid that is formed in plants via 13-lipoxygenase-mediated formation of 13(S)-HpODE or (±)13-HpODE followed by conversion to the divinyl ether by divinyl ether synthase. Etheroleic acid (30 µM) is fungicidal against the powdery mildew B. graminis on the second leaves of barley seedlings.3

1.Grechkin, A.N., Ilyasov, A.V., and Hamberg, M.On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbsEur. J. Biochem.245(1)137-142(1997) 2.Hamberg, M.Biosynthesis of new divinyl ether oxylipins in Ranunculus plantsLipids37(4)427-433(2002) 3.Cowley, T., and Walters, D.Local and systemic effects of oxylipins on powdery mildew infection in barleyPest Manag. Sci.61(6)572-576(2005)

Chemical Properties

Cas No. 169217-38-3 SDF Download SDF
Canonical SMILES CCCC/C=C/O/C=C/C=C\CCCCCCCC(O)=O
分子式 C18H30O3 分子量 294.4
溶解度 Ethanol: soluble 储存条件 -20°C
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1 mM 3.3967 mL 16.9837 mL 33.9674 mL
5 mM 0.6793 mL 3.3967 mL 6.7935 mL
10 mM 0.3397 mL 1.6984 mL 3.3967 mL
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Research Update

Oxylipins in the spikemoss Selaginella martensii: Detection of divinyl ethers, 12-oxophytodienoic acid and related cyclopentenones

Phytochemistry 2015 Oct;118:42-50.PMID:26277770DOI:10.1016/j.phytochem.2015.08.003.

Green tissues of spikemoss Selaginella martensii Spring possessed the complex oxylipins patterns. Major oxylipins were the products of linoleic and α-linolenic acids metabolism via the sequential action of 13-lipoxygenase and divinyl ether synthase (DES) or allene oxide synthase (AOS). AOS products were represented by 12-oxophytodienoic acid (12-oxo-PDA) isomers. Exceptionally, S. martensii possesses high level of 12-oxo-9(13),15-PDA, which is very uncommon in flowering plants. Separate divinyl ethers were purified after micro-preparative incubations of linoleic or α-linolenic acids with homogenate of S. martensii aerial parts. The NMR data allowed us to identify all geometric isomers of divinyl ethers. Linoleic acid was converted to divinyl ethers Etheroleic Acid, (11Z)-etheroleic acid and a minority of (ω5Z)-etheroleic acid. With α-linolenate precursor, the specificity of divinyl ether biosynthesis was distinct. Etherolenic and (ω5Z)-etherolenic acids were the prevailing products while (11Z)-etherolenic acid was a minor one. Divinyl ethers are detected first time in non-flowering land plant. These are the first observations of fatty acid metabolism through the lipoxygenase pathway in spikemosses (Lycopodiophyta).

Separation of divinyl ether fatty acid isomers by micellar electrokinetic chromatography

Electrophoresis 2001 Apr;22(6):1163-9.PMID:11358142DOI:10.1002/1522-2683()22:6<1163::AID-ELPS1163>3.0.CO;2-M.

A micellar electrokinetic chromatography (MEKC) method has been developed for the direct resolution of divinyl ether type of hydrophobic fatty acid isomers. The fatty acid isomers resolved include colneleic acid (CL), colnelenic acid (CLn), 14(Z)-etheroleic acid (14(Z)-EL), 14(Z)-etherolenic acid (14(Z)-Eln), 11(Z)-etheroleic acid (11(Z)-EL), 11(Z)-etherolenic acid (11(Z)-Eln), Etheroleic Acid (EL) and etherolenic acid (Eln). These fatty acid isomers differ in number, position and spatial arrangement of the double bonds and the position of the ether oxygen. A central composite design was employed for the optimization of the key variables of the separation, namely the concentrations of sodium dodecyl sulfate (SDS) and organic modifiers. The use of micelles combined with an organic modifier in the background electrolyte made it possible to dissolve and separate relatively hydrophobic fatty acid isomers, and to achieve high separation efficiency. Using heptakis-(2,3-dimethyl-6-sulfato)-beta-cyclodextrin (HDMS-beta-CD) as a buffer additive, complete separation of the examined eight divinyl ethers was achieved. Separation efficiencies up to 5 x 10(5) theoretical plates/m were achieved under optimized conditions. Direct UV was applied for detection of the fatty acids. The results were compared with those obtained from high-performance liquid chromatography (HPLC) separation.

Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids

FEBS J 2005 Feb;272(3):736-43.PMID:15670154DOI:10.1111/j.1742-4658.2004.04510.x.

Incubations of [8(R)-2H]9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid, [14(R)-2H]13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid and [14(S)-2H]13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid were performed with preparations of plant tissues containing divinyl ether synthases. In agreement with previous studies, generation of colneleic acid from the 8(R)-deuterated 9(S)-hydroperoxide was accompanied by loss of most of the deuterium label (retention, 8%), however, the opposite result (98% retention) was observed in the generation of 8(Z)-colneleic acid from the same hydroperoxide. Formation of Etheroleic Acid and 11(Z)-etheroleic acid from the 14(R)-deuterated 13(S)-hydroperoxide was accompanied by loss of most of the deuterium (retention, 7-8%), and, as expected, biosynthesis of these divinyl ethers from the corresponding 14(S)-deuterated hydroperoxide was accompanied by retention of deuterium (retention, 94-98%). Biosynthesis of omega5(Z)-etheroleic acid from the 14(R)- and 14(S)-deuterated 13(S)-hydroperoxides showed the opposite results, i.e. 98% retention and 4% retention, respectively. The experiments demonstrated that biosynthesis of divinyl ether fatty acids from linoleic acid 9- and 13-hydroperoxides takes place by a mechanism that involves stereospecific abstraction of one of the two hydrogen atoms alpha to the hydroperoxide carbon. Furthermore, a consistent relationship between the absolute configuration of the hydrogen atom eliminated (R or S) and the configuration of the introduced vinyl ether double bond (E or Z) emerged from these results. Thus, irrespective of which hydroperoxide regioisomer served as the substrate, divinyl ether synthases abstracting the pro-R hydrogen generated divinyl ethers having an E vinyl ether double bond, whereas enzymes abstracting the pro-S hydrogen produced divinyl ethers having a Z vinyl ether double bond.

Local and systemic effects of oxylipins on powdery mildew infection in barley

Pest Manag Sci 2005 Jun;61(6):572-6.PMID:15668923DOI:10.1002/ps.1026.

Treatment of the first leaves of barley seedlings with the oxylipin colneleic acid, or the two trihydroxy oxylipins 9,12,13-trihydroxy-11(E)-octadecenoic acid and 9,12,13-trihydroxy-10(E)-octadecenoic acid, reduced infection of that leaf by the powdery mildew fungus Blumeria graminis Speer f sp hordei Marchal. When applied to first leaves, Etheroleic Acid and colneleic acid, as well as the trihydroxy oxylipin 9,12,13-trihydroxy-10(E),15(Z)-octadecadienoic acid, also reduced mildew infection in second leaves. In all cases where local and systemic effects against mildew were observed, activity of the defence-related enzyme phenylalanine ammonia lyase (PAL) was increased, but only following challenge inoculation with powdery mildew. Peroxidase activity was not affected by oxylipin treatment or mildew inoculation. Whether the effects observed were due to the oxylipins or to breakdown products is not known, since no information is available on the stability of these particular oxylipins on leaf surfaces. Nevertheless, these data represent the first report of systemic effects against pathogen infection following pre-treatment with oxylipins.

Divinyl ether synthesis in garlic bulbs

J Exp Bot 2008;59(4):907-15.PMID:18326559DOI:10.1093/jxb/ern010.

Formation of 13-lipoxygenase-derived divinyl ethers has been described in garlic bulbs. Here, the identification of a cDNA from garlic is described, which encodes for an enzyme that corresponds to divinyl ether synthases (DES). The recombinant protein was expressed in Escherichia coli and shown to metabolize 13-hydroperoxy as well as 9-hydroperoxy linole(n)ic acid to etherole(n)ic and colnele(n)ic acid, respectively. This biochemical feature classifies it as a member of the CYP74C subfamily of cytochrome P-450 enzymes. Product analysis after incubation of purified recombinant enzyme and fatty acid hydroperoxides revealed the formation of a mixture of different cis/trans isomers with one isomer often dominant. RNA blot analyses showed a constitutive expression of DES transcripts predominant in below-ground organs of garlic. By exogenous application of salicylic acid and sorbitol, but not by methyljasmonate, the transcript was also induced in leaves. Whereas the prominent divinyl ether in garlic was the 13-lipoxygenase-derived Etheroleic Acid, analysis of transgenic Arabidopsis expressing garlic DES showed that 9-lipoxygenase-derived colnelenic acid dominated 24 h after wounding. These data indicate that the product pattern of this DES from garlic depends on the substrate availability and that the enzyme is the first member in the group of 9/13-DES.