Payne rearrangement during analysis of epoxyalcohols of linoleic and α-linolenic acids by normal phase liquid chromatography with tandem mass spectrometry

2014

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human cells by cyclooxygenases and cytochrome P450 (CYP) to prostaglandins, thromboxanes, prostacyclin, and related compounds and by lipoxygenases to hydroperoxides, leukotrienes, and epoxy alcohols ( 3,4 ). These eicosanoids exert a plethora of both physiological and pathophysiological functions (e.g., in control of reproduction, cancer development, skin water permeability, fever, and infl ammation). Homologous enzymes are found in plants and fungi with functions in reproduction, development, and infection, and they usually use linoleic and linolenic acids as substrates ( 5-7 ).Plant lipoxygenases and allene oxide synthases (AOSs) catalyze the fi rst steps during biosynthesis of jasmonic acid, which is a potent regulator of growth and defense with structural similarities to prostaglandins ( 7,8 ). Pathogens can induce expression of lipoxygenases and fatty acid ␣ -dioxygenase (DOX) in plants with formation of jasmonic acid and other oxylipins, which act as defense molecules. Oxylipins are also formed by fungi, which are human and plant pathogens. These fungi express lipoxygenases and DOX-CYP fusion proteins ( 5 ). The DOX domains are homologs to animal heme peroxidases, which include cyclooxygenases and ␣ -DOX, and their CYP domains take advantage of the peroxide shunt pathway in analogy with thromboxane and prostacyclin synthases ( 9 ). Oxylipins designate oxygenated metabolites of unsaturated fatty acids, and they are mainly formed by eukaryotic organisms ( 1, 2 ). Arachidonic acid is oxygenated in Abstract The genome of the rice blast fungus

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Section: Crucial Amino Acid Residues Of the Eas Domain Of Mgg_10859mentioning

confidence: 99%

Epoxy alcohol synthase of the rice blast fungus represents a novel subfamily of dioxygenase-cytochrome P450 fusion enzymes

Hoffmann

Jernerén

2014

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“…NP-HPLC-MS/MS analysis showed that small amounts of erythro and threo 8(9)-epoxy-10-hydroxy-12Z-octadecenoic acids could also be detected (Fig. 2B) (31). The structure of the -ketols formed from 18:2n-6 were confirmed by reduction of the ketone to a hydroxyl group, hydrogenation of the 12Z double bond, comparison with the mass spectra of the [ 13 C 18 ]-labeled -ketol (27), and with the mass spectra of the -ketol formed from 18:1n-9.…”

Section: Expression Of Recombinant Proteinsmentioning

confidence: 99%

“…In contrast, about 50% of 9S-HPODE was transformed to an -ketol, 9-hydroxy-10-oxo-12Z-octadecenoic acid, and to erythro and threo 9S(10S)-epoxy-11-hydroxy-12Z-octadecenoic acids (supplemental Fig. S3B) [see (31)]. The relative amounts of the -ketol and the epoxy alcohols were 1:2.…”

mentioning

confidence: 99%

A new class of fatty acid allene oxide formed by the DOX-P450 fusion proteins of human and plant pathogenic fungi, C. immitis and Z. tritici

Aragó

Chen

et al. 2016

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“…The MS/MS/MS spectra of hydroperoxides are virtually identical to the MS/MS spectra of the corresponding keto fatty acids. Keto fatty acids are subject to keto-enol tautomerism, and their MS/MS spectra are more difficult to interpret than the MS/MS spectra of hydroxy fatty acids (47). The MS/MS/MS spectra of hydroperoxides formed from 16:3n-3 are summarized in Table 1.…”

Section: Ms Analysismentioning

confidence: 99%

On the singular, dual, and multiple positional specificity of manganese lipoxygenase and its G316A mutant

Cristea

2007

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