Improved enantioselective analysis of polyunsaturated hydroxy fatty acids in psoriatic skin scales using high-performance liquid chromatography

Bayer, Mathias; Mosandl, Armin; Thaçi, Diamant

doi:10.1016/j.jchromb.2005.02.008

Cited by 28 publications

(24 citation statements)

References 14 publications

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“…Therefore, chiral chromatography was used for assigning chirality. Order of elution of R-and S-isomers on chiral columns is the same for similar hydroxylated LC-PUFA compounds when the same chromatographic conditions are used (40,41). In this case, the 17-HDHA racemate mixture and (17S)-HDHA was used to ascertain the order of elution.…”

Section: Products Formed Upon Reaction Of Fatty Acids With 5- 12- Amentioning

confidence: 99%

Biogenic Synthesis, Purification, and Chemical Characterization of Anti-inflammatory Resolvins Derived from Docosapentaenoic Acid (DPAn-6)

Dangi¹,

Obeng²,

Nauroth³

et al. 2009

Journal of Biological Chemistry

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Chem. 278, 14677-14687). Our objective was to determine whether similar derivatives are enzymatically synthesized from other C-22 fatty acids and whether these molecules possess inflammation resolution properties. The reaction of DHA, DPAn-3, and DPAn-6 with 5-, 12-, and 15-lipoxygenases produced oxylipins, which were identified and characterized by liquid chromatography coupled with tandem mass-spectrometry. DPAn-6 and DPAn-3 proved to be good substrates for 15-lipoxygenase. 15-Lipoxygenase proved to be the most efficient enzyme of the three tested for conversion of long chain polyunsaturated fatty acids to corresponding oxylipins. Since DPAn-6 is a major component of Martek DHA-S TM oil, we focused our attention on reaction products obtained from the DPAn-6 and 15-lipoxygenase reaction. (17S)-hydroxy-DPAn-6 and (10,17S)-dihydroxy-DPAn-6 were the main products of this reaction. These compounds were purified by preparatory high performance liquid chromatography techniques and further characterized by NMR, UV spectrophotometry, and tandem mass spectrometry. We tested both compounds in two animal models of acute inflammation and demonstrated that both compounds are potent anti-inflammatory agents that are active on local intravenous as well as oral administration. These oxygenated DPAn-6 compounds can thus be categorized as a new class of DPAn-6-derived resolvins.

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Section: Products Formed Upon Reaction Of Fatty Acids With 5- 12- Amentioning

confidence: 99%

Biogenic Synthesis, Purification, and Chemical Characterization of Anti-inflammatory Resolvins Derived from Docosapentaenoic Acid (DPAn-6)

Dangi¹,

Obeng²,

Nauroth³

et al. 2009

Journal of Biological Chemistry

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show abstract

“…Enantiomeric separation of cis-trans conjugated hydroxyeicosatetraenoic and hydroxyoctadecadienoic methyl esters was first reported on columns with dinitrobenzoyl ␣-phenylglycine [13]. At the same time, a series of chiral columns were developed based on a matrices with derivatized amylose or cellulose (e.g., Chiralpak and Chiralcel series 1 ), and used for steric analysis of cis-trans conjugated hydroxy fatty acids [7,[14][15][16]. There is less information on separation of hydroperoxy fatty acids.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation and analysis of unsaturated hydroperoxy fatty acids by chiral column chromatography-mass spectrometry

Garscha

Nilsson

Oliw

2008

Journal of Chromatography B

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“…1G ) is racemic 12-HETE. A separation of 12(R)-and 12(S)-HETE could only be achieved with chiral chromatography (runtimes from 10 to 60 min) ( 24,45 ). The major isomer present in human urine might be 12(S)-HETE ( 24,33 ).…”

Section: Discussionmentioning

confidence: 99%

A simple and robust UPLC-SRM/MS method to quantify urinary eicosanoids

Sterz

Scherer

Ecker

2012

Journal of Lipid Research

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Improved enantioselective analysis of polyunsaturated hydroxy fatty acids in psoriatic skin scales using high-performance liquid chromatography

Cited by 28 publications

References 14 publications

Biogenic Synthesis, Purification, and Chemical Characterization of Anti-inflammatory Resolvins Derived from Docosapentaenoic Acid (DPAn-6)

Biogenic Synthesis, Purification, and Chemical Characterization of Anti-inflammatory Resolvins Derived from Docosapentaenoic Acid (DPAn-6)

Enantiomeric separation and analysis of unsaturated hydroperoxy fatty acids by chiral column chromatography-mass spectrometry

A simple and robust UPLC-SRM/MS method to quantify urinary eicosanoids

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