Total syntheses of four possible stereoisomers of resolvin E3

Urabe, Daisuke; Todoroki, Hidenori; Masuda, Koji; Inoue, M.

doi:10.1016/j.tet.2012.02.045

Cited by 34 publications

(22 citation statements)

References 37 publications

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“…Therefore, there is a need to synthesize these compounds with a high degree of regio-and stereospecifi city. A small number of organic synthesis methods have been published [for examples see (22)(23)(24)(25)], but these involve challenging and time-consuming multistep reactions with various stereocenters and cis/trans double bonds. The use of enzymes as biocatalysts is an attractive option to overcome the diffi culties of organic synthesis for the production of a range of known and novel lipid mediators ( 26,27 ).…”

Section: Methodsmentioning

confidence: 99%

Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase

Dobson

Barrow

Kralovec³

et al. 2013

Journal of Lipid Research

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Section: Methodsmentioning

confidence: 99%

Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase

Dobson

Barrow

Kralovec³

et al. 2013

Journal of Lipid Research

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“…Similarly, EPA is converted to 18R‐hydroxy‐EPA (18R‐HEPE) by acetylated COX‐2 (in the presence of aspirin) (16) or endogenous cytochrome P450 (in the absence of aspirin) (17). 18R‐HEPE is a key intermediate in the biosynthesis of the E‐series resolvins (RvEs) including RvE1 (5S,12R,18R‐TriHEPE) (16, 18, 19), RvE2 (5S,18R‐ DiHEPE) (20, 21), and RvE3 (17R,18R‐DiHEPE) (22‐24). LC n‐3 PUFAs are also effective substrates for the less well‐characterized cytochrome P450 (CYP) epoxygenase pathway (25), and recent reports show that CYP metabolites may also contribute to LC n‐3 PUFA bioactivity (26).…”

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confidence: 99%

Divergent shifts in lipid mediator profile following supplementation with n‐3 docosapentaenoic acid and eicosapentaenoic acid

et al. 2016

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In contrast to the well-characterized effects of specialized proresolving lipid mediators (SPMs) derived from eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), little is known about the metabolic fate of the intermediary long-chain (LC) n-3 polyunsaturated fatty acid (PUFA) docosapentaenoic acid (DPA). In this double blind crossover study, shifts in circulating levels of n-3 and n-6 PUFA-derived bioactive lipid mediators were quantified by an unbiased liquid chromatography-tandem mass spectrometry lipidomic approach. Plasma was obtained from human subjects before and after 7 d of supplementation with pure n-3 DPA, n-3 EPA or placebo (olive oil). DPA supplementation increased the SPM resolvin D5 (RvD5) and maresin (MaR)-1, the DHA vicinal diol 19,20-dihydroxy-DPA and n-6 PUFA derived 15-keto-PG E (15-keto-PGE). EPA supplementation had no effect on any plasma DPA or DHA derived mediators, but markedly elevated monohydroxy-eicosapentaenoic acids (HEPEs), including the e-series resolvin (RvE) precursor 18-HEPE; effects not observed with DPA supplementation. These data show that dietary n-3 DPA and EPA have highly divergent effects on human lipid mediator profile, with no overlap in PUFA metabolites formed. The recently uncovered biologic activity of n-3 DPA docosanoids and their marked modulation by dietary DPA intake reveals a unique and specific role of n-3 DPA in human physiology.-Markworth, J. F., Kaur, G., Miller, E. G., Larsen, A. E., Sinclair, A. J., Maddipati, K. R., Cameron-Smith, D. Divergent shifts in lipid mediator profile following supplementation with n-3 docosapentaenoic acid and eicosapentaenoic acid.

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“…Recently, we established the total organic syntheses of four different stereoisomers of RvE3: (17 R ,18 R )-, (17 S ,18 S )-, (17 S ,18 R )- and (17 R ,18 S )-dihydroxy-5 Z ,8 Z ,11 Z ,13 E ,15 E -EPE. ( 23 ) Based on matching of physical and biological properties, RvE3 was assigned the complete structure 17 R ,18 R / S -dihydroxy-5 Z ,8 Z ,11 Z ,13 E ,15 E -EPE. ( 24 ) These natural isomers (i.e., 17 R ,18 S - and 17 R ,18 R -diHEPE) prepared by total organic synthesis displayed a potent anti-inflammatory action by limiting neutrophil infiltrations both in vitro and in vivo .…”

Section: Resolvin E3: a Novel Eosinophil-derived Lipid Mediator With mentioning

confidence: 99%

Identification of novel omega-3 fatty acid-derived bioactive metabolites based on a targeted lipidomics approach

Isobe

Arita

2014

J. Clin. Biochem. Nutr.

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Omega-3 polyunsaturated fatty acids such as eicosapentaenoic acid and docosahexaenoic acid have beneficial effects in many inflammatory disorders. Although the mechanism of eicosapentaenoic acid and docosahexaenoic acid action is still not fully defined in molecular terms, recent studies have revealed that, during the course of acute inflammation, omega-3 polyunsaturated fatty acid-derived anti-inflammatory mediators including resolvins and protectins are produced. This review presents recent advances in understanding the formation and action of these mediators, especially focusing on the LC-MS/MS-based lipidomics approach and recently identified bioactive products with potent anti-inflammatory property.

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Total syntheses of four possible stereoisomers of resolvin E3

Cited by 34 publications

References 37 publications

Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase

Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase

Divergent shifts in lipid mediator profile following supplementation with n‐3 docosapentaenoic acid and eicosapentaenoic acid

Identification of novel omega-3 fatty acid-derived bioactive metabolites based on a targeted lipidomics approach

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