Synthesis, Discovery, and Quantitation of Dihomo‐Isofurans: Biomarkers for In Vivo Adrenic Acid Peroxidation

Torre, Aurélien de la; Lee, Yiu Yiu; Oger, Camille; Sangild, Per Torp; Durand, Thierry; Lee, Jetty Chung‐Yung; Galano, Jean‐Marie

doi:10.1002/anie.201402440

Cited by 44 publications

(54 citation statements)

References 24 publications

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“…Furthermore, in our previous report [9] we have shown the measurement of dihomo-IsoF, 17(RS)-10-epi-SC-D 15 -11dihomo-IsoF 3 in prefrontal cortex of preterm pig brain and it is unknown if the second type 7(RS)-ST-D 8 -11-dihomo-IsoF 1, as shown in the strategy herein, is measurable in biological samples. Furthermore, in our previous report [9] we have shown the measurement of dihomo-IsoF, 17(RS)-10-epi-SC-D 15 -11dihomo-IsoF 3 in prefrontal cortex of preterm pig brain and it is unknown if the second type 7(RS)-ST-D 8 -11-dihomo-IsoF 1, as shown in the strategy herein, is measurable in biological samples.…”

Section: Resultsmentioning

confidence: 65%

“…[7] Therefore, great potential is embedded into NeuroFs as complementary biomarkers of neuronal oxidative stress, especially in oxygen-tension associated pathologies. [9] Besides being potential biomarkers, such metabolites could provide pharmacological properties yet to be discovered. We previously highlighted that dihomo-isoprostanes were early biomarkers in Rett syndrome disorder, [8] and that one type of dihomo-IsoFs was indeed highly elevated in preterm pig brain.…”

Section: Introductionmentioning

confidence: 99%

“…Six syntheses of furanic oxy-genated metabolites of PUFAs have been described to date. [9] To unify this strategy a 5-endo cyclization mode would lead to enediol isofuran 1 and neurofuran 2. [10][11][12] More recently, Zanoni and co-workers used Trost asymmetric allylic alkylation for the synthesis of an alkenyl-NeuroF.…”

Section: Introductionmentioning

confidence: 99%

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Total Syntheses and In Vivo Quantitation of Novel Neurofuran and Dihomo‐isofuran Derived from Docosahexaenoic Acid and Adrenic Acid

Torre

Lee

Mazzoni

et al. 2014

Chemistry A European J

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Neurofurans (NeuroFs) and dihomo-isofurans (dihomo-IsoFs) are produced in vivo by non-enzymatic free-radical pathways from docosahexaenoic and adrenic acids, respectively. As these metabolites are produced in minute amounts, their analyses in biological samples remain challenging. Syntheses of neurofuran and dihomo-isofurans described are based on a pivotal strategy, thanks to an enantiomerically enriched intermediate, which allowed, for the first time, access to both families: the alkenyl and enediol. Owing to this formation, quantitation of specific NeuroF and dihomo-IsoFs in biological samples was attainable.

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Section: Resultsmentioning

confidence: 65%

Section: Introductionmentioning

confidence: 99%

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Total Syntheses and In Vivo Quantitation of Novel Neurofuran and Dihomo‐isofuran Derived from Docosahexaenoic Acid and Adrenic Acid

Torre

Lee

Mazzoni

et al. 2014

Chemistry A European J

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“…Oxidative stress and reactive oxygen species can lead to free-radical catalyzed peroxidation of PUFA, generating a range of isoP and a multitude of hydroxy fatty acids [31–35]. In contrast to enzymatic oxygenation of PUFA, which leads to the formation of pure oxygenated enantiomers and regioisomers, lack of enzymatic control in the free-radical-mediated chemical reactions results in a racemic mixtures of stereo- and regio-isomers.…”

Section: Biosynthesis Of Oxygenated Lipid Mediatorsmentioning

confidence: 99%

Targeted lipidomic strategies for oxygenated metabolites of polyunsaturated fatty acids

Astarita

Kendall

Dennis

et al. 2015

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

121

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Oxidation of polyunsaturated fatty acids (PUFA) through enzymatic or non-enzymatic free radical-mediated reactions can yield an array of lipid metabolites including eicosanoids, octadecanoids, docosanoids and related species. In mammals, these oxygenated PUFA mediators play prominent roles in the physiological and pathological regulation of many key biological processes in the cardiovascular, renal, reproductive and other systems including their pivotal contribution to inflammation. Mass spectrometry-based technology platforms have revolutionized our ability to analyze the complex mixture of lipid mediators found in biological samples, with increased numbers of metabolites that can be simultaneously quantified from a single sample in few analytical steps. The recent development of high-sensitivity and high-throughput analytical tools for lipid mediators affords a broader view of these oxygenated PUFA species, and facilitates research into their role in health and disease. In this review, we illustrate current analytical approaches for a high-throughput lipidomic analysis of eicosanoids and related mediators in biological samples.

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“…79 Later, the group of She used Borhan cyclization procedure for the total synthesis of (+)-monocerin. 80 More recently, the group of Galano-Oger applied it for the syntheses of dihomoisofurans and neurofuran (Scheme 26), 81,82 in a divergent strategy using 5-exo-tet and 5-endotet cyclizations. Few protecting groups have been carried through the cyclization conditions using Lewis acid.…”

Section: Scheme 25: Thf Formation By Reductive Cyclizationmentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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Synthesis, Discovery, and Quantitation of Dihomo‐Isofurans: Biomarkers for In Vivo Adrenic Acid Peroxidation

Cited by 44 publications

References 24 publications

Total Syntheses and In Vivo Quantitation of Novel Neurofuran and Dihomo‐isofuran Derived from Docosahexaenoic Acid and Adrenic Acid

Total Syntheses and In Vivo Quantitation of Novel Neurofuran and Dihomo‐isofuran Derived from Docosahexaenoic Acid and Adrenic Acid

Targeted lipidomic strategies for oxygenated metabolites of polyunsaturated fatty acids

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

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