ChemInform Abstract: Recent Approaches to the Total Synthesis of Phytoprostanes, Isoprostanes and Neuroprostanes as Important Products of Lipid Oxidative Stress and Biomarkers of Disease

Jahn, Emanuela; Galano, Jean‐Marie; Jahn, Ullrich

doi:10.1002/chin.201433243

Cited by 7 publications

(8 citation statements)

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“…Pure isoprostanoid sources are needed to better evaluate their role in lipid biology. Through total synthesis, research on isoprostanoids has been significantly advanced in the last decade [25,26].…”

Section: The Use Of Organic Synthesis To Acquire Isoprostanoid Standardsmentioning

confidence: 99%

Isoprostanes, neuroprostanes and phytoprostanes: An overview of 25 years of research in chemistry and biology

Galano

Lee

Oger

et al. 2017

Progress in Lipid Research

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Since the beginning of the 1990's diverse types of metabolites originating from polyunsaturated fatty acids, formed under autooxidative conditions were discovered. Known as prostaglandin isomers (or isoprostanoids) originating from arachidonic acid, neuroprostanes from docosahexaenoic acid, and phytoprostanes from α-linolenic acid proved to be prevalent in biology. The syntheses of these compounds by organic chemists and the development of sophisticated mass spectrometry methods has boosted our understanding of the isoprostanoid biology. In recent years, it has become accepted that these molecules not only serve as markers of oxidative damage but also exhibit a wide range of bioactivities. In addition, isoprostanoids have emerged as indicators of oxidative stress in humans and their environment. This review explores in detail the isoprostanoid chemistry and biology that has been achieved in the past three decades.

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Section: The Use Of Organic Synthesis To Acquire Isoprostanoid Standardsmentioning

confidence: 99%

Isoprostanes, neuroprostanes and phytoprostanes: An overview of 25 years of research in chemistry and biology

Galano

Lee

Oger

et al. 2017

Progress in Lipid Research

Self Cite

144

153

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“…Since the discovery of PhytoPs in 1998 8 more than ten total syntheses of individual PhytoPs have been published. 6,33,34 Diversity oriented syntheses of PhytoPs are especially attractive for many biological investigations. So far, such approaches aimed at accessing the different diastereomers or side chain isomers for a given ring substitution pattern.…”

Section: Introductionmentioning

confidence: 99%

Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017

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A unified strategy for the total synthesis of the methyl esters of all phytoprostane (PhytoP) classes bearing two ring-oxygen atoms based on an orthogonally protected common precursor is described. Racemic 16-F-, 16-E-PhytoP and their C-16 epimers, which also occur as racemates in Nature, were successfully obtained. The first total synthesis of very sensitive 16-D-PhytoP succeeded, however, it quickly isomerized to more stable, but so far also unknown Δ-16-D-PhytoP, which may serve as a more reliable biomarker for D-type PhytoP. The dioxygenated cyclopentane ring carrying the ω-chain with the oxygen functionality in the 16-position was approached by a radical oxidative cyclization mediated by ferrocenium hexafluorophosphate and TEMPO. The α-chain was introduced by a new copper-catalyzed alkyl-alkyl coupling of a 6-heptenyl Grignard reagent with a functionalized cyclopentylmethyl triflate.

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“…Although there is little information about the biological effects of PhytoPs, it is known that free PhytoPs are the only prostanes able to be absorbed by humans . They have been identified in urine and found esterified to lipids in the plasma of healthy men consuming vegetable oil, with some evidence that they can modulate the function of the immune and vascular systems . Despite the fact that most olive orchards in the Mediterranean area have been traditionally grown under rain‐fed conditions, it has been demonstrated that irrigation is a vital practice in improving both olive production and productivity .…”

Section: Introductionmentioning

confidence: 99%

“…13 They have been identified in urine and found esterified to lipids in the plasma of healthy men consuming vegetable oil, 14 with some evidence that they can modulate the function of the immune and vascular systems. 15,16 Despite the fact that most olive orchards in the Mediterranean area have been traditionally grown under rain-fed conditions, it has been demonstrated that irrigation is a vital practice in improving both olive production and productivity. 17 Nevertheless, the Mediterranean coast is characterized by the aridity of the climate and the persistent shortage of water resources.…”

Section: Introductionmentioning

confidence: 99%

Effect of the season on the free phytoprostane content in Cornicabra extra virgin olive oil from deficit‐irrigated olive trees

et al. 2015

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Deficit irrigation during pit hardening or for a further period of 2 weeks thereafter to increase irrigation water saving is clearly critical for EVOO composition because of the enhancement of free PhytoPs, which have potential beneficial effects on human health. The response of individual free PhytoPs to changes in plant water status was not as perceptible as expected, preventing their use as biomarkers of water stress.

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ChemInform Abstract: Recent Approaches to the Total Synthesis of Phytoprostanes, Isoprostanes and Neuroprostanes as Important Products of Lipid Oxidative Stress and Biomarkers of Disease

Cited by 7 publications

References 0 publications

Isoprostanes, neuroprostanes and phytoprostanes: An overview of 25 years of research in chemistry and biology

Isoprostanes, neuroprostanes and phytoprostanes: An overview of 25 years of research in chemistry and biology

Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

Effect of the season on the free phytoprostane content in Cornicabra extra virgin olive oil from deficit‐irrigated olive trees

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