Carbocyclic oxylipins of marine origin

Gerwick, William H.

doi:10.1021/cr00021a008

Cited by 136 publications

(76 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…14 The biosynthesis of the protectin members of the SPMs involved in human physiological processes differs from other oxygenated natural products, such as the oxylipins. 37 For the latter class of natural products, lipoxygenase and allene oxide synthase are the enzymes involved in the formation of epoxy allylic cation derived intermediates. 38 In human physiological systems the biosynthesis of the protectin class of SPMs results in natural products, with a E , E , Z -triene moiety, exhibiting potent pro-resolving actions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages

et al. 2015

View full text Add to dashboard Cite

The n-3 polyunsaturated fatty acids act as substrates during the resolution phase of acute inflammation for the biosynthesis of specialized pro-resolving lipid mediators. One premier example is the C22-dihydroxy-polyunsaturated fatty acid protectin D1 (1). The human 15-lipoxygenase type I, via stereoselective processes and with docosahexaenoic acid as the substrate, enables the formation of this specialized pro-resolving lipid mediator. Herein, based on results from LC/MS-MS metabololipidomics, support is presented for the apprehended biosynthesis of 1 in human macrophages occurs via the intermediate 16S,17S-epoxy-protectin (5). Stereochemical pure 5 was obtained using the Katsuki-Sharpless epoxidation protocol, establishing the chirality at the C16 and C17 atoms, one Z-selective reduction as well as E- and Z-stereoselective Wittig reactions. In addition, information on the non-enzymatic aqueous hydrolysis products and the half-life of 16S,17S-epoxy-protectin (5) is presented.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages

et al. 2015

View full text Add to dashboard Cite

show abstract

“…4 The structures were determined through degradation and spectroscopic methods; a biosynthetic pathway was proposed. 6 Syntheses of constanolactone A and B 5f-h as well as constanolactone E 5i,j were reported, partly driven by the fact that despite the known biological activity of cyclopropyl lactones, physiological data are still scarce. Our own synthetic efforts first focussed on the synthesis of constanolactones A and B with an attempt to efficiently provide the key intermediates 1 and 2 ( Figure 1) that should readily give the natural products by a known chromium mediated addition.…”

mentioning

confidence: 99%

Total Synthesis of Marine OxylipinsConstanolactone A and B

Pietruszka¹,

Wilhelm²

2003

Synlett

View full text Add to dashboard Cite

show abstract

“…42). Useful background on the non-halogenated analogues in a range of marine biota has been given for both prostanoids [60] and the wider group of oxylipins [63].…”

Section: Prostanoidsmentioning

confidence: 99%

Biological Effects and Biosynthesis of Brominated Metabolites

Neilson

2003

The Handbook of Environmental Chemistry

View full text Add to dashboard Cite

Abstract. On the basis of halogenated metabolites assembled by Gribble, an attempt is made to provide a hypothesis for the biosynthesis of representative groups. Examples of brominated and iodinated metabolites are drawn from the major classes of terpenoids and acetogenins, and related to the biosynthesis of their putative precursors. Brominated and iodinated carbocyclic and heterocyclic aromatic compounds are discussed as weil as mechanisms for the oxidative coupling of phenolic substrates. A few chlorinated metabolites are introduced for additional illustration. Halogenation by cationoid (Hai+) reactions catalyzed by haloperoxidases is discussed, and attention drawn to the alternative role of anionoid (Hal-) halogenation. The presentation is extended to the biosynthesis of isonitriles and dichloroimines by anionoid reaction of precursors with cyanide. The range of biota that produce brominated substrates is briefly indicated, and comments made on the ecological significance of metabolites and associations among biota.

show abstract

Carbocyclic oxylipins of marine origin

Cited by 136 publications

References 61 publications

Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages

Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages

Total Synthesis of Marine OxylipinsConstanolactone A and B

Biological Effects and Biosynthesis of Brominated Metabolites

Contact Info

Product

Resources

About