Metabolism and biological production of resolvins derived from docosapentaenoic acid (DPAn-6)

Dangi, Bindi; Obeng, Marcus; Nauroth, Julie M.; Chung, Gloria H.; Bailey-Hall, Eileen; Hallenbeck, Todd; Arterburn, Linda M.

doi:10.1016/j.bcp.2009.08.001

Cited by 23 publications

(14 citation statements)

References 24 publications

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“…Both isoprostanes and neuroprostanes are produced non-enzymatically, and have no known biological function, but are sometimes used as surrogate measures of oxidative stress. Likewise, DPA may be enzymatically oxidized by lipoxygenases [40], and 12-LOX can convert DPA to anti-inflammatory oxylipins [41] and resolvins [42], although DPA levels in RBC membranes are also correlated with elevated inflammatory markers [43]. Elevated brain DPA concentrations in rats fed a 0.2% α-LNA diet are accompanied by increased DPA turnover in brain phospholipids, which may be related to the increased activity of Ca 2+ -dependent cytosolic phospholipase A 2 in the deprived rats [44].…”

Section: Discussionmentioning

confidence: 99%

“…At least one ω6-PUFA oxidation product is amyloidogenic while its corresponding ω3-PUFA oxidation product is not [27], suggesting that dietary ω3-PUFA deficiency may render brain tissue more vulnerable to amyloidogenic effects of oxidative stress by increasing the production of ω6-PUFA oxidation products [41,48]. Conversely, dietary DHA supplementation alleviates the histopathological signs of Alzheimer’s disease in mice, and in neuronal cell cultures [33,49–55].…”

Section: Discussionmentioning

confidence: 99%

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Increased ω6-Containing Phospholipids and Primary ω6 Oxidation Products in the Brain Tissue of Rats on an ω3-Deficient Diet

et al. 2016

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Polyunsaturated fatty acyl (PUFA) chains in both the ω3 and ω6 series are essential for normal animal brain development, and cannot be interconverted to compensate for a dietary deficiency of one or the other. Paradoxically, a dietary ω3-PUFA deficiency leads to the accumulation of docosapentaenoate (DPA, 22:5ω6), an ω6-PUFA chain that is normally scarce in the brain. We applied a high-precision LC/MS method to characterize the distribution of DPA chains across phospholipid headgroup classes, the fatty acyl chains with which they were paired, and the extent to which they were oxidatively damaged in the cortical brain of rats on an ω3-deficient diet. Results indicate that dietary ω3-PUFA deficiency markedly increased the concentrations of phospholipids with DPA chains across all headgroup subclasses, including plasmalogen species. The concentrations of phospholipids containing docosahexaenoate chains (22:6ω3) decreased 20–25%, while the concentrations of phospholipids containing arachidonate chains (20:4ω6) did not change significantly. Although DPA chains are more saturated than DHA chains, a larger fraction of DPA chains were monohydroxylated, particularly among diacyl-phosphatidylethanolamines and plasmalogen phosphatidylethanolamines, suggesting that they were disproportionately subjected to oxidative stress. Differences in the pathological significance of ω3 and ω6 oxidation products suggest that greater oxidative damage among the ω6 PUFAs that increase in response to dietary ω3 deficiency may have pathological significance in Alzheimer’s disease.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Increased ω6-Containing Phospholipids and Primary ω6 Oxidation Products in the Brain Tissue of Rats on an ω3-Deficient Diet

et al. 2016

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“…In addition, despite n-6 DPA does not completely replace DHA in n-3 PUFA deficient animals (Greiner et al, 2003), its increase could be involved in the lower proinflammatory cytokine production in the brain of n-3 PUFA deficient mice. Indeed, it was shown that n-6 DPA reduces inflammatory mediators in human peripheral mononuclear cells in vitro (Dangi et al, 2009;Nauroth et al, 2010). Moreover, n-6 DPA can be the precursor for resolvins, involved in dampening and resolution of inflammation in macrophages (Lim et al, 2005b;Chiu et al, 2012).…”

Section: )mentioning

confidence: 98%

Dietary n-3 PUFAs Deficiency Increases Vulnerability to Inflammation-Induced Spatial Memory Impairment

Delpech

Thomazeau

Madore

et al. 2015

Neuropsychopharmacol

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Dietary n-3 polyunsaturated fatty acids (PUFAs) are critical components of inflammatory response and memory impairment. However, the mechanisms underlying the sensitizing effects of low n-3 PUFAs in the brain for the development of memory impairment following inflammation are still poorly understood. In this study, we examined how a 2-month n-3 PUFAs deficiency from pre-puberty to adulthood could increase vulnerability to the effect of inflammatory event on spatial memory in mice. Mice were given diets balanced or deficient in n-3 PUFAs for a 2-month period starting at post-natal day 21, followed by a peripheral administration of lipopolysaccharide (LPS), a bacterial endotoxin, at adulthood. We first showed that spatial memory performance was altered after LPS challenge only in n-3 PUFA-deficient mice that displayed lower n-3/n-6 PUFA ratio in the hippocampus. Importantly, long-term depression (LTD), but not long-term potentiation (LTP) was impaired in the hippocampus of LPS-treated n-3 PUFA-deficient mice. Proinflammatory cytokine levels were increased in the plasma of both n-3 PUFA-deficient and n-3 PUFA-balanced mice. However, only n-3 PUFA-balanced mice showed an increase in cytokine expression in the hippocampus in response to LPS. In addition, n-3 PUFA-deficient mice displayed higher glucocorticoid levels in response to LPS as compared with n-3 PUFA-balanced mice. These results indicate a role for n-3 PUFA imbalance in the sensitization of the hippocampal synaptic plasticity to inflammatory stimuli, which is likely to contribute to spatial memory impairment.

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“…As described above, AA plays a central role in inflammation related to injury and many diseased states; linoleic acid is a polyunsaturated fatty acid used in the biosynthesis of AA. As to the other three fatty acids, stearic acid is the saturated derivative from hydrogenation of double bond of oleic acid (Dangi et al, 2010), and hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants (Beare-Rogers et al, 2001). These are not only the main energy source as nutrients, but also signaling molecules in various cellular processes.…”

Section: Figmentioning

confidence: 99%

A plasma metabonomic investigation into the intervention of volatile oil of Magnolia biondii Pamp on rat model of acute inflammation

et al. 2011

Journal of Ethnopharmacology

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Metabolism and biological production of resolvins derived from docosapentaenoic acid (DPAn-6)

Cited by 23 publications

References 24 publications

Increased ω6-Containing Phospholipids and Primary ω6 Oxidation Products in the Brain Tissue of Rats on an ω3-Deficient Diet

Increased ω6-Containing Phospholipids and Primary ω6 Oxidation Products in the Brain Tissue of Rats on an ω3-Deficient Diet

Dietary n-3 PUFAs Deficiency Increases Vulnerability to Inflammation-Induced Spatial Memory Impairment

A plasma metabonomic investigation into the intervention of volatile oil of Magnolia biondii Pamp on rat model of acute inflammation

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