Linotrins: Omega-3 oxylipins featuring an E,Z,E conjugated triene motif are present in the plant kingdom and alleviate inflammation in LPS-challenged microglial cells

Balas, Laurence; Dey, Sujit; Béraud-Dufour, Sophie; Riechers, Dean E.; Landau, Olivia Augusta; Bertrand‐Michel, Justine; Blondeau, Nicolas

doi:10.1016/j.ejmech.2022.114157

Cited by 7 publications

(5 citation statements)

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“…Alpha-linolenic acid (ALA), the precursor of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in microalgae, is an essential omega-3 PUFA that the human body is unable to produce. This omega-3 is a peroxidation target for 15-lipoxygenase and produces linotrins [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

“…Linotrins (enzymatically oxidized derivatives) were studied in microalgae for the first time, and larger concentrations were detected in Mi133. Linotrins are one of the target metabolites with biological activity that exhibits a reduction in microglia inflammation [ 23 ].…”

Section: Discussionmentioning

confidence: 99%

“…Some derivatives of LA and ARA have been shown to regulate endogenous inflammation levels [ 21 , 22 ]. The lipoxygenase-catalyzed derivatives of ALA, such as EPA (resolvins E) and DHA (resolvins D, protectins), have been reported to display anti-inflammatory properties [ 23 ] in nano and picomolar levels [ 24 , 25 ]. Among the other biological activities of DHA-derived molecules, these molecules can promote tissue regeneration [ 26 ] or alleviate post-operative pain [ 27 ].…”

Section: Introductionmentioning

confidence: 99%

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Bioactive Oxylipins Profile in Marine Microalgae

et al. 2023

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Microalgae are photosynthetic microscopic organisms that serve as the primary food source in aquatic environments. Microalgae can synthesize a wide variety of molecules, such as polyunsaturated fatty acids (PUFAs) of the omega-3 and omega-6 series. Oxidative degradation of PUFA due to radical and/or enzymatic conversion leads to the formation of oxylipins, which are compounds known for their bioactive properties. In the present study, we aim to profile oxylipins from five microalgae species grown in 10-L photo-bioreactors under optimal conditions. During their exponential phase, microalgae were harvested, extracted and analyzed by LC-MS/MS to determine the qualitative and quantitative profile of oxylipins for each species. The five different selected microalgae revealed a high diversity of metabolites, up to 33 non-enzymatic and 24 enzymatic oxylipins present in different concentrations. Taken together, these findings highlight an interesting role of marine microalgae as a source of bioactive lipids mediators, which we hypothesize have an important function in preventive health measures such as amelioration of inflammation. The rich mixture of oxylipins may display advantages to biological organisms, especially by providing for human health benefits including antioxidant, anti-inflammatory, neuroprotective or immunomodulator activities. Some oxylipins are also well known for their cardiovascular properties.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bioactive Oxylipins Profile in Marine Microalgae

et al. 2023

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“…Similarly, a recent study presenting total synthesis of the 9,16-DiHOTREs revealed that 30 µM 9(R),16(R,S)-DiHOTrEs reduces LPS-stimulated secretion of IL-6 and TNF-α in mouse BV2 microglial cells. These rather high concentrations are still 3-fold lower than the concentrations of ALA necessary to elicit similar effects [ 77 ].…”

Section: Effects and Mechanism Of Ala And Its Oxylipins On Inflammati...mentioning

confidence: 99%

The Role of α-Linolenic Acid and Its Oxylipins in Human Cardiovascular Diseases

Cambiaggi

Chakravarty

Noureddine

et al. 2023

IJMS

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α-linolenic acid (ALA) is an essential C-18 n-3 polyunsaturated fatty acid (PUFA), which can be elongated to longer n-3 PUFAs, such as eicosapentaenoic acid (EPA). These long-chain n-3 PUFAs have anti-inflammatory and pro-resolution effects either directly or through their oxylipin metabolites. However, there is evidence that the conversion of ALA to the long-chain PUFAs is limited. On the other hand, there is evidence in humans that supplementation of ALA in the diet is associated with an improved lipid profile, a reduction in the inflammatory biomarker C-reactive protein (CRP) and a reduction in cardiovascular diseases (CVDs) and all-cause mortality. Studies investigating the cellular mechanism for these beneficial effects showed that ALA is metabolized to oxylipins through the Lipoxygenase (LOX), the Cyclooxygenase (COX) and the Cytochrome P450 (CYP450) pathways, leading to hydroperoxy-, epoxy-, mono- and dihydroxylated oxylipins. In several mouse and cell models, it has been shown that ALA and some of its oxylipins, including 9- and 13-hydroxy-octadecatrienoic acids (9-HOTrE and 13-HOTrE), have immunomodulating effects. Taken together, the current literature suggests a beneficial role for diets rich in ALA in human CVDs, however, it is not always clear whether the described effects are attributable to ALA, its oxylipins or other substances present in the supplemented diets.

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“…A total of 26 discriminative pathways were characterized using LefSe analysis (Figure 2g, LDA > 2). After DON exposure, the abundance of metabolic pathways related to mitochondrial metabolism and apoptosis (ko00660, ko01040) [23,24] and the degradation and metabolism of DON (ko00253, ko01054, and ko00625) [25] increased, while the abundance of metabolic pathways related to anti-inflammatory and antioxidant effects (ko00510, ko00592, ko00950, ko00250, and ko00020) [26][27][28][29] decreased.…”

Section: Don Exposure Induced the Alterations In Microbiota Microbial...mentioning

confidence: 99%

Deoxynivalenol Exposure Induced Colon Damage in Mice Independent of the Gut Microbiota

Liao,

Peng,

et al. 2023

Molecular Nutrition Food Res

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ScopeTo investigate whether deoxynivalenol (DON) can induce intestinal damage through gut microbiota in mice.Methods and resultsMice are orally administered DON (1 mg kg−1 bw day−1) for 4 weeks, and then recipient mice receive fecal microbiota transplantation (FMT) from DON‐exposed mice after antibiotic treatment. Furthermore, the mice are orally treated with DON (1 mg kg−1 bw day−1) for 4 weeks after antibiotic treatment. Histological damage, disruption of tight junction protein expression, and increased oxidative stress and apoptosis in the colon as well as higher serum lipopolysaccharides are observed after DON exposure. Moreover, DON exposure changes the composition and diversity of the gut microbiota as well as the contents of fecal metabolites (mainly bile acids). Differential metabolic pathways may be related to mitochondrial metabolism, apoptosis, and inflammation following DON exposure. However, only a decrease in mRNA levels of occludin and claudin‐3 is observed in the colon of recipient mice after FMT. After depleting the gut microbiota in mice, DON exposure can also cause histological damage, disorders of tight junction protein expression, and increased oxidative stress and apoptosis in the colon.ConclusionsDON exposure can induce colon damage in mice independent of the gut microbiota.

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Linotrins: Omega-3 oxylipins featuring an E,Z,E conjugated triene motif are present in the plant kingdom and alleviate inflammation in LPS-challenged microglial cells

Cited by 7 publications

References 76 publications

Bioactive Oxylipins Profile in Marine Microalgae

Bioactive Oxylipins Profile in Marine Microalgae

The Role of α-Linolenic Acid and Its Oxylipins in Human Cardiovascular Diseases

Deoxynivalenol Exposure Induced Colon Damage in Mice Independent of the Gut Microbiota

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