4-Hydroxy hexenal derived from dietary n-3 polyunsaturated fatty acids induces anti-oxidative enzyme heme oxygenase-1 in multiple organs

Nakagawa, Fumiyuki; Morino, Katsutaro; Ugi, Satoshi; Ishikado, Atsushi; Kondo, Keiko; Sato, Daisuke; Konno, Shiho; Nemoto, Koji; Kusunoki, Chisato; Sato, Osamu; Sunagawa, Akihiro; Kawamura, Masanori; Inoue, Noriko; Nishio, Yoshihiko; Maegawa, Hiroshi

doi:10.1016/j.bbrc.2013.12.085

Cited by 35 publications

(33 citation statements)

References 35 publications

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“…By contrast, obesity is often accompanied with decreased levels of ω-3 PUFAs (Bermudez-Cardona and Velasquez-Rodriguez 2016), and ω-3 PUFAs are believed to be beneficial in the protection of normal cells from external stimuli (Ishikado et al 2013;Nakagawa et al 2014). Moreover, supplementation of ω-3 PUFAs improved the semen quality in subjects with idiopathic oligoasthenoteratospermia (Safarinejad 2011), which suggested that ω-3 PUFAs could protect male fertility.…”

Section: Discussionmentioning

confidence: 99%

“…For example, in the L02 cell line, PA treatment led to over-accumulation of ROS that impaired the oxidative capacity of the mitochondria (Bayram et al 2016). By contrast, ω-3 PUFAs exerted a protective role in normal cells due to their antioxidant activity (Nakagawa et al 2014). In human umbilical vein endothelial cells, DHA and 4-hydroxy hexenal (4-HHE), an end-product of ω-3 PUFA peroxidation, increased the antioxidant activity of the cells (Redza-Dutordoir and Averill-Bates 2016).…”

Section: Discussionmentioning

confidence: 99%

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Effects of saturated palmitic acid and omega-3 polyunsaturated fatty acids on Sertoli cell apoptosis

Liang

et al. 2018

Systems Biology in Reproductive Medicine

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FFA: free fatty acid; HFD: high-fat diet; SD: standard diet; PA: palmitic acid; PUFA: polyunsaturated fatty acid; AI: apoptotic index; MTT: 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide; ROS: reactive oxygen species; HE: Hematoxylin and eosin; WT1: Wilm Tumor 1; NAFLD: non- alcoholic fatty liver disease; DCFH-DA: 2', 7' dichloroﬂuorescin diacetate; 36B4: acidic ribosomal phosphoprotein P0; SD: standard deviation; EPA: eicosapentaenoic acid; PI: propidium iodide; DHA: docosahexenoic acid.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Effects of saturated palmitic acid and omega-3 polyunsaturated fatty acids on Sertoli cell apoptosis

Liang

et al. 2018

Systems Biology in Reproductive Medicine

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“…It should also be noted that some oxidation products from EPA and DHA may actually be beneficial to health. Nakagawa et al observed that 4‐HHE increases after fish oil consumption and protects vascular function .…”

Section: Health Effects Of Oxidized Epa and Dha Oilsmentioning

confidence: 99%

Oxidation in EPA‐ and DHA‐rich oils: an overview

Ismail¹,

Bannenberg²,

Rice³

et al. 2016

Lipid Technology

104

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Oxidation of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) rich omega-3 oils (hereafter referred to as either EPA and DHA or omega-3) is a complicated topic, but an important one to understand. A significant number of consumers cite fishy burp and/or taste, thought to be the result of oxidation, as one of the main reasons they do not consume EPA and DHA rich oils. In addition, consumers note that some articles have raised concerns about the potential for adverse effects associated with consumption of oxidized oils. Measuring oxidation in omega-3 oils is complicated due to the differences in chemical and physical characteristics of many commercially available products, which means not all methods to determine quality are appropriate for all types of oils. A number of consumer advocacy groups, product quality seal programs and academic groups have published data on levels of oxidation in omega-3 oils. Overall, this data shows that commercially available omega-3 supplements are low in oxidation. If consumers have a poor sensory experience with their omega-3 product, they should try another product as an alternative.

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“…In conclusion, the concentration of 4-HHE was closely related to the fatty acid composition of docosahexaenoic acid (DHA) in all tissues and thus DHA content was positively correlated with 4HHE concentration. Therefore, the relationship of DHA content to 4HHE concentration and HO-1 mRNA expression in these tissues suggest that 4HHE derived from DHA may induce HO-1 mRNA expression through activation of Nrf2 (Nakagawa et al, 2014). Another report also shows that 4HHE induces activation of the NFκB pathway in YPEN-1 cells, resulting in elevated expression of inducible nitric oxide synthases (iNOs) and nitric oxide production (Lee et al, 2004; Yang et al, 2008).…”

Section: -Hydroxyhexenal (4hhe)mentioning

confidence: 99%

Antioxidant role of glutathione S-transferases: 4-Hydroxynonenal, a key molecule in stress-mediated signaling

Singhal

Singh

Singhal

et al. 2015

Toxicology and Applied Pharmacology

187

110

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4-Hydroxy-2-trans-nonenal (4HNE), one of the major end products of lipid peroxidation (LPO), has been shown to induce apoptosis in a variety of cell lines. It appears to modulate signaling processes in more than one way because it has been suggested to have a role in signaling for differentiation and proliferation. It has been known that glutathione S-transferases (GSTs) can reduce lipid hydroperoxides through their Se-independent glutathione-peroxidase activity and that these enzymes can also detoxify LPO end-products such as 4HNE. Available evidence from earlier studies together with results of recent studies in our laboratories strongly suggests that LPO products, particularly hydroperoxides and 4HNE, are involved in the mechanisms of stress-mediated signaling and that it can be modulated by the alpha-class GSTs through the regulation of the intracellular concentrations of 4HNE. We demonstrate 4HNE induced apoptosis in various cell lines is accompanied with c-Jun-N-terminal kinase (JNK) and caspase-3 activation. Cells exposed to mild, transient heat or oxidative stress acquire the capacity to exclude intracellular 4HNE at a faster rate by inducing GSTA4-4 which conjugate 4HNE to glutathione (GSH), and RLIP76 which mediates the ATP-dependent transport of the GSH-conjugate of 4HNE (GS-HNE). The balance between formation and exclusion promotes different cellular processes – higher concentrations of 4HNE promote apoptosis; whereas, lower concentrations promote proliferation. In this article, we provide a brief summary of the cellular effects of 4HNE, followed by a review of its GST-catalyzed detoxification, with an emphasis on the structural attributes that play an important role in the interactions with alpha-class GSTA4-4. Taken together, 4HNE is a key signaling molecule and that GSTs being determinants of its intracellular concentrations, can regulate stress-mediated signaling, are reviewed in this article.

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4-Hydroxy hexenal derived from dietary n-3 polyunsaturated fatty acids induces anti-oxidative enzyme heme oxygenase-1 in multiple organs

Cited by 35 publications

References 35 publications

Effects of saturated palmitic acid and omega-3 polyunsaturated fatty acids on Sertoli cell apoptosis

Effects of saturated palmitic acid and omega-3 polyunsaturated fatty acids on Sertoli cell apoptosis

Oxidation in EPA‐ and DHA‐rich oils: an overview

Antioxidant role of glutathione S-transferases: 4-Hydroxynonenal, a key molecule in stress-mediated signaling

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