Oxidative cleavage of polyunsaturated fatty acid chains via dioxygenation/pseudoperoxidation by 15-lipoxygenase

Koshiishi, Ichiro; Takigawa, Yuta

doi:10.1016/j.arres.2021.100023

Cited by 3 publications

(2 citation statements)

References 21 publications

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“…[19][20][21] Ferroptotic cell death occurring under low oxygen conditions, such as ischemia/reperfusion injury, is suggested to be induced by the interactions between polyunsaturated fatty acids and 15-lipoxygenase under hypoxic conditions. 22) In this reaction, ferrous 15-lipoxygenase donates one electron to lipid hydroperoxide instead of the labile ferrous ions. This mechanism suggests that the induction of ferroptosis in cancer cells follows a similar pathway under extreme hypoxia.…”

Section: Discussionmentioning

confidence: 99%

Quantitative Assessment of the Post-translational Modifications of Human Serum Albumin by Dimethyl Trisulfide

Koshiishi,

Nagai,

Yuzawa

et al. 2024

Biological & Pharmaceutical Bulletin

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Some bacteria, such as Fusobacterium nucleatum, act as dimethyl trisulfide (DMTS) producers in the host in vivo. DMTS acts as a sulfane sulfur donor and chemically modifies the sulfhydryl groups. This study explored the post-translational modifications of human serum albumin using DMTS. Quantitative assessments were conducted on mixed disulfides of mercaptoalbumin with mercaptomethane (Alb-SS-CH3) and albumin hydropersulfide (Alb-SSH) as post-translationally modified species. The hydropersulfide group was alkylated with iodoacetamide, resulting in the formation of an albumin-mercaptoacetamide mixed disulfide. The mixed disulfides were subsequently reduced with tris(2-carboxyethyl)phosphine, and the liberated mercaptomethane and mercaptoacetamide were fluorescently labeled with 4-fluoro-7-sulfamoylbenzofurazan (ABD-F). Quantification was performed using high-performance liquid chromatography (HPLC) with fluorescence detection. Using this methodology, we examined the formation of Alb-SS-CH3 and Alb-SSH via the reaction between 4% human serum albumin and DMTS at 10−100 µM concentrations. Approximately two molecules of Alb-SS-CH3 and one molecule of Alb-SSH were generated from one DMTS molecule. Moreover, hydrogen sulfide was identified as an intermediate, suggesting its generation and subsequent reaction with intraprotein disulfide bonds, leading to the production of Alb-SSH. These results suggest the production of DMTS in humans in vivo should be involved in the elevation of Alb-SS-CH3 and Alb-SSH contents in plasma samples.

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Section: Discussionmentioning

confidence: 99%

Quantitative Assessment of the Post-translational Modifications of Human Serum Albumin by Dimethyl Trisulfide

Koshiishi,

Nagai,

Yuzawa

et al. 2024

Biological & Pharmaceutical Bulletin

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“…However, it is unlikely that the substrate specificity of ferrous lipoxygenase for 13-(E/E)-HpODEs is superior to that for 13-(E/Z)-HpODEs. 24) Furthermore, in order to clarify the conjugated diene structure of the linoleate allyl radical complexed with ferrous lipoxygenase, we performed trapping experiments using the nitroxyl radical (CmΔP), which can trap carbon-centered radicals. On the assumption that the linoleate allyl radical with trans/trans-conjugated diene loosely binds to ferrous lipoxygenase, the trapping adducts must be chemically stable CmΔP-(E/E)-ODEs.…”

Section: Discussionmentioning

confidence: 99%

Isomerization of Oxidized Linoleate Metabolites with trans/cis Conjugated Diene Moiety to Those with trans/trans One in the Lipoxygenase/Linoleate/Hydrogen Polysulfide System

Takigawa

Nagai

Koshiishi

2023

Biological & Pharmaceutical Bulletin

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Endogenous hydrogen polysulfides are radical scavengers, and the resulting thiyl radical may catalyze isomerization of the cis-double bond to a trans-double bond. This study examined whether oxidized linoleate species with trans/trans-conjugated diene moieties were generated in the 15-lipoxygenase/linoleate/hydrogen polysulfide system at a lower oxygen content. When 40 µL of 0.1 M phosphate buffer (pH 7.4) containing 1.0 mM linoleate, 1.0 µM soybean 15-lipoxygenase, and 100 µM sodium trisulfide was placed in a 0.6 mL polypropylene microtube for 1 h at 25 °C, the proportion of (E/E)-oxo-octadecadienoic acids (OxoODEs) content to the total OxoODEs content was estimated to be more than 80% (mol/mol). OxoODEs are generated through the pseudoperoxidase reaction of ferrous 15-lipoxygenase with hydroperoxy octadecadienoic acids (HpODEs), which are produced by the lipoxygenase reaction of ferric 15-lipoxygenase. The content of OxoODEs was positively correlated with the content of 9-HpODEs, indicating that 9-HpODEs production is involved in converting ferric 15-lipoxygenase to ferrous 15-lipoxygenase. Furthermore, when 40 µL of 0.1 M phosphate buffer (pH 7.4) containing 1.0 mM linoleate, 1.0 µM soybean 15-lipoxygenase, 100 µM sodium trisulfide, and nitroxyl radical (carbon-centered radical-trapping agent, 3-carbamoyl-2,2,5,5-tetramethyl-3-pyrrolin-N-oxyl (CmΔP)) was incubated in a 0.6 mL polypropylene microtube at room temperature, CmΔP-(E/Z)-ODEs were isomerized to CmΔP-(E/E)-ODEs in a time-dependent manner and this isomerization was inhibited by a radical scavenger, Trolox. The results indicate that thiyl radicals derived from hydrogen polysulfides isomerize trans/cis conjugated diene moiety to the trans/trans moiety.

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低酸素下でフェロトーシス細胞死を誘導する脂質ラジカル種産生機構におけるリポキシゲナーゼの役割

Koshiishi

2024

YAKUGAKU ZASSHI

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Oxidative cleavage of polyunsaturated fatty acid chains via dioxygenation/pseudoperoxidation by 15-lipoxygenase

Cited by 3 publications

References 21 publications

Quantitative Assessment of the Post-translational Modifications of Human Serum Albumin by Dimethyl Trisulfide

Quantitative Assessment of the Post-translational Modifications of Human Serum Albumin by Dimethyl Trisulfide

Isomerization of Oxidized Linoleate Metabolites with <i>trans</i>/<i>cis</i> Conjugated Diene Moiety to Those with <i>trans</i>/<i>trans</i> One in the Lipoxygenase/Linoleate/Hydrogen Polysulfide System

低酸素下でフェロトーシス細胞死を誘導する脂質ラジカル種産生機構におけるリポキシゲナーゼの役割

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