Ergothioneine stands out from hercynine in the reaction with singlet oxygen: Resistance to glutathione and TRIS in the generation of specific products indicates high reactivity

Free Radical Biology & Medicine
Christopher StoffelsD Gründemann

Abstract

The candidate vitamin ergothioneine (ET), an imidazole-2-thione derivative of histidine betaine, is generally considered an antioxidant. However, the precise physiological role of ET is still unresolved. Here, we investigated in vitro the hypothesis that ET serves specifically to eradicate noxious singlet oxygen (1O2). Pure 1O2 was generated by thermolysis at 37°C of N,N'-di(2,3-dihydroxypropyl)-1,4-naphthalenedipropanamide 1,4-endoperoxide (DHPNO2). Assays of DHPNO2 with ET or hercynine (= ET minus sulfur) at pH 7.4 were analyzed by LC-MS in full scan mode to detect products. Based on accurate mass and product ion scan data, several products were identified and then quantitated as a function of time by selected reaction monitoring. All products of hercynine contained, after a [4+2] cycloaddition of 1O2, a carbonyl at position 2 of the imidazole ring. By contrast, because of the doubly bonded sulfur, we infer from the products of ET as the initial intermediates a 4,5-dioxetane (after [2+2] cycloaddition) and hydroperoxides at position 4 and 5 (after Schenck ene reactions). The generation of single products from ET, but not from hercynine, was fully resistant to a large excess of tris(hydroxymethyl)aminomethane (TRIS) or glutath...Continue Reading

Citations

Jun 1, 2018·FEBS Letters·Barry HalliwellRichard M Y Tang
Mar 14, 2018·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Julia TschirkaDirk Gründemann
Sep 24, 2019·Chemistry : a European Journal·Kristina V GoncharenkoFlorian P Seebeck
Feb 14, 2020·Nutrition Research Reviews·Irina BorodinaDouglas B Kell
Jul 11, 2020·Antioxidants·Irwin K Cheah, Barry Halliwell
Feb 10, 2021·Redox Biology·Irwin K Cheah, Barry Halliwell
Apr 17, 2018·ACS Chemical Biology·Laëtitia MissonFlorian P Seebeck
Oct 9, 2021·Antioxidants & Redox Signaling·Bindu D Paul
Dec 28, 2021·FEBS Letters·Dirk GründemannSvenja Flögel

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