Covalent adduction of endogenous and food-derived quinones to a protein: its biological significance

Kato, Yoji; Suga, Naoko

doi:10.3164/jcbn.18-26

Cited by 17 publications

(12 citation statements)

References 74 publications

(91 reference statements)

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“…( 18 , 31 ) In general, a quinone compound covalently forms adducts with thiol moieties; these reactions may be involved in the development of diseases or adaptation to stress. ( 32 ) We have reported that the pretreatment of SH-SY5Y cells with TD prevented cell death and suppressed intracellular ROS generation evoked by H 2 O 2 exposure. ( 33 ) This may occur because cells primed with TD upregulate the expression of the phase-II antioxidant enzymes NAD(P)H: quinone oxidoreductase 1 and heme oxygenase-1.…”

Section: Discussionmentioning

confidence: 99%

Elevation of the serotonin-derived quinone, tryptamine-4,5-dione, in the intestine of ICR mice with dextran sulfate-induced colitis

Suga

Murakami

Arimitsu

et al. 2021

J. Clin. Biochem. Nutr.

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Inflammatory bowel diseases, including Crohn’s disease and ulcerative colitis, are chronic inflammatory disorders associated with oxidative stress. The intestines produce 5-hydroxytryptamine that may negatively affect disease state under inflammatory conditions when overproduced. 5-Hydroxytryptamine is a substrate for myeloperoxidase and is converted into reactive tryptamine-4,5-dione. Here, an experimental colitis model was established through oral administration of 5% dextran sulfate sodium to ICR mice for 7 days. Furthermore, the formation of tryptamine-4,5-dione in the colorectal mucosa/submucosa and colorectal tissue was analyzed by chemical and immunochemical methodologies. First, free tryptamine-4,5-dione in the homogenate was chemically trapped by o -phenylenediamine and analyzed as the stable phenazine derivative. Tryptamine-4,5-dione localization as adducted proteins in the colorectal tissue was immunohistochemically confirmed, and as demonstrated by both methods, this resulted in the significant increase of tryptamine-4,5-dione in dextran sulfate sodium-challenged mice compared with control mice. Immunohistochemical staining confirmed tryptamine-4,5-dione-positive staining at the myeloperoxidase accumulation site in dextran sulfate sodium-challenged mice colorectal tissue. The tryptamine-4,5-dione locus in the mice was partly matched with that of a specific marker for myeloperoxidase, halogenated tyrosine. Overall, the results possibly indicate that tryptamine-4,5-dione is generated by neutrophil myeloperoxidase in inflammatory tissue and may contribute to the development of inflammatory bowel disease.

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Section: Discussionmentioning

confidence: 99%

Elevation of the serotonin-derived quinone, tryptamine-4,5-dione, in the intestine of ICR mice with dextran sulfate-induced colitis

Suga

Murakami

Arimitsu

et al. 2021

J. Clin. Biochem. Nutr.

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“…The formed quinone could react with a thiol of the enzyme, resulting in the enzyme conjugation with the phytochemical (Fig. 4) [31]. Piceatannol is abundantly present in the fruit of Passiflora edulis [32] and is a metabolite of resveratrol.…”

Section: Discussionmentioning

confidence: 99%

Food phytochemicals, epigallocatechin gallate and myricetin, covalently bind to the active site of the coronavirus main protease in vitro

Kato

Higashiyama

Takaoka

et al. 2021

Preprint

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SARS-CoV-2 main protease is a possible target for protection against viral infection. This study examined the inhibitory effect of food phytochemicals on the main protease of SARS-CoV-2 by determining a cleaved product after chromatographic separation. First, 37 phytochemicals, including glycosides and metabolites, were screened at 20 µM; epigallocatechin gallate, myricetin, theaflavin, herbacetin, piceatannol, myricitrin, and isothiocyanates inhibited the enzyme in varying degrees. The IC50 values were estimated from 0.4 to 33.3 µM against the 0.5-µM enzyme. The dose-dependent adduction of epigallocatechin gallate and myricetin was confirmed by quinone staining of protein blotted onto a membrane. The enzyme activity was decreased by increasing the concentration of the two phytochemicals, accompanied by increasing the respective adducted molecule estimated by intact mass spectrometry. Reduced glutathione canceled the formation of conjugate and the inhibitory effect of epigallocatechin gallate or myricetin on the enzyme, suggesting that the formation of the quinone moiety in the phytochemicals is critical for the inhibition. The covalent binding of epigallocatechin gallate or myricetin to the cysteine residue at the active site was confirmed by analyzing peptides from the chymotrypsin-digested main protease.

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“…The higher level of TPC in methanol extract than water extract, despite higher polarity of water, can also be related to the inhibitory action of methanol on the enzyme polyphenol oxidase [49] , which catalyzes two types of oxidative reactions: hydroxylation of monophenols to o-diphenols and oxidation of catechols to o-quinones, which are highly reactive compounds [50] . More importantly, o-quinones can easily combine with proteins to form insoluble complexes [51] .…”

Section: Phytochemical Analysismentioning

confidence: 99%

Phytochemicals and Antioxidant Properties of Solvent Extracts from Purslane (Portulaca oleracea L.): A Preliminary Study

Habibian¹,

Sadeghi

Karimi

2020

FSE

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A systematic study was conducted about the solvent effect on the purslane total phenolic, flavonoid, alkaloid, carotenoid, saponin, vitamin E, and vitamin C contents as well as to evaluate their contribution to overall antioxidant activity. Among three solvents investigated, water could extract the highest levels of solid and saponin contents, whereas methanol was more effective for obtaining phenolic, flavonoid, and alkaloid compounds than other solvents. Meanwhile, ethanol was the best choice for extracting carotenoids and vitamin E. In various experimental models including DPPH radical scavenging activity, ABTS+ radical scavenging activity, and ferric reducing antioxidant power, methanol extract consistently showed significantly greater antioxidant activity than other extracts, while ethanol extract provided the most efficient inhibiting activity against ferrous chloride-induced oxidation of linoleic acid. In addition, the scavenging efficiency of ethanol extract toward DPPH and ABTS+ radicals was significantly higher than the water extract, and vice versa was the case for ferric reducing antioxidant power. Overall, methanol was found to be the most favorable solvent for the extraction of phenolic, flavonoid, and alkaloid compounds that are promising as natural antioxidants. However, different solvents may be used to extract specific antioxidant compounds with distinctive antioxidant activity.

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Covalent adduction of endogenous and food-derived quinones to a protein: its biological significance

Cited by 17 publications

References 74 publications

Elevation of the serotonin-derived quinone, tryptamine-4,5-dione, in the intestine of ICR mice with dextran sulfate-induced colitis

Elevation of the serotonin-derived quinone, tryptamine-4,5-dione, in the intestine of ICR mice with dextran sulfate-induced colitis

Food phytochemicals, epigallocatechin gallate and myricetin, covalently bind to the active site of the coronavirus main protease in vitro

Phytochemicals and Antioxidant Properties of Solvent Extracts from Purslane (Portulaca oleracea L.): A Preliminary Study

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