Redox ticklers and beyond: Naphthoquinone repository in the spotlight against inflammation and associated maladies

Kapoor, Neha; Kandwal, Pankaj; Sharma, Gaurav; Gambhir, Lokesh

doi:10.1016/j.phrs.2021.105968

Cited by 23 publications

(19 citation statements)

References 110 publications

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“…Compounds 1, 4, and 5 also exhibited similar ferric ion-reducing ability to that of vitamin E. However, compound 3 showed the weakest FRAP ability, which corresponds to its relatively weak DPPH and ABTS free radical scavenging capacity. This finding is consistent with the conclusions reported in the previous literature (Kapoor, Kandwal, Sharma, & Gambhir, 2021).…”

Section: Frap Capacitysupporting

confidence: 94%

Hypoglycemic and antioxidative activity evaluation of phenolic compounds derived from walnut diaphragm produced in Xinjiang

Liu

Pei

2022

Journal of Food Biochemistry

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Walnut diaphragm is defined as a dry wood septum located between the walnut shell and kernel. In this work, seven phenolic compounds from walnut diaphragm were purified and characterized, and their antioxidant activities and mechanisms of hypoglycemia were investigated. Compounds 1–7 were tested for DPPH, ABTS scavenging ability, and FRAP assay to evaluate the antioxidant activity. α‐Amylase inhibition assay was introduced to assess the hypoglycemic activity, and the mechanism was investigated by kinetic analysis, CD spectrum, and molecular docking. Compound 6 showed the strongest antioxidant ability, while compound 1 exhibited the strongest inhibition of α‐amylase by changing the secondary structure of α‐amylase in a mixed competitive inhibition mode. Molecular docking test predicted that the tetrahydropyran part in compound 1 may contribute to its hypoglycemic effect. This study furnishes a new theoretical reference for the utilization and development of walnut diaphragm into a health food with antioxidant and hypoglycemic properties. Practical applications The finding of this research may serve as a basis for the subsequent development of walnut diaphragm into instant tea‐based health food or added to other food carriers to achieve auxiliary antioxidant and hypoglycemic effects. This study revealed that polyphenolic components were the material basis for the antioxidant and hypoglycemic effects of walnut diaphragm, which could be identified as landmark chemical components for controlling quality standards in the development of walnut diaphragm, thus accelerating the research process of quality standards for walnut diaphragm‐related products. Furthermore, the studies on the mechanism of hypoglycemic activity supply more credible data to support the development of walnut diaphragm into a safe and consumer‐friendly health food. With abundant resources and clear efficacy, walnut diaphragm has great development prospect and application value.

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Section: Frap Capacitysupporting

confidence: 94%

Hypoglycemic and antioxidative activity evaluation of phenolic compounds derived from walnut diaphragm produced in Xinjiang

Liu

Pei

2022

Journal of Food Biochemistry

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“…Polysulfides (S > 2) can also be produced by multiple reactions between sulfane and a persulfide (Equation ( 10)), nS 0 + H 2 S 2 → H 2 S (n+2) (10) or dimerization of persulfide radicals (Equation ( 11)),…”

Section: Possible Mechanisms Of Per-and Polysulfide Sulfite and Thios...mentioning

confidence: 99%

“…•− ) and hydrogen peroxide (H 2 O 2 ) [10,11]. These ROS may elicit cytoprotective effects in healthy cells by activating endogenous antioxidant responses or may kill ROS-sensitive tumor cells [10].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Collectively, NQs are well known as redox-cycling and alkylating agents, although much of their biological efficacy has been attributed to redox processes through the generation of reactive oxygen species (ROS), namely superoxide (O 2 ∙− ) and hydrogen peroxide (H 2 O 2 ) [ 10 , 11 ]. These ROS may elicit cytoprotective effects in healthy cells by activating endogenous antioxidant responses or may kill ROS-sensitive tumor cells [ 10 ]. A number of studies have shown that NQs may be reduced by NADH or NADPH in reactions catalyzed by cytochrome P450 reductase or NAD(P)H:quinone oxidoreductase-1 (NQO-1), the former being an one-electron reduction to the semiquinone and the latter a two-electron reduction to the hydroquinone (reviewed in [ 11 ]).…”

Section: Introductionmentioning

confidence: 99%

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Naphthoquinones Oxidize H2S to Polysulfides and Thiosulfate, Implications for Therapeutic Applications

Olson

Clear

Derry

et al. 2022

IJMS

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1,4-Napththoquinones (NQs) are clinically relevant therapeutics that affect cell function through production of reactive oxygen species (ROS) and formation of adducts with regulatory protein thiols. Reactive sulfur species (RSS) are chemically and biologically similar to ROS and here we examine RSS production by NQ oxidation of hydrogen sulfide (H2S) using RSS-specific fluorophores, liquid chromatography-mass spectrometry, UV-Vis absorption spectrometry, oxygen-sensitive optodes, thiosulfate-specific nanoparticles, HPLC-monobromobimane derivatization, and ion chromatographic assays. We show that NQs, catalytically oxidize H2S to per- and polysulfides (H2Sn, n = 2–6), thiosulfate, sulfite and sulfate in reactions that consume oxygen and are accelerated by superoxide dismutase (SOD) and inhibited by catalase. The approximate efficacy of NQs (in decreasing order) is, 1,4-NQ ≈ juglone ≈ plumbagin > 2-methoxy-1,4-NQ ≈ menadione >> phylloquinone ≈ anthraquinone ≈ menaquinone ≈ lawsone. We propose that the most probable reactions are an initial two-electron oxidation of H2S to S0 and reduction of NQ to NQH2. S0 may react with H2S or elongate H2Sn in variety of reactions. Reoxidation of NQH2 likely involves a semiquinone radical (NQ·−) intermediate via several mechanisms involving oxygen and comproportionation to produce NQ and superoxide. Dismutation of the latter forms hydrogen peroxide which then further oxidizes RSS to sulfoxides. These findings provide the chemical background for novel sulfur-based approaches to naphthoquinone-directed therapies.

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Synthetic Naphthoquinone Derivatives as Anticancer Agents in Ovarian Cancer: Cytotoxicity Assay and Investigation of Possible Biological Mechanisms Action

Daltoé

Rangel

Delarmelina

et al. 2023

Chemistry & Biodiversity

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In this study, eight naphthoquinone derivatives were synthesized in yields ranging from 52 to 96% using easy, fast, and low‐cost methodologies. All naphthoquinone derivatives were screened for their in vitro anti‐proliferative activities against OVCA A2780 cancer cell lines. Amongst all analysed compounds, derivatives 3–5 presented the most prominent cytotoxic potential. Naphthoquinones 3 and 4, bearing sulfur‐containing groups, were identified as having high potential for ROS production, in particular the superoxide anion. Furthermore, 3 and 4 compounds caused a decrease in the cell population in G0/G1 and induced more than 90% of the cell population to apoptosis. Compound 5 did not act in any of these processes. Finally, compounds 3–5 were tested for their inhibitory ability against PI3K and MAPK. Compounds 3 and 4 do not inhibit the PI3K enzyme. On the other hand, the naphthoquinone‐polyphenol 5 was only able to inhibit the percentage of cells expressing pERK.

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Redox ticklers and beyond: Naphthoquinone repository in the spotlight against inflammation and associated maladies

Cited by 23 publications

References 110 publications

Hypoglycemic and antioxidative activity evaluation of phenolic compounds derived from walnut diaphragm produced in Xinjiang

Hypoglycemic and antioxidative activity evaluation of phenolic compounds derived from walnut diaphragm produced in Xinjiang

Naphthoquinones Oxidize H2S to Polysulfides and Thiosulfate, Implications for Therapeutic Applications

Synthetic Naphthoquinone Derivatives as Anticancer Agents in Ovarian Cancer: Cytotoxicity Assay and Investigation of Possible Biological Mechanisms Action

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