Plumbagin: a natural product for smart materials?

Newton, Laura A. A.; Cowham, Emma; Sharp, Duncan; Leslie, R. Vincent; Davis, James A.

doi:10.1039/b9nj00534j

Cited by 10 publications

(11 citation statements)

References 12 publications

(17 reference statements)

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“…In order to establish the possible involvement of oxygen in the formation of the described coatings, a series of parallel experiments in deaerated electrolytes under argon were carried out. These experiments were necessary since it is well known that reduced quinone species and polymers can reduce oxygen 30 . Figure 4 shows the CV of a solution of MBQ in deaerated acetonitrile and under Ar flow (5a) and in air, as above (5b).…”

Section: Resultsmentioning

confidence: 99%

Hurdles to organic quinone flow cells. Electrode passivation by quinone reduction in acetonitrile Li electrolytes

Rueda-García

Dubal

Huguenin

et al. 2017

Journal of Power Sources

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Section: Resultsmentioning

confidence: 99%

Hurdles to organic quinone flow cells. Electrode passivation by quinone reduction in acetonitrile Li electrolytes

Rueda-García

Dubal

Huguenin

et al. 2017

Journal of Power Sources

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“…Nrf2 activity is induced in response to oxidative stress and plumbagin has reported ROS generating activity [42]. We therefore examined whether plumbagin activation of ARE-containing targets could be altered by treatment with glutathione, an antioxidant capable of scavenging plumbagin-generated ROS.…”

Section: Resultsmentioning

confidence: 99%

Extension of Lifespan in C. elegans by Naphthoquinones That Act through Stress Hormesis Mechanisms

et al. 2011

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Hormesis occurs when a low level stress elicits adaptive beneficial responses that protect against subsequent exposure to severe stress. Recent findings suggest that mild oxidative and thermal stress can extend lifespan by hormetic mechanisms. Here we show that the botanical pesticide plumbagin, while toxic to C. elegans nematodes at high doses, extends lifespan at low doses. Because plumbagin is a naphthoquinone that can generate free radicals in vivo, we investigated whether it extends lifespan by activating an adaptive cellular stress response pathway. The C. elegans cap‘n’collar (CNC) transcription factor, SKN-1, mediates protective responses to oxidative stress. Genetic analysis showed that skn-1 activity is required for lifespan extension by low-dose plumbagin in C. elegans. Further screening of a series of plumbagin analogs identified three additional naphthoquinones that could induce SKN-1 targets in C. elegans. Naphthazarin showed skn-1dependent lifespan extension, over an extended dose range compared to plumbagin, while the other naphthoquinones, oxoline and menadione, had differing effects on C. elegans survival and failed to activate ARE reporter expression in cultured mammalian cells. Our findings reveal the potential for low doses of naturally occurring naphthoquinones to extend lifespan by engaging a specific adaptive cellular stress response pathway.

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“…produced undergo disproportionation and reaction with itself producing transients having absorption in the same wavelength region. Redox reactions of THQ seem to undergo disproportionation and cross‐reactions as suggested earlier for other hydroquinones also . A probable mechanism for reaction of THQ transients can be given based on redox studies on quinones reported earlier (Equations 1,2,9,10) …”

Section: Resultsmentioning

confidence: 69%

“…This is possible due to chain reactions for quinonic and phenolic molecules through disproportionation, cross-reactions and radical-molecule reactions. [21][22][23][24] Further, similar reactions were suggested also in the electrochemical polymerization of plumbagin [28] and oxidative polymerization of phenols [29] . It is to be noted that absorption spectra of the transients obtained in the reaction of THQ with reducing (eaq ) and oxidizing (COH, N 3 C and CCl 3 O 2 C) radicals are in the UV-visible absorption region of THQ ( Figure S6).…”

Section: Resultsmentioning

confidence: 83%

Free Radical Scavenging Reactions of Tetrahydroxyquinone: A Pulse Radiolysis Study

Joshi

2016

ChemistrySelect

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Free radical induced redox reaction kinetics and mechanism of tetrahydroxy‐1,4‐benzoquinone (THQ) has been studied using pulse radiolysis technique. THQ efficiently scavenged hydrated electron, superoxide radical anion, ethanol radical, hydroxyl radical, azidyl radical, thiocyanate radical anion, sulfate radical anion, haloperoxyl radical, lipid peroxyl radical, tryptophanyl radical and tyrosyl radical. Transient absorption spectra of THQ semiquinone radical anion, THQ radical cation and THQ radical produced with these free radicals and rate constants for these reactions have been studied. A probable mechanism of free radical induced redox reactions of THQ has been proposed. Reaction of THQ with free radicals and cyclic voltammetry measurements suggest its oxidation potentials at 0.81 V and 0.94 V vs NHE. To the best of our knowledge, free radical reactions of THQ have been reported for the first time.

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Plumbagin: a natural product for smart materials?

Cited by 10 publications

References 12 publications

Hurdles to organic quinone flow cells. Electrode passivation by quinone reduction in acetonitrile Li electrolytes

Hurdles to organic quinone flow cells. Electrode passivation by quinone reduction in acetonitrile Li electrolytes

Extension of Lifespan in C. elegans by Naphthoquinones That Act through Stress Hormesis Mechanisms

Free Radical Scavenging Reactions of Tetrahydroxyquinone: A Pulse Radiolysis Study

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