Prooxidant action of gallic acid compounds: copper-dependent strand breaks and the formation of 8-hydroxy-2′-deoxyguanosine in DNA

Yoshino, Masataka; Haneda, Miyako; Naruse, Makoto; Htay, Hla; Iwata, S.; Tsubouchi, Ryoko; Murakami, Keiko

doi:10.1016/s0887-2333(02)00061-9

Cited by 52 publications

(23 citation statements)

References 16 publications

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“…The results arise from different techniques showed that PG binds to CT-DNA with a lower affinity through outside binding, maybe due to be considered in some cases as a natural and non-synthetic food additive. In the case of PG other researchers have indicated the antioxidative and cytoprotective properties of this food additive change to prooxidative, cytotoxic and genotoxic properties in the presence of Cu(II) and metal-mediated DNA damage caused by gallic acid hydrolysis product of PG plays an important role in the carcinogenicity of PG (Jacobi et al, 1997;Kobayashi et al, 2003;Wong & McLean, 1999;Yoshinoa et al, 2002). In fact PG has induced no or little DNA damage in the absence of metal ions, which corroborates our data.…”

Section: Discussionsupporting

confidence: 91%

A review on DNA interaction with synthetic phenolic food additives

Dolatabadi

Kashanian

2010

Food Research International

127

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Section: Discussionsupporting

confidence: 91%

A review on DNA interaction with synthetic phenolic food additives

Dolatabadi

Kashanian

2010

Food Research International

127

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“…The reducing power of M3MG was studied by measuring the reduction of Cu 2 + to Cu + . As shown in Figure 3, a concentration-dependent reducing power was demonstrated and the result obtained for gallic acid was similar to that reported before by Yoshino et al 28 As with the radical-scavenging study, the effect of M3MG as a reducing potential was less pronounced than with gallic acid. In agreement with the previous preliminary antioxidant assessment of synthetic M3MG, 21 the present study revealed that the loss of the C-3 free hydroxyl and acid functional groups of gallic acid through methylation reduces its antioxidant potential in these in vitro assay systems.…”

Section: Radical-scavenging and Reducing-power Effectssupporting

confidence: 89%

“…This finding agreed with previous studies in which prooxidative calf thymus DNA damage was reported for gallic acid. 28 Cytotoxicity of M3MG and gallic acid on SH-SY5Y neuronal cells…”

Section: Effects Of M3mg and Gallic Acid On Iros Levelmentioning

confidence: 99%

Methyl-3-O-Methyl Gallate and Gallic Acid from the Leaves of Peltiphyllum peltatum: Isolation and Comparative Antioxidant, Prooxidant, and Cytotoxic Effects in Neuronal Cells

Habtemariam

2011

Journal of Medicinal Food

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Methyl-3-O-methyl gallate (M3MG) is a rare natural product with close structural similarity to gallic acid. In the present report, the isolation of M3MG from Peltiphyllum peltatum leaves and its comparative antioxidant, prooxidant, and cytotoxicity to neuronal SH-SY5Y cells are discussed. When tested in concentrations up to 1 mM, M3MG consistently showed antioxidant activity without prooxidant effect both in cell and cell-free assay models. In contrast to M3MG, gallic acid showed a copper-dependent prooxidant effect that resulted in DNA damage, increased the level of intracellular reactive oxygen species, and induced cytotoxicity in neuronal cells. The identification of M3MG in P. peltatum leaves is furtherz evidence of the great antioxidant potential and nutritional value of the plant.

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“…185,186 There has been ample evidence claiming that gallates induce apoptosis selectively in fast growing tumor cells, leaving the healthy cells intact. 25,29,108,[185][186][187][188][189][190][191][192] This selective cytotoxicity towards cancer cells was proposed to be due to the ability of normal cells to resist GA induced apoptosis by the release of some inhibitors, unlike tumor cells which could not produce sufficient amounts of these inhibitors. 189 Thus, cancer cells are more sensitive towards GA induced apoptosis than normal healthy cells.…”

Section: As Anticancer Agentmentioning

confidence: 99%

Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications

2015

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Oxidative stress, a result of an overproduction and accumulation of free radicals, is the leading cause of several degenerative diseases such as cancer, atherosclerosis, cardiovascular diseases, ageing and inflammatory diseases. Polyphenols form an important class of naturally occurring antioxidants, having innumerable biological activities such as anticancer, antifungal, antibacterial, antiviral, antiulcer and anticholesterol, to name a few. Among various polyphenols, gallic acid (3,4,5-trihydroxybenzoic acid), a naturally occurring low molecular weight triphenolic compound, has emerged as a strong antioxidant and an efficient apoptosis inducing agent. Starting from the bioavailability and the biosynthetic pathway of gallic acid, this review includes various in vitro, in vivo and in silico studies providing the mode of action, radical scavenging activity, ability to inhibit lipid peroxidation, maintenance of endogenous defense systems and metal ion chelation by this triphenolic molecule, along with a comprehensive overview of factors responsible for its high antioxidant activity. Gallic acid derivatives have also been found in a number of phytomedicines with diverse biological and pharmacological activities, including radical scavenging, interfering with the cell signaling pathways and apoptosis of cancer cells. The diverse range of applications of this simple polyphenol is due to a fine amalgam between its antioxidant and prooxidant potential. The existing literature on this dual behavior of gallic acid and its derivatives is reviewed here. This is followed by an account of their potential clinical and industrial applications.

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Prooxidant action of gallic acid compounds: copper-dependent strand breaks and the formation of 8-hydroxy-2′-deoxyguanosine in DNA

Cited by 52 publications

References 16 publications

A review on DNA interaction with synthetic phenolic food additives

A review on DNA interaction with synthetic phenolic food additives

Methyl-3-O-Methyl Gallate and Gallic Acid from the Leaves of Peltiphyllum peltatum: Isolation and Comparative Antioxidant, Prooxidant, and Cytotoxic Effects in Neuronal Cells

Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications

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