Prooxidant activity of hydroxycinnamic acids on DNA damage in the presence of Cu(II) ions: Mechanism and structure–activity relationship

Zheng, Liqin; Dai, Fang; Zhou, Bo; Yang, Li; Liu, Zhongli

doi:10.1016/j.fct.2007.07.010

Cited by 105 publications

(79 citation statements)

References 44 publications

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“…This effect is in part attributed to their antioxidant properties. However, studies have shown that caffeic acid can also trigger DNA degradation in the presence of cupper ions due to its pro-oxidant activity (35,37). Caffeic acid, a PASR inducer like ferulic and pcoumaric acids, has a strong pro-oxidant effect due to the presence of an ortho-dihydroxyl group that chelates O 2 with Cu 2ϩ ions and generates reactive oxygen species, which are responsible for the DNA damage.…”

Section: Discussionmentioning

confidence: 99%

“…Their specific structure confers important biological activities. They have free radical scavenging properties that can trigger antimutagenetic effects (14) but that can also lead to pro-oxidant DNA degradation mediated by divalent cations (37). Recently, it was shown that some phenolic acids that induce the phenolic acid stress response (PASR) in grampositive bacteria regulate the expression of genes of the type III secretion system required for virulence by the plant pathogen bacterium Dickeya dadantii (23).…”

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confidence: 99%

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Inactivation of PadR, the Repressor of the Phenolic Acid Stress Response, by Molecular Interaction with Usp1, a Universal Stress Protein fromLactobacillus plantarum, inEscherichia coli

Gury

Seraut

Tran

et al. 2009

Appl Environ Microbiol

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The phenolic acid decarboxylase gene padA is involved in the phenolic acid stress response (PASR) in gram-positive bacteria. In Lactobacillus plantarum, the padR gene encodes the negative transcriptional regulator of padA and is cotranscribed with a downstream gene, usp1, which encodes a putative universal stress protein (USP), Usp1, of unknown function. The usp1 gene is overexpressed during the PASR. However, the role and the mechanism of action of the USPs are unknown in gram-positive bacteria. Therefore, to gain insights into the role of USPs in the PASR; (i) a usp1 deletion mutant was constructed; (ii) the two genes padR and usp1 were coexpressed with padA under its own promoter as a reporter gene in Escherichia coli; and (iii) molecular in vitro interactions between the PadR, Usp1, and the padA promoter were studied. Although the usp1 mutant strain retained phenolic acid-dependent PAD activity, it displayed a greater sensitivity to strong acidic conditions compared to that of the wild-type strain. PadR cannot be inactivated directly by phenolic acid in E. coli recombinant cultures but is inactivated by Usp1 when the two proteins are coexpressed in E. coli. The PadR inactivation observed in recombinant E. coli cells was supported by electrophoretic mobility shift assays. Although Usp1 seems not to be absolutely required for the PASR, its capacity to inactivate PadR indicates that it could serve as an important mediator in acid stress response mechanisms through its capacity to interact with transcriptional regulators.

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

Inactivation of PadR, the Repressor of the Phenolic Acid Stress Response, by Molecular Interaction with Usp1, a Universal Stress Protein fromLactobacillus plantarum, inEscherichia coli

Gury

Seraut

Tran

et al. 2009

Appl Environ Microbiol

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“…HCAs have the ability to act as pro-oxidants in systems containing redox-active metals [158,159]. Redox cycling of HCAs can be catalyzed by transition metals in the presence of oxygen, producing organic radicals along with ROS that may damage biological macromolecules [160].…”

Section: Pro-oxidant Effects Of Hydroxycinnamic Acidsmentioning

confidence: 99%

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

159

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Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxi-dant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the car-boxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activ-ity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimiza-tion of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be use-ful for management of oxidative stress-related diseases.Keywords: Antioxidant, hydroxycinnamic acids, in vitro, ROS, structure-activity relationships. OXIDATIVE STRESS AND ANTIOXIDANTSReactive oxygen species (ROS) are oxygen derived molecules that readily react with other compounds and macromolecules and oxidize them. Some representative exam-ples of these species include superoxide (O2•-), hydroxy (HO • ) and peroxy (ROO • ) radicals, hydrogen peroxide (H2O2) and singletROS are involved in important physiological processes such as immune response, gene expression, signal transduc-tion and growth regulation [5,6]; however if they are not kept under tight control by physiological antioxidant systems they will be able to oxidize and damage various biological molecules leading to a condition called oxidative stress [1,7,8]. In this regard, oxidative stress has been reported to be in-volved in the pathogenesis of diseases such as cancer [9], neurodegenerative diseases [10], stroke [11], and others [12,13].Since an important source of ROS comes from environment [14], with the industrial development and the change in life style, oxidative stress related diseases need a special attention [15].Antioxidants operate by preventing or slowing the progression of oxidative damage reactions [16,17]. An antioxidant has been defined as "any substance that delays, p...

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“…Previous study showed that phytochemicals depletes intracellular antioxidants there by induced cancer cell death [33,34] . Diogenin a plant derived steroid and cumarin possess an effective pro-oxidant activity in cancer cell line by decreasing antioxidant and enhancing lipid peroxidation [35,36] . Our results also correlate with the above finding.…”

Section: Discussionmentioning

confidence: 99%

Chemotherapeutic potiential of Lupeol and its analogue (oxime) on human mammary cancer cell line (MCF-7)

Gunasekaran

Mirunalini

2017

Prog Biosci Bioeng

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Lupeol, a dietary triterpene, present in fruits and medicinal plants, has been reported to possess pharmacological properties including anticancer activities both in vitro and in vivo. The present study investigates the anti-cancer activity and the underlying mechanisms human mammary cancer (MCF-7). We observed increased levels of antioxidants (ABTS, DPPH, superoxide anions radical scavenging activity and hydroxyl radical scavenging activity) in MCF-7 cell line. The higher concentrations of lupeol analogues significantly increased cytotoxicity in MCF-7 cells. The IC 50 value was found to be 40 µM/mL of lupeol analogue (oxime) could greatly inhibit the cell growth. So, we have chosen at 40 and 320 µM/mL concentration of lupeol analogue (oxime) for further experiments. We observed increased levels of Lipid peroxidation and decreased levels of Antioxidants (SOD, CAT, GPx and GSH) in MCF-7 cell line because of the pro oxidant mechanism of lupeol analogue (oxime). These observations revealed the cytotoxic potential of lupeol, which could be attributed to their pro oxidant property on the MCF-7 cells. It is evident from the observation made in the present study that the lupeol analogue (oxime) has potential anticancer effect compared to Lupeol.

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Prooxidant activity of hydroxycinnamic acids on DNA damage in the presence of Cu(II) ions: Mechanism and structure–activity relationship

Cited by 105 publications

References 44 publications

Inactivation of PadR, the Repressor of the Phenolic Acid Stress Response, by Molecular Interaction with Usp1, a Universal Stress Protein fromLactobacillus plantarum, inEscherichia coli

Inactivation of PadR, the Repressor of the Phenolic Acid Stress Response, by Molecular Interaction with Usp1, a Universal Stress Protein fromLactobacillus plantarum, inEscherichia coli

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Chemotherapeutic potiential of Lupeol and its analogue (oxime) on human mammary cancer cell line (MCF-7)

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