Pro-oxidant activity of polyphenols and its implication on cancer chemoprevention and chemotherapy

León‐González, Antonio J.; Auger, Cyril; Schini‐Kerth, Valérie B.

doi:10.1016/j.bcp.2015.07.017

Cited by 238 publications

(178 citation statements)

References 111 publications

(104 reference statements)

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“…Similar pro-oxidant action has been observed for other seed meals, e.g., rapeseed (Szydùowska-Czerniak and Ùaszewska, 2015). It was postulated that particularly polyphenols with a dual antioxidant-pro-oxidant role could act as selective cytotoxic agents against cancer cells (León-González et al, 2015). Despite similar action of free radicals, correlation was not observed in IC 50 values between DPPH and GO assays.…”

Section: Discussionmentioning

confidence: 52%

Antioxidant Properties of Camelina sativa Oil and Press-Cakes

Mieriņa

Adere

Krasauska

et al. 2017

Proceedings of the Latvian Academy of Sciences. Section B. Natural, Exact, and Applied Sciences.

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Camelina sativa is well known due to high content of polyunsaturated fatty acids in its oil. Till now this oil has been studied mainly for applications as raw material for synthesis of resins, biodiesel and hydrocarbon fuels. This study examines the oxidative stability of cold-pressed Camelina sativa (also known as camelina, false flax or gold-of-pleasure) oil and its extracts of spices. Despite the high content of polyunsaturated fatty acids, Camelina sativa oil appeared more rigid against oxidation than rapeseed or flax oil. Extracts of different spices were prepared by maceration in camelina oil at room temperature for 24 h. The stability of extracts was determined under accelerated oxidation conditions and monitored by peroxide values. Most of the tested additives (e.g., bay leaves, allspice, clove, barley sprouts, coriander, ginger) did not influence or even decreased oxidative stability of the oil. However, oil with thyme additive demonstrated remarkably higher stability then Camelina sativa oil alone. Press-cakes of camelina seeds were extracted with two polar solvents (ethanol or water) and their mixtures under variable conditions (room temperature or reflux). Prepared polar extracts of press-cakes were characterised by total polyphenol content (Folin–Ciocalteu method) and antiradical activity against 1,1-diphenyl-2-picryl hydrazyl and galvinoxyl.

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Section: Discussionmentioning

confidence: 52%

Antioxidant Properties of Camelina sativa Oil and Press-Cakes

Mieriņa

Adere

Krasauska

et al. 2017

Proceedings of the Latvian Academy of Sciences. Section B. Natural, Exact, and Applied Sciences.

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“…High doses of antioxidants selectively kill cancer cells also because of pro-oxidative effects. Because the endogenous ROS production is high due to the high metabolic activity of cancer cells, they can cause selective damage and death of cancer cells with a cumulative effect, along with the pro-oxidant activity caused by high-dose antioxidants (44). Therefore, it is very important to determine the preventive and therapeutic doses of antioxidants.…”

Section: Exogenous Antioxidants and Cancermentioning

confidence: 99%

Exogenous Antioxidants are Double-edged Swords

Koçyiğit¹,

Selek²

2016

Bezmialem Science

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Oxidant-antioxidant balance is crucially important in maintaining healthy biological systems. Under physiological conditions, the human antioxidative defense system, including superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH-Px), and glutathione (GSH), allows the elimination of excess reactive oxygen species (ROS), including superoxide anions (O 2 . ), hydroxyl radicals (HO .), and alkoxyl radicals (RO .). In addition, exogenous compounds with reducing capacity, such as vitamin C, vitamin E, carotenoids, and polyphenols are also essential for intact functioning of endogenous antioxidant defense system. Therefore, there is continuous demand for exogenous antioxidants to prevent oxidative stress. However, higher doses of isolated compounds could act as pro-oxidant either by presenting direct pro-oxidant behavior or by interfering with the normal doses of ROS that is required for normal cell functioning. In this review, synthetic antioxidants among supplementary antioxidants, fruit-rich nutrition and various supplementary products to strengthen our body will be considered and discussed under the light of experimental and epidemiological evidence. Antioxidants in physiological dose ranges are considered to be safe in healthy people and overdoses cause damage via pro-oxidative effects; therefore, the importance of doses of antioxidants, the lower preventive doses that protect healthy individuals from illnesses, and higher therapeutic doses that treat cancer patients will be emphasized in this review.

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“…Among the main mechanisms invoked to explain the biological activities of this kind of molecules are those involving free radicals [21][22][23]. It has been previously shown that the reduction potentials of this kind of molecules, which present a α,β-unsaturated ketone moiety, can affect directly their biological activity [24,25].…”

Section: Radical Anions and Electron Affinitiesmentioning

confidence: 99%

“…In dipole-bound anions, the SOMO is distributed in a limited part of the molecule, while in valence-bound anions the SOMO is distributed over the whole molecule. In Figure 3, the SOMO of adiabatic and vertical anions for molecules 1 (representative example for series 1-6) and 7 (representative example for series 7-12), are displayed (others are presented in Figure S3 Among the main mechanisms invoked to explain the biological activities of this kind of molecules are those involving free radicals [21][22][23]. It has been previously shown that the reduction potentials of this kind of molecules, which present a α,β-unsaturated ketone moiety, can affect directly their biological activity [24,25].…”

Section: Radical Anions and Electron Affinitiesmentioning

confidence: 99%

A Computational Study of Structure and Reactivity of N-Substitued-4-Piperidones Curcumin Analogues and Their Radical Anions

2016

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In this work, a computational study of a series of N-substitued-4-piperidones curcumin analogues is presented. The molecular structure of the neutral molecules and their radical anions, as well as their reactivity, are investigated. N-substituents include methyl and benzyl groups, while substituents on the aromatic rings cover electron-donor and electron-acceptor groups. Substitutions at the nitrogen atom do not significantly affect the geometry and frontier molecular orbitals (FMO) energies of these molecules. On the other hand, substituents on the aromatic rings modify the distribution of FMO. In addition, they influence the capability of these molecules to attach an additional electron, which was studied through adiabatic (AEA) and vertical electron affinities (VEA), as well as vertical detachment energy (VDE). To study electrophilic properties of these structures, local reactivity indices, such as Fukui (f + ) and Parr (P + ) functions, were calculated, and show the influence of the aromatic rings substituents on the reactivity of α,β-unsaturated ketones towards nucleophilic attack. This study has potential implications for the design of curcumin analogues based on a 4-piperidone core with desired reactivity.

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Pro-oxidant activity of polyphenols and its implication on cancer chemoprevention and chemotherapy

Cited by 238 publications

References 111 publications

Antioxidant Properties of Camelina sativa Oil and Press-Cakes

Antioxidant Properties of Camelina sativa Oil and Press-Cakes

Exogenous Antioxidants are Double-edged Swords

A Computational Study of Structure and Reactivity of N-Substitued-4-Piperidones Curcumin Analogues and Their Radical Anions

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