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9. Imine resveratrol analogs (IRAs): The strong antioxidant that can protect lymphocytes from oxidative damage.

Author

Kubalová, Ivona, Šeršeň, František, Gálová, Eliška, and Filo, Juraj

Subjects
RESVERATROL, LYMPHOCYTES, BIOLOGICAL assay, HYDROXYL group, IMINE derivatives
Abstract

Imine resveratrol analogs (IRAs) are promising new agents that can have higher positive effects and, simultaneously, lower negative properties than resveratrol. In this study, three imine hydroxy derivatives (2‐((4‐hydroxyphenylimino) methyl) phenol [IRA1], 3‐((4‐hydroxyphenylimino) methyl) phenol [IRA2], and 4‐((4‐hydroxyphenylimino) methyl) phenol [IRA3]) were prepared and tested in several biological assays. They performed superior to resveratrol in several antioxidant and biological assays, showing high antioxidant capacity and low genotoxicity. Ferric reducing antioxidant power assay (FRAP) and hydroxyl radicals scavenging assay revealed good Fe3+ to Fe2+ reduction and strong inhibition of hydroxyl radical formation, respectively. High dosage (1 mmol/dm3) of IRA2 and IRA3 did not cause genotoxicity in human lymphocytes. Moreover, lymphocytes pretreated with all three IRAs accumulated only very few DNA breaks induced by H2O2 than lymphocytes pretreated with resveratrol. Additionally, the number of detected DNA breaks appearing after removal of damaged DNA bases, 8‐oxo‐7,8‐dihydroguanine (8‐oxoG), did not dramatically increase in lymphocytes treated with IRA2. Thus, we concluded that IRAs, especially IRA2, are strong antioxidants with the ability to protect lymphocytes from oxidative damage. [ABSTRACT FROM AUTHOR]

Published
2022
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11. Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives

Author

Šeršeň, František, Gregáň, Fridrich, Peško, Matúš, Dvoranová, Dana, Král’ová, Katarína, Matkovičová, Zuzana, Gregáň, Juraj, and Donovalová, Jana

Subjects
Chloroplasts, photosynthesis inhibition, N′-[2,6-dinitro-4-[trifluoromethyl)phenyl]hydrazonoyl derivatives, Herbicides, Electron Spin Resonance Spectroscopy, Hydrazones, Chlorella, green algae, Article, Electron Transport, lcsh:QD241-441, Inhibitory Concentration 50, N′-[2,6-dinitro-4-(trifluoromethyl)phenyl]hydrazides, Hydrazines, Spectrometry, Fluorescence, lcsh:Organic chemistry, Spinacia oleracea, spinach chloroplasts, Photosynthesis
Abstract

Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

Published
2015

14. The Scavenging of DPPH, Galvinoxyl and ABTS Radicals by Imine Analogs of Resveratrol

Author

Kotora, Peter, Šeršeň, František, Filo, Juraj, Loos, Dušan, Gregáň, Juraj, and Gregáň, Fridrich

Subjects
Molecular Structure, endocrine system diseases, organic chemicals, Biphenyl Compounds, food and beverages, antioxidant activity, Free Radical Scavengers, Article, lcsh:QD241-441, resveratrol analogs, Picrates, lcsh:Organic chemistry, Resveratrol, iminophenols, Stilbenes, Benzothiazoles, Benzhydryl Compounds, Sulfonic Acids, skin and connective tissue diseases, hormones, hormone substitutes, and hormone antagonists
Abstract

Resveratrol (3,5,4'-trihydroxystilbene) is a phytoalexin produced by plants. Resveratrol is known for its anti-cancer, antiviral and antioxidant properties. We prepared imine analogs of resveratrol ((hydroxyphenyliminomethyl)phenols) and tested their antioxidant activity. All prepared resveratrol analogs were able to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical (GOR) and 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS) radicals. The antioxidant activity efficiency correlated with the number and position of hydroxyl groups. The most effective antioxidants were resveratrol analogs containing three hydroxyl groups in the benzylidene part of their molecules. These results provide new insights into the relationship between the chemical structure and biological activity of resveratrol analogs.

Published
2016

31. BIO-REMEDIATION BY NATURAL ZEOLITE ON PLANTS CULTIVATED IN A HEAVY METAL-CONTAMINATED MEDIUM.

Author

Šeršeň, František, Čilk, Gabriel, Havránek, Emil, and Sýkorová, Miroslava

Abstract

Natural zeolitic tuff from the deposit of Nižný Hrabovec (Slovakia) is capable to protect plants against toxic effects of heavy metals. This protective effect was manifested by hydroponical growth of maize in Knop's nutrition medium contaminated by copper, mercury or cadmium chlorides. The use of 6.7 g zeolitic tuff per L of Knop's nutrition medium polluted with 30 pimol of Cu, Cd or Hg resulted in almost 100 % restoration of plant growth, as far as the plant size and dry matter (DM) are concerned. It was found that the heavy metals are absorbed and disposed mainly by maize roots. However, a considerable amount of cadmium has been distributed into the plant's shoots and leaves (140 mg Cd per kg DM of each). This feature of the maize could be utilized for phytoremediation of Cd-contaminated soils after the verification of this effect at long-term experiments. [ABSTRACT FROM AUTHOR]

Published
2005

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