New cytokinin derivatives possess UVA and UVB photoprotective effect on human skin cells and prevent oxidative stress

Hönig, Martin; Plíhalová, Lucie; Spíchal, Lukáš; Grúz, Jiří; Kadlecová, Alena; Voller, Jiří; Svobodová, Alena Rajnochová; Vostalová, Jitka; Ulrichová, Jitka; Doležal, Karel; Strnad, Miroslav

doi:10.1016/j.ejmech.2018.03.043

Cited by 22 publications

(13 citation statements)

References 35 publications

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“…With some exceptions, compounds with a 9-(tetrahydropyran-2-yl) protective group exhibited even lower activity in the WLSA than their THF deprotected analogues [47]. This observation is in contrast to previous studies, in which the introduction of 9-THP or 9-THF protective groups was found to not decrease the antisenescent activity of the corresponding free bases [37,40,45,48].…”

Section: Antisenescent and Antioxidant Activity Of C2 C8 And N9 Pcontrasting

confidence: 59%

“…The addition of chlorine at the C2 atom of purine moiety lowered or completely reduced the antisenescent activity of the prepared compounds. Furthermore, the prolongation of the C-bridge carrying the N6-substituent of 6-(2-thiophen-2-ylethyl)aminopurine led to the complete loss of the antisenescent activity in the WLSA [45].…”

Section: Antisenescent and Antioxidant Activity Of C2 C8 And N9 Pmentioning

confidence: 99%

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Role of Cytokinins in Senescence, Antioxidant Defence and Photosynthesis

Hönig

Plíhalová

Husičková

et al. 2018

IJMS

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167

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Cytokinins modulate a number of important developmental processes, including the last phase of leaf development, known as senescence, which is associated with chlorophyll breakdown, photosynthetic apparatus disintegration and oxidative damage. There is ample evidence that cytokinins can slow down all these senescence-accompanying changes. Here, we review relationships between the various mechanisms of action of these regulatory molecules. We highlight their connection to photosynthesis, the pivotal process that generates assimilates, however may also lead to oxidative damage. Thus, we also focus on cytokinin induction of protective responses against oxidative damage. Activation of antioxidative enzymes in senescing tissues is described as well as changes in the levels of naturally occurring antioxidative compounds, such as phenolic acids and flavonoids, in plant explants. The main goal of this review is to show how the biological activities of cytokinins may be related to their chemical structure. New links between molecular aspects of natural cytokinins and their synthetic derivatives with antisenescent properties are described. Structural motifs in cytokinin molecules that may explain why these molecules play such a significant regulatory role are outlined.

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Section: Antisenescent and Antioxidant Activity Of C2 C8 And N9 Pcontrasting

confidence: 59%

Section: Antisenescent and Antioxidant Activity Of C2 C8 And N9 Pmentioning

confidence: 99%

Role of Cytokinins in Senescence, Antioxidant Defence and Photosynthesis

Hönig

Plíhalová

Husičková

et al. 2018

IJMS

Self Cite

167

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“…In view of the above structure-activity relationships resulting from the synthesis and testing of various 9-substituted ArCKs, new 9-substituted Kin derivatives were prepared and their antisenescence activity in WLS assays was investigated [ 176 ]. Seven Kin derivatives and analogues were prepared via nucleophilic substitution of 6-chloro-9-(tetrahydrofuran-2-yl)purine or 2,6-dichloro-9-(tetrahydrofuran-2-yl)purine with the appropriate amines.…”

Section: Non-sugar N9-substituted Cytokininsmentioning

confidence: 99%

Naturally Occurring and Artificial N9-Cytokinin Conjugates: From Synthesis to Biological Activity and Back

et al. 2020

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Cytokinins and their sugar or non-sugar conjugates are very active growth-promoting factors in plants, although they occur at very low concentrations. These compounds have been identified in numerous plant species. This review predominantly focuses on 9-substituted adenine-based cytokinin conjugates, both artificial and endogenous, sugar and non-sugar, and their roles in plants. Acquired information about their biological activities, interconversions, and metabolism improves understanding of their mechanisms of action and functions in planta. Although a number of 9-substituted cytokinins occur endogenously, many have also been prepared in laboratories to facilitate the clarification of their physiological roles and the determination of their biological properties. Here, we chart advances in knowledge of 9-substituted cytokinin conjugates from their discovery to current understanding and reciprocal interactions between biological properties and associated structural motifs. Current organic chemistry enables preparation of derivatives with better biological properties, such as improved anti-senescence, strong cell division stimulation, shoot forming, or more persistent stress tolerance compared to endogenous or canonical cytokinins. Many artificial cytokinin conjugates stimulate higher mass production than naturally occurring cytokinins, improve rooting, or simply have high stability or bioavailability. Thus, knowledge of the biosynthesis, metabolism, and activity of 9-substituted cytokinins in various plant species extends the scope for exploiting both natural and artificially prepared cytokinins in plant biotechnology, tissue culture, and agriculture.

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“…Modulation of endogenous levels of CKs can be achieved by their exogenous application. However, such disturbance of endogenous CK homeostasis usually stimulates degradation and deactivation mechanisms, especially in the absence of the protective moiety of the exogenous CK (e.g., tetrahydropyranyl or tetrahydrofuranyl; Honig et al, 2018). The other possibility is to insert the CK biosynthetic gene isopentenyltransferase under suitable promoter (e.g., Skalak et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Heat Acclimation and Inhibition of Cytokinin Degradation Positively Affect Heat Stress Tolerance of Arabidopsis

et al. 2020

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In order to pinpoint phytohormone changes associated with enhanced heat stress tolerance, the complex phytohormone profiles [cytokinins, auxin, abscisic acid (ABA), jasmonic acid (JA), salicylic acid and ethylene precursor 1-aminocyclopropane-1carboxylic acid (ACC)] were compared in Arabidopsis thaliana after direct heat shock (45°C, 3 h) and in heat-stressed pre-acclimated plants (1 h at 37°C followed by 2 h at optimal temperature 20°C). Organ-specific responses were followed in shoot apices, leaves, and roots immediately after heat shock and after 24-h recovery at 20°C. The stress strength was evaluated via membrane ion leakage and the activity of nicotinamide adenine dinucleotide phosphate (NADPH) oxidases (NOX) and antioxidant enzymes [superoxide dismutases, guaiacol peroxidases (POD), catalases, ascorbate peroxidases (APX)]. Heat acclimation diminished negative effects of heat stress, especially in apices and roots, no significant differences being observed in leaves. Low NOX1-3 activities indicated diminished production of reactive oxygen species. Higher activity of APX, POD1, and the occurrence of POD3-4 reflected acclimation-stimulated readiness of the antioxidant system. Acclimation diminished heat shock-induced changes of ABA, JA, cytokinin, and auxin levels in apices. Excess of ABA catabolites suggested an early stress response. The strong up-regulation of ABA and ACC in roots indicated defense boost in roots of acclimated plants compared to the non-acclimated ones. To evaluate the possibility to enhance stress tolerance by cytokinin pool modulation, INCYDE-F, an inhibitor of cytokinin oxidase/dehydrogenase, was applied. As cytokinin effects on stress tolerance may depend on timing of their regulation, INCYDE was applied at several time-points. In combination with acclimation, INCYDE treatment had a slight positive effect on heat stress tolerance, mainly when applied after 2-h period of the optimal temperature. INCYDE increased contents of cytokinins trans-zeatin and cis-zeatin in roots and auxin in all tissues after heat shock. INCYDE also helped to suppress the content of ABA in leaves, and ethylene in apices and roots. INCYDE application to non-acclimated plants (applied before Frontiers in Plant Science | www.frontiersin.org or after heat shock) strengthened negative stress effects, probably by delaying of the repair processes. In conclusion, pre-treatment with moderately elevated temperature enhanced heat stress tolerance and accelerated recovery after stress. Inhibition of cytokinin degradation by INCYDE slightly improved recovery of acclimated plants.

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New cytokinin derivatives possess UVA and UVB photoprotective effect on human skin cells and prevent oxidative stress

Cited by 22 publications

References 35 publications

Role of Cytokinins in Senescence, Antioxidant Defence and Photosynthesis

Role of Cytokinins in Senescence, Antioxidant Defence and Photosynthesis

Naturally Occurring and Artificial N9-Cytokinin Conjugates: From Synthesis to Biological Activity and Back

Heat Acclimation and Inhibition of Cytokinin Degradation Positively Affect Heat Stress Tolerance of Arabidopsis

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