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Investigation of the Antioxidant Properties of the Quaternized Chitosan Modified with a Gallic Acid Residue Using Peroxidase that Produces Reactive Oxygen Species

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Abstract

Chitosan modified with a (2-hydroxy-3-trimethylammonium) propyl group and gallic acid residue, or quaternized chitosan with gallic acid (QCG), was synthesized. Antioxidant properties of the produced QCG have been investigated. Peroxidase in combination with NADH and salicyl hydroxamate (SHAM) caused consumption of oxygen and production of H2O2 in aqueous solution as a result of O2 reduction in the peroxidase–oxidase reactions. The rates of O2 consumption and H2O2 generation were reduced in the presence of QCG. The antioxidant propyl gallate (PG) and superoxide dismutase (SOD) had the same effect, but not the quaternized chitosan (QC) without gallic acid. The effect of chitosan derivatives on the production of reactive oxygen species (ROS) in the cells of pea leaf epidermis and on the cell death detected by the destruction of cell nuclei, was investigated. QCG, QC, and SOD had no effect, while PG decreased the rate of ROS generation in the cells of the epidermis, which was induced by NADH with SHAM or by menadione. QCG and QC prevented destruction of the guard cell nuclei in the pea leaf epidermis that was caused by NADH with SHAM or by KCN. SOD had no effect on the destruction of nuclei, while the effect of PG depended on the inducer of the cell death. Suppression of the destruction of guard cell nuclei by chitosan derivatives was associated not with their antioxidant effect, but with the disruption of the plasma membrane of the cells. The results obtained have shown that QCG exhibits antioxidant properties in solutions, but does not prevent generation of ROS in the plant cells. The mechanism of antioxidant effect of QCG is similar to that of PG and SOD.

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Abbreviations

Amplex Red:

N-acetyl-3,7-dihydroxyphenoxazine

DCF:

2′,7′-dichlorofluorescein

DCFH-DA:

2′,7′-dichlorofluorescin diacetate

PG:

propyl gallate

PI:

propidium iodide

QC:

quaternized chitosan

QCG:

quaternized chitosan with gallic acid

ROS:

reactive oxygen species

SHAM:

salicyl hydroxamate

SOD:

superoxide dismutase

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Funding

The research was carried out as part of the Scientific Project of the State Order of the Government of Russian Federation to Lomonosov Moscow State University no. 121042600047-9, as well as in the frame of the Interdisciplinary Scientific and Educational School of Moscow University “Molecular Technologies of the Living Systems and Synthetic Biology”. Preparation and analysis of the chitosan derivatives was partially supported by the Russian Foundation for Basic Research (project no. 20-016-00205).

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Authors and Affiliations

  1. Department of Immunology, Faculty of Biology, Lomonosov Moscow State University, 119234, Moscow, Russia

    Dmitry B. Kiselevsky & Vitaly D. Samuilov

  2. Laboratory of Biopolymer Engineering, Skryabin Institute of Bioengineering, Research Center of Biotechnology, Russian , 119071, Moscow, Russia

    Alla V. Il’ina, Alexey P. Lunkov & Valery P. Varlamov

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  1. Dmitry B. Kiselevsky
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  2. Alla V. Il’ina
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  3. Alexey P. Lunkov
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  4. Valery P. Varlamov
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  5. Vitaly D. Samuilov
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Correspondence to Dmitry B. Kiselevsky.

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The authors declare no conflicts of interests in financial or any other sphere. This article does not contain any studies with human participants or animals performed by any of the authors.

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Kiselevsky, D.B., Il’ina, A.V., Lunkov, A.P. et al. Investigation of the Antioxidant Properties of the Quaternized Chitosan Modified with a Gallic Acid Residue Using Peroxidase that Produces Reactive Oxygen Species. Biochemistry Moscow 87, 141–149 (2022). https://doi.org/10.1134/S0006297922020067

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