Effect of ionizing radiation on the stereochemical composition of dihydroquercetin sample

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Abstract

Introduction. Microbiological quality is one of the key criteria for active pharmaceutical ingredients. To ensure it, a set of preventive measures and various decontamination methods are used. A relatively new approach is ionizing radiation, characterized by high efficiency. However, according to the literature, during ionizing sterilization, a change in the chemical composition of the drug may occur, which requires studying the effect of the radiation factor on each individual compound.

Objective. To investigate the effect of ionizing radiation on the stereoisomeric composition of the dihydroquercetin (DHQ), a natural flavananol and a promising object for the development of chiral remedies.

Material and methods. The object of the study is a sample of DHQ exposed to ionizing radiation of 9.5 MeV (DHQrad), while the reference sample is a native substance of DHQ from the same manufacturer and batch (DHQref). Analysis was conducted using polarimetry and reversed-phase HPLC with diode array and mass spectrometric detection.

Results. Taking into account the moisture content of the samples, the average values of the specific optical rotation for acetone solutions of DHQrad and DHQref were 20.85±1.54° and 19.65±1.93°, respectively. Chromatograms showed two peaks with retention times of 10.18±0.03 and 11.63±0.01 min, which, based on UV and mass spectra profiles, were identified as trans- and cis-diastereomers of DHQ. The total content of flavananol in the analyzed samples was 93.25±0.01% for DHQrad and 94.92±0.01% for DHQref, with the amount of the cis-isomer being 0.59±0.13% and 1.27±0.70%, respectively.

Conclusion. The study did not establish a significant effect of ionizing radiation on the specific optical rotation value and the stereoisomeric composition of the DHQ substance. The findings support the recommendation of this sterilization method for remedies containing the studied flavananol.

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About the authors

Denis I. Pankov

I.M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)

Email: pankov_d_i@staff.sechenov.ru
ORCID iD: 0009-0007-6195-6400

Assistant of the Department of Chemistry of the Institute of Pharmacy named after A.P. Nelyubin

Russian Federation, Moscow

Maria D. Korochkina

I.M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)

Email: korochkina_m_d@student.sechenov.ru
ORCID iD: 0000-0002-2790-9041

Student of the Institute of Pharmacy named after A.P. Nelyubin

Russian Federation, Moscow

Roman P. Terekhov

I.M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)

Email: terekhov_r_p@staff.sechenov.ru
ORCID iD: 0000-0001-9206-8632

Doctor of Pharmaceutical Sciences, Associate Professor of the Department of Chemistry of the Institute of Pharmacy named after A.P. Nelyubin

Russian Federation, Moscow

Margarita A. Tokareva

I.M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)

Email: tokareva_m_a@student.sechenov.ru
ORCID iD: 0000-0001-7684-358X

Postgraduate Student of the Department of Pharmaceutical and Toxicological Chemistry named after A.P. Arzamastsev of the Institute of Pharmacy named after A.P. Nelyubin

Russian Federation, Moscow

Evgeny S. Melnikov

I.M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University); City Clinical Hospital named after I.V. Davydovsky, Moscow Department of Healthcare

Email: melnikov_e_s@staff.sechenov.ru
ORCID iD: 0000-0002-8993-4808

Candidate of Pharmaceutical Sciences, Associate Professor of the Department of Pharmaceutical and Toxicological Chemistry named after A.P. Arzamastsev of the Institute of Pharmacy named after A.P. Nelyubin

Russian Federation, Moscow; Moscow

Tatyana A. Rodina

City Clinical Hospital named after I.V. Davydovsky, Moscow Department of Healthcare

Email: semina_tatiana@mail.ru
ORCID iD: 0000-0002-0528-3068

Candidate of Chemical Sciences, Consulting Chemist at the Laboratory of Pharmacokinetics of the Centre of Personalized Medicine

Russian Federation, Moscow

Irina A. Selivanova

I.M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)

Author for correspondence.
Email: selivanova_i_a@staff.sechenov.ru
ORCID iD: 0000-0002-2244-445X

Doctor of Pharmaceutical Sciences, Professor of the Department of Chemistry of the Institute of Pharmacy named after A.P. Nelyubin

Russian Federation, Moscow

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2. Fig. 1. Structure of DHQ

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3. Fig. 2. Dependency graph of optical rotation value towards time for DHQ solutions in acetone

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4. Fig. 3. Chromatograms of tested samples: а – DHQrad, б – DHQref

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