Нажмите на эту строку чтобы перейти к Новостям сайта "Русский врач"

Перейти
на сайт
журнала
"Врач"
Перейти на сайт журнала "Медицинская сестра"
Перейти на сайт журнала "Фармация"
Перейти на сайт журнала "Молекулярная медицина"
Перейти на сайт журнала "Вопросы биологической, медицинской и фармацевтической химии"
Журнал включен в российские и международные библиотечные и реферативные базы данных

ВАК (Россия)
РИНЦ (Россия)
Эко-Вектор (Россия)

OBTAINING A WORKING STANDARD SAMPLE OF CHALCONE BUTEINE AND ITS QUANTITATIVE DETERMINATION IN PLANT RAW MATERIALS

DOI: https://doi.org/10.29296/25877313-2024-01-03
Issue: 
1
Year: 
2024

E.O. Kulichenko
Senior Lecturer, Department of Biological Chemistry,
Pyatigorsk Medical Pharmaceutical Institute – Branch of Volgograd State Medical University (Pyatigorsk, Russia)
E-mail: evgenia.kuli4encko@yandex.ru
E.T. Oganesyan
Dr.Sc. (Pharm.), Professor, Head of the Department of Organic Chemistry,
Pyatigorsk Medical Pharmaceutical Institute – Branch of Volgograd State Medical University (Pyatigorsk, Russia)
S.V. Pechinskii
Ph.D. (Pharm.), Docent, Department of Pharmaceutical Chemistry,
Pyatigorsk Medical Pharmaceutical Institute – Branch of Volgograd State Medical University (Pyatigorsk, Russia)
A.G. Kuregyan
Dr.Sc. (Pharm.), Professor, Department of Pharmaceutical Chemistry,
Pyatigorsk Medical Pharmaceutical Institute – Branch of Volgograd State Medical University (Pyatigorsk, Russia)
M.V. Larsky
Ph.D. (Pharm.), Docent, Department of Pharmaceutical Chemistry,
Pyatigorsk Medical Pharmaceutical Institute – Branch of Volgograd State Medical University (Pyatigorsk, Russia)
A.P. Pleten
Dr.Sc. (Biol.), Professor of the Department of Biological Chemistry,
Moscow State Medical and Dental University named after A.I. Evdokimov
of the Ministry of Health of the Russian Federation (Moscow, Russia)
A.A. Prokopov
Dr.Sc. (Chem.), Associate Professor, Head of the Department of General and Bioorganic Chemistry,
Moscow State Medical and Dental University named after A.I. Evdokimov
of the Ministry of Health of the Russian Federation (Moscow, Russia)
T.Yu. Tatarenko-Kozmina
Dr.Sc. (Biol.), Professor, Head of Department of Medical Biology with the Fundamentals of Cellular and Molecular Biotechnology,
Scientific Research Institute of Clinical Medicine named after Semashko,
Moscow State Medical and Dental University named after A.I. Evdokimov
of the Ministry of Health of the Russian Federation (Moscow, Russia)

Introduction. Butein ‒ 2',4',3,4-tetrahydroxychalcone is found in a number of plants that have a pronounced antimicrobial and antifungal effect: Butea monosperma Lam., hairy string ‒ Bidens pilosa L., tripartite string ‒ Bidens tripartita L., hydrophytum ‒ Hydnophytum formicarum Jack., early thyme ‒ Thymus praecox. Butein is not the dominant representative of the flavonoid class in plants, but it can serve as a marker compound for the analysis of raw materials containing this chalcone. The purpose of the study is to synthesize and analyze a working standard sample of butein, as well as to develop a method for its quantitative determination in Cosmos bipinnate raw materials using solid-phase extraction. Material and methods. Butein synthesis was carried out using the Claisen‒Schmidt reaction, the yield was 44,4%. Identification of the obtained butein was carried out using UV, IR and Mass spectroscopy. Quantitative determination of butein in the raw materials of Cosmos doubly persita was carried out by HPLC in combination with solid-phase extraction. Results. The results obtained confirm that the test sample is butein (2',4',3,4-tetrahydroxychalcone). To determine butein in plant raw materials, a standard sample of this compound should be available, and therefore the substance of this chalcone was synthesized and on its basis, according to the state pharmacopoeia, a working standard sample was obtained (butein content in it is 99,62%). Identification of butein by HPLC was carried out by the retention time, which in the chromatogram of the test solution is 160,70 min, in the chromatogram of the standard solution – 160,07 min  2%. The butein content in the flowers of the cosmos bipinnate we studied in terms of dry raw materials is 0,043%  2%. Conclusions. The synthesis of chalcone ‒ butein was carried out by alkaline condensation of resacetophenone with protocatechuic aldehyde. The yield of butein is 5,95  0,0195 g (44,4%). A working standard sample was obtained based on the butein substance, the authenticity and purity of which was confirmed by melting point, as well as using HPLC, mass spectroscopy, UV and IR spectroscopy. The resulting standard working sample was further used to develop a method for the quantitative determination of butein in Cosmos bipinnate flowers using solid-phase extraction. The butein content in terms of dry raw materials is 0,043%3%.

Keywords: 
butein
chalcone
working standard sample
Cosmos bipinnatus Cav.
HPLC
solid-phase extraction
synthesis.

References: 
  1. Wang R., Wu Q.X., Shi Y.P. Flavonoids and polyacetylenes from the aerial parts of Bidens tripartite. Biochem. Syst. Ecol. 2013; 48: 42–44.
  2. Prachayasittikul S. Buraparuangsang P., Worachartcheewan A. et al. Antimicrobial and Antioxidative Activities of Bioactive Constit-uents from Hydnophytum formicarum Jack. Molecules. 2008; 13 (4): 904–921.
  3. Sener I. Tekelioğlu F., Zurnaci M., et al. Chemical Composition, Antibacterial and Antioxidant Activities of Thymus praecox. Kastamonu University Journal of Forestry Faculty. 2021; 21(1): 65–73.
  4. Аджиахметова С.Л., Поздняков Д.И., Червонная Н.М. и др. Фенольные соединения и пектиновые вещества листьев крыжовника отклоненного Grossularia reclinata (L) MILL. Фармация и фармакология. 2018; 6 (2): 121–134 (Adzhiah-metova S.L., Pozdnjakov D.I., Chervonnaja N.M. i dr. Fe-nol'nye soedinenija i pektinovye veshhestva list'ev kryzhovnika otklonen-nogo Grossularia reclinata (L) MILL. Farmacija i farmakologija. 2018; 6 (2): 121–134).
  5. Rukovitsina V.M., Oganesyan E.T., Pozdnyakov D.I. Synthesis and study of the effect of 3-substituted chromone derivatives on chang-es in the activity of mitochondrial complex III under experimental cerebral ischemia. Journal of Research in Pharmacy. 2022; 23 (6): 408–420.
  6. Darshani P., Gumpu M.B., Thumpati P., et al. Chemically synthe-sized butein and butin: Optical, structure and electrochemical redox functionality at electrode interface. Journal of Photochemistry and Photobiology B: Biology. 2018; 182: 122–129.
  7. Государственная фармакопея Российской Федерации. [Элек-тронный ресурс]. 14-е изд. Режим доступа: http://femb.ru/fe-mb/pharmacopea.php. Дата обращения: 26.10.2023 (Gosudar-stvennaja farmakopeja Rossijskoj Federacii. [Jelektronnyj resurs]. 14-e izd. Rezhim dostupa: http://femb.ru/femb/phar-macopea.php. Data obrashhenija: 26.10.2023).