Eutectic solvents for the extraction of phenolic compounds from the Moldovan Dragonhead

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Abstract

Introduction. Deep eutectic solvents (DES) are of interest to modern pharmaceutical technology as alternative extractants to traditional organic solvents. The prospects for their use are due to low toxicity, biodegradability, the possibility of selective extraction of individual substances and regeneration of the extractant.

The purpose of the study is to develop and optimize a technology for ultrasonic extraction of phenolic acids from the Moldovan dragonhead using DES, and to study the antioxidant activity of the resulting extracts.

Results. 11 DES compositions with different molar ratios of components were obtained; the optimal composition one was selected based on choline and lactic acid in a molar ratio of 1:3. The dependence of the extraction of phenolic compounds on the composition of DES, the influence of water content in the composition of DES on the process of extraction of phenolic compounds have been studied. Data were obtained on the antioxidant activity of the Moldavian snakehead extract obtained using DES.

Conclusion. A method has been developed for the extraction of phenolic acids from the Moldavian snakehead with deep eutectic solvents. The extraction efficiency of the DES-3 mixture based on choline chloride and lactic acid in a molar ratio of 1:3 has been proven. The content of phenolic compounds in terms of rosmarinic acid was 7.72±0.12%, which is 0.23% more than when using 50% ethyl alcohol as an extractant. Using cyclic voltammetry, it was established that the antioxidant activity of extracts obtained using DES is due to the content of rosmarinic acid.

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About the authors

Marina Arkadyevna Dzhavakhyan

Russian University of Medicine; All-Russian Research Institute of Medicinal and Aromatic Plants

Email: akopovamarina13@mail.ru
ORCID iD: 0000-0003-2673-6203

Doctor of Pharmaceutical Sciences, Associate Professor, Deputy Director of the Scientific and Educational Institute for the Development and Introduction of Medicines; Chief Researcher of the Experimental and Technological Department

Russian Federation, Moscow; Moscow

Olesya Konstantinovna Pavelyeva

Russian University of Medicine

Email: pavelieva.olesya@yandex.ru
ORCID iD: 0000-0002-2397-8920

Applicant

Russian Federation, Moscow

Vyacheslav Nikolaevich Dul

Russian University of Medicine; All-Russian Research Institute of Medicinal and Aromatic Plants

Email: dvnslava@yandex.ru
ORCID iD: 0000-0001-7824-4417

Candidate of Pharmaceutical Sciences, Researcher of the Development and Implementation of Innovative Medicines Research Laboratory; Researcher

Russian Federation, Moscow; Moscow

Anna Gurgenovna Kuregyan

Pyatigorsk Medical and Pharmaceutical Institute – a branch of the Volgograd Medical State University

Email: Kooreguan@mail.ru
ORCID iD: 0000-0002-0698-8254

Doctor of Pharmaceutical Sciences, Professor of the Pharmaceutical Chemistry Department

Russian Federation, Pyatigorsk

Tatiana Yurievna Tatarenko-Kozmina

Russian University of Medicine

Email: kosmtina025@gmail.com
ORCID iD: 0009-0000-8569-9209

Doctor of Biological Sciences, Professor, Head of the Medical Biology and Fundamentals of Cellular and Molecular Biotechnology Department

Russian Federation, Moscow

Anatoly Petrovich Pleten

Russian University of Medicine

Author for correspondence.
Email: pleatol@mail.ru
ORCID iD: 0000-0003-4991-2150

Doctor of Biological Sciences, Professor of the Biological Chemistry Department

Russian Federation, Moscow

References

  1. Storz G., Imlay J.A. Oxidative stress. Curr. Opin. Microbiol. 1999; 2 (2): 188–94. doi: 10.1016/s1369-5274(99)80033-2.
  2. Christofidou-Solomidou M., Muzykantov V.R. Antioxidant Strategies in Respiratory Medicine. Treat. Respir. Med. 2006; 5: 47–78. doi: 10.2165/00151829-200605010-00004.
  3. Nathens A.B., Neff M.J., Jurkovich G.J. et al Randomized, Prospective Trial of Antioxidant Supplementation in Critically Ill Surgical Patients. Annals of Surgery. 2002; 236 (6): 814–22. doi: 10.1097/00000658-200212000-00014.
  4. Государственная фармакопея РФ IV издания. М., 2018. [Электронный ресурс]. Доступно на: https://docs.rucml.ru/feml/pharma/v14/vol1/ [дата обращения: 04.12.2023]. [The State Pharmacopoeia of the Russian Federation IV edition. Moscow, 2018. [Electronic resource]. Available on: https://docs.rucml.ru/feml/pharma/v14/vol1 / [date of access: 04.12.2023] (in Russian)]
  5. Ha A.C., Nguyen Ch.D.P., Le T.M. Screening medicinal plant extracts for xanthine oxidase inhibitory activity/ Fine Chemical Technologies. 2022; 17 (2): 131–9.
  6. Расулова Ф.Ф., Сарибоева Н.Н., Исаков Т.Т., Жалолов К.Б. Розмарин лекарственный (Rosmarinun officinalis L.) и его полезные свойства. Life Sciences and Agriculture. 2020; 2 (2): 109–11. [Rasulova F.F., Sariboeva N.N., Isakov T.T., ZHalolov K.B. Medicinal rosemary (Rosmarinun officinalis L.) and its beneficial properties. Life Sciences and Agriculture. 2020; 2 (2): 109–11 (in Russian)]
  7. Казарян Ш.А., Рштуни Л.Р., Геворкян М.Л., Оганян А.Ж., Вардапетян Г.Р. Антирадикальные свойства этанольных экстрактов листьев Prunella vulgaris L. и Ocimum basilicum L. Вестник Российско-Армянского (Славянского) университета: физико-математические и естественные науки. 2016; 2: 86–93. [Kazaryan SH.A., Rshtuni L.R., Gevorkyan M.L., Oganyan A.ZH., Vardapetyan G.R. Antiradical properties of ethanol extracts of Prunella vulgaris L. and Ocimum basilicum L. Vestnik Rossijsko-Armyanskogo (Slavyanskogo) universiteta: fiziko-matematicheskie i estestvennye nauki. 2016; 2: 86–93 (in Russian)]
  8. Dastmalchi K., Dorman D., Koşar M., Hiltunen R. Chemical composition and in vitro antioxidant evaluation of a water-soluble Moldavian balm (Dracocephalum moldavica L.) extract. LWT. Food Science and Technology. 2007; 40: 239–48. doi: 10.1016/j.lwt.2005.09.019.
  9. Nurhan T.D., Sibel I., Ramakanth J. Effect of the Solvent Type and Temperature on Phytosterol Contents and Compositions of Wheat Straw, Bran, and Germ Extracts. J. Agric. Food Chem. 2009; 57 (22): 10608–11. doi: 10.1021/jf9022383.
  10. Dastmalchi K., Dorman D., Laakso I., Hiltunen R. Chemical composition and antioxidative activity of Moldavian balm (Dracocephalum moldavica L.) extracts. LWT. Food Science and Technology. 2007; 40: 1655–63. doi: 10.1016/j.lwt.2006.11.013
  11. Paiva A., Craveiro R., Arosoet I. et al. Natural Deep Eutectic Solvents – Solvents for the 21st Century. ACS Sustainable Chemistry & Engineering. 2014; 2 (5): 1063–71.
  12. Smith E.L., Abbott A.P., Ryder K.S. Deep Eutectic Solvents (DESs) and Their Applications. Chemical Reviews. 2014; 114 (21): 11060–82.
  13. Abbott A.P., Boothby D., Capper G., et al. Deep Eutectic Solvents Formed between Choline Chloride and Carboxylic Acids: Versatile Alternatives to Ionic Liquids. J. of the American Chemical Society. 2004; 126 (29): 9142–7.
  14. Ilgen F., Ott D., Kralisch D., et al. Conversion of carbohydrates into 5-hydroxymethylfurfural in highly concentrated low melting mixtures. Green Chemistry. 2009; 11 (12): 1948–54.
  15. Прожогина Ю.Е., Джавахян М.А. Сборник международной научной конференции «От биохимии растений к биохимии человека», 16–17 июня 2022 года. 2022; 289–95. [Prozhogina Y.E., Dzhavakhyan M.A. Natural deep eutectic solvents as alternative flavonoid extractants from the sedative plant composition, June 16-17, 2022. 2022; 289–95 (in Russian)]
  16. Джавахян М. А. Прожогина Ю.Э. Глубокие эвтектические растворители на основе холина хлорида как перспективные экстрагенты флавоноидов из седативной растительной композиции. Разработка и регистрация лекарственных средств. 2022; 11 (4): 79–86. [Dzhavahyan M. A. Prozhogina YU.E. Deep eutectic solvents based on choline chloride as promising extractants of flavonoids from sedative plant composition. Razrabotka i registraciya lekarstvennyh sredstv. 2022; 11 (4): 79–86 (in Russian)]
  17. Патент № 2782459 C1 РФ. Способ экстракции флавоноидов из растительного сырья: № 2021126053: заявл. 03.09.2021: опубл. 27.10.2022. М.А. Джавахян, А.Ю. Татаринцева, В.Н. Дул [и др.]; заявитель ФГБНУ ВИЛАР. [Patent No. 2782459 C1 of the Russian Federation. Method of extraction of flavonoids from vegetable raw materials: No. 2021126053: application 03.09.2021: publ. 27.10.2022. M.A. Dzhavahyan, A.Yu. Tatarintseva, V. N. Dul [et al.]; the applicant of the Federal State Budgetary Educational Institution VILAR (in Russian)]
  18. Патент № 2794516 C1 РФ. Способ экстракции полифенольных соединений из змееголовника молдавского: № 2021137494: заявл. 17.12.2021: опубл. 19.04.2023. М.А. Джавахян, О.К. Павельева, А.Е. Бурова [и др.]; заявитель ФГБНУ ВИЛАР. [Patent No. 2794516 C1 of the Russian Federation. Method of extraction of polyphenolic compounds from Moldovan snakehead: No. 2021137494: application 17.12.2021: publ. 04/19/2023. M.A. Dzhavahyan, O.K. Pavel'eva, A.E. Burova [et al.]; the applicant is FGBNU VILAR (in Russian)]
  19. Джавахян М.А., Прожогина Ю.Э., Павельева О.К., Каленикова Е.И. Природные глубокие эвтектические растворители как альтернативные экстрагенты флавоноидов из растительного сбора седативного действия. Разработка и регистрация лекарственных средств. 2022; 11 (3): 75–83. [Dzhavahyan M.A., Prozhogina YU.E., Pavel'eva O.K., Kalenikova E.I. Natural deep eutectic solvents as alternative extractants of flavonoids from sedative plant collection. Razrabotka i registraciya lekarstvennyh sredstv. 2022; 11 (3): 75–83 (in Russian)]
  20. Park H.E., Tang B., Row K.H. Application of Deep Eutectic Solvents as Additives in Ultrasonic Extraction of Two Phenolic Acids from Herba Artemisiae Scopariae. Analytical Letters. 2014; 47 (9): 1476–84.
  21. Xiong, Z., Wang M., Guo H., et al. Ultrasound-assisted deep eutectic solvent as green and efficient media for the extraction of flavonoids from Radix scutellariae. New Journal of Chemistry. 2019; 43 (2): 644–50.
  22. Qi X.-L., Peng X., Huang Y.-Y. et al. Green and efficient extraction of bioactive flavonoids from Equisetum palustre L. by deep eutectic solvents-based negative pressure cavitation method combined with macroporous resin enrichment. Industrial Crops and Products. 2015; 70: 142–8.
  23. Tang B., Li S., Zhang H., Row K.H. Deep Eutectic Solvent-Based HS-SME Coupled with GC for the Analysis of Bioactive Terpenoids in Chamaecyparis obtusa Leaves. Chromatographia. 2013; 4: 373–7.

Supplementary files

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2. Fig. 1. Content of phenolic compounds depending on the solvent used

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3. Fig. 2. Influence of water content in DES on the extraction process of phenolic compounds

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4. Fig. 3. Cyclic voltammogram of the herb extract of the Moldovan dragonhead based on DES-3

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5. Fig. 4. Cyclic voltammogram of the alcoholic extract of the herb Moldovan snakeheadо

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