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Effect of an Extractant on the Composition of the Lipophilic Constituents of the Extracts of Rhodiola rosea L. and on the Extracts’ Activity

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Abstract

The composition of the lipophilic components of the Rhodiola rosea L. plant was studied. Acidic and neutral components were identified by gas chromatography–mass spectrometry. With methyl-tert-butyl ether (MTBE) as an extractant instead of the volatile solvent diethyl ether, lipophilic extract was obtained. Methyl-tert-butyl ether used as an extraction solvent for raw materials has all the advantages of diethyl ether, being free of its disadvantages. It does not form peroxides or produce elevated partial gas pressure due to its higher boiling point. As a result, comparison with databases identified some triterpene, phenolic, and aliphatic acids with chain lengths 12 to 30 carbon atoms, including saturated, unsaturated, and dibasic acids. In addition to the components known from the literature, more than 50 triterpene and aliphatic compounds were detected in the unsaponifiable residue and acidic fractions for the first time. The hexane extract and the product obtained by the stepwise extraction by MTBE after the extraction of low-polarity compounds with hexane were investigated in a similar way. In the case of an extract obtained using MTBE after the extraction of low-polarity components with hexane, extraction of benzoic and cinnamic acids was more efficient compared to the exhaustive extraction of MTBE. These acids are absent from the hexane extract. Ethanol extraction was also carried out to test bioactivity: exhaustive and after hexane and MTBE extraction. Extracts obtained using MTBE and ethanol showed antiviral activity against the Ebola pseudovirus.

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REFERENCES

  1. Budantsev, A.L. and Lesiovskaya, E.E., Dikorastushchie poleznye rasteniya Rossii (Wild Useful Plants of Russia), St. Petersburg, 2001.

    Google Scholar 

  2. Brown, R.P., Gerbarg, P.L., and Ramazanov, Z., Rhodiola rosea: A phytomedicinal overview, Herbal Gram., 2002, vol. 56, pp. 40–52.

    Google Scholar 

  3. Wang, H., Ding, Y., Zhou, J., Sun, X., and Wang, S., The in vitro and in vivo antiviral effects of salidroside from Rhodiola rosea L. against coxsackievirus B3, Phytomedicine, 2009, vol. 16, pp. 146–155. https://doi.org/10.1016/j.phymed.2008.07.013

    Article  CAS  Google Scholar 

  4. Kwon, Y.-I., Jang, H.-D., and Shetty, K., Evaluation of Rhodiola crenulata and Rhodiola rosea for management of type ii diabetes and hypertension, Asia Pacif. J. Clin. Nutr., 2006, vol. 15, pp. 425–432.

    Google Scholar 

  5. Krylov, G.V., Travy zhizni i ikh iskateli (Herbs of Life and their Seekers), Novosibirsk, 1969.

  6. Bykov, V.A., Zapesochnaya, G.G., and Kurkin, V.A., Traditional and biotechnological aspects of obtaining medicinal preparations from Rhodiola rosea L. (a review), Pharm. Chem. J., 1999, vol. 33, pp. 29–40. https://doi.org/10.1007/BF02508414

    Article  CAS  Google Scholar 

  7. Rastitel’nye resursy Rossii: Dikorastushchie tsvetkovye rasteniya, ikh komponentnyi sostav i biologicheskaya aktivnost’ (Plant Resources of Russia: Wild Flowering Plants, their Composition and Biological Activity), Budantsev, A.L., Ed., St. Petersburg: Tov-vo Nauch. Izdan. KMK, 2009, vol. 2.

    Google Scholar 

  8. Saratikov, A.S., Zolotoi koren’ (Rodiola rozovaya) (Golden Root (Rhodiola rosea)), Tomsk, 1974.

  9. Krasnov, E.A., Chemical study and the possibility of using in medicine a number of plants of the Crassulaceae family of the flora of the USSR, Extended Abstract of Doctoral (Pharm. Sci.) Dissertation, Moscow, 1990.

  10. Krasnov, E.A., Saratikov, A.S., and Surov, Yu.P., Rasteniya semeistva tolstyankovykh (Plants of the Crassulaceae Family), Tomsk, 1979.

  11. Kurkin, V.A., Chemical study of Rhodiola rosea L., Extended Abstract of Cand. Sci. (Pharm. Sci.) Dissertation, Moscow, 1985.

  12. Dikorastushchie poleznye rasteniya flory Mongol’skoi Narodnoi Respubliki (Wild Useful Plants of the Flora of the Mongolian People’s Republic), Leningrad, 1985.

  13. Rohloff, J., Volatiles from rhizomes of Rhodiola rosea L., Phytochemistry, 2002, vol. 59, no. 6, pp. 655–661. https://doi.org/10.1016/s0031-9422(02)00004-3

    Article  CAS  Google Scholar 

  14. Todorova, T.M., Evstatieva, L., Platicanov, S., and Kuleva, L., Chemical composition of essential oil from bulgarian Rhodiola rosea L. rhizomes, J. Essent. Oil. Bear. Plants, 2006, vol. 9, no. 3, pp. 267–270. https://doi.org/10.1080/0972060X.2006.10643502

    Article  CAS  Google Scholar 

  15. Evstatieva, L., Todorova, M., Antonova, D., and Staneva, J., Chemical composition of the essential oils of Rhodiola rosea L. of three different origins, Pharmacogn. Mag., 2010, vol. 6, no. 24, pp. 256–258. https://doi.org/10.4103/0973-1296.71782

    Article  CAS  Google Scholar 

  16. Ma, G., Li, W., Dou, D., Chang, X., Bai, H., Satou, T., Li, J., Sun, D., Kang, T., Nikaido, T., and Koike, K., Rhodiolosides A–E, monoterpene glycosides from Rhodiola rosea, Chem. Pharm. Bull., 2006, vol. 54, no. 8, pp. 1229–1233. https://doi.org/10.1248/cpb.54.1229

    Article  CAS  Google Scholar 

  17. Bridel, M. and Beguin, C., Isolation of rutoside, asparagines and a new glycoside, hydrolysable by emulsion, salidroside from Salix triandra L., Seanc. Acad. Sci., 1926, vol. 183, pp. 321–323

    Google Scholar 

  18. Tolonen, A., Pakonen, M., Hohtola, A., and Jalonen, J., Phenylpropanoid glycosides from Rhodiola rosea, Chem. Pharm. Bull., 2003, vol. 51, no. 4, pp. 467–470. https://doi.org/10.1248/cpb.51.467

    Article  CAS  Google Scholar 

  19. Akgul, Y., Ferreira, D., Abourashed, E.A., and Khan, I.A., Lotaustralin from Rhodiola rosea roots, Fitoterapia, 2004, vol. 75, no. 6, pp. 612–614. https://doi.org/10.1016/j.fitote.2004.06.002

    Article  CAS  Google Scholar 

  20. Ali, Z., Fronszek, F.R., and Khan, I.A., Phenylalkaloides and monoterpene analogues from the roots of Rhodiola rosea, Planta Med., 2008, vol. 74, no. 2, pp. 178–181. https://doi.org/10.1055/s-2008-1034288

    Article  CAS  Google Scholar 

  21. Ming, D.S., Hillhouse, B.J., Guns, E.S., Eberding, A., **e, S., Vimalanathan, S., and Towers, G.H., Bioactive compounds from Rhodiola rosea (Crassulaceae), Phytoter. Res., 2005, vol. 19, no. 9, pp. 740–743. https://doi.org/10.1002/ptr.1597

    Article  CAS  Google Scholar 

  22. Petsalo, A., Jalonen, J., and Tolonen, A., Identification of flavonoids of Rhodiola rosea by liquid chromatography tandem mass spectrometry, J. Chromatogr., A, 2006, vol. 1112, pp. 224–231. https://doi.org/10.1016/j.chroma.2005.11.056

    Article  CAS  Google Scholar 

  23. Panossian, A., Wikman, G., and Sarris, J., Rosenroot (Rhodiola rosea): Traditional use, chemical composition, pharmacology and clinical efficacy, Phytomedicine, 2010, vol. 17, pp. 481–493. https://doi.org/10.1016/j.phymed.2010.02.002

    Article  CAS  Google Scholar 

  24. Hethelyi, E.B., Korany, K., Galambesi, B., Domokos, J., and Palinkas, J., Chemical composition of essential oil from rhizomes of Rhodiola rosea L. grown in Finland, J. Essent. Oil. Res., 2005, vol. 17, no. 6, pp. 628–629. https://doi.org/10.1080/10412905.2005.9699016

    Article  CAS  Google Scholar 

  25. Shatar, S., Adams, R.P., and Koenig, W., Comparative study of the essential oil of Rhodiola rosea L. from Mongolia, J. Essent. Oil. Res., 2007, vol. 19, no. 3, pp. 215–217. https://doi.org/10.1080/10412905.2007.9699264

    Article  CAS  Google Scholar 

  26. Marchev, A.S., Aneva, I.Y., Koycheva, I.K., and Georgiev, M.I., Phytochemical variations of Rhodiola rosea L. wild-grown in Bulgaria, Phytochem. Lett., 2017, vol. 20, pp. 386–390. https://doi.org/10.1016/j.phytol.2016.12.030

    Article  CAS  Google Scholar 

  27. Mirmazloum, I., Ladányi, M., and György, Z., Changes in the content of the glycosides, aglycons and their possible precursors of Rhodiola rosea during the vegetation period, Nat. Prod. Commun., 2015, vol. 10, pp. 1413–1416.

    Google Scholar 

  28. Alperth, F., Turek, I., Weiss, S., Vogt, D., and Bucar, F., Qualitative and quantitative LC-MS analysis of different Rhodiola rosea rhizome extracts, Sci. Pharm., 2019, vol. 87, no. 2, p. 8. https://doi.org/10.3390/scipharm87020008

    Article  CAS  Google Scholar 

  29. Ioset, K.N., Nyberg, N.T., van Diermen, D., Malnoe, P., Hostettmann, K., Shikov, A.N., and Jaroszewski, J.W., Metabolic profiling of Rhodiola rosea rhizomes by 1H NMR spectroscopy, Phytochem. Anal., 2011, vol. 22, pp. 158–165. https://doi.org/10.1002/pca.1262

    Article  CAS  Google Scholar 

  30. Ganzera, M., Yayla, Y., and Khan, I.A., Analysis of the marker compounds of Rhodiola rosea L. (golden root) by reversed phase high performance liquid chromatography, Chem. Pharm. Bull., 2001, vol. 49, no. 4, pp. 465–467. https://doi.org/10.1248/cpb.49.465

    Article  CAS  Google Scholar 

  31. Kukina, T.P., Frolova, T.S., and Salnikova, O.I., Neutral constituents of Chamaenerion angustifolium leaves, Chem. Nat. Compd., 2014, vol. 50, no. 2, pp. 233–236. https://doi.org/10.1007/s10600-014-0920-1

    Article  CAS  Google Scholar 

  32. Kukina, T.P., Shcherbakov, D.N., Gensh, K.V., Tulysheva, E.A., Salnikova, O.I., Grazhdannikov, A.E., and Kolosova, E.A., Bioactive components of sea buckthorn Hippophae rhamnoides L. foliage, Russ. J. Bioorg. Chem., 2017, vol. 43, no. 7, pp. 57–61. https://doi.org/10.1134/S1068162017070093

    Article  Google Scholar 

  33. Kukina, T.P., Shcherbakov, D.N., Gensh, K.V., Panteleeva, N.V., Tulysheva, E.A., Salnikova, O.I., Grazhdannikov, A.E., Kolosov, P.V., and Galitsyn, G.Yu., Bioactive components in methyl tert-butyl ether extract of sea buckthorn (Hippophae rhamnoides L.) green waste, Russ. J. Bioorg. Chem., 2020, vol. 46, no. 7, pp. 1372–1377. https://doi.org/10.1134/S1068162020070067

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors are grateful to the Shared Use Chemical Research Center of the Siberian Branch of the Russian Academy of Sciences for the GC–MS analysis.

Funding

The study was supported by the Russian Foundation for Basic Research (project nos. 19-34-90076 and 20-54-44016/20).

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Authors and Affiliations

  1. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, 630090, Novosibirsk, Russia

    T. P. Kukina, I. A. Elshin, O. I. Salnikova, D. A. Karakai & E. D. Mordvinova

  2. Altai State University, 656049, Barnaul, Russia

    D. N. Shcherbakov & V. O. Korsakov

  3. State Scientific Center Vector, 630559, Koltsovo, Novosibirsk oblast, Russia

    D. N. Shcherbakov, A.V. Zybkina & E. D. Mordvinova

  4. Novosibirsk State University, 630090, Novosibirsk, Russia

    I. A. Elshin

  5. LLC VacBioLab, 432071, Ulyanovsk, Russia

    P. V. Kolosov

  6. Mongolian National University of Medical Sciences, 14210, Ulaanbaatar, Mongolia

    Ts. Sandag

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  1. T. P. Kukina
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  2. D. N. Shcherbakov
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  3. A.V. Zybkina
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  4. I. A. Elshin
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  6. O. I. Salnikova
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  7. P. V. Kolosov
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  9. D. A. Karakai
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  10. E. D. Mordvinova
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Correspondence to T. P. Kukina.

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The authors declare no conflicts of interest. This article does not contain any research involving humans or animals as research objects.

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Translated by N. Onishchenko

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Kukina, T.P., Shcherbakov, D.N., Zybkina, A. et al. Effect of an Extractant on the Composition of the Lipophilic Constituents of the Extracts of Rhodiola rosea L. and on the Extracts’ Activity. Russ J Bioorg Chem 48, 1461–1469 (2022). https://doi.org/10.1134/S1068162022070147

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