Abstract
The costmary (Tanacetum vulgare L., syn.: Chrysanthemum vulgare (L). Bernh) is a perennial medicinal plant with a Euro-Asian type of a habitat. The costmary extracts have a wide spectrum of a biological and pharmacological activity. A drug with high choleretic and anti-inflammatory activity was created on the basis of the butanol fraction of the extract from the T. vulgare flowers in the All-Russian Institute of Medicinal and Aromatic Plants. The goal of this investigation was a determination of the qualitative composition and the quantitative content of phenolic compounds of the butanol fraction which are considered to be probably responsible for the biological activity of the extract. High performance liquid chromatography with diode-array detection in a combination with high-resolution mass spectrometry (UPLC-PDA-HRMS) was used for the analysis. We demonstrated that seven phenolic compounds were present in the butanol fraction of T. vulgare, including the first-isolated myricetin-3-glucoside. The content of the phenolic compounds achieved 90%, and neochlorogenic, 3,5-, and 4,5-dicaffeoylquinic acids were the main compounds (their content was 69%). Thus, the high content of caffeoylquinic acids could be responsible for the pharmacological activity of the drug based on the butanol fraction of the extract from the costmary flowers.
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REFERENCES
Gosudarstvennaya farmakopeya Rossiiskoi Federatsii (State Pharmacopoeia of the Russian Federation), 14th ed., Moscow, 2018. https://pharmacopoeia.ru/gosudarstvennaya-farmakopeya-14-izdaniya.
Mot, C.A., Lupitu, A.I., Bangau, S., Ovan, C.I., Copolovici, D.M., Purza, L., Melinte, C.E., and Copolovici, L., Composition and antioxidant activity of aqueous extracts obtained from herb of tansy (Tanacetum vulgare L.), Rev. Chim., 2018, vol. 69, no. 5, pp. 1041–1044. https://doi.org/10.37358/RC.18.5.6257
Onozato, T., Nakamura, C.V., Cortez, D.A., Dias Filho, B.P., and Ueda-Nakamura, T., Tanacetum vulgare: Antiherpes virus activity of crude extract and the purified compound parthenolide, Phytother. Res., 2009, vol. 23, no. 6, pp. 791–796. https://doi.org/10.1002/ptr.2638
Alvarez, A.L., Habtemariam, S., Juan-Badaturuge, M., Jackson, C., and Parra, F., In vitro anti HSV-1 and HSV-2 activity of Tanacetum vulgare extracts and isolated compounds: An approach to their mechanisms of action, Phytother. Res., 2011, vol. 25, no. 2, pp. 296–301. https://doi.org/10.1002/ptr.3382
Goun, E.A., Petrichenko, V.M., Solodnikov, S.U., Suhinina, T.V., Kline, M.A., Cunningham, G., Nguyen, C., and Miles, H., Anticancer and antithrombin activity of Russian plants, J. Ethnopharmacol., 2002, vol. 81, no. 3, pp. 337–342. https://doi.org/10.1016/s0378-8741(02)00116-2
Ivănescu, B., Tuchiluş, C., Corciovă, A., Lungu, C., Mihai, C.T., Gheldiu, A.M., and Vlase, L., Antioxidant, antimicrobial and cytotoxic activity of Tanacetum vulgare, Tanacetum corymbosum and Tanacetum macrophyllum extracts, Farmacia, 2018, vol. 66, no. 2, pp. 282–288.
Vasileva, A., Iliev, I.A., Lozanov, V., Dimitrova, M., Mitev, V., and Ivanov, I., In vitro study on the antitumor activity of Tanacetum vulgare L. extracts, Bulg. Chem. Commun., 2019, vol. 51, no. 2, pp. 249–255. https://doi.org/10.34049/bcc.51.2.5035
Mureşan, M.L., Antimicrobial effects of the ethanolic extracts and essential oils of Tanacetum vulgare L. from Romania, Acta Univ. Cibin., Ser. E: Food Technol., 2015, vol. 19, no. 2, pp. 75–80. https://doi.org/10.1515/aucft-2015-0016
Zolotaikina, M.Y., Hontova, T.M., Kotov, A.H., Ilyina, T.V., and Kryvoruchko, O.V., Study of dry extract of tansy (Tanacetum vulgare) using the method of high-performance liquid chromatography, Pharma Chem., 2017, vol. 9, no. 11, pp. 1–4.
Kalko, K.O., Mishchenko, O.Y., Derymedvid, L.V., Zolotaikina, M.Y., Gontova, T.M., Mashtaler, V.V., and Kutsenko, S.A., A screening study of hepatoprotective activity of liquid extract from common tansy Tanacetum vulgare L. herb in the setting of subchronic hepatitis in rats, Res. J. Pharm. Technol., 2018, vol. 11, no. 10, pp. 4393–4396. https://doi.org/10.5958/0974-360X.2018.00803.X
Kameri, A., Kocani, F., Hashani, Z., Kurteshi, K., Kamberi, B., Kurti, A., and Haziri, A., Antifungal and synergistic effects of the ethyl acetate extract of Tanacetum vulgare (L.) against Candida albicans, Med. Sci. Monitor Basic Res., 2019, vol. 27, pp. 179–186. https://doi.org/10.12659/MSMBR.917394
Kurkina, A.V., Study of the flavonoid composition of tansy (Tanacetum vulgare L.) flowers, Khim. Rastit. Syr’ya, 2011, no. 4, pp. 209–212.
Kurkina, A.V., Kalabukhova, E.A., Vlasova, G.I., Demidova, G.A., and Avdeeva, E.V., The new approaches to the standardization of tansy flowers (Tanacetum vulgare L.), Sovrem. Probl. Nauki Obrazov., 2013, no. 5, pp. 628–628.
Uehara, A., Akiyama, S., and Iwashina, T., Foliar flavonoids from Tanacetum vulgare var. boreale and their geographical variation, Nat. Product Commun., 2015, vol. 10, pp. 403–405. https://doi.org/10.1177/1934578X1501000307
Glyzin, V.I., Smirnova, L.P., and Ob’edkova, E.F., The method of obtaining funds with choleretic activity, RF Inventor’s Certificate, 1994, no. 1361760.
Guijas, C., Montenegro-Burke, J.R., Domingo-Almenara, X., Palermo, A., and Warth, B., MTELIN: A technology platform for identifying knowns and unknowns, Anal. Chem., 2018, vol. 90, pp. 3156–3164. https://doi.org/10.1021/acs.analchem.7b04424
Wishart, D.S., Feunang, Y.D., and Marcu, A., HMDB 4.0: The human metabolome database for 2018, Nucl. Acids Res., 2018, vol. 46, no. D1, pp. 608–617. .https://doi.org/10.1093/nar/gkx1089
Devrnja, N., Andjelković, B., Arandjelović, S., Radulović, S., Soković, M., Krstić-Milošević, M., Mihailo, R., and ćalić, D., Comparative studies on the antimicrobial and cytotoxic activities of Tanacetum vulgare L. essential oil and methanol extracts, South Afric. J. Botany, 2017, vol. 111, pp. 212–221. https://doi.org/10.1016/j.sajb.2017.03.028
Yur, S., Tekin, M., Göger, F., Başer, K.H.C., Özek, T., and Özek, G., Composition and potential of Tanacetum haussknechtii bornm. Grierson as antioxidant and inhibitor of acetylcholinesterase, tyrosinase, and α-amylase enzymes, Int. J. Food Propert., 2017, vol. 20, pp. 2359–2378. https://doi.org/10.1080/10942912.2017.1370600
Wu, C., Chen, F., Wang, X., Wu, Y., Dong, M., He, G., Galyean, R.D., He, L., and Huang, G., Identification of antioxidant phenolic compounds in feverfew (Tanacetum parthenium) by HPLC ESI MS/MS and NMR, Phytochem. Anal., 2007, vol. 18, pp. 401–410. https://doi.org/10.1002/pca.995
Venditti, A., Frezza, C., Sciubba, F., Serafini, M., Bianco, A., Cianfaglione, K., Lupidi, G., Quassinti, L., Bramucci, M., and Maggi, F., Volatile components, polar constituents and biological activity of tansy daisy (Tanacetum macrophyllum (Waldst. et Kit.) Schultz Bip.), Ind. Crops Products, 2018, vol. 118, pp. 225–235. https://doi.org/10.1016/j.indcrop.2018.03.056
Gevrenova, R., Zheleva-Dimitrova, D., Balabanova, V., Voynikov, Y., Sinan, K.I., Mahomoodally, M.F., and Zengin, G., Integrated phytochemistry, bio-functional potential and multivariate analysis of Tanacetum macrophyllum (Waldst. & Kit.) Sch.bip. and Telekia speciosa (Schreb.) Baumg. (Asteraceae), Ind. Crops Products, 2020, vol. 155, p. 112817. https://doi.org/10.1016/j.indcrop.2020.112817
Nam, K.W., Kim, J., Hong, J.J., Choi, J.H., Mar, W., Cho, M.H., Kim, Y.M., Oh, S.R., Lee, H.K., Nam, K.H., and Oh, G.T., Inhibition of cytokine-induced IkB kinase activation as a mechanism contributing to the anti-atherogenic activity of tilianin in hyperlipidemic mice, Atherosclerosis, 2005, vol. 180, pp. 27–35. https://doi.org/10.1016/j.atherosclerosis.2004.11.022
Akanda, M.R., Uddin, M.N., Kim, I.-S., Ahn, D., Tae, H.-J., and Park, B.-Y., The biological and pharmacological roles of polyphenol flavonoid tilianin, Eur. J. Pharmacol., 2019, vol. 842, pp. 291–297. https://doi.org/10.1016/j.ejphar.2018.10.044
Zhen, Z.G., Ren, S.H., Ji, H.M., Ji, H.M., Ma, J.H., Ding, X.M., Feng, F.Q., Chen, S.L., Zou, P., Ren, J.R., and Jia, L., Linarin suppresses glioma through inhibition of NF-kB/p65 and up-regulating p53 expression in vitro and in vivo, Biomed. Pharmacother., 2017, vol. 95, pp. 363–374. https://doi.org/10.1016/j.biopha.2017.08.023
Xu, Z., Sun, X., Lan, Y., Han, C., Zhang, Y., and Chen, G., Linarin sensitizes tumor necrosis factor-related apoptosis (TRAIL)-induced ligand-triggered apoptosis in human glioma cells and in xenograft nude mice, Biomed. Pharmacother., 2017, vol. 95, pp. 1607–1618. https://doi.org/10.1016/j.biopha.2017.08.021
Yonekawa, M., Shimizu, M., Kaneko, A., Matsumura, J., and Takahashi, H., Suppression of R5-type of HIV-1 in CD4+NKT cells by Vδ1+T cells activated by flavonoid glycosides, hesperidin and linarin, Sci. Rep., 2019, vol. 9, p. 7506. https://doi.org/10.1038/s41598-019-40587-6
Kim, B., Lee, J.H., Seo, M.J., Eom, S.H., and Kim, W., Linarin down-regulates phagocytosis, pro-inflammatory cytokine production, and activation marker expression in RAW264.7 macrophages, Food Sci. Biotechnol., 2016, vol. 25, pp. 1437–1442. https://doi.org/10.1007/s10068-016-0223-3
Motaal, A.A., Ezzat, S.M., Tadros, M.G., and El-Askary, H.I., In vivo anti-inflammatory activity of caffeoylquinic acid derivatives from solidago virgaurea in rats, Pharm. Biol., 2016, vol. 54, pp. 2864–2870. https://doi.org/10.1080/13880209.2016.1190381
Cho, J.-Y., Kim, J.Y., Lee, Y.G., Lee, H.J., Shim, H.J., Lee, J.H., Kim, S.-J., Ham, K.-S., and Moon, J.-H., Four new dicaffeoylquinic acid derivatives from glasswort (Salicornia herbacea L.) and their antioxidative activity, Molecules, 2016, vol. 21, p. 1097. https://doi.org/10.3390/molecules21081097
Mijangos-Ramos, I.F., Zapata-Estrella, H.E., Ruiz-Vargas, J.A., Escalante-Erosa, F., Gómez-Ojeda, N., García-Sosa, K., Cechinel-Filho, V., Meira-Quintão, N.L., and Peña-Rodríguez, L.M., Bioactive dicaffeoylquinic acid derivatives from the root extract of Calea urticifolia, Rev. Brasil. Farmacognos., 2018, vol. 28, pp. 339–343. .https://doi.org/10.1016/j.bjp.2018.01.010
McDougall, B., King, P.J., Wu, B.W., Hostomsky, Z., Reinecke, M.G., and Robinson, W.E., Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase, Antimicrob. Agents Chemother., 1998, vol. 42, pp. 140–146. https://doi.org/10.1128/AAC.42.1.140
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CONCLUSIONS
The composition and content of the phenolic compounds in the butanol fraction of the costmary flowers (Tanаcetum vulgare L.) which exhibited high cholagogue and anti-inflammatory activity were studied by the UPLC-PDA-HRMS method. The seven phenolic compounds were identified, including the first-discovered myricetin-3-glucoside. The content of the phenolic compounds in the butanol fraction was shown to achieve 90%. Neochlorogenic and 3,5-dicaffeoylquinic acids were found to be the main compounds (their content was as high as 69%). These results evidenced that the high content of caffeoylquinic acids could be responsible for the pharmacological activity of the medicine on the basis of the butanol fraction of the extract from the costmary flowers.
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Krol, T.A., Zinnatshina, L.V., Baleev, D.N. et al. An Identification and a Quantitative Assessment of Phenolic Compounds in a Butanol Fraction of Extract from Cosmary Flowers (Tanacetum vulgare). Russ J Bioorg Chem 48, 1454–1460 (2022). https://doi.org/10.1134/S1068162022070135
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DOI: https://doi.org/10.1134/S1068162022070135