FLAVONOID COMPOUNDS FROM ARTEMISIA GLABELLA KAR. ET. KIR., SYNTHESIS ON THEIR BASIS AND BIOLOGICAL ACTIVITY
Abstract
As a result of complex chemical processing of medicinal raw materials of Artemisia glabella Kar. et Kir., including CO2 extraction and lactones isolation, we have investigated the chemical composition of flavonoids to select the biologically active ones and carry out modifications on their basis. Two flavonoids pectolinaringenin and cirsilineol have been isolated by partition chromatography from the secondary raw materials of Artemisia glabella Kar. et. Kir. and identified. To obtain new biologically active compounds, we have synthesized new amino derivatives of cirsilineol by the Mannich reaction with secondary amines (piperidine and N-methylpiperazine) in isopropanol with the presence of dimethylaminopyridine. In proton NMR spectrum of the synthesized compounds there are proton signals of the initial cirsilineol fragment; however, there is no N-8 proton signal, besides other signals typical for amines’ benzene ring have been observed at 1.53–3.90 ppm. It means that reaction occurred at the C-8 position of carbon in ring A. The synthesized compounds have been studied for various types of biological activity typical for this class, including hepatoprotective and anti-inflammatory activities. Amino derivatives of cirsilineol exhibit a moderate activity against HepG2 cell line, while cirsilineol at a dose of 5 mg/ml expresses a pronounced hepatoprotective activity. Moreover, all samples at a dose of 25 mg/kg show poor anti-inflammatory effects on the model of acute exudative reaction in vivo.
Downloads
Metrics
References
Pribytkova L.N., Adekenov S.M. Flavonoidy rasteniy roda Artemisia. [Flavonoids of plants of the genus Artemisia]. Almaty, 1999, 180 p. (in Russ.).
Patent 015557 (EP). 2011.
Korul'kin D.YU., Abilov ZH.A., Muzychkina R.A., Tolstikov G.A. Prirodnyye flavonoid. [Natural flavonoids]. Novo-sibirsk, 2007, 232 p. (in Russ.).
Chirumbolo S. Inflamm Allergy Drug Targets, 2010, vol. 9, no. 4, pp. 263–285.
Oshitari T., Okuyama Y., Miyata Y., Kosano H., Takahashi H., Natsugari H. Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 4540–4544. DOI: 10.1016/j.bmcl.2011.05.121.
Pham T-A., Che H., Phan P-T., Lee J-W., Kim S-S., Park H. Bioorg. Med. Chem. Lett., 2012, vol. 22, pp. 2534–2535. DOI: 10.1016/j.bmcl.2012.01.135.
Farkas O., Jakus J., Heberger K. Molecules, 2004, vol. 9, pp. 1079–1088.
Shahat А.А., Cos P., Hermans N., Apers S., Bruyne T.D., Pieters L., Berghe D.V., Vlitenck A.J. Planta Medica, 2003, vol. 69, pp. 1153–1156.
Zenkov N.K., Kandalintseva N.V., Lankin V.Z., Men'shchikova Ye.B., Prosenko A.Ye. Fenol'nyye bioantioksidant. [Phenolic bioantioxidants]. Novosibirsk, 2003. С. 31–163. (in Russ.).
Baysarov G.M., Zhumatayeva A.R., Mukusheva G.K., Adekenov S.M. Novyye dostizheniya v khimii i khimicheskoy tekhnologii rastitel'nogo syr'ya: Matererialy VII Vserossiyskoy konferentsii. [New achievements in chemistry and chem-ical technology of plant raw materials: Materiel of the VII All-Russian Conference]. Barnaul, 2017, pp. 264–266. (in Russ.).
Tashenov E.O., Dzhalmakhanbetova R.I., Smagulova F.M., Dudkin R.V., Gorovoi P.G., Suleiman E.M., Ross S.A. Chem. Nat. Compd., 2013, vol. 49, no. 1, pp. 97–98. DOI: 10.1007/s10600-013-0517-0
Hajdú Z., Hohmann J., Forgo P., Máthé I., Molnár J., Zupkó I. Planta Med., 2014, vol. 80, no. 18, pp. 1692–1697. DOI: 10.1055/s-0034-1383146
Hajdú Z., Martins A., Orbán-Gyapai1 O., Forgo P., Jedlinszki N., Máthé I., Hohmann J. Rec. Nat. Prod., 2014, vol. 8, no. 3, pp. 299–302.
Costa R., Ragusa S., Russo M., Certo G., Franchina F.A., Zanotto A., Grasso E., Mondello L., Germanò M.P. Journal of Pharmaceutical and Biomedical Analysis, 2016, vol. 117, pp. 499–509. DOI: 10.1016/j.jpba.2015.10.006.
Belenovskaya L.M., Markova L.P. Rastitel'nyye resursy, 1992, issue 1, pp. 122–124. (in Russ.).
Chemesova I.I., Belenovskaya L.M., Markova L.P. Khimiya prirodnykh soyedineniy, 1984, no. 6, pp. 789–790. (in Russ.).
Belenovskaya L.M., Markova L.P., Kapranova G.I. Khimiya prirodnykh soyedineniy, 1980, no. 6, pp. 834–835. (in Russ.).
Benayache F., Boureghda A., Ameddah S., Marchioni E., Benayache F., Benayache S. Der Pharmacia Lettre, 2014, vol. 6, no. 2, pp. 50–54.
Mohamed Ali A., Wong Keng Chong. Records of Natural Products, 2015, vol. 9, no. 1, pp. 159–163.
Yan-Ming Wang A., Jian-Qiang Zhao B., Jun-Li Yang A., Yan-Duo Tao B., Li-Juan Mei B., Yan-Ping Shi. Natural Product Research, 2017, vol. 31, no. 12, pp. 1365–1369. DOI: 10.1080/14786419.2016.1247083.
Roman G. Eur. J. Med. Chem., 2015, vol. 89, pp. 743–816. DOI: 10.1016/j.ejmech.2014.10.076.
Zhang S., Ma J., Bao Y., Yang P., Zou L., Li K., Sun X. Bioorg. Med. Chem., 2008, vol. 16, no. 15, pp. 7127–7132. DOI: 10.1016/j.bmc.2008.06.055.
Helgen T.R., Sciotti R.J., Lee P., Duffy S., Avery V.M., Igbinoba O., Akoto M., Hagen T.J. Bioorg. Med. Chem. Lett., 2015, vol. 25, no. 2, pp. 327–332. DOI: 10.1016/j.bmcl.2014.11.039.
This work is licensed under a Creative Commons Attribution 4.0 International License.
The authors, which are published in this journal, agree to the following conditions:
1. Authors retain the copyright to the work and transfer to the journal the right of the first publication along with the work, at the same time licensing it under the terms of the Creative Commons Attribution License, which allows others to distribute this work with the obligatory indication of the authorship of this work and a link to the original publication in this journal .
2. The authors retain the right to enter into separate, additional contractual agreements for the non-exclusive distribution of the version of the work published by this journal (for example, to place it in the university depository or to publish it in a book), with reference to the original publication in this journal.
3. Authors are allowed to post their work on the Internet (for example, in a university repository or on their personal website) before and during the review process of this journal, as this may lead to a productive discussion, as well as more links to this published work.
