HALOGENATED PHENOLIC COMPOUNDS OF NATURAL ORIGIN CONSTITUTE A RARE MINOR GROUP OF SUBSTANCES (A REVIEW)
UDC 549.4:581.192:582.32/.998
Аннотация
The composition of primary and secondary metabolites of natural origin raw materials includes major and minor compounds. Halogenated phenolic compounds are considered rare minor compounds found in natural entities. This review provides a summary of currently known halogenated phenolic compounds of natural origin.
Until the 1970s, only a few substances had been isolated and their structures determined from bacteria, fungi, and marine algae. By now, information exists on several dozen halogenated flavonoids, isoflavonoids, chromones, and depsides, isolated from bees, bacteria, fungi, algae, lichens of the genera Lecanora, Punctelia, as well as representatives of higher plants (from families Thymelaecae, Rutaceae, Apiaceae, Fabaceae, Moringaceae, and two species of the Equisetum L. genus). Only 17 substances have been isolated and identified from higher plants. The main substituents in halogenated compounds are chlorine, and less frequently bromine and fluorine.
Several studies have shown that the presence of halogens in a molecule significantly enhances biological activity. For most halogenated compounds, antibacterial, antifungal, antioxidant, and anticancer activities have been established. Some substances exhibit anxiolytic, neuroleptic, and cardioprotective properties, which is of practical interest for developing medications for the treatment and prevention of socially significant diseases.
Скачивания
Metrics
Литература
Kasanah N., Triyanto T. Biomolecules, 2019, vol. 9, 225. https://doi.org/10.3390/biom9060225.
Rezanka T., Spizek J. Studies in Natural Products Chemistry, 2003, vol. 29, pp. 309–353. https://doi.org/10.1016/S1572-5995(03)80010-8.
Wang C., Du W., Lu H. et al. Molecules, 2021, vol. 26, 2754. https://doi.org/10.3390/molecules26092754.
Motohashi K., Takagi M., Shin-Ya K. J. Nat. Prod., 2010, vol. 73, pp. 226–228. https://doi.org/10.1021/np900810r.
Jakubiec-Krzesniak K., Rajnisz-Mateusiak A., Guspiel A. et al. Pol. J. Microbiol., 2018, vol. 67, 259. https://doi.org/10.21307/pjm-2018-048.
Cheng C., Othman E.M., Reimer A. et al. Tetrahedron Lett., 2016, vol. 57, pp. 2786–2789. https://doi.org/10.1016/j.tetlet.2016.05.042.
Shaala L.A., Youssef D.T., Alzughaibi T.A. et al. Mar. Drugs., 2020, vol. 18, 450. https://doi.org/10.3390/md18090450.
Klaiklay S, Rukachaisirikul V., Tadpetch K. et al. Tetrahedron, 2012, vol. 68, pp. 2299–2305. https://doi.org/10.1016/j.tet.2012.01.041.
Anyanwutaku I.O., Zirbes E., Rosazza J.P.N. Journal of Natural Products, 1992, vol. 55(10), pp. 1498–1504. https://doi.org/10.1021/np50088a016.
Xiang W.S., Zhang J., Wang J.D. et al. J. Agric. Food Chem., 2010, vol. 58, no. 3, pp. 1933–1938. https://doi.org/10.1021/jf9035194.
Zhang J., Wang X-J, Yan Y-J. et al. J. of Agric. and Food Chemy, vol. 59, no. 13, pp. 7506-7513. https://doi.org/10.1021/jf2005194.
Marder M., Zinezuk J., Colombo M.I. et al. Bioorg. Med. Chem. Lett., 1997, vol. 7, pp. 2003–2008. https://doi.org/10.1002/chin.199749157.
Medina J.H., Viola H., Wolfman C. et al. Neurochem. Res., 1997, vol. 22, pp. 419–425. https://doi.org/10.1023/a:1027303609517.
Viola H., Marder M., Wolfman C. et al. Bioorg. Med. Chem. Lett., 1997, vol. 7, pp. 373–378. https://doi.org/10.1006/bbrc.1999.1273.
Marder M., Viola H., Wasowski C. et al. Biochem. Biophys. Res. Commun., 1996, vol. 223, pp. 384–389. https://doi.org/10.1006/bbrc.1996.0903.
Ishar M.P.S., Singh G., Singh S. et al. Bioorg. Med. Chem. Lett., 2006, vol. 16, pp. 1366–1370. https://doi.org/10.1016/j.bmcl.2005.11.044.
Valdameri G., Genoux-Bastide E., Gauthier C. et al. Chem. Med. Chem., 2012, vol. 7, pp. 1177–1180. https://doi.org/10.1002/cmdc.201200154.
Zheng X., Meng W.D., Xu Y.Y. et al. Bioorg. Med. Chem. Lett., 2003, vol. 13, pp. 881–884. https://doi.org/10.1016/s0960-894x(02)01081-8.
Beudot C., De Méo M.P., Dauzonne D. et al. Mutation Res., 1998, vol. 417, pp. 141–153. https://doi.org/10.1016/s1383-5718(98)00103-x.
Lynch J.K., Freeman J.C., Judd A.S. et al. J. Med. Chem., 2006, vol. 49, pp. 6569–6584. https://doi.org/10.1021/jm060683e.
Sonare S.S., Vidhale N.N. Asian J. Chem., 1994, vol. 6, pp. 718–719. https://doi.org/10.1016/j.ijantimicag.2005.09.002.
Mabry T.J., Markham K.R., Thomas M.B. The systematic identification of flavonoids. Berlin-Heidelberg-New York, 1970, 354 p.
Muzychkina R.A., Korulkin D.Yu., Abilov Zh.A. Osnovy khimii prirodnykh soyedineniy. [Fundamentals of chemistry of natural compounds]. Almaty, 2010, 567 p. (in Russ.).
Rehberg N., Akone H.S. et al. ACS Infect. Dis., 2018, vol. 4, no. 2, pp. 123–134. https://doi.org/10.1021/acsinfecdis.7b00055.
Agrawal A.D. Int. J. Pharm. Sci. Nanotech., 2011, vol. 4, no. 2, pp. 1394–1398. https://doi.org/10.37285/ijpsn.2011.4.2.3.
Ivanets E.V., Dyshlova S.A., Yurchenko A.N. Aktual'nyye problemy khimii i biologii: materialy XVI Vserossiyskoy molodezhnoy shkoly-konferentsii pamyati V.Ye. Vas'kovskogo. [Current issues in chemistry and biology: materials of the XVI All-Russian youth school-conference in memory of V.E. Vaskovsky]. Vladivostok, 2017, 73 p. (in Russ.).
Syrchina A.I., Zapesochnaya G.G., Tyukaykina N.A., Voronkov M.G. Chemistry of natural compounds, 1980, vol. 16, pp. 356–358. https://doi.org/10.1007/BF00568366.
Syrchina A.I., Voronkov M.G., Tyukavkina N.A. Chemistry of natural compounds, 1973, vol. 9, p. 640. https://doi.org/10.1007/BF00564400.
Syrchina A.I., Voronkov M.G., Tyukavkina N.A. Chemistry of natural compounds, 1978, vol. 14, p. 691. https://doi.org/10.1007/BF00937640.
Kolomiets N.E., Yusubov M.S., Kalinkina G.I. Chemistry of Natural Compounds, 2012, vol. 48, no. 1, pp. 135–136. https://doi.org/10.1007/s10600-012-0181-9.
Kolomiets N.E. Farmakognosticheskoye issledovaniye roda Equisetum L.flory Sibiri kak istochnika lekarstvennykh sredstv: diss. ... dokt. farm. nauk. [Pharmacognostic study of the genus Equisetum L. of Siberian flora as a source of medicinal products: diss. ... Doctor of Pharmaceutical Sciences.]. Moscow, 2010, 414 p. (in Russ.).
Kolomiets N.E., Kalinkina G.I. Rasteniya roda khvoshch (Equisetum L.) : sistematika, khimicheskiy sostav, perspektivy ispol'zovaniya v meditsine [Plants of the genus horsetail (Equisetum L.) systematics, chemical composition, prospects for use in medicine]. Tomsk, 2009, 87p. (in Russ.).
Santesson J. Acta Chem. Scand., 1967, vol. 21, pp. 1162–1172.
Fox C.H., Huneck S. Phytochemistry, 1969, vol. 8, pp. 1301–1304.
Devlin J.P., Falshaw C.P., Ollis W.D. et al. J. Chem. Soc. (C), 1971, pp. 1318–1323. https://doi.org/10.1039/J39710001318.
Elix J., Wardlaw J. Australasian Lichenology, 2002, vol. 50, pр. 6–9.
Nash T.H., Ryan B.D., Gries C. et al. Lichen Flora of the Greater Sonoran Desert Region. Lichens Unlimite, 2004, vol. 2, 526 p.
Gao Y.H., Liu J.M., Lu H.X. et al. Gilg. Helv. Chim. Acta, 2012, vol. 95, pp. 951–954. https://doi.org/10.1080/10286020903508424.
Rahman M., Riaz M., Desai U.R. Chem. Biodiver., 2007, vol. 4, pp. 2495–2527. https://doi.org/10.1002/cbdv.200790205.
Sosnovskikh V.Y., Usachev B.I., Sizova A.Y. et al. Tetrahedron Lett., 2004, vol. 45, pp. 7351–7354.
Dembitsky V.M., Tolstikov G.A. Prirodnyye galogenirovannyye organicheskiye soyedineniya. [Natural halogenated organic compounds]. Novosibirsk, 2003, 363 р. (in Russ.).
Avramenko L.G., Nikonov G.K. Chemistry of natural compounds, 1971, vol. 7, pp. 804–805.
Musolino V., Perri M.R., Conforti F., Gliozzi M. Plants, 2023, vol. 12(3), 565. https://doi.org/10.3390/plants12030565.
Beier R.C., Wayne Ivie G., Oertli E.H. Phytochemistry, 1994, vol. 36, no. 4, pp. 869–872. https://doi.org/10.1016/S0031-9422(00)90453-9.
Engvild K.C. Phytochemistry, 1986, vol. 25, no. 4, pp. 781–791. https://doi.org/10.1016/0031-9422(86)80002-4.
Atolikshoeva S., Li J., Zhao J., Numonov S., Aisa H.A. Natural product research, 2024, vol. 38, no. 1, pp. 1–9. https://doi.org/10.1080/14786419.2022.2102627.
Numonov S., Bobakulov K., Numonova M., Sharopov F., Setzer W.N., Khalilov Q., Begmatov N., Habasi M., Aisa H.A. Natural product research, 2018, vol. 32, no. 19, pp. 2325–2332. https://doi.org/10.1080/14786419.2017.1413558.
Zheleva A., Soine T.O., Bubeva-Ivanova L. Journal of pharmaceutical sciences, 1972, vol. 61, no. 10, pp. 1643–1644. https://doi.org/10.1002/jps.2600611024.
Zheleva A., Soine T.O., Bubeva-Ivanova L. Phytochemistry, 1976, vol. 15, no. 1, pp. 209–210. https://doi.org/10.1016/S0031-9422(00)89086-X.
Filho R.B., De Moraes M.P.L., Gottlieb O.R. Phytochemistry, 1980, vol. 19, no. 9, pp. 2003–2006. https://doi.org/10.1016/0031-9422(80)83022-6.
Marques V.L.L., De Oliveira F.M., Conserva L.M., Brito R.G.L., Guilhon G.M.S.P. Phytochemistry, 2000, vol. 55, no. 7, pp. 815–818. https://doi.org/10.1016/S0031-9422(00)00296-X.
Dembitsky V.M., Tolstikov G.A. Khimiya v interesakh ustoychivogo razvitiya, 2004, no. 2, pp. 129–138. (in Russ.).
Copyright (c) 2024 Химия растительного сырья
Это произведение доступно по лицензии Creative Commons «Attribution» («Атрибуция») 4.0 Всемирная.
This work is licensed under a Creative Commons Attribution 4.0 International License.
Авторы, которые публикуются в данном журнале, соглашаются со следующими условиями:
1. Авторы сохраняют за собой авторские права на работу и передают журналу право первой публикации вместе с работой, одновременно лицензируя ее на условиях Creative Commons Attribution License, которая позволяет другим распространять данную работу с обязательным указанием авторства данной работы и ссылкой на оригинальную публикацию в этом журнале.
2. Авторы сохраняют право заключать отдельные, дополнительные контрактные соглашения на неэксклюзивное распространение версии работы, опубликованной этим журналом (например, разместить ее в университетском хранилище или опубликовать ее в книге), со ссылкой на оригинальную публикацию в этом журнале.
3. Авторам разрешается размещать их работу в сети Интернет (например, в университетском хранилище или на их персональном веб-сайте) до и во время процесса рассмотрения ее данным журналом, так как это может привести к продуктивному обсуждению, а также к большему количеству ссылок на данную опубликованную работу.