EUDESMANE SESQUITERPENE LACTONES OF THE GENUS INULA AND THEIR BIOLOGICAL ACTIVITY
UDC 547.913.5+582.5/.9
Abstract
Sesquiterpene lactones (SL) are widely distributed in nature (formed biosynthetically in plants from farnesyl pyrophosphate) and are a structurally diverse class of terpenoids with 15 carbon atoms in the skeleton and, in addition to the lactone cycle, can contain various functional groups. Some of them exhibit biological activity both in a rather wide range and in relation to a specific target. An increase in the number of undescribed natural plant compounds of this class, as well as detection in various plant species, opens up new possibilities for their use for the purposes of medical chemistry, phytochemistry, pharmacognosy, chemotaxonomy, and related fields. Using the example of SL of the eudesmane structural type found in plants of the genus Inula, this review attempts to show the relevance of studies of such compounds that investigate the mechanism of action on various biological models, including the goal of developing new effective antitumor agents.
Downloads
Metrics
References
Seigler D.S. Plant secondary metabolism. 1st Edn. NewYork, 1998, 760 p.
Fraga B.M. Natural Product Reports, 2013, vol. 30, no. 9, pp. 1226–1264. DOI: 10.1039/c3np70047j.
Rodriguez E., Towers G.H.N., Mitchell J.C. Phytochemistry, 1976, vol. 15, no. 11, pp. 1573–1580. DOI: 10.1016/S0031-9422(00)97430-2.
Rybalko K.S. Prirodnyye seskviterpenovyye laktony. [Natural sesquiterpene lactones]. Moscow, 1978, 319 p. (in Russ.).
Picman A.K. Biochemical Systematics and Ecology, 1986, vol. 14, no. 3, pp. 255–281. DOI: 10.1016/0305-1978(86)90101-8.
Kagarlitskiy A.D., Adekenov S.M., Kupriyanov A.N. Seskviterpenovyye laktony rasteniy Tsentral'nogo Kazakhstana. [Sesquiterpene lactones of plants of Central Kazakhstan]. Alma-Ata, 1987, 240 p. (in Russ.).
Chaturvedi D. Opportunity, Challanges and Scope of Natural Products in Medicinal Chemistry. Trivandrum, India, 2011, pp. 313–334.
Sharma A., Bajpai V.K., Shukla S. Natural Products. Berlin; Heidelberg, 2013, pp. 3515–3550.
Hohmann M.S.N., Longhi-Balbinot D.T., Guazelli C.F.S., Navarro S.A., Zarpelon A.C., Casagrande R., Arakawa N.S., Verri W.A. Jr. Studies in Natural Products Chemistry, 2016, vol. 49, pp. 243–264. DOI: 10.1016/B978-0-444-63601-0.00007-7.
Padilla-Gonzalez G.F., dos Santos F.A., Da Costa F.B. Critical Reviews in Plant Sciences, 2016, vol. 35, no. 1, pp. 18–37. DOI: 10.1080/07352689.2016.1145956.
Kreuger M.R.O., Grootjans S., Biavatti M.W., Vandenabeele P., D’Herde K. Anticancer Drugs, 2012, vol. 23, no. 9, pp. 883–896. DOI: 10.1097/CAD.0b013e328356cad9.
Sülsen V.P., Martino V.S. Sesquiterpene lactones. Cham, 2018, 371 p. DOI: 10.1007/978-3-319-78274-4.
Zidorn C. Phytochemistry, 2008, vol. 69, no. 12, pp. 2270–2296. DOI: 10.1016/j.phytochem.2008.06.013.
Wu Q.-X., Shi Y.-P., Jia Z.-J. Natural Product Reports, 2006, vol. 23, no. 5, pp. 699–734. DOI: 10.1039/B606168K.
Adekenov S.M. Chemistry of Natural Compounds, 1995, vol. 31, no. 1, pp. 21–25. DOI: 10.1007/BF01167564.
Zhao Y.M., Zhang M.L., Shi Q.W., Kiyota H. Chemistry and Biodiversity, 2006, vol. 3, no. 4, pp. 371–384. DOI: 10.1002/cbdv.200690041.
Huo Y., Shi H.M., Wang M.Y., Li X.B. Die Pharmazie – An International Journal of Pharmaceutical Sciences, 2008, vol. 63, no. 10, pp. 699–703. DOI: 10.1691/ph.2008.8566.
Khan A.L., Hussain J., Hamayun M., Gilani S.A., Ahmad S., Rehman G., Kim Y.-H., Kang S.-M., Lee I.-J. Mole-cules, 2010, vol. 15, no. 13, pp. 1562–1577. DOI: 10.3390/molecules15031562.
Wang G.-W., Qin J.-J., Cheng X.-R., Shen Y.-H., Shan L., Jin H.-Z., Zhang W.-D. Expert Opinion on Investigational Drugs, 2014, vol. 23, no. 3, pp. 317–345. DOI: 10.1517/13543784.2014.868882.
Seca A.M.L., Pinto D.C.G.A., Silva A.M.S. Chemistry and Biodiversity, 2015, vol. 12, no. 6, pp. 859–906. DOI: 10.1002/cbdv.201400080.
Sharma V., Hem K., Sharma D., Singh V., Singh D.N. Journal of Natural Products and Resources, 2016, vol. 2, no. 1, pp. 40–46.
Tavares W.R., Seca A.M.L. Antioxidants, 2019, vol. 8, no. 5, pp. 122. DOI: 10.3390/antiox8050122.
Quintana J., Estévez F. Current Pharmaceutical Design, 2019. vol. 24, no. 36, pp. 4355–4361. DOI: 10.2174/1381612825666190119114323.
Marshall J.A., Cohen N. Journal of Organic Chemistry, 1964, vol. 29, no. 12, pp. 3727–3729. DOI: 10.1021/jo01035a527.
Jacobs W.A., Elderfield R.C. Annual Review of Biochemistry, 1938, vol. 7, no. 1, pp. 449–472. DOI: 10.1146/annurev.bi.07.070138.002313.
Milman I.A. Chemistry of Natural Compounds, 1990, vol. 26, no. 3, pp. 251–262. DOI: 10.1007/BF00597842.
Šunjić V. Kemija u Industriji, 2017, vol. 66, no. 1–2, pp. 29–46. DOI: 10.15255/KUI.2016.008.
Ma X.-C., Liu K.-X., Zhang B.-J., Xin X.-L., Huang J. Magnetic Resonance in Chemistry, 2008, vol. 46, no. 11, pp. 1084–1088. DOI: 10.1002/mrc.2297.
Xu L.-W., Shi Y.-P. Journal of Asian Natural Products Research, 2011, vol. 13, no. 6, pp. 570–574. DOI: 10.1080/10286020.2011.575066.
Sharma M., Sharma A., Singh R., Katiyar C.K. Pharmacia Sinica, 2011, vol. 2, no. 6, pp. 6–10.
Stojakowska A., Michalska K., Malarz J. Phytochemical Analysis, 2006, vol. 17, no. 3, pp. 157–161. DOI: 10.1002/pca.900.
Rasul A., Khan M., Ali M., Li J., Li X. Scientific World Journal, 2013, vol. 2013, art. ID 248532. DOI: 10.1155/2013/248532.
Seo J.Y., Lim S.S., Kim J.R., Lim J.-S., Ha Y.R., Lee I.A., Kim E.J., Park J.H.Y., Kim J.-S. Phytherapy Research, 2008, vol. 22, no. 11, pp. 1500–1505. DOI: 10.1002/ptr.2521.
Shi Y., Bao Y.L., Wu Y., Yu C.L., Huang Y.X., Sun Y., Zheng L.H., Li Y.X. Journal of Biomolecular Screening, 2011, vol. 16, no. 5, pp. 525–535. DOI: 10.1177/1087057111398486.
Zong C.H.M., Zhao Y., Zhang K., Yang L., Zheng Y. Chemical Research in Chinese Universities, 2011, vol. 27, no. 2, pp. 241–244.
Maryam A., Mehmood T., Zhang H., Li Y., Khan M., Ma T. Scientific Reports, 2017, vol. 7, no. 1, 6242. DOI: 10.1038/s41598-017-06535-y.
Lawrence N.J., McGown A.T., Nduka J., Hadfield J.A., Pritchard R.G. Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, no. 3, pp. 429–431. DOI: 10.1016/S0960-894X(00)00686-7.
Wei W., Huang H., Zhao S., Liu W., Liu C.-X., Chen L., Li J.-M., Wu Y.-L., Yan H. Apoptosis, 2013, vol. 18, no. 9, pp. 1060–1070. DOI: 10.1007/s10495-013-0854-2.
Ding Y., Gao H., Zhang Y., Li Y., Vasdev N., Gao Y., Chen Y., Zhang Q. Journal of Hematology and Oncology, 2016, vol. 9, no. 1, 93. DOI: 10.1186/s13045-016-0327-5.
Yao Y., Xia D., Bian Y., Sun Y., Zhu F., Pan B., Niu M., Zhao K., Wu Q., Qiao J., Fu C., Li Z., Xu K. Apoptosis, 2015, vol. 20, no. 8, pp. 1122–1133. DOI: 10.1007/s10495-015-1140-2.
Zhang Y., Bao Y.L., Wu Y., Yu C.L., Huang Y.X., Sun Y., Zheng L.H., Li Y.X. Molecular Medicine Reports, 2013, vol. 8, no. 4, pp. 967–972. DOI: 10.3892/mmr.2013.1640.
Mi X.-G., Song Z.-B., Wu P., ZhangY.-W., Sun L.-G., BaoY.-L., ZhangY., Zheng L.-H., Sun Y., Yu C.-L., Wu Y., Wang G.-N., Li Y.-X. Toxicology Letters, 2014, vol. 224, no. 3, pp. 349–355. DOI: 10.1016/j.toxlet.2013.11.002.
Zhang J., Li Y., Duan D., Yao J., Gao K., Fang J. Biochemical Pharmacology, 2016, vol. 102, no. 1, pp. 34–44. DOI: 10.1016/j.bcp.2015.12.004.
Rezeng C., Yuan D., Long J., Suonan D., Yang F., Li W., Tong L., Jiumei P. Bioscience Trends, 2015, vol. 9, no. 6, pp. 420–422. DOI: 10.5582/bst.2015.01171.
Lei J.-C., Yu J.-Q., Yin Y., Liu Y.-W., Zou G.-L. Food and Chemical Toxicology, 2012, vol. 50, no. 9, pp. 3313–3319. DOI: 10.1016/j.fct.2012.06.014.
Khan M., Yi F., Rasul A., Li T., Wang N., Gao H., Gao R., Ma T. IUBMB Life, 2012, vol. 64, no. 9, pp. 783–794. DOI: 10.1002/iub.1068.
Khan M., Li T., Khan M.K.A., Rasul A., Nawaz F., Sun M., Zheng Y., Ma T. BioMed Research International, 2013, vol. 2013, 719858. DOI: 10.1155/2013/719858.
Wang X., Yu Z., Wang C., Cheng W., Tian X., Huo X., Wang Y., Sun C., Feng L., Xing J., Lan Y., Sun D., Hou Q., Zhang B., Ma Xi., Zhang Bo. Journal of Experimental and Clinical Cancer Research, 2017, vol. 36, no. 1, 93. DOI: 10.1186/s13046-017-0563-8.
Cui L., Bu W., Song J., Feng L., Xu T., Liu D., Ding W., Wang J., Li C., Ma B., Luo Y., Jiang Z., Wang C., Chen J., Hou J., Yan H., Yang L., Jia X. Archives of Pharmacal Research, 2018, vol. 41, no. 3, pp. 299–313. DOI: 10.1007/s12272-017-0990-2.
He R., Shi X., Zhou M., Zhao Y., Pan S., Zhao C., Guo X., Wang M., Xu L., Qin R. Toxicology and Applied Phar-macology, 2018, vol. 356, pp. 159–171. DOI: 10.1016/j.taap.2018.08.003.
Konishi T., Shimada Y., Nagao T., Okabe H., Konoshima T. Biological and Pharmaceutical Bulletin, 2002, vol. 25, no. 10, pp. 1370–1372. DOI: 10.1248/bpb.25.1370.
Yang C., Wang C.-M., Jia Z.-J. Planta Medica, 2003, vol. 69, no. 7, pp. 662–666. DOI: 10.1055/s-2003-41123.
Wu M., Zhang H., Hu J., Weng Z., Li C., Li H., Zhao Y., Mei X., Ren F., Li L. PLoS One, 2013, vol. 8, no. 9, e76000. DOI: 10.1371/journal.pone.0076000.
Rasul A., Khan M., Yu B., Ali M., Bo Y.J., Yang H., Ma T. Archives of Pharmacal Research, 2013, vol. 36, no. 10, pp. 1262–1269. DOI: 10.1007/s12272-013-0217-0.
Kauffmann-Zeh A., Rodriguez-Viciana P., Ulrich E., Gilbert C., Coffer P., Downward J., Evan G. Nature, 1997, vol. 385, pp. 544–548. DOI: 10.1038/385544a0.
Rasul A., Di J., Millimouno F.M., Malhi M., Tsuji I., Ali M., Li J., Li X. Molecules, 2013, vol. 18, no. 8, pp. 9382–9396. DOI: 10.3390/molecules18089382.
Li Y., Ni Z.-Y., Zhu M.-C., Dong M., Wang S.-M., Shi Q.-W., Zhang M.-L., Wang Y.-F., Huo C.-H., Kiyota H., Cong B. Zeitschrift für Naturforschung C, 2012, vol. 67, no. 7–8, pp. 375–380. DOI: 10.1515/znc-2012-7-804.
Lim S.S., Kim J.R., Lim H.A., Jang C.H., Kim Y.K., Konishi T., Kim E.J., Park J.H.Y., Kim J.-S. Journal of Medici-nal Food, 2007, vol. 10, no. 3, pp. 503–510. DOI: 10.1089/jmf.2006.209.
Pukhov S.A., Afanas’eva S.V., Anikina L.V., Kozlovskii V.I., Neganova M.E., Klochkov S.G. Chemistry of Natural Compounds, 2019, vol. 55, no. 1, pp. 41–46. DOI: 10.1007/s10600-019-02611-z.
Klochkov S.G., Pukhov S.A., Neganova M.Ye., Dubrovskaya Ye.S., Anikina L.V., Afanas'yeva S.V., Semakov A.V. Biomedical Chemistry: Research and Methods, 2018, vol. 1, no. 3, e000471. DOI: 10.18097/BMCRM00047. (in Russ.).
Konishi T., Kondo S., Uchiyama N. Applied Entomology and Zoology, 2008, vol. 43, no. 1, pp. 77–81. DOI: 10.1303/aez.2008.77.
Burova L.G., Shirokikh I.V., Patrushev S.S.,. Tolstikova T.G, Shul'ts E.E. Fundamental'naya i klinicheskaya meditsi-na, 2017, vol. 2, no. 1, pp. 28–34. (in Russ.).
Liu C.H., Mishra A.K., Tan R. Crop Protection, 2006, vol. 25, no. 5, pp. 508–511. DOI: 10.1016/j.cropro.2005.05.008.
Kaur M., Kumar R., Upendrabhai D.P., Singh I.P., Kaur S. Pest Management Science, 2017, vol. 73, no. 5, pp. 1031–1038. DOI: 10.1002/ps.4429.
Liu C., Mishra A.K., He B., Tan R. Chinese Science Bulletin, 2001, vol. 46, no. 6, pp. 498–501. DOI: 10.1007/BF03187267.
Arha D., Ramakrishna E., Gupta A.P., Rai A.K., Sharma A., Ahmad I., Riyazuddin M., Gayen J.R., Maurya R., Tamrakar A.K. Molecular and Cellular Endocrinology, 2018, vol. 460, no 1, pp. 134–151. DOI: 10.1016/j.mce.2017.07.015.
Yao D., Wang Y., Huo C., Wu Y., Zhang M., Li L., Shi Q., Kiyota H., Shi X. Food Chemistry, 2017, vol. 214, no. 1, pp. 328–338. DOI: 10.1016/j.foodchem.2016.07.100.
Zhou B., Ye J., Yang N., Chen L., Zhuo Z., Mao L., Liu Q., Lan G., Ning J., Ge G., Yang L., Shen Y., Wang S., Zhang W. Journal of Chromatography B, 2018, vol. 1072, no. 1, pp. 370–378. DOI: 10.1016/j.jchromb.2017.11.039.
Xu R., Peng Y., Wang M., Li X. European Journal of Drug Metabolism and Pharmacokinetics, 2019, vol. 44, no. 2, pp. 295–303. DOI: 10.1007/s13318-018-0510-x.
Bhandari P., Rastogi R.P. Indian Journal of Chemstry, Section B, 1983, vol. 22, no. 3, pp. 286–287.
Huo Y., Shi H., Li W., Wang M., Li X. Journal of Pharmaceutical and Biomedical Analysis, 2010, vol. 51, no. 4, pp. 942–946. DOI: 10.1016/j.jpba.2009.09.032.
Jiang H.-L., Chen J., Jin X.-J., Yang J.-L., Li Y., Yao X.-J., Wu Q.-X. Tetrahedron, 2011, vol. 67, no. 47, pp. 9193–9198. DOI: 10.1016/j.tet.2011.09.070.
Bohlmann F., Mahanta P.K., Jakupovic J., Rastogi R.C., Natu A.A. Phytochemistry, 1978, vol. 17, no. 7, pp. 1165–1172. DOI: 10.1016/S0031-9422(00)94308-5.
Khvorost P.P., Komissarenko N.F. Chemistry of Natural Compounds, 1976, vol. 12, no. 6, pp. 740–741. DOI: 10.1007/BF00564986.
Su B.-N., Takaishi Y., Yabuuchi T., Kusumi T., Tori M., Takaoka S., Honda G., Ito M., Takeda Y., Kodzhi-matov O.K., Ashurmetov O. Journal of Natural Products, 2001, vol. 64, no. 4, pp. 466–471. DOI: 10.1021/np000211h.
Kerimov S.S., Chizhov O.S. Chemistry of Natural Compounds, 1974, vol. 10, no. 2, pp. 267–267. DOI: 10.1007/BF00563642.
Ravindranath K.R., Raghavan R., Paknikar S.K., Trivedi G.K., Bhattacharyya S.C. Indian Journal of Chemistry, Sec-tion B, 1978, vol. 16, no. 1, pp. 27–31.
Kashman Y., Lavie D., Glotter E. Israel Journal of Chemistry, 1967, vol. 5, no. 1, pp. 23–27. DOI: 10.1002/ijch.196700004.
Shah W.A., Dar M.Y., Qurishi M.A. Journal of Research and Education in Indian Medicine, 2009, vol. 15, no. 1, pp. 11–14.
Jakupovic J., Jaensch M., Bohlmann F., Dillon M.O. Phytochemistry, 1988, vol. 27, no. 11, pp. 3551–3556. DOI: 10.1016/0031-9422(88)80767-2.
Goyal R., Chhabra B.R., Kalsi P.S. Phytochemistry, 1990, vol. 29, no. 7, pp. 2341–2343. DOI: 10.1016/0031-9422(90)83069-D.
Wu X.-D., Ding L.-F., Tu W.-C., Yang H., Su J., Peng L.-Y., Li Y., Zhao Q.-S. Phytochemistry, 2016, vol. 129, no. 1, pp. 68–76. DOI: 10.1016/j.phytochem.2016.07.008.
Trendafilova A., Ivanova V., Todorova M., Aneva I. Phytochemistry Letters, 2017, vol. 21, pp. 221–225. DOI: 10.1016/j.phytol.2017.07.008.
Kalsi S., Goyal R., Talwar K.K., Chhabra B.R. Phytochemistry, 1989, vol. 28, no. 8, pp. 2093–2096. DOI: 10.1016/S0031-9422(00)97926-3.
Cantrell C.L., Abate L., Fronczek F.R., Franzblau S.G., Quijano L., Fischer N.H. Planta Medica, 1999, vol. 65, no. 4, pp. 351–355. DOI: 10.1055/s-1999-14001.
Ma Y.-Y., Zhao D.-G., Gao K. Journal of Natural Products, 2013, vol. 76, no. 4, pp. 564–570. DOI: 10.1021/np300742d.
Herz W., Sumi Y., Sudarsanam V., Raulais D. Journal of Organic Chemistry, 1967, vol. 32, no. 11, pp. 3658–3662. DOI: 10.1021/jo01286a079.
Cheng X.-R., Zhang S.-D., Wang C.-H., Ren J., Qin J.-J., Tang X., Shen Y.-H., Yan S.-K., Jin H.-Z., Zhang W.-D. Phytochemistry, 2013, vol. 96, pp. 214–222. DOI: 10.1016/j.phytochem.2013.10.006.
Wang T., Guo S., Zhang S., Yue W., Ho C.-T., Bai N. Analytical Methods, 2019, vol. 11, no. 13, pp. 1822–1833. DOI: 10.1039/C9AY00118B.
Shi X.-W., Qi J.-L., Wu Y.-B., Fu Y., Wang Y.-Z., Zhang D.-Q. Chromatographia, 2008, vol. 68, no. 3–4, pp. 281–285. DOI: 10.1365/s10337-008-0698-z.
Nikonova L.P., Nikonov G.K. Chemistry of Natural Compounds, 1970, vol. 6, no. 1, pp. 128–129. DOI: 10.1007/BF00564183.
Qin J.-J., Jin H.-Z., Zhu J.-X., Fu J.-J., Zeng Q., Cheng X.-R., Zhu Y., Shan L., Zhang S.-D., Pan Y.-X., Zhang W.-D. Tetrahedron, 2010, vol. 66, no. 48, pp. 9379–9388. DOI: 10.1016/j.tet.2010.09.091.
Herz W., Hogenaue. G. Journal of Organic Chemistry, 1962, vol. 27, no. 3, pp. 905–910. DOI: 10.1021/jo01050a052.
Topçu G., Öksüz S., Shieh H.-L., Cordell G.A., Pezzuto J.M., Bozok-Johansson C. Phytochemistry, 1993, vol. 33, no. 2, pp. 407–410. DOI: 10.1016/0031-9422(93)85529-Z.
Ito K., Iida T. Phytochemistry, 1981, vol. 20, no. 2, pp. 271–273. DOI: 10.1016/0031-9422(81)85105-9.
Benešová V., Herout V., Šorm F. Collection of Czechoslovak Chemical Communications, 1961, vol. 26, no. 5, pp. 1350–1357. 10.1135/cccc19611350.
Ding Y., Pan W., Xu J., Wang T., Chen T., Liu Z., Xie C., Zhang Q. Bioorganic Chemistry, 2019, vol. 86, pp. 363–367. DOI: 10.1016/j.bioorg.2019.01.055.
Bohlmann F., Zdero C. Phytochemistry, 1977, vol. 16, no. 8, pp. 1243–1245. DOI: 10.1016/S0031-9422(00)94366-8.
Herz W., Subramaniam P.S., Geissman T.A. Journal of Organic Chemistry, 1968, vol. 33, no. 10, pp. 3743–3749. DOI: 10.1021/jo01274a013.
Andolfi A., Zermane N., Cimmino A., Avolio F., Boari A., Vurro M., Evidente A. Phytochemistry, 2013, vol. 86, pp. 112–120. DOI: 10.1016/j.phytochem.2012.10.003.
Qin J.-J., Zhu J.-X., Zeng Q., Cheng X.-R., Zhang S.-D., Jin H.-Z., Zhang W.-D. Planta Medica, 2012, vol. 78, no. 10, pp. 1002–1009. DOI: 10.1055/s-0031-1298621.
Doskotch R.W., Hufford C.D., El-Feraly F.S. Journal of Organic Chemistry, 1972, vol. 37, no. 17, pp. 2740–2744. DOI: 10.1021/jo00982a025.
Bohlmann F., Jakupovic J., Ates N., Schuster A., Pickardt J., King R.M., Robinson H. Justus Liebigs Annalen der Chemie, 1983, vol. 1983, no. 6, pp. 962–973. DOI: 10.1002/jlac.198319830609.
Cheng X., Zeng Q., Ren J., Qin J., Zhang S., Shen Y., Zhu J., Zhang F., Chang R., Zhu Y., Zhang W., Jin H. Europe-an Journal of Medicinal Chemistry, 2011, vol. 46, no. 11, pp. 5408–5415. DOI: 10.1016/j.ejmech.2011.08.047.
Öksüz S., Topcu G., Krawiec M., Watson W.H. Phytochemistry, 1997, vol. 46, no. 6, pp. 1131–1134. DOI: 10.1016/S0031-9422(97)00399-3.
Zhang T., Gong T., Yang Y., Chen R.-Y., Yu D.-Q. Phytochemistry Letters, 2012, vol. 5, no. 2, pp. 229–232. DOI: 10.1016/j.phytol.2011.12.014.
Al-Yahya M.A., Khafagy S., Shihata A., Kozlowski J.F., Antoun M.D., Cassady J.M. Journal of Natual Products, 1984, vol. 47, no. 6, pp. 1013–1017. DOI: 10.1021/np50036a019.
Zhang T., Xiao W., Gong T., Yang Y., Chen R.-Y., Yu D.-Q. Journal of Asian Natural Products Research, 2010, vol. 12, no. 9, pp. 788–792. DOI: 10.1080/10286020.2010.504662.
Qin J.-J., Jin H.-Z., Huang Y., Zhang S.-D., Shan L., Voruganti S., Nag S., Wang W., Zhang W.-D., Zhang R. Euro-pean Journal of Medicinal Chemistry, 2013, vol. 68, pp. 473–481. DOI: 10.1016/j.ejmech.2013.07.018.
Zhao Y.-M., Wang Y.-j., Dong M., Zhang M.-L., Huo C.-H., Gu Y.-C., Shi Q.-W. Chemistry of Natural Compounds, 2010, vol. 46, no. 3, pp. 373–376. DOI: 10.1007/s10600-010-9620-7.
Zhang S.-D., Qin J.-J., Jin H.-Z., Yin Y.-H., Li H.-L., Yang X.-W., Li X., Shan L., Zhang W.-D. Planta Medica, 2012, vol. 78, no. 2, pp. 166–171. DOI: 10.1055/s-0031-1280294.
Fu B., Su B.-N., Takaishi Y., Honda G., Ito M., Takeda Y., Kodzhimatov O.K., Ashurmetov O. Phytochemistry, 2001, vol. 58, no 7, pp. 1121–1128. DOI: 10.1016/S0031-9422(01)00334-X.
Yan H., Haiming S., Cheng G., Xiaobo L. Chemistry of Natural Compounds, 2012, vol. 48, no. 3, pp. 522–524. DOI: 10.1007/s10600-012-0298-x.
Romo de Vivar A., Jiménez H. Tetrahedron, 1965, vol. 21, no. 7, pp. 1741–1745. DOI: 10.1016/S0040-4020(01)98644-2.
Garayev E., Herbette G., Di Giorgio C., Chiffolleaud P., Rouxe D., Sallanone H., Olliviera E., Eliasa R., Baghdikiana B. Fitoterapia, 2017, vol. 120, pp. 79–84. DOI: 10.1016/j.fitote.2017.05.011.
Yoshioka H., Renold W., Fischer N.H., Higo A., Mabry T.J. Phytochemistry, 1970, vol. 9, no. 4, pp. 823–832. DOI: 10.1016/S0031-9422(00)85188-2.
Sanz J.F., Castellano G., Marco J.A. Phytochemistry, 1990, vol. 29, no. 2, pp. 541–545. DOI: 10.1016/0031-9422(90)85114-U.
Metwally M.A., Dawidar A.A. Pharmazie, 1984, vol. 39, no. 8, pp. 575–576.
de Trimarco J.T., de Riscala E.C., Catalán C.A.N., Griffin C.L., Herz W. Biochemical Systematics and Ecology, 2004, vol. 32, no. 11, pp. 1063–1067. DOI: 10.1016/j.bse.2004.02.013.
Nikonova L.P., Nikonov G.K. Chemistry of Natural Compounds, 1972, vol. 8, no. 3, pp. 286–289. DOI: 10.1007/BF00563730.
Fischedick J.T., Pesic M., Podolski-Renic A., Bankovic J., de Vos R.C.H., Perić M., Todorović S., Tanic N. Phyto-chemistry Letters, 2013, vol. 6, no. 2, pp. 246–252. DOI: 10.1016/j.phytol.2013.02.006.
Bohlmann F., Jakupovic J., Schuster A. Phytochemistry, 1981, vol. 20, no. 8, pp. 1891–1893. DOI: 10.1016/0031-9422(81)84029-0.
Zhang X.-F., Du J.-L., Ren J., Ye F.-M., Xie Y.-G., Cheng X.-R., Yan S.-K., Jin H.-Z. Archives of Pharmacal Re-search, 2015, vol. 38, no. 5, pp. 666–672. DOI: 10.1007/s12272-014-0388-3.
Bai N., Zhou B.-N., Zhang L., Sang S., He K., Zheng Q.Y. Oriental Foods and Herbs: Chemistry and Health Benefits (ACS Symposium Series, No. 859). Washington, DC, 2003, pp. 271–278.
Yoshioka H., Mabry T.J., Dennis N., Herz W. Journal of Organic Chemistry, 1970, vol. 35, no, 3, pp. 627–631. DOI: 10.1021/jo00828a017.
González-Romero M.A., Villaescusa-Castillo L., Díaz-Lanza A.M. Zeitschrift für Naturforschung C, 2000, vol. 55, no. 9–10, pp. 697–700. DOI: 10.1515/znc-2000-9-1005.
Serkerov S.V., Mir-Babaev N.F. Chemistry of Natural Compounds, 1988, vol. 24, no. 6, pp. 752–753. DOI: 10.1007/BF00598206.
Adekenov S.M., Abdykalykov M.A. Chemistry of Natural Compounds, 1990, vol. 26, no. 3, pp. 338–338. DOI: 10.1007/BF00597866.
Park E., Kim J. Planta Medica, 1998, vol. 64, no. 8, pp. 752–754. DOI: 10.1055/s-2006-957573.
Vajs V., Nevešćanin M., Macura S., Juranić N., Menković N., Milosavljević S. Fitoterapia, 2003, vol. 74, no. 5, pp. 508–510. DOI: 10.1016/S0367-326X(03)00115-1.
Pandey U.C., Sharma R.P., Kulanthaivel P., Herz W. Phytochemistry, 1985, vol. 24, no. 7, pp. 1509–1514. DOI: 10.1016/S0031-9422(00)81056-0.
Stefanovic M., Ristic N., Djermanovic M., Mladenovic S. Planta Medica, 1980, vol. 39, no. 3, pp. 264–264.
Jeske F., Huneck S., Jakupovic J. Phytochemistry, 1993, vol. 34, no. 6, pp. 1647–1649. DOI: 10.1016/S0031-9422(00)90865-3.
Jeske F., Huneck S., Jakupovic J. Phytochemistry, 1996, vol. 41, no. 6, pp. 1539–1542. DOI: 10.1016/0031-9422(95)00807-1.
Gong H.-Q., Wu Q.-X., Liu L.-L., Yang J.-L., Wang R., Shi Y.-P. Helvetica Chimica Acta, 2011, vol. 94, no. 7, pp. 1269–1276. DOI: 10.1002/hlca.201000417.
Jakupovic J., Lehmann L., Bohlmann F., King R.M., Robinson H. Phytochemistry, 1988, vol. 27, no. 12, pp. 3831–3839. DOI: 10.1016/0031-9422(88)83027-9.
Mahmoud Z.F., Salam N.A.A., Sarg T.M., Bohlmann F. Phytochemistry, 1981, vol. 20, no. 4, pp. 735–738. DOI: 10.1016/0031-9422(81)85164-3.
Zdero C., Bohlmann F., Müller M. Phytochemistry, 1987, vol. 26, no. 10, pp. 2763–2775. DOI: 10.1016/S0031-9422(00)83588-8.
Stagno-d’Alcontres G., Gattuso M., Aversa M.C., Caristi C. Gazzetta Chimica Italiana, 1973, vol. 103, pp. 239–246.
Asakawa Y., Toyota M., Takemoto T., Suire C. Phytochemistry, 1979, vol. 18, no. 6, pp. 1007–1009. DOI: 10.1016/S0031-9422(00)91465-1.
Zaima K., Wakana D., Demizu Y., Kumeta Y., Kamakura H., Maruyama T., Kurihara M., Goda Y. Journal of Natural Medicines, 2014, vol. 68, no. 2, pp. 432–435. DOI: 10.1007/s11418-013-0806-8.
Huo Y., Shi H., Wang M., Li X. Magnetic Resonance in Chemistry, 2008, vol. 46, no. 12, pp. 1208–1211. DOI: 10.1002/mrc.2340.
Matsueda S., Geissman T.A. Tetrahedron Letters, 1967, vol. 8, no. 21, pp. 2013–2015. DOI: 10.1016/S0040-4039(00)90776-7.
Rybalko K.S., Ban'kovskiy A.I., Perel'son M.Ye. Meditsinskaya promyshlennost' SSSR, 1960, vol. 10, pp. 21–23. (in Russ.).
Rybalko K.S., Dolejš L. Collection Czechoslovak Chemical Communications, 1961, vol. 26, no. 11, pp. 2909–2915. DOI: 10.1135/cccc19612909.
Geissman T.A., Ellestad G.A. Journal of Organic Chemistry, 1962, vol. 27, no. 5, pp. 1855–1859. DOI: 10.1021/jo01052a092.
Huang-Minlon. Journal of American Chemical Society, 1948, vol. 70, no. 2, pp. 611–614. DOI: 10.1021/ja01182a050.
Yoshikawa J.Y.M., Hatakeyama S., Inoue Y. Chemical and Pharmaceutical Bulletin, 1993, vol. 41, no. 1, pp. 214–216. DOI: 10.1248/cpb.41.214.
Kaur B., Kalsi P.S. Phytochemistry, 1985, vol. 24, no. 9, pp. 2007–2010. DOI: 10.1016/S0031-9422(00)83111-8.
Kalsi P.S., Goyal R., Talwar K.K., Chhabra B.R. Phytochemistry, 1988, vol. 27, no. 7, pp. 2079–2081. DOI: 10.1016/0031-9422(88)80100-6.
Wang C.-M., Jia Z.-J., Zheng R.-L. Planta Medica, 2007, vol. 73, no. 2, pp. 180–184. DOI: 10.1055/s-2006-957080.
Pukhov S.A., Afanasyeva S.V., Anikina L.V., Semakov A.V., Dubrovskaya E.S., Klochkov S.G. Russian Journal of Bioorganic Chemistry, 2018, vol. 44, no. 5, pp. 553–561. DOI: 10.1134/S1068162018040155.
Copyright (c) 2021 chemistry of plant raw material
This work is licensed under a Creative Commons Attribution 4.0 International License.
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.
