Document Type : Original Article


1 TSMU Iovel Kutateladze Institute of Pharmacochemistry, 36 P. Sarajishvili st., 0159 Tbilisi, Georgia

2 Pharmacognosy, Institute of Pharmacy, University of Innsbruck, Innsbruck, Austria


Euphorbia plants displayed a wide range of biological activities including anticancer, antitumor, anti-diabetic, anticoagulant, antiproliferative, antioxidant, cytotoxic and modulation of multidrug resistance. Euphorbia boissierana Prokh. is one of the 45 species growing in Georgia. A new lupane triterpene glycoside (1) was isolated from the MeOH extract of the aerial parts of E. boissierana. The structure of 1 was elucidated as 3-[(O-β-D-fucopyranosyl-(12)-β-D-glucopyranosyl)oxy] lup-20(29)-en-3β, 28-diol. Structure elucidation was accomplished through the extensive use of 1D- and 2D NMR experiments including 1H–1H (COSY) and 1H–13C (HSQC, HMBC) spectroscopy along with ESI-MS and HR-ESI-MS.This is the first report of the isolation of betulin glycoside from the genus Euphorbia.

Graphical Abstract

A new lupane triterpene glycoside from Euphorbia boissierana Prokh.


Main Subjects

Aalikhanipour, M., Sardari, S., Eslamifar, A., Rezvani, M., Azhar, A., Nazari, M., 2016. Evaluating the anticoagulant effect of medicinal plants in vitro by cheminformatics methods. J. Herb. Med. 6(3), 128-136.
Aslanturk O.S., Celik, T.A., 2013. Antioxidant, cytotoxic and apoptotic activities of extracts from medicinal plant Euphorbia platyphyllos L. J. Med. Plants Res. 7(19), 1293-1304.
Cateni, F., Zilic, J., Zacchigna, M., Procida, G., 2010. Cerebrosides with antiproliferative activity from Euphorbia peplis L. Fitoterapia 81(2), 97-103.
Giner, J.L., Berkowitz, J.D., Andersson, T., 2000. Nonpolarcomponents of the latex of Euphorbia peplus. J. Nat. Prod. 63(2), 267-269.
Gvazava, L.N., Alaniya, M.D., 1997. Flavonoids of Euphorbia armena. Chem. Nat. Compd. 33(2), 210.
Gvazava, L.N., Alaniya, M.D., 2000. Hydrolyzed tannins of Euphorbia glareosa leaves. Structure of glarein A. Chem. Nat. Compd. 36(2), 140-143.
Gvazava, L.N., Alaniya, M.D., 2002. Hydrolyzed tannins of Euphorbia glareosa leaves. Structure of glarein C. Chem. Nat. Compd. 38(4), 323-325.
Gvazava, L.N., Alaniya, M.D., 2005. Hydrolyzed tannin from Euphorbia glareosa leaves. Chem. Nat. Compd. 41(3), 308-310.
Gvazava, L.N., Kikoladze, V.S., 2009a. Stilbene glycosides from Euphorbia armena roots. Chem. Nat. Compd. 45(6), 859-860.
Gvazava, L.N., Kikoladze, V.S., 2009b. Cycloartane glycosides from Euphorbia glareosa. Chem. Nat. Compd. 45(4), 595-596.
Gvazava, L.N., Kikoladze, V.S., 2014. Cycloartane glycosides from Euphorbia boissierana. Chem. Nat. Compd. 50(6), 1012-1015.
Gvazava, L.N., Alaniya, M.D., Kikoladze, V.S., Kemertelidze, E.P., 1993. Triterpene glycoside from Euphorbia stricta. Proc. Geo. Nat. Acad. Sci. 19(3-4), 334-336.
Kadaev, G.N., 1963. Medicinal plants of Karachay-Cherkessia. Cherkessk, 288 p. (in Russian).
Korda, A., Pakulski, Z., Cmoch, P., Gwardiak, K., Karczewski, R., 2017. Sugar migration induced by the Wagner-Meerwein rearrangement of 28-O-glycosyl-betulin derivatives. Tetrahedron 73(13), 1740-1744.
Kpodar, M.S., Lawson-Evi, P., Bakoma, B., Eklu-Gadegbeku, K., Agbonon, A., Aklikokou, K., Gbeassor, M., 2015. Ethnopharmacological survey of plants used in the treatment of diabetes mellitus in south of Togo (Maritime Region). J. Herb. Med. 5(3), 147-152.
Muhammad, D., Lalun, N., Bobichon, H., Debar, E.L.M., Gangloff, S.C., Nour, M., Voutquenne-Nazabadioko, L., 2017. Triterpenoid saponins and other glycosides from the stems and bark of Jaffrea xerocarpa and their biological activity. Phytochemistry 141, 121-130.
Fomogne-Fodjo, M.C.Y., Ndinteh, D.T., Olivier, D.K., Kempgens, P., van Vuuren, S., Krause, R.W.M., 2017. Secondary metabolites from Tetracera potatoria stem bark with antimycobacterial activity. J. Ethnopharmacol. 195, 238-245.
Tanaka, R., Kasubuchi, K., Kita, S., Tokuda, H., Nishino, H., Matsunaga, S., 2000. Bioactive steroids from the whole herb of Euphorbia chamaesyce. J. Nat. Prod. 63(1), 99-103.
The Plant List, 2013. Version 1.1. Published on the Internet.
Vasas, A., Sulyok, E., Martins, A., Re´dei, D., Forgo, P., Kele, Z., Zupko, I., Molnar, J., Pinke, G., Hohmann, J., 2012. Cyclomyrsinane and premyrsinane diterpenes from Euphorbia falcata modulate resistance of cancer cells to doxorubicin. Tetrahedron 68(4), 1280-1285.
Yokosuka, A., Kawakami, S., Haraguchi, M., Mimaki, Y., 2011. Seven new triterpene glycosides from the pericarps of Stryphnodendron fissuratum. Phytochem. Lett. 4(3), 259-266.
Wang, G., Xu, J., 1993. Chemical study of glycosides of Oplopanax elatus Nakai. Zhongguo Yaoxue Zazhi (Beijing, China), 28(10), 593-594.