Secondary metabolites from the roots of Astragalus maximus

Document Type : Original paper


1 Department of Pharmacognosy, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran.

2 Astragalus maximus, cycloartane-type saponins, flavonoids, isoquercitrin, liquiritigenin


Background and objectives: Astragalus is one of the most abundant genera of flowering plants in Iran. There are a few reports on phytochemical investigation of this valuable genus. Saponins, flavonoids and polysaccharides have been reported as the most important metabolites in Astragalus species. In the present research, we aimed to identify the foremost constituents of Astragalus maximus. Method: Phytochemical analysis of the ethyl acetate (EtOAc) fraction of Astragalus maximus roots was performed using different methods of chromatography such as HPLC, SPE and preparative TLC. The structures of the isolated compounds were elucidated on the basis of extensive spectral evidence from 1D and 2D NMR including DQF-COSY, HSQC, HMBC, and DEPT, in comparison with reported values in the literature. Results: Analysis of the extract yielded three flavonoids namely liquiritigenin, formononetin, isoquercitrin and one acylated cycloartane-type saponin, astragaloside I. Conclusion: According to the results of our study, cycloartane-type saponin and flavonoids were the important metabolites in A. maximus.


[1] Niknam V, Ebrahimzadeh H. Phenolics content in Astragalus species. Pak J Bot. 2002; 34(3): 283-289.
[2] Turgut-Kara N, Arı S. Micropropagation of Astragalus maximus willd. Biotechnol Biotechnol Equip. 2006; 20(1): 20-22.
[3] Mozaffarian V. A dictionary of Iranian plant names. Tehran: Farhang Moaser, 2003.
[4] Siwicka D, Skopinska-Rozewska E, Bodera P. Immunotropic and anti-tumor effects of plant adaptogens. III. Astragalus (Fabaceae). Cent Eur J Immunol. 2011; 36(2): 104-107.
[5] El-Hawiet AM, Toaima SM, Asaad AM, Radwan MM, El-Sebakhy NA. Chemical constituents from Astragalus annularis Forssk. and A. trimestris L., Fabaceae. Rev Bras Farmacogn. 2010; 20(6): 860-865.
[6] Sun H, Yang Z, Ye Y. Structure and biological activity of protopanaxatriol-type saponins from the roots of Panax notoginseng. Int Immunopharmacol. 2006; 6(1): 14-25.
[7] Rıos J, Waterman P. A review of the pharmacology and toxicology of Astragalus. Phytother Res. 1997; 11(6): 411-418.
[8] Li W, Sun YN, Yan XT, Yang SY, Kim S, Lee YM, Koh Y-S, Kim YH. Flavonoids from Astragalus membranaceus and their inhibitory effects on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells. Arch Pharm Res. 2013; 37(2): 186-192.
[9] Matkowski A, Woźniak D, Lamer-Zarawska E, Oszmiański J, Leszczyńska A. Flavonoids and phenol carboxylic acids in the oriental medicinal plant Astragalus membranaceus acclimated in Poland. Z Naturforsch C. 2003; 58(7-8): 602-604.
[10] Ma X, Tu P, Chen Y, Zhang T, Wei Y, Ito Y. Preparative isolation and purification of isoflavan and pterocarpan glycosides from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography. J Chromatogr A. 2004; 1023(2): 311-315.
[11] Ma X, Tu P, Chen Y, Zhang T, Wei Y, Ito Y. Preparative isolation and purification of two isoflavones from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography. J Chromatogr A. 2003; 992(1-2): 193-197.
[12] Qi LW, Yu QT, Li P, Li SL, Wang YX, Sheng LH, Yi L. Quality evaluation of radix Astragali through a simultaneous determination of six major active isoflavonoids and four main saponins by high-performance liquid chromatography coupled with diode array and evaporative light scattering detectors. J Chromatogr A. 2006; 1134(1-2): 162-169.
[13] Pistelli L, Giachi I, Lepori E, Bertoli A. Further saponins and flavonoids from Astragalus verrucosus Moris. Pharm Biol. 2008; 41(8): 568-572.
[14] Li X, Qu L, Dong Y, Han L, Liu E, Fang S, Zhang Y, Wang T. A review of recent research progress on the Astragalus genus. Molecules. 2014; 19(11): 18850-18880.
[15] Yesilada E, Bedir E, Çalış İ, Takaishi Y, Ohmoto Y. Effects of triterpene saponins from Astragalus species on in vitro cytokine release. J Ethnopharmacol. 2005; 96(1): 71-77.
[16] Bedir E, Pugh N, Calis I, Pasco DS, Khan IA. Immunostimulatory effects of cycloartane-type triterpene glycosides from Astragalus species. Biol Pharm Bull. 2000; 23(7): 834-837.
[17] Castillo C, Valencia I, Reyes G, Hong E. 3-Nitropropionic acid, obtained from Astragalus species, has vasodilator and antihypertensive properties. Drug Dev Res. 1993; 28(2): 183-188.
[18] Luo Y, Qin Z, Hong Z, Zhang X, Ding D, Fu J-H, Zhang W-D, Chen J. Astragaloside IV protects against ischemic brain injury in a murine model of transient focal ischemia. Neurosci Lett. 2004; 363(3): 218-223.
[19] Jia R, Cao L, Xu P, Jeney G, Yin G. In vitro and in vivo hepatoprotective and antioxidant effects of Astragalus polysaccharides against carbon tetrachloride-induced hepatocyte damage in common carp (Cyprinus carpio). Fish Physiol Biochem. 2012; 38(3): 871-881.
[20] El-Sebakhy NA, Asaad AM, Abdallah RM, Toaima SM, Abdel-Kader MS, Stermitz FR. Antimicrobial isoflavans from Astragalus species. Phytochemistry. 1994; 36(6): 1387-1389.
[21] Pistelli L, Bertoli A, Lepori E, Morelli I, Panizzi L. Antimicrobial and antifungal activity of crude extracts and isolated saponins from Astragalus verrucosus. Fitoterapia. 2002; 73(4): 336-339.
[22] Song C, Zheng Z, Liu D, Hu Z. Antimicrobial isoflavans from Astragalus membranaceus (Fisch.) Bunge. Acta Bot Sin. 1996; 39(5): 486-488.
[23] Huang X, Wang D, Hu Y, Lu Y, Guo Z, Kong X, Sun J. Effect of sulfated Astragalus polysaccharide on cellular infectivity of infectious bursal disease virus. Int J Biol Macromol. 2008; 42(2): 166-171.
[24] Zhang WD, Chen H, Zhang C, Liu RH, Li HL, Chen HZ. Astragaloside IV from Astragalus membranaceus shows cardioprotection during myocardial ischemia in vivo and in vitro. Planta Med. 2006; 72(01): 4-8.
[25] Ma X, Zhang K, Li H, Han S, Ma Z, Tu P. Extracts from Astragalus membranaceus limit myocardial cell death and improve cardiac function in a rat model of myocardial ischemia. J Ethnopharmacol. 2013; 149(3): 720-728.
[26] Fathiazad F, Movafeghi A, Khosropanah M. Flavonol glycosides from the leaves of Astragalus microcephalus. Int J Biosci. 2012; 2(7): 23-28.
[27] Fathiazad F, Khosropanah M, Movafeghi A. Cycloartane-type glycosides from the roots of Astragalus caspicus Bieb. Nat Prod Res. 2010; 24(11): 1069-1078.
[28] Mitaine‐Offer AC, Miyamoto T, Semmar N, Jay M, Lacaille‐Dubois MA. A new oleanane glycoside from the roots of Astragalus caprinus. Magn Reson Chem. 2006; 44(7): 713-716.
[29] Benchadi W, Haba H, Lavaud C, Harakat D, Benkhaled M. Secondary metabolites of Astragalus cruciatus Link. and their chemotaxonomic significance. Rec Nat Prod. 2013; 7(2): 105-113.
[30] Kavtaradze NS, Alaniya M, Mshvildadze V, Skhirtladze A, Lavoie S, Pichette A. Flavonoids from Astragalus microcephalus. Chem Nat Compd. 2011; 46(6): 971-973.
[31] Yu D, Bao Y, Wei C, An L. Studies of chemical constituents and their antioxidant activities from Astragalus mongholicus Bunge. Biomed Environ Sci. 2005; 18(5): 297-301.
[32] Pu W, Wang D, Zhou D. Structural characterization and evaluation of the antioxidant activity of phenolic compounds from Astragalus taipaishanensis and their structure-activity relationship. Sci Rep. 2015; Article ID: 13914.
[33] Amado NG, Cerqueira DM, Menezes FS, da Silva JFM, Neto VM, Abreu JG. Isoquercitrin isolated from Hyptis fasciculata reduces glioblastoma cell proliferation and changes β-catenin cellular localization. Anti-cancer Drug. 2009; 20(7): 543-552.
[34] Krasteva I, Nikolov S. Flavonoids in Astragalus corniculatus. Quim Nova. 2008; 31(1): 59-60.
[35] Guzhva NN. Flavonoids and hydroxycinnamic acids from Astragalus asper. Chem Nat Compd. 2010; 46(2): 303-304.
[36] Hirotani M, Zhou Y, Lui H, Furuya T. Astragalosides from hairy root cultures of Astragalus membranaceus. Phytochemistry. 1994; 36(3): 665-670.
[37] Polat E, Bedir E, Perrone A, Piacente S, Alankus-Caliskan O. Triterpenoid saponins from Astragalus wiedemannianus Fischer. Phytochemistry. 2010; 71(5-6): 658-662.
[38] Horo I, Bedir E, Masullo M, Piacente S, Ozgokce F, Alankus-Caliskan O. Saponins from Astragalus hareftae (NAB.) SIRJ. Phytochemistry. 2012; 84: 147-153.
[39] Kondeva-Burdina MS, Bratkov V, Simeonova RL, Vitcheva VB, Krasteva IN, Zdraveva PK. Protective effects of saponin mixture, isolated from Astragalus monspessulanus subsp. monspessulanus on tert-butyl hydroperoxide-induced oxidative stress in isolated rat hepatocytes. Am J Plant Sci. 2015; 6(06): 799-802.
[40] Bratkov VM, Shkondrov AM, Zdraveva PK, Krasteva IN. Flavonoids from the genus Astragalus: phytochemistry and biological activity. Pharmacogn Rev. 2016; 10(19): 11-32.