Triterpene Glycosides from Astragalus angustifolius

Abstract

Six new cycloartane-type (1–6) and four new oleanane-type (7–10) triterpene glycosides were isolated from Astragalus angustifolius Lam., together with five known triterpene glycosides. Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Compounds 1–3 are glycosides of cycloastragenol, while compounds 4–6 show the C-24 epimer of cycloastragenol as aglycone, encountered for the first time in nature. All compounds were evaluated for their antiproliferative activity in Hela, H-446, HT-29, and U937 cell lines. Only compound 8 displayed a weak activity with IC₅₀ values of 36 and 50 µM against Hela and HT-29 cell lines, respectively.

Key words

Astragalus angustifolius - Leguminosae - cycloartane saponins - oleanane saponins

References

• 1 Podlech D. Phylogeny and progression of characters in Old World Astragali (Leguminosae). In: Zhang A, Wu S, editors Floristic characteristics and diversity of East Asian plants. Beijing, China: China Higher Education Press; 1998: 405-407
• 2 Davis P H. Flora of Turkey and the East Aegean Islands. Volume 3 Edinburgh: Edinburgh University Press; 1970: 49-254
• 3 Bedir E, Calış I, Aquino R, Piacente S, Pizza C. Cycloartane triterpene glycosides from the roots of Astragalus brachypterus and Astragalus microcephalus.  J Nat Prod. 1998;  61 1469-1472
• 4 Bedir E, Calış I, Aquino R, Piacente S, Pizza C. Secondary metabolites from the roots of Astragalus trojanus.  J Nat Prod. 1999;  62 563-568
• 5 Bedir E, Calış İ, Aquino R, Piacente S, Pizza C. Trojanoside H: a cycloartane-type glycoside from the aerial parts of Astragalus trojanus.  Phytochemistry. 1999;  51 1017-1020
• 6 Bedir E, Çalış I, Dunbar C, Shara R, Buolamwini J K, Khan I A. Two novel cycloartane-type triterpene glycosides from the roots of Astragalus prusianus.  Tetrahedron. 2001;  57 5961-5966
• 7 Calış İ, Yuruker A, Taşdemir D, Wrigh A D, Sticher O, Luo Y D, Pezzuto J M. Cycloartane triterpene glycosides from the roots of Astragalus melanophrurius.  Planta Med. 1997;  63 183-186
• 8 Gulcemal D, Alankuş-Calışkan O, Perrone A, Ozgokçe F, Piacente S, Bedir E. Cycloartane glycosides from Astragalus aureus.  Phytochemistry. 2011;  72 761-768
• 9 Yalcin F N, Placente S, Perrone A, Capasso A, Duman H, Calis I. Cycloartane glycosides from Astragalus stereocalyx.  Phytochemistry. 2012;  73 119-126
• 10 Horo I, Bedir E, Perrone A, Ozgokçe F, Piacente S, Alankuş-Calışkan O. Triterpene glycosides from Astragalus icmadophilus.  Phytochemistry. 2010;  71 956-973
• 11 Polat E, Bedir E, Perrone A, Piacente S, Alankus-Calıskan O. Triterpenoid saponins from Astragalus wiedemannianus Fischer.  Phytochemistry. 2010;  71 658-662
• 12 Bedir E, Pugh N, Calış I, Pasco D S, Khan I A. Immunostimulatory effects of cycloartane-type triterpene glycosides from Astragalus species.  Biol Pharm Bull. 2000;  23 834-837
• 13 Ozipek M, Dönmez A A, Calış I, Brun R, Ruedi P, Taşdemir D. Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius.  Phytochemistry. 2005;  66 1168-1173
• 14 Gariboldi P, Pelizzoni F, Tatò M, Verotta L, El-Sebakhy N A, Asaad A M, Abdallah R M, Toaima S M. Cycloartane triterpene glycosides from Astragalus trigonus.  Phytochemistry. 1995;  40 1755-1760
• 15 Radwan M M, El-Sebakhy N A, Asaad A M, Toaima S M, Kingston D G I. Kahiricosides II–V cycloartane glycosides from an Egyptian collection of Astragalus kahiricus.  Phytochemistry. 2004;  65 2909-2913
• 16 Khushbaktova Z A, Agzamova M A, Syrov V N, Radchenko N V, Mirsalikhova N M, Umarova F T. Influence of cycloartanes from plants of the genus Astragalus and their synthetic analogs on the contractive function of the myocardium and the activity of Na,K-ATPase.  Chem Nat Compd. 1994;  30 469-473
• 17 Sevimli-Gur C, Onbaşılar İ, Atilla P, Genç R, Cakar N, Deliloğlu-Gurhan I, Bedir E. In vitro growth stimulatory and in vivo wound healing studies on cycloartane-type saponins of Astragalus genus.  J Ethnopharmacol. 2011;  134 844-850
• 18 Nalbantsoy A, Nesil T, Erden S, Calış I, Bedir E. Adjuvant effects of Astragalus saponins macrophyllosaponin B and astragaloside VII.  J Ethnopharmacol. 2011;  134 897-903
• 19 Kikuchi T, Akihisa T, Tokuda H, Ukiya M, Watanabe K, Nishino H. Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models.  J Nat Prod. 2007;  70 918-922
• 20 De Marino S, Borbone N, Iorizzi M, Esposito G, McClintock J B, Zollo F. Bioactive asterosaponins from the starfish Luidia quinaria and Psilaster cassiope. Isolation and structure characterization by two-dimensional NMR spectroscopy.  J Nat Prod. 2003;  66 515-519
• 21 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
• 22 Kitagawa I, Wang H K, Saito M, Takagi A, Yoshikawa M. Saponin and sapogenol. XXXV. Chemical constituents of Astragali radix, the root of Astragalus membranaceus Bunge. (2). Astragalosides I, II and IV, Acetylastragaloside I and isoastragalosides I and II.  Chem Pharm Bull. 1983;  31 698-708
• 23 Calış I, Donmez A A, Perrone A, Pizza C, Piacente S. Cycloartane saponins from Astragalus campylosema Boiss. ssp. campylosema.  Phytochemistry. 2008;  69 2634-2638
• 24 Mamedova R P, Isaev M I. Triterpenoids from Astragalus plants.  Chem Nat Compd. 2004;  40 303-357
• 25 De Tommasi N, Piacente S, Gacs-Baitz E, De Simone F, Pizza C, Aquino R. Triterpenoid saponins from Spergularia ramosa.  J Nat Prod. 1998;  61 323-327
• 26 Kapusta I, Stochmal A, Perrone A, Piacente S, Pizza C, Oleszek W. Triterpene saponins from Barrel Medic (Medicago truncatula) aerial parts.  J Agric Food Chem. 2005;  63 2164-2170
• 27 Kinjo J, Miyamoto I, Murakami K, Kida K, Tomimatsu T, Yamasaki M, Nohara T. Oleanene-sapogenols from puerariae radix.  Chem Pharm Bull. 1985;  33 1293-1296
• 28 Kitagawa I, Wang H K, Saito M, Yoshikawa M. Saponin and sapogenol. XXXIII. Chemical constituents of the seeds of Vigna angularis (WILLD.) OHWI et OHASHI. (3). Azukisaponins V and VI.  Chem Pharm Bull. 1983;  31 683-688
• 29 Kitagawa I, Wang H K, Yoshikawa M. Saponin and sapogenol. XXXVII. Chemical constituents of Astragali radix, the root of Astragalus membranaceus Bunge. (4). Astragalosides VII and VIII.  Chem Pharm Bull. 1983;  31 716-722
• 30 Miyao H, Sakai Y, Takashita T, Kinjo J, Nohara T. Triterpene saponins from Abrus cantoniensis (Leguminosae). I. Isolation and characterization of four new saponins and a new sapogenol.  Chem Pharm Bull. 1996;  44 1222-1227
• 31 Isaev M I. Triterpene glycosides of Astragalus and their genins XXXIX. Cycloaraloside D from Astragalus amarus.  Chem Nat Compd. 1991;  4 526-528
• 32 Tian Z, Yang M, Huang F, Li K, Si J, Shi L, Chen S, Xiao P. Cytotoxicity of three cycloartane triterpenoids from Cimicifuga dahurica.  Cancer Lett. 2005;  226 65-75