Three New Cycloartane Triterpenoids from Astragalus bicuspis

Saleem Jan; Ahmed Abbaskhan; Syed Ghulam Musharraf; Samina A. Sattar; Samreen; Saud I. Resayes; Zeid A. Al-Othman; Abdullah M. Al-Majid; Atta-ur-Rahman; M. Iqbal Choudhary

doi:10.1055/s-0030-1271196

Planta Medica, Table of Contents

Planta Med 2011; 77(16): 1829-1834
DOI: 10.1055/s-0030-1271196

Natural Product Chemistry

Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Three New Cycloartane Triterpenoids from Astragalus bicuspis

Saleem Jan¹ ^, ³ , Ahmed Abbaskhan¹ , Syed Ghulam Musharraf¹ , Samina A. Sattar¹ , Samreen¹ , Saud I. Resayes² , Zeid A. Al-Othman² , Abdullah M. Al-Majid² , Atta-ur-Rahman¹ , M. Iqbal Choudhary¹ ^, ²

¹H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan
²Department of Chemistry, King Saud University, Riyadh, Saudi Arabia
³Department of Chemistry, University of Science and Technology, Bannu, Pakistan

Abstract

Three new cycloartane triterpenoids have been isolated from Astragalus bicuspis Fisch. Their structures were elucidated as 23(R),24(S),25(R),26(S)-16β/23,23/26,24/25-triepoxy-26-hydroxy-9,19-cyclolanosta-3,6-dione (1), 6α,23,24,25-tetraol-16β-acetoxy-23(R),24(R)-9,19-cyclanosta-3-one (2), and 6α,23,24,25-tetraol-16β-acetoxy-23(R),24(R)-9,19-cyclolanosta-3β-O-xyloside (3), based on their spectroscopic analysis. All cycloartane tritepenoids exhibited weak cytotoxicities against 3T3 fibroblast cells as compared to the standard drug cycloheximide. Compounds 3 and 4 were also tested for their antileishmanial potential, and a weak activity was observed against promastigotes of Leishmania major.

Key words

Astragalus bicuspis - Leguminosae - cycloartane triterpenoids - antileishmanial activity - cytotoxicity - 3T3 fibroblast cell line

Full Text

References

1 Subarnas A, Oshima Y, Hikino H. Isoflavans and pterocarpans from Astragalus mongholicus. Phytochemistry. 1991; 30 2777-2780
2 Calis I, Zor M, Saracoglu I, Isimer A, Ruegger H. Four novel cycloartane glycosides from Astragalus oleifolius. J Nat Prod. 1996; 59 1019-1023
3 Bedir E, Calis I, Zerbe O, Sticher O. Cyclocephaloside I: a novel cycloartane-type glycoside from Astragalus microcephalus. J Nat Prod. 1998; 61 503-505
4 He Z, Findlay J A. Constituents of Astragalus membranaceus. J Nat Prod. 1991; 54 810-815
5 Ozipek M, Dönmez A A, Calis I, Brun R, Rüedi P, Tasdemir D. Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius. Phytochemistry. 2005; 66 1168-1173
6 Calis I, Koyunoglu S, Yesilada A, Brun R, Rüedi P, Tasdemir D. Antitrypanosomal cycloartane glycosides from Astragalus baibutensis. Chem Biodivers. 2006; 3 923-929
7 Choudhary M I, Jan S, Abbaskhan A, Musharaf S G, Samreen, Sattar A S, Atta-ur-Rahman. Cycloartane triterpenoids of Astragalus bicuspis. J Nat Prod. 2008; 71 1557-1560
8 Naubeev T K, Uteniyazov K K. Cycloartanes from Astragalus flexus. Chem Nat Compd. 2007; 43 560
9 Mamedova R P, Agzamova M A, Isaev M I. Cycloorbigenin C, a new cycloartane genin. Chem Nat Compd. 2003; 39 470-474
10 Govindachari T R, Krishna-Kumari G N, Suresh G. Triterpenoids from Walsura piscidia. Phytochemistry. 1995; 39 167-170
11 Joycharat N, Greger H, Hofer O, Saifah E. Flavaglines and triterpenoids from the leaves of Aglaia forbesii. Phytochemistry. 2008; 69 206-211
12 Gigoshvili T I, Alaniya M D, Tsitsishvili V G, Foure R, Debrauver L, Kemertelidze E P. Structure of cyclogaleginoside E from Astragalus galegiformis. Chem Nat Compd. 2003; 39 373
13 Mamedova R P, Agzamova M A, Isaev M I. Cycloorbicoside C, a new bisdesmoside. Chem Nat Compd. 2002; 38 570-579
14 Avunduk S, Mitaine-Offer A, Alankus-Caliskan O, Miyamoto T, Senol S G, Lacaille-Dubois M. Triterpene glycosides from the roots of Astragalus flavescence. J Nat Prod. 2008; 71 141-145
15 Ikeda T, Udayama M, Okawa M, Arao T, Kinjo J, Nohara T. Potential hydrolysis of soyasaponin I and hepatoprotective effects of the hydrolytic products. Study of the structure-hepatoprotective relationship of soyasapogenol B analogs. Chem Pharm Bull. 1998; 46 359-361
16 Isuda Y, Sano T, Miyauchi M. Triterpenoid chemistry VII. Classification of triterpenoid 1,3-glycol acetonide by NMR spectra. Chem Pharm Bull. 1974; 22 2396
17 Kang S S, Woo W S. Melilotigenin, a new sapogenin from Melilotus officinalis. J Nat Prod. 1988; 51 335-338
18 Liu C, Wang H, Wei S, Gao K. Oleanane-type triterpenes from the flowers and roots of Saussurea muliensis. J Nat Prod. 2008; 71 789-792
19 Steffens J C, Roark J L, Lynn D G, Riopel J L. Host recognition in parasitic angiosperms: use of correlation spectroscopy to identify long-range coupling in a haustorial inducer. J Am Chem Soc. 1983; 105 1669-1671
20 Habtemariam S. In vitro antileishmanial effects of antibacterial diterpenes from two Ethiopian Premna species: P. schimperi and P. oligotricha. Biomed Central Pharmacol. 2003; 3 6-11
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 Yeskaliyeva B, Mesaik M A, Abbaskhan A, Kulsoom A, Burasheva G S, Abilov Z A, Choudhary M I, Atta-ur-Rahman. Bioactive flavonoids and saponins from Climacoptera obtusifolia. Phytochemistry. 2006; 67 2392-2397

Prof. M. Iqbal Choudhary

H. E. J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi

Karachi 75270

Pakistan

Phone: +92 21 48 24 92 45

Fax: +92 21 48 19 01 89

Email: hej@cyber.net.pk