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DOI: 10.1055/s-0030-1250672
© Georg Thieme Verlag KG Stuttgart · New York
Cytotoxic Steroidal Saponins from Agave sisalana
Publikationsverlauf
                     received	June 6, 2010
                     
                     revised	Nov. 15, 2010
                     
                     accepted	Dec. 7, 2010
                     
Publikationsdatum:
17. Januar 2011 (online)

Abstract
Two new steroidal saponins, 8 and 10, along with 7 known steroidal sapogenins and saponins (1–7) and a furostanol saponin (9) were isolated from Agave sisalana Perrine ex Engelm. The structures of these two new compounds were identified and characterized by 1D and 2D NMR spectroscopy and mass spectrometry. In addition, acid hydrolysis and GC‐FID were used to confirm the sugar moieties of 8 and 10. The cytotoxic effects of 1–10 on MCF-7, NCI-H460, and SF-268 cancer cells were evaluated, and among them, compound 10 proved to be the most cytotoxic with IC50 values of 1.2, 3.8, and 1.5 µM, respectively.
Key words
Agavaceae - Agave sisalana - steroidal saponin - MCF‐7 cells - NCI‐H460 cells - SF‐268 cells
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References
- 1 Sparg S G, Light M E, Van Staden J. Biological activities and distribution of plant saponins. J Ethnopharmacol. 2004; 94 219-243
- 2 Hostettmann K, Marston A. Saponins, Appendix 3. Cambridge; Cambridge University Press 1995 
            Reference Ris Wihthout Link
- 3 Yang C R, Zhang Y, Jacob M R, Khan S I, Zhang Y J, Li X C. Antifungal activity of C-27 steroidal saponins. Antimicrob Agents Chemother. 2006; 50 1710-1714
- 4 Jin J M, Zhang Y J, Yang C R. Four new steroid constituents from the waste residue of fibre separation from Agave americana leaves. Chem Pharm Bull. 2004; 52 654-658
- 5 Chen P Y, Kuo Y C, Chen C H, Kuo Y H, Lee C K. Isolation and immunomodulatory effect of homoisoflavones and flavones from Agave sisalana Perrine ex Engelm. Molecules. 2009; 14 1789-1795
- 6 Zou P, Fu J, Yu H S, Zhang J, Kang L P, Ma B P, Yan X Z. The NMR studies on two new furostanol saponins from Agave sisalana leaves. Magn Reson Chem. 2006; 44 1090-1095
- 7 Mimaki Y, Kanmoto T, Kuroda M, Sashida Y, Nishino A, Satomi Y, Nishino H. Steroidal saponins from the underground parts of Hosta longipes and their inhibitory activity on tumor promoter-induced phospholipid metabolism. Chem Pharm Bull. 1995; 43 1190-1196
- 8 Yokosuka A, Mimaki Y. Steroidal glycosides from the underground parts of Trillium erectum and their cytotoxic activity. Phytochemistry. 2008; 69 2724-2730
- 9 Ito A, Chai H B, Kardono L B S, Setowati F M, Afriastini J J, Riswan S, Farnsworth N R, Cordell G A, Pezzuto J M, Swanson S M, Kinghorn A D. Saponins from the bark of Nephelium maingayi. J Nat Prod. 2004; 67 201-205
- 10 Finlay G J, Baguley B C, Wilson W R. A semiautomated microculture method for investigating growth inhibitory effects of cytotoxic compounds on exponentially growing carcinoma cells. Anal Biochem. 1984; 139 272-277
- 11 Tori K, Seo S, Terui Y, Nishikawa J, Yasuda F. Carbon-13 NMR spectra of 5β-steroidal saponins. Reassignment of the F-ring carbon signals of (25S)-spirostans. Tetrahedron Lett. 1981; 22 2405-2408
- 12 Wu T S, Shi L S, Kuo S C. Alkaloids and other constituents from Tribulus terrestris. Phytochemistry. 1999; 50 1411-1415
- 13 Jaffer A J, Crabb T A, Turner C H. Hydroxy group substituent effects on 1H NMR chemical shifts in the structural elucidation of spirostanes. Org Magn Reson. 1983; 21 576-579
- 14 Nakano K, Hara Y, Murakami K, Takaishi Y, Tomimatsu T. 12-Hydroxy steroidal glycosides from the caudex of Yucca gloriosa. Phytochemistry. 1991; 30 1993-1995
- 15 Sati O P, Pant G. Cantalasaponin-1, a novel spirostanol bisdesmoside from Agave cantala. J Nat Prod. 1985; 48 395-399
- 16 Jin J M, Zhang Y J, Yang C R. Spirostanol and furostanol glycosides from the fresh tubers of Polianthes tuberose. J Nat Prod. 2004; 67 5-9
- 17 Ding Y, Tian R H, Yang C R, Chen Y Y, Nohara T. Two new steroidal saponins from dried fermented residues of leaf-juices of Agave sisalana forma Dong No. 1. Chem Pharm Bull. 1993; 41 557-560
- 18 Agrawal P K. Spectral assignments and reference data. Magn Reson Chem. 2003; 41 965-968
Prof. Ching-Kuo Lee
         School of Pharmacy, Taipei Medical University
         
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Prof. Yueh-Hsiung Kuo
         Tsutzki Institute for Traditional Medicine
China Medical University
         
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