Planta Med 2004; 70(6): 556-560
DOI: 10.1055/s-2004-827157
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Steroidal Saponins from Myriopteron extensum and Their Cytotoxic Activity

Ming-Fu Yang1 , 2 , Yu-Yuan Li1 , Xiao-Ping Gao3 , Bo-Gang Li1 , 3 , Guo-Lin Zhang1
  • 1Chengdu Institute of Biology, the Chinese Academy of Sciences, Chengdu, P. R. China
  • 2Chengdu Institute of Organic Chemistry, the Chinese Academy of Sciences, Chengdu, P. R. China
  • 3Pharmaceutical Institute of Di-Ao Pharmaceutical Group, Chengdu, P. R. China
Further Information

Publication History

Received: November 13, 2003

Accepted: March 7, 2004

Publication Date:
01 July 2004 (online)

Abstract

Two new steroidal saponins, extensumsides A (1) and B (2), were isolated from the whole plants of Myriopteron extensum (Wight) K. Schum. Their structures were elucidated as 17β-uzarigenin-3-O-β-glucopyranosyl-(1→6)-β-glucopyranosyl-(1→4)-β-thevetopyranosyl-(1→4)-β-cymaropyranoside (1) and 12-(3-methylbut-2-enoyloxy)pregn-5-en-20-one 3-O-[β-cymaropyranosyl-(1→4)-β-cymaropyranosyl-(1→4)-β-thevetopyranosyl-(1→4)-(6-O-sulfo-β-glucopyranoside)] (2) on the basis of chemical and spectral evidence. Extensumside A exhibited significant cytotoxicity against eight cancer cell lines with a mean GI50 value of 0.346 μg/mL.

References

  • 1 Delectis Florae Reipublicae Popularis Agendae Academiae Sinicae E dita. Flora Reipublicae Popularis Sinicae. Vol 63 Beijing; Science Press 1977: pp 270-2
  • 2 Ran X D. Zhongyao Yaohai (Dictionary of Traditional Chinese Medicine). Vol 2 Harbin; Harbin Press 1993: p 1437
  • 3 Sevillano L G, Melero C P, Caballero E, Tomé F, Lelièvre L G, Geering K. et al . Inotropic activity of hydroindene amidinohydrazones.  J Med Chem. 2002;  45 127-36
  • 4 Florkiewicz R Z, Anchin J, Baird A. The inhibition of fibroblast growth factor-2 export by cardenolides implies a novel function for the catalytic subunit of Na+,K+-ATPase.  J Biol Chem. 1998;  273 544-51
  • 5 Skehan P, Storing R, Scudiero D, Monk A, McMahon J, Visica D. et al . New colorimetric cytotoxity assay for anticancer-drug-screen.  J Natl Cancer Inst. 1990;  82 1107-12
  • 6 Rubinstein L V, Shoemaker R H, Paul K D, Tosini S, Skehan P, Scudiero D A. et al . Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines.  J Natl Cancer Inst. 1990;  82 1113-8
  • 7 Chen J J, Zhang Z X, Zhou J, Li B T. New pregnane glycosides from Sinomarsdenia incisa .  J Nat Prod. 1999;  62 829-32
  • 8 Hesham E A, Josef H, Sayed H, Elsayada E K. Cardenolide glycosides with doubly linked sugars from Gomphocarpus sinaicus .  Phytochemistry. 1993;  34 1399-402
  • 9 Maier M S, Roccatagliata A J, Kuriss A, Chludil H, Seldes A M, Pujol C A. et al . Two new cytotoxic and virucidal trisulfated triterpene glycosides from the Antarctic sea cucumber Staurocucumis liouvillei .  J Nat Prod. 2001;  64 732-6
  • 10 Abbott A J, Holoubek C G, Martin R A. Inhibition of Na+,K+-ATPase by the cardenolide 6′-O-(E-4-hydroxycinnamoyl)desglucouzarin.  Biochem Biophys Res Commun. 1998;  251 256-9
  • 11 Choiu F CK, Watson T R. Conformational factors in cardiac glycoside activity.  J Med Chem. 1985;  28 509-15
  • 12 Chen K K. Newer cardiac glycosides and aglycones.  J Med Chem. 1970;  13 1029-34
  • 13 Koike K, Bevelle C, Talapatra S K, Cordell G A, Farnsworth N R. Potential anticancer agents. V. Cardiac glycosides of Asclepias albicans (Asclepiadaceae).  Chem Pharm Bull. 1980;  28 401-5
  • 14 Hyun J W, Shin J E, Lim K H, Sung M S, Park J W, Yu J H. et al . Evomonoside: the cytotoxic cardiac glycoside from Lepidium apetalum .  Planta Med. 1995;  61 294-5

Prof. Dr. Guo-Lin Zhang

Chengdu Institute of Biology

The Chinese Academy of Sciences

P. O. Box 416

Chengdu 610041

P. R. China

Phone: +86-28-8522-5401

Fax: +86-28-8522-5401

Email: zhanggl@cib.ac.cn

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