Planta Med 2006; 72(7): 667-670
DOI: 10.1055/s-2006-931582
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Bioactive Steroidal Saponins from Smilax medica

M. Sautour1 , T. Miyamoto2 , M.-A. Lacaille-Dubois1
  • 1Laboratoire de Pharmacognosie, Unité de Molécules d’Intérêt Biologique, UMIB, UPRES-EA 3660, Faculté de Pharmacie, Université de Bourgogne, Dijon, France
  • 2Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
Weitere Informationen

Publikationsverlauf

Received: December 16, 2005

Accepted: February 14, 2006

Publikationsdatum:
29. Mai 2006 (online)

Abstract

Two new spirostanol saponins (1 and 2) were isolated from the roots of Smilax medica, together with the known smilagenin 3-O-β-D-glucopyranoside (3). Their structures were determined by spectroscopic methods including 1D- and 2D-NMR experiments. Compounds 1 and 2 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs between 6.25 and 50 μg/mL) whereas 3 was inactive.

References

  • 1 Tschesche R, Lüdke G, Wulff G. Steroid saponins with more than 1 sugar chain. Sarsaparilloside, a bisdesmosidic 22-hydroxy-furanostanol saponin.  Chem Ber. 1969;  102 1253-69
  • 2 Ju Y, Jia Z H. Steroidal saponins from Smilax lebrunii .  Phytochemistry. 1992;  31 1349-51
  • 3 Sashida Y, Kubo S, Mimaki Y, Nikaido T, Ohmoto T. Steroidal saponins from Smilax riparia and S. china .  Phytochemistry. 1992;  31 2439-43
  • 4 Kubo S, Mimaki Y, Sashida Y, Nikaido T, Ohmoto T. Steroidal saponins from the rhizomes of Smilax sieboldii .  Phytochemistry. 1992;  31 2445-50
  • 5 Bernardo R R, Pinto A V, Parente J P. Steroidal saponins from Smilax officinalis .  Phytochemistry. 1996;  43 465-9
  • 6 Sautour M, Miyamoto T, Lacaille-Dubois M A. Three new steroidal saponins from Smilax medica and their antifungal activity.  J Nat Prod. 2005;  68 1489-93
  • 7 Agrawal P K, Jain D C, Gupta R K, Thakur R S. Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins.  Phytochemistry. 1985;  24 2479-96
  • 8 Agrawal P K. 25R/25S Stereochemistry of spirostane-type steroidal saponins via chemical shift of geminal protons of ring-F.  Magn Reson Chem. 2003;  41 965-8
  • 9 Debella A, Haslinger E, Kunert O, Michl G, Abebe D. Steroidal saponins from Asparagus africanus .  Phytochemistry. 1999;  51 1069-75
  • 10 Wawer I, Nartowska J, Cichowlas A A. 13C cross-polarisation MAS NMR study of some steroidal sapogenins.  Solid State Nucl Magn Reson. 2001;  20 35-45
  • 11 Agrawal P K, Bunsawansong P, Morris G A. Dependence of the 1H NMR chemical shifts of ring F resonances on the orientation of the 27-methyl group of spirostane-type steroidal sapogenins.  Phytochemistry. 1998;  47 255-7
  • 12 Tori K, Seo S, Terui Y, Nishikawa J, Yasuda F. Carbon-13 NMR spectra of 5β-steroidal sapogenins. Reassignment of the F-ring carbon signals of (25S)-spirostans.  Tetrahedron Lett. 1981;  22 2405-8
  • 13 Yang Q X, Xu M, Zhang Y J, Li H Z, Yang C R. Steroidal saponins from Disporopsis pernyi .  Helv Chim Acta. 2004;  87 1248-53
  • 14 Agrawal P K, Jain D C, Pathak A K. NMR spectroscopy of steroidal sapogenins and steroidal saponins: an update.  Magn Reson Chem. 1995;  33 923-53
  • 15 Buckingham J B. Dictionary of natural products on CD-ROM, Version 14 : 1. London; Chapman and Hall CRC Press 2005
  • 16 Sautour M, Mitaine-Offer A C, Miyamoto T, Dongmo A, Lacaille-Dubois M A. Antifungal steroid saponins from Dioscorea cayenensis .  Planta Med. 2004;  70 90-2
  • 17 Sautour M, Mitaine-Offer A C, Miyamoto T, Dongmo A, Lacaille-Dubois M A. A new steroidal saponin from Dioscorea cayenensis .  Chem Pharm Bull. 2004;  52 1353-5
  • 18 Takechi M, Shimada S, Tanaka Y. Structure-activity relationships of the saponins dioscin and dioscinin.  Phytochemistry. 1991;  12 3943-4
  • 19 Sautour M, Mitaine-Offer A C, Miyamoto T, Wagner H, Lacaille-Dubois M A. A new phenanthrene glycoside and other constituents from Dioscorea opposita .  Chem Pharm Bull. 2004;  52 1235-7
  • 20 Haddad M, Miyamoto T, Laurens V, Lacaille-Dubois M A. Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia .  J Nat Prod. 2003;  66 372-7
  • 21 Quiroga E N, Sampietro A R, Vattuone M A. Screening antifungal activities of selected medicinal plants.  J Ethnopharmacol. 2001;  74 89-96

Prof. Marie-Aleth Lacaille-Dubois

Laboratoire de Pharmacognosie

Unité UMIB

UPRES-EA 3660

Faculté de Pharmacie

Université de Bourgogne

7 Bd. Jeanne d’Arc

BP 87900

21079 Dijon Cedex

France

Fax: +33-3-80-39-33-00

eMail: malacd@u-bourgogne.fr