Planta Med 2011; 77(8): 845-848
DOI: 10.1055/s-0030-1250633
Biological and Pharmacological Activity
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Steroidal Saponins from the Rhizomes of Dioscorea bulbifera and Their Cytotoxic Activity

Hai Liu1 , 2 , Gui-Xin Chou1 , 2 , Jun-Ming Wang1 , Li-Li Ji1 , 2 , Zheng-Tao Wang1 , 2
  • 1The MOE Key Laboratory for Standardization of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai, P. R. China
  • 2Shanghai R & D Centre for Standardization of Chinese Medicines, Shanghai, P. R. China
Weitere Informationen

Publikationsverlauf

received July 4, 2010 revised November 21, 2010

accepted November 24, 2010

Publikationsdatum:
16. Dezember 2010 (online)

Abstract

Two new steroidal saponins, diosbulbisides D (1) and E (2), along with five known saponins (37) were isolated from the rhizomes of Dioscorea bulbifera L. Their structures were elucidated on the basis of spectral data. Compounds 6 and 7, two 3-O-trisaccharides of diosgenin spirostanes, showed moderate cytotoxic activity against human hepatocellular carcinoma cells, with IC50 values of 3.89 µM and 7.47 µM on SMMC7721, and 10.87 µM and 19.10 µM on Bel-7402 cell lines, respectively.

References

  • 1 Gao H Y, Kuroyanagi M, Wu L, Kawahara N, Yasuno T, Nakamura Y. Antitumor-promoting constituents from Dioscorea bulbifera L. in JB6 mouse epidermal cells.  Biol Pharm Bull. 2002;  25 1241-1243
  • 2 Murray R D H, Jorge Z D, Khan N H, Shahjahan M, Quaisuddin M. Diosbulbin D and 8-epidiosbulbin-E acetate, norclerodane diterpenoid from Dioscorea bulbifera tubers.  Phytochemistry. 1984;  23 623-625
  • 3 Komori T. Glycosides from Dioscorea bulbifera.  Toxicon. 1997;  35 1531-1535
  • 4 Teponno R B, Tapondjou A L, Abou-Mansour E, Stoeckli-Evans H, Tane P, Barboni L. Bafoudiosbulbins F and G, further clerodane diterpenoids from Dioscorea bulbifera L. var sativa and revised structure of bafoudiosbulbin B.  Phytochemistry. 2008;  69 2374-2379
  • 5 Teponno R B, Tapondjou A L, Gatsing D, Djoukeng J D, Abou-Mansour E, Tabacchi R, Tane P, Stoekli-Evans H, Lontsi D. Bafoudiosbulbins A, and B, two anti-salmonellal clerodane diterpenoids from Dioscorea bulbifera L. var sativa.  Phytochemistry. 2006;  67 1957-1963
  • 6 Zheng S Z, Guo Z, Shen T, Zhen X D, Shen X W. Three new apianen lactones from Dioscorea bulbifera L.  Indian J Chem Sect B. 2003;  42 946-949
  • 7 Teponno R B, Tapondjou A L, Ju-Jung H, Nam J H, Tane P, Park H J. Three new clerodane diterpenoids from the bulbils of Dioscorea bulbifera L. var sativa.  Helv Chim Acta. 2007;  90 1599-1605
  • 8 Wang G, Liu J S, Lin B B, Wang G K, Liu J K. Two new furanoid norditerpenes from Dioscorea bulbifera.  Chem Pharm Bull. 2009;  57 625-627
  • 9 Liu H, Chou G X, Guo Y L, Ji L L, Wang J M, Wang Z T. Norclerodane diterpenoids from the rhizomes of Dioscorea bulbifera.  Phytochemistry. 2010;  71 1174-1180
  • 10 Liu H, Chou G X, Wu T, Guo Y L, Wang S C, Wang C H, Wang Z T. Steroidal sapogenins and glycosides from the rhizomes of Dioscorea bulbifera.  J Nat Prod. 2009;  72 1964-1968
  • 11 Teponno R B, Tapondjou A L, Djoukeng J D, Abou-Mansour E, Tabacchi R, Tane P, Lontsi D, Park H J. Isolation and NMR assignment of a pennogenin glycoside from Dioscorea bulbifera L. var sativa.  Nat Prod Sci. 2006;  12 62-66
  • 12 Li S S, Deng J Z, Zhao S X. Steroids from tuber of Dioscorea bulbifera L.  J Plant Resour Environ. 1999;  8 61-62
  • 13 Sautour M, Mitaine-Offer A C, Lacaille-Dubois M A. The Dioscorea genus: a review of bioactive steroid saponins.  J Nat Med. 2007;  61 91-101
  • 14 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 2479-2496
  • 15 Mahato S B, Sahu N P, Ganguly A N. Steroidal saponins from Dioscorea floribunda: Structures of floribundasaponins A and B.  Phytochemistry. 1981;  20 1943-1946
  • 16 Han X W, Yu H, Liu X M, Bao X, Yu B, Li C, Hui Y Z. Complete 1H and 13C NMR assignments of diosgenyl saponins.  Magn Reson Chem. 1999;  37 140-144
  • 17 Agrawal P K. Assigning stereodiversity of the 27-Me group of furostane-type steroidal saponins via NMR chemical shifts.  Steroids. 2005;  70 715-724
  • 18 Mimaki Y, Watanabe K, Sakagami H, Sashida Y. Steroidal glycosides form the leaves of Cestrum nocturnum.  J Nat Prod. 2002;  65 1863-1868
  • 19 Kasai R, Okihara M, Asakawa J, Mizutani K, Tanaka O. 13C nmr study of α-anomeric and β-anomeric pairs of d-mannopyranosides and l-rhamnopyranosides.  Tetrahedron. 1979;  35 1427-1432
  • 20 Carmichael J, Degraff W G, Gazdar A F, Minna J D, Mitchell J B. Evaluation of a tetrazolium based semiautomated colorimetric assay assessment of chemosensitivity testing.  Cancer Res. 1987;  47 936-942

Prof. Dr. Zheng-Tao Wang

The MOE Key Laboratory for Standardization of Chinese Medicines
Institute of Traditional Chinese Medicine
Shanghai University of Traditional Chinese Medicine

1200 Cailun Road

201210 Shanghai

P. R. China

Telefon: +86 21 51 32 25 07

Fax: +86 21 51 32 25 19

eMail: wangzht@hotmail.com