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

 

 Buy Article Permissions and Reprints

Abstract

Two new steroidal saponins, diosbulbisides D (1) and E (2), along with five known saponins (3–7) 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 3 Komori T. Glycosides from Dioscorea bulbifera.  Toxicon. 1997;  35 1531-1535
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 18 Mimaki Y, Watanabe K, Sakagami H, Sashida Y. Steroidal glycosides form the leaves of Cestrum nocturnum.  J Nat Prod. 2002;  65 1863-1868
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar

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

Phone: +86 21 51 32 25 07

Fax: +86 21 51 32 25 19

Email: wangzht@hotmail.com

• Supplementary Material