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

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.

Key words

steroidal saponin - Dioscorea bulbifera L. - Dioscoreaceae - cytotoxicity

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