Two New Steroidal Saponins from the Rhizomes of Dioscorea panthaica and their Cytotoxic Activity

Abstract

Two new steroidal saponins, dioscoresides C (1) and D (2), along with a new natural product, pregnadienolone 3-O-β-gracillimatriose (3), and two known compounds, pregnadienolone 3-O-β-chacotrioside (4) and pseudoprotodioscin (5), were isolated from the rhizomes of Dioscorea panthaica Prain et Burkill. On the basis of extensive NMR studies and chemical evidence, dioscoresides C and D were determined to be 26-O-β-D-glucopyranosyl-3β,26-dihydroxy-23(S)-methoxy-25(R)-furosta-5,20(22)-dien-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside and 26-O-β-D-glucopyranosyl-3β,26-dihydroxy-20,22-seco-25(R)-furosta-5-en-20,22-dine-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→ 4)]-β-D-glucopyranoside. These compounds showed mild cytotoxicity against the cancer cell lines, A375, L929, and HeLa, in a dose-dependent manner.

Dioscorea panthaica - Dioscoreaceae - steroidal saponins - dioscoreside C - dioscoreside D - cytotoxic activity

References

• 1 Jiangsu New Medical College. Chinese Materia Medica Dictionary. Shanghai Press of Science and Technology 1977: 729-30
• 2 Li B G, Tang Y F, Shi Y. Isolation and identification of steroidal saponins from Dioscorea panthaica Prain et Burkill.  Zhiwu Xuebao. 1986;  28 409-14
• 3 Dong M, Wu L J, Wang B X. Studies on chemical constituents of Yam panthaica (Dioscorea panthaica).  Zhong Cao Yao. 2000;  31 732-3
• 4 Hu K, Dong A J, Yao X S, Kobayashi H, Iwasaki S. Antineoplastic agents; I. Three spirostanol glycosides from rhizomes of Dioscorea colletti var. hypoglauca .  Planta Medica. 1996;  62 573-5
• 5 Hu K, Dong A J, Yao X S, Kobayashi H, Iwasaki S. Antineoplastic agents; II. Four furostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca .  Planta Medica. 1997;  63 161-5
• 6 Ahn B Z, Yoon Y D, Lee Y H, Kim H B, Sok D E. Inhibitory effect of bupleuri radix saponins on adhesion of some solid tumor cells and relation to nemolytic action: screening of 232 herbal drugs for anti-cell adhesion.  Planta Medica. 1998;  64 220-4
• 7 Araghiniknam M, Chung S, Nelson-White T, Eskelson C, Watson R R. Antioxidant activity of dioscorea and dehydroepiandrosterone (DHEA) in older humans.  Life Sciences. 1996;  59 PL 147-57
• 8 Miyahara K, Ida Y, Kawasaki T. Conversion of steroid saponins to the corresponding pregnane glycosides.  Chemical and Pharmaceutical Bulletin. 1972;  20 2506-10
• 9 Nakano K, Murakami K, Takashi Y, Tomimatsu T, Nohara T. Studies on the constituents of Heloniopsis orientalis (Thunb.) C. Tanaka.  Chemical and Pharmaceutical Bulletin. 1989;  37 116-8
• 10 Liang Z Z, Aquino R, Simone F D, Dini A, Schettino O, Pizza C. Oligofuranostanosides from Asparagus cochinchinensis .  Planta Medica. 1988;  54 344-6
• 11 Zhao P P, Li B M, He L Y. Studies on the method of determination of combined sugars in glycosides.  Acta Pharmaceutica Sinica. 1987;  22 70-4
• 12 Kamerling J P, Gerwig G J, Vliegenthart J FG. Characterization by gas-liquid chromatography-mass spectrometry and proton-magnetic-resonance spectroscopy of pertrimethylsilyl methyl glycosides obtained in the methanolysis of glycoproteins and glycopeptides.  The Biochemical Journal. 1975;  151 491-5
• 13 Gerwig G J, Kamerling J P, Vliegerothart J FG. Determination of the D and L configuration of neutral monosaccharides by high-resolution capillary GLC.  Carbohydrate Research. 1978;  62 349-57
• 14 Dong M, Feng X Z, Wang B X, Wu L J, Ikejima T. Two novel furostanol saponins from the rhizomes of Dioscorea panthaica Prain et Burkill and their cytotoxic activity.  Tetrahedron. 2001;  57 501-6
• 15 Sang S M, Lao A, Wang H C, Chen I L. Furostanol saponins from Allicum tuberosum .  Phytochemistry. 1999;  52 1611-5