Nine glycosides of spirostan (1–7) and furostan (8 and 9) type steroids including a new compound, 7-oxodioscin (1), were isolated from the rhizomes of Dioscorea nipponica. The structure of 1 was established as (25R)-3β-O-[(α-L-rhamnopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl)oxy]spirost-5-en-7-one by extensive spectroscopic techniques including HRESI-TOFMS, 1D and 2D NMR, and chemical methods. Known compounds were elucidated as dioseptemloside G (2), (25R)-dracaenoside G (3), orbiculatoside B (4), dioscin (5), progenin III (6), gracillin (7), (3β,22α,25R)–26-(β-D-glucopyranosyloxy)-22-methoxyfurost-5-en-3-yl O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside (8), and methylprotodioscin (9).
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2.
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3.
ChienM-H, YingT-H, HsiehY-S, ChangY-C, YehC-M, KoJ-L, LeeW-S, ChangJ-H, YangS-F. (2012) Dioscorea nipponica Makino inhibits migration and invasion of human oral cancer HSC-3 cells by transcriptional inhibition of matrix metalloproteinase-2 through modulation of CREB and AP-1 activity. Food and Chemical Toxicology, 50, 558–566.
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6.
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7.
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8.
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9.
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10.
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11.
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12.
ZhangL-J, YuH-S, KangL-P, FengB., QuanB., SongX-B, MaB-P, KangT-G. (2012) Two new steroidal saponins from the biotransformation product of the rhizomes of Dioscorea nipponica.Journal of Asian Natural Products Research, 14, 640–646.
13.
WangY-H, AvulaB., FuX., WangM., KhanI.A. (2012) Simultaneous determination of the absolute configuration of twelve monosaccharide enantiomers from natural products in a single injection by a UPLC-UV/MS method. Planta Medica, 78, 834–837.
14.
LiuX-T, WangZ-Z, XiaoW., ZhaoH-W, HuJ., YuB. (2008) Cholestane and spirostane glycosides from the rhizomes of Dioscorea septemloba.Phytochemistry, 69, 1411–1418.
15.
ZhengQ-A, ZhangY-J, LiH-Z, YangC-R. (2004) Steroidal saponins from fresh stem of Dracaena cochinchinensis.Steroids, 69, 111–119.
16.
ShenP., WangS.L., LiuX.K., YangC.R., CaiB., YaoX.S. (2002) A new steroidal saponin from Dioscorea deltoidea Wall var. orbiculata. Chinese Chemical Letters, 13, 851–854.
17.
HuK., DongA., YaoX., KobayashiH., IwasakiS. (1996) Antineoplastic agents; I. Three spirostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca. Planta Medica, 62, 573–575.
18.
HayesP.Y., LambertL.K., LehmannR., PenmanK., KitchingW., DeV.J.J. (2007) Spectral assignments and reference data complete 1H and 13C assignments of the four major saponins from Dioscorea villosa (wild yam). Magnetic Resonance in Chemistry, 45, 1001–1005.
19.
ZouC-C, HouS-J, ShiY., LeiP-S, LiangX-T. (2003) The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides. Carbohydrate Research, 338, 721–727.
20.
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21.
BahM., GutierrezD.M., EscobedoC., MendozaS., IselaR.J., RojasA. (2004) Methylprotodioscin from the Mexican medical plant Solanum rostratum (Solanaceae). Biochemical Systematics and Ecology, 32, 197–202.
