Dioscoreside C

Planta Med . 2001 Dec;67(9):853-7

Two new steroidal saponins from the rhizomes of Dioscorea panthaica and their cytotoxic activity[Pubmed: 11745024]

Two new steroidal saponins, dioscoresides C (1) and D (2), along with a new natural product, pregnadienolone 3-O-beta-gracillimatriose (3), and two known compounds, pregnadienolone 3-O-beta-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-beta-D-glucopyranosyl-3 beta,26-dihydroxy-23(S)-methoxy-25(R)-furosta-5,20(22)-dien-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside and 26-O-beta-D-glucopyranosyl-3 beta,26-dihydroxy-20,22-seco-25(R)-furosta-5-en-20,22-dine-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1--> 4)]-beta-D-glucopyranoside. These compounds showed mild cytotoxicity against the cancer cell lines, A375, L929, and HeLa, in a dose-dependent manner.

Yao Xue Xue Bao . 2001 Jan;36(1):42-45.

[Isolation and identification of steroidal saponins from Dioscorea panthaica Prain et Burkill][Pubmed: 12579859]

Aim: To investigate the chemical constituents of the rhizomes of Dioscorea panthaica Prain et Burkill and look for new active compounds. Methods: The compounds were isolated with silica gel and HPLC, and their structures were elucidated on the basis of chemical evidences and spectral analysis (IR, ESI-MS, 1HNMR, 13CNMR, DEPT, 1H-1H COSY, HMQC, HMBC, NOESY). Results: Three steroidal saponins were isolated from the rhizomes of Dioscorea panthaica. They were elucidated as 26-O-beta-D-glucopyranosyl-3 beta, 26-diol-23(S)-methoxy-25(R)-delta 5,20(22)-diene-furosta-3-O-[alpha-L-rhamnopyranosyl-(1-->2)- O-alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (I), pseudoprotodioscin (II), 26-O-beta-D-glucopyranosyl-3 beta, 26-diol-25 (R)-delta 5,20(22)-diene-furosta-3-O-alpha-L-rhamnopyranosyl- (1-->2)-O-beta-D-glucopyranoside (III). Conclusion: Compound I is a new steroidal saponin and was named as Dioscoreside C. Compound II and III were obtained from this genus for the first time.

Planta Med . 2001 Dec;67(9):853-857.

Two new steroidal saponins from the rhizomes of Dioscorea panthaica and their cytotoxic activity[Pubmed: 11745024]

Two new steroidal saponins, dioscoresides C (1) and D (2), along with a new natural product, pregnadienolone 3-O-beta-gracillimatriose (3), and two known compounds, pregnadienolone 3-O-beta-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-beta-D-glucopyranosyl-3 beta,26-dihydroxy-23(S)-methoxy-25(R)-furosta-5,20(22)-dien-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside and 26-O-beta-D-glucopyranosyl-3 beta,26-dihydroxy-20,22-seco-25(R)-furosta-5-en-20,22-dine-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1--> 4)]-beta-D-glucopyranoside. These compounds showed mild cytotoxicity against the cancer cell lines, A375, L929, and HeLa, in a dose-dependent manner.