Steroidal saponins from the rhizome of Paris polyphylla and their cytotoxic activities.
Two new furostanol saponins and one new spirostanol saponin were isolated from the rhizome of Paris polyphylla Smith var. yunnanensis, together with 18 known steroidal saponins. The structures of the new steroidal saponins were elucidated as 26-O-beta-D-glucopyranosyl-(25R)-5-ene-furost-3 beta, 17 alpha, 22 alpha, 26-tetrol-3-O-alpha-L-arabinofuranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (2, parisyunnanoside A), 26-O-beta-D-glucopyranosyl-(25R)-5, 20 (22)-diene-furost-3 beta, 26-diol-3-O-alpha-L-arabinofuranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (7, parisyunnanoside B), and (25R)-spirost-5-ene-3 beta, 12 alpha-diol-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (13, parisyunnanoside C) by MS and 1 D and 2 D NMR analysis. The isolated compounds were evaluated for their cytotoxicity against HL-60 human promyelocytic leukemia cells. Our results showed that the spirostanol framework of the aglycone and the terminal alpha-L-rhamnopyranosyl with 1-->2 linkage to the sugar chain of saponins at C-3 are essential for their high cytotoxicity, whereas the hydroxy group substitution at C-12 or C-17 of the aglycone causes a reduction in their activity.
Zhao
Yu
Y
Department of Biotechnology, Beijing Institute of Radiation Medicine, Beijing, PR China.
Kang
Li-Ping
LP
Liu
Yi-Xun
YX
Liang
Yu-Gang
YG
Tan
Da-Wei
DW
Yu
Zu-Yin
ZY
Cong
Yu-Wen
YW
Ma
Bai-Ping
BP
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D018922:HL-60 Cells; D006801:Humans; D019668:Liliaceae / Q000737:chemistry*; D015394:Molecular Structure; D027343:Rhizome / Q000737:chemistry; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology*; D013256:Steroids / Q000737:chemistry* / Q000494:pharmacology*
D000972:Antineoplastic Agents, Phytogenic; D012503:Saponins; D013256:Steroids