Isolation and identification of steroidal saponins in total saponin from Dioscorea nipponica Makino

Anhui Institute of Medical Sciences, Hefei 230061, China.
Yao xue xue bao = Acta pharmaceutica Sinica 05/2002; 37(4):267-70.
Source: PubMed


To investigate the water-soluble steroidal saponins in total saponin from Dioscorea nipponica Makino and look for new active compounds.
The compounds were isolated with silica gel, PTLC and HPLC, and their structures were elucidated by acid hydrolysis, physical and chemical data and spectral analysis (IR, NMR, MS, HMQC, HMBC) as well as chemical correlations.
The two steroidal saponins (water-insoluble saponin and water-soluble saponin) were isolated from the total saponin of Dioscorea nipponica Makino. The structures were elucidated as diosgenin 3-O-[alpha-L-rhamnopy ranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]]-beta-D-glucopyranoside (I), diosgenin 3-O-[alpha-L-rhamnopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside (II).
Compound II is a new steroidal saponin and firstly isolated from Dioscorea nipponica Makino. It was named as dioscin Dc.

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    • "D. nipponica Makino is also associated with antiobesity, antiinflammation, and anticancer properties [3]. Previous studies of D. nipponica have reported the presence of steroidal glycosides [2] [4] [5] [6], phenanthrene derivatives [7] [8], water soluble non-saponin components [benzyl 1- O-β-D-glucopyranoside, leonuriside A, icariside D2, pyrocatechol 1-O-β-D-glucopyranoside, (+) syringaresinol-4-O-β-D-glucopyrano- side, cyclo-(leu-tyr), and adenosine [9], and a phenolic acid (piscidic acid) [10]. In the present study, a phytochemical investigation of D. nipponica rhizomes was undertaken to discover new chemical constituents. "
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    • "Previous studies have indicated that Dioscorea nipponica extract (DNE) could reduce the metastasis of melanoma in vitro and in vivo through inhibited phosphorylation of Akt, activation of NF-κB, and increase the expression of IκB [4]. Furthermore, Du et al. have isolated and identified a new water-soluble steroidal saponin from Dioscorea nipponica Makino and defined its chemical structure (as shown in Figure 1(a)) [5]. This newly isolated plant steroidal saponin is named dioscin. "
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