Tupichinins B–D, three new spirostanol saponins from Tupistra chinensis rhizomes

Abstract

Three new spirostanol saponins were isolated from the EtOAc fraction of methanol extract from Tupistra chinensis rhizomes. Based on the detailed analysis of their 1D and 2D NMR spectra and chemical evidence, their structures were determined as 1β-O-acetyl-spirost-5,25(27)-dien-3α-yl-O-β-D-glucopyranoside (1), (25S)-1β,2β,5β-trihydroxy-spirostane-3β-yl-O-β-D-glucopyranoside (2) and (25S)-1β,2β-dihydroxy-5β-spirostane-3β-yl-O-β-D-xylopyranoside (3), respectively.

Genus Tupistra: A Comprehensive Review of Phytochemistry and Pharmacological Activity

“…T. chinensis, T. wattii, and T. yunnanensis are main sources of spirostanol and furostanol saponins. Sixty-five compounds were assigned as spirostanol saponins (Table 1 and Figure 2), 2,[7][8][9][10]21,22,24,28,[31][32][33]35,36,39 while compounds 85 to 150 are furostanol saponins (Table 1 and Figure 3). 5,8,10,18,22,24,31,35,37,[39][40][41][42][43][44][45][46][47] Taking spirostanol saponins into consideration, glycosylation generally happens at C-1, C-3, C-5, and C-24.…”

“…T. chinensis , T. wattii , and T. yunnanensis are main sources of spirostanol and furostanol saponins. Sixty-five compounds ( 30 - 84 ) were assigned as spirostanol saponins (Table 1 and Figure 2), 2,7–10,21,22,24,28,31–33,35,36,39 while compounds 85 to 150 are furostanol saponins (Table 1 and Figure 3). 5,8,10,18,22,24,31,35,37,39–47…”

“…7 Three new saponins, tupichinins B-D ( 73-75 ), were also isolated from the EtOAc fraction of T. chinensis rhizome. 2 A new polyhydroxylated saponin, tupisteroide A ( 76 ), was obtained as a white amorphous powder from the n -BuOH fraction of T. chinensis air-dried powdered rhizome. 31 Two new saponins, tupistrosides A-B ( 77-78 ), were obtained, glycosylated at C-3.…”

“…It contains about 26 species. 2 Plants of this genus are of great value in folk medicine, for example, the rhizome of Tupistra chinensis Baker is always recognized as one of the ingredients for pain attenuation, blood stasis dissipation, detoxification, traumatic injury, and rheumatoid arthralgia. 3 Tupistra nutans Wall.…”