Study On Steroidal Saponins From The Rhizomes Of Smilacina Henryi (Baker.) Wang Et Tang

Smilacina henryi (Baker.) Wang et Tang belongs to the Smilacina Desf. genus,Liliaceae family. The aerial part of it is a potherb favored by local people. Therhizomes of it have been used as a Chinese folk medicine for the treatment ofmigraine, headache, rheumatism, irregular menstruation and traumatic injury. Reportson the chemical components of Smilacina henryi are rarely observed and the activeconstituents are not clear so far. Therefore, a detailed phytochemical investigation wasconducted on the rhizomes of the plant.By an extensive use of solvent extraction, TLC, macroporous resin columnchromatography (CC), silica gel CC, C-18reverse phase CC and HPLC, sixcompounds were isolated from the n-butanol fraction of ethanol extract of therhizomes of Smilacina henryi. Five of them were identified as novel steroidalsaponins by a combined analysis of HRMS,1D-NMR and2D-NMR (COSY, HSQC,HMBC, TOCSY, NOESY) spectra. Their structures were elucidated as(25S)-17-hydroxy-5α-spirost-9(11)-en-3-yl O--D-glucopyranosyl(1→2)-[-D-xylopyranosyl(1→3)]--D-glucopyranosyl(1→4)--D-galactopyranoside (SHB50-1a),(25S)-5α-spirost-9(11)-en-3-yl O--D-glucopyranosyl(1→2)-[-D-xylopyranosyl(1→3)]--D-glucopyranosyl(1→4)--D-galactopyranoside (SHB70-2),(25S)-5α-spirost-7-en-3-yl O--D-glucopyranosyl(1→2)-[-D-xylopyranosyl(1→3)]--D-glucopyranosyl(1→4)--D-galactopyranoside (SHB70-3),(25R)-5α-spirost-7-en-3-ylO--D-glucopyranosyl(1→2)-[-D-xylopyranosyl(1→3)]--D-glucopyranosyl(1→4)--D-galactopyranoside (SHB70-4),(25R)-5α-spirost-9(11)-en-3-yl O--D-glucopyranosyl(1→2)-[-D-xylopyranosyl(1→3)]--D-glucopyranosyl(1→4)--D-galactopyranoside (SHB70-5). SHB70-2was subjected to acid hydrolysis andobtained a hydrolysis product SHB70-2H, the structure of which was identified as25(R, S)-Δ9(11)22-isoallospirosten-3-ol.Steroidal saponin was a characteristic chemical components of plants belonging toLiliaceae family. The five saponins isolated from the title plant support the abovepoint and greatly increased the diversity of natural steroidal aglycones.