New triterpenoid saponins from Leontice smirnowii.
Three new triterpene saponins, leonticins I (1), J (2) and L (3) were isolated from the tubers of Leontice smirnowii. On the basis of spectroscopic methods, including 2D NMR experiments (DEPT, gs-COSY, gs-HMQC, gs-HMBC and gs-HSQC-TOCSY), mass spectrometry (HR-ESI-MS) and chemical degradation, the structures of the new compounds were elucidated as 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-1 → 2)]-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (1), 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (2) and 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)]-[β-D-xylopyranosyl-(1 → 2)]-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (3), respectively. The aglycone 3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid was observed for the first time in Leontice species.
Tabatadze
Nino
N
Institute of Pharmacochemistry, Academy of Sciences of Georgia, 36, St. P. Sarajishvili, 0159, Tbilisi, Georgia.
Bun
Sok-Siya
SS
Tabidze
Badri
B
Mshvildadze
Vakhtang
V
Dekanosidze
Genri
G
Ollivier
Evelyne
E
Elias
Riad
R
D028141:Berberidaceae / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification; D035281:Plant Tubers; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*
D010936:Plant Extracts; D012503:Saponins; D014315:Triterpenes; C557386:leonticin I; C557384:leonticin J; C557385:leonticin L