Nebulosides A-B, novel triterpene saponins from under-ground parts of Gypsophila arrostii Guss. var. nebulosa.
A bioassay-guided phytochemical analysis of the triterpene saponins from under ground parts of Gypsophila arrostii var. nebulosa allowed the isolation of two triterpene saponins; nebuloside A, B based on gypsogenin and quillaic acid aglycone. Two new oleanane type triterpenoid saponins (nebuloside A, B) and three known saponins (1-3) were isolated from the root bark of Gypsophila arrostii var. nebulosa. The structures of the two new compounds were elucidated as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester (nebuloside A) and 3-O-β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl(1→3)-β-D-galactopyranosyl-(1→2)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester (nebuloside B), on the basis of extensive spectral analysis and chemical evidence. Nebuloside A and B showed toxicity enhancing properties on saporin a type-I RIP without causing toxicity by themselves at 15 μg/mL.
Pamukkale University, Faculty of Technology, Biomedical Engineering, TR20017 Denizli, Turkey. idris.arslan@yahoo.com
Idris
I
Arslan
Ali
A
Celik
Matthias F
MF
Melzig
D029748:Caryophyllaceae / Q000737:chemistry*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018517:Plant Roots / Q000737:chemistry; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D014315:Triterpenes / Q000737:chemistry*
C582998:3-O-galactopyranosyl-(1-2)-(xylopyranosyl-( 1-3))-glucuronopyranosylquillaic acid 28-O-glucopyranosyl-(1-3)-(xylopyranosyl-(1-3)-xylopyranosyl-(1-4))-rhamnopyranosyl-(1-2)-fucopyranosyl ester; D012503:Saponins; D014315:Triterpenes; C582999:nebuloside B