Four new dammarane saponins from Zizyphus lotus.
Five dammarane-type saponins were isolated by means of centrifugal partition chromatography from the leaves of Zizyphus lotus. Their structures were elucidated using a combination of 1D and 2D 1H and 13C NMR spectra and mass spectroscopy. One of these glycosides is the known jujuboside B (5). Three are new jujubogenin glycosides, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-(2,3,4-O-triacetyl)-alpha-L-rhamnopyranoside (1), 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-alpha-L-rhamnopyranoside (2), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyljujubogenin (3). The last is a new sulfated derivative of jujubasaponine IV, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-beta-D-galactopyranosyl-(20R,22R)-16beta,22:16alpha,30-diepoxydammar-24-ene-3beta,20-diol (4).
Maciuk
Alexandre
A
FRE 2715 CNRS, Laboratoire de Pharmacognosie, IFR 53 Biomolécules, Université de Reims Champagne-Ardenne, Bâtiment 18, CPCBAI, Moulin de la Housse, BP 1039, 51687 Reims Cedex 02, France.
Lavaud
Catherine
C
Thépenier
Philippe
P
Jacquier
Marie-José
MJ
Ghédira
Kamel
K
Zèches-Hanrot
Monique
M
D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*; D014416:Tunisia; D031957:Ziziphus / Q000737:chemistry*; D000097669:Dammaranes
D012503:Saponins; D014315:Triterpenes; D000097669:Dammaranes