Planta Med 2010; 76 - P552
DOI: 10.1055/s-0030-1264850

Chemotaxonomic study of the Polygalaceae family: saponins from Securidaca welwitschii

G Timité 1, A Mitaine-Offer 2, T Miyamoto 3, T Paululat 4, C Delaude 5, M Lacaille-Dubois 6
  • 1University of Burgundy, Faculty of Pharmacy, Laboratory of Pharmacognosy, EA 3660, 7, Bd Jeanne D'Arc, 21079 Dijon, France
  • 2University of Burgundy, Faculty of Pharmacy, Laboratory of Pharmacognosy, EA 3660, 7, Bd Jeanne D'Arc, 21079 Dijon, France
  • 3Kyushu University, Graduate School of Pharmaceutical Sciences, Maidashi Higashi Ku 3–1-1, 812–8582 Fukuoka, Japan
  • 4University Siegen, Department of Organic chemistry, Adolf-Reichwein-Strasse 2, 57968 Siegen, Germany
  • 5University of Liège, Centre de recherche phytochimique, Sart Tilman, 4000 Liège, Belgium
  • 6University of Bourgundy, Faculty of Pharmacy, Laboratory of Pharmacognosy, EA 3660, 7, Bd Jeanne d'Arc, 21079 Dijon, France

From a chemotaxonomic point of view, in a continuation of our study on saponin constituents of the Polygalaceae family [1–3], we have examined the saponin fraction of stem barks of S. welwitschii. Five new presenegenin glycosides 1-5 were isolated by successive MPLC over silica gel, together with one known oligosaccharide multi-ester, 1-4 as two inseparable (E)/(Z)-isomers of a 3,4-dimethoxycinnamoyl derivative (1/2 and 3/4). Their structures were elucidated mainly by 2D-NMR techniques and mass spectrometry as 3-O-(β-D-glucopyranosyl)presenegenin 28-O-{β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[ β-D-glucopyranosyl-(1→3)]-4-O-[(E)-3,4-dimethoxycinnamoyl]- β-D-fucopyranosyl} ester (1) and its (Z)-isomer (2), 3-O-(β-D-glucopyranosyl)presenegenin 28-O-{β-D-galactopyranosyl-(1→4)- β-D-xylopyranosyl-(1→4)-3-O-acetyl-α-L-rhamnopyranosyl-(1→2)-[ β-D-glucopyranosyl-(1→3)]-4-O-[(E)-3,4-dimethoxycinnamoyl]- β-D-fucopyranosyl} ester (3) and its (Z)-isomer (4), and 3-O-(β-D-glucopyranosyl)presenegenin 28-O-{β-D-galactopyranosyl-(1→3)- β-D-xylopyranosyl-(1→4)- α -L-rhamnopyranosyl-(1→2)-O-β-D-fucopyranosyl} ester (5).

References: 1. Mitaine-Offer, A. C. et al. (2009) Phytochemistry. 71: 90–94.

2. Mitaine-Offer, A. C. et al. (2002)J. Nat. Prod. 65: 553–557.

3. Haddad, M. et al. (2003)J. Nat. Prod. 66: 372–377.