Presenegenin glycosides from securidaca welwitschii

Gaoussou Timité, Anne Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Thomas Paululat, Clément Delaude, Marie Aleth Lacaille-Dubois

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The five new presenegenin glycosides 1-5 were isolated from Securidaca welwitschii, together with one known sucrose diester. Compounds 1-4 were obtained as pairs of inseparable (E)/(Z)-isomers of a 3,4-dimethoxycinnamoyl derivative, i.e., 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)-O-α-L-rhamnopyranosyl-(1→2) -O-[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)-O-β- D-xylopyranosyl-(1→4)-O-3-O-acetyl-α-L-rhamnopyranosyl-(1→2) -O-[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)-O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl- (1→2)-β-D-fucopyranosyl] ester (5) (presenegenin=(2β,3β, 4α)-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid).

Original languageEnglish
Pages (from-to)2237-2244
Number of pages8
JournalHelvetica Chimica Acta
Issue number11
Publication statusPublished - Nov 2010


All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Catalysis
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

Timité, G., Mitaine-Offer, A. C., Miyamoto, T., Tanaka, C., Paululat, T., Delaude, C., & Lacaille-Dubois, M. A. (2010). Presenegenin glycosides from securidaca welwitschii. Helvetica Chimica Acta, 93(11), 2237-2244.