Authors: Thierry Buffeteau, Dominique Cavagnat, Jonathan Bisson , Axel Marchal, Gilbert D. Kapche, Ilaria Battistini, Gregory Da Costa, Alain Badoc, Jean-Pierre Monti, Jean-Michel Mérillon, Pierre Waffo-Téguo
Journal: Journal of Natural Products (RoMEO status: White) 77(8), 1981-1985, (2014)
Subjects: Pharmacognosy Phytochemistry VCD Stereochemistry
Dimeric stilbene glucosides 1–3 [two diastereomers of (−)-gnemonoside A (1a and 1b), (−)-gnemonoside C (2), and (−)-gnemonoside D (3)] as well as a mixture of the two enantiomers of gnetin C (4) were isolated from the rhizomes of Gnetum africanum. The two enantiomers of gnetin C, (+)-4 and (−)-4, were obtained from the aglycones of 1a and 1b, respectively. The configurations of these stilbenoids were investigated by NMR and vibrational circular dichroism (VCD) experiments. The absolute configurations of (−)-1a, (−)-2, (−)-3, and (−)-4 were established as 7aS,8aS by VCD spectroscopy in combination with density functional theory calculations. The antiamyloidogenic activity of the isolated stilbenes was also evaluated versus beta-amyloid fibrils. The four glucosides of gnetin C (1a, 1b, 2, and 3) were found to be the most active compounds, with inhibition percentages of 56, 56, 58, and 54 at 10 μM, respectively.