Electronic structure calculations as a tool for investigating acyl migrations in ester saponins.
The possibility of acyl migrations in ester saponins from Maesa lanceolata was investigated by molecular mechanics and electronic structure calculations carried out on the major constituent maesasaponin IV3 (3beta-O-[[alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-[beta-D-galactopyranosyl-(1-->2)]-beta-D-gluco-pyranuronyl]-21beta-angeloyloxy-22alpha-propanoyloxy-13beta,28-oxido-olean-16alpha, 28alpha-diol). It was confirmed that acyl migrations could occur in rings D and E of maesasaponins.
Apers
Sandra
S
Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium. Sandra.apers@ua.ac.be
Everaert
Gert
G
van der Veken
Benjamin J
BJ
Vlietinck
Arnold J
AJ
Pieters
Luc A C
LA
D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D029623:Primulaceae / Q000737:chemistry; D012503:Saponins / Q000737:chemistry*
D004952:Esters; D012503:Saponins; C477626:maesasaponin IV3