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Electronic structure calculations as a tool for investigating acyl migrations in ester aponins
Author(s) -
Apers Sandra,
Everaert Gert,
Veken Benjamin J. van der,
Vlietinck Arnold J.,
Pieters Luc A. C.
Publication year - 2002
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/pca.653
Subject(s) - chemistry , stereochemistry , diol , computational chemistry , organic chemistry
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 IV 3 (3β‐O‐{[α‐ L ‐rhamnopyranosyl‐(1→2)‐β‐ D ‐galactopyranosyl‐(1→3)]‐[β‐ D ‐galactopyranosyl‐(1→2)]‐β‐ D ‐glucopyranuronyl}‐21β‐angeloyloxy‐22α‐propanoyloxy‐13β,28‐oxido‐olean‐16α, 28α‐diol). It was confirmed that acyl migrations could occur in rings D and E of maesasaponins. Copyright © 2002 John Wiley & Sons, Ltd.