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Further NMR Investigation and Conformational Analysis of an Acylated Flavonol Glucorhamnoside

✍ Scribed by Jinhai Gao; Genbin Shi; Guoqiang Song; Yu Shao; Bingnan Zhou

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
518 KB
Volume
34
Category
Article
ISSN
0749-1581

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✦ Synopsis

With the combination of various 2D NMR techniques, the structure of an acylated glycoside (1) was unambiguously determined to be kaempferol 3-O-a-(6"'-p-coumaroyIglucosyl-~-l,2-rhamnoside). The complete 'H and I3C resonance assignments were obtained. Based on NMR data and molecular dynamics simulations in DMSO solvent using periodic boundary conditions, a folded conformation was elucidated for 1 in solution, implying a hydrophobic interaction between the aromatic nuclei of aglycone and the acyl group. Such hydrophobic stacking is further assisted by a weak intramolecular hydrogen bond between OH3" on glucose and 02"' on rhamnose, as indicated directly by the NMR behaviour (temperature coefficients ds/dT, NOES and coupling constants JH-) of the hydroxyl protons on the sugar rings.

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