Document Type
Article
Publication Title
ARKIVOC
Department
Chemistry
ISSN
1551-7012
Volume
2014
Issue
5
DOI
10.3998/ark.5550190.p008.583
First Page
1
Last Page
29
Publication Date
1-1-2014
Abstract
The NMR-structures of six polyphenols, resveratrol (1), (-)-epicatechin (2), pelargonidin chloride (3), cyanidin chloride (4), cyanin chloride (5), and keracyanin chloride (6), were fully assigned. For the glycosylated polyphenols 5 and 6, the three-dimensional solution structure and long-range 1 H- 13C-coupling constants across the glycosidic bond were measured. Satisfactory fit to standard Karplus-equations was achieved for glycosides directly attached to the aromatic core in cyanin chloride. Molecular dynamics simulation data in vacuum at the AM1-level of theory were shown to approximate the NMR-solution data reasonably well. Selective HCl-catalyzed H/D-exchange was observed for aromatic protons H6 and H8 in flavonoid structures containing a 5,7-metadisubstituted chromelynium core with free OH-groups. The exchange took place readily in compounds 3, 4, and 6, whereas 1, 2, and 5 did not exchange.
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Recommended Citation
Franz, A. H.,
Serebnitskaya, I.,
Gudial, G.,
&
Wallis, C.
(2014).
Structure assignment and H/D-exchange behavior of several glycosylated polyphenols.
ARKIVOC, 2014(5), 1–29.
DOI: 10.3998/ark.5550190.p008.583
https://scholarlycommons.pacific.edu/cop-facarticles/143