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Structure elucidation of cyanidin‐3‐sambubioside and assignments of the 1 H and 13 C NMR resonances through two‐dimensional shift‐correlated NMR techniques
Author(s) -
Andersen Øyvind M.,
Aksnes Dagfinn W.,
Nerdal Willy,
Johansen OleP.
Publication year - 1991
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.2800020407
Subject(s) - chemistry , heteronuclear molecule , homonuclear molecule , two dimensional nuclear magnetic resonance spectroscopy , heteronuclear single quantum coherence spectroscopy , nuclear magnetic resonance spectroscopy , proton , analytical chemistry (journal) , proton nmr , spectroscopy , computational chemistry , nuclear magnetic resonance , stereochemistry , chromatography , molecule , organic chemistry , physics , quantum mechanics
Abstract The anthocyanin cyanidin‐3‐sambubioside was isolated from the acidified methanolic extract of the fruits of Sambucus nigra by successive application of an ion exchange resin, droplet countercurrent chromatography and gel filtration. By means of chemical degradation and spectroscopy (especially one‐ and two‐dimensional NMR techniques) the structure has been determined to be cyanidin‐3‐O‐β‐D‐xylopyranosyl‐(1±2)‐β‐D‐glucopyranoside with both the sugar rings assuming a 4 C 1 chair conformation. The combination of several NMR techniques such as double‐quantum filtered proton‐proton shift correlation (DQF‐COSY), homonuclear Overhauser enhancement (NOE) difference spectroscopy, heteronuclear coupling‐modulated spin echo, proton‐carbon shift correlation optimized for direct (HSC) and long‐range coupling (COLOC) provided assignments of the 1 H and 13 C signals. The coupling constants of the sugar protons were obtained by iterative spin simulation. This is the first report of a heteronuclear shift correlation experiment applied on anthocyanins.