Tannins and flavonoids are secondary metabolites of plants that display a wide array of biological activities. This peculiarity is related to the inhibition of extracellular enzymes that occurs through the complexation of peptides by tannins. Not only the nature of these interactions, but more fundamentally also the structure of these heterogeneous polyphenolic molecules are not completely clear. This first paper describes the development of a new analytical method for the structural characterization of tannins on the basis of tannin model compounds employing an in situ labeling of all labile H groups (aliphatic OH, phenolic OH, and carboxylic acids) with a phosphorus reagent. The P-31 NMR analysis of P-31 labeled samples allowed the unprecedented quantitative and qualitative structural characterization of hydrolyzable tannins, proanthocyanidins, and catechin tannin model compounds, forming the foundations for the quantitative structural elucidation of a variety of actual tannin samples described in part 2 of this series.

Melone, F., Saladino, R., Lange, H., Crestini, C. (2013). Tannin Structural Elucidation and Quantitative P-31 NMR Analysis. 1. Model Compounds. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 61(39), 9316-9324 [10.1021/jf401477c].

Tannin Structural Elucidation and Quantitative P-31 NMR Analysis. 1. Model Compounds

CRESTINI, CLAUDIA
2013-01-01

Abstract

Tannins and flavonoids are secondary metabolites of plants that display a wide array of biological activities. This peculiarity is related to the inhibition of extracellular enzymes that occurs through the complexation of peptides by tannins. Not only the nature of these interactions, but more fundamentally also the structure of these heterogeneous polyphenolic molecules are not completely clear. This first paper describes the development of a new analytical method for the structural characterization of tannins on the basis of tannin model compounds employing an in situ labeling of all labile H groups (aliphatic OH, phenolic OH, and carboxylic acids) with a phosphorus reagent. The P-31 NMR analysis of P-31 labeled samples allowed the unprecedented quantitative and qualitative structural characterization of hydrolyzable tannins, proanthocyanidins, and catechin tannin model compounds, forming the foundations for the quantitative structural elucidation of a variety of actual tannin samples described in part 2 of this series.
2013
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/03 - CHIMICA GENERALE E INORGANICA
English
Con Impact Factor ISI
Melone, F., Saladino, R., Lange, H., Crestini, C. (2013). Tannin Structural Elucidation and Quantitative P-31 NMR Analysis. 1. Model Compounds. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 61(39), 9316-9324 [10.1021/jf401477c].
Melone, F; Saladino, R; Lange, H; Crestini, C
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/85210
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