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Structure elucidation of procyanidin oligomers by low-temperature 1H NMR spectroscopy.
J Agric Food Chem. 2011 Jan 12; 59(1):62-9.JA

Abstract

Procyanidin dimers and trimers, needed as reference compounds for biological studies, have been synthesized from various natural sources using a semisynthetic approach and purified by high-speed countercurrent chromatography (HSCCC). In the past, it has been difficult to elucidate the structure of these compounds, especially the determination of the interflavanoid bond. Here, the structure of two B-type procyanidin dimers, with (+)-catechin ((+)-C) in the upper unit, and eight C-type procyanidin trimers, with (-)-epicatechin ((-)-EC) in the upper unit, have been elucidated using low-temperature (1)H NMR spectroscopy, as well as circular dichroism (CD) spectroscopy. This is the first time NOE interactions have been used to characterize the interflavanoid linkage in underivatized procyanidin trimers. Complete analyses of procyanidin C1 (-)-EC-4β→8-(-)-EC-4β→8-(-)-EC, (-)-EC-4β→8-(-)-EC-4β→8-(+)-C, (-)-EC-4β→6-(-)-EC-4β→8-(-)-EC, (-)-EC-4β→6-(-)-EC-4β→8-(+)-C, (-)-EC-4β→8-(-)-EC-4β→6-(-)-EC, (-)-EC-4β→8-(-)-EC-4β→6-(+)-C, (-)-EC-4β→8-(+)-C-4α→8-(-)-EC, procyanidin C4 (-)-EC-4β→8-(+)-C-4α→8-(+)-C, and procyanidin dimers B6 (+)-C-4α→6-(+)-C and B8 (+)-C-4α→6-(-)-EC are presented.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Esatbeyoglu T
Institute of Food Chemistry, Technische Universität Braunschweig, Braunschweig, Germany.
Jaschok-Kentner B
No affiliation info available
Wray V
No affiliation info available
Winterhalter P
No affiliation info available

MeSH

BiflavonoidsCatechinCold TemperatureDimerizationMagnetic Resonance SpectroscopyMolecular StructureProanthocyanidins

Pub Type(s)

Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21141823

Citation

Esatbeyoglu, Tuba, et al. "Structure Elucidation of Procyanidin Oligomers By Low-temperature 1H NMR Spectroscopy." Journal of Agricultural and Food Chemistry, vol. 59, no. 1, 2011, pp. 62-9.
Esatbeyoglu T, Jaschok-Kentner B, Wray V, et al. Structure elucidation of procyanidin oligomers by low-temperature 1H NMR spectroscopy. J Agric Food Chem. 2011;59(1):62-9.
Esatbeyoglu, T., Jaschok-Kentner, B., Wray, V., & Winterhalter, P. (2011). Structure elucidation of procyanidin oligomers by low-temperature 1H NMR spectroscopy. Journal of Agricultural and Food Chemistry, 59(1), 62-9. https://doi.org/10.1021/jf1032334
Esatbeyoglu T, et al. Structure Elucidation of Procyanidin Oligomers By Low-temperature 1H NMR Spectroscopy. J Agric Food Chem. 2011 Jan 12;59(1):62-9. PubMed PMID: 21141823.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure elucidation of procyanidin oligomers by low-temperature 1H NMR spectroscopy. AU - Esatbeyoglu,Tuba, AU - Jaschok-Kentner,Beate, AU - Wray,Victor, AU - Winterhalter,Peter, Y1 - 2010/12/08/ PY - 2010/12/15/entrez PY - 2010/12/15/pubmed PY - 2011/4/19/medline SP - 62 EP - 9 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 59 IS - 1 N2 - Procyanidin dimers and trimers, needed as reference compounds for biological studies, have been synthesized from various natural sources using a semisynthetic approach and purified by high-speed countercurrent chromatography (HSCCC). In the past, it has been difficult to elucidate the structure of these compounds, especially the determination of the interflavanoid bond. Here, the structure of two B-type procyanidin dimers, with (+)-catechin ((+)-C) in the upper unit, and eight C-type procyanidin trimers, with (-)-epicatechin ((-)-EC) in the upper unit, have been elucidated using low-temperature (1)H NMR spectroscopy, as well as circular dichroism (CD) spectroscopy. This is the first time NOE interactions have been used to characterize the interflavanoid linkage in underivatized procyanidin trimers. Complete analyses of procyanidin C1 (-)-EC-4β→8-(-)-EC-4β→8-(-)-EC, (-)-EC-4β→8-(-)-EC-4β→8-(+)-C, (-)-EC-4β→6-(-)-EC-4β→8-(-)-EC, (-)-EC-4β→6-(-)-EC-4β→8-(+)-C, (-)-EC-4β→8-(-)-EC-4β→6-(-)-EC, (-)-EC-4β→8-(-)-EC-4β→6-(+)-C, (-)-EC-4β→8-(+)-C-4α→8-(-)-EC, procyanidin C4 (-)-EC-4β→8-(+)-C-4α→8-(+)-C, and procyanidin dimers B6 (+)-C-4α→6-(+)-C and B8 (+)-C-4α→6-(-)-EC are presented. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/21141823/Structure_elucidation_of_procyanidin_oligomers_by_low_temperature_1H_NMR_spectroscopy_ L2 - https://doi.org/10.1021/jf1032334 DB - PRIME DP - Unbound Medicine ER -