Semisynthetic preparation and isolation of dimeric procyanidins B1-B8 from roasted hazelnut skins (Corylus avellana L.) on a large scale using countercurrent chromatography

verfasst von

T. Esatbeyoglu, A. Juadjur, V. Wray, P. Winterhalter

Abstract

Dimeric procyanidins B1-B8 were produced via semisynthesis from a polymeric proanthocyanidin fraction of hazelnut skins (Corylus avellana L.). This polymeric fraction was found to consist mostly of (+)-catechin and (-)-epicatechin as upper units. Therefore, according to the choice of nucleophile agent, it is possible to semisynthesize dimeric procyanidins B1, B3, B6, and B7 with (+)-catechin and B2, B4, B5, and B8 with (-)-epicatechin. The semisynthetic mixtures were separated on a preparative scale using high-speed countercurrent chromatography (HSCCC) and low-speed rotary countercurrent chromatography (LSRCCC). C4 → C8 linked dimeric procyanidins B1-B4 were isolated in amounts of 350-740 mg. To the best of the authors' knowledge this is the first study isolating dimeric procyanidins B1-B8 in large amounts with countercurrent chromatography. Moreover, the dimeric prodelphinidins B1, B2, and B3 and their structural elucidation by

¹H NMR spectroscopy without derivatization are described for hazelnuts as natural compounds for the first time.

Organisationseinheit(en)

Institut für Lebensmittelwissenschaft und Humanernährung
Molekulare Lebensmittelchemie und -entwicklung

Typ

Artikel

Journal

Journal of Agricultural and Food Chemistry

Band

Seiten

7101-7110

Anzahl der Seiten

ISSN

0021-8561

Publikationsdatum

23.07.2014

Publikationsstatus

Veröffentlicht

Peer-reviewed

ASJC Scopus Sachgebiete

Allgemeine Chemie, Allgemeine Agrar- und Biowissenschaften

Elektronische Version(en)

https://doi.org/10.1021/jf501312a (Zugang: Geschlossen)