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

authored by

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.

Organisation(s)

Institute of Food Science and Human Nutrition
Molecular Food Chemistry and Food Development

Type

Article

Journal

Journal of Agricultural and Food Chemistry

Volume

Pages

7101-7110

No. of pages

ISSN

0021-8561

Publication date

23.07.2014

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Chemistry(all), Agricultural and Biological Sciences(all)

Electronic version(s)

https://doi.org/10.1021/jf501312a (Access: Closed)