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Semisynthetic Preparation and Isolation of Dimeric Procyanidins B1–B8 from Roasted Hazelnut Skins (Corylus avellana L.) on a Large Scale Using Countercurrent Chromatography

Author:
Esatbeyoglu, Tuba, Juadjur, Andreas, Wray, Victor, Winterhalter, Peter
Source:
Journal of agricultural and food chemistry 2014 v.62 no.29 pp. 7101-7110
ISSN:
0021-8561
Subject:
Corylus avellana, countercurrent chromatography, derivatization, hazelnuts, nuclear magnetic resonance spectroscopy, proanthocyanidins, procyanidins
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.
Agid:
4686933