Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 7101-7110 |
| Seitenumfang | 10 |
| Fachzeitschrift | Journal of Agricultural and Food Chemistry |
| Jahrgang | 62 |
| Ausgabenummer | 29 |
| Publikationsstatus | Veröffentlicht - 23 Juli 2014 |
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.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Allgemeine Chemie
- Agrar- und Biowissenschaften (insg.)
- Allgemeine Agrar- und Biowissenschaften
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in: Journal of Agricultural and Food Chemistry, Jahrgang 62, Nr. 29, 23.07.2014, S. 7101-7110.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Semisynthetic preparation and isolation of dimeric procyanidins B1-B8 from roasted hazelnut skins (Corylus avellana L.) on a large scale using countercurrent chromatography
AU - Esatbeyoglu, T.
AU - Juadjur, A.
AU - Wray, V.
AU - Winterhalter, P.
N1 - Copyright: Copyright 2014 Elsevier B.V., All rights reserved.
PY - 2014/7/23
Y1 - 2014/7/23
N2 - 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.
AB - 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.
KW - NMR spectroscopy
KW - countercurrent chromatography
KW - hazelnut (Corylus avellana L.)
KW - procyanidins
KW - prodelphinidins
KW - propelargonidins
KW - semisynthesis
UR - http://www.scopus.com/inward/record.url?scp=84905592334&partnerID=8YFLogxK
U2 - 10.1021/jf501312a
DO - 10.1021/jf501312a
M3 - Article
VL - 62
SP - 7101
EP - 7110
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 29
ER -