TY - JOUR

T1 - Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography

AU - Esatbeyoglu, T.

AU - Wray, V.

AU - Winterhalter, P.

N1 - Funding information: The authors thank B. Jaschok-Kentner and C. Kakoschke (Helmholtz Centre for Infection Research, Braunschweig, Germany) for NMR analyses and C. Keilholz (Institute of Food Chemistry, Technische Universität Braunschweig, Germany) for technical assistance. N. Köhler and U. Engelhardt (Institute of Food Chemistry, Technische Universität Braunschweig, Germany) are thanked for fruitful discussions. We are grateful to the German Federal Ministry of Education and Research (BMBF – Bundesministerium für Bildung und Forschung – Germany, Grant 0313828C ) for financial support.

PY - 2015/7/15

Y1 - 2015/7/15

N2 - The main procyanidins, including dimeric B2 and B5, trimeric C1, tetrameric and pentameric procyanidins, were isolated from unroasted cocoa beans (Theobroma cacao L.) using various techniques of countercurrent chromatography, such as high-speed countercurrent chromatography (HSCCC), low-speed rotary countercurrent chromatography (LSRCCC) and spiral-coil LSRCCC. Furthermore, dimeric procyanidins B1 and B7, which are not present naturally in the analysed cocoa beans, were obtained after semisynthesis of cocoa bean polymers with (+)-catechin as nucleophile and separated by countercurrent chromatography. In this way, the isolation of dimeric procyanidin B1 in considerable amounts (500 mg, purity > 97%) was possible in a single run. This is the first report concerning the isolation and semisynthesis of dimeric to pentameric procyanidins from T. cacao by countercurrent chromatography. Additionally, the chemical structures of tetrameric (cinnamtannin A2) and pentameric procyanidins (cinnamtannin A3) were elucidated on the basis of 1H NMR spectroscopy. Interflavanoid linkage was determined by NOE-correlations, for the first time.

AB - The main procyanidins, including dimeric B2 and B5, trimeric C1, tetrameric and pentameric procyanidins, were isolated from unroasted cocoa beans (Theobroma cacao L.) using various techniques of countercurrent chromatography, such as high-speed countercurrent chromatography (HSCCC), low-speed rotary countercurrent chromatography (LSRCCC) and spiral-coil LSRCCC. Furthermore, dimeric procyanidins B1 and B7, which are not present naturally in the analysed cocoa beans, were obtained after semisynthesis of cocoa bean polymers with (+)-catechin as nucleophile and separated by countercurrent chromatography. In this way, the isolation of dimeric procyanidin B1 in considerable amounts (500 mg, purity > 97%) was possible in a single run. This is the first report concerning the isolation and semisynthesis of dimeric to pentameric procyanidins from T. cacao by countercurrent chromatography. Additionally, the chemical structures of tetrameric (cinnamtannin A2) and pentameric procyanidins (cinnamtannin A3) were elucidated on the basis of 1H NMR spectroscopy. Interflavanoid linkage was determined by NOE-correlations, for the first time.

KW - Cocoa (Theobroma cacao L.)

KW - Countercurrent chromatography

KW - Isolation

KW - NMR spectroscopy

KW - Procyanidins

KW - Semisynthesis

UR - http://www.scopus.com/inward/record.url?scp=84922739246&partnerID=8YFLogxK

U2 - 10.1016/j.foodchem.2015.01.130

DO - 10.1016/j.foodchem.2015.01.130

M3 - Article

VL - 179

SP - 278

EP - 289

JO - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

ER -