Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography
Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography
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DOI：
10.1016/j.foodchem.2015.01.130
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发表时间：
2015-07-15
期刊：
影响因子：
8.8
通讯作者：
Winterhalter, Peter
中科院分区：
文献类型：
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作者：
Esatbeyoglu, Tuba;Wray, Victor;Winterhalter, Peter
从未经烘焙的可可豆(Theobroma Cacao L.)中分离得到主要原花青素，包括二聚体B2和B5、三聚体Cl、四聚体和五聚体。使用各种逆流层析技术，如高速逆流层析(HSCCC)、低速旋转逆流层析(LSRCCC)和螺旋线圈逆流层析。此外，以(+)-儿茶素为亲核剂，将可可豆聚合物半合成后，经逆流层析分离得到二聚原花青素B1和B7，它们是可可豆中天然不存在的。通过这种方法，可以在一次运行中分离出相当数量的二聚原花青素B1(500 mg，纯度为97%)。这是首次报道用逆流层析从可可中分离和半合成二聚体到五聚体的原花青素。此外，还根据H-1核磁共振波谱确定了四聚体(肉桂单宁A2)和五聚原花青素(肉桂单宁A3)的化学结构。首次通过NOE相关性确定了黄烷类化合物间的相互作用。(C)2015爱思唯尔有限公司。保留所有权利。
The main procyanidins, including dimeric B2 and B5, trimeric Cl, 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 H-1 NMR spectroscopy. Interflavanoid linkage was determined by NOE-correlations, for the first time. (C) 2015 Elsevier Ltd. All rights reserved.