An efficient method was established by high-speed counter-current chromatography (HSCCC) for preparation of four phenolic compounds from the depolymerization products of persimmon tannin. Using the two solvent systems of n-hexane/ethyl acetate/water (3:17:20, v/v/v) and ethyl acetate/methanol/water (50:1:50, v/v/v), the preparative isolation was successfully performed by a two-step separation. The yields of one run (150 mg crude sample) for gallic acid, methyl gallate, and epigallocatechin-3-gallate-(4β → 8, 2β → O → 7)-epigallocatechin-3-gallate dimer (A-type EGCG dimer) were 4.7, 44.2 and 5.9 mg, respectively. In addition, 4.6 mg epicatechin-3-gallate-(4β → 8, 2β → O → 7)-epicatechin-3-gallate dimer (A-type ECG dimer) was obtained by further preparative high-performance liquid chromatography (prep-HPLC). The purities of these compounds were all above 95.0% and their structures were identified by HPLC/ESI-MS. We found that HSCCC had definite advantages for the preparation of dimeric procyanidins compared with previous methods. Furthermore, it was shown that the four phenolic compounds possessed greater antioxidant activities than Trolox.

通过高速逆流色谱法（HSCCC）建立了一种从柿单宁解聚产物中制备四种酚类化合物的有效方法。使用两个溶剂系统Ñ己烷/乙酸乙酯/水（3点一十七分20秒，V / V / V）和乙酸乙酯/甲醇/水（50：1：50，V / V / V），通过两步分离成功完成了制备性分离。一次运行（150 mg粗样品）的没食子酸，没食子酸甲酯和表没食子儿茶素-3-没食子酸酯-（4β→8，2β→O→7）-表没食子儿茶素-3-没食子酸酯的产率（A型EGCG二聚体）分别为4.7、44.2和5.9毫克。此外，通过进一步的制备型高效液相色谱法（制备型HPLC）获得了4.6 mg表儿茶素-3-没食子酸酯-（4β→8，2β→O→7）-表儿茶素-3-没食子酸酯（A型ECG二聚体） ）。这些化合物的纯度都在95.0％以上，并且通过HPLC / ESI-MS鉴定了它们的结构。我们发现，与以前的方法相比，HSCCC在制备二聚体原花青素方面具有明显的优势。此外，还显示出四种酚类化合物比Trolox具有更大的抗氧化活性。