McDougall Gordon J, Gordon Sandra, Brennan Rex, Stewart Derek
Quality, Health and Nutrition Programme, Genes to Products Theme, Scottish Crop Research Institute, Invergowrie, Dundee DD2 5DA, United Kingdom.
J Agric Food Chem. 2005 Oct 5;53(20):7878-85. doi: 10.1021/jf0512095.
Putative flavanol-anthocyanin condensation products were detected in a polyphenol-rich concentrate from black currant (Ribes nigrum L.). These compounds had UV-vis spectra similar to those of delphinidin-3-O-rutinoside and cyanidin-3-O-rutinoside, but eluted before all previously described anthocyanins on reversed phase HPLC. Mass spectrometric data indicated that they were rutinoside derivatives of novel aglycons 304 amu greater than delphinidin and cyanidin, respectively. The compounds were partly purified by semipreparative HPLC and gave MS and MS2 spectra consistent with anthocyanin rutinosides covalently linked to epigallocatechin or gallocatechin. These compounds are similar in structure to compounds thought to influence color and quality in red wines and strawberry juice products. There was also evidence for the presence of a range of other flavanol-anthocyanin condensation products. The compounds were present at differing levels in juices of 10 black currant varieties, which were roughly correlated to the content of the parent anthocyanins. The flavanol-anthocyanin products were present in polyphenol-enriched concentrates obtained by solid phase extraction, in commercially produced concentrates, and in fresh extracts of black currants. This suggests that the compounds were not artifacts formed during concentration or purification. However, differences in their comparative contents may be related to the lability of the parent anthocyanins during processing. Although present at low levels, the flavanol-anthocyanin products may influence color or quality parameters of black currant juices, and they may confer enhanced stability to the biological activities reported for their anthocyanin parents.
在黑加仑（Ribes nigrum L.）富含多酚的浓缩物中检测到了推定的黄烷醇 - 花青素缩合产物。这些化合物的紫外 - 可见光谱与飞燕草素 - 3 - O - 芸香糖苷和矢车菊素 - 3 - O - 芸香糖苷相似，但在反相高效液相色谱上比所有先前描述的花青素洗脱得早。质谱数据表明，它们分别是比飞燕草素和矢车菊素重304原子质量单位的新型苷元的芸香糖苷衍生物。这些化合物通过半制备高效液相色谱进行了部分纯化，并给出了与共价连接表没食子儿茶素或没食子儿茶素的花青素芸香糖苷一致的质谱和二级质谱。这些化合物的结构与被认为影响红葡萄酒和草莓汁产品颜色和品质的化合物相似。也有证据表明存在一系列其他黄烷醇 - 花青素缩合产物。这些化合物在10个黑加仑品种的果汁中含量不同，大致与母体花青素的含量相关。黄烷醇 - 花青素产物存在于通过固相萃取获得的富含多酚的浓缩物、商业生产的浓缩物以及黑加仑的新鲜提取物中。这表明这些化合物不是在浓缩或纯化过程中形成的假象。然而，它们相对含量的差异可能与加工过程中母体花青素的不稳定性有关。尽管含量较低，但黄烷醇 - 花青素产物可能会影响黑加仑汁的颜色或品质参数，并且它们可能会增强其花青素母体所报道的生物活性的稳定性。
