Department of Analytical Chemistry, Cracow University of Technology, 24 Warszawska Str, 31-155, Cracow, Poland.
Department of Pharmaceutical Microbiology with Laboratory for Microbiological Diagnostics, Medical University of Lublin, 1 Chodzki Str, 20-093, Lublin, Poland.
J Pharm Biomed Anal. 2018 Nov 30;161:83-93. doi: 10.1016/j.jpba.2018.08.025. Epub 2018 Aug 15.
High-speed counter-current chromatography (HSCCC) combined with HPLC were established to purify, for the first time, betacyanin isomers from Gomphrena globosa L. flowers. The mixture of tert-butyl methyl ether - butanol - methanol - water TBME-BuOH-MeOH-HO (1.0% heptafluorobutyric acid HFBA) 2:2:1:5 (v/v/v/v) in reversed phase mode was used for preliminary purification of gomphrenin derivatives. Then, semiprep-HPLC was used to obtained ten pure betacyanins: gomphrenins II and III with their cis-isomers as well as sinapoyl-gomphrenin I and its corresponding diastereomers. This is the first study on separation of naturally coexisting acylated gomphrenin isomers. The isolated compounds showed a broad antimicrobial spectrum (in the range of 0.19-1.5 mg mL) by inhibiting the growth of all of food-borne pathogens tested. The antimicrobial activity of acylated betacyanins was higher than that of non-acylated gomphrenin I/isogomphrenin I. Therefore, the acylation with phenolic acids increases the activity of betacyanins against fungi and bacteria, suggesting a synergetic effect of the acylated moieties and the pigment chromophoric system on the activity, which was evaluated for the first time.
高速逆流色谱（HSCCC）结合高效液相色谱（HPLC）首次从鸡冠花中分离纯化甜菜红素异构体。在反相模式下，使用 TBME-BuOH-MeOH-HO（1.0%七氟丁酸 HFBA）2:2:1:5（v/v/v/v）的叔丁基甲基醚-丁醇-甲醇-水混合物对鸡冠花衍生化合物进行初步纯化。然后，采用半制备 HPLC 获得了十种纯的甜菜红素：gomphrenins II 和 III 及其顺式异构体，以及 sinapoyl-gomphrenin I 和其相应的非对映异构体。这是首次对天然共存酰化 gomphrenin 异构体进行分离的研究。分离得到的化合物通过抑制所有测试的食源性病原体的生长，表现出广谱的抗菌活性（范围为 0.19-1.5mg/mL）。酰化甜菜红素的抗菌活性高于非酰化的 gomphrenin I/isogomphrenin I。因此，酚酸的酰化增加了甜菜红素对真菌和细菌的活性，表明酰化部分和色素生色系统对活性具有协同作用，这是首次进行评估。
