Elucidation of production mechanism and functionality of the decolorized compounds from acylated anthocyanins under interstine condition

阐明间质条件下酰化花青素脱色化合物的产生机制和功能

• 批准号: 12660124
• 负责人: TERAHARA Norihiko
• 金额: $ 1.86万
• 依托单位: MINAMI-KYUSHU UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2000
• 资助国家: 日本
• 起止时间: 2000 至 2001
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-12660124/
• 关键词: Red morning glory; Acylated anthocyanins; AGH inhibitory activity; Intestinal fluid solution; Faded molecular species; Pseudobase; Chalcone; Preparative ODS-HPLC system; 紫甘藷; フラビリウム型色素; ODS分取HPLCシステム

Large-scale preparation of pure pigments was able to be comparatively performed from the purple sweet potato storage roots and the red morning glory petals in a short time by combining isolation and purification by column chromatographies such as XAD-2000, PVP and preparative HPLC. These were confirmed to be acylated anthocyanins with 3-sophoroside-5-glucoside as a common frame. As a result of putting the isolated acylated anthocyanins for 24 hours on the intestinal tract environment (pH 6.8, 37℃, darkness), the degree of fading (instability) was the order of YGM-5b > SOA-4 > YGM-3 and 6 > SOA-6. This result differs from the order (SOA-4 > SOA-6 > YGM-6 and 3) of AGH inhibitory activity, and not correlating made instability and AGH inhibitory activity clear.In this reaction solution, three kinds of components considered to be an anhydrobase (A), a pseudobase (B), and a chalcone (C) were found. The reaction progressed like A→B→C with time and the compositions led to A:B:C≒1:1:2 except f … More or YGM-5b and SOA-6 after 24 hours. All pigments were holding caffeic acid.Next, SOA-4 was faded under the intestinal tract environment in large quantities, and isolation and purification of C were tried using preparative HPLC. Consequently, when a neutral phosphate buffer solution system was used as eluent, C and other components could be separated, and C has been isolated with sufficient reproducibility. Moreover, it was strongly suggested as a result of mass analysis that component C is a chalcone which was generated from SOA-4 through hydrationand isomerization. Now, the desalting and the structural analysis by NMR are planned. Moreover, it is under examination also about isolation of the remaining components A and B.It was thought that its 3-acylateded sugar side-chain structure (6-cafffeoylshophorose moiety) which SOA-4, -6 and YGM-3, and -6 have in common was indispensable to the expression of AGH inhibitory activity since the activity of SOA-4 doesnot change with fading (structural transformation of the aglycon part). Less

采用XAD-2000、PVP和制备型HPLC等柱色谱分离纯化相结合的方法，可在较短时间内实现紫甘薯块根和红色牵牛花花瓣色素的大规模制备。这些化合物被证实是以3-槐糖苷-5-葡萄糖苷为骨架的酰化花青素。在pH6.8、37℃、黑暗的肠道环境中放置24 h，其褪色程度（不稳定性）为YGM-5 b> SOA-4 > YGM-3和6 > SOA-6。结果表明，该反应体系中存在三种组分，分别为脱水碱（A）、假碱（B）和查耳酮（C）。反应过程为A→B→C，其组成为A：B：C = 1：1：2，但反应时间越长，其组成越不稳定，其抑制活性越强 ...更多信息 或YGM-5 b和SOA-6。其次，在大量肠道环境下，SOA-4褪色，并尝试用制备型HPLC分离纯化C。因此，当使用中性磷酸盐缓冲溶液系统作为洗脱剂时，C和其他组分可以分离，并且C已经以足够的重现性分离。此外，质量分析结果表明，组分C是由SOA-4通过水合和异构化生成的查尔酮。现在，计划通过NMR进行结构分析。此外，还对剩余组分A和B的分离进行了研究。据认为，SOA-4、SOA-6和YGM-3和YGM-6共同具有的3-酰化糖侧链结构（6-咖啡酰基shophorose部分）对于表达AGH抑制活性是必不可少的，因为SOA-4的活性不随褪色（糖苷配基部分的结构转化）而改变。少