Food Safety and Analytical Quality Control Laboratory, Central Food Technological Research Institute, Council of Scientific & Industrial Research, KRS Road, Mysore 570020, India.
J Agric Food Chem. 2012 Feb 15;60(6):1522-7. doi: 10.1021/jf204185y. Epub 2012 Feb 6.
The L-lysine- and L-arginine-derived Amadori and Heyns products consisting of N-(1-deoxy-d-fructos-1-yl)amino acid and N-(2-deoxy-d-glucos-2-yl)amino acid were prepared by reaction of d-fructose and d-glucose with l-lysine hydrochloride and l-arginine hydrochloride using commercial zinc powder as deprotonating reagent and also as catalyst precursor in a simple synthetic route in high yield. These compounds were screened for angiotensin I-converting enzyme (ACE) inhibitory activity using a high-throughput colorimetric assay (utilizing porcine kidney ACE). The IC(50) values fall in the range of 1030-1175 μM, with N(α)-(1-deoxy-d-fructos-1-yl)arginine showing the best IC(50) value (1030 ± 38 μM). This study demonstrates an improved synthetic method for simple Amadori and Heyns products and their moderate ACE inhibitor activity.
由 L-赖氨酸和 L-精氨酸衍生的 Amadori 和 Heyns 产物由 d-果糖和 d-葡萄糖与 l-赖氨酸盐酸盐和 l-精氨酸盐酸盐反应制备，使用商业锌粉作为脱质子试剂，并且也是简单合成路线中催化剂前体，产率很高。这些化合物通过高通量比色测定法（利用猪肾 ACE）筛选血管紧张素 I 转化酶（ACE）抑制活性。IC（50）值在 1030-1175 μM 范围内，其中 N（α）-（1-脱氧-d-果糖-1-基）精氨酸显示出最佳的 IC（50）值（1030±38μM）。本研究证明了一种改进的简单 Amadori 和 Heyns 产物的合成方法及其适度的 ACE 抑制活性。
