碳水化合物氨基酸酯的血管紧张素转换酶抑制活性

Angiotensin converting enzyme inhibitory activity of amino acid esters of carbohydrates.

作者信息

Kamath Vasudeva, Rajini P S, Lohith K, Somashekar B R, Divakar S

机构信息

Food Protectants and Infestation Control Department, Central Food Technological Research Institute, Mysore 570 020, India.

出版信息

Int J Biol Macromol. 2006 Mar 30;38(2):89-93. doi: 10.1016/j.ijbiomac.2006.01.008. Epub 2006 Mar 10.

DOI:10.1016/j.ijbiomac.2006.01.008

PMID:16529809

Abstract

L-alanyl-D-glucose, L-valyl-D-glucose, L-phenylalanyl-D-glucose and L-phenylalanyl-lactose esters were synthesized enzymatically using two lipases viz., Rhizomucor miehei lipase (RML) and porcine pancreas lipase (PPL) and tested for their potential as inhibitors of angiotensin converting enzyme (ACE) in vitro. The esters exhibited concentration related ACE inhibitory activity. The potency of the various esters measured in terms of IC50 values were as follows: L-phenylalanyl-D-glucose, IC50-0.121 mM (mixture of five diastereomeric esters: 6-O-24.1%; 3-O-23.3%; 2-O-19.2%; 2,6-di-O-16.6% and 3,6-di-O-16.8% from the total yield of 92.4%); L-phenylalanyl-lactose, IC50-0.229 mM (mixture of three diastereomeric esters: 6-O-42.1%; 6'-O-30.9%; and 6,6'-di-O-27.0% from the total yield of 50.58%); alanyl-D-glucose, IC50-0.23 mM (mixture of five diastereomeric esters: 6-O-46.7%; 3-O-11.5%; 2-O-19.9%; 2,6-di-O-6.6% and 3,6-di-O-15.3% from the total yield of 26.5%) and L-valyl-D-glucose, IC50-0.396 mM (mixture of five diastereomeric esters: 6-O-32.4%; 3-O-26.5%; 2-O-26.4%; 2,6-di-O-8.8% and 3,6-di-O-5.9% from the total yield of 68.2%). These in vitro data suggest a potential therapeutic role for the aminoesters of carbohydrates as inhibibitors of ACE.

摘要

使用两种脂肪酶，即米黑根毛霉脂肪酶（RML）和猪胰脂肪酶（PPL），酶法合成了L-丙氨酰-D-葡萄糖、L-缬氨酰-D-葡萄糖、L-苯丙氨酰-D-葡萄糖和L-苯丙氨酰乳糖酯，并对它们在体外作为血管紧张素转换酶（ACE）抑制剂的潜力进行了测试。这些酯表现出与浓度相关的ACE抑制活性。以IC50值衡量的各种酯的效力如下：L-苯丙氨酰-D-葡萄糖，IC50为0.121 mM（五种非对映体酯的混合物：6-O-24.1%；3-O-23.3%；2-O-19.2%；2,6-二-O-16.6%和3,6-二-O-16.8%，占总产率92.4%）；L-苯丙氨酰乳糖，IC50为0.229 mM（三种非对映体酯的混合物：6-O-42.1%；6'-O-30.9%；6,6'-二-O-27.0%，占总产率50.58%）；丙氨酰-D-葡萄糖，IC50为0.23 mM（五种非对映体酯的混合物：6-O-46.7%；3-O-11.5%；2-O-19.9%；2,6-二-O-6.6%和3,6-二-O-15.3%，占总产率26.5%）和L-缬氨酰-D-葡萄糖，IC50为0.396 mM（五种非对映体酯的混合物：6-O-32.4%；3-O-26.5%；2-O-26.4%；2,6-二-O-8.8%和3,6-二-O-5.9%，占总产率68.2%）。这些体外数据表明，碳水化合物的氨基酯作为ACE抑制剂具有潜在的治疗作用。