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2-亚甲基-β-丙氨酸甲酯:一种源自海绵动物海绵窦状海绵(Fasciospongia cavernosa)的有毒氨基酸。

2 Methylene-beta-alanine methyl ester: a toxic amino acid originating from the sponge Fasciospongia cavernosa.

作者信息

Neeman I

出版信息

Arch Toxicol Suppl. 1983;6:258-60. doi: 10.1007/978-3-642-69083-9_47.

DOI:10.1007/978-3-642-69083-9_47
PMID:6414438
Abstract

N-acyl-2-methylene-beta-alanine methyl esters (A) are the main lipidic compounds in the sponge Fasciospongia cavernosa. These compounds were isolated and after methanolysis--2 methylene-beta-alanine methyl esters (AA) and free fatty acid methyl esters were obtained. The interaction of A and AA with the thiol group of cysteine was detected by Ellman's procedure. Both A and AA interact with the thiol group of cysteine in the pH range of 6.0-8.0. Both compounds were found to be strong inhibitors of glyceraldehyde triphosphate dehydrogenase (TPD) from rabbit muscle. The inhibitory effect of A and AA decreases upon addition of beef extract and other protein mixtures containing thiol groups. E. coli growth on a synthetic medium was inhibited by compound AA. Resistant E. coli varieties were isolated by techniques of enrichment cultures. Some of these resistant varieties were shown, by cross-feeding with cysteine dependent E. coli varieties, to excrete cysteine and cysteine derivatives.

摘要

N-酰基-2-亚甲基-β-丙氨酸甲酯(A)是海绵Fasciospongia cavernosa中的主要脂质化合物。这些化合物被分离出来,经过甲醇解后得到2-亚甲基-β-丙氨酸甲酯(AA)和游离脂肪酸甲酯。通过埃尔曼方法检测了A和AA与半胱氨酸硫醇基团的相互作用。A和AA在pH值6.0 - 8.0范围内均与半胱氨酸的硫醇基团相互作用。发现这两种化合物都是兔肌肉甘油醛三磷酸脱氢酶(TPD)的强抑制剂。加入牛肉提取物和其他含硫醇基团的蛋白质混合物后,A和AA的抑制作用减弱。化合物AA抑制了大肠杆菌在合成培养基上的生长。通过富集培养技术分离出了抗药性大肠杆菌变种。通过与依赖半胱氨酸的大肠杆菌变种交叉喂养,发现其中一些抗药变种会分泌半胱氨酸和半胱氨酸衍生物。

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