Paper
2 Methylene-beta-alanine methyl ester: a toxic amino acid originating from the sponge Fasciospongia cavernosa.
Published Jan 1, 1983 · I. Neeman
Archives of toxicology. Supplement. = Archiv fur Toxikologie. Supplement
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Abstract
N-acyl-2-methylene-β-alanine methyl esters (A) are the main lipidic compounds in the sponge Fasciospongia cavernosa. These compounds were isolated and after methanolysis — 2 methylene-β-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.
2 Methylene-beta-alanine methyl ester, found in the sponge Fasciospongia cavernosa, is a toxic amino acid that inhibits rabbit muscle growth and E. coli growth, with resistant E. coli varieties excreting cysteine and cysteine derivatives.
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