84 淡水産藍藻より得られたセリンプロテアーゼ阻害物質の構造(ポスター発表の部)

概要

論文の詳細を見る
In the course of our studies of protease inhibitors from microalgae, freshwater blue-green algae showed potent serine protease inhibitory activities. Here, we describe the isolation and structure elucidation of nostopeptin A, a chymotrypsin and elastase inhibitor from Nostoc minutum and radiosumin, a trypsin inhibitor from Plectonema radiosum. Nostoc minutum (NIES-26) was obtained from the National Institute for Environmental Studies, Japan. The methanol extract of lyophilized alga was subjected to solvent partition, ODS column chromatography, followed by ODS HPLC to obtain nostopeptin A (1). Molecular formula of 1 was decided as C_<48>H_<74>N_8O_<12> from HRFABMS and NMR data. Amino acid analysis of the acid hydrolyzate gave Glu, Ile and Leu. ^1H-^1H COSY, HOHAHA, HMQC and HMBC data showed the presence of Leu, Gln, N-MeTyr, 3-amino-6-hydroxy-2-piperidone, butyric acid, 3-hydroxy-4-methylproline and two Ile. Interpretation of HMBC and ROESY spectra revealed the sequence of 1. The stereochemistries of the usual amino acids were assigned to be L by the chiral GC analysis of the derivatives of the hydrolyzate. The 80% methanol extract of lyophilized Plectonema radiosum (NIES-515) was subjected to solvent partition, ODS column chromatography, followed by ODS HPLC to yield radiosumin (2). Molecular formula of 2 was established to be C_<22>H_<32>N_4O_5 by the HRFABMS and NMR data. ^1H-^1H COSY, HMQC and HMBC spectra showed the presence of two amino acid residues, 2-amino-3-(4-amino-2-cyclohexen-1-ylidene)propionic acid and 2-amino-3-(4-amino-2-cyclohexylidene)propionic acid, and two acetyl groups. Further analyses of HMBC and NOESY spectra revealed the structure of 2. The stereochemistries were inspected by the chiral GC analyses of the derivatives of degradation products of 2. The IC_<50> of 1 against elastase and chymotrypsin was 1.3 and 1.4μg/mL, respectively. The IC_<50> of 2 against trypsin was 0.14μg/mL.
天然有機化合物討論会の論文
1993-09-10

84 淡水産藍藻より得られたセリンプロテアーゼ阻害物質の構造(ポスター発表の部)

スポンサーリンク

概要

著者

関連論文

スポンサーリンク