63 藍藻Microcystis aeruginosaより得られたトリプシン阻害物質の構造(ポスター発表の部)

概要

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Microalgae are rich sources of structurally-novel and biologically-active compounds. In the course of our screening program of enzyme inhibitors from microalgae, we found potent trypsin-inhibitory activity in the extract of cultured freshwater blue-green alga Microcystis aeruginosa. Microcystis aeruginosa (NIES-100) was obtained from the National Institute for Environmental Studies, Japan. The 80% methanol extract of lyophilized alga (248g) harvested from 810L culture was subjected to solvent partition, DEAE, SiO_2 and ODS column chromatography, finally to reversed-phase HPLC using ODS column to obtain trypsin inhibitors named micropeptin A (1) and micropeptin B (2). Molecular formula of micropeptin A was decided as C_<49>H_<78>N_8O_<13> from HRFABMS and NMR data. Amino acid analysis of the acid hydrolyzate gave Thr, Glu, Val, Leu, Lys and N-MeTyr. ^1H-^1H COSY, HOHAHA, HMQC-HOHAHA and HMBC spectra showed the presence of these six amino acids, octanoic acid and 3-amino-6-hydroxy-2-piperidone. Interpretation of HMBC and ROESY spectra revealed the cyclic structure of 1. The structure of 2 only differs from 1 in having hexanoic acid in place of octanoic acid. Chiral GC and LC analyses indicated all the usual amino acids to be in L-form. The IC_<50> of 1 against trypsin and plasmin was 0.071; 0.026μg/mL, respectively.
天然有機化合物討論会の論文
1992-09-10