P-39 魚病細菌Pasteurella piscicidaに有効な新規抗生物質テトロデカマイシンの構造(ポスター発表の部)

概要

論文の詳細を見る
In the course of our screening program for novel antimicrobial antibiotics against Pasteurella piscicida, we have isolated new antibiotics, tetrodecamycin (1) and weakly active dihydrotetrodecamycin (2) from a culture broth of a streptomycete. The MICs of 1 were 6.25-12.5μg/ml and 1.56-6.25μg/ml against Gram-positive bacteria and two strains of P.piscicida, respectively. The molecular formula of 1 was determined to be C_<18>H_<22>_O_6 by HRFAB-MS and ^<13>C-NMR spectral data of 1 and acetyl derivative (3). The planar structure of 1 was elucidated by various NMR spectral analyses of 1 and 3, except for an acyl tetronic acid alkyl ether moiety. This moiety was established by comparison of its ^<13>C chemical shifts with those of gregatin B. The IR and UV spectral data of 1 also suggested the presence of the acyl tetronic acid moiety. The structure of 2 was elucidated by comparison with the spectral data of 1. The relative stereochemistry of 2 was determined by X-ray crystallography. The stereochemistry of 1 was as same as 2, because 1 was converted into 2 by catalytic reduction. The absolute stereochemistry was determined by modified Mosher's method applied to secondary alcohol of 1. The structure-activity relationships of the ester derivatives of 1 were also described.
天然有機化合物討論会の論文
1994-09-20