74 アンスラ-γ-ピロン型抗腫瘍性抗生物質の構造決定(ポスター発表の部)

概要

論文の詳細を見る
In the course of our investigation of antitumor microbial metabolites which interact with DNA, we isolated 1, 3-5 and 7 from the fermentation broth of Streptomyces. These compounds showed antibacterial activity, antitumor activity in vivo, and caused single strand breakes in supercoiled plasmid DNA in vitro. Their physico-chemical data gave us the following information. The molecular formurae are C_<25>H_<18>O_9 for 1, C_<27>H_<24>O_9 for 5 and C_<29>H_<26>O_<11> for 7. All of them have fused aromatic rings and epoxids. 1 has 5, 8-dihydroxy naphthoquinone moiety in the chromophore. 1 and 3-5 have carboxylic acid groups. Their whole structures were determined based on analysis of the spectroscopic data, mainly of 2D NMR (HMQC, HMBC etc.). In order to improve instability and poor solubility, 1 was converted into the metyl ester(2) and analysed. 3 and 4 had the same fused ring chromophore as that of 5, then the difference among them were in the sidechain moieties, which were confirmed by comparison of the NMR spectra. Degradation product of 5 in DMSO was determined to be the decarboxylate (6). 1, 3-5 and 7 possesses the same anthra-γ-pyrone skeleton as the pluramycin-group antitumor antibiotics. However, 1 and 3-5 have a carboxyl group on C-13, no C-glycosylated sugar on the D ring, and 7 has no aminosugar on the D ring but a deoxyketose on C-9. So, 1, 3-5 and 7 are distinctly different from them.
天然有機化合物討論会の論文
1991-09-07