Ojika Makoto, Inukai Yasutaka, Kito Yuko, Hirata Masayuki, Iizuka Takashi, Fudou Ryosuke
Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
Chem Asian J. 2008 Jan 4;3(1):126-33. doi: 10.1002/asia.200700233.
Marine myxobacteria are rare culture-resistant microorganisms, several strains of which have been identified by research groups in Asia. Paraliomyxa miuraensis, a slightly halophilic myxobacterium discovered in Japan, produces the cyclic hybrid polyketide-peptide antibiotics known as miuraenamides A and B, whose taxonomical and biological characteristics have been reported previously. Herein, we describe the chemical characterization of these two miuraenamides and introduce four new members of the miuraenamide family. We carried out the complete structural analysis of miuraenamides A and B on the basis of NMR spectroscopic analysis and elucidated the absolute configuration of miuraenamide A by chemical derivatization and subsequent use of the modified Mosher method or the Marfey method. Miuraenamides C-F were isolated from the same strain of the bacterium as miuraenamides A and B. The structure-antimicrobial-activity relationships of the six natural metabolites and four chemically derived compounds demonstrated the importance of both the macrocyclic structure and the beta-methoxyacrylate moiety.
海洋粘细菌是罕见的难以培养的微生物，亚洲的研究团队已鉴定出其中的几个菌株。在日本发现的一种轻度嗜盐粘细菌——三浦副粘球菌，能产生环状杂合聚酮肽抗生素，即三浦酰胺A和B，其分类学和生物学特性此前已有报道。在此，我们描述了这两种三浦酰胺的化学特征，并介绍了三浦酰胺家族的四个新成员。我们基于核磁共振光谱分析对三浦酰胺A和B进行了完整的结构分析，并通过化学衍生化以及随后使用改良的莫舍尔法或马尔菲法阐明了三浦酰胺A的绝对构型。三浦酰胺C - F与三浦酰胺A和B分离自同一菌株。这六种天然代谢产物和四种化学衍生化合物的结构 - 抗菌活性关系表明了大环结构和β - 甲氧基丙烯酸酯部分的重要性。
