REVISED STRUCTURE FOR THE PHENAZINE ANTIBIOTIC FROM PSEUDOMONAS-FLUORESCENS 2-79 (NRRL B-15132)
REVISED STRUCTURE FOR THE PHENAZINE ANTIBIOTIC FROM PSEUDOMONAS-FLUORESCENS 2-79 (NRRL B-15132)
复制标题
DOI：
10.1128/aac.31.12.1967
复制
发表时间：
1987-12-01
影响因子：
4.9
通讯作者：
WARREN, RFO
中科院分区：
文献类型：
--
作者：
BRISBANE, PG;JANIK, LJ;WARREN, RFO
一种吩嗪类抗生素（mp，243至244 ℃），从荧光假单胞菌2-79（NRRL B-15132）的培养物中以134 μ g/ml的产率分离的C）在其所有测量的物理化学（熔点、UV和红外光谱、以及气相色谱-质谱数据）和生物学性质上与合成的吩嗪-1-羧酸没有区别。Gurusiddaiah等人（S. Gurusiddaiah，D. M. Weller，A. Sarkar和R. J. Cook，Antimicrob.探员Chemother 29：488-495，1986）将二聚吩嗪结构赋予具有从相同细菌菌株获得的明显相似性质的抗生素。对从D. M. Weller用合成的吩嗪-1-羧酸和本研究的天然产物确定，所有三种样品在每种方法的实验误差内无法区分。未获得支持存在生物活性二聚体物质的证据。吩嗪-1-羧酸的pKa为4.24 ±。0.01（25度）C; I = 0.09），并且其羧酸根阴离子与活性的不带电荷的羧酸物质相比没有显示出可检测的抗微生物活性。这些数据表明，吩嗪-1-羧酸可能不是一种有效的生物控制剂，在环境中的pH值大于7的植物病原体。
A phenazine antibiotic (mp, 243 to 244.degree. C), isolated in a yield of 134 .mu.g/ml from cultures of Pseudomonas fluorescens 2-79 (NRRL B-15132), was indistinguishable in all of its measured physicochemical (melting point, UV and infrared spectra, and gas chromatography-mass spectrometry data) and biological properties from synthetic phenazine-1-carboxylic acid. Gurusiddaiah et al. (S. Gurusiddaiah, D. M. Weller, A. Sarkar, and R. J. Cook, Antimicrob. Agents Chemother. 29:488-495, 1986) atrributed a dimeric phenazine structure to an antibiotic with demonstrably similar properties obtained from the same bacterial strain. Direct comparison of the physicochemical properties of the authenic antibiotic obtained from D. M. Weller with synthetic phenazine-1-carboxylic acid and with the natural product from the present study established that all three samples were indistinguishable within the experimental error of each method. No evidence to support the existence of a biologically active dimeric species was obtained. Phenazine-1-carboxylic acid has a pKa of 4.24 .+-. 0.01 (25.degree. C; I = 0.09), and its carboxylate anion shows no detectable antimicrobial activity compared with the active uncharged carboxylic acid species. These data suggest that phenazine-1-carboxylic acid is probably not an effective biological control agent for phytopathogens in environments with a pH greater than 7.