Yamamoto S, Okujo N, Fujita Y, Saito M, Yoshida T, Shinoda S
Faculty of Pharmaceutical Sciences, Okayama University.
J Biochem. 1993 May;113(5):538-44. doi: 10.1093/oxfordjournals.jbchem.a124079.
From low-iron cultures of Vibrio fluvialis AQ 0012, two new compounds with siderophore activity were purified by XAD-7 adsorption followed by preparative TLC. Norspermidine and 2,3-dihydroxybenzoic acid were identified as constituents common to both compounds by GC-MS analyses of their acid hydrolytic products. In addition, L-threonine was identified in the hydrolysate of one compound, named fluvibactin. Based on high magnetic NMR analyses, the structure of fluvibactin was established as N4-[2-(2,3-dihydroxy-phenyl)-trans-5-methyl-2-oxazoline-4-yl]carboxy-N1, N7- bis-(2,3-dihydroxybenzoyl)-norspermidine, and that of the other compound as N1,N7-bis-(2,3-dihydroxybenzoyl)-norspermidine. The structures were supported by fast atom bombardment mass spectrometry. Both of the purified compounds restored growth inhibition of the producer strain and V. cholerae Non-O1 induced by ethylenediamine di-(o-hydroxyphenylacetic acid), a potent synthetic chelating agent of ferric iron.
从河流弧菌AQ 0012的低铁培养物中，通过XAD - 7吸附然后制备薄层层析法纯化出两种具有铁载体活性的新化合物。通过对其酸水解产物的气相色谱 - 质谱分析，确定亚精胺和2,3 - 二羟基苯甲酸是这两种化合物共有的成分。此外，在一种名为fluvibactin的化合物的水解产物中鉴定出L - 苏氨酸。基于高分辨核磁共振分析，将fluvibactin的结构确定为N4 - [2 - (2,3 - 二羟基 - 苯基) - 反式 - 5 - 甲基 - 2 - 恶唑啉 - 4 - 基]羧基 - N1,N7 - 双 - (2,3 - 二羟基苯甲酰基) - 亚精胺，另一种化合物的结构为N1,N7 - 双 - (2,3 - 二羟基苯甲酰基) - 亚精胺。这些结构通过快原子轰击质谱得到了证实。两种纯化的化合物都恢复了由乙二胺二 - (邻羟基苯乙酸)（一种有效的三价铁合成螯合剂）诱导的生产菌株和霍乱弧菌非O1菌株的生长抑制。
