Structures of two polyamine-containing catecholate siderophores from Vibrio fluvialis.
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.
Yamamoto
S
S
Faculty of Pharmaceutical Sciences, Okayama University.
Okujo
N
N
Fujita
Y
Y
Saito
M
M
Yoshida
T
T
Shinoda
S
S
D002396:Catechols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D003470:Culture Media; D004492:Edetic Acid / Q000031:analogs & derivatives / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D062385:Hydroxybenzoates / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D017262:Siderophores / Q000737:chemistry* / Q000494:pharmacology; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013095:Spermidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013912:Threonine / Q000032:analysis; D014733:Vibrio / Q000737:chemistry* / Q000187:drug effects / Q000254:growth & development; D014734:Vibrio cholerae / Q000187:drug effects / Q000254:growth & development
D002396:Catechols; D003470:Culture Media; D062385:Hydroxybenzoates; D017262:Siderophores; C082368:fluvibactin; D013912:Threonine; C026058:EDDA; C009135:2,3-dihydroxybenzoic acid; C082369:N(1),N(7)-bis(2,3-dihydroxybenzoyl)norspermidine; D004492:Edetic Acid; D013095:Spermidine