Structure of acinetoferrin, a new citrate-based dihydroxamate siderophore fromAcinetobacter haemolyticus

Abstract

From low-iron cultures of Acinetobacter haemolyticus ATCC 17906, a new hydroxamate siderophore was purified by XAD-7 adsorption followed by preparative thin layer chromatography. The siderophore, named acinetoferrin, released citric acid, 1,3-diaminopropane and (E)-2-octenoic acid upon hydrolysis with HCI, reductive hydrolysis with HI and oxidation with periodate, respectively. Structure elucidation by a combination of NMR spectroscopy and positive fast atom bombardment mass spectrometry revealed that acinetoferrin is a derivative of citric acid, both of its terminal carboxyl groups being symmetrically amide-linked with the 1-amino-3-(N-hydroxy-N-2-octenylamino)propane residues. The (E)-2-octenoic acid is novel as a component of the siderophores.

Structure and membrane affinity of a suite of amphiphilic siderophores produced by a marine bacterium

“…The mycobactins have significantly longer fatty acids and are cell-associated, whereas the carboxymycobactins are secreted extracellularly. The iron accu- (27), and mycobactin S (25). Some bacteria, designated with a star ( * ) next to their name, make suites of siderophores like the amphibactins.…”

“…Other amphiphilic siderophores include the ornibactins, produced by Burkholderia (Pseudomonas) cepacia; corrugatin, produced by Pseudomonas corrugata; acinetoferrin, produced by Acinetobacter haemolyticus; rhizobactin 1021, produced by Sinorhizobium meliloti; and the carboxymycobactins, produced by mycobacteria, all of which are produced and secreted into the growth medium by terrestrial bacteria. With the exception of the ornibactins and carboxymycobactins, these are all single siderophores as opposed to a suite of siderophores that vary in the nature of the fatty acid tail (25)(26)(27)(28)(29)(30). Mycobacteria, as well as other high G ϩ C Gram-positive bacteria, also produce the only structurally characterized family of siderophores to date that are associated with the bacterial membrane and are not secreted into the growth medium.…”

Isolation and characterization of the siderophore N-deoxyschizokinen from Bacillus megaterium ATCC 19213

“…Besides schizokinen, other citrate-based dihydroxamate siderophores include aerobactin (Gibson & Magrath 1969), arthrobactin (Linke et al 1972), nannochelin A and C (Kunze et al 1992), and acinetoferrin (Okujo et al 1994). They are all symmetrically substituted around the citric acid residue.…”

Characterization and Fungal Inhibition Activity of Siderophore from Wheat Rhizosphere Associated Acinetobacter calcoaceticus Strain HIRFA32

“…synthesis is intensely studied till date only in clinical strains of A. baumannii and A. haemolyticus. These clinical strains of Acinetobacter are known to produce two siderophores; namely acinetobactin and acinetoferrin, which have been characterized from A. baumannii and A. haemolyticus, respectively [20][21][22]. Thus, the objective of this investigation was to purify and perform structural characterization of siderophore from a strain of A. calcoaceticus previously isolated from rhizosphere of wheat.…”