Abstract
A novel siderophore, called acinetobactin, with both catecholate and hydroxamate functional groups was isolated from low-iron cultures of Acinetobacter baumannii ATCC 19606. The structure was elucidated by chemical degradation, fast-atom bombardment mass spectrometry and 1H and 13C NMR spectroscopy. Acinetobactin was composed of ω-N-hydroxyhistamine, threonine and 2,3-dihydroxybenzoic acid, the last two components forming an oxazoline ring. Acinetobactin was structurally related to anguibactin, a plasmid-encoded siderophore of Vibrio anguillarum. The only difference was that acinetobactin possessed an oxazoline ring instead of a thiazoline ring. Four of 12 other clinical A. baumannii strains examined produced acinetobactin, indicative of strain-to-strain variation in the ability to produce acinetobactin. In addition, a relatively small amount of acinetobactin was also detected in A. haemolyticus ATCC 17906.
Similar content being viewed by others
Abbreviations
- COSY :
-
chemical shift correlation spectroscopy
- DHBA :
-
2,3-dihydroxybenzoic acid
- EDDA :
-
ethylenediamine-di(o-hydroxyphenylacetic acid)
- FAB :
-
fast-atom bombardment
- GC-MS :
-
gas chromatography-mass spectrometry
References
Actis LA, Tolmasky ME, Crosa LM, Crosa JH (1993) Effect of iron limiting conditions on growth of clinical isolates of Acinetobacter baumannii. J Clin Microbiol 31:2812–2815
Andrus CR, Walter M, Crosa JH, Payne SM (1983) Synthesis of siderophores by pathogenic Vibrio species. Curr Microbiol 9: 209–214
Arnow LE (1937) Colorimetric determination of the components of 3,4-dihydroxyphenylalanine-tyrosine mixtures. J Biol Chem 228:531–537
Braum V, Winkelmann G (1987) Microbial iron transport: structure and function of siderophores. Prog Clin Biochem Med 5: 67–99
Crosa JH (1989) Genetics and molecular biology of siderophoremediated iron transport in bacteria. Microbiol Rev 53:517–530
Csáky TZ (1948) On the estimation of bound hydroxylamine in biological materials. Acta Chem Scand 2:450–454
Dell A, Hider RC, Barber M, Bordoli RS, Segdwick RD, Tyler AN, Neilands JB (1982) Field-desorption and fast-atom bombardment mass spectrometry of hydroxamate-containing siderophores. Biomed Mass Spectrom 9:158–161
Echenique JR, Arient H, Tolmasky ME, Read RR, Staneloni RJ, Crosa JH, Actis LA (1992) Characterization of a high-affinity iron transport system in Acinetobacter baumannii. J Bacteriol 174:7670–7679
Feistner GJ, Beaman BL (1987) Characterization of 2,3-dihydroxybenzoic acid from Nocardia asteroides GUH-2. J Bacteriol 169: 3982–3987
Gibson F, Magrath DI (1969) The isolation and characterization of a hydroxamic acid (aerobactin) formed by Aerobacter aerogenes 62-I. Biochim Biophys Acta 192:175–184
Griffiths E (1987) Iron in biological systems. In: Bullen JJ, Griffiths E (eds) Iron and infection. John Wiley, Chichester, pp 1–25
Jalal MAF, Hossain MB, Helm D van der, Sanders-Loehr J, Actis LA, Crosa JH (1989) Structure of anguibactin, a unique plasmid-related bacterial siderophore from the fish pathogen Vibrio anguillarum. J Am Chem Soc 111:292–296
Mahy N, Gelpi E (1977) Gas chromatographic separation of histamine and its metabolites. J Chromatogr 130:237–242
Miles AA, Khimji PL (1975) Enterobacterial chelators of iron: their occurrence, detection, and relation to pathogenicity. J Med Microbiol 8:477–490
Neilands JB (1981) Microbial iron compounds. Ann Rev Biochem 50:715–731
Neilands JB, (1983) Siderophores. Adv Inorg Biochem 5:137–166
Okujo N, Saito M, Yamamoto S, Yoshida T, Miyoshi S, Shinoda S (1994a) Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus. BioMetals 7:109–116
Okujo N, Sakakibara Y, Yoshida T, Yamamoto S (1994b) Structure of acinetoferrin, a new citrate-based dihydroxamate siderophore from Acinetobacter haemolyticus. BioMetals 7:170–176
Ong, SA, Peterson T, Neilands JB (1979) Agrobactin, a siderophore from Agrobacterium tumefaciens. J Biol Chem 254: 1860–1865
Payne SM (1988) Iron and virulence in the family Enterobacteriaceae. Crit Rev Microbiol 36:285–309
Persmark M, Pittman P, Buyer JS, Schwyn B, Gill PR, Neilands JB (1993) Isolation and structure of rhizobactin 1021, a siderophore from the alfalfa symbiot Rhizobium meliloti 1021. J Am Chem Soc 115:3950–3956
Schwyn B, Neilands JB (1987) Universal chemical assay for the detection and determination of siderophores. Anal Biochem 160:47–56
Smith AW, Freemans S, Minett WG, Lambert PA (1990) Characterization of a siderophore from Acinetobacter calcoaceticus. FEMS Microbiol Lett 70:29–32
Snow GA (1970) Mycobactins: iron-chelating growth factors from mycobacteria. Bacteriol Rev 34:99–125
Towner KJ, Bergogne-Bérézin E, Fewson CA (1991) The biology of Acinetobacter. Taxonomy, clinical importance, molecular biology, physiology, industrial relevance. Plenum Press, New York
Weinberg ED (1978) Iron and infection. Microbiol Rev 42:45–66
Yamamoto S, Kiyama S, Watanabe Y, Makita M (1982) Practical gas-chromatographic method for the determination of amino acids in human serum. J Chromatogr 233:39–50
Yamamoto S, Okujo N, Fujita Y, Saito M, Yoshida T, Shinoda S (1993) Structures of two polyamine-containing catecholate siderophores from Vibrio fluvialis. J Biochem 113:538–544
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Yamamoto, S., Okujo, N. & Sakakibara, Y. Isolation and structure elucidation of acinetobactin., a novel siderophore from Acinetobacter baumannii . Arch. Microbiol. 162, 249–254 (1994). https://doi.org/10.1007/BF00301846
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00301846