Abstract
In recent years, substances containing iron and showing a broad absorption band, with an absorption maximum between 420 and 440 mμ, have been isolated from cultures of various microorganisms (Bickel et al., 1960a; Prelog, 1963; Keller-Schierlein et al., 1964). Within this group of naturally occurring substances can be found some which display antibiotic properties, whereas others antagonise this antibiotic activity and actually promote the growth of certain micro-organisms. Chemical studies have revealed that all these substances are iron (III)-trihydroxamate complexes. For this reason, Bickel et al. (1960a) designated them collectively as “siderochromes”. Subsequently, Zähner et al. (1962) subdivided them on the basis of their biological properties into the following categories:
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a)
Sideromycins; i.e. siderochromes displaying antibiotic activity.
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b)
Sideramines; i.e. siderochromes which competitively antagonise the antibiotic effect of the sideromycins and which also exert a growth-promoting action on certain micro-organisms.
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c)
Siderochromes whose biological properties are as yet unknown.
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References
Bachmann, E., U. H. Zähner: Stoffwechselprodukte von Actinomyceten. 28. Mitt. Die „in vitro“-Resistenz gegen Ferrimycin. Arch. Mikrobiol. 38, 326 (1961).
Beljanski, M., et M. Beljanski: Sur la formation d’enzymes respiratoires chez un mutant d’Escherichia coli streptomycine-résistant et auxotrophe pour lhémine. Ann. inst. Pasteur. 92, 396 (1957).
Benz, F., and H. Bickel: Personal communication 1965.
Bergmeyer, H. U.: Methoden der enzymatischen Analyse (Glyoxalat, S. 300, Malat, S. 328, Pyruvat, S. 253). Weinheim: Verlag Chemie 1962.
Bickel, H., E. Gäumann, W. Keller-Schierlein, V. Prelog, E. Vischer, A. WETTSTEIN u. H. Zähner: Über eisenhaltige Wachstumsfaktoren, die Sideramine und ihre Antagonisten, die eisenhaltigen Antibiotika Sideromycine. Experientia 16(4), 129 (1960a).
Bickel, H., E. Gäumann, G. Nussberger, P. Reusser, E. Vischer, W. Voser, A. WETTSTEIN U. H. Zähner: Stoffwechselprodukte von Actinomyceten. 25. Mitt. Über die Isolierung und Charakterisierung der Ferrimycine A1 und A2, neuer Antibiotika der Sideromyein-Gruppe. Helv. Chim. Acta 43, 2105 (1960b).
Bickel, H., P. Mertens, V. Prelog, J. Seibl, and A. Walser: The constitution of Ferrimycin A1 IVth Int. Congr. Chemother. 1965 (Abstracts) p. 15.
Boehringer: Glutamat-Oxalacetat-Transaminase „Boehringer“. Biochemica Testcombination „Boehringer”, C. F. Boehringer & Söhne GmbH Mannheim 1962.
Boehringer: Isocitronensäure-Dehydrogenase nach „ Boehringer“, Biochemica Informationen „ Boehringer“, C. F. Boehringer & Söhne GmbH Mannheim 1961.
Boehringer: Ketoglutarsäure-Test. Biochemica Testkombinationen „ Boehringer“, C. F. Boehringer & Söhne GmbH Mannheim 1962.
Boehringer: Lactat-Test. Biochemica Testkombination „ Boehringer“, C. F. Boehringer & Söhne GmbH Mannheim 1962.
Brinberg, S. L., and T. I. Grinyuk: The physiological features of Act. subtropicus in connection with the biosynthesis of the antibiotic Albomycin. Antibiotics UdSSR 4, 534 (1959).
Burnham, F. B.: Bacterial iron metabolism. Investigations on the mechanism of ferrichrome function Arch. Biochem. Biophys. 97, 329 (1962a).
Burnham, F. B.: Personal communication 1962b.
Burnham, F. B., and J. B. Neilands: Studies on the metabolic function of the ferrichrome compounds. J. Biol. Chem. 236(2), 554 (1961).
Coultas, M. K., and D. I. Hutchinson: Metabolism of resistent mutants of Streptococcus faecalis. IV. Use of a biophotometer in growth-curve studies. J. Bacteriol. 84, 393 (1962).
Das, S. K., and G. C. Chatterjee: Pyrithiamine adaptation of Staphylococcus aureus. I. Adaption and carbohydrate utilization. J. Bacteriol. 83, 1251 (1962).
Das, S. K., and G. C. Chatterjee: Pyrithiamine adaptation of Staphylococcus aureus. II. Tricarboxylic acid cycle and related enzymes. J. Bacteriol. 86, 1157 (1963).
Demain, A. L., and D. Hendlin: “Iron transport” compounds as growth stimulators for Microbacterium sp. J. gen. Microbiol. 21, 72 (1959).
Francis, J., H. M. Macturk, J. Madinaveitia, and G. A. Snow: Mycobactin, a growth factor for Mycobacterium johnei. I. Isolation from Mycobacterium phlei. Biochem. J. 55, 596 (1953).
Garibaldi, J. A., and J. B. Neilands: Formation of iron binding compounds by micro-organisms. Nature 177, 526 (1956).
Gause, G. F.: Recent studies on Albomycin, a new antibiotic. Brit. med. 1955, 1177.
Gause, G. F., U. M. G. Brazhnikova: Die Wirkung von Albomycin gegen Bakterien [Russ.]. Novostin. Med., Akad. Med. Nauk S. S. S. R. 23, 3 (1951).
Gäumann, E., E. VISCHER U. H. Bickel: Verfahren zur Herstellung eines neuen Antibiotikums. Deutsche Auslegeschrift DAS 1129, 259 (1951).
Granick, S., and H. Gilder: The porphyrin requirements of Haemophilus influenzae and some functions of the vinyl and propionic acid side chains of heme. J. Gen. Physiol. 30, 1 (1946).
Green, D. E., and H. Beinert: Biological oxidations. Ann. Rev. Biochem. 24, 1 (1955).
Haskell, TH. H., R. H. Bunge, J. C. French, and Qu. R. Bartz: Succinimycin, a new iron-containing antibiotic. J. Antibiotics (Japan), Serie A 16, 67 (1963).
Hesseltine, C. W., C. Pidacks, A. R. Whitehill, N. Bohonos, B. L. Hutchings, and J. H. Williams: Coprogen, a new growth factor for coprophilic fungi. J. Am. Chem. Soc. 74, 1362 (1952).
Hills, G. M.: Aneurin (Vitamin B1) and pyruvate metabolism by Staphylococcus aureus. Biochem. J. 32, 383 (1938).
Hogg, R. W., CH. S. Biswas, and H. P. Broquist: Interference with valine and isoleucine biosynthesis by cyclic hydroxamic acids. J. Bacteriol. 90, 1265 (1965).
Huang, H. T.: Microbial production of amino acids. Progr. Ind. Microbiol. 5, 55 (1964).
Hütter, R.: Zur Systematik der Aktinomyceten. 10. Streptomyceten mit griseus Luftmycel. Giorn. microbiol. 11, 191 (1963).
Jensen, J., u. E. Thofern: Chlorohämin (Ferriporphyrinchlorid) als Bakterienwuchsstoff. I. Z. Naturforsch. 8, 595 (1953a).
Jensen, J., U. E. Thofern: Chlorohämin (Ferriporphyrinchlorid) als Bakterienwuchsstoff. II. Zur Synthese der Hämatinfermente. Z. Naturforsch. 8b, 604 (1953b).
KeLLER-schierlein, W., V. PRELOG U. H. Zähner: Siderochrome. Fortschr. Chem. org. Naturstoffe 22, 279 (1964).
KeLLER-schierlein, W., P. Mertens, V. PRELOG U. A. Walser: Die Ferrioxamine A1 A2 und D2. Helv. Chim. Acta 48, 710 (1965).
Kinoshita, SH.: Amino acids. From biochemistry of industrial micro-organisms, p. 206. London and NewYork: Academic Press 1963.
Knüsel, F., and J. Nüesch: Mechanism of action of sideromycins. Nature 206, 675 (1965).
Kornberg, H. L.: Anaplerotic sequences in microbial metabolism (1). Angew. Chem. (internat, edit.) 4, 558 (1965).
Krysin, E. P., u. N. A. Poddubnaya: Chemische Untersuchung der Struktur des Albomycin. IV. Bestimmung der Aminosäurezusammensetzung und Umwandlungen der Albomycin-Fraktionen. Zhurn. Obshchei Khim. 33, 1370 (1963).
Kuehl, F. A., M. N. Bishop, L. Chaiet, and K. Folkers: Isolation and some chemical properties of grisein. J. Am. Chem. Soc. 73, 1770 (1951)
Lascelles, J.: An assay of iron protoporphyrin based on the reduction of nitrate by a variant strain of Staphylococcus aureus; synthesis of iron protoporphyrin by suspension of Rhodopseudomonas spheroides. J. Gen. Microbiol. 15, 404 (1956).
Lascelles, J.: Synthesis of tetrapyrroles by micro-organisms. Phys. Rev. 41, 417 (1961).
Lochhead, A. G., M. O. Burton, and R. H. Thexton: A bacterial growth factor synthesized by a soil bacterium. Nature 170, 282 (1952).
Lochhead, A. G., S. Kramer, and A. Goldberg: Quantitative measurement of the iron incorporating enzyme in relation to marrow cells and liver tissue in the rabbit. Brit. J. Haemat. 9, 39 (1963).
Morrison, N. E., A. D. Antoine, and E. E. Dewbrey: Synthetic metal chelators which replace the natural growth-factor requirements of Arthrobacter terregens. J. Bacteriol. 89, 1630 (1965).
Neilands, J. B.: A crystalline organo iron compound from the fungus Ustilago spaerogena. J. Am. Chem. Soc. 74, 4846 (1952).
Neilands, J. B.: Some aspects of microbial iron metabolism. Bacteriol. Rev. 21, 101 (1957).
Okami, Y.: Studies on the characteristic of antibiotic Streptomyces. III. Characteristices of grisein producing strains. J. Antibiotics (Japan) 3, 93 (1950).
Page, R. M.: The effect of nutrition on growth and sporulation of Pilobolus. Am. J. Bot. 39, 731 (1952).
Porra, R. J., and O. T. G. Jones: Studies on ferrochelatase 1. Assay and properties of ferrochelatase from a pig-liver mitochondrial extract. Biochem. J. 87, 181 (1963a).
Porra, R. J., and O. T. G. Jones: Studies on ferrochelatase 2. An investigation of the role of ferrochelatase in the biosynthesis of various haem prosthetic groups. Biochem. J. 87, 186 (1963b).
Prelog, V.: Iron-containing compounds in Micro-organisms Symposium Iron-Metabolism, Aix-en-Provence. Berlin-Göttingen-Heidelberg: Springer 1963.
Ramsey, H. H., and C. E. Lankford: Stimulation of growth initiation by heat degradation products of glucose. J. Bacteriol. 72, 511 (1956).
Reynolds, D. M., A. Schatz, and S. A. Waksman: Grisein, a new antibiotic produced by a strain of Streptomyces griseus. Proc. Soc. Exptl. Biol. Med. 64, 50 (1947).
Reynolds, D. M., and S.A. Waksman: Grisein, an antibiotic produced by certain strains of Streptomyces griseus. J. Bacteriol. 55, 739 (1948).
Robbinson, F. A.: The vitamin B complex. NewYork: John Wiley & Sons. Inc. 1951.
Sackmann, W., P. Reusser, L. Neipp, F. Kradolfer, and F. Gross: Ferrimycin A, a new iron-containing antibiotic. Antibiotics & Chemotherapy 12, 34 (1962).
Schopfer, W. H.: La pyrithiamine comme antivitamine B1 Colloque internat, sur les Antivitamines, Lyon. Bull. soc. chim. biol. 30, 940 (1948).
Seargeant, T. P., C. E. Lankford, and R. W. Traxler: Initiation of growth of Bacillus species in a chemically defined medium. J. Bacteriol. 74, 728 (1957).
Sensi, P., and M. T. Timbal: Isolation of two antibiotics of the grisein and albomycin groups. Antibiot. & Chemotherapy 9, 160 (1958).
Sevcik, V.: Antibiotica aus Actinomyceten, 647 S. Jena: VEB Gustav Fischer 1963.
Snow, G. A.: the significance of its iron complex. Biochem. J. 94, 160 (1965).
Stapley, E. O., and R. E. Ormond: Similarity of albomycin and grisein. Science 125, 587 (1957).
Strasters, K. C., and K. C. Winkler: Carbohydrate metabolism of Staphylococcus aureus. J. Gen. Microbiol. 33, 213 (1963).
Thofern, E.: Über Synthese, Struktur und Funktion bakterieller Haeminsysteme. Ergeb. Mikrobiol. 34, 213 (1961).
Thrum, H.: Eine neue Methode zur Isolierung der Antibiotika vom Grisein-Typ. Naturwissenschaften 44, 561 (1957).
Townsley, P. M.: The iron and porphyrin metabolism of Micrococcus lysodeikticus. Doctoral dissertation. Berkeley: University of California, 1956.
Tsukiura, H., M. Okanishi, T. Ohmori, H. Koshiyama, T. Miyaki, H. Kitazima, and H. Kawaguchi: Daunomycin, a new antibiotic. J. Antibiotics (Japan), Ser. A 17, 39 (1964).
Turkova, J., O. Mikes, and F. Sorm: Isolation of the biologically active component albomycin in pure form and its thermal degradation. Antibiotiki 7, 878 (1962).
Umezawa, H., S. Hayano, and Y. Ogata: Studies on an antibiotic substance of Streptomyces griseus, Grisein. J. Antibiotics (Japan), Ser. B 2, 104 (1949).
Warren, R. A. J., and J. B. Neilands: Mechanism of microbial catabolism of Ferrichrome A. J. Biol. Chem. 240, 255 (1965).
Weisel, P., and P. J. Allen: Abstr. Inst. Biol. Sci. Meeting. Minneapolis, September 1951.
Wolin, H. L., and H. B. Naylor: Basic nutritional requirements of Micrococcus lysodeikticus. Bacteriol. Proc. 55th General Meeting 1955, 47.
Yamada, SH., and H. Kawaguchi: Pharmacological studies on Danomycin, a new antibiotic. J. Antibiotics (Japan), Ser. A 17, 48 (1964).
Zähner, H., R. Hütter u. E. Bachmann: Zur Kenntnis der Sideromycinwirkung. Arch. Mikrobiol. 36, 325 (1960).
Zähner, H., E. Bachmann, R. Hütter u. J. Nüesch: Sideramine, eisenhaltige Wachstumsfaktoren aus Mikroorganismen. Path. Mikrobiol. 25, 708 (1962)
Zähner, H.: Antibiotica in der Mikrobiologie. Naturw. Rundschau 17, 391 (1964)
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Nüesch, J., Knüsel, F. (1967). Sideromycins. In: Gottlieb, D., Shaw, P.D. (eds) Mechanism of Action. Antibiotics, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46051-7_41
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