Structure and Characterization of Isopyoverdin from Pseudomonas putida BTP1 and Its Relation to the Biogenetic Pathway Leading to Pyoverdins

Abstract

Pyoverdin type siderophores produced by six fluorescent Pseudomonas strains isolated from different rhizospheres were purified and characterized. The purified ferri-pyoverdins were tested for their ability to promote the growth of other strains grown under iron deficiency conditions. Only the one obtained from Pseudomonas putida BTP1 did not act as a growth promoter. The structure of the BTP1 siderophore was elucidated by spectroscopic methods and degradation studies. It turned out that it contains a chromophore which differs from the one typical for pyoverdins insofar as it carries the carboxyl group in 3- rather than in 1-position ((3S)-5-amino-1,2-dihydro-8,9-dihydroxy-3 H -pyrimido[1,2 a]quinoline-3-carboxylic acid). The amino group of the chromophore is substituted with the 5-carboxyl group of ʟ-glutamic acid and its carboxyl group with the N -terminus of the peptide ʟ -A sp -ʟ -A la-ʟ -Asp - ᴅ-N5- Ac - N5- OH - Orn - ʟ - Ser - ʟ - ᴄ - N5- OH - Orn . This isopyoverdin fits into the biogenetic scheme which postulates ferribactins as the precursors of pyoverdins

Production and Comparison of Peptide Siderophores from Strains of Distantly Related Pathovars of Pseudomonas syringae and Pseudomonas viridiflava LMG 2352

“…This is due to the quinoline chromophore found in all pyoverdins (2). Several pyoverdin precursors (2,4,16,31,32) or by-products (11,16,17) differ in chromophore structure and spectral characteristics. The spectral characteristics of the siderophore produced by P. syringae and P. viridiflava resemble the spectral characteristics of pyoverdins, but the siderophore differs from all of these molecules (Fig.…”

Isolation of an N-alkylated Benzylamine Derivative from Pseudomonas putida BTP1 as Elicitor of Induced Systemic Resistance in Bean

“…The strain has developed an efficient pyoverdine-mediated iron acquisition system (Jacques et al 1995;Ongena et al 2001); however, these chromopeptides do not play any role because previous results showed that pyoverdineenriched extracts failed to induce resistance (Ongena et al 2002). The strain has developed an efficient pyoverdine-mediated iron acquisition system (Jacques et al 1995;Ongena et al 2001); however, these chromopeptides do not play any role because previous results showed that pyoverdineenriched extracts failed to induce resistance (Ongena et al 2002).…”

“…Pseudomonas putida BTP1, isolated from barley roots, originally was selected for its specific features regarding pyoverdinemediated iron transport (Jacques et al 1995;Ongena et al 2001). All strains were maintained on Pseudomonas agar F medium (KB; Becton, Dickinson, and Company, Le pont de Claix, France) at 4ºC before experimental use, and stored at -80ºC in cryotubes according to the manufacturer's recommendations (Microbank; Prolab Diagnostic, Richmond Hill, Canada) for long-term conservation.…”

“…BTP1 pyoverdine concentrations in the cell-free supernatants were calculated on the basis of the absorbance at 400 nm using a specific molar extinction coefficient (ε 400nm, pH 7 ) of 2.75 10 4 mol liter -1 cm -1 (Jacques et al 1995). BTP1 pyoverdine concentrations in the cell-free supernatants were calculated on the basis of the absorbance at 400 nm using a specific molar extinction coefficient (ε 400nm, pH 7 ) of 2.75 10 4 mol liter -1 cm -1 (Jacques et al 1995).…”

Pseudomonas

“…The chromophore, identical for all the pyoverdines so far identified, is (lS)-5-amino-2,3-dihydro-8,9-dihydroxy-IH-pyrimido [I,2-a] quinoline-I-carboxylic (Michels et aI., 1991). One exception, however, has been recently described for a strain of P. putida which has a pyoverdine with a carboxylic group attached to the C 3 instead of the C 1 of the quinoline cyclic ring (Jacques et at., 1993(Jacques et at., , 1995.…”