Structure of syringotoxin B, a phytotoxin produced by citrus isolates of Pseudomonas syringae pv. syringae.

Fukuchi, Naoyuki; Isogai, Akira; Nakayama, Jiro; Suzuki, Akira

doi:10.1271/bbb1961.54.3377

Cited by 19 publications

(6 citation statements)

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“…Isolate 791 showed atypical characteristic as it utilized L-lactate and did not hydrolyze aesculine (Table 1). All Pss isolates, produced SR and /or other TLP, virulence factors used by some researchers as a marker for identification (Grgurina et al 1996;Fukuchi et al 1990). None of isolates belonging to Psm produced SR, which is in agreement with descriptions by Schaad et al (2001) and Janse (2005).…”

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The use of PCR melting profile for typing of Pseudomonas syringae isolates from stone fruit trees

2009

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Of thirty fluorescent Pseudomonas isolates originating from symptomatic tissues of sweet (Prunus avium) and sour cherry (Prunus cerasus), plum (Prunus domestica), peach (Prunus persica) and apricot (Prunus armeniaca), 23 were identified as P. syringae using LOPAT tests. Further characterization of those isolates by GATTa and L-lactate utilization tests showed that 10 of them belonged to race 1, six to race 2 of P. syringae pv. morsprunorum

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The use of PCR melting profile for typing of Pseudomonas syringae isolates from stone fruit trees

2009

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“…Syringomycin, syringotoxin, and syringostatin are produced by strains of P. syringae pv. syringae (3,10,21,41). These molecules are lipodepsipeptides that are toxic to a wide range of organisms, including plants; they mainly differ in the amino acids found in the peptide parts of the molecules (11).…”

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Biological and Molecular Detection of Toxic Lipodepsipeptide-Producing Pseudomonas syringae Strains and PCR Identification in Plants

Bultreys

Gheysen

1999

Appl Environ Microbiol

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Toxin-based identification procedures are useful for differentiating Pseudomonas syringae pathovars. A biological test on peptone-glucose-NaCl agar in which the yeastRhodotorula pilimanae was used proved to be more reliable for detecting lipodepsipeptide-producing strains of P. syringae than the more usual test on potato dextrose agar in which Geotrichum candidum is used. A PCR test performed with primers designed to amplify a 1,040-bp fragment in the coding sequence of the syrD gene, which was assumed to be involved in syringomycin and syringopeptin secretion, efficiently detected the gene in pathovars that produce the lipodepsipeptides. Comparable results were obtained in both tests performed with strains of the syringomycin-producing organisms P. syringae pv. syringae,P. syringae pv. atrofaciens, and P. syringaepv. aptata, but the PCR test failed with a syringotoxin-producingPseudomonas fuscovaginae strain. The specificity of the test was verified by obtaining negative PCR test results for related pathovars or species that do not produce the toxic lipodepsipeptides.P. syringae pv. syringae was detected repeatedly in liquid medium inoculated with diseased vegetative tissue and assayed by the PCR test. Our procedure was also adapted to detect P. syringae pv. morsprunorum with a cfl gene-based PCR test.

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“…Recently, the covalent structure of this bacterial metabolite, including the chirality of amino acid residues (Ballio et al, 1994a), and some of its biological activities (Di Giorgio et al, 1997) have been reported. Pseudomycin A, as well as its congeners Pseudomycin B, Pseudomycin C and Pseudomycin C′, belongs to the group of pseudomonads lipodepsinonapeptides which includes Syringomycins (Segre et al, 1989;Fukuchi et al, 1990a), Syringotoxins (Ballio et al, 1990;Fukuchi et al, 1990b) and Syringostatins (Isogai et al, 1990). At variance with the latter metabolites, the pseudomycins contain an aspartate residue and a lysine residue in the peptide moiety, features which might influence their conformation and biological properties.…”

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Solution conformation of the Pseudomonas syringae MSU 16H phytotoxic lipodepsipeptide Pseudomycin A determined by computer simulations using distance geometry and molecular dynamics from NMR data

Coiro

Segre

Nola

et al. 1998

European Journal of Biochemistry

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Pseudomycin A is a cyclic lipodepsinonapeptide phytotoxin produced by a strain of the plant pathogenic bacterium Pseudomonas syringae. Like other members of this family of bacterial metabolites, it is characterised by a fatty acylated cyclic peptide with mixed chirality and lactonic closure. Several biological activities of Pseudomycin A are lower than those found for some of its congeners, a difference which might depend on the diverse number and distribution of charged residues in the peptide moiety. Hence, it was of interest to investigate its conformation in solution. After the complete interpretation of the two-dimensional NMR spectra, NOE data were obtained and the structure was determined by computer simulations, applying distance geometry and molecular dynamics procedures. The conformation of the large ring of Pseudomycin A in solution includes three rigid structural regions interrupted by three short flexible regions that act as hinges. The overall three-dimensional structure of the cyclic moiety is similar to that of previously studied bioactive lipodepsinonapeptides produced by other pseudomonads.Keywords : lipodepsinonapeptide ; molecular dynamics; NMR; Pseudomonas syringae; Pseudomycin A; solution structure. Pseudomycin A is the major component of a family of antimycotic lipodepsipeptides isolated from cultures of Pseudomonas syringae MSU 16H (Harrison et al., 1991), a bacterium proposed for the biocontrol of Ophiostoma (Ceratocystis) ulmi, the causal agent of the highly destructive Dutch elm disease (Lam et al., 1987). Recently, the covalent structure of this bacterial metabolite, including the chirality of amino acid residues (Ballio et al., 1994a), and some of its biological activities (Di Giorgio et al., 1997) have been reported. Pseudomycin A, as well as its congeners Pseudomycin B, Pseudomycin C and Pseudomycin C′, belongs to the group of pseudomonads lipodepsinonapeptides which includes Syringomycins (Segre et al., 1989;Fukuchi et al., 1990a), Syringotoxins (Ballio et al., 1990;Fukuchi et al., 1990b) and Syringostatins (Isogai et al., 1990). At variance with the latter metabolites, the pseudomycins contain an aspartate residue and a lysine residue in the peptide moiety, features which might influence their conformation and biological properties. A comparison between the activities of Pseudomycin A and SyrinCorrespondence to V. M. Coiro, Dipartimento di Chimica, Università di Roma 'La Sapienza', p.le Aldo Moro 5, I-00185 Rome, Italy Fax: ϩ39 6 490324. E-mail: coiro@monet.chem.uniroma1.it Abbreviations. A 2 bu, 2,4-diaminobutyric acid; Asp(OH), 3-hydroxyaspartic acid; 2D, two-dimensional; DG, distance geometry; allo-Thr, allo-threonine; Dhb, (Z)-2,3-dehydro-2-aminobutanoic acid; NOE, nuclear Overhauser effect; MD, molecular dynamics ; Thr(Cl), 4-chlorothreonine; TPPI, time proportional phase increment; SA, simulated annealing ; WLIP, white line inducing principle. gomycin E, the prototype of pseudomonad lipodepsinonapeptides, in a number of in vivo and in vitro biological tests has shown that, ...

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Structure of syringotoxin B, a phytotoxin produced by citrus isolates of Pseudomonas syringae pv. syringae.

Cited by 19 publications

References 1 publication

The use of PCR melting profile for typing of Pseudomonas syringae isolates from stone fruit trees

The use of PCR melting profile for typing of Pseudomonas syringae isolates from stone fruit trees

Biological and Molecular Detection of Toxic Lipodepsipeptide-Producing Pseudomonas syringae Strains and PCR Identification in Plants

Solution conformation of the Pseudomonas syringae MSU 16H phytotoxic lipodepsipeptide Pseudomycin A determined by computer simulations using distance geometry and molecular dynamics from NMR data

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