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Bioactive and structural metabolites of pseudomonas and burkholderia species causal agents of cultivated mushrooms diseases.

Andolfi A, Cimmino A, Cantore PL, Iacobellis NS, Evidente A - Perspect Medicin Chem (2008)

Bottom Line: In particular, their antimicrobial activity and the alteration of biological and model membranes (red blood cell and liposomes) was established.In the case of tolaasin I interaction with membranes was also related to the tridimensional structure in solution as determined by NMR combined with molecular dynamic calculation techniques.The isolation and structure determination of bioactive metabolites produced by B. gladioli pv. agaricicola are still in progress but preliminary results indicate their peptide nature.

View Article: PubMed Central - PubMed

Affiliation: Dipartimento di Scienze del Suolo, della Pianta, dell'Ambiente e delle Produzioni Animali, Università di Napoli Federico II, Via Università 100, 80055 Portici, Italy.

ABSTRACT
Pseudomonas tolaasii, P. reactans and Burkholderia gladioli pv. agaricicola, are responsible of diseases on some species of cultivated mushrooms. The main bioactive metabolites produced by both Pseudomonas strains are the lipodepsipeptides (LDPs) tolaasin I and II and the so called White Line Inducing Principle (WLIP), respectively, LDPs which have been extensively studied for their role in the disease process and for their biological properties. In particular, their antimicrobial activity and the alteration of biological and model membranes (red blood cell and liposomes) was established. In the case of tolaasin I interaction with membranes was also related to the tridimensional structure in solution as determined by NMR combined with molecular dynamic calculation techniques. Recently, five news minor tolaasins, tolaasins A-E, were isolated from the culture filtrates of P. tolaasii and their chemical structure was determined by extensive use of NMR and MS spectroscopy. Furthermore, their antimicrobial activity was evaluated on target micro-organisms (fungi-including the cultivated mushrooms Agaricus bisporus, Lentinus edodes, and Pleurotus spp.-chromista, yeast and bacteria). The Gram positive bacteria resulted the most sensible and a significant structure-activity relationships was apparent. The isolation and structure determination of bioactive metabolites produced by B. gladioli pv. agaricicola are still in progress but preliminary results indicate their peptide nature. Furthermore, the exopolysaccharide (EPS) from the culture filtrates of B. gladioli pv. agaricicola, as well as the O-chain and lipid A, from the lipopolysaccharide (LPS) of the three bacteria, were isolated and the structures determined.

No MeSH data available.


Related in: MedlinePlus

Relevant HMBC correlation of the anomeric region of the O-chain from Pseudomonas tolaasii.
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f18-pmc-2008-081: Relevant HMBC correlation of the anomeric region of the O-chain from Pseudomonas tolaasii.

Mentions: A gHSQC spectrum registered without decoupling allowed the measurement of the 1JC,H anomeric coupling, thus demonstrating that spin system A and A’ have α-configuration whereas the spin system B and B’ have β-configuration. Residue A had typical proton and carbon signals of a uronic acid substituted at C-4 whereas residue A’ had proton and carbon resonances of a 4-substituted 3-O-acetyl uronic acid. The value of the coupling constants and the 13C chemical shifts were distinctive of a gulo-configurated hexopyranose (De Castro et al. 2003). The other spin systems (B and B’), showing the same resonances and both characterised by the anomeric signals, were identified 3-substituted β-QuipNAc. The acetyl substitution at C-2 of all residues and at C-3 of residue A’ was proven by a HMBC spectrum. The sequence of the monosaccharides in the repeating unit was inferred using interresidual NOE data measured by 2D-NOESY and long range scalar connectivities measured by HMBC spectrum (Fig. 18).


Bioactive and structural metabolites of pseudomonas and burkholderia species causal agents of cultivated mushrooms diseases.

Andolfi A, Cimmino A, Cantore PL, Iacobellis NS, Evidente A - Perspect Medicin Chem (2008)

Relevant HMBC correlation of the anomeric region of the O-chain from Pseudomonas tolaasii.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2746572&req=5

f18-pmc-2008-081: Relevant HMBC correlation of the anomeric region of the O-chain from Pseudomonas tolaasii.
Mentions: A gHSQC spectrum registered without decoupling allowed the measurement of the 1JC,H anomeric coupling, thus demonstrating that spin system A and A’ have α-configuration whereas the spin system B and B’ have β-configuration. Residue A had typical proton and carbon signals of a uronic acid substituted at C-4 whereas residue A’ had proton and carbon resonances of a 4-substituted 3-O-acetyl uronic acid. The value of the coupling constants and the 13C chemical shifts were distinctive of a gulo-configurated hexopyranose (De Castro et al. 2003). The other spin systems (B and B’), showing the same resonances and both characterised by the anomeric signals, were identified 3-substituted β-QuipNAc. The acetyl substitution at C-2 of all residues and at C-3 of residue A’ was proven by a HMBC spectrum. The sequence of the monosaccharides in the repeating unit was inferred using interresidual NOE data measured by 2D-NOESY and long range scalar connectivities measured by HMBC spectrum (Fig. 18).

Bottom Line: In particular, their antimicrobial activity and the alteration of biological and model membranes (red blood cell and liposomes) was established.In the case of tolaasin I interaction with membranes was also related to the tridimensional structure in solution as determined by NMR combined with molecular dynamic calculation techniques.The isolation and structure determination of bioactive metabolites produced by B. gladioli pv. agaricicola are still in progress but preliminary results indicate their peptide nature.

View Article: PubMed Central - PubMed

Affiliation: Dipartimento di Scienze del Suolo, della Pianta, dell'Ambiente e delle Produzioni Animali, Università di Napoli Federico II, Via Università 100, 80055 Portici, Italy.

ABSTRACT
Pseudomonas tolaasii, P. reactans and Burkholderia gladioli pv. agaricicola, are responsible of diseases on some species of cultivated mushrooms. The main bioactive metabolites produced by both Pseudomonas strains are the lipodepsipeptides (LDPs) tolaasin I and II and the so called White Line Inducing Principle (WLIP), respectively, LDPs which have been extensively studied for their role in the disease process and for their biological properties. In particular, their antimicrobial activity and the alteration of biological and model membranes (red blood cell and liposomes) was established. In the case of tolaasin I interaction with membranes was also related to the tridimensional structure in solution as determined by NMR combined with molecular dynamic calculation techniques. Recently, five news minor tolaasins, tolaasins A-E, were isolated from the culture filtrates of P. tolaasii and their chemical structure was determined by extensive use of NMR and MS spectroscopy. Furthermore, their antimicrobial activity was evaluated on target micro-organisms (fungi-including the cultivated mushrooms Agaricus bisporus, Lentinus edodes, and Pleurotus spp.-chromista, yeast and bacteria). The Gram positive bacteria resulted the most sensible and a significant structure-activity relationships was apparent. The isolation and structure determination of bioactive metabolites produced by B. gladioli pv. agaricicola are still in progress but preliminary results indicate their peptide nature. Furthermore, the exopolysaccharide (EPS) from the culture filtrates of B. gladioli pv. agaricicola, as well as the O-chain and lipid A, from the lipopolysaccharide (LPS) of the three bacteria, were isolated and the structures determined.

No MeSH data available.


Related in: MedlinePlus