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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.


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HPLC profile of crude tolaasins preparation.
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f4-pmc-2008-081: HPLC profile of crude tolaasins preparation.

Mentions: Tolaasin I is considered the main virulence factor of P. tolaasii and responsible for the symptoms development on the mushrooms (Rainey et al. 1991; 1992; Soler-Rivas et al. 1999a) and this is apparently due to the ability of this molecule to disrupt cell membrane function by the transmembrane pore formation (Brodey et al. 1991; Rainey et al. 1991; Hutchinson and Johnstone, 1993). Tolaasin I was isolated from the cell-free bacterial culture filtrate of the type strain NCPPB2192 of P. tolaasii following a modification of the method described by Peng (1996). The further purification of the tolaasin I preparation by HPLC showed that P. tolaasii, besides the already known tolaasin I and II, which differ for the presence of Hse and Gly, respectively, in position 16, (Nutkins et al. 1991), produced in vitro other chemical correlated metabolites confirming previous findings (Shirata et al. 1995). HPLC profile of a crude tolaasin preparation (Fig. 4) carried out on an Analytical Brownlee Aquapore RP-300 (C8) column using water (0.1% TFA, v/v) and CH3CN as solvent system with a flow rates of 1.0 ml/min−1 [a Brown-lee Aquapore RP-300 (C8) column using the same solvent system with flow rate 4.7 ml/min was used for semipreparative purpose] showed the presence of five minor peaks, named tolaasins A, B, C, D, and E (Bassarello et al. 2004).


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)

HPLC profile of crude tolaasins preparation.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f4-pmc-2008-081: HPLC profile of crude tolaasins preparation.
Mentions: Tolaasin I is considered the main virulence factor of P. tolaasii and responsible for the symptoms development on the mushrooms (Rainey et al. 1991; 1992; Soler-Rivas et al. 1999a) and this is apparently due to the ability of this molecule to disrupt cell membrane function by the transmembrane pore formation (Brodey et al. 1991; Rainey et al. 1991; Hutchinson and Johnstone, 1993). Tolaasin I was isolated from the cell-free bacterial culture filtrate of the type strain NCPPB2192 of P. tolaasii following a modification of the method described by Peng (1996). The further purification of the tolaasin I preparation by HPLC showed that P. tolaasii, besides the already known tolaasin I and II, which differ for the presence of Hse and Gly, respectively, in position 16, (Nutkins et al. 1991), produced in vitro other chemical correlated metabolites confirming previous findings (Shirata et al. 1995). HPLC profile of a crude tolaasin preparation (Fig. 4) carried out on an Analytical Brownlee Aquapore RP-300 (C8) column using water (0.1% TFA, v/v) and CH3CN as solvent system with a flow rates of 1.0 ml/min−1 [a Brown-lee Aquapore RP-300 (C8) column using the same solvent system with flow rate 4.7 ml/min was used for semipreparative purpose] showed the presence of five minor peaks, named tolaasins A, B, C, D, and E (Bassarello et al. 2004).

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