Inhibitory activity of the biocontrol bacterial strain Lysobacter capsici AZ78 is related to the production of cyclo(l-Pro-l-Tyr), a 2,5-diketopiperazine with in vitro and in vivo toxic activity against Phytophthora infestans and Plasmopara viticola. Further investigation of culture filtrate organic extracts showed its ability to produce other 2,5-diketopiperazines. They were isolated and identified by spectroscopic (1H NMR and ESIMS) and physic (specific optical rotation) methods as cyclo(l-Pro-l-Val), cyclo(d-Pro-d-Phe), cyclo(l-Pro-l-Leu), and cyclo(d-Pro-l-Tyr). When tested against the phytopathogenic Gram-positive bacterium Rhodococcus fascians LMG 3605, cyclo(l-Pro-l-Val) showed a toxic activity similar to chloramphenicol at a comparable concentration. Overall, these data suggest that 2,5-diketopiperazines represent a class of metabolites characterizing the metabolome of L. capsici AZ78. Furthermore, the toxic activity showed by cyclo(l-Pro-l-Val) against R. fascians LMG 3605 broaden the spectrum activity of 2,5-diketopiperazines against phytopathogenic microorganisms enforcing their potential development as biopesticides.

Cimmino, A.; Bejarano, A.; Masi, M.; Puopolo, G.; Evidente, A. (2021). Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians. NATURAL PRODUCT RESEARCH, 35 (23): 4969-4977. doi: 10.1080/14786419.2020.1756803 handle: http://hdl.handle.net/10449/68891

Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians

Puopolo, Gerardo;
2021

Abstract

Inhibitory activity of the biocontrol bacterial strain Lysobacter capsici AZ78 is related to the production of cyclo(l-Pro-l-Tyr), a 2,5-diketopiperazine with in vitro and in vivo toxic activity against Phytophthora infestans and Plasmopara viticola. Further investigation of culture filtrate organic extracts showed its ability to produce other 2,5-diketopiperazines. They were isolated and identified by spectroscopic (1H NMR and ESIMS) and physic (specific optical rotation) methods as cyclo(l-Pro-l-Val), cyclo(d-Pro-d-Phe), cyclo(l-Pro-l-Leu), and cyclo(d-Pro-l-Tyr). When tested against the phytopathogenic Gram-positive bacterium Rhodococcus fascians LMG 3605, cyclo(l-Pro-l-Val) showed a toxic activity similar to chloramphenicol at a comparable concentration. Overall, these data suggest that 2,5-diketopiperazines represent a class of metabolites characterizing the metabolome of L. capsici AZ78. Furthermore, the toxic activity showed by cyclo(l-Pro-l-Val) against R. fascians LMG 3605 broaden the spectrum activity of 2,5-diketopiperazines against phytopathogenic microorganisms enforcing their potential development as biopesticides.
Lysobacter capsici
Cyclic dipeptides
25-diketopiperazines
Biopesticides
Rhodococcus fascians
Settore AGR/12 - PATOLOGIA VEGETALE
Cimmino, A.; Bejarano, A.; Masi, M.; Puopolo, G.; Evidente, A. (2021). Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians. NATURAL PRODUCT RESEARCH, 35 (23): 4969-4977. doi: 10.1080/14786419.2020.1756803 handle: http://hdl.handle.net/10449/68891
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