Abstract
Two cyclotetrapeptides, henceforth named Provipeptides A (1) and B (2), along with five known diketopiperazines (3–7) were isolated from the liquid culture of marine Streptomyces sp. 161a recovered from a sample of sea grass Bryopsis sp. The structures of cyclotetrapeptides and diketopiperazines (DKPs) were established by 1D and 2D NMR data, MS, and by comparison with literature data. The absolute stereochemistry of compounds cyclo-(l-Pro-l-Leu-d-Pro-l-Phe) 1 and cyclo-(-Pro-Ile-Pro-Phe) 2 was established by the Marfey’s method. Compound 1 showed antibacterial activity against rice phytopathogenic strains Burkholderia glumae (MIC = 1.1 mM) and Burkholderia gladioli (MIC = 0.068 mM), compound 2 was active only against B. glumae (MIC = 1.1 mM), and DKP cyclo-[l-Pro-l-Leu] 5 showed to be active against B. gladioli (MIC = 0.3 mM) and B. glumae (MIC = 2.4 mM). Compounds 1 and 2 showed 65% and 50% inhibition of Colletotrichum gloeosporioides (yam pathogen) conidia germination, respectively at a concentration of 1.1 mM.
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Acknowledgements
This study was conducted with the financial support of COLCIENCIAS (grant Cod. 1101-659-44402 CT.537/14) and International Foundation for Science IFS, Uppsala-Sweden (grant Cod. 5023–2). Universidad Nacional de Colombia DIEB grant 37151. L.A.B thanks the Programa Doctoral Becas Colciencias (567) for the granted scholarship (2012), Universidad de Caldas for the leave of absence for doctoral studies. The ANLA (Agencia Nacional de Licencias Ambientales) and the Ministerio de Ambiente y Desarrollo Sostenible granted permission to collect samples and perform this research (Permission No 4 of 10/02/2010, Anexo 2, Contrato de Acceso a Recurso Genético No 108).
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Betancur, L.A., Forero, A.M., Romero-Otero, A. et al. Cyclic tetrapeptides from the marine strain Streptomyces sp. PNM-161a with activity against rice and yam phytopathogens. J Antibiot 72, 744–751 (2019). https://doi.org/10.1038/s41429-019-0201-0
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DOI: https://doi.org/10.1038/s41429-019-0201-0
