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Orfamide-type cyclic lipopeptides (CLPs) are biosurfactants produced by  Pseudomonas  and involved in lysis of oomycete zoospores, biocontrol of  Rhizoctonia  and insecticidal activity against aphids. In this study, we compared the biosynthesis, structural diversity,  in vitro  and  in planta  activities of orfamides produced by rhizosphere-derived  Pseudomonas protegens  and related  Pseudomonas  species. Genetic characterization together with chemical identification revealed that the main orfamide compound produced by the  P .  protegens  group is orfamide A, while the related strains  Pseudomonas  sp. CMR5c and CMR12a produce orfamide B. Comparison of orfamide fingerprints led to the discovery of two new orfamide homologs (orfamide F and orfamide G) in  Pseudomonas  sp. CMR5c. The structures of these two CLPs were determined by nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. Mutagenesis and complementation showed that orfamides determine the swarming motility of parental  Pseudomonas  sp. strain CMR5c and their production was regulated by  luxR  type regulators. Orfamide A and orfamide B differ only in the identity of a single amino acid, while orfamide B and orfamide G share the same amino acid sequence but differ in length of the fatty acid part. The biological activities of orfamide A, orfamide B, and orfamide G were compared in further bioassays. The three compounds were equally active against  Magnaporthe oryzae  on rice, against  Rhizoctonia solani  AG 4-HGI in  in vitro  assays, and caused zoospore lysis of  Phytophthora  and  Pythium . Furthermore, we could show that orfamides decrease blast severity in rice plants by blocking appressorium formation in  M. oryzae . Taken all together, our study shows that orfamides produced by  P. protegens  and related species have potential in biological control of a broad spectrum of fungal plant pathogens.

Biosynthesis, Chemical Structure, and Structure-Activity Relationship of Orfamide Lipopeptides Produced by Pseudomonas protegens and Related Species