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Four new lipid siderophores bearing both L- threo - and L- erythro -β-hydroxyaspartic acids, potashchelins A-D ( 1 - 4 ), were isolated from the potash-salt-ore-derived extremophile  Halomonas  sp. MG34. The planar structures of  1 - 4  were elucidated on the basis of extensive 1D and 2D NMR studies and MS/MS data. Potashchelins  1 - 4  contain a hydrophilic nonapeptide headgroup sequentially consisting of β-hydroxyaspartic acid, serine, glycine, serine, serine, β-hydroxyaspartic acid, threonine, serine, and cyclic N(δ)-hydroxy-ornithine, which is appended by one of a series of fatty acids ranging from dodecanoic acid to tetradecanoic acid. The absolute configurations of the amino acids of potashchelins  1 - 4  were determined by C 3  and advanced Marfey's reaction, partial hydrolysis, and bioinformatics analysis, which revealed that potashchelins  1 - 4  bear both L- threo - and L- erythro -β-hydroxyaspartic acid. Phylogenetic analysis showed that the stand-alone β-hydroxylase, PtcA, and the fused domain with β-hydroxylase activity in PtcB are expected to be responsible for the formation of L- erythro  and L- threo  diastereomers, respectively. Additionally, utilizing a comparative genomics approach, we revealed an evolutionary mechanism for lipid siderophores in  Halomonas  involving horizontal transfer. Bioassays showed that potashchelin A and D had weak antibacterial activity against  B. subtilis  CPCC 100029 with an MIC value of 64 μg/mL.

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Potashchelins, a Suite of Lipid Siderophores Bearing Both L-threo and L-erythro Beta-Hydroxyaspartic Acids, Acquired From the Potash-Salt-Ore-Derived Extremophile Halomonas sp. MG34