title: Antifungal cyclic lipopeptides from Bacillus amyloliquefaciens strain BO5A.
abstract: A bioassay-guided fractionation of Bacillus amyloliquefaciens strain BO5A afforded the isolation of two new cyclic lipopeptides (1 and 2) as the major lipid constituents (>60%) of the CHCl3-MeOH (2:1) extract. The chemical structures of the isolated metabolites were elucidated by spectroscopic methods, including 1D and 2D NMR spectroscopy, mass spectrometry (MS), secondary ion mass spectrometry (MS1, MS2), and chemical degradation. The compounds are members of the surfactins family and are based on a heptapeptide chain composed by Glu-Val-Leu-Val-Asp-Leu-Leu. Its N-terminal end is N-acylated by an (R)-3-hydroxy fatty acid with linear alkyl chains of 16:0 and 15:0 (1 and 2, respectively). The 3-hydroxyl group closes a 25-membered lactone ring with the carboxylic group of the C-terminal amino acid. The isolated compounds were tested for their inhibitory activity against the four pathogenic fungi Fusarium oxysporum, Aspergillus niger, Botrytis cinerea, and Penicillium italicum and the biocontrol fungus Trichoderma harzianum. Compound 2 displayed activity against all tested pathogens.
authors.affiliation: Dipartimento di Agraria, Università di Napoli Federico II , Via Università 100, 80055 Portici (NA), Italy.
authors.forename: Adriana
authors.initials: A
authors.lastname: Romano
authors.forename: Domenico
authors.initials: D
authors.lastname: Vitullo
authors.forename: Mauro
authors.initials: M
authors.lastname: Senatore
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Lima
authors.forename: Virginia
authors.initials: V
authors.lastname: Lanzotti
mesh_terms: D000595:Amino Acid Sequence; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001234:Aspergillus niger / Q000187:drug effects; D001407:Bacillus / Q000737:chemistry*; D020171:Botrytis / Q000187:drug effects; D005670:Fusarium / Q000187:drug effects; D055666:Lipopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000187:drug effects; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014242:Trichoderma / Q000187:drug effects
chemical_list: D000935:Antifungal Agents; D055666:Lipopeptides; D010456:Peptides, Cyclic