title: Novel cyclic peptide, epichlicin, from the endophytic fungus, Epichloe typhina.
abstract: The novel cyclic peptide, epichlicin, was isolated from Epichloe typhina, an endophytic fungus of the timothy plant (Phleum pretense L.). Its structure was determined by NMR studies and by mass spectrometry. Enantiomers of 3-amino tetradecanoic acid, a constituent amino acid of epichlicin, were synthesized as authentic standards. The stereochemistry of each amino acid was elucidated through a combination of the advanced Marfey method and chemical manipulation. Epichlicin showed inhibitory activity toward the spore germination of Cladosporium phlei, a pathogenic fungus of the timothy plant at an IC50 value of 22 nM.
authors.affiliation: Laboratory of Bioorganic Chemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Japan.
authors.forename: Yoshiya
authors.initials: Y
authors.lastname: Seto
authors.forename: Kosaku
authors.initials: K
authors.lastname: Takahashi
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Matsuura
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Kogami
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Yada
authors.forename: Teruhiko
authors.initials: T
authors.lastname: Yoshihara
authors.forename: Kensuke
authors.initials: K
authors.lastname: Nabeta
mesh_terms: D000935:Antifungal Agents / Q000494:pharmacology*; D002963:Cladosporium / Q000187:drug effects; D005658:Fungi / Q000737:chemistry*; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D031784:Phleum / Q000382:microbiology; D010935:Plant Diseases / Q000382:microbiology; D013170:Spores / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D010456:Peptides, Cyclic; C522931:epichlicin