Novel cyclic peptide, epichlicin, from the endophytic fungus, Epichloe typhina.
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.
Seto
Yoshiya
Y
Laboratory of Bioorganic Chemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Japan.
Takahashi
Kosaku
K
Matsuura
Hideyuki
H
Kogami
Yasunori
Y
Yada
Hiroshi
H
Yoshihara
Teruhiko
T
Nabeta
Kensuke
K
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
D000935:Antifungal Agents; D010456:Peptides, Cyclic; C522931:epichlicin