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Two new cyclopentapeptides, xylapeptide A ( 1 ) with an uncommon  L -pipecolinic acid moiety, and xylapeptide B ( 2 ) having a common  L -proline residue were identified from an associated fungus  Xylaria  sp. isolated from the Chinese medicinal plant  Sophora tonkinensis . Their planar structures were elucidated by a comprehensive analysis of NMR and MS spectroscopic spectra. The absolute configurations were determined by Marfey’s method and single-crystal X-ray diffraction (Cu K α ) analysis. Xylapeptide A ( 1 ) is the first example of cyclopentapeptide with  L -Pip of terrestrial origin and showed strong antibacterial activity against  Bacillus subtilis  and  B. cereus  with MIC value of 12.5  μ g/mL.

Xylapeptide A, an Antibacterial Cyclopentapeptide with an Uncommon L-Pipecolinic Acid Moiety from the Associated Fungus Xylaria sp. (GDG-102)