Psychrophilin A and cycloaspeptide D, novel cyclic peptides from the psychrotolerant fungus Penicillium ribeum

Two fungal metabolites, psychrophilin A (1) and cycloaspeptide D (2), together with the known cycloaspeptide A (3) were isolated from the psychrotolerant fungus Penicillium ribeum. using high-speed countercurrent chromatography (HSCCC) and preparative HPLC. The structures were determined from 1D and 2D NMR techniques, HREIMS, tandem mass spectrometry (ESMS/MS), and X-ray crystallography. The amino acid residues of psychrophilin A (1) and cycloaspeptide D (2) were all found to possess the L configuration by Marfey's method. Psychrophilin A (1) is the first natural cyclic peptide containing a nitro group instead of an amino group.