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...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2004-05, Vol.67 (5), p.878-881
Hauptverfasser: DALSGAARD, Petur Weihe, LARSEN, Thomas Ostenfeld, FRYDENVANG, Karla, CHRISTOPHERSEN, Carsten
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Sprache:eng
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Zusammenfassung: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0303714