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Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus
Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk Str. 1, Bonn 53121, Germany
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, Bonn 53115, Germany
Kieler Wirkstoff-Zentrum (KiWiZ) at the Helmholtz-Zentrum für Ozeanforschung GEOMAR, Am Kiel-Kanal 44, Kiel 24106, Germany
Institute for Pharmaceutical Biology, University of Tübingen, Auf der Morgenstelle 8, Tübingen 72076, Germany
These authors contributed equally to this work.
Current address: Institute for Microbiology and Biotechnology, University of Bonn, Meckenheimer Allee 168, Bonn 53115, Germany.
* Authors to whom correspondence should be addressed.
Received: 9 November 2012; in revised form: 29 November 2012 / Accepted: 5 December 2012 / Published: 19 December 2012
Abstract: The marine-derived filamentous fungus Asteromyces cruciatus 763, obtained off the coast of La Jolla, San Diego, USA, yielded the new pentapeptide lajollamide A (1), along with the known compounds regiolone (2), hyalodendrin (3), gliovictin (4), 1N-norgliovicitin (5), and bis-N-norgliovictin (6). The planar structure of lajollamide A (1) was determined by Nuclear Magnetic Resonance (NMR) spectroscopy in combination with mass spectrometry. The absolute configuration of lajollamide A (1) was unambiguously solved by total synthesis which provided three additional diastereomers of 1 and also revealed that an unexpected acid-mediated partial racemization (2:1) of the l-leucine and l-N-Me-leucine residues occurred during the chemical degradation process. The biological activities of the isolated metabolites, in particular their antimicrobial properties, were investigated in a series of assay systems.
Keywords: fungus; Asteromyces cruciatus; cyclic peptides; OSMAC; total synthesis
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Gulder, T.A.M.; Hong, H.; Correa, J.; Egereva, E.; Wiese, J.; Imhoff, J.F.; Gross, H. Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus. Mar. Drugs 2012, 10, 2912-2935.
Gulder TAM, Hong H, Correa J, Egereva E, Wiese J, Imhoff JF, Gross H. Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus. Marine Drugs. 2012; 10(12):2912-2935.
Gulder, Tobias A.M.; Hong, Hanna; Correa, Jhonny; Egereva, Ekaterina; Wiese, Jutta; Imhoff, Johannes F.; Gross, Harald. 2012. "Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus." Mar. Drugs 10, no. 12: 2912-2935.