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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
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Current address: Institute for Microbiology and Biotechnology, University of Bonn, Meckenheimer Allee 168, Bonn 53115, Germany.
Mar. Drugs 2012, 10(12), 2912-2935;
Received: 9 November 2012 / Revised: 29 November 2012 / Accepted: 5 December 2012 / Published: 19 December 2012
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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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. View Full-Text
Keywords: fungus; Asteromyces cruciatus; cyclic peptides; OSMAC; total synthesis 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.

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