Journal
MARINE DRUGS
Volume 10, Issue 12, Pages 2912-2935Publisher
MDPI
DOI: 10.3390/md10122912
Keywords
fungus; Asteromyces cruciatus; cyclic peptides; OSMAC; total synthesis
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Funding
- Evonik Foundation
- North Rhine-Westphalian Academy of Sciences, Humanities and the Arts (Junges Kolleg)
- Fonds of the Chemical Industry
- Emmy Noether Program of the DFG [GU 1233/1-1]
- Deutsche Forschungsgemeinschaft (DFG) within the Research Unit FOR854 [GR 2673/2-1]
- Panamanian government
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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), N-1-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.
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