Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus

Gulder, Tobias A. M., Hong, Hanna, Correa, Jhonny, Eguereva, Ekaterina, Wiese, Jutta, Imhoff, Johannes F. and Gross, Harald (2012) Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus Marine Drugs, 10 (12). pp. 2912-2935. DOI 10.3390/md10122912.

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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.

Document Type: Article
Additional Information: WOS:000312607700020
Keywords: fungus; Asteromyces cruciatus; cyclic peptides; OSMAC; total synthesis; NATURAL-PRODUCTS; SECONDARY METABOLITES; SUBINHIBITORY CONCENTRATIONS; STREPTOMYCES SP; DIVERSITY; ANTIBIOTICS; GLIOVICTIN; INHIBITOR; DISCOVERY; INDUCE
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MI Marine Microbiology
OceanRep > GEOMAR > Applied R&D > Centre for Marine Substances (KiWiZ)
Refereed: Yes
DOI etc.: 10.3390/md10122912
ISSN: 1660-3397
Projects: KIWIZ, Future Ocean
Date Deposited: 19 Dec 2012 13:08
Last Modified: 02 Mar 2018 12:56
URI: http://eprints.uni-kiel.de/id/eprint/19891

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