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. Open Access 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
Open Access Journal?: 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://oceanrep.geomar.de/id/eprint/19891

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