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.

Preview	Text marinedrugs-10-02912.pdf - Published Version Available under License Creative Commons Attribution. Download (895kB) | Preview
Preview	Text marinedrugs-10-00234-s001.pdf - Supplemental Material Available under License Creative Commons Attribution. Download (445kB) | Preview

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.

Actions (login required)

View Item