%0 Journal Article
%T Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus
%A Tobias A. M. Gulder
%A Hanna Hong
%A Jhonny Correa
%A Ekaterina Egereva
%A Jutta Wiese
%A Johannes F. Imhoff
%A Harald Gross
%J Marine Drugs
%D 2012
%I MDPI AG
%R 10.3390/md10122912
%X 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), 1 N-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.
%K fungus
%K Asteromyces cruciatus
%K cyclic peptides
%K OSMAC
%K total synthesis
%U http://www.mdpi.com/1660-3397/10/12/2912