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Isolation, structure elucidation and total synthesis of lajollamide A from the marine fungus Asteromyces cruciatus.

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.

SUBMITTER: Gulder TA 

PROVIDER: S-EPMC3528133 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Isolation, structure elucidation and total synthesis of lajollamide A from the marine fungus Asteromyces cruciatus.

Gulder Tobias A M TA   Hong Hanna H   Correa Jhonny J   Egereva Ekaterina E   Wiese Jutta J   Imhoff Johannes F JF   Gross Harald H  

Marine drugs 20121201 12

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 unambi  ...[more]

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