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

Marine Drugs

Tobias A. M. Gulder¹  Hanna Hong¹  Jhonny Correa²  Ekaterina Egereva²  Jutta Wiese³  Johannes F. Imhoff³ 

[1] Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk Str. 1, Bonn 53121, Germany; E-Mail:;Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, Bonn 53115, Germany; E-Mails:;Kieler Wirkstoff-Zentrum (KiWiZ) at the Helmholtz-Zentrum für Ozeanforschung GEOMAR, Am Kiel-Kanal 44, Kiel 24106, Germany; E-Mails:

关键词: fungus;    Asteromyces cruciatus;    cyclic peptides;    OSMAC;    total synthesis;   

DOI  :  10.3390/md10122912

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.