Journal Article

FZJ-2018-07358

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Substituted l -tryptophan- l -phenyllactic acid conjugates produced by an endophytic fungus Aspergillus aculeatus using an OSMAC approach

Wang, H. ; Eze, P. M. ; Höfert, S.-P. ; Janiak, C. ; Hartmann, R.FZJ* ; Okoye, F. B. C. ; Esimone, C. O. ; Orfali, R. S. ; Dai, H. ; Liu, Z. ; Proksch, P. (Corresponding author)

2018
RSC Publishing London

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Please use a persistent id in citations: http://hdl.handle.net/2128/20792  doi:10.1039/C8RA00200B

Abstract: The endophytic fungus Aspergillus aculeatus isolated from leaves of the papaya plant Carica papaya was fermented on solid rice medium, yielding a new L-tryptophan-L-phenyllactic acid conjugate (1) and thirteen known compounds (11, 14–25). In addition, an OSMAC approach was employed by adding eight different sodium or ammonium salts to the rice medium. Addition of 3.5% NaNO3 caused a significant change of the metabolite pattern of the fungus as indicated by HPLC analysis. Subsequent isolation yielded several new substituted L-tryptophan-L-phenyllactic acid conjugates (1–10) in addition to three known compounds (11–13), among which compounds 2–10, 12–13 were not detected in the rice control culture. All structures were unambiguously elucidated by one and two dimensional NMR spectroscopy and by mass spectrometry. The absolute configuration of the new compounds was determined by Marfey's reaction and X-ray single crystal diffraction. Compounds 19–22 showed cytotoxicity against the L5178Y mouse lymphoma cell line with IC50 values of 3.4, 1.4, 7.3 and 23.7 μM, respectively.

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Contributing Institute(s):

1. Strukturbiochemie (ICS-6)

Research Program(s):

1. 551 - Functional Macromolecules and Complexes (POF3-551) (POF3-551)

Appears in the scientific report 2018

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Database coverage:
; ; ; ; Clarivate Analytics Master Journal List ; Current Contents - Physical, Chemical and Earth Sciences ; DOAJ Seal ; IF < 5 ; JCR ; NCBI Molecular Biology Database ; National-Konsortium ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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