Journal
BIOORGANIC CHEMISTRY
Volume 90, Issue -, Pages -Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2019.103030
Keywords
Acrostalagmus luteoalbus; N-methoxy; Indolediketopiperazine enantiomers; Anti-acetylcholinesterase activity; Anti-microbial activity
Funding
- National Natural Science Foundation of China (NSFC) [81673351, 31330009]
- European Commission under the program Marie Curie Actions-International Research Staff Exchange Scheme (IRSES) [PIRSES-GA-2011-295226]
- Taishan Scholar Project from Shandong Province of China
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Three pairs of new N-methoxy-containing indolediketopiperazine enantiomers, acrozines A-C (1-3), were isolated from the culture extract of Acrostalagmus luteoalbus TK-43, an endophytic fungus obtained from the marine green alga Codium fragile. The optical resolution of compounds 1-3 by chiral HPLC successfully afforded individual enantiomers (+)-1/(-)-1, (+)-2/(-)-2, and (+)-3/(-)-3, respectively. The structures of all these compounds were established on the basis of detailed interpretation of their NMR and mass spectroscopic data. X-ray crystallographic analysis confirmed the structures of compounds 1-3, while the absolute configurations were determined by TDDFT-ECD calculations. All these compounds containing a N-methoxy group which is uncommon in indolediketopiperazines. The enantiomers, (+)-2/(-)- 2, showed different antimicrobial activities against several plant-pathogenic fungi, while (+)-1 displayed better inhibitory activity against acetylcholinesterase than that of (-)-1.
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