Isolation and characterization of three pairs of indolediketopiperazine enantiomers containing infrequent N-methoxy substitution from the marine algal-derived endophytic fungus Acrostalagmus luteoalbus TK-43

Cao J., Li X., Meng L., KONUKLUGİL B., Li X., Li H., ...More

Bioorganic Chemistry, vol.90, 2019 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 90
  • Publication Date: 2019
  • Doi Number: 10.1016/j.bioorg.2019.103030
  • Journal Name: Bioorganic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Keywords: Acrostalagmus luteoalbus, N-methoxy, Indolediketopiperazine enantiomers, Anti-acetylcholinesterase activity, Anti-microbial activity
  • Lokman Hekim University Affiliated: No


© 2019 Elsevier Inc.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.