Phenolic Derivatives with Anti-Acetylcholinesterase Inhibitory Activities from Galeola nudifolia in Vietnam

Kiep Minh Do, Yu Nakashima, Takeshi Kodama, Yuan E. Lee, Hien Minh Nguyen, Naotaka Ikumi, Hiroyuki Morita*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A new phenolic derivative, galeomalate A (1), together with five known structurally related compounds (2-6), was isolated from the ethyl acetate extract of Galeola nudifolia collected in Vietnam. The structures were elucidated by various spectroscopic methods, including 1D and 2D NMR, HR-ESI-TOF-MS, and CD data, and chemical conversion of the sugar moiety. All isolated compounds possessed acetylcholinesterase (AChE) inhibitory activities in a dose-dependent manner. Among them, compounds 2 and 3 exhibited the first and second highest inhibitory activity on AChE with IC50 values of 122.13 and 125.49 μM, respectively. Compounds 1 and 4–6 inhibited the AChE activity by mixed modes of action comprising competitive and non-competitive modes, whereas 2 and 3 exerted their inhibitory activities in a competitive manner. Molecular docking analyses suggested that the phenyl-β-D-glucopyranoside unit of 2 and 3 bound to the active site of AChE for the competitive inhibitory activities, while the mixed inhibitory activity of 4 was due to the two binding patterns in the active-site and the active-site entrance of AChE. Furthermore, the docking studies indicated that 1, 5, and 6 would inhibit AChE in a mixed inhibitory manner by adopting three distinct binding patterns of the additional phenyl-β-D-glucopyranoside unit at the active-site entrance.

Original languageEnglish
Article numbere202301482
JournalChemistry and Biodiversity
Volume20
Issue number12
DOIs
StatePublished - 2023/12

Keywords

  • Galeola nudifolia
  • Galeomalate A
  • Orchidaceae
  • acetylcholinesterase inhibitory activity
  • molecular docking

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • General Chemistry
  • Molecular Medicine
  • Molecular Biology

Fingerprint

Dive into the research topics of 'Phenolic Derivatives with Anti-Acetylcholinesterase Inhibitory Activities from Galeola nudifolia in Vietnam'. Together they form a unique fingerprint.

Cite this