X-ray crystalographic data, absolute configuration, and anticholinesterase effect of dihydromyricitrin 3-O-rhamnoside

  • Sci Rep. 2022 Nov 1;12(1):18351. doi: 10.1038/s41598-022-23240-7.
Mahmoud Fahmi Elsebai  1 ,  Hazem A Ghabbour  2 ,  Ramin Ekhteiari Salmas  3 ,  Ilkay Erdogan Orhan  4 ,  Fatma Sezer Senol Deniz  4
Affiliations
  • 1. Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt. [email protected].
  • 2. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt.
  • 3. Department of Chemistry, Britannia House, King's College London, London, UK.
  • 4. Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, 06330, Ankara, Türkiye.
PMID: 36319690 DOI: 10.1038/s41598-022-23240-7
Abstract

Based on our continuous effort to investigate chemistry and biology of the plant secondary metabolites, we were able to isolate a glycosidal flavonoid 1 from the Wild Egyptian Artichoke. The activity of dihydromyricetin 3-O-rhamnoside (sin. dihydromyricitrin, ampelopsin 3-O-rhamnoside) (1) against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE); its absolute configuration using X-ray crystallography were determined for the first time. Inhibitory activity of 1 against AChE and BChE Enzymes were determined using a slightly modified version of Ellman's method. Compound 1 was revealed to have a potent inhibition against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50 values of 0.070 ± 0.008 and 0.071 ± 0.004 mM, respectively, where IC50 values of the reference drug (galanthamine) were 0.023 ± 0.15 and 0.047 ± 0.91 mM. Compound 1 could be a promising molecule against Alzheimer's disease.

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