Alkaloids with cholinesterase inhibitory activities from the bulbs of Crinum × amabile Donn ex Ker Gawl

Waraluck Chaichompoo; Pornchai Rojsitthisak; Wachirachai Pabuprapap; Yuttana Siriwattanasathien; Pathumwadee Yotmanee; Apichart Suksamrarn

doi:10.1016/j.phytochem.2022.113473

Alkaloids with cholinesterase inhibitory activities from the bulbs of Crinum × amabile Donn ex Ker Gawl

Phytochemistry. 2023 Jan:205:113473. doi: 10.1016/j.phytochem.2022.113473. Epub 2022 Oct 14.

Authors

Waraluck Chaichompoo¹, Pornchai Rojsitthisak², Wachirachai Pabuprapap³, Yuttana Siriwattanasathien³, Pathumwadee Yotmanee³, Apichart Suksamrarn³

Affiliations

¹ Department of Food and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, 10330, Thailand; Center of Excellence in Natural Products for Aging and Chronic Diseases, Chulalongkorn University, Bangkok, 10330, Thailand.
² Department of Food and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, 10330, Thailand; Center of Excellence in Natural Products for Aging and Chronic Diseases, Chulalongkorn University, Bangkok, 10330, Thailand. Electronic address: pornchai.r@chula.ac.th.
³ Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, 10240, Thailand.

PMID: 36244402
DOI: 10.1016/j.phytochem.2022.113473

Abstract

Seven previously undescribed alkaloids, crinamabilines A-G, two non-alkaloidal compounds, crinamabidiene and 6-phenylpiperonyl alcohol, two first naturally occurring alkaloids, 3-epibuphanisine and (+)-1β,2β-epoxy-epicrinine, together with nineteen known alkaloids, were isolated from the bulbs of Crinum × amabile Donn ex Ker Gawl. Their structures and absolute configurations were elucidated by NMR, MS and ECD spectroscopic techniques. Ungeremine displayed the most potent inhibitory activity against acetylcholinesterase (IC₅₀ 0.21 μM), which was about 6-fold more active than the reference drug, galanthamine (IC₅₀ 1.23 μM). Ungeremine also exhibited the strongest inhibitory activity against butyrylcholinesterase (IC₅₀ 3.57 μM), which was comparable to galanthamine (IC₅₀ 3.11 μM). The molecular docking studies were performed and were well in agreement with the experimental results.

Keywords: Acetylcholinesterase; Alkaloids; Amaryllidaceae; Butyrylcholinesterase; Crinum × amabile Donn ex Ker Gawl.; Molecular docking.

MeSH terms

Acetylcholinesterase
Butyrylcholinesterase
Crinum*
Molecular Docking Simulation

Substances

Butyrylcholinesterase
Acetylcholinesterase