New biphenanthrenes with butyrylcholinesterase inhibitory activitiy from Cremastra appendiculata

Encouraged by the in vitro potent inhibitory activity on butyrylcholinesterase (BChE) of 95% ethanol extract of Cremastra appendiculata (D. Don) Makino tubers, a further phytochemical investigation on C. appendiculata tubers was conducted, which led to the isolation of a pair of new biphenanthrene a...

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Bibliographic Details
Published in:Natural product research 2021-03, Vol.35 (5), p.750-756
Main Authors: Liu, Liang, Yin, Qi-Meng, Gao, Qian, Li, Jun, Jiang, Yong, Tu, Peng-Fei
Format: Article
Language:English
Subjects:
Acetylcholinesterase
Acetylcholinesterase - metabolism
BChE inhibitory effect
biphenanthrene atropisomer
Butyrylcholinesterase - chemistry
Butyrylcholinesterase - metabolism
Carbon-13 Magnetic Resonance Spectroscopy
Cholinesterase Inhibitors - chemistry
Cholinesterase Inhibitors - pharmacology
Cremastra appendiculata
Ethanol
Inhibitory Concentration 50
Orchidaceae - chemistry
Phenanthrenes - pharmacology
Phytochemicals - analysis
Plant Tubers - chemistry
Proton Magnetic Resonance Spectroscopy
Tubers
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Summary:Encouraged by the in vitro potent inhibitory activity on butyrylcholinesterase (BChE) of 95% ethanol extract of Cremastra appendiculata (D. Don) Makino tubers, a further phytochemical investigation on C. appendiculata tubers was conducted, which led to the isolation of a pair of new biphenanthrene atropisomers, namely cremaphenanthrene F-G (1-2). Their structures were elucidated on the basis of extensive spectroscopic analyses and chemical method. It is the first time that biphenanthrene atropisomers have been isolated from the plant kingdom. Compound 1 showed potent BChE inhibitory effect with IC 50 value of 14.62 ± 2.15 μM. Compound 2 exhibited weak BChE inhibitory effect with IC 50 value of 79.56 ± 0.78 μM. Meanwhile, 1 and 2 were found to be inactive for acetylcholinesterase (AChE) inhibition. These findings suggested that compound 1 was a promising selective BChE inhibitor for AD prevention and treatment.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2019.1601091