Coumarins from Sarcandra glabra (Thunb.) Nakai and Acetylcholinesterase Inhibiting Activity

Abstract

Nine coumarins including a pair of new enantiomers (1a/1b) and seven known compounds (2 -8) were isolated from Sarcandra glabra (Thunb.) Nakai. Among them, compounds 1a and 1b were naturally occurring coumarin-phenylpropanoid conjugate enantiomers. Their structures were identified by NMR and ECD calculations. Compounds 1-8 were tested for acetylcholinesterase (AchE) inhibiting activity. The results of the enzymology experiment showed that compound 3 demonstrated obvious AchE inhibitory activity which showed the IC 50 value of 1.982 � 0.003 μM, and the binding sites were predicted by molecular docking.

Novel Bisamide Alkaloids Enantiomers from Pepper Roots (Piper nigrum L.) with Acetylcholinesterase Inhibitory and Anti-Neuroinflammatory Effects

“…The acetylcholinesterase inhibitory activities were evaluated using our previously reported method − (see the Supporting Information).…”

A comprehensive review on the chemical constituents, sesquiterpenoid biosynthesis and biological activities of Sarcandra glabra

“…Wang et al [ 82 ] reported a new coumarin, 3,5-dihydroxycoumarin-7- O -α-L-rhamnopyranosyl-2H-chromen-2-one ( 247 ), possessing anti-inflammatory properties, from S. glabra . From the stems of S. glabra , Du et al [ 83 ] uncovered the presence of five coumarins, namely, a pair of coumarin-phenylpropanoid enantiomers (7 S ,8 S ) and (7 R ,8 R )-sarcacoumarin ( 250 and 251 ) with promising acetylcholinesterase inhibitory activities, and three known compounds ( 252 – 254 ).…”

“…Isofraxidin 7- O -β-D-xylopyranosyl(1–3)-α-D-glucopyranoside C 22 H 28 O 14 BuOH 250. (7 S ,8 S )-Sarcacoumarin C 21 H 22 O 9 S. glabra, stems (Sanming, Fujian province) AcOEt [ 83 ] 251. (7 R ,8 R )-Sarcacoumarin C 21 H 22 O 9 252.…”

“…Du et al [ 83 ] recently disclosed the acetylcholinesterase (AchE) inhibiting activity of coumarins from S. glabra . Notably, 5-methoxy-6,7-methylenedioxycoumarin ( 252 ) exhibited significant AchE inhibitory efficacy (IC 50 = 1.982 ± 0.003 μM), surpassing donepezil (IC 50 = 3.118 ± 0.006 μM).…”