(±)-Yanhusuomide A (1), a novel enantiomeric pair of ornithine-fused benzylisoquinoline, were characterized from the dried tubers of Corydalis yanhusuo, along with a biogenetically related intermediate oblongine (2). Yanhusuomide A features an unprecedented skeleton based on a benzylisoquinoline coupled with an ornithine derivative to form a rare 5,6-dihydro-4H-pyrido[3,4,5-de]quinazoline motif. Plausible biosynthetic pathway of 1 was proposed, and (±)-yanhusuomide A (1) presented potential inhibitory bioactivity against acetylcholinesterase (AChE) with IC = 14.07 ± 2.38 μM. The simulation of molecular docking displayed that 1 generated strong interaction with Asp-74 and Trp-86 residues of AChE through attractive charge of the quaternary nitrogen.
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| http://dx.doi.org/10.1016/j.bioorg.2023.106407 | DOI Listing |
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(±)-Yanhusuomide A, a pair of ornithine-fused benzylisoquinoline enantiomers from Corydalis yanhusuo.
Bioorg Chem
April 2023
Key Laboratory of Chinese Internal Medicine of Ministry of Education and Beijing, Dongzhimen Hospital, Beijing University of Chinese Medicine, Beijing 100700, China. Electronic address:
(±)-Yanhusuomide A (1), a novel enantiomeric pair of ornithine-fused benzylisoquinoline, were characterized from the dried tubers of Corydalis yanhusuo, along with a biogenetically related intermediate oblongine (2). Yanhusuomide A features an unprecedented skeleton based on a benzylisoquinoline coupled with an ornithine derivative to form a rare 5,6-dihydro-4H-pyrido[3,4,5-de]quinazoline motif. Plausible biosynthetic pathway of 1 was proposed, and (±)-yanhusuomide A (1) presented potential inhibitory bioactivity against acetylcholinesterase (AChE) with IC = 14.
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