AUTHOR=Wang Lingyan , Xia Huan , Wu Yuzhuo , Wang Yanan , Lin Pengcheng , Lin Sheng 

TITLE=Secoyanhusamine A, an Oxidatively Ring-Opened Isoquinoline Inner Salt From Corydalis yanhusuo

JOURNAL=Frontiers in Chemistry

VOLUME=9

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2021.831173

DOI=10.3389/fchem.2021.831173

ISSN=2296-2646

ABSTRACT=<p>Secoyanhusamine A (<bold>1</bold>), a rare rearranged <italic>seco</italic>-isoquinoline alkaloid derived from ring oxidative cleavage, was isolated from an aqueous extract of <italic>Corydalis yanhusuo</italic> tubers, together with its biosynthetic precursor dehydrocorybulbine (<bold>2</bold>). Secoyanhusamine A (<bold>1</bold>) was the first example of a highly oxidized isoquinoline inner salt resulting in a 5-(2-azanylethyl)-2-carboxylate-4-oxo-4<italic>H</italic>-pyran ring system. The biosynthetic pathway of <bold>1</bold> was also postulated. Secoyanhusamine A (<bold>1</bold>) exhibited potent inhibition against acetylcholinesterase (AChE) with an IC<sub>50</sub> value of 0.81 ± 0.13 <italic>μ</italic>M. Molecular simulation docking demonstrated that <bold>1</bold> created a strong interaction with the Asp-74 residue of AChE <italic>via</italic> attractive charge of the quaternary nitrogen.</p>