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来自美丽文殊兰(Crinum × amabile Donn ex Ker Gawl.)鳞茎的具有胆碱酯酶抑制活性的生物碱

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

作者信息

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

机构信息

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.

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.

出版信息

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

DOI:10.1016/j.phytochem.2022.113473
PMID:36244402
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 (IC 0.21 μM), which was about 6-fold more active than the reference drug, galanthamine (IC 1.23 μM). Ungeremine also exhibited the strongest inhibitory activity against butyrylcholinesterase (IC 3.57 μM), which was comparable to galanthamine (IC 3.11 μM). The molecular docking studies were performed and were well in agreement with the experimental results.

摘要

从美丽文殊兰(Crinum × amabile Donn ex Ker Gawl.)的鳞茎中分离出7种此前未被描述的生物碱,即文殊兰碱A - G、2种非生物碱化合物,文殊兰二烯和6 - 苯基胡椒醇、2种首次天然存在的生物碱,3 - 表布法新碱和(+)-1β,2β - 环氧 - 表克里宁,以及19种已知生物碱。通过核磁共振(NMR)、质谱(MS)和电子圆二色光谱(ECD)技术阐明了它们的结构和绝对构型。文殊兰胺对乙酰胆碱酯酶表现出最强的抑制活性(IC50为0.21 μM),其活性约为参比药物加兰他敏(IC50为1.23 μM)的6倍。文殊兰胺对丁酰胆碱酯酶也表现出最强的抑制活性(IC50为3.57 μM),与加兰他敏(IC50为3.11 μM)相当。进行了分子对接研究,其结果与实验结果高度吻合。

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