Ormosianines A–P, Structurally Diverse Quinolizidine Alkaloids with AChE Inhibitory Effects from Ormosia yunnanensis

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-08-17 DOI:10.1021/acs.jnatprod.3c00493

Qiong Jin, Xu-Jie Qin, Wen-Jie Sun, Xiao Ding, Yun Zhao, Chang-Bin Wang, Xing-Yu Tao and Xiao-Dong Luo*,

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Abstract

Sixteen new quinolizidine alkaloids (QAs), named ormosianines A–P (1–16), and 18 known congeners (17–34) were isolated from the stems and leaves of Ormosia yunnanensis. The structures were elucidated based on spectroscopic analyses and electron circular dichroism (ECD) calculations. Structurally, ormosianines A (1) and B (2) are the first examples of cytisine and Ormosia-type alkaloids with the cleavage of the piperidine ring. Results of the acetylcholinesterase (AChE) inhibitory assay revealed that the pentacycline Ormosia-type QAs, including 1, 16, 24, and 27–29, are good AChE inhibitors. Ormosianine A (1) exhibited more potent AChE inhibitory activity with an IC₅₀ value of 1.55 μM. Molecular docking revealed that 1 might bind to the protein 1DX4, forming two hydrogen bonds with residues SER-238 and HIS-480.

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云南Ormosia中具有AChE抑制作用的结构多样的喹啉生物碱A–P

从云南红豆茎叶中分离到16种新的喹啉类生物碱，命名为红豆苷A–P（1–16）和18种已知的同源物（17–34）。基于光谱分析和电子圆二色性（ECD）计算阐明了它们的结构。从结构上讲，ormosianines A（1）和B（2）是具有哌啶环断裂的胞嘧啶和Ormosia型生物碱的第一个实例。乙酰胆碱酯酶（AChE）抑制试验结果表明，包括1、16、24和27-29在内的五环素Ormosia型QA是良好的AChE抑制剂。Ormosinine A（1）对AChE的抑制作用更强，IC50为1.55μM。分子对接显示，1可能与蛋白质1DX4结合，与残基SER-238和HIS-480形成两个氢键。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.