Discovery of Guanidine Derivatives from Buthus martensii Karsch with Metal-Binding and Cholinesterase Inhibition Properties

Two rare guanidine-type alkaloids, Buthutin A (1) and Buthutin B (2), along with two other compounds (3, 4), were isolated from Buthus martensii Karsch, and determined using extensive spectroscopic data an...

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Autores principales:	Yu-Ming Liu, Jing-Jing Fan, Li-Ning Wang
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Buthus martensii</i> Karsch cholinesterase inhibitor guanidine-type alkaloid metal-binding molecular docking Alzheimer’s disease (AD) Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/db96771a920a426bb04458520b1c6d77
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spelling	oai:doaj.org-article:db96771a920a426bb04458520b1c6d772021-11-11T18:40:16ZDiscovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties10.3390/molecules262167371420-3049https://doaj.org/article/db96771a920a426bb04458520b1c6d772021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6737https://doaj.org/toc/1420-3049Two rare guanidine-type alkaloids, Buthutin A (<b>1</b>) and Buthutin B (<b>2</b>), along with two other compounds (<b>3</b>, <b>4</b>), were isolated from <i>Buthus martensii</i> Karsch, and determined using extensive spectroscopic data analysis and high resolution-mass spectrometry. Compound <b>1</b> showed the most potent inhibition on AChE and BChE with IC<sub>50</sub> values of 7.83 ± 0.06 and 47.44 ± 0.95 μM, respectively. Kinetic characterization of compound <b>1</b> confirmed a mixed-type of AChE inhibition mechanism in accordance with the docking results, which shows its interaction with both catalytic active (CAS) and peripheral anionic (PAS) sites. The specific binding of compound <b>1</b> to PAS domain of AChE was also confirmed experimentally. Moreover, compounds <b>1</b> and <b>3</b> exhibited satisfactory biometal binding abilities toward Cu<sup>2+</sup>, Fe<sup>2+</sup>, Zn<sup>2+</sup> and Al<sup>3+</sup> ions. These results provide a new evidence for further development and utilization of <i>B. martensii</i> in health and pharmaceutical products.Yu-Ming LiuJing-Jing FanLi-Ning WangMDPI AGarticle<i>Buthus martensii</i> Karschcholinesterase inhibitorguanidine-type alkaloidmetal-bindingmolecular dockingAlzheimer’s disease (AD)Organic chemistryQD241-441ENMolecules, Vol 26, Iss 6737, p 6737 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Buthus martensii</i> Karsch cholinesterase inhibitor guanidine-type alkaloid metal-binding molecular docking Alzheimer’s disease (AD) Organic chemistry QD241-441
spellingShingle	<i>Buthus martensii</i> Karsch cholinesterase inhibitor guanidine-type alkaloid metal-binding molecular docking Alzheimer’s disease (AD) Organic chemistry QD241-441 Yu-Ming Liu Jing-Jing Fan Li-Ning Wang Discovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties
description	Two rare guanidine-type alkaloids, Buthutin A (<b>1</b>) and Buthutin B (<b>2</b>), along with two other compounds (<b>3</b>, <b>4</b>), were isolated from <i>Buthus martensii</i> Karsch, and determined using extensive spectroscopic data analysis and high resolution-mass spectrometry. Compound <b>1</b> showed the most potent inhibition on AChE and BChE with IC<sub>50</sub> values of 7.83 ± 0.06 and 47.44 ± 0.95 μM, respectively. Kinetic characterization of compound <b>1</b> confirmed a mixed-type of AChE inhibition mechanism in accordance with the docking results, which shows its interaction with both catalytic active (CAS) and peripheral anionic (PAS) sites. The specific binding of compound <b>1</b> to PAS domain of AChE was also confirmed experimentally. Moreover, compounds <b>1</b> and <b>3</b> exhibited satisfactory biometal binding abilities toward Cu<sup>2+</sup>, Fe<sup>2+</sup>, Zn<sup>2+</sup> and Al<sup>3+</sup> ions. These results provide a new evidence for further development and utilization of <i>B. martensii</i> in health and pharmaceutical products.
format	article
author	Yu-Ming Liu Jing-Jing Fan Li-Ning Wang
author_facet	Yu-Ming Liu Jing-Jing Fan Li-Ning Wang
author_sort	Yu-Ming Liu
title	Discovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties
title_short	Discovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties
title_full	Discovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties
title_fullStr	Discovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties
title_full_unstemmed	Discovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties
title_sort	discovery of guanidine derivatives from <i>buthus martensii</i> karsch with metal-binding and cholinesterase inhibition properties
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/db96771a920a426bb04458520b1c6d77
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Discovery of Guanidine Derivatives from <i>Buthus martensii</i> Karsch with Metal-Binding and Cholinesterase Inhibition Properties

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