Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities

In view of the abundant evidence that Lycopodiaceae alkaloids, including the well-known huperzine A (HupA), are among the potent acetylcholinesterase (AChE) inhibitors, an attempt was made to search for new compounds responsible for this property. For this purpose, three plant species belonging to t...

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Autores principales:	Aleksandra Dymek, Jarosław Widelski, Krzysztof Kamil Wojtanowski, Vladyslav Vivcharenko, Agata Przekora, Tomasz Mroczek
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Lycopodium</i> <i>clavatum</i> L. <i>Lycopodium annotinum</i> L. <i>Huperzia</i> <i>selago</i> L. <i>Lycopodiaceae</i> AChE inhibitors alkaloids Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/f3b4f8f6e7c04c4c83370376e86f1ec1
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spelling	oai:doaj.org-article:f3b4f8f6e7c04c4c83370376e86f1ec12021-11-11T18:24:27ZFractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities10.3390/molecules262163791420-3049https://doaj.org/article/f3b4f8f6e7c04c4c83370376e86f1ec12021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6379https://doaj.org/toc/1420-3049In view of the abundant evidence that Lycopodiaceae alkaloids, including the well-known huperzine A (HupA), are among the potent acetylcholinesterase (AChE) inhibitors, an attempt was made to search for new compounds responsible for this property. For this purpose, three plant species belonging to the Lycopodiaceae family, commonly found in the Euro-Asia region, were subjected to the isolation of bioactive compounds, their identification and subsequent evaluation of their anticholinesterase and cytotoxic activities. Methanolic extracts of two <i>Lycopodium</i> and one <i>Hupezia</i> species were obtained via optimized pressurized liquid extraction (PLE) and then pre-purified using innovative gradient vacuum liquid chromatography (gVLC). For the first time, three sorbents of different porosity packed in polypropylene cartridges and mobile phase systems of different polarity were used to elute the target compounds. This technique proved to be a rapid tool for the obtainment of alkaloid fractions and allowed one to select the appropriate process conditions to yield potent AChE inhibitors in each of the species studied. More than 100 collected fractions were analyzed via HPLC/ESI-QTOF-MS, which enabled one to detect more than 50 compounds, including several new ones previously unreported. Some of them were present in high purity fractions (60–90% of the established purity). TLC bioautography assays proved that the analyzed species are rich sources of AChE inhibitors, but <i>H. selago</i> showed the highest anti-AChE activity. Additionally, the modified silanized silica gel sorbent used allowed one to isolate <i>L. clavatum</i> alkaloids more efficiently using an aqueous reversed-phase solvent system. Furthermore, the tested extracts from the three plant extracts were found to be safe, as they did not exhibit cytotoxicity to skin fibroblasts.Aleksandra DymekJarosław WidelskiKrzysztof Kamil WojtanowskiVladyslav VivcharenkoAgata PrzekoraTomasz MroczekMDPI AGarticle<i>Lycopodium</i> <i>clavatum</i> L.<i>Lycopodium annotinum</i> L.<i>Huperzia</i> <i>selago</i> L.<i>Lycopodiaceae</i>AChE inhibitorsalkaloidsOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6379, p 6379 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Lycopodium</i> <i>clavatum</i> L. <i>Lycopodium annotinum</i> L. <i>Huperzia</i> <i>selago</i> L. <i>Lycopodiaceae</i> AChE inhibitors alkaloids Organic chemistry QD241-441
spellingShingle	<i>Lycopodium</i> <i>clavatum</i> L. <i>Lycopodium annotinum</i> L. <i>Huperzia</i> <i>selago</i> L. <i>Lycopodiaceae</i> AChE inhibitors alkaloids Organic chemistry QD241-441 Aleksandra Dymek Jarosław Widelski Krzysztof Kamil Wojtanowski Vladyslav Vivcharenko Agata Przekora Tomasz Mroczek Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities
description	In view of the abundant evidence that Lycopodiaceae alkaloids, including the well-known huperzine A (HupA), are among the potent acetylcholinesterase (AChE) inhibitors, an attempt was made to search for new compounds responsible for this property. For this purpose, three plant species belonging to the Lycopodiaceae family, commonly found in the Euro-Asia region, were subjected to the isolation of bioactive compounds, their identification and subsequent evaluation of their anticholinesterase and cytotoxic activities. Methanolic extracts of two <i>Lycopodium</i> and one <i>Hupezia</i> species were obtained via optimized pressurized liquid extraction (PLE) and then pre-purified using innovative gradient vacuum liquid chromatography (gVLC). For the first time, three sorbents of different porosity packed in polypropylene cartridges and mobile phase systems of different polarity were used to elute the target compounds. This technique proved to be a rapid tool for the obtainment of alkaloid fractions and allowed one to select the appropriate process conditions to yield potent AChE inhibitors in each of the species studied. More than 100 collected fractions were analyzed via HPLC/ESI-QTOF-MS, which enabled one to detect more than 50 compounds, including several new ones previously unreported. Some of them were present in high purity fractions (60–90% of the established purity). TLC bioautography assays proved that the analyzed species are rich sources of AChE inhibitors, but <i>H. selago</i> showed the highest anti-AChE activity. Additionally, the modified silanized silica gel sorbent used allowed one to isolate <i>L. clavatum</i> alkaloids more efficiently using an aqueous reversed-phase solvent system. Furthermore, the tested extracts from the three plant extracts were found to be safe, as they did not exhibit cytotoxicity to skin fibroblasts.
format	article
author	Aleksandra Dymek Jarosław Widelski Krzysztof Kamil Wojtanowski Vladyslav Vivcharenko Agata Przekora Tomasz Mroczek
author_facet	Aleksandra Dymek Jarosław Widelski Krzysztof Kamil Wojtanowski Vladyslav Vivcharenko Agata Przekora Tomasz Mroczek
author_sort	Aleksandra Dymek
title	Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities
title_short	Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities
title_full	Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities
title_fullStr	Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities
title_full_unstemmed	Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities
title_sort	fractionation of lycopodiaceae alkaloids and evaluation of their anticholinesterase and cytotoxic activities
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/f3b4f8f6e7c04c4c83370376e86f1ec1
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Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities

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