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Volume 10
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10.3390/foods10010136
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Article

Steroid Glycosides Hyrcanoside and Deglucohyrcanoside: On Isolation, Structural Identification, and Anticancer Activity

by
Silvie Rimpelová
1,†,
Tomáš Zimmermann
2,†,
Pavel B. Drašar
2,
Bohumil Dolenský
3,
Jiří Bejček
1,
Eva Kmoníčková
4,5,
Petra Cihlářová
2,
Soňa Gurská
6,
Lucie Kuklíková
1,
Marián Hajdůch
6,
Tomáš Ruml
1,
Lubomír Opletal
7,
Petr Džubák
6,* and
Michal Jurášek
2,*
1
Department Biochemistry and Microbiology, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague, Czech Republic
2
Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague, Czech Republic
3
Department of Analytical Chemistry, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague, Czech Republic
4
Department of Pharmacology and Toxicology, Faculty of Medicine in Pilsen, Charles University, Alej Svobody 76, 323 00 Pilsen, Czech Republic
5
Department of Pharmacology, Second Faculty of Medicine, Charles University, Plzeňská 311, 150 00 Prague, Czech Republic
6
Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University and University Hospital in Olomouc, Hněvotínská 976/3, 779 00 Olomouc, Czech Republic
7
Department of Pharmaceutical Botany, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
*
Authors to whom correspondence should be addressed.
†
S.R. and T.Z. contributed equally to this work.
Foods 2021, 10(1), 136; https://doi.org/10.3390/foods10010136
Received: 14 December 2020 / Revised: 31 December 2020 / Accepted: 3 January 2021 / Published: 11 January 2021
(This article belongs to the Special Issue Isolation and Identification of Bioactive Secondary Metabolites)
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Abstract

Cardiac glycosides (CGs) represent a group of sundry compounds of natural origin. Most CGs are potent inhibitors of Na+/K+-ATPase, and some are routinely utilized in the treatment of various cardiac conditions. Biological activities of other lesser known CGs have not been fully explored yet. Interestingly, the anticancer potential of some CGs was revealed and thereby, some of these compounds are now being evaluated for drug repositioning. However, high systemic toxicity and low cancer cell selectivity of the clinically used CGs have severely limited their utilization in cancer treatment so far. Therefore, in this study, we have focused on two poorly described CGs: hyrcanoside and deglucohyrcanoside. We elaborated on their isolation, structural identification, and cytotoxicity evaluation in a panel of cancerous and noncancerous cell lines, and on their potential to induce cell cycle arrest in the G2/M phase. The activity of hyrcanoside and deglucohyrcanoside was compared to three other CGs: ouabain, digitoxin, and cymarin. Furthermore, by in silico modeling, interaction of these CGs with Na+/K+-ATPase was also studied. Hopefully, these compounds could serve not only as a research tool for Na+/K+-ATPase inhibition, but also as novel cancer therapeutics. View Full-Text
Keywords: cardiac glycosides; secondary plant metabolites; natural product isolation; hyrcanoside; deglucohyrcanoside; ouabain; cymarin; digitoxin; anticancer activity; Na+/K+-ATPase inhibitors cardiac glycosides; secondary plant metabolites; natural product isolation; hyrcanoside; deglucohyrcanoside; ouabain; cymarin; digitoxin; anticancer activity; Na+/K+-ATPase inhibitors
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

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MDPI and ACS Style

Rimpelová, S.; Zimmermann, T.; Drašar, P.B.; Dolenský, B.; Bejček, J.; Kmoníčková, E.; Cihlářová, P.; Gurská, S.; Kuklíková, L.; Hajdůch, M.; Ruml, T.; Opletal, L.; Džubák, P.; Jurášek, M. Steroid Glycosides Hyrcanoside and Deglucohyrcanoside: On Isolation, Structural Identification, and Anticancer Activity. Foods 2021, 10, 136. https://doi.org/10.3390/foods10010136

AMA Style

Rimpelová S, Zimmermann T, Drašar PB, Dolenský B, Bejček J, Kmoníčková E, Cihlářová P, Gurská S, Kuklíková L, Hajdůch M, Ruml T, Opletal L, Džubák P, Jurášek M. Steroid Glycosides Hyrcanoside and Deglucohyrcanoside: On Isolation, Structural Identification, and Anticancer Activity. Foods. 2021; 10(1):136. https://doi.org/10.3390/foods10010136

Chicago/Turabian Style

Rimpelová, Silvie, Tomáš Zimmermann, Pavel B. Drašar, Bohumil Dolenský, Jiří Bejček, Eva Kmoníčková, Petra Cihlářová, Soňa Gurská, Lucie Kuklíková, Marián Hajdůch, Tomáš Ruml, Lubomír Opletal, Petr Džubák, and Michal Jurášek. 2021. "Steroid Glycosides Hyrcanoside and Deglucohyrcanoside: On Isolation, Structural Identification, and Anticancer Activity" Foods 10, no. 1: 136. https://doi.org/10.3390/foods10010136

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