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Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica
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SYSNO ASEP 0508820 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica Author(s) Rimpelová, S. (CZ)
Jurášek, M. (CZ)
Peterková, L. (CZ)
Bejček, J. (CZ)
Spiwok, V. (CZ)
Majdl, M. (CZ)
Jirásko, M. (CZ)
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Harmatha, Juraj (UOCHB-X) RID, ORCID
Kmoníčková, Eva (UEM-P) RID
Drašar, P. (CZ)
Ruml, T. (CZ)Source Title Beilstein Journal of Organic Chemistry. - : Beilstein - Institut zur Foerderung der Chemischen Wissenschaften - ISSN 1860-5397
Roč. 15, Aug 13 (2019), s. 1933-1944Number of pages 12 s. Language eng - English Country DE - Germany Keywords anti-inflammatory properties ; archangelolide ; dansyl fluorescent conjugate ; sarco/endoplasmic reticulum calcium ATPase ; sesquiterpene lactone ; trilobolide analogue Subject RIV CC - Organic Chemistry OECD category Organic chemistry Subject RIV - cooperation Institute of Experimental Medicine - Pharmacology ; Medidal Chemistry R&D Projects LO1304 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 ; UEM-P - RVO:68378041 UT WOS 000481502200002 EID SCOPUS 85071427717 DOI 10.3762/bjoc.15.189 Annotation Sesquiterpene lactones are secondary plant metabolites with sundry biological effects. In plants, they are synthesized, among others, for pesticidal and antimicrobial effects. Two such compounds, archangelolide and trilobolide of the guaianolide type, are structurally similar to the well-known and clinically tested lactone thapsigargin. While trilobolide has already been studied by us and others, there are only scarce reports on the biological activity of archangelolide. Here we present the preparation of its fluorescent derivative based on a dansyl moiety using azide-alkyne Huisgen cycloaddition having obtained the two sesquiterpene lactones from the seeds of Laserpitium archangelica Wulfen using supercritical CO2 extraction. We show that dansyl-archangelolide localizes in the endoplasmic reticulum of living cells similarly to trilobolide, localization in mitochondria was also detected. This led us to a more detailed study of the anticancer potential of archangelolide. Interestingly, we found that neither archangelolide nor its dansyl conjugate did exhibit cytotoxic effects in contrast to the structurally closely related counterparts trilobolide and thapsigargin. We explain this observation by a molecular dynamics simulation, in which, in contrast to trilobolide, archangelolide did not bind into the sarco/endoplasmic reticular calcium ATPase cavity utilized by thapsigargin. Last, but not least, archangelolide exhibited anti-inflammatory activity, which makes it promising compound for medicinal purposes. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2020 Electronic address https://www.beilstein-journals.org/bjoc/articles/15/189
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