Archangelolide: Sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

Submitting author affiliation:
University of Chemistry and Technology Prague, Prague 6, Czech Republic

Beilstein Arch. 2019, 201938.

Published 04 Jun 2019

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Sesquiterpene lactones are secondary plant metabolites with sundry biological effects. In plants, they are synthesized mainly for their pesticidal, antimicrobial and other effects. Two such compounds, archangelolide and trilobolide of the guaianolide type, are structurally similar to the well-known and clinically tested lactone thapsigargin. Here we present the development of a facile method for isolation of these two sesquiterpene lactones from the seeds of Laserpitium archangelica Wulfen using supercritical CO2 extraction. Furthermore, not much has been reported on biological activity of archangelolide. We prepared its fluorescent derivative based on a dansyl moiety using azide-alkyne Huisgen cycloaddition. We showed that dansyl-archangelolide localized in endoplasmic reticulum of living cells similarly to trilobolide; nevertheless, localization in mitochondria was also detected. This led us to study the anticancer potential of archangelolide. Interestingly, we found that neither archangelolide nor its dansyl conjugate did exhibit cytotoxic effect in contrast to its 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.

Keywords: Archangelolide; Anti-inflammatory properties; Dansyl fluorescent conjugate; Sarco/endoplasmic reticulum calcium ATPase, Sesquiterpene lactone; Trilobolide analogue

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Rimpelová, S.; Jurášek, M.; Peterková, L.; Bejček, J.; Spiwok, V.; Majdl, M.; Jirásko, M.; Buděšínský, M.; Harmatha, J.; Kmoníčková, E.; Drašar, P.; Ruml, T. Beilstein Arch. 2019, 201938. doi:10.3762/bxiv.2019.38.v1

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