Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00508820" target="_blank" >RIV/61388963:_____/19:00508820 - isvavai.cz</a>

Alternative codes found

RIV/68378041:_____/19:00508820 RIV/00216208:11140/19:10399959 RIV/60461373:22330/19:43918915 RIV/60461373:22320/19:43918915

Result on the web

<a href="https://www.beilstein-journals.org/bjoc/articles/15/189" target="_blank" >https://www.beilstein-journals.org/bjoc/articles/15/189</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3762/bjoc.15.189" target="_blank" >10.3762/bjoc.15.189</a>

Result language

angličtina

Original language name

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

Original language description

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.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2019

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Beilstein Journal of Organic Chemistry

ISSN

1860-5397

e-ISSN

—

Volume of the periodical

15

Issue of the periodical within the volume

Aug 13

Country of publishing house

DE - GERMANY

Number of pages

12

Pages from-to

1933-1944

UT code for WoS article

000481502200002

EID of the result in the Scopus database

2-s2.0-85071427717