Unusual derivatives from Hypericum scabrum

Soroury, S. and Alilou, M. and Gelbrich, T. and Tabefam, M. and Danton, O. and Ebrahimi, S. N. and Kaiser, M. and Hamburger, M. and Stuppner, H. and Moridi Farimani, M.. (2020) Unusual derivatives from Hypericum scabrum. Scientific Reports, 10. p. 22181.

[img] PDF - Published Version
Available under License CC BY (Attribution).


Official URL: https://edoc.unibas.ch/91233/

Downloads: Statistics Overview


Three new compounds (1-3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[,4)]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1-3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 muM, respectively.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel and Hamburger, Matthias and Danton, Ombeline Réjane
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Nature Publishing Group
Note:Publication type according to Uni Basel Research Database: Journal article
Related URLs:
Identification Number:
edoc DOI:
Last Modified:26 Jul 2023 08:08
Deposited On:29 Dec 2022 10:03

Repository Staff Only: item control page