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Unusual derivatives from Hypericum scabrum

Soroury, Sara and Alilou, Mostafa and Gelbrich, Thomas and Tabefam, Marzieh and Danton, Ombeline and Ebrahimi, Samad N. and Kaiser, Marcel and Hamburger, Matthias and Stuppner, Hermann and Farimani, Mahdi Moridi. (2020) Unusual derivatives from Hypericum scabrum. Scientific Reports, 10. p. 22181.

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Official URL: https://edoc.unibas.ch/80982/

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Abstract

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-[4.3.1.11,4]-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 μM, respectively.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Pharmazeutische Biologie (Hamburger)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
UniBasel Contributors:Hamburger, Matthias and Danton, Ombeline Réjane and Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Nature Publishing Group
e-ISSN:2045-2322
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:13 Apr 2021 13:22
Deposited On:13 Apr 2021 13:22

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