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Bisabololoxide derivatives from Artemisia persica, and determination of their absolute configurations by ECD

Moradi-Afrapoli, Fahimeh and Ebrahimi, Samad Nejad and Smiesko, Martin and Raith, Melanie and Zimmermann, Stefanie and Nadjafi, Farsad and Brun, Reto and Hamburger, Matthias. (2013) Bisabololoxide derivatives from Artemisia persica, and determination of their absolute configurations by ECD. Phytochemistry, Vol. 85. pp. 143-152.

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Official URL: http://edoc.unibas.ch/dok/A6083662

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Abstract

Five antiplasmodial bisabololoxide sesquiterpene diesters were isolated from an EtOAc extract of the aerial parts of Artemisia persica following an HPLC-time-based activity profiling of the extract. Structure elucidation was achieved by 1D and 2D NMR experiments. Relative configurations of cyclohexenone/cyclohexene and tetrahydropyran moieties of 1-5 were established on the basis of (3)J(H-H) coupling constants and NOE difference spectra. Stereochemical correlation of the two rings, and assignment of absolute configuration of 1-5 were achieved by comparison of experimental ECD spectra with simulated ECD data for possible stereoisomers, by using time dependent density function theory (TDDFT). Bisaboloids 1-4 exhibited in vitro antimalarial activity against Plasmodium falciparum, with IC(50) values ranging from 2.8 to 20.1μM, and selectivity indices (SI) in L-6 cells of 3.7-11.9.
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) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Ehemalige Einheiten Pharmazie > Molecular Modeling (Vedani)
UniBasel Contributors:Smiesko, Martin and Ebrahimi, Samad Nejad and Hamburger, Matthias and Raith, Melanie and Zimmermann, Stefanie and Brun, Reto and Moradiafrapoli, Fahimeh
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:Pergamon Press
ISSN:0031-9422
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:24 May 2013 09:22
Deposited On:24 May 2013 09:05

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