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  • Title: Bisabololoxide derivatives from Artemisia persica, and determination of their absolute configurations by ECD.
    Author: Moradi-Afrapoli F, Ebrahimi SN, Smiesko M, Raith M, Zimmermann S, Nadjafi F, Brun R, Hamburger M.
    Journal: Phytochemistry; 2013 Jan; 85():143-52. PubMed ID: 23009877.
    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 ³J(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 IC₅₀ values ranging from 2.8 to 20.1 μM, and selectivity indices (SI) in L-6 cells of 3.7-11.9.
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