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Updated: May 18, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Bisabololoxide derivatives from Artemisia persica, and determination of their absolute configurations by ECD
Fahimeh Moradi-Afrapoli1, Samad Nejad Ebrahimi, Martin Smiesko
1Department of Pharmacognosy, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
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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