title: Bisabololoxide derivatives from Artemisia persica, and determination of their absolute configurations by ECD.
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.
authors.affiliation: Department of Pharmacognosy, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
authors.forename: Fahimeh
authors.initials: F
authors.lastname: Moradi-Afrapoli
authors.forename: Samad Nejad
authors.initials: SN
authors.lastname: Ebrahimi
authors.forename: Martin
authors.initials: M
authors.lastname: Smiesko
authors.forename: Melanie
authors.initials: M
authors.lastname: Raith
authors.forename: Stefanie
authors.initials: S
authors.lastname: Zimmermann
authors.forename: Farsad
authors.initials: F
authors.lastname: Nadjafi
authors.forename: Reto
authors.initials: R
authors.lastname: Brun
authors.forename: Matthias
authors.initials: M
authors.lastname: Hamburger
mesh_terms: D000962:Antimalarials / Q000737:chemistry* / Q000494:pharmacology*; D019306:Artemisia / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects*
chemical_list: D000962:Antimalarials; D010936:Plant Extracts