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Evaluation of the active functional groups and structural rearrangement of parthenolide derivatives on their potential anticancer activity

Journal name:Journal of Molecular Structure
Literature No.:
Literature Url: http://www.sciencedirect.com/science/article/pii/S0022286017300984
Date publication:5 May 2017
Two parthenolide derivatives (PDs) were synthesized by chemical modification of parthenolide with concentrated hydrochloric acid and to evaluate their cytotoxicity to Hep-G2 cells in terms of their active functional groups and polarity. The chemical structures of the PDs were characterized by Fourier transform infrared, nuclear magnetic resonance and high resolution mass spectroscopy. Two PDs (PD1 and PD2) were fractionated by silica gel column chromatography with a Rf of 0.37 and 0.19, respectively, in a 1:1 (v/v) hexane: ethyl acetate mobile phase, indicating that PD1 was less polar than PD2. Compared to the parent parthenolide, both PD1 and PD2 had lost the active carbon-carbon double bond and epoxide functional groups, but retained the active 14-methyl and α-methylene-γ-butyrolactone groups. Although PD1 and PD2 possessed similar functional groups, they differed in their structural arrangement and consequentially their polarity. PD1 and PD2 exhibited an in vitro IC50 against the Hep-G2 cell line of 41.0 and 94.0 μg/ml, respectively, which was weaker than that for parthenolide (<1 μg/ml). Thus, the ranked polarity of PD2 > PD1 > parthenolide was inversely related to their cytotoxicity against the Hep-G2 cell line (parthenolide > PD1 > PD2). The obtained PDs may be potential novel anticancer substances.

... 2. Materials and methods. 2.1. Materials. 
Parthenolides, SLs, were provided from Biopurify phytochemical company, Sichuan, China. Hydrochloric acid (HCl), sodium hydroxide (NaOH), acetone, hexane and ethyl acetate were brought from Merck, New York, USA. ...