Abstract:
In this study, six chalcones containing methyl and hydroxyl substituents at meta positions in aromatic rings; (E)-3-phenyl-1-(m-tolyl)prop-2-en-1-one (C-01), (E)-1-phenyl-3-(m-tolyl)prop-2-en-1-one (C-02), (E)-1,3-di-m-tolylprop-2-en-1-one (C-03), (E)-1-(3-hydroxyphenyl)-3-phenylprop-2-en-1-one (C-04), (E)-3-(3-hydroxyphenyl)-1-phenylprop-2-en-1-one (C-05) and (E)-1,3- (3-hydroxyphenyl) prop-2-en-1-one (C-06) were synthesised using Claisen-Schmidt reaction of substituted acetophenones and benzaldehydes at room temperature. All the synthesised compounds were characterised by spectroscopic techniques including infrared (IR), ESI-MS, UV-visible and nuclear magnetic resonance (1HNMR). The synthesised chalcones were tested for their anti-inflammatory activities using Greiss assay on mouse macrophages (RAW 264.7 cells). The results showed that presence of methyl (-CH3) and hydroxyl (-OH) substituents improved the anti-inflammatory activity of chalcones. Hydroxyl substituted chalcones showed higher anti-inflammatory activity compared to methyl substituted chalcones. Among the hydroxy-substituted chalcones, the (E)-1,3-bis (3-hydroxyphenyl) prop-2-en-1-one (C-06) was the most potent with an IC50 value lower than 6.25 μM. This compound was further tested for its influence on expression of cytokines using multianalyte ELISA array kit. This chalcone significantly reduced the elevated levels of inflammatory cytokines (IL-6, IFN-γ, TNF-α and G-CSF).
Key words: substituted chalcones, anti-inflammatory activity, cytokines, and ELISA array kit.
