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An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C(1), stipulin(2), crotaorixin(3), medicagenin(4), licoagrochalcone A(5) and abyssinone D(6) along with the pyranochalcones paratocarpin C(7), anthyllisone(8) and 3-O-methylabyssinone A(9).The key step of the synthesis is a Claisen–Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides(LPSs)-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5(IC_(50)= 10.41 μmol/L), 6(IC_(50)= 9.65 μmol/L) and 8(IC_(50)= 15.34 μmol/L) show remarkable activity with no cytotoxicity. Compound 9(IC_(50)= 4.5 μmol/L)exhibits maximum(83.6%) nitric oxide(NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A(acetophenone moiety), i.e.,1–4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B(aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.
An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. Kanzonol C (1), stipulin (2), crotaorixin (3), medicagenin (4), licoagrochalcone A (5) and abyssinone D the pyranochalcones paratocarpin C (7), anthyllisone (8) and 3-O-methylabyssinone A (9). The key step of the synthesis is a Claisen-Schmidt condensation. Ofinduced RAW 264.7 macrophages Of the synthesized chalcones compounds 5 IC50 = ) show remarkable activity with no cytotoxicity. Compound 9 (IC 50 = 4.5 μmol / L) exhibits maximum (83.6%) nitric oxide (NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and / or 5-position on ring A (acetophenone moiety), ie, 1-4 and 7 show weak, or no inhibition activity, while chalcones having the prenyl group on ly on ring B (aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.