ANTI-ALLERGIC EFFECTS OF 1,5-BIS(4’-HYDROXY-3’-METHOXYPHENYL)-1,4-PENTADIENE-3-ONE ON MAST CELL-MEDIATED ALLERGY MODEL

1,5-bis(4’-hydroxy-3’-methoxyphenyl)-1,4-pentadiene-3-one is a 1,5-diphenyl-1,4-pentadiene-3-one analogue of curcumin that is produced by modifying the middle site of curcumin leading to 1,4-pentadiene-3-ones to maintain the hydroxy moiety at the aromatic rings that are responsible for its biological activities. Curcumin has been reported to have anti-allergic effects and can inhibit the release of histamine from mast cells. In the present study, we evaluated the anti-allergic effects of 1,5-bis(4’-hydroxy-3’-methoxyphenyl)-1,4-pentadiene-3-one in a mast cell-mediated allergy mode in order to provide information about a newly synthesised-compound for an alternative allergy drug. The study was performed using (1) a rat basophilic leukaemia (RBL-2H3) cell line, which is a tumour analogue of mast cells, with DNP24-BSA, thapsigargin and ionomycin as inducers for secretory markers from mast cells, and (2) an active cutaneous anaphylaxis (ACA) reaction, with ovalbumin as an inductor of mast cell degranulation. Treatment with 1,5-bis(4’-hydroxy-3’-methoxyphenyl)-1,4-pentadiene-3-one strongly inhibited the DNP24-BSA, thapsigargin and ionomycin-mediated release of histamine and β-hexosaminidase from the RBL-2H3 cell line. The results indicated that this compound influenced the activation processes of FcεRI by antigen and intracellular Ca2+ signalling events in mast cells. In type 1 allergy model, this compound also inhibited the active cutaneous anaphylactic reaction on rat dorsal skins generated by ovalbumin. We conclude that the compound 1,5-bis(4’-hydroxy-3’-methoxyphenyl)-1,4-pentadiene-3-one showed anti-allergic activities mediated by mechanisms related to intracellular signalling events in mast cells.