title: Synthesis and biological activities of 2,6-dihydroxy-4-isopentenyloxychalcone as an antimicrobial and anti-inflammatory compound.
abstract: Chalcones are a group of plant-derived polyphenolic compounds possessing a wide variety of biological activities. The aim of this study was to synthesize 2,6-dihydroxy-4-isopentenyloxychalcone (1), a chalcone found in plants belonging to the genera Helichrysum, Pleiotaxix and Metalasia, and evaluate its antimicrobial effects against major oral pathogens as well as its anti-inflammatory properties. Compound 1 was synthesized using a simple two-step procedure. Among the seven pathogens tested, Porphyromonas gingivalis and Prevotella intermedia were the most susceptible to inhibition by 1. This chalcone also attenuated the secretion of interleukin-8 and chemokine (C-C motif) ligand 5 (CCL5) by lipopolysaccharide (LPS)-stimulated oral epithelial cells as well as the secretion of matrix metalloproteinase 2 (MMP-2) by LPS-stimulated gingival fibroblasts. In conclusion, our study showed that 1 exerts a dual effect by acting on both oral pathogens and the host inflammatory response and thus represents a molecule of interest for periodontal infections.
authors.forename: Laetitia
authors.initials: L
authors.lastname: Bonifait
authors.forename: Lei
authors.initials: L
authors.lastname: Zhao
authors.forename: Jabrane
authors.initials: J
authors.lastname: Azelmat
authors.forename: Salvatore
authors.initials: S
authors.lastname: Genovese
authors.forename: Francesco
authors.initials: F
authors.lastname: Epifano
authors.affiliation: Groupe de Recherche en Ecologie Buccale, Faculte de Medecine Dentaire, Universite Laval, 2420 rue de la Terrasse, Quebec City, QC, G1V0A6, Canada. Daniel.Grenier@greb.ulaval.ca.
authors.forename: Daniel
authors.initials: D
authors.lastname: Grenier
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018946:Chemokine CCL5 / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D004847:Epithelial Cells / Q000187:drug effects / Q000378:metabolism; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D016209:Interleukin-8 / Q000378:metabolism; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D020778:Matrix Metalloproteinase 2 / Q000378:metabolism; D015394:Molecular Structure; D016966:Porphyromonas gingivalis / Q000187:drug effects* / Q000378:metabolism; D018713:Prevotella intermedia / Q000187:drug effects* / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: C000593046:2,6-dihydroxy-4-Isopentenyloxychalcone; D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; C483024:CCL5 protein, human; D047188:Chalcones; D018946:Chemokine CCL5; D016209:Interleukin-8; D008070:Lipopolysaccharides; D020778:Matrix Metalloproteinase 2