4 5 di o caffeoylquinic acid

Ethanol (99.9%), acetonitrile (99.9%) and formic acid (98–100%) were purchased from Thermo Fisher, (Illkirch, France). Ultra-pure water was obtained from a Milli-Q system (Millipore Corporation, Burlington, MA, USA). DPPH (2,2-Diphenyl-picrylhydrazyl) and Trolox^® (6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid) were obtained from VWR, France. 3-O-caffeoylquinic acid standard (>98%) was purchased from TCI CHEMICALS (Zwijndrecht, Belgium); 4,5-di-O-caffeoylquinic acid (>90%) and 3,5-di-O-caffeoylquinic acid (>90%) were purchased from Sigma-Aldrich (Saint-Quentin-Fallavier, France).

4,5-di-O-caffeoylquinic acid (solubility: 5 mg/mL in DMSO, ≥85% (LC/MS-ELSD), product number: SMB00221), Carrageenan, sulfanilamide, N-(1-naphthyl) ethylenediamine dihydrochloride, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), and phosphoric acid were purchased from Sigma-Aldrich (St. Louis, MO, USA). The ACAN ELISA kit was purchased from MyBioSource (San Diego, CA, USA), whereas the prostaglandin E2 (PGE₂) ELISA kit was purchased from R&D Systems (Minneapolis, MN, USA). IL-1β was purchased from ProSpec Protein Specialists (Rehovot, Israel). Collagenase type 2 was purchased from Worthington Biochemical Corporation (Lakewood, NJ, USA). Dulbecco’s modified Eagle’s medium/Nutrient mixture F-12 (DMEM/F12) and penicillin–streptomycin solution were purchased from WelGene (Daegu, Korea). Fetal bovine serum (FBS) was purchased from ATLAS Biologicals (Fort Collins, CO, USA). Primary and secondary antibodies for MMP-13, ADAMTS-4, and iNOS (Abcam, Cambridge, MA, USA); anti-α-tubulin (Thermo Fisher Scientific, Waltham, MA, USA); MMP-1 (Lifespan Biosciences, Seattle, WA, USA), MMP-3, COX-2, and TNF-α (Cell Signaling Technology, Danvers, MA, USA); p-IκB-α, IκB-α, and NF-κB (Invitrogen, Carlsbad, Germany); and PCNA (Santa Cruz Biotechnology, Inc., Dallas, TX, USA) were also purchased.