2. Academic Validation
  3. 5-Hydroxy-2-methylpyridine Isolated from Cigarette Smoke Condensate Aggravates Collagen-Induced Arthritis in Mice

5-Hydroxy-2-methylpyridine Isolated from Cigarette Smoke Condensate Aggravates Collagen-Induced Arthritis in Mice

  • Biol Pharm Bull. 2018;41(6):877-884. doi: 10.1248/bpb.b17-00982.
Masafumi Takeno 1,  Shinya Kitagawa 2,  Junpei Yamanaka 3,  Mayumi Teramoto 1,  Haruka Tomita 1,  Naohiro Shirai 4,  Saotomo Itoh 1,  Shigeaki Hida 1,  Kazuichi Hayakawa 5,  Kikuo Onozaki 1,  Takemasa Takii 1 6
Affiliations

Affiliations

  • 1 Department of Hygienic Chemistry, Graduated School of Pharmaceutical Sciences, Nagoya City University.
  • 2 Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology.
  • 3 Department of Physical Chemistry of Colloid and Polymer, Graduated School of Pharmaceutical Sciences, Nagoya City University.
  • 4 Department of Synthetic Supramolecular Chemistry, Graduated School of Pharmaceutical Sciences, Nagoya City University.
  • 5 Institute of Nature and Environmental Technology, Kanazawa University.
  • 6 Department of Mycobacterium Reference & Research, the Research Institute of Tuberculosis, Japan Anti-Tuberculosis Association.
PMID: 29863076 DOI: 10.1248/bpb.b17-00982
Abstract

The risk of rheumatoid arthritis (RA) is linked to environmental and genetic factors. Cigarette smoking is an established environmental risk factor for the disease that contributes to its development and severity. Previously, we found that cigarette smoke condensate (CSC), both mainstream and sidestream, aggravates Collagen type II-induced arthritis (CIA), which was observed following either intraperitoneal inoculation or nasal exposure. In the present study, we aimed to identify the compound in CSC, which aggravates CIA. By sequential fractionation and analysis, extraction with water/ether in different pH values, silica gel column chromatography, TLC, octadecyl silica (ODS) HPLC, GC/MS, and NMR, the active compound was identified as 5-hydroxy-2-methylpyridine (5H2MP). Its isomer 2-hydroxy-3-methylpyridine, but not 3-hydroxy-2-methylpyridine, was also active. 5H2MP was not mutagenic, and did not exhibit aryl hydrocarbon receptor-dependent activity. Our data help clarify the mechanism underlying the pathogenic effects of cigarette smoking on RA.

Keywords

cigarette smoke; polycyclic aromatic hydrocarbon; rheumatoid arthritis.

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