title: Systematic synthesis and anti-inflammatory activity of ω-carboxylated menaquinone derivatives--Investigations on identified and putative vitamin K₂ metabolites.
abstract: Vitamin K is an essential nutrient for blood coagulation and bone homeostasis, and also functions in many physiological processes including inflammation and cancer progression. However, the nature and activities of its metabolites remain unclear. We report here systematic synthesis of ω-carboxylated derivatives of menaquinone (vitamin K2), including previously identified metabolites 5, K acid I (10), and K acid II (12), and evaluation of their inhibitory activity toward LPS-stimulated induction of inflammatory cytokines. These results should contribute to an improved understanding of the biochemistry and pharmacology of vitamin K.
authors: Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan; Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, 113-0032 Tokyo, Japan.
authors: Shinya
authors: S
authors: Fujii
authors: Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
authors: Akitaka
authors: A
authors: Shimizu
authors: Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
authors: Noriaki
authors: N
authors: Takeda
authors: Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
authors: Kazuki
authors: K
authors: Oguchi
authors: Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
authors: Tomoko
authors: T
authors: Katsurai
authors: Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
authors: Hitoshi
authors: H
authors: Shirakawa
authors: Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
authors: Michio
authors: M
authors: Komai
authors: Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan. Electronic address: kage.chem@tmd.ac.jp.
authors: Hiroyuki
authors: H
authors: Kagechika
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001711:Biotransformation; D002264:Carboxylic Acids / Q000737:chemistry*; D007249:Inflammation / Q000517:prevention & control; D053583:Interleukin-1beta / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D015850:Interleukin-6 / Q000096:biosynthesis; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D008264:Macrophages / Q000166:cytology / Q000187:drug effects / Q000276:immunology; D051379:Mice; D009281:Naphthalenes / Q000737:chemistry; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D024482:Vitamin K 2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D000093242:Interleukin-6 Inhibitors
chemical_list: D000893:Anti-Inflammatory Agents; D002264:Carboxylic Acids; D053583:Interleukin-1beta; D015850:Interleukin-6; D008070:Lipopolysaccharides; D009281:Naphthalenes; D014409:Tumor Necrosis Factor-alpha; D024482:Vitamin K 2; D000093242:Interleukin-6 Inhibitors; C577686:interleukin-6, mouse
keywords: Anti-inflammatory activity; Menaquinone; Metabolite; Vitamin K