title: Structure-Antioxidative and Anti-Inflammatory Activity Relationships of Purpurin and Related Anthraquinones in Chemical and Cell Assays.
abstract: Anthraquinone (9,10-anthraquinone) and several hydroxy derivatives, including purpurin (1,2,4-trihydroxyanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), and chrysazin (1,8-dihydroxyanthraquinone), were evaluated for antioxidative and anti-inflammatory activities in chemical assays and mammalian cells (murine macrophage RAW 264.7 cells). Several tests were used to assess their activities: 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical; ABTS radical cation; hydrogen peroxide scavenging; reduction of potassium ferricyanide; chelation of ferrous ions; inhibition of lipid peroxidation; inhibition of nitric oxide generation; scavenging of the intracellular hydroxyl radical; expression of NLRP3 polypeptide for inflammasome assembly; and quantitation of proinflammatory cytokine interleukin 1β (IL-1β) for inflammasome activation. The results show that purpurin, from the root of the madder plant (Rubia tinctorumL.), exhibited the highest antioxidative activity in both chemical and cultured cell antioxidant assays. The antioxidative activities of the other three anthraquinones were lower than that of purpurin. In addition, purpurin could down-regulate NLRP3 inflammasome assembly and activation, suggesting that it might protect foods against oxidative damage and prevent in vivo oxidative stress and inflammation. Structure-activity relationships and the significance of the results for food quality and human health are discussed.
authors.affiliation: Department of Biological Science, Ajou University, Suwon 16499, Korea. storyhunter@ajou.ac.kr.
authors.forename: Woo
authors.initials: W
authors.lastname: Nam
authors.affiliation: Research Institute of Basic Sciences, Ajou University, Suwon 16499, Korea. sp-1108@hanmail.net.|STR Biotech. Ltd., Chuncheon 24232, Korea. sp-1108@hanmail.net.
authors.forename: Sung Phil
authors.initials: SP
authors.lastname: Kim
authors.affiliation: Department of Biological Science, Ajou University, Suwon 16499, Korea. shnam@ajou.ac.kr.
authors.forename: Seok Hyun
authors.initials: SH
authors.lastname: Nam
authors.affiliation: Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, CA 94710, USA. mendel.friedman@ars.usda.gov.
authors.forename: Mendel
authors.initials: M
authors.lastname: Friedman
mesh_terms: D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology*; D006861:Hydrogen Peroxide / Q000737:chemistry; D058847:Inflammasomes / Q000378:metabolism; D007502:Iron Chelating Agents / Q000737:chemistry / Q000494:pharmacology; D015227:Lipid Peroxidation; D008070:Lipopolysaccharides / Q000494:pharmacology; D051379:Mice; D018384:Oxidative Stress / Q000187:drug effects / Q000276:immunology; D010851:Picrates / Q000737:chemistry; D000067996:RAW 264.7 Cells; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000737:chemistry
chemical_list: D000880:Anthraquinones; D000893:Anti-Inflammatory Agents; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D058847:Inflammasomes; D007502:Iron Chelating Agents; D008070:Lipopolysaccharides; D010851:Picrates; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D006861:Hydrogen Peroxide; C004931:1,1-diphenyl-2-picrylhydrazyl; C511975:purpurin anthraquinone
keywords: BHA; anthraquinones; anti-inflammatory; antioxidant tests; cytokines; health benefits; inflammasome activation; macrophage cells; purpurin; reactive oxygen species