title: Synthesis and anti-inflammatory activity of indole glucosinolates.
abstract: The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassicin (NGB) in moderate overall yield for the first time. The anti-inflammatory activity of the synthetic indole GLs was determined by inhibition of TNF-α secretion in LPS-stimulated THP-1 cells. The data showed that glucobrassicin (GB) exhibited higher activity than other synthetic indolyl GLs.
authors.affiliation: Department of Chemistry, La Trobe University, Victoria 3086, Australia.
authors.forename: Quan V
authors.initials: QV
authors.lastname: Vo
authors.affiliation: Department of Primary Industries, Knoxfield Centre, 621 Burwood Highway, Knoxfield 3180, Australia.
authors.forename: Craige
authors.initials: C
authors.lastname: Trenerry
authors.affiliation: Department of Primary Industries, Victorian AgriBiosciences Centre, La Trobe University Research and Development Park, 1 Park Drive, Bundoora 3083, Victoria, Australia; La Trobe University, Victoria 3086, Australia.
authors.forename: Simone
authors.initials: S
authors.lastname: Rochfort
authors.affiliation: Department of Primary Industries, Victorian AgriBiosciences Centre, La Trobe University Research and Development Park, 1 Park Drive, Bundoora 3083, Victoria, Australia.
authors.forename: Jenny
authors.initials: J
authors.lastname: Wadeson
authors.affiliation: Department of Primary Industries, Victorian AgriBiosciences Centre, La Trobe University Research and Development Park, 1 Park Drive, Bundoora 3083, Victoria, Australia.
authors.forename: Carolina
authors.initials: C
authors.lastname: Leyton
authors.affiliation: Department of Chemistry, La Trobe University, Victoria 3086, Australia. Electronic address: tahughes@optusnet.com.au.
authors.forename: Andrew B
authors.initials: AB
authors.lastname: Hughes
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D005961:Glucosinolates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D005961:Glucosinolates; D007211:Indoles; D008070:Lipopolysaccharides; D014409:Tumor Necrosis Factor-alpha
keywords: 1,2-dimethoxyethane; 1,5-diazabicyclo [5.4.0]undecene; 4-methoxyglucobrassicin; Anti-inflammatory; Brassica; DBU; DCM; DME; DMF; DMF.DMA; ELISA; ESI; FTMS; Fourier transform mass spectrometry; GB; GLs; Glucobrassicin; HESI; HRMS; IR; Indole glucosinolates; LPS; MGB; MS; N,N-dimethylformamide; N-chlorosuccinimide; NCS; NGB; NMR; PMA; THF; TLC; TNF-α; TOMAC; UV; dichloromethane; dimethylformamide dimethyl acetal; electrospray ionization; enzyme-linked immunosorbent assay; glucobrassicin; glucosinolates; heated electrospray ionization; high resolution mass spectrometry; infra-red; lipopolysaccharides; mass spectrometry; neo-glucobrassicin; nuclear magnetic resonance; phorbol-12-myristate-13-acetate; tetrahydrofuran; thin layer chromatography; tri(n-octyl)methyl ammonium chloride; tumor necrosis factor alpha; ultra-violet