title: Novel stilbenoids, including cannabispiradienone glycosides, from Tragopogon tommasinii (Asteraceae, Cichorieae) and their potential anti-inflammatory activity.
abstract: A phytochemical investigation of Tragopogon tommasinii Sch.Bip. (Asteraceae, Cichorieae) yielded a total of 21 natural products, two simple phenolic acids (4-hydroxybenzoic acid and p-coumaric acid), four caffeic acid derivatives (chlorogenic acid, 3-O-caffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, and 4,5-O-dicaffeoylquinic acid), six flavonoids (luteolin, luteolin 7-O-glucoside, vitexin, orientin, quercetin 3-O-glucoside, and isorhamnetin 3-O-glucoside), three simple bibenzyls [2-carboxyl-5-hydroxy-3-methoxy-4'-β-glucopyranosyl-oxybibenzyl, 3-caffeoyl-(9→5)-β-apiosyl-(1→6)-β-glucopyranosyloxy-5,4'-dihydroxy-3'-methoxybibenzyl, 3-caffeoyl-(9→5)-β-apiosyl-(1→6)-β-glucopyranosyloxy-4'-dihydroxy-5,3'-dimethoxybibenzyl], three phtalides [3-(4-β-glucopyranosyloxybenzyl)-7-hydroxy-5-methoxyphtalide, 7-β-glucopyranosyloxy-(S)-3-(4-hydroxybenzyl)-5-methoxyphtalide, and 7-(1→6)-α-rhamnosyl-β-glucopyranosyloxy-(S)-3-(4-hydroxybenzyl)-5-methoxyphtalide], two cannabispiradienone derivatives [3-O-β-glucopyranosyldemethoxycannabispiradienone and 3-caffeoyl-(9→5)-β-apiosyl-(1→6)-β-glucopyranosyloxydemethoxycannabispiradienone], and tetra-N-coumaroyl spermine. The three bibenzyls, the latter two benzylphthalides, and both cannabispiradienone derivatives represent new natural compounds and all compounds, except the caffeic acid derivatives and the flavonoids were new for T. tommasinii. The structures were established by HR mass spectrometry, extensive 1D and 2D NMR spectroscopy, and CD spectroscopy. Moreover, the potential anti-inflammatory activities of the new compounds were assayed using human neutrophils and their production of IL-1b, IL-8, TNF-α and MMP-9 as well as the expression of TLR-4, respectively.
authors.affiliation: Department of Pharmacognosy and Molecular Basis of Phytotherapy, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, Poland; Institute of Pharmacy, Department of Pharmacognosy, University of Innsbruck, CCB, Innrain 80-82, Innsbruck, Austria.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Granica
authors.affiliation: Department of Pharmacognosy and Molecular Basis of Phytotherapy, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, Poland.
authors.forename: Jakub P
authors.initials: JP
authors.lastname: Piwowarski
authors.affiliation: Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Napoli (NA), Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Randazzo
authors.affiliation: Institute of Pharmacy, Department of Pharmacognosy, University of Innsbruck, CCB, Innrain 80-82, Innsbruck, Austria.
authors.forename: Peter
authors.initials: P
authors.lastname: Schneider
authors.affiliation: Department of Pharmacodynamics, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1b, 02-097 Warsaw, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Żyżyńska-Granica
authors.affiliation: Institute of Pharmacy, Department of Pharmacognosy, University of Innsbruck, CCB, Innrain 80-82, Innsbruck, Austria. Electronic address: Christian.H.Zidorn@uibk.ac.at.
authors.forename: Christian
authors.initials: C
authors.lastname: Zidorn
mesh_terms: D000328:Adult; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology*; D002478:Cells, Cultured; D002942:Circular Dichroism; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry; D006801:Humans; D016209:Interleukin-8 / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects / Q000378:metabolism; D013141:Spiro Compounds / Q000737:chemistry / Q000494:pharmacology; D051197:Toll-Like Receptor 4 / Q000378:metabolism; D031188:Tragopogon / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism
chemical_list: D000893:Anti-Inflammatory Agents; D005419:Flavonoids; D005960:Glucosides; D006027:Glycosides; D016209:Interleukin-8; D013141:Spiro Compounds; C495345:TLR4 protein, human; D051197:Toll-Like Receptor 4; D014409:Tumor Necrosis Factor-alpha
keywords: Asteraceae; Stilbenoids; Subtribe Scorzonerinae; Tragopogon; Tribe Cichorieae