Novel stilbenoids, including cannabispiradienone glycosides, from Tragopogon tommasinii (Asteraceae, Cichorieae) and their potential anti-inflammatory activity

Granica, Sebastian, Piwowarski, Jakub P., Randazzo, Antonio, Schneider, Peter, Żyżyńska-Granica, Barbara and Zidorn, Christian (2015) Novel stilbenoids, including cannabispiradienone glycosides, from Tragopogon tommasinii (Asteraceae, Cichorieae) and their potential anti-inflammatory activity Phytochemistry, 117 . pp. 254-266. DOI 10.1016/j.phytochem.2015.06.018.

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Supplementary data:

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.

Document Type: Article
Research affiliation: Kiel University > Kiel Marine Science
Refereed: Yes
DOI etc.: 10.1016/j.phytochem.2015.06.018
ISSN: 0031-9422
Date Deposited: 29 Jun 2017 08:40
Last Modified: 01 Feb 2018 13:29
URI: http://eprints.uni-kiel.de/id/eprint/38652

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