Topic
Xanthone
About: Xanthone is a research topic. Over the lifetime, 1639 publications have been published within this topic receiving 25870 citations. The topic is also known as: 9-oxo-xanthene & Diphenyline ketone oxide.
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TL;DR: Results indicate that the new valuable compounds with antiarrhythmic and hypotensive activity might be found in the group of xanthone derivatives, and all studied compounds showed α1-adrenolytic properties in the in vivo and in vitro tests.
14 citations
TL;DR: Four new xanthones identified in ethanolic extract of the seeds of Rhus coriaria L. (Anacardiaceae) were active against Aspergillus flavus and known steroidal glucoside β-sitosterol-β-Dglucoside was identified.
Abstract: Phytochemical investigations of the ethanolic extract of the seeds of Rhus coriaria L. (Anacardiaceae) led to the identification of four new xanthones, characterized as 2,3-dihydroxy-7-methyl xanthone (1), 2,3,6-trihydroxy-7-hydroxymethylene xanthone-1-carboxylic acid (2), 2-methoxy-4-hydroxy-7-methyl-3-O-beta-D-glucopyranosyl xanthone-1,8-dicarboxylic acid (4), and 2-hydroxy-7-hydroxymethylene xanthone-1,8-dicarboxylic acid 3-O-beta-D-glucopyranosyl-(2'-->3")-3"-O-stigmast-5-ene (5), along with the known steroidal glucoside beta-sitosterol-beta-D-glucoside (3). The structures of the isolated compounds have been identified on the basis of spectral data analysis and chemical reactions. All xanthones were active against Aspergillus flavus.
14 citations
TL;DR: It was proved that compound 11 could induce cell apoptosis in KB cells via both extrinsic and intrinsic pathways and caused a significant and dose-dependent inhibition of topoisomerase I catalytic activity.
Abstract: A series of xanthone and thioxanthone rhamnopyranosides were designed and synthesized. Their in vitro cytotoxicity and topoisomerase inhibitory activity were evaluated. The bioassay results indicated that the introduction of the 2,3-di-O-acetyl-α-L-rhamnopyranosyl moiety to anthracene was helpful to improve the cytotoxicity in vitro. The modifications of anthracene had an important effect on the tumor cell growth inhibitory activity. Interestingly, consistency was observed between the cytotoxicity and topo I activity in these anthracene analogs, suggesting that the incorporation of either a polymethyleneamine side chain or a pyrazole ring into the anthraquinone chromophore was able to enhance topo I inhibitory activity as well as cytotoxicity simultaneously. Among them, compound 11 as a new lead compound was discovered, which showed wide in vitro cytotoxicity against 12 tumor cell lines and potential antimultidrug resistance capability. It was proved that compound 11 could induce cell apoptosis in KB cells via both extrinsic and intrinsic pathways. Flow cytometric analysis exhibited that treatment of KB cells with compound 11 led to cell apoptosis accompanied by cell cycle arrest at the G2/M phase. Furthermore, compound 11 caused a significant and dose-dependent inhibition of topoisomerase I catalytic activity.
14 citations
TL;DR: The dimeric compound and the three-side chain xanthone derivative have been shown to represent the best compounds emerging from the different series of ligands presented here, having also high selectivity for G-quadruplex structures with respect to duplex DNA.
Abstract: Following previous studies on anthraquinone and acridine-based G-quadruplex ligands, here we present a study of similar aromatic cores, with the specific aim of increasing G-quadruplex binding and selectivity with respect to duplex DNA. Synthesized compounds include two and three-side chain xanthone and xanthene derivatives, as well as a dimeric "bridged" form. ESI and FRET measurements suggest that all the studied molecules are good G-quadruplex ligands, both at telomeres and on G-quadruplex forming sequences of oncogene promoters. The dimeric compound and the three-side chain xanthone derivative have been shown to represent the best compounds emerging from the different series of ligands presented here, having also high selectivity for G-quadruplex structures with respect to duplex DNA. Molecular modeling simulations are in broad agreement with the experimental data.
14 citations
TL;DR: In this paper, the structure of the xanthone nucleus conformation is essentially planar with the substituents adopting the orientations less sterically hindered, and the classical intermolecular hydrogen bonds (O−H···O) present in III and IV give rise to infinite ribbons.
Abstract: Oxygenated xanthones have been extensively investigated over the years, but there are few reports concerning their crystal structure. Our chemical investigations of Brazilian plants resulted in the isolation of four natural products named 1-hydroxyxanthone (I), 1-hydroxy-7-methoxyxanthone (II), 1,5-dihydroxy-3-methoxyxanthone (III), and 1,7-dihydroxy-3,8-dimethoxyxanthone (IV). The structures of these compounds were established on the basis of single crystal X-ray diffraction. The xanthone nucleus conformation is essentially planar with the substituents adopting the orientations less sterically hindered. In addition, classical intermolecular hydrogen bonds (O–H···O) present in III and IV give rise to infinite ribbons. However, the xanthone I does not present any intermolecular hydrogen bonds, meanwhile the xanthone II presents only a non-classical one (C–H···O). The crystal packing of all xanthone structures is also stabilized by π–π interactions. The fingerprint plots, derived from the Hirshfeld surfaces, exhibited significant features of each crystal structures.
14 citations