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In the course of a phytochemical study of the bitter tonic plant, small centaury (Centaurium erythraea), six methoxylated xanthones (1,5-hydroxy-3-methoxyxanthone, 1-hydroxy-3,5,6-trimethoxyxanthone, 1-hydroxy-3,5,6,7-tetramethoxyxanthone, 1-hydroxy-3,5,6,7,8-pentamethoxyxanthone, 1-hydroxy-3,7,8-trimethoxyxanthone and 1,8-dihydroxy-3,5,6,7-tetramethoxyxanthone) were isolated and identified by spectroscopic means (nuclear magnetic resonance, mass spectroscopy, and UV). Subsequently, a high-performance liquid chromatography/diode array detection method was developed for the determination of these and other methoxylated xanthones occurring in the chloroform extract of small centaury aerial parts. The methodology developed was applied to twelve samples, and in all of them, nine xanthones were identified and quantified. This methodology can be considered complimentary to the one proposed by the European Pharmacopoeia.
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http://dx.doi.org/10.1021/jf0109571 | DOI Listing |
Int J Biol Macromol
August 2025
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, 23890-000 Seropedica, Rio de Janeiro, Brazil. Electronic address:
The synthetic 1-methoxyxanthone, 2-methoxyxanthone, and 4-methoxyxanthone (compounds 1, 2, and 3, respectively) were tested against amastigotes of Trypanosoma cruzi (C2C4, LacZ), showing an activity profile that depends on the position of the methoxy group in the xanthone ring, targeting pteridine reductase 1 of T. cruzi (TcPTR1). The initial pharmacokinetic assessment involved biophysical characterization of the interaction between the xanthones and human serum albumin (HSA, the main globular protein responsible for drug distribution), using circular dichroism (CD), steady-state and time-resolved fluorescence measurements, combined with in silico calculations.
View Article and Find Full Text PDFArch Pharm (Weinheim)
January 2023
School of Biosciences, Faculty of Health & Medical Sciences, Taylor's University, Subang Jaya, Selangor, Malaysia.
Oxidative stress and its constant companion, inflammation, play a critical part in the pathogenesis of many acute and chronic illnesses. The discovery of new multi-targeted drug candidates with antioxidant and anti-inflammatory properties is deemed necessary. Thus, a series of novel xanthone derivatives with halogenated benzyl (4b-4d, 4f-4h) and methoxylated benzyl groups (4e) attached to the butoxy amine substituent were synthesized in this study.
View Article and Find Full Text PDFCurr Drug Metab
February 2022
School of Pharmacy, BIN ZHOU Medical University, Yantai 260040,China.
Background: α-mangostin, a typical xanthone, often exists in Garcinia mangostana L. (Clusiaceae). α-mangostin was found to have a wide range of pharmacological properties.
View Article and Find Full Text PDFMolecules
May 2021
Department of Chemistry, Faculty of Natural Sciences and Mathematics, University of Cologne, Greinstr. 4-6, 50939 Köln-Cologne, Germany.
A synthetic route to new heterocyclic 1,1-donor-acceptor-substituted alkenes starting with -methyl-acridone, xanthone, and thioxanthone was investigated, leading to the acridone- and xanthone-derived products methyl 2-methoxy-2-(10-methylacridin-9 (10H)-ylidene)acetate () and methyl 2-methoxy-2-(9H-xanthen-9-ylidene)acetate () in low yields with the de-methoxylated product methyl 2-(10-methylacridin-9 (10H)-ylidene)acetate () and the reduced compound methyl 2-methoxy-2-(9H-xanthen-9-yl)acetate () as the major products from -methyl acridone and xanthone. From thioxanthone, only the rearrangement and reduction products () and () resulted. The photophysical properties of compounds (), (), and () were investigated in the presence and absence of the Brønsted acid TFA by NMR, UV-VIS absorption, and fluorescence spectroscopy.
View Article and Find Full Text PDFBioorg Med Chem Lett
February 2017
College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210046, China; Jiangsu Key Laboratory for TCM Formulae Research, Nanjing 210046, China.
Thirteen xanthones were isolated naturally from the stem of Securidaca inappendiculata Hassk, and structure-activity relationships (SARs) of these compounds were comparatively predicted for their cytotoxic activity against three human multidrug resistant (MDR) cell lines MCF-7/ADR, SMMC-7721/Taxol, and A549/Taxol cells. The results showed that the selected xanthones exhibited different potent cytotoxic activity against the growth of different human tumor cell lines, and most of the xanthones exhibited selective cytotoxicity against SMMC-7721/Taxol cells. Furthermore, some tested xanthones showed stronger cytotoxicity than Cisplatin, which has been used in clinical application extensively.
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