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Showing papers on "Xanthone published in 2009"


Journal ArticleDOI
TL;DR: Xanthone production in Hypericum perforatum suspension cultures in response to elicitation by Agrobacterium tumefaciens co-cultivation has been studied and revealed that xanthones play dual function in plant cells during biotic stress: as antioxidants to protect the cells from oxidative damage and as phytoalexins to impair the pathogen growth.

112 citations


Journal ArticleDOI
TL;DR: In this paper, a review of natural and synthetic xanthone compounds which have potential as anticancer drugs is presented, where the authors discuss the properties of xanthones, including antihypertensive, antioxidative and anticancer activity.
Abstract: Objectives Xanthones are simple three-membered ring compounds that are mainly found as secondary metabolites in higher plants and microorganisms. Xanthones have very diverse biological profiles, including antihypertensive, antioxidative, antithrombotic and anticancer activity, depending on their diverse structures, which are modified by substituents on the ring system. Although several reviews have already been published on xanthone compounds, few of them have focused on the anticancer activity of xanthone derivatives. In this review we briefly summarize natural and synthetic xanthone compounds which have potential as anticancer drugs. Key findings The interesting structural scaffold and pharmacological importance of xanthone derivatives have led many scientists to isolate or synthesize these compounds as novel drug candidates. In the past, extensive research has been conducted to obtain xanthone derivatives from natural resources as well as through synthetic chemistry. Xanthones interact with various pharmacological targets based on the different substituents on the core ring. The anticancer activities of xanthones are also dramatically altered by the ring substituents and their positions. Summary The biological activities of synthetic xanthone derivatives depend on the various substituents and their position. Study of the biological mechanism of action of xanthone analogues, however, has not been conducted extensively compared to the diversity of xanthone compounds. Elucidation of the exact biological target of xanthone compounds will provide better opportunities for these compounds to be developed as potent anticancer drugs. At the same time, modification of natural xanthone derivatives aimed at specific targets is capable of expanding the biological spectrum of xanthone compounds.

109 citations


Journal ArticleDOI
TL;DR: Bioassay-guided fractionation of a chloroform-soluble extract of Garcinia mangostana stem bark, using the HT-29 human colon cancer cell line and an enzyme-based ELISA NF-kappaB assay, led to the isolation of a new xanthone, 11-hydroxy-3-O-methyl-1-isomangostin (1).
Abstract: Bioassay-guided fractionation of a chloroform-soluble extract of Garcinia mangostana stem bark, using the HT-29 human colon cancer cell line and an enzyme-based ELISA NF-kappaB assay, led to the isolation of a new xanthone, 11-hydroxy-3-O-methyl-1-isomangostin (1) The structure of 1 was elucidated by spectroscopic data analysis In addition, 10 other known compounds, 11-hydroxy-1-isomangostin (2), 11alpha-mangostanin (3), 3-isomangostin (4), alpha-mangostin (5), beta-mangostin (6), garcinone D (7), 9-hydroxycalabaxanthone (8), 8-deoxygartanin (9), gartanin (10), and cratoxyxanthone (11), were isolated Compounds 4-8 exhibited cytotoxicity against the HT-29 cell line with ED50 values of 49, 17, 17, 23, and 91 microM, respectively In an ELISA NF-kappaB assay, compounds 5-7, 9, and 10 inhibited p65 activation with IC50 values of 159, 121, 32, 113, and 190 microM, respectively, and 6 showed p50 inhibitory activity with an IC50 value of 75 microM Alpha-mangostin (5) was further tested in an in vivo hollow fiber assay, using HT-29, LNCaP, and MCF-7 cells, but it was found to be inactive at the highest dose tested (20 mg/kg)

84 citations


Journal ArticleDOI
TL;DR: Three new metabolites, microsphaeropsones A-C (1-3) with a unique oxepino[2,3-b]chromen-6-one (ring-enlarged xanthone) skeleton, were isolated from the endophytic fungus Microsphaaropsis species, co-occurring with their putative biogenetic anthraquinoide precursors citreorosein and emodin.
Abstract: Three new metabolites, microsphaeropsones A-C (1-3) with a unique oxepino[2,3-b]chromen-6-one (ring-enlarged xanthone) skeleton, were isolated from the endophytic fungus Microsphaeropsis species, co-occurring with their putative biogenetic anthraquinoide precursors citreorosein (4) and emodin (5). From another Microsphaeropsis species, large amounts of fusidienol A (8 a), smaller amounts of emodin (5), the known aromatic xanthones 9 a and 9 b, the new 3,4-dihydrofusidienol A (8 b), and the new aromatic xanthone 9 c were isolated. The endophyte Seimatosporium species produced a new aromatic xanthone, seimatoxanthone A (10), and 3,4-dihydroglobosuxanthone A (12), closely related to alpha-diversolonic ester (13) from Microdiplodia sp.. The structures were determined mainly by extensive 1D and 2D NMR experiments and supported by X-ray single-crystal analysis of 1 and the oxidation product 7. The absolute configurations of the microsphaeropsones A-C (1-3) were established by comparison of the electronic and vibrational circular dichroism (ECD and VCD) spectra of 1 with time-dependent DFT (TDDFT) and DFT calculations by using either the solid-state structures or DFT-optimized geometries as inputs. Preliminary studies indicated that 1, 2, and enone 7 showed antibacterial, fungicidal, and algicidal properties.

81 citations


Journal ArticleDOI
TL;DR: The furanoxanthone psorospermin is a highly promising isolated xanthone derivative exhibiting significant cytotoxicity through a novel mechanism of action, being an irreversible topoisomerase II poison and it was selected for further development as an antineoplastic agent.
Abstract: Xanthones have been isolated from several natural sources, mainly belonging in Guttiferae and Gentianaceae families as secondary plant metabolites and many of them are endowed with diverse pharmacological properties. We have focused in the study of cytotoxic fused xanthone derivatives, having in mind that some furano- and pyranoxanthone natural products are particularly interesting, in terms of cytotoxic potency and novelty in their mechanism of action and could serve as lead compounds for the development of clinically effective anticancer agents. In this review, a general classification has been attempted based on the type of ring fusion, in such a way that natural compounds as well as synthetic derivatives are discussed. The furanoxanthone psorospermin is a highly promising isolated xanthone derivative exhibiting significant cytotoxicity through a novel mechanism of action, being an irreversible topoisomerase II poison and it was selected for further development as an antineoplastic agent. An important number of pyranoxanthones have been synthesized using as lead compound the acridone alkaloid acronycine. Adducts on the double bond of these compounds provided cytotoxic derivatives possessing cell-cycle selectivity. The synthesis of pyranoxanthones bearing aminosubstituted side-chains resulted in compounds that exhibit markedly improved cytotoxicity towards leukemic and solid tumor cell lines. Azabioisosters of the aminoderivatives exhibit solid tumor selectivity whereas additional pyrazole or/and benzene ring fusion has been incorporated into the xanthone skeleton and resulted in compounds with promising activity, which retain full antiproliferative activity against P-glycoprotein-overexpressing cells. Gambogic acid, a highly effective anticancer drug candidate with low toxicity to normal tissue, together with structurally related representative analogues are also mentioned.

59 citations


Journal ArticleDOI
TL;DR: The xanthone and garcihombronane D displayed a selective activity against Plasmodium falciparum; isoxanthochymol and the triterpene beta-hydroxy-5-glutinen-28-oic acid a broad but non-selective antiprotozoal activity.

59 citations


Journal ArticleDOI
TL;DR: In this article, the xanthones from mangosteen ( Garcinia mangostana ) pericarp were extracted with and without alcohol as entrainer at 30MPa and 50°C in supercritical carbon dioxide (SC-CO 2 ).
Abstract: The xanthones from mangosteen ( Garcinia mangostana ) pericarp was extracted with and without alcohol as entrainer at 30 MPa and 50 °C in supercritical carbon dioxide (SC-CO 2 ). It was found that entrainer increases the rate of extraction and yield substantially. SC-CO 2 + ethanol (4%) at 20 MPa, 40 °C was investigated by HPLC/LC–ESI-MS for characterization of the xanthones. From liquid chromatography electron spray ionization mass spectrometry (LC–ESI-MS) spectra, 12 components were structurally correlated and confirmed based on the fragmentation characteristics and information available in the literature. The occurrence of these xanthone in SC-CO 2 extract is reported for first time in G. mangostana species. The antioxidant activities of SC-CO 2 were investigated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC 50 = 41.8 μg/mL), lipid peroxidation (IC 50 = 21.5 μg/mL), hydroxyl radicals site specific (IC 50 = 30.0 μg/mL) and hydroxyl radicals non-site specific (IC 50 = 23.1 μg/mL). From cytochrome c assay it was observed that SC-CO 2 extract can reduce ferric cytochrome c to ferrocytochrome c . The results showed that SC-CO 2 had great potential as antioxidant agent.

59 citations


Journal ArticleDOI
TL;DR: In this article, the antiperoxidative properties of α-mangostin, a xanthone isolated from mangosteen fruit, were tested for the first time in nerve tissue exposed to different toxic insults.
Abstract: The antiperoxidative properties of α-mangostin, a xanthone isolated from mangosteen fruit, were tested for the first time in nerve tissue exposed to different toxic insults. Two reliable biological preparations (rat brain homogenates and synaptosomal P2 fractions) were exposed to the toxic actions of a free radical generator (ferrous sulfate), an excitotoxic agent (quinolinate), and a mitochondrial toxin (3-nitropropionate). α-Mangostin decreased the lipoperoxidative action of FeSO4 in both preparations in a concentration-dependent manner, and completely abolished the peroxidative effects of quinolinate, 3-nitropropionate and FeSO4 + quinolinate at all concentrations tested. Interestingly, when tested alone in brain homogenates, α-mangostin significantly decreased the lipoperoxidation even below basal levels. α-Mangostin also prevented the decreased reductant capacity of mitochondria in synaptosomal fractions. Our results suggest that α-mangostin exerts a robust antiperoxidative effect in brain ti...

52 citations


Journal ArticleDOI
TL;DR: Results suggested that P1 and P3 could be used as a potential anticancer agent and strong antioxidant activities were detected for P1–P3.

48 citations


Journal Article
TL;DR: Different parts of the plant showed the presence of large number of phenyl propanoids, sesquiterpenes and monoterpenes as well as xanthone glycosides, flavones, lignans, steroids and inorganic constituents.
Abstract: Chemical constituents and biological activity of plant drug Acorus calamus Linn. (family:Araceae) was reviewed. Different parts of the plant showed the presence of large number of phenyl propanoids, sesquiterpenes and monoterpenes as well as xanthone glycosides, flavones, lignans, steroids and inorganic constituents. It is also reported to possess insecticidal, larvicidal, antibacterial, mutagenic, cytotoxic, hepatoprotective, anticonvulsant,neuroleptic,smooth muscle relaxant and smooth muscle stimulant activity.

45 citations


Journal ArticleDOI
TL;DR: A new tetraoxygenated xanthone, cowaxanthone F (1), as well as four known compounds, morelloflavone (2), volkensiflavone(3), morelloftlavone-7″-O-glucoside (fukugiside, 4), and 1,6-dihydroxyxanthon...
Abstract: A new tetraoxygenated xanthone, cowaxanthone F (1), as well as four known compounds, morelloflavone (2), volkensiflavone (3), morelloflavone-7″-O-glucoside (fukugiside, 4), and 1,6-dihydroxyxanthon...

Journal ArticleDOI
TL;DR: A xanthonolignoid, 2-O-demethylkielcorin, and a phenylxanthone, chinexanth one A, were isolated from stems of Hypericum chinense and their structures were established by spectroscopic analysis, as their optical properties and absolute stereochemistry determined.

Journal ArticleDOI
TL;DR: In vivo plasma concentrations of α-mangostin, the most abundant xanthone derivative found in mangosteen, were predicted using Simcyp and found to be well above their respective in vitro Ki values for CYP 2C8 and CYP2C9.
Abstract: Mangosteen is a xanthone-containing fruit found in Southeast Asia for which health claims include maintaining healthy immune and gastrointestinal systems to slowing the progression of tumor growth and neurodegenerative diseases. Previous studies have identified multiple xanthones in the pericarp of the mangosteen fruit. The aim of the current study was to assess the drug inhibition potential of mangosteen in vitro as well as the cytochrome P450 (P450) enzymes responsible for the metabolism of its individual components. The various xanthone derivatives were found to be both substrates and inhibitors for multiple P450 isoforms. Aqueous extracts of the mangosteen pericarp were analyzed for xanthone content as well as inhibition potency. Finally, in vivo plasma concentrations of α-mangostin, the most abundant xanthone derivative found in mangosteen, were predicted using Simcyp and found to be well above their respective in vitro K i values for CYP2C8 and CYP2C9.

01 Jan 2009
TL;DR: In this article, the xanthones in the acetone, ethyl acetate and hexane extract, were investigated by means of high performance liquid chromatography-electrospray ionisation/mass spectrometry (HPLC-ESI/MS) technique.
Abstract: The aim of this study was to separate and determine the xanthones from mangosteen (Garcinia mangostana) pericarp. The xanthones in the acetone, ethyl acetate and hexane extract, was investigated by means of high performance liquid chromatography–electrospray ionisation/mass spectrometry (HPLC–ESI/MS) technique. Chromatography of the xanthones on a RP-C-18 HPLC column followed by MS detection using ESI negative mode showed the presence of seven major known xathones: 3-isomangostin, 8-desoxygartanin, gartanin, α-mangostin, garcinone E (tentatively identified), 9-hydroxycalabaxanthone and β- mangostin. The antioxidative properties of mangosteen pericarp extracts which is the mixture of these xanthones obtained by different solvents were investigated for reactive oxygen species scavenging, like cytochrome c assay, molybdenum activity and lipid peroxidation inhibition assay. Of the solvent extracts acetone and ethyl acetate extracts reduced oxidized cytochrome c to an OD of 0.455 and 0.321 at 400 µg; each of the extract reduced Mo (1V) to Mo (V) at 100 µg to 7967 ± 47.1 and 6803 ± 42.1 µmole/g of ascorbic acid equivalent. The IC 50 value for lipid peroxidation was 9.2 ±3.8 and 10.0 ± 1.7 µg/ml which was higher than standard BHA respectively. Hexane extract showed less antioxidant activity in the above test because of the poor solubility of the xanthones. The results indicate that xanthones show good antioxidant property and a method was validated to identify them by HPLC-MS method.

Journal ArticleDOI
TL;DR: In this paper, 14 prenylated xanthones found in mangosteen fruit, Garcinia mangostana L, have been simultaneously separated by reversed-phase high-performance liquid chromatography with water-acetonitrile gradient elution and diode-array detection.
Abstract: Fourteen prenylated xanthones found in mangosteen fruit, Garcinia mangostana L., have been simultaneously separated by reversed-phase high-performance liquid chromatography with water–acetonitrile gradient elution and diode-array detection. The separated xanthones were detected at 254 nm. This new method was developed to establish a chemical fingerprint of the major constituents of mangosteen. It was also used for quantitative analysis of the two major xanthones in crude extracts of mangosteen fruit hull. This chemical fingerprint of G. mangostana extract can be used for comprehensive quality-control of mangosteen extract.

Journal ArticleDOI
TL;DR: The structural elucidation of the two new compounds 6,11, as well as an update of data for the already described prenylated derivatives 7,8,10 were accomplished by IR, UV, HRMS and NMR techniques.
Abstract: Pyranoxanthones 6-8 were obtained by dehydrogenation of the respective dihydropyranoxanthones 3-5 with DDQ in dry dioxane. Two prenylated xanthones 10,11 were obtained from the reaction of 1-hydroxyxanthone (9) with prenyl bromide in alkaline medium, or by condensation of xanthone 9 with isoprene in the presence of orthophosphoric acid. The structural elucidation of the two new compounds 6,11, as well as an update of data for the already described prenylated derivatives 7,8,10 were accomplished by IR, UV, HRMS and NMR (1H, 13C, HSQC and HMBC) techniques. The effect of the prenylated xanthone derivatives on the in vitro growth of human tumor cell lines MCF-7 (breast adenocarcinoma) and NCI-H460 (non-small cell lung cancer) is also reported. Compounds 10 and 11 have been found to exhibit a moderate growth inhibitory activity against the MCF-7 cell line.

Journal ArticleDOI
Lan Ding1, Bo Liu1, Lin-lin Qi1, Qi-yin Zhou1, Qian Hou1, Juan Li1, Qiong Zhang1 
TL;DR: The results showed that xanthone 1 had a significant cytotoxic effect and could induce proliferation inhibition and apoptosis in HL-60 cells in a time- and dose-dependent manner.

Journal ArticleDOI
TL;DR: In this article, 11 prenylated xanthone derivatives were synthesized for the first time by the microwave irradiation method using Montmorillonite K10 clay as a heterogeneous catalyst.

Journal ArticleDOI
TL;DR: A series of 2‐substituted xanthone derivatives 8–20 containing selected allyl, cinnamyl, morpholine, and imidazole moieties were synthesized and tested for their antifungal and antibacterial in‐vitro properties, showing significant efficacy against evaluated yeasts and dermatophytes.
Abstract: A series of 2-substituted xanthone derivatives 8-20 containing selected allyl, cinnamyl, morpholine, and imidazole moieties were synthesized and tested for their antifungal and antibacterial in-vitro properties. Of the newly synthesized derivatives, ten revealed antifungal activity especially against Trichophyton mentagrophytes (the biggest inhibition zones ranged 35 mm for 11 and 13). 2-(3-(Allylamino)propoxy)-9H-xanthen-9-one hydrochloride 9 inhibited growth of all of the examined fungal species. Significant efficacy against evaluated yeasts and dermatophytes was also observed for 6-chloro-2-methyl-9H-xanthen-9-one derivatives 11-13 containing encyclic amine moieties. Additionally, compounds 9, 11, and 12 hindered development of bacteria species but in a lesser degree. They were efficacious against Staphylococcus aureus, Escherichia coli, and Enterococcus faecalis.

Journal ArticleDOI
TL;DR: In this article, a nonmetal catalytic system consisting of N-hydroxyphthalimide, xanthone, and tetramethylammonium chloride was developed, and a wide range of hydrocarbons could be oxidized efficiently with dioxygen under mild conditions.

Journal ArticleDOI
TL;DR: In this article, a sustainable xanthone core extraction process is proposed based on the use of water as an environmentally friendly solvent, which is based on nucleophilic aromatic substitution reactions.

Journal ArticleDOI
TL;DR: Parnafungins, natural products containing an isoxazolidinone ring, have been isolated from Fusarium larvarum and have been shown to be potent inhibitors of the fungal polyadenosine polymerase.

Journal ArticleDOI
TL;DR: The structures of these compounds were established on the basis of one- and two-dimensional NMR homo- and heteronuclear correlation evidence and were evaluated for their apoptotic and antiproliferative activities against human leukemic B lymphocytes, such as the hairy cell leukemia-derived ESKOL cell line and cells from B-CLL (B-cell chronic lymphocytic leukemia) patients.
Abstract: Phytochemical investigations of the seeds of ALLANBLACKIA MONTICOLA have led to the isolation and characterization of one new xanthone derivative, named allanxanthone E ( 1), together with seven known compounds, including five xanthones, 1,7-dihydroxy-3-methoxy-2-(3-methylbut-2-enyl)xanthone ( 2), alpha-mangostin ( 3) , garciniafuran ( 4) , allanxanthone C ( 5), and 1,6-dihydroxy-2,4-diprenylxanthone ( 6), and two pentacyclic triterpenes, friedelin and lupeol. The structures of these compounds were established on the basis of one- and two-dimensional NMR homo- and heteronuclear correlation evidence. Some of these compounds were evaluated for their apoptotic and antiproliferative activities against human leukemic B lymphocytes, such as the hairy cell leukemia-derived ESKOL cell line and cells from B-CLL (B-cell chronic lymphocytic leukemia) patients.

Journal ArticleDOI
TL;DR: In this paper, five new xanthones, garcinenone A (1), B (3), C (4), D (7) and E (8), along with seven known compounds were isolated from the EtOAc-soluble extract of the bark of Garcinia xanthochymus, and their structures were elucidated by spectroscopic methods, especially 2D-NMR techniques.
Abstract: Five new xanthones, garcinenone A (1), B (3), C (4), D (7) and E (8), along with 7 known compounds were isolated from the EtOAc-soluble extract of the bark of Garcinia xanthochymus, and their structures were elucidated by spectroscopic methods, especially 2D-NMR techniques. Jacareubin (2), 1,4,6-trihydroxy-5-methoxy-7-(3-methyl-2-butenyl)xanthone (6), subeliptenone B (11) and symphoxanthone (12) were obtained from this plant for the first time. The isolated compounds exhibited potent antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging test with IC50 values in the 6.0–23.2 µmol/L. These results suggested that G. xanthochymus could be a promising rich source of natural antioxidant.

Journal ArticleDOI
TL;DR: The spectral data of ugaxanthone and mbarraxanthone are reported here for the first time, as well as the antimicrobial activity of globulixanthone F against a range of microorganisms.
Abstract: Bioassay-guided fractionation of the stem bark of Symphonia globulifera has yielded three known xanthones, ugaxanthone (1), mbarraxanthone (2) and gentisein (3), two biflavonoid derivatives named GB2 (4) and manniflavanone GB3 (5), and one new polyoxygenated xanthone with an isoprenoid group, named globulixanthone F (6). The structures of these compounds were elucidated by means of spectroscopic methods. The spectral data of 1 and 2 are reported here for the first time, as well as the antimicrobial activity of globulixanthone F against a range of microorganisms. We also report the total synthesis of the xanthone skeleton.

Journal ArticleDOI
TL;DR: In this article, Xanthone, as its dimethyl ketal, undergoes functionalization with a synthetically useful degree of regioselectivity using a lithiation protocol.

Journal ArticleDOI
TL;DR: Two bioactive xanthones from Hypericum perforatum have been synthesized by direct routes and Benzo[c]xanthone 5 can be prepared from intermediate 4.
Abstract: Two bioactive xanthones from Hypericum perforatum have been synthesized by direct routes. Benzo[c]xanthone 5 can be prepared from intermediate 4.

Journal ArticleDOI
TL;DR: Results indicate that Cu (II) complex can intercalate into the DNA base pairs by the plane of xanthone ring and the studies of DNA-binding agree with the effects on the inhibition of tumor cells in vitro.
Abstract: 1, 8-(3, 6, 9-Trioxaundecane-1, 11-diyldioxy)xanthone (L), and its new Cu (II) complex [Cu·L·(CH3CN)2](ClO4)2 have been synthesized and characterized by 1H NMR, electrospray mass spectra (ESI-MS), elemental analyses, infrared spectra (IR) and X-ray single crystal diffraction. The crystal structure of complex shows that Cu (II) ion is encapsulated within the macrocycle of L. The geometry around copper is a distorted square bipyramid with two acetonitrile molecules at axial position, and four macrocyclic oxygens including the carbonyl oxygen on the equatorial positions. The interaction of Cu (II) complex with calf thymus DNA (ct DNA) has been investigated by spectrophotometric titrations, ethidium bromide (EB) displacement experiments, circular dichroism (CD) spectra and viscosity measurements. Rresults indicate that Cu (II) complex can intercalate into the DNA base pairs by the plane of xanthone ring. Furthermore, the Cu (II) complex was tested against tumor cell lines including ECA109, SGC7901and GLC-82 by MTT (microculture tetrazolium) method. The studies of DNA-binding agree with the effects on the inhibition of tumor cells in vitro.

Journal ArticleDOI
TL;DR: Two new xanthones have been isolated from the stems of Cratoxylum cochinchinense (Lour.) Blume and their structures were established on the basis of spectroscopic analysis.

Journal ArticleDOI
TL;DR: A number of O-alkylated xanthone, carbazoles and coumarins have been synthesised and screened for their in vitro anti-diabetic activity, such as glucose-6-phosphatase, glycogen phosphorylase and alpha glucosidase inhibitors, which showed significant percentage inhibition in sucrose loaded normal and streptozotocin (STZ)-induced diabetic rats.