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Showing papers on "Xanthone published in 2016"


Journal ArticleDOI
TL;DR: This review has compiled and discussed recent developments on the pharmacological profile of synthetic xanthone derivatives for different therapeutic targets and offers support in the development of new xanthones derivatives as therapeutic agents.

107 citations


Journal ArticleDOI
TL;DR: Chromatographic analysis of EtOAc extract of axenic cultures afforded two new metabolites, namely, the xanthone dimer austradixanthone (1) and the sesquiterpene (+)-austrosene (2), along with five known compounds, which represents the first highly oxygenated heterodimeric xanth one derivative.
Abstract: The endophytic fungus Aspergillus austroafricanus isolated from leaves of the aquatic plant Eichhornia crassipes was fermented axenically on solid rice medium as well as in mixed cultures with Bacillus subtilis or with Streptomyces lividans. Chromatographic analysis of EtOAc extract of axenic cultures afforded two new metabolites, namely, the xanthone dimer austradixanthone (1) and the sesquiterpene (+)-austrosene (2), along with five known compounds (3–7). Austradixanthone (1) represents the first highly oxygenated heterodimeric xanthone derivative. When A. austroafricanus was grown in mixed cultures with B. subtilis or with S. lividans, several diphenyl ethers (8–11) including the new austramide (8) were induced up to 29-fold. The structures of new compounds were unambiguously elucidated using 1D- and 2D-NMR spectroscopy, HRESIMS, and chemical derivatization. Compound 7 exhibited weak cytotoxicity against the murine lymphoma L5178Y cell line (EC50 is 12.6 μM). In addition, compounds 9 and 10, which were...

69 citations


Journal ArticleDOI
TL;DR: This reaction has the potential to become a general synthetic protocol for the preparation of multi-substituted xanthones and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups.
Abstract: Tandem reactions using base-promoted processes have been developed for the synthesis of xanthone and chromone derivatives. The first examples of base-promoted insertion reactions of isolated carbon-carbon triple bonds into carbon-carbon σ-bonds have been reported. Using these approaches, polycyclic structures can be prepared. This reaction has the potential to become a general synthetic protocol for the preparation of multi-substituted xanthones and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups.

42 citations


Journal ArticleDOI
TL;DR: A thorough structure-activity relationship (SAR) analysis of a series of nonpeptidic amphiphilic xanthone derivatives in an attempt to identify more potent compounds with lower hemolytic activity and greater membrane selectivity identified 3a with potent MICs and could be used as a lead compound for further structural optimization for the treatment of MRSA infection.
Abstract: We recently reported the bioinspired synthesis of a highly potent nonpeptidic xanthone, 2c (AM-0016), with potent antibacterial activity against MRSA. Herein, we report a thorough structure–activity relationship (SAR) analysis of a series of nonpeptidic amphiphilic xanthone derivatives in an attempt to identify more potent compounds with lower hemolytic activity and greater membrane selectivity. Forty-six amphiphilic xanthone derivatives were analyzed in this study and structurally classified into four groups based on spacer length, cationic moieties, lipophilic chains, and triarm functionalization. We evaluated and explored the effects of the structures on their membrane-targeting properties. The SAR analysis successfully identified 3a with potent MICs (1.56–3.125 μ/mL) and lower hemolytic activity (80.2 μg/mL for 3a versus 19.7 μg/mL for 2c). Compound 3a displayed a membrane selectivity of 25.7–50.4. Thus, 3a with improved HC50 value and promising selectivity could be used as a lead compound for further...

41 citations


Journal ArticleDOI
TL;DR: Two xanthone derivatives, 12-dimethoxypinselin (1) and 12- O -acetyl-AGI-B4 (2), as well as two phenolic bisabolane-type sesquiterpenes, 11,12-dihydroxysydonic acid (15 ) and 1-hydroxyboivinianic acid (16), together with one new alkaloid, scopulamide (21 ) and one new α-pyrone derivative, scupupyrone (26), in addition

39 citations


Journal ArticleDOI
TL;DR: Results indicate that AcOH acts as a specific signal molecule, able to greatly enhance xanthone biosynthesis in H. perforatum root cultures.
Abstract: Acetic acid acts as a signal molecule, strongly enhancing xanthone biosynthesis in Hypericum perforatum root cultures. This activity is specific, as demonstrated by the comparison with other short-chain monocarboxylic acids. We have recently demonstrated that Hypericum perforatum root cultures constitutively produce xanthones at higher levels than the root of the plant and that they respond to chitosan (CHIT) elicitation with a noteworthy increase in xanthone production. In the present study, CHIT was administered to H. perforatum root cultures using three different elicitation protocols, and the increase in xanthone production was evaluated. The best results (550 % xanthone increase) were obtained by subjecting the roots to a single elicitation with 200 mg l−1 CHIT and maintaining the elicitor in the culture medium for 7 days. To discriminate the effect of CHIT from that of the solvent, control experiments were performed by administering AcOH alone at the same concentration used for CHIT solubilization. Unexpectedly, AcOH caused an increase in xanthone production comparable to that observed in response to CHIT. Feeding experiments with 13C-labeled AcOH demonstrated that this compound was not incorporated into the xanthone skeleton. Other short-chain monocarboxylic acids (i.e., propionic and butyric acid) have little or no effect on the production of xanthones. These results indicate that AcOH acts as a specific signal molecule, able to greatly enhance xanthone biosynthesis in H. perforatum root cultures.

33 citations


Journal ArticleDOI
TL;DR: It is demonstrated that a flavin-dependent monooxygenase (FMO) XanO4 catalyzes the oxidative transformation of an anthraquinone to a xanthone system during the biosynthesis of xantholipin, and the reaction involves sequential insertion of two oxygen atoms, accompanied by an unexpected cryptic demethoxylation reaction.

30 citations


Journal ArticleDOI
TL;DR: The joint isolation of benzophenones and xanthone from the same fungal strain supports the biogenesis of xanthones via a benzophenone intermediate.
Abstract: Two new diphenylketones (1 and 2), a new xanthone (3), and a known xanthone analogue (4) were isolated and identified from Talaromyces islandicus EN-501, an endophytic fungus obtained from the fresh collected marine red alga Laurencia okamurai. Their structures were elucidated on the basis of NMR spectroscopic and X-ray crystallographic analysis. The joint isolation of benzophenones and xanthones from the same fungal strain supports the biogenesis of xanthones via a benzophenone intermediate. It is worth mentioning that xanthones 3 and 4 have a methyl group at C-6 and C-2, respectively, which is uncommon compared with typical xanthones usually having a methyl group at C-8. Compounds 1–4 exhibited potent antioxidative activities against DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonate) radicals with IC50 values ranging from 0.58 to 6.92 μg/mL, which are stronger than that of the positive controls BHT (butylated hydroxytoluene) and ascorbic acid. Compounds 1, 3, and 4 also showed inhibitory activities against several pathogenic bacteria.

29 citations


Journal ArticleDOI
TL;DR: The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselectives base-induced cyclization for the construction of the core xanthone skeleton.
Abstract: Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.

25 citations


Journal ArticleDOI
TL;DR: Gartanin is an isoprenylated xanthone that promotes AR degradation with evidence suggesting this process is critically regulated by the unfolded protein response pathway.
Abstract: cope Androgen receptor (AR) has been a target of prostate cancer for nearly seven decades. In the last several years there has been an interest in identifying compounds that promote degradation of the androgen receptor. In the present study, gartanin, an isoprentylated xanthone in the mangosteen fruit, was evaluated for enhancing AR degradation, and inducing the unfolded protein response pathway. Methods and results The interaction of gartanin with the ligand-binding domain was characterized using a fluorescence polarization cell-free assay and cell-based FRET assay. Western blot analysis identified modulation of ER stress markers (BiP, PERK, IRE1, and CHOP) along with androgen receptor degradation. A computation simulation was performed to identify possible orientations of gartanin with the ligand-binding domain. Utilizing a cell-free and cell-based FRET assays gartanin was found to interact with the ligand-binding domain through a solely antagonist interaction. Interestingly, inhibition of CHOP, a critical component of the ER stress pathway, was observed to stabilize AR. Conclusions Gartanin is an isoprenylated xanthone that promotes AR degradation with evidence suggesting this process is critically regulated by the unfolded protein response pathway.

25 citations


Journal Article
TL;DR: In vitro, confirmed that the mangosteen pericarp extract has the phytochemical bioactive content that possesses anti-obesity potential through pancreatic lipase and α-amylase inhibitory activity.
Abstract: Background: Obesity is a disorder of lipid metabolism and the enzyme involved in this process could be selectively targeted to develop anti obesity drugs. Inhibition of digestive enzymes is one of the most widely studies mechanisms used to determine the hypolipidemic and hypoglycemic agent of natural products for anti-obesity agent screening. Aims: To evaluate the inhibitory potential of G. mangostana extract, xanthone and α-mangosteen compound toward pancreatic lipase and α-amylase enzyme as once of anti-obesity mechanism. Material and Methods: The IC50 value of the mangosteen pericarp extract, xanthone, and α-mangosteen toward pancreatic lipase and α-amylase were determined in vitro compared to orlistat and acarbose as standard drugs. Results: Mangosteen pericarp extract contains phenol, terpenoid, saponin, flavonoid and tannin. Mangosteen pericarp extract is a more active compound in inhibiting the PPL activity compared to α-mangosteen, and xanthone. Mangosteen pericarp extract shows the higher activity compared to xanthone but still lower activity compared to α-mangosteen. However, its activity is still lower than standard drugs. Conclusions: Our in vitro, confirmed that the mangosteen pericarp extract has the phytochemical bioactive content that possesses anti-obesity potential through pancreatic lipase and α-amylase inhibitory activity.

Journal ArticleDOI
TL;DR: The in vitro cytotoxicity of all 11 compounds was evaluated against the KB, HeLa S-3, HT-29, MCF-7 and Hep G2 human cancer cell lines and showed good results.

Journal ArticleDOI
TL;DR: Results indicated that H. perforatum callus cultures represent a promising experimental system for the production of novel xanthone derivatives and other bioactive metabolites of commercial importance.
Abstract: Hypericum perforatum callus cultures exhibited qualitatively and quantitatively different phenolic profile compared to wild-growing plants (WGP). This study revealed the presence of phenolic acids, flavonoid glycosides and aglycones, flavan-3-ols and naphtodianthrones in callus and WGP extracts. Phloroglucinols were detected only in WGP, while xanthones were exclusively found in callus cultures. Among the caffeoyl-, coumaroyl- and feruloyl-quinic acid derivatives identified in both extracts, 3-feruloylquinic acid was identified only in callus cultures. Flavonoid glycosides were represented with quercetin and kaempferol derivatives in both extracts, whereas calli produced a new flavone of luteolin type. Callus cultures showed superior potential for the production of quercetin 6-C-glucoside, hyperoside and kaempferol 3-O-glucoside compared to WGP. Flavonoid aglycones, quercetin and kaempferol were found in both extracts, while I3,II8-biapigenin was accumulated only in WGP. Catechin and procyanidin dimers were abundant in WGP, while epicatechin was dominant flavan-3-ol in callus cultures. With respect to naphtodianthrones, undifferentiated calli were able to produce only pseudohypericin, but in minor amounts compared to WGP. Among the eighteen detected xanthones, mangiferin, mangiferin C-prenyl hexoside and 1,3,6,7-tetrahydroxyxanthone were found as the major compounds in callus cultures. Four xanthones identified as roeperanone, 1,3,7-trihydroxy-2-(2-hydroxy-3-methyl-3-butenyl)-xanthone, trihydroxy-1-methoxy C-prenyl xanthone and 1,5-dihydroxy-2-methoxyxanthone were shown for the first time in H. perforatum callus extracts. Altogether, these results indicated that H. perforatum callus cultures represent a promising experimental system for the production of novel xanthone derivatives and other bioactive metabolites of commercial importance.

Journal ArticleDOI
TL;DR: Preliminary results for screening of xanthone derivatives form a part of an ongoing study of the structure–activity relationships of a large group of compounds.
Abstract: A series of 20 xanthone derivatives was synthesized and evaluated for anti-Helicobacter pylori (H. pylori) activity. Qualitative and quantitative in vitro tests using the Kirby-Bauer method (agar disc-diffusion method) were performed. The tested compounds were screened against clarithromycin- and/or metronidazole-resistant strains of H. pylori. As a reference, Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacterial strains were examined. On the basis of microbiological assays, xanthones can be considered as potential anti-H. pylori agents. They displayed significant activity against the examined strains, which was higher against the bacteria resistant to metronidazole than clarithromycin. The lowest MIC values ranging up to 20 mg l-1 were observed for the following compounds: 3, 4, 8, 9, 12, 19 (against the metronidazole-resistant strains) and the compound 10 (against the clarithromycin-resistant strain). These preliminary results for screening of xanthone derivatives form a part of an ongoing study of the structure-activity relationships of a large group of compounds. Microbiological assays will be conducted afterwards to determine the mechanism of xanthones' action against H. pylori.

Journal ArticleDOI
TL;DR: A new prenylated xanthone, 1,3,6-trihydroxy-2-(3-methylbut-2-enyl)-8-formyloxy-3- methylbutyl)–xanthone has been isolated from the pericarp of Garcinia mangostana, together with five known compounds.
Abstract: Mangostanate, a new prenylated xanthone, 1,3,6-trihydroxy-2-(3-methylbut-2-enyl)-8-(3-formyloxy-3-methylbutyl)–xanthone, has been isolated from the pericarp of Garcinia mangostana, together with fi...

Journal ArticleDOI
TL;DR: Results showed that 1,3,7-trihydroxyxanthone and quercetin showed significant antioxidant activities with EC50 values of 16.20 and 12.68 μg/ml, respectively, as compared to the control, ascorbic acid.

Journal ArticleDOI
TL;DR: In this paper, mesuarianone (3), mesuasinone (4), 1,5-dihydroxyxanthone (5), and four known terpenoids, friedelin (6), stigmasterol (7), beta-sitosterol (8), and gamma-sitostosterol(9).

Journal ArticleDOI
TL;DR: A new xanthone glycoside, sporormielloside, was isolated from an EtOAc extract of an endolichenic fungal strain Sporormiella irregularis and their plausible biosynthetic pathway was deduced.
Abstract: A new xanthone glycoside, sporormielloside (1), was isolated from an EtOAc extract of an endolichenic fungal strain Sporormiella irregularis (No. 71-11-4-1), along with two known xanthones (2, 3). Their structures were determined by detailed spectroscopic analysis (IR, MS, and 1D- and 2D-NMR), a chemical method, and a comparison of NMR data with closely related compounds previously reported. According to the structures of isolated compounds, their plausible biosynthetic pathway was deduced.

Journal ArticleDOI
TL;DR: The results indicate that synthesis of aminoalkanol derivatives of xanthone may lead to successful establishment of new potential anticancer chemicals, and the highest activity to inhibit motility and migration of cancer cells was demonstrated by 7, 12, 15, and by α-mangostin.
Abstract: A series of 15 derivatives of xanthone were synthesized and evaluated for the anticancer activity. The structure of the tested compounds was diversified to establish structureactivity relationships. The following evaluations were carried out: cytotoxicity-proliferation tests, apoptosis detection, expression of apoptosis and proliferation-related genes, expression and activity of gelatinases A and B, wound migration assays, and cell adhesion to MatrigelTMcoated plates. Four compounds (7, 12, 13 and 15) displayed direct cytotoxicity at micromolar concentrations toward the studied cell lines. They also significantly affected the expression of proliferationapoptosis markers, and 13 demonstrated as strong influence as α-mangostin, that served as a natural standard in our study. These four compounds also decreased the expression and activity of gelatinases, and inhibited the migration-motility potential of cancer cells. The influence of compounds 7 and 12 on MMPs mRNA levels even exceeded the activity of α-mangostin and shRNA-mediated silencing; zymography revealed that 7, 13 and 15 were as equally active as α-mangostin, despite their higher IC50 values. The highest activity to inhibit motility and migration of cancer cells was demonstrated by 7, 12, 15, and by α-mangostin; and this was almost equal to shRNA-mediated silencing. Structural features predetermining compound activity were: substitution at position C4 instead of C2, and presence of a chlorine atom and allyl moiety. These results indicate that synthesis of aminoalkanol derivatives of xanthone may lead to successful establishment of new potential anticancer chemicals.

Journal ArticleDOI
TL;DR: Altenusin (12) displayed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus with an MIC value of 32 μg mL−1 and mild activity towards Vero cells with an IC50 value of 19.46 μM.
Abstract: A new xanthone (penicillanthone, 1) and three new diphenyl ether derivatives (penicillidic acids A–C, 2–4) together with 14 known compounds (5–18) were isolated from the soil-derived fungus Penicillium aculeatum PSU-RSPG105. The structures were elucidated by spectroscopic analyses. The absolute configuration of compound 1 was determined using the Snatzke's method whereas those of compounds 2–4 was established by comparison of their optical rotations with those of structurally related compounds. Compound 5 exhibited mild antimycobacterial activity against Mycobacterium tuberculosis with an MIC value of 25 μg mL−1 and was noncytotoxic to noncancerous Vero cells. In addition, altenusin (12) displayed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus with an MIC value of 32 μg mL−1 and mild activity towards Vero cells with an IC50 value of 19.46 μM.

Patent
14 Dec 2016
TL;DR: In this paper, a compound based on xanthone has been proposed, which can be applied to organic light emitting diode as a luminescent layer; and the OLED device using the compound using the Xanthone have good photoelectric property, and can meet the requirements of panel manufacturing enterprises.
Abstract: The invention discloses a compound based on xanthone and application thereof. The compound uses xanthone as a parent nucleus, which is connected to a heteroaromatic group, so as to destroy the molecular symmetry, and thus further destroy the crystallinity of molecules and avoid the aggregation between molecules. The compound based on xanthone has good film-forming property, and can be applied to organic light emitting diode as a luminescent layer; and the OLED device using the compound based on xanthone has good photoelectric property, and can meet the requirements of panel manufacturing enterprises.

Journal ArticleDOI
TL;DR: The new compound 2 containing two hydroxymethyl groups instead of a ketone moiety exhibited significantly improved inhibitory activity against nitric oxide production in lipopolysaccharide-stimulated RAW264.
Abstract: The xanthone glucoside mangiferin (1) was converted by γ-irradiation into three new compounds, mangiferdiol (2), mangiferinol (3), and isomangiferinol (4). The new compound 2 containing two hydroxymethyl groups instead of a ketone moiety exhibited significantly improved inhibitory activity against nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with IC50 value 47.1 ± 1.7 μM, compared to the mother mangiferin.

Journal Article
TL;DR: In this article, a new hydroxy xanthone derivative has anticancer activity using quantitative structure-activity relationship (QSAR) using multilinear regression (MLR).
Abstract: Objective: The objective of the research is to design a new hydroxy xanthone derivative has anticancer activity using quantitative structure-activity relationship (QSAR). Methods: The QSAR designed new compounds were calculated by parameterized model 3 methods and analysis of multi-linear regression (MLR). Result: The result showed that the best model as follows: LogIC = –9.132 qC1 + 28.853 qC5 + 2.456 qC6 – 7.375 qC10 – 5.112 qC11 + 3.900 This result has appropriate some statistical parameters (n=24; PRESS=0.999; r 50 2 =0.782; SEE=0. 235; R=0. 885; F cal /F Conclusion: This Model could be used to design of halogen-substituted hydroxy xanthone scaffold and predict their inhibitory concentration (IC tab =4.68). ) as anticancer in the range of 0.001 - 0.484 μM. Keywords: Anticancer, Quantitative structure-activity relationship, Xanthone. 50

Journal ArticleDOI
08 Apr 2016-Planta
TL;DR: It is demonstrated that YE treatment was followed by a rapid burst of reactive oxygen species (ROS, O2− and H2O2) and subsequent increase in xanthone contents and a possible phenylalanine-independent biosynthesis of xanthones is suggested, which correlates well with the reduced activities of SKDH and SK.
Abstract: Elicitation of xanthones is mediated by ROS where Ca 2+ mediated generation of H 2 O 2 activates the shikimate pathway, a key regulator in early steps of xanthone biosynthesis in H. fastigiata. Shoot cultures of Hoppea fastigiata upon treatment with yeast extract (YE) accumulate an enhanced amount of 1,3,5-trihydroxy-8-methoxy xanthone. We demonstrated that YE treatment was followed by a rapid burst of reactive oxygen species (ROS, O2 − and H2O2) and subsequent increase in xanthone contents. The antioxidant enzymes (NADPH oxidase, superoxide dismutase (SOD), peroxidase and catalase) followed a similar kinetics as that of ROS, depending on their role in production or degradation. It was observed that shikimate dehydrogenase (SKDH) and shikimate kinase (SK) activities enhanced after 8 h, benzophenone synthase activity continued to rise after elicitation and peaked at 18 h. Activities of phenylalanine ammonia-lyase and 4-hydroxycinnamoyl-CoA ligase remained suppressed and unaffected, respectively, after elicitation. This suggests a possible phenylalanine-independent biosynthesis of xanthones. Successive treatment of shoots cultures with a NADPH-oxidase inhibitor diphenylene iodide and a ROS-scavenger dihydrolipoic acid showed inhibition in ROS (O2 − and H2O2) accumulation. These treatments were also shown to decrease the activities of SKDH and SK, leading to a suppressed amount of xanthones formation. Although O2 − showed continuous increase upon treatment with a SOD inhibitor diethyldithiocarbamic acid, the contents of H2O2 and xanthones were decreased, which correlates well with the reduced activities of SKDH and SK. Treatments with calcium antagonists, such as, lanthanum chloride and EGTA were also shown to block the activities of SKDH, SK, NADPH-oxidase and SOD, and consequently leading to suppressed accumulation of ROS (O2 − and H2O2) and xanthones.

DOI
16 Dec 2016
TL;DR: Results indicate that xanthone possesses a potent renoprotective effect in type II diabetes mice, and is used as a traditional medicine in various types of disease.
Abstract: Diabetes mellitus is described as a metabolic disorder with multiple etiology, characterized by chronic hyperglycemia with disturbances of carbohydrate, fat, and protein metabolisms. Recently, obesity has been identified as a risk factor of developing type II diabetes, at about 80 - 85 %. 1 out of 3 people with type II diabetes develop kidney disease. Garcinia mangostana is used as a traditional medicine in various types of disease, such as abdominal pain, dysentery, wound infections, suppuration, and chronic ulcers. Previous studies have revealed that G. mangostana has good antioxidant, antitumoral, antiallergic, anti-inflammatory, antibacterial, and antiviral activities. In this study, an aqueous extract of xanthone derivative from G. mangostana was used, and the total phenolic content and total antioxidant capacity was assessed. Mice body weight, plasma glucose level, kidney hypertrophy (KI, kidney damage indicator), kidney function test (BUN, CREA), plasma, and kidney tissue melondialdehyde level (MDA, as oxidative damage marker) were evaluated in a high fat diet/streptozotocin (HFD/STZ)-induced type II diabetes mouse model. The results showed that the total phenolic compound in xanthone was 272.62±2.26 µg GAE/mg extract and, in the case of the total antioxidant capacity, % of inhibition of xanthone was 88.40±0.25 µmol TEAC/mg extract, respectively. This has significant correlation ( R 2 = 0.9777) to the total phenolic content. In the in vivo study, increased body weight, plasma glucose level, kidney hypertrophy, plasma kidney profile, plasma, and kidney tissue melondialdehyde levels were significantly increased ( P < 0.05) in the HFD/STZ-induced type II diabetes mouse model. Co-treatment with xanthone significantly ( P < 0.05) improved all of the biochemical parameters and body weight in the mouse model. Taken together, the results indicate that xanthone possesses a potent renoprotective effect in type II diabetes mice.

Journal ArticleDOI
TL;DR: A new alkylated coumarin derivative, hexapetarin along with three other xanthones, trapezifolixanthone (2), cudraxanthone G (3) and 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanth one (4) were isolated from the stem bark of Mesua Hexapetala (Clusiaceae).

Journal ArticleDOI
22 Aug 2016-Molbank
TL;DR: The structure of 1 was established by spectroscopic analysis which included UV, IR, HRESIMS and NMR experiments as mentioned in this paper, and the structure of 2 was established using spectrograms from the stem bark of Calophyllum pseudomole.
Abstract: 5,9,11-Trihydroxy-2,2-dimethyl-10-(3′-methyl-2′-butenyl)-3-(2″-methyl-3″-butenyl)-pyrano[2,3-a]xanthen-12(2H)-one (1) was isolated from the stem bark of Calophyllum pseudomole. The structure of 1 was established by spectroscopic analysis which included UV, IR, HRESIMS and NMR experiments.

01 Jan 2016
TL;DR: In this paper, a new isoprenylated xanthone, 5,9,11-trihydroxy-2,2-dimethyl-10-(3 0 -methyl-2 0 -butenyl)-3-(2”-methyl-3”)-pyrano[2,3-a]xanthen-12(2H)-one was isolated from the stem bark of Calophyllum pseudomole.
Abstract: 5,9,11-Trihydroxy-2,2-dimethyl-10-(3 0 -methyl-2 0 -butenyl)-3-(2”-methyl-3”-butenyl)-pyrano[2,3-a]xanthen-12(2H)-one ( 1 ) was isolated from the stem bark of Calophyllum pseudomole.The structure of 1 was established by spectroscopic analysis which included UV, IR, HRESIMS andNMR experiments. Keywords: 5,9,11-trihydroxy-2,2-dimethyl-10-(3 0 -methyl-2 0 -butenyl)-3-(2”-methyl-3”butenyl)-pyrano[2,3-a]xanthen-12(2H)-one; xanthone; Calophyllum pseudomole 1. Introduction The Calophyllum genus (Clusiaceae) comprises more than 180 species found mainly in SoutheastAsia. This genus has been shown to produce a number of secondary metabolites, particularlyxanthones [1–3], coumarins [4–6], chromanone acids [7–9], and flavonoids [10]. In Indonesia, the localname of Calophyllum is ‘bitangor’ [11].Herein, we report the isolation and structural elucidation of a new isoprenylated xanthone,5,9,11-trihydroxy-2,2-dimethyl-10-(3 0 -methyl-2 0 -butenyl)-3-(2”-methyl-3”-butenyl)-pyrano[2,3-a]xanthen-12(2H)-one (

Journal Article
TL;DR: Total antioxidant capacity (expressed as a ferric reducing antioxidant power - FRAP) and ability to scavenge free radicals (DPPH methods) by xanthone derivatives showing antiepileptic activity are evaluated.
Abstract: Certain xanthone derivatives, such as these present in mangosteen fruits, show strong antioxidant activity. On the other hand, evidences accumulated that oxidative stress is involved in epileptogenesis. Therefore, the aim of the present study was to estimate total antioxidant capacity (expressed as a ferric reducing antioxidant power - FRAP) and evaluate ability to scavenge free radicals (DPPH methods) by xanthone derivatives showing antiepileptic activity. Selected 2-(aminomethyl)-9H-xanthen-9-one derivatives shared structural features, such as chlorine substituent in xanthone ring and different chiral (or not) alkanol groups at the nitrogen atom. The results of antioxidant activities among racemates revealed the highest activity for compound (RIS)-3 (31.7% in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and (0.184 ± 0.003 mM Fe²⁺/L) in FRAP assay. Among tested pair of enantiomers we observed that (R)-1 and (R)-2 showed higher reduction capacity ((R)-1: 0.096 ± 0.007 mM F²⁺/L; (R)-2: 0.048 ± 0.005 mM Fe²⁺/L, respectively) and stronger DPPH scavenging activity ((R)-1: 31 ± 3.0%; (R)-2: 29 ± 2.5%, respectively) comparing to their (S)-enantiomers and racemates.

Journal Article
TL;DR: This review article can be reasonably encouraging for those engaged in the area of developing efficient and effective, single therapeutic agent exhibiting a wide range of biological activities involving xanthone as crucial and central nucleus.
Abstract: Xanthone is a novel and pharmacologically important oxygen containing hetrocyclic ring exhibiting variety of potent biological activities. This fused tricyclic ring is derived naturally from the plants of Bonnetiaceae and Clusiaceae family as well as synthesized by employing various synthetic protocols. Their wide range of reported therapeutic attributes include α-glucosidase inhibition, anti-cancer, anti-oxidant, anti-asthmatic, anti-convulsant, xanthine oxidase inhibition and anti-microbial. Among these attributes, anti-cancer and anti-oxidant potential are comprehensively studied as evidenced by number of research papers. Although, there is no marketed formulation containing xanthone derivatives except some herbal formulations, their medicinal properties can not be neglected at all. Promising activities revealed by these compounds chains their use and places them ahead as potential drug candidates for the future studies. Therefore, the present review article is entirely an assemblage of recent research work that has been done on xanthones and their analogs as therapeutic agents. This review article can be reasonably encouraging for those engaged in the area of developing efficient and effective, single therapeutic agent exhibiting a wide range of biological activities involving xanthone as crucial and central nucleus.