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Special Issue "Coumarins, Xanthones and Related Compounds"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products".

Deadline for manuscript submissions: closed (15 September 2015)

Special Issue Editor

Guest Editor
Prof. Dr. Pascal Richomme

SONAS/SFR QUASAV-UFR Sciences Pharmaceutiques, 16 Bd Daviers, F-49100 Angers, France
Website | E-Mail
Interests: natural products; (hemi)synthesis; biological screening

Special Issue Information

Dear Colleagues,

It has long been known that coumarins (α-pyrones) and xanthones (γ-pyrones) form a large class of naturally occurring compounds exhibiting a wide range of biological activities. However, the interest of the scientific community for these secondary metabolites, as well as for structural analogues, has never decreased since these "old compounds" are constantly generating promising - and sometimes unexpected - therapeutic perspectives. For instance, the xanthone Vadimezan (ASA404 or (5,6-dimethyl-9-oxo-9H-xanthen-4-yl)-acetic acid) was recently developed as a tumor vascular-disrupting agent, whereas many coumarin derivatives are under investigation for their anti-oxidant and anti-inflammatory properties. However, by far, these studies are not restricted to biological activities since coumarins, as an example, may also constitute a molecular model of choice to study hydrogen bonding in the electronic excited state, or even the photovoltaic performances of specific dyes. Therefore, it is probably the right time to launch this third edition, which hopefully will address many fascinating aspects of "coumarins, xanthones and related compounds".

Prof. Dr. Pascal Richomme
Guest Editor

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Keywords

  • coumarins
  • xanthones

Published Papers (15 papers)

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Editorial

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Open AccessEditorial Coumarins, Xanthones and Related Compounds
Molecules 2016, 21(3), 341; doi:10.3390/molecules21030341
Received: 7 March 2016 / Accepted: 8 March 2016 / Published: 10 March 2016
PDF Full-text (154 KB) | HTML Full-text | XML Full-text
Abstract
It has long been known that coumarins (γ-pyrones) and xanthones (α-pyrones) together form a large class of naturally occurring compounds exhibiting a wide range of biological activities.[...] Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)

Research

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Open AccessArticle Synthesis and Characterization of Some New Coumarins with in Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage
Molecules 2016, 21(2), 249; doi:10.3390/molecules21020249
Received: 23 December 2015 / Revised: 2 February 2016 / Accepted: 17 February 2016 / Published: 22 February 2016
Cited by 6 | PDF Full-text (1542 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Coumarins are naturally occurring oxygen heterocyclic compounds having multifarious medicinal properties, hence used as lead compounds for designing new potent analogs. The chromene butenoic acid 3 and the benzochromene butenoic acid 4 which are derived from the reaction of glyoxalic acid with 3-acetylcoumarin
[...] Read more.
Coumarins are naturally occurring oxygen heterocyclic compounds having multifarious medicinal properties, hence used as lead compounds for designing new potent analogs. The chromene butenoic acid 3 and the benzochromene butenoic acid 4 which are derived from the reaction of glyoxalic acid with 3-acetylcoumarin and 3-acetylbenzocoumarin, respectively, were reacted with different nitrogen and carbon nucleophiles to give new heterocyclic compounds. The structures of the prepared compounds were elucidated by IR, 1H-NMR, and mass spectroscopy. Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines namely; hepatocellular carcinoma (liver) HepG2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Coumarin-Containing Polymers for High Density Non-Linear Optical Data Storage
Molecules 2016, 21(2), 147; doi:10.3390/molecules21020147
Received: 8 December 2015 / Revised: 7 January 2016 / Accepted: 18 January 2016 / Published: 26 January 2016
Cited by 5 | PDF Full-text (1806 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Optical data storage was performed with various thin polymer films containing coumarin-based derivatives and by using femtosecond laser pulses as well as two-photon absorption processes. Exploring the photodimerization attribute of coumarin derivatives and using appropriate irradiation wavelengths, recording/erasing processes could be carried out
[...] Read more.
Optical data storage was performed with various thin polymer films containing coumarin-based derivatives and by using femtosecond laser pulses as well as two-photon absorption processes. Exploring the photodimerization attribute of coumarin derivatives and using appropriate irradiation wavelengths, recording/erasing processes could be carried out in the same area. Second harmonic generation microscopy was used to read the stored information. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Nonprenylated Xanthones from Gentiana lutea, Frasera caroliniensis, and Centaurium erythraea as Novel Inhibitors of Vascular Smooth Muscle Cell Proliferation
Molecules 2015, 20(11), 20381-20390; doi:10.3390/molecules201119703
Received: 30 September 2015 / Revised: 23 October 2015 / Accepted: 3 November 2015 / Published: 13 November 2015
Cited by 4 | PDF Full-text (2530 KB) | HTML Full-text | XML Full-text
Abstract
Aberrant proliferation of vascular smooth muscle cells (VSMC) plays a major role in restenosis, the pathological renarrowing of the blood vessel lumen after surgical treatment of stenosis. Since available anti-proliferative pharmaceuticals produce unfavorable side effects, there is high demand for the identification of
[...] Read more.
Aberrant proliferation of vascular smooth muscle cells (VSMC) plays a major role in restenosis, the pathological renarrowing of the blood vessel lumen after surgical treatment of stenosis. Since available anti-proliferative pharmaceuticals produce unfavorable side effects, there is high demand for the identification of novel VSMC proliferation inhibitors. A natural product screening approach using a resazurin conversion assay enabled the identification of gentisin (1) from Gentiana lutea as a novel inhibitor of VSMC proliferation with an IC50 value of 7.84 µM. Aiming to identify further anti-proliferative compounds, 13 additional nonprenylated xanthones, isolated from different plant species, were also tested. While some compounds showed no or moderate activity at 30 µM, 1-hydroxy-2,3,4,5-tetramethoxyxanthone (4), swerchirin (6), and methylswertianin (7) showed IC50 values between 10.2 and 12.5 µM. The anti-proliferative effect of 1, 4, 6, and 7 was confirmed by the quantification of DNA synthesis (BrdU incorporation) in VSMC. Cell death quantification (determined by LDH release in the culture medium) revealed that the compounds are not cytotoxic in the investigated concentration range. In conclusion, nonprenylated xanthones are identified as novel, non-toxic VSMC proliferation inhibitors, which might contribute to the development of new therapeutic applications to combat restenosis. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Auraptene Acts as an Anti-Inflammatory Agent in the Mouse Brain
Molecules 2015, 20(11), 20230-20239; doi:10.3390/molecules201119691
Received: 25 September 2015 / Revised: 24 October 2015 / Accepted: 5 November 2015 / Published: 10 November 2015
Cited by 8 | PDF Full-text (5841 KB) | HTML Full-text | XML Full-text
Abstract
The anti-inflammatory activity of auraptene (AUR), a citrus coumarin, in peripheral tissues is well-known, and we previously demonstrated that AUR exerts anti-inflammatory effects in the ischemic brain; the treatment of mice with AUR for eight days immediately after ischemic surgery suppressed demise and
[...] Read more.
The anti-inflammatory activity of auraptene (AUR), a citrus coumarin, in peripheral tissues is well-known, and we previously demonstrated that AUR exerts anti-inflammatory effects in the ischemic brain; the treatment of mice with AUR for eight days immediately after ischemic surgery suppressed demise and neuronal cell death in the hippocampus, possibly through its anti-inflammatory effects in the brain. We suggested that these effects were at least partly mediated by the suppression of inflammatory mediators derived from astrocytes. The present study showed that (1) AUR, as a pretreatment for five days before and another three days after ischemic surgery, suppressed microglial activation, cyclooxygenase (COX)-2 expression in astrocytes, and COX-2 mRNA expression in the hippocampus; (2) AUR suppressed the lipopolysaccharide-induced expression of COX-2 mRNA and the mRNA of pro-inflammatory cytokines in cultured astrocytes; (3) AUR was still detectable in the brain 60 min after its intraperitoneal administration. These results support our previous suggestion that AUR directly exerts anti-inflammatory effects on the brain. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
Open AccessArticle Synergy and Other Interactions between Polymethoxyflavones from Citrus Byproducts
Molecules 2015, 20(11), 20079-20106; doi:10.3390/molecules201119677
Received: 8 October 2015 / Revised: 28 October 2015 / Accepted: 29 October 2015 / Published: 6 November 2015
Cited by 8 | PDF Full-text (3152 KB) | HTML Full-text | XML Full-text
Abstract
The citrus by-products released from citrus processing plants may contain high levels of potentially bioactive compounds such as flavonoids, which are a widely distributed group of polyphenolic compounds with health-related properties based on their antioxidant activity. In the study reported here, the potential
[...] Read more.
The citrus by-products released from citrus processing plants may contain high levels of potentially bioactive compounds such as flavonoids, which are a widely distributed group of polyphenolic compounds with health-related properties based on their antioxidant activity. In the study reported here, the potential bioactivities and antioxidant activities of extracts, fractions and compounds from citrus by-products were evaluated along with the chemical interactions of binary mixtures of compounds and complex mixtures. The bioactivities and interactions were evaluated in wheat coleoptile bioassays and the antioxidant activity was evaluated by the al DPPH (2,2-diphenyl-1-picrylhdrazyl radical) radical scavenging assay. The extracts, fractions and most of the isolated compounds (mainly polymethoxyflavones) showed high activity in the wheat coleoptile bioassay. However, the antioxidant activity was not consistently high, except in the acetone extract fractions. Moreover, a study of the interactions with binary mixtures of polymethoxyflavones showed the occurrence of synergistic effects. The complex mixtures of fractions composed mainly of polymethoxyflavones caused a synergistic effect when it was added to a bioactive compound such as anethole. The results reported here highlight a new application for the wheat coleoptile bioassay as a quick tool to detect potential synergistic effects in compounds or mixtures. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Analysis of the Photophysical Behavior and Rotational-Relaxation Dynamics of Coumarin 6 in Nonionic Micellar Environments: The Effect of Temperature
Molecules 2015, 20(10), 19343-19360; doi:10.3390/molecules201019343
Received: 10 September 2015 / Revised: 8 October 2015 / Accepted: 16 October 2015 / Published: 23 October 2015
Cited by 4 | PDF Full-text (1234 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The photodynamics of Coumarin 6 have been investigated in three nonionic micellar assemblies, i.e., n-dodecyl-β-d-maltoside (β-C12G2), p-tert-octyl-phenoxy polyethylene (9.5) ether (Triton X-100 or TX100) and n-dodecyl-hexaethylene-glycol (C12E6), to assess their potential
[...] Read more.
The photodynamics of Coumarin 6 have been investigated in three nonionic micellar assemblies, i.e., n-dodecyl-β-d-maltoside (β-C12G2), p-tert-octyl-phenoxy polyethylene (9.5) ether (Triton X-100 or TX100) and n-dodecyl-hexaethylene-glycol (C12E6), to assess their potential use as encapsulation vehicles for hydrophobic drugs. To evaluate the effect of the micellar size and hydration, the study used a broad temperature range (293.15–323.15 K). The data presented here include steady-state absorption and emission spectra of the probe, dynamic light scattering, together with fluorescence lifetimes and both steady-state, as well as time-resolved fluorescence anisotropies. The time-resolved fluorescence anisotropy data were analyzed on the basis of the well-established two-step model. Our data reveal that the molecular probe in all of the cases is solubilized in the hydration layer of micelles, where it would sense a relatively polar environment. However, the probe was found to undergo a slower rotational reorientation when solubilized in the alkylpolyglycoside surfactant, as a result of a more compact microenvironment around the probe. The behavior of the parameters of the reorientation dynamics with temperature was analyzed on the basis of both micellar hydration and the head-group flexibility of the surfactants. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Validated LC-MS/MS Method for the Determination of Scopoletin in Rat Plasma and Its Application to Pharmacokinetic Studies
Molecules 2015, 20(10), 18988-19001; doi:10.3390/molecules201018988
Received: 18 September 2015 / Revised: 12 October 2015 / Accepted: 13 October 2015 / Published: 19 October 2015
Cited by 3 | PDF Full-text (1577 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A rapid, sensitive and selective liquid chromatography-electrospray ionization-tandem mass spectrometric method was developed and validated for the quantification of scopoletin in rat plasma. After the addition of the internal standard xanthotoxin, plasma samples were pretreated by a simple one-step protein precipitation with acetonitrile-methanol
[...] Read more.
A rapid, sensitive and selective liquid chromatography-electrospray ionization-tandem mass spectrometric method was developed and validated for the quantification of scopoletin in rat plasma. After the addition of the internal standard xanthotoxin, plasma samples were pretreated by a simple one-step protein precipitation with acetonitrile-methanol (2:1, v/v). Chromatographic separation was achieved on a Diamonsil ODS chromatography column using gradient elution with the mobile phase consisting of acetonitrile and 0.1% formic acid. The determination was performed by positive ion electrospray ionization in multiple reaction monitoring mode. The calibration curve was linear over the concentration range of 5–1000 ng/mL (r = 0.9996). The intra- and inter-day precision (RSD%) was less than 6.1%, and the accuracy (RE%) was from −3.0%–2.5%. This method was successfully applied to the pharmacokinetic research of scopoletin in rats after intravenous (5 mg/kg) or oral (5, 10 and 20 mg/kg) administration. The result showed that oral bioavailability with a dose of 5 mg/kg was 6.62% ± 1.72%, 10 mg/kg, 5.59% ± 1.16%, and 20 mg/kg, 5.65% ± 0.75%. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Quantification of Coumarins in Aqueous Extract of Pterocaulon balansae (Asteraceae) and Characterization of a New Compound
Molecules 2015, 20(10), 18083-18094; doi:10.3390/molecules201018083
Received: 13 August 2015 / Revised: 16 September 2015 / Accepted: 17 September 2015 / Published: 2 October 2015
Cited by 3 | PDF Full-text (758 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Plants from the genus Pterocaulon are popularly used as antifungal and wound-healing agents. Such activities have been related to coumarins, which are abundant in those plants. Coumarins are soluble in organic solvents, such as hexane and dichloromethane, and some of them are also
[...] Read more.
Plants from the genus Pterocaulon are popularly used as antifungal and wound-healing agents. Such activities have been related to coumarins, which are abundant in those plants. Coumarins are soluble in organic solvents, such as hexane and dichloromethane, and some of them are also soluble in hot water. Considering that infusion and decoctions of these plants are used in traditional medicine, the aim of this study was to identify and quantify the coumarins in the aqueous extract of Pterocaulon balansae. The aqueous extract was obtained by dynamic maceration and the compounds were characterized by UPLC-UV-MS analysis. A new coumarin and 5-methoxy-6,7-methylenedioxycoumarin, used for validation of the analytical HPLC method were obtained by partition of the aqueous extract with n-hexane. The HPLC method validated was linear, specific, and precise. Seven coumarins were characterized in the aqueous extract in a range of 0.584–54 mg/g of dry plant material. The main compound, 5,6-dimethoxy-7-(3′-methyl-2′,3′-dihydroxybutyloxy)coumarin, is described for the first time in P. balansae together with a new compound, 5,6-dimethoxy-7-(2′,3′-epoxy-3′-methylbutyloxy)coumarin. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Phytotoxic Potential and Biological Activity of Three Synthetic Coumarin Derivatives as New Natural-Like Herbicides
Molecules 2015, 20(10), 17883-17902; doi:10.3390/molecules201017883
Received: 16 July 2015 / Revised: 21 September 2015 / Accepted: 21 September 2015 / Published: 29 September 2015
Cited by 5 | PDF Full-text (3377 KB) | HTML Full-text | XML Full-text
Abstract
Coumarin is a natural compound well known for its phytotoxic potential. In the search for new herbicidal compounds to manage weeds, three synthetic derivatives bearing the coumarin scaffold (13), synthesized by a carbonylative organometallic approach, were in vitro assayed
[...] Read more.
Coumarin is a natural compound well known for its phytotoxic potential. In the search for new herbicidal compounds to manage weeds, three synthetic derivatives bearing the coumarin scaffold (13), synthesized by a carbonylative organometallic approach, were in vitro assayed on germination and root growth of two noxious weeds, Amaranthus retroflexus and Echinochloa crus-galli. Moreover, the synthetic coumarins 13 were also in vitro assayed on seedlings growth of the model species Arabidopsis thaliana to identify the possible physiological targets. All molecules strongly affected seed germination and root growth of both weeds. Interestingly, the effects of synthetic coumarins on weed germination were higher than template natural coumarin, pointing out ED50 values ranging from 50–115 µM. Moreover, all synthetic coumarins showed a strong phytotoxic potential on both Arabidopsis shoot and root growth, causing a strong reduction in shoot fresh weight (ED50 values ≤ 60 µM), accompanied by leaf development and a decrease in pigment content. Furthermore, they caused a strong alteration in root growth (ED50 values ≤ 170 µM) and morphology with evident alterations in root tip anatomy. Taken together, our results highlight the promising potential herbicidal activity of these compounds. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
Open AccessCommunication Identification of Minor Benzoylated 4-Phenylcoumarins from a Mammea neurophylla Bark Extract
Molecules 2015, 20(10), 17735-17746; doi:10.3390/molecules201017735
Received: 7 July 2015 / Revised: 25 August 2015 / Accepted: 17 September 2015 / Published: 25 September 2015
Cited by 2 | PDF Full-text (764 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Through dereplication analysis, seven known Mammea coumarins were identified in a fraction obtained from Mammea neurophylla dichloromethane bark extract selected for its ability to prevent advanced glycation end-product (AGE) formation. Among them, a careful examination of the NMR dataset of pedilanthocoumarin B led
[...] Read more.
Through dereplication analysis, seven known Mammea coumarins were identified in a fraction obtained from Mammea neurophylla dichloromethane bark extract selected for its ability to prevent advanced glycation end-product (AGE) formation. Among them, a careful examination of the NMR dataset of pedilanthocoumarin B led to a structural revision. Inspection of LC-DAD-MSn chromatograms allowed us to predict the presence of four new compounds, which were further isolated. Using spectroscopic methods (1H-, 13C- and 2D-NMR, HRMS, UV), these compounds were identified as new benzoyl substituted 4-phenylcoumarins (iso-pedilanthocoumarin B and neurophyllol C) and 4-(1-acetoxypropyl)coumarins cyclo F (ochrocarpins H and I). Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Open AccessArticle Transport of Twelve Coumarins from Angelicae Pubescentis Radix across a MDCK-pHaMDR Cell Monolayer—An in Vitro Model for Blood-Brain Barrier Permeability
Molecules 2015, 20(7), 11719-11732; doi:10.3390/molecules200711719
Received: 16 May 2015 / Revised: 19 June 2015 / Accepted: 23 June 2015 / Published: 25 June 2015
Cited by 7 | PDF Full-text (1081 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Angelicae Pubescentis Radix (APR), a widely used traditional Chinese medicine, is reported to have central nervous system activities. The purpose of this study was to characterize the blood-brain barrier permeability of twelve coumarins from APR including umbelliferone (1), osthol (2
[...] Read more.
Angelicae Pubescentis Radix (APR), a widely used traditional Chinese medicine, is reported to have central nervous system activities. The purpose of this study was to characterize the blood-brain barrier permeability of twelve coumarins from APR including umbelliferone (1), osthol (2), scopoletin (3), peucedanol (4), ulopterol (5), angepubebisin (6), psoralen (7), xanthotoxin (8), bergapten (9), isoimperatorin (10), columbianadin (11), and columbianetin acetate (12) with an in vitro model using a MDCK-pHaMDR cell monolayer. The cell monolayer was validated to be suitable for the permeation experiments. The samples’ transports were analyzed by high performance liquid chromatography and their apparent permeability coefficients (Papp) were calculated. According to the Papp value, most coumarins could be characterized as well-absorbed compounds except for 4, 10 and 11 which were moderately absorbed ones, in concentration-dependent and time-dependent manners. The results of P-glycoprotein (P-gp) inhibitor (verapamil) experiments showed that the transport of coumarin 4 was affected by the transport protein P-gp. Sigmoid functions between permeability log(Papp AP-BL*MW0.5) and log D (at pH 7.4) were established to analyze the structure-activity relationship of coumarins. The results provide useful information for discovering the substance basis for the central nervous system activities of APR, and predicting the permeability of other coumarins through BBB. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
Open AccessArticle Xanthones from the Leaves of Garcinia cowa Induce Cell Cycle Arrest, Apoptosis, and Autophagy in Cancer Cells
Molecules 2015, 20(6), 11387-11399; doi:10.3390/molecules200611387
Received: 4 May 2015 / Revised: 14 June 2015 / Accepted: 15 June 2015 / Published: 19 June 2015
Cited by 5 | PDF Full-text (3086 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two new xanthones, cowaxanthones G (1) and H (2), and 23 known analogues were isolated from an acetone extract of the leaves of Garcinia cowa. The isolated compounds were evaluated for cytotoxicity against three cancer cell lines and
[...] Read more.
Two new xanthones, cowaxanthones G (1) and H (2), and 23 known analogues were isolated from an acetone extract of the leaves of Garcinia cowa. The isolated compounds were evaluated for cytotoxicity against three cancer cell lines and immortalized HL7702 normal liver cells, whereby compounds 1, 5, 8, and 1517 exhibited significant cytotoxicity. Cell cycle analysis using flow cytometry showed that 5 induced cell cycle arrest at the S phase in a dose-dependent manner, 1 and 16 at the G2/M phase, and 17 at the G1 phase, while 16 and 17 induced apoptosis. Moreover, autophagy analysis by GFP-LC3 puncta formation and western blotting suggested that 17 induced autophagy. Taken together, our results suggest that these xanthones possess anticancer activities targeting cell cycle, apoptosis, and autophagy signaling pathways. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
Open AccessArticle Protein Tyrosine Phosphatase 1B Inhibitors from the Roots of Cudrania tricuspidata
Molecules 2015, 20(6), 11173-11183; doi:10.3390/molecules200611173
Received: 20 April 2015 / Revised: 11 June 2015 / Accepted: 12 June 2015 / Published: 17 June 2015
Cited by 8 | PDF Full-text (779 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A chemical investigation of the methanol extract from the roots of Cudrania tricuspidata resulted in the isolation of 16 compounds, including prenylated xanthones 19 and flavonoids 1016. Their structures were identified by NMR spectroscopy and mass spectrometry and
[...] Read more.
A chemical investigation of the methanol extract from the roots of Cudrania tricuspidata resulted in the isolation of 16 compounds, including prenylated xanthones 19 and flavonoids 1016. Their structures were identified by NMR spectroscopy and mass spectrometry and comparisons with published data. Compounds 19 and 1316 significantly inhibited PTP1B activity in a dose dependent manner, with IC50 values ranging from 1.9–13.6 μM. Prenylated xanthones showed stronger PTP1B inhibitory effects than the flavonoids, suggesting that they may be promising targets for the future discovery of novel PTP1B inhibitors. Furthermore, kinetic analyses indicated that compounds 1 and 13 inhibited PTP1B in a noncompetitive manner; therefore, they may be potential lead compounds in the development of anti-obesity and -diabetic agents. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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Review

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Open AccessReview Xanthones of Lichen Source: A 2016 Update
Molecules 2016, 21(3), 294; doi:10.3390/molecules21030294
Received: 25 January 2016 / Revised: 21 February 2016 / Accepted: 23 February 2016 / Published: 2 March 2016
Cited by 6 | PDF Full-text (4628 KB) | HTML Full-text | XML Full-text
Abstract
An update of xanthones encountered in lichens is proposed as more than 20 new xanthones have been described since the publication of the compendium of lichen metabolites by Huneck and Yoshimura in 1996. The last decades witnessed major advances regarding the elucidation of
[...] Read more.
An update of xanthones encountered in lichens is proposed as more than 20 new xanthones have been described since the publication of the compendium of lichen metabolites by Huneck and Yoshimura in 1996. The last decades witnessed major advances regarding the elucidation of biosynthetic schemes leading to these fascinating compounds, accounting for the unique substitution patterns of a very vast majority of lichen xanthones. Besides a comprehensive analysis of the structures of xanthones described in lichens, their bioactivities and the emerging analytical strategies used to pinpoint them within lichens are presented here together with physico-chemical properties (including NMR data) as reported since 1996. Full article
(This article belongs to the Special Issue Coumarins, Xanthones and Related Compounds)
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