Xanthone

antitumor, antihepatotoxic, anti-inflammatory and antimicrobial activities CAS# 90-47-1

Xanthone

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Chemical structure

Xanthone

3D structure

Chemical Properties of Xanthone

Cas No. 90-47-1 SDF Download SDF
PubChem ID 7020 Appearance Powder
Formula C13H8O2 M.Wt 196.2
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble to 39 mg/mL warmed (198.77 mM) in DMSO
Chemical Name xanthen-9-one
SMILES C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3O2
Standard InChIKey JNELGWHKGNBSMD-UHFFFAOYSA-N
Standard InChI InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Xanthone

The twigs of Calophyllum inophyllum

Biological Activity of Xanthone

DescriptionXanthone has antioxidant and anticorrosive properties, it performed excellently as a corrosion inhibitor for mild steel in sulphuric acid solution.
In vitro

Anti-corrosive properties of xanthone on mild steel corrosion in sulphuric acid: Experimental and theoretical investigations[Reference: WebLink]

Current Applied Physics, 2011, 11(3):382-392.


METHODS AND RESULTS:
The anti-corrosive effect of Xanthone (XAN) on the corrosion of mild steel in 0.5 M H2SO4 has been studied by gravimetric and UV–visible spectrophotometric methods at 303–333 K. Results obtained revealed that XAN performed excellently as a corrosion inhibitor for mild steel in sulphuric acid solution. Inhibition efficiency increases with increase in concentration of XAN but decreases with rise in temperature which is suggestive of physical adsorption mechanism although chemisorption may also play a part. Dubinin–Radushkevich adsorption isotherm model was found to adequately describe the adsorption of XAN onto the mild steel surface. Kinetic parameters of activation and thermodynamic parameters using the statistical model were calculated and discussed.
CONCLUSIONS:
The corrosion process in 0.5 M H2SO4 in the absence and presence of XAN follows first-order kinetics. The UV–visible absorption spectra of the solution containing the inhibitor after the immersion of mild steel specimen indicate the formation of a XAN–Fe complex. Quantum chemical calculations have been performed using DFT and several quantum chemical indices were calculated and correlated with the inhibitive effect.

In vivo

Bioavailability and antioxidant effects of a xanthone-rich Mangosteen (Garcinia mangostana) product in humans.[Pubmed: 19807152 ]

J Agric Food Chem. 2009 Oct 14;57(19):8788-92

Oxidative damage is involved in many chronic diseases including those cited as the major causes of death in Western societies such as cardiovascular disorders and cancer. Antioxidants may prevent these degenerative processes by various mechanisms including the scavenging of free radicals. Intake of antioxidant supplements is associated with preventing oxidative damages.
METHODS AND RESULTS:
This study investigated the absorption and antioxidant effects of a Xanthone-rich mangosteen liquid in healthy human volunteers after the acute consumption of 59 mL of the supplement. The liquid contained mangosteen, aloe vera, green tea, and multivitamins. Results indicated that alpha-mangostin and vitamins B(2) and B(5) were bioavailable, with observed C(max) at t(max) of around 1 h. The antioxidant capacity measured with the oxygen radical absorbance capacity (ORAC) assay was increased with a maximum effect of 18% after 2 h, and the increased antioxidant level lasted at least 4 h.
CONCLUSIONS:
Overall, this study demonstrated the bioavailability of antioxidants from a Xanthone-rich mangosteen product and its in vivo antioxidant effects.

Protocol of Xanthone

Structure Identification
Revue Canadienne De Chimie, 1963, 41(2):522-526.

Cook D . INFRARED SPECTRA OF XANTHONE: LEWIS ACID COMPLEXES.[Reference: WebLink]


METHODS AND RESULTS:
Xanthone, a member of the γ-pyrone species, which have basic carbonyl groups, forms an excellent series of solid complexes with Lewis acids. In these complexes the carbonyl oxygen atom is the donor site, and the carbonyl stretching vibration moves to progressively lower frequency as the Lewis acid strength increases. The carbonyl frequency in the BI3 complex, 1400 cm−1, is one of the lowest encountered in complexes of this type.
CONCLUSIONS:
The wide range of Lewis acids used to form these complexes has enabled a quantitative estimate of the Lewis acid strength to be made, which compares reasonably well with previous estimates.

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Background on Xanthone

Xanthone shows the antagonism of endogenous nitric oxide synthase (NOS) inhibitors, it has antitumor, antihepatotoxic, anti-inflammatory and antimicrobial activities [1]. Two derivatives of xanthone potently inhibited nitric oxide synthesis with IC50 values of 4.3 and 4.4 μM, respectively [2].

In endothelial cells, NOS synthesizes nitric oxide (NO) from L-arginine. In the maintenance of vascular structure and tone, NO has been thought to play a key role [1].

Asymmetric dimethylarginine (ADMA) is synthesized by protein arginine methyltransferases (PRMTs), using S-adenosylmethionine as methyl group donor. Dimethylarginine dimethylaminohydrolase (DDAH) degrades ADMA to L-citrulline and dimethylamine. There are two different isoforms of DDAH, DDAH-1 and DDAH-2. Typically, DDAH-1 is found in tissues containing neuronal NOS, whereas DDAH-2 predominates in tissues expressing the endothelial isoform of NOS. In cultured endothelial cells, xanthones showed the inhibition of the upregulation of MCP-1 expression, the enhancement of monocytes adhesion and the increase in the release of LDH, concomitantly with the reduction of ADMA levels. These results suggest that xanthones protect against high-lipid-level-induced endothelial damage. This protective effect of xanthones is related to the reduction of ADMA concentration [1].

A single injection of native LDL caused a rapid accumulation and oxidation of LDL in the arterial wall. At 6 to 12 h after injection of LDL, ICAM-1 expression increased and led to endothelial dysfunction and an elevation of ADMA level. In vivo, pretreatment with xanthones attenuated the effect of the injection of LDL [1].

References:
[1].  Jiang DJ, Dai Z and Li YJ. Pharmacological effects of xanthones as cardiovascular protective agents. Cardiovasc Drug Rev, 2004, 22(2):91-102.
[2].  Boonnak N, Khamthip A, Karalai C, et al. Nitric Oxide Inhibitory Activity of Xanthones from the Green Fruits of Cratoxylum formosum ssp. pruniflorum. Australian Journal of Chemistry, 2010, 63(11):1550-1556.

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References on Xanthone

Benzophenones and xanthone derivatives from Garcinia schomburgkiana-induced P-glycoprotein overexpression in human colorectal Caco-2 cells via oxidative stress-mediated mechanisms.[Pubmed:28314481]

Phytomedicine. 2017 Apr 15;27:8-14.

BACKGROUND: Up-regulation of P-gp is an adaptive survival mechanism of cancer cells from chemotherapy. Three new phytochemicals including two benzophenones, guttiferone K (GK) and oblongifolin C (OC), and a Xanthone, isojacaruebin (ISO), are potential anti-cancer agents. However, the capability of these compounds to increase multidrug-resistance (MDR) through P-gp up-regulation in cancer cells has not been reported. PURPOSE: This study was to investigate the effects of GK, OC and ISO on P-gp up-regulation in colorectal adenocarcinoma cells (Caco-2 cells). In addition, the mechanisms underlying their inductive effect were also determined. METHODS: The inductive effect of GK, OC and ISO on P-gp expression at transcription level was measured by real-time reverse transcription polymerase chain reaction. The reactive oxygen species production was determined by 2', 7'-dichlorofluorescin diacetate assay. The protein content of P-gp and involvement of mitogen-activated protein kinases (MAPK) pathway was evaluated by western blot analysis. RESULTS: GK, OC and ISO (50 microM, 24 h) were able to increase the amount of MDR1 mRNA and protein in Caco-2 cells. The presence of N-acetyl-l-cysteine significantly prevented the inductive effect of GK, OC and ISO on MDR1 mRNA level. Moreover, MAPK inhibitors including U0126 (an ERK1/2/MAPK inhibitor) and SB202190 (p38/MAPK inhibitor) suppressed an increase of MDR1 mRNA levels in the cells treated with benzophenones (GK, OC) and Xanthone ISO, respectively. These findings were in agreement with the increase of phosphorylated form of either ERK1/2 (p-ERK1/2) or p38 (p-p38) upon treatment of the cells with these three compounds. In addition, OC and ISO, but not GK, increased mRNA of c-Jun level. CONCLUSION: The benzophenones GK, OC and Xanthone ISO are likely MDR inducers through up-regulation of P-gp expression at transcription level. Their molecular mechanisms involve oxidative stress-mediated activation of MAPK signaling pathway.

Large-Scale Preparation of a Specific Xanthone from Swertia mussotii and Evaluation of Its alpha-Glucosidase Inhibitory Activity.[Pubmed:28334929]

J Chromatogr Sci. 2017 Jul 1;55(6):638-644.

Large-scale preparation and alpha-glucosidase inhibitory activity of a specific Xanthone swertioside from Swertia mussotii were investigated in this study. Firstly, an efficient method was successfully established by liquid-liquid extraction, preparative high-performance liquid chromatography and sephadex LH-20 for large-scale preparation of swertioside. The recovery of swertioside reached 92.0%. Secondly, in vitro alpha-glucosidase inhibition experiment showed that swertioside had good inhibition close to acarbose. The study showed that swertioside had potential use as an anti-diabetic agent.

Penixanthones A and B, two new xanthone derivatives from fungus Penicillium sp. SYFz-1 derived of mangrove soil sample.[Pubmed:28299980]

Nat Prod Res. 2017 Oct;31(19):2218-2222.

Two new Xanthone derivatives, peniXanthones A (1) and B (2), together with three known compounds, aspenicillide (3), 1,5-dihydroxy-3-methoxy-7-methyl-anthracene-9,10-dione (4) and 1,2-indandiol (5), were isolated from the ethyl acetate extract of a culture of the fungus Penicillium sp. SYFz-1, which was separated from a mangrove soil sample. The structures of these compounds were elucidated by spectroscopic methods including NMR and mass spectrometry. The absolute configurations of peniXanthones A (1) and B (2) were determined on the basis of electronic circular dichroism (ECD) data analysis.

Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.[Pubmed:28376372]

Eur J Med Chem. 2017 Jun 16;133:50-61.

34 Xanthones were synthesized by microwave assisted technique. Their in vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231 cell line growth with an IC50 of 0.46 +/- 0.03 muM. Combination of 3-1 and 5,6-dimethylXanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy.

Description

Xanthone is isolated from Mangosteen and is known to control cell division and growth, apoptosis, inflammation, and metastasis in different stages of carcinogenesis. Xanthone has anti-oxidant, anti-tumor, anti-allergic, anti-inflammatory, anti-bacterial, anti-fungal, and anti-viral activities.

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