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9-Hydroxycalabaxanthone

CAS# 35349-68-9

9-Hydroxycalabaxanthone

2D Structure

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3D structure

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9-Hydroxycalabaxanthone

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Chemical Properties of 9-Hydroxycalabaxanthone

Cas No. 35349-68-9 SDF Download SDF
PubChem ID 5495929 Appearance Yellow powder
Formula C24H24O6 M.Wt 408.5
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
SMILES CC(=CCC1=C2C(=CC(=C1OC)O)OC3=CC4=C(C=CC(O4)(C)C)C(=C3C2=O)O)C
Standard InChIKey HQWHKELJHUFLGD-UHFFFAOYSA-N
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 9-Hydroxycalabaxanthone

The fruits of Garcinia mangostana L.

Biological Activity of 9-Hydroxycalabaxanthone

Description9-Hydroxycalabaxanthone exhibits cytotoxicity against the HT-29 cell line with ED50 values of 9.1 microM. The combination of 9-hydroxycalabaxanthone with α-mangostin shows the synergistic antimalarial interaction in both clones.
TargetsAntifection
In vitro

Mangostanaxanthones I and II, new xanthones from the pericarp of Garcinia mangostana.[Pubmed: 25128900 ]

Fitoterapia. 2014 Oct;98:215-21.

Two new xanthones: mangostanaxanthones I (3) and II (5) were isolated from the pericarp of Garcinia mangostana, along with four known xanthones: 9-Hydroxycalabaxanthone (1), parvifolixanthone C (2), α-mangostin (4), and rubraxanthone (6).
METHODS AND RESULTS:
Their structures were elucidated on the basis of IR, UV, 1D, 2D NMR, and MS spectroscopic data, in addition to comparison with literature data. The isolated compounds were evaluated for their antioxidant, antimicrobial, and quorum-sensing inhibitory activities. Compounds 3 and 5 displayed promising antioxidant activity with IC50 12.07 and 14.12 μM, respectively using DPPH assay. Compounds 4-6 had weak to moderate activity against Escherichia coli and Staphylococcus aureus, while demonstrated promising action against Bacillus cereus with MICs 0.25, 1.0, and 1.0mg/mL, respectively.
CONCLUSIONS:
The tested compounds were inactive against Candida albicans. However, they showed selective antifungal potential toward Aspergillus fumigatus. Compounds 3 and 4 possessed quorum-sensing inhibitory activity against Chromobacterium violaceum ATCC 12472.

The in vitro antimalarial interaction of 9-hydroxycalabaxanthone and α-mangostin with mefloquine/artesunate.[Pubmed: 26204026]

Acta Parasitol. 2014 Mar;60(1):105-11.

Multidrug resistance Plasmodium falciparum is the major health problem in Thailand. Discovery and development of new antimalarial drugs with novel modes of action is urgently required. The aim of the present study was to investigate the antimalarial interaction of 9-Hydroxycalabaxanthone and α-mangostin with the standard antimalarial drugs mefloquine and artesunate in chloroquine sensitive (3D7) and chloroquine resistant (K1) P. falciparum clones in vitro.
METHODS AND RESULTS:
Median (range) IC50 (drug concentration which produces 50% parasite growth inhibition) values of the 9-Hydroxycalabaxanthone, α-mangostin, artesunate and mefloquine for 3D7 vs K1 clones were 1.5 (0.9-2.1) vs 1.2 (1.1-1.6) μM, 17.9 (15.7.0-20.0) vs 9.7 (6.0-14.0) μM, 1.0 (0.4-3.0) vs 1.7 (1.0-2.5) nM, and 13.3 (11.1-13.3) vs 7.1 (6.7-12.2) nM, respectively. Analysis of isobologram and combination index (CI) of 9-Hydroxycalabaxanthone with artesunate or mefloquine showed synergistic and indifference antimalarial interaction, respectively. α-mangostin-artesunate combination exhibited a slight antagonistic effect of antimalarial interaction, whereas α-mangostin and mefloquine combination showed indifference interaction in both clones.
CONCLUSIONS:
The combination of 9-Hydroxycalabaxanthone with α-mangostin showed the synergistic antimalarial interaction in both clones.

Protocol of 9-Hydroxycalabaxanthone

Structure Identification
J Nat Prod. 2009 Nov;72(11):2028-31.

Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen).[Pubmed: 19839614]


METHODS AND RESULTS:
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 4.9, 1.7, 1.7, 2.3, and 9.1 microM, respectively. In an ELISA NF-kappaB assay, compounds 5-7, 9, and 10 inhibited p65 activation with IC50 values of 15.9, 12.1, 3.2, 11.3, and 19.0 microM, respectively, and 6 showed p50 inhibitory activity with an IC50 value of 7.5 microM.
CONCLUSIONS:
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).

9-Hydroxycalabaxanthone Dilution Calculator

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Preparing Stock Solutions of 9-Hydroxycalabaxanthone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.448 mL 12.2399 mL 24.4798 mL 48.9596 mL 61.1995 mL
5 mM 0.4896 mL 2.448 mL 4.896 mL 9.7919 mL 12.2399 mL
10 mM 0.2448 mL 1.224 mL 2.448 mL 4.896 mL 6.12 mL
50 mM 0.049 mL 0.2448 mL 0.4896 mL 0.9792 mL 1.224 mL
100 mM 0.0245 mL 0.1224 mL 0.2448 mL 0.4896 mL 0.612 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 9-Hydroxycalabaxanthone

Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen).[Pubmed:19839614]

J Nat Prod. 2009 Nov;72(11):2028-31.

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 4.9, 1.7, 1.7, 2.3, and 9.1 microM, respectively. In an ELISA NF-kappaB assay, compounds 5-7, 9, and 10 inhibited p65 activation with IC50 values of 15.9, 12.1, 3.2, 11.3, and 19.0 microM, respectively, and 6 showed p50 inhibitory activity with an IC50 value of 7.5 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).

The in vitro antimalarial interaction of 9-hydroxycalabaxanthone and alpha-mangostin with mefloquine/artesunate.[Pubmed:26204026]

Acta Parasitol. 2014 Mar;60(1):105-11.

Multidrug resistance Plasmodium falciparum is the major health problem in Thailand. Discovery and development of new antimalarial drugs with novel modes of action is urgently required. The aim of the present study was to investigate the antimalarial interaction of 9-Hydroxycalabaxanthone and alpha-mangostin with the standard antimalarial drugs mefloquine and artesunate in chloroquine sensitive (3D7) and chloroquine resistant (K1) P. falciparum clones in vitro. Median (range) IC50 (drug concentration which produces 50% parasite growth inhibition) values of the 9-Hydroxycalabaxanthone, alpha-mangostin, artesunate and mefloquine for 3D7 vs K1 clones were 1.5 (0.9-2.1) vs 1.2 (1.1-1.6) muM, 17.9 (15.7.0-20.0) vs 9.7 (6.0-14.0) muM, 1.0 (0.4-3.0) vs 1.7 (1.0-2.5) nM, and 13.3 (11.1-13.3) vs 7.1 (6.7-12.2) nM, respectively. Analysis of isobologram and combination index (CI) of 9-Hydroxycalabaxanthone with artesunate or mefloquine showed synergistic and indifference antimalarial interaction, respectively. alpha-mangostin-artesunate combination exhibited a slight antagonistic effect of antimalarial interaction, whereas alpha-mangostin and mefloquine combination showed indifference interaction in both clones. The combination of 9-Hydroxycalabaxanthone with alpha-mangostin showed the synergistic antimalarial interaction in both clones.

Mangostanaxanthones I and II, new xanthones from the pericarp of Garcinia mangostana.[Pubmed:25128900]

Fitoterapia. 2014 Oct;98:215-21.

Two new xanthones: mangostanaxanthones I (3) and II (5) were isolated from the pericarp of Garcinia mangostana, along with four known xanthones: 9-Hydroxycalabaxanthone (1), parvifolixanthone C (2), alpha-mangostin (4), and rubraxanthone (6). Their structures were elucidated on the basis of IR, UV, 1D, 2D NMR, and MS spectroscopic data, in addition to comparison with literature data. The isolated compounds were evaluated for their antioxidant, antimicrobial, and quorum-sensing inhibitory activities. Compounds 3 and 5 displayed promising antioxidant activity with IC50 12.07 and 14.12 muM, respectively using DPPH assay. Compounds 4-6 had weak to moderate activity against Escherichia coli and Staphylococcus aureus, while demonstrated promising action against Bacillus cereus with MICs 0.25, 1.0, and 1.0mg/mL, respectively. The tested compounds were inactive against Candida albicans. However, they showed selective antifungal potential toward Aspergillus fumigatus. Compounds 3 and 4 possessed quorum-sensing inhibitory activity against Chromobacterium violaceum ATCC 12472.

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