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Chinonin

Alias: Alpizarin; Mangiferin; Chinonin
Cat No.:V18146 Purity: ≥98%
Mangiferin is an Nrf2 activator.
Chinonin
Chinonin Chemical Structure CAS No.: 4773-96-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
50mg
100mg
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Product Description
Mangiferin is an Nrf2 activator. Mangiferin inhibits nuclear translocation of NF-κB subunits p65 and p50. Mangiferin has antioxidant, antidiabetic, antihyperuricemic, antiviral, anticancer, and anti~inflammatory activities.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Mangiferin is a cellular flavonoid that has been isolated from Gentianaceae and Anacardiaceae plants. In HL-60 cells, mangiferin (50 μM) markedly boosted the accumulation of Nrf2 protein, particularly in the nucleus. Mangiferin also considerably increased the expression of NAD (P) H:quinone oxidoreductase 1 (NQO1), decreased intracellular ROS in HL60 cells, and improved the binding of Nrf2 to antioxidant response components (ARE). The growth of HL-60 cells was quantitatively reduced by mangiferin alone. Mangiferin considerably reduces oxidation in mononuclear cells (MNC) but stops embolism-induced cytotoxicity [1]. Natural plant polyphenol mangiferin has a range of pharmacological characteristics. Many plants, including Mangifera indica, contain mangiferin. Mangiferin inhibits TNF-α transcription and NF-κB activity, which in turn inhibits MMP-9 mRNA and protein expression and LNCaP cell solubility. After 24 hours of varying treatments, MTT was carried out to measure the concentration of mangiferin in the presence or absence of TNF-α under serum and serum-free conditions in order to assess if mangiferin impacts the viability of LNCaP cells. Under serum and serum-free circumstances, LNCaP cells treated with up to 400 μM mangiferin did not exhibit substantial cytotoxicity. Furthermore, mangiferin had no effect on cell survival when TNF-α (20 ng/mL) was present. In TNF-stimulated LNCaP cells, treatment with mangiferin (400 μM) dramatically decreased NF-κB luciferase activity. The NF-κB activity produced by TNF-α was dramatically reduced after an hour of cleaving with 400 μM mangiferin. Mangiferin (400 μM) dramatically reduced TNF-α-induced MMP-9 production in LNCaP cells, according to RT-PCR [2].
References

[1]. Mangiferin activates Nrf2-antioxidant response element signaling without reducing the sensitivity to etoposide of human myeloid leukemia cells in vitro. Acta Pharmacol Sin. 2014 Feb;35(2):257-66.

[2]. Mangiferin inhibits tumor necrosis factor-α-induced matrix metalloproteinase-9 expression and cellular invasion by suppressing nuclear factor-κB activity. BMB Rep. 2015 Oct;48(10):559-64.

Additional Infomation
Mangiferin is a C-glycosyl compound consisting of 1,3,6,7-tetrahydroxyxanthen-9-one having a beta-D-glucosyl residue at the 6-position. It has a role as a hypoglycemic agent, an antioxidant, an anti-inflammatory agent and a plant metabolite. It is a C-glycosyl compound and a member of xanthones. It is functionally related to a xanthone. It is a conjugate acid of a mangiferin(1-).
Mangiferin has been reported in Rigidella, Polygala tenuifolia, and other organisms with data available.
See also: Mangifera indica bark (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H18O11
Molecular Weight
422.342
Exact Mass
422.084
CAS #
4773-96-0
PubChem CID
5281647
Appearance
Off-white to yellow solid powder
Density
1.8±0.1 g/cm3
Boiling Point
842.7±65.0 °C at 760 mmHg
Melting Point
269-270ºC
Flash Point
303.6±27.8 °C
Vapour Pressure
0.0±3.3 mmHg at 25°C
Index of Refraction
1.789
LogP
0.13
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
2
Heavy Atom Count
30
Complexity
646
Defined Atom Stereocenter Count
5
SMILES
C1=C2C(=CC(=C1O)O)OC3=C(C2=O)C(=C(C(=C3)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChi Key
AEDDIBAIWPIIBD-ZJKJAXBQSA-N
InChi Code
InChI=1S/C19H18O11/c20-4-11-15(25)17(27)18(28)19(30-11)12-8(23)3-10-13(16(12)26)14(24)5-1-6(21)7(22)2-9(5)29-10/h1-3,11,15,17-23,25-28H,4H2/t11-,15-,17+,18-,19+/m1/s1
Chemical Name
1,3,6,7-tetrahydroxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one
Synonyms
Alpizarin; Mangiferin; Chinonin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~31.25 mg/mL (~73.99 mM)
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.92 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.92 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.92 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3678 mL 11.8388 mL 23.6776 mL
5 mM 0.4736 mL 2.3678 mL 4.7355 mL
10 mM 0.2368 mL 1.1839 mL 2.3678 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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