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Related CAS#:
4773-96-0 13201-09-7
906328-94-7 92631-82-8

4773-96-0

4773-96-0 structure
4773-96-0 structure
  • Name: Mangiferin
  • Chemical Name: mangiferin
  • CAS Number: 4773-96-0
  • Molecular Formula: C19H18O11
  • Molecular Weight: 422.340
  • Catalog: Natural product Xanthone
  • Create Date: 2018-10-01 17:36:17
  • Modify Date: 2024-01-01 18:49:45
  • Mangiferin is a Nrf2 activator. Mangiferin suppresses nuclear translocation of the NF-κB subunits p65 and p50.
Name mangiferin
Synonyms Hedysaride
(1S)-1,5-Anhydro-1-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)-D-glucitol
D-Glucitol, 1,5-anhydro-1-C-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)-, (1S)-
hedysarid
MANGIFERN
1,3,6,7-Tétrahydroxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]-9H-xanthén-9-one
aphloiol
chinonin
9H-Xanthen-9-one, 2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-
chinomin
MFCD00075656
Alpizarine
alpizarin
1,3,6,7-Tetrahydroxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-9H-xanthen-9-on
1,3,6,7-Tetrahydroxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-9H-xanthen-9-one
Mangiferin
ChinoMine
Description Mangiferin is a Nrf2 activator. Mangiferin suppresses nuclear translocation of the NF-κB subunits p65 and p50.
Related Catalog
Target

p65

p50

Nrf2
In Vitro Mangiferin is glucosylxanthone extracted from plants of the Anacardiaceae and Gentianaceae families. Mangiferin (50 μM) significantly increases Nrf2 protein accumulation in HL-60 cells, particularly in the nucleus. Mangiferin also enhances the binding of Nrf2 to an antioxidant response element (ARE), significantly up-regulates NAD(P)H:quinone oxidoreductase 1 (NQO1) expression and reduces intracellular ROS in HL60 cells. Mangiferin alone dose-dependently inhibits the proliferation of HL-60 cells. In mononuclear cells (MNCs), Mangiferin significantly relieves oxidative stress, but attenuates etoposide-induced cytotoxicity[1]. Mangiferin is a natural phytopolyphenol that exhibits various pharmacological properties. Mangiferin is present in several plant species such as Mangifera indica, Iris unguicularis, and Anemarrhena asphodeloides. Mangiferin downregulates TNF-α-induced MMP-9 mRNA and protein expression by suppressing NF-κB activity, consequently suppressing the invasion of LNCaP cells.To assess whether Mangiferin influences the viability of LNCaP cells, MTT assay is performed 24 h after treatment with different concentrations of Mangiferin in the presence or absence of TNF-α in serum and serum-free conditions. There are no cytotoxic evident in LNCaP cells treated with up to 400 μM of Mangiferin alone under both serum and serum-free conditions. Additionally, in the presence of TNF-α (20 ng/mL), Mangiferin does not affect cell viability. Mangiferin (400 μM) treatment significantly decreases the NF-κB luciferase activity in TNF-α-stimulated LNCaP cells. Pretreatment with Mangiferin (400 μM) for 1 h significantly decreases TNF-α-induced NF-κB activity. The RT-PCR shows that Mangiferin (400 μM) significantly suppresses the TNF-α-induced MMP-9 expression in LNCaP cells[2].
Cell Assay LNCaP cells are cultured at 37°C in 5% CO2 in RPMI supplemented with 10% FBS and antibiotics. Cell viability is determined by an MTT assay. Briefly, LNCaP cells (1×105 cells/mL) are plated onto 24 well plates and incubated overnight in serum and serum-free RPMI media. The cells are treated with the indicated concentrations of Mangiferin (100, 200, and 400 μM) for 1 h and then stimulated with TNF-α (20 ng/mL) for 24 h. Then, the cells are incubated with a solution of 0.5 mg/mL MTT and incubation for 45 min at 37°C and 5% CO2. Supernatant is removed and the formation of formazan is observed by monitoring the signal at 540 nm using a microplate reader[2].
References

[1]. Zhang BP, et al. 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]. Dilshara MG, et al. 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.
Density 1.8±0.1 g/cm3
Boiling Point 842.7±65.0 °C at 760 mmHg
Melting Point 269-270ºC
Molecular Formula C19H18O11
Molecular Weight 422.340
Flash Point 303.6±27.8 °C
Exact Mass 422.084900
PSA 201.28000
LogP 0.13
Vapour Pressure 0.0±3.3 mmHg at 25°C
Index of Refraction 1.789
Storage condition 2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OP1927800
CHEMICAL NAME :
Mangiferin
CAS REGISTRY NUMBER :
4773-96-0
LAST UPDATED :
199712
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C19-H18-O11
MOLECULAR WEIGHT :
422.37

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
365 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 61,1838,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PBVMA9 Problemi na Vutreshnata Meditsina. Problems of Internal Medicine. (Durzhavno Izdatel'stvo Meditsina i Fizkultura, Pl. Slaveikov 11, Sofia, Bulgaria) V.1- 1973- Volume(issue)/page/year: 8(2),109,1980
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T+:Verytoxic;
Risk Phrases R28
Safety Phrases S22-S28-S36/37-S45
RIDADR UN 3462
WGK Germany 3
RTECS OP1927800
Hazard Class 6.1
Precursor  1

DownStream  2


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