Mangiferin

Names

[ Name ]:
Mangiferin

[Synonym ]:
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

Biological Activity

[Description]:

Mangiferin is a Nrf2 activator. Mangiferin suppresses nuclear translocation of the NF-κB subunits p65 and p50.

[Related Catalog]:

Signaling Pathways >> NF-κB >> Keap1-Nrf2

Research Areas >> Cancer

Natural Products >> Flavonoids

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ 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

MSDS

Click to get detail MSDS

Toxicological Information

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

Safety Information

[ Symbol ]:

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 & DownStream

Precursor

DownStream

Articles

Thermal Degradation Kinetics Modeling of Benzophenones and Xanthones during High-Temperature Oxidation of Cyclopia genistoides (L.) Vent. Plant Material.

J. Agric. Food Chem. 63 , 5518-27, (2015)

Degradation of the major benzophenones, iriflophenone-3-C-glucoside-4-O-glucoside and iriflophenone-3-C-glucoside, and the major xanthones, mangiferin and isomangiferin, of Cyclopia genistoides follow...

[Chemical constituents of Gentiana rhodantha].

Zhongguo Zhong Yao Za Zhi 38(3) , 362-5, (2013)

To determine the chemical constituents of Gentiana rhodantha.To isolate the constituents, column chromatography over silica gel, MCI, Sephadex LH-20 and C18 reverse-phased silica gel were used. Spectr...

Mangiferin activates the Nrf2-ARE pathway and reduces etoposide-induced DNA damage in human umbilical cord mononuclear blood cells.

Pharm. Biol. 53(4) , 503-11, (2015)

Mangiferin (2-C-β-d-gluco-pyranosyl-1,3,6,7-tetrahydroxyxanthone) is a well-known natural antioxidant distributed in various plants of the Anacardiaceae and Gentianaceae families. Mangiferin can inhib...