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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H18O11
Molecular Weight 422.3404
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANGIFERIN

SMILES

c1c2c(cc(c1O)O)oc3cc(c(c(c3c2=O)O)[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O4)O)O)O)O

InChI

InChIKey=AEDDIBAIWPIIBD-ZJKJAXBQSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H18O11
Molecular Weight 422.3404
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Mangiferin, a bioactive compound derived primarily from Anacardiaceae and Gentianaceae families and found in mangoes and honeybush tea, has been extensively studied for its therapeutic properties. Mangiferin has shown promising chemotherapeutic and chemopreventative potential. In traditional medicine, different cultures have cultivated and processed mangiferin rich plants for the treatment of a range of illnesses including cardiovascular disease, diabetes, infection and cancer. Mangiferin is primarily implicated in down-regulating inflammation, causing cell cycle arrest, reducing proliferation/metastasis, promoting apoptosis in malignant cells and protecting against oxidative stress and DNA damage. Mangiferin also enhances the capacity of the monocyte-macrophage system and possesses antibacterial activity against gram-positive and gram-negative bacteria.

CNS Activity

Curator's Comment:: Mangiferin stimulated CNS, potentiated subanalgesic doses of morphine and exerted cardiostimulant and hydrocholeretic action on i.p. administration to mice, rats and dogs.

Approval Year

TargetsConditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
19.94 ng/mL
0.2 g single, oral
dose: 0.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
34.7 ng/mL
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
38.64 ng/mL
0.9 g single, oral
dose: 0.9 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
167.9 ng × h/mL
0.2 g single, oral
dose: 0.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
269.35 ng × h/mL
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
415.14 ng × h/mL
0.9 g single, oral
dose: 0.9 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.47 h
0.2 g single, oral
dose: 0.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.8 h
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.85 h
0.9 g single, oral
dose: 0.9 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MANGIFERIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
900 mg single, oral (unknown)
Highest studied dose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources:
healthy
n = 7
Health Status: healthy
Sex: M
Food Status: FASTED
Population Size: 7
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely [Inhibition 100 uM]
likely [Inhibition 100 uM]
moderate [Inhibition 100 uM]
no [Inhibition 100 uM]
no [Inhibition 100 uM]
no [Inhibition 100 uM]
no [Inhibition 100 uM]
no [Inhibition 100 uM]
no [Inhibition 100 uM]
no [Inhibition 100 uM]
no
no
weak [Inhibition 100 uM]
yes [IC50 12.3 uM]
yes [IC50 4.4 uM]
yes [IC50 8.2 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Scavenging effect of Chinonin on NO and oxygen free radicals and its protective effect on the myocardium from the injury of ischemia-reperfusion.
1996 Mar 1
Antitumor, immunomodulatory and anti-HIV effect of mangiferin, a naturally occurring glucosylxanthone.
1996 Nov-Dec
New antidiabetic compounds, mangiferin and its glucoside.
1998 Dec
The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan.
1998 Dec
Cytoprotective effect of mangiferin on benzo(a)pyrene-induced lung carcinogenesis in swiss albino mice.
2008 Aug
Protective effects of Mangifera indica L extract (Vimang), and its major component mangiferin, on iron-induced oxidative damage to rat serum and liver.
2008 Jan
Protective role of mangiferin against Benzo(a)pyrene induced lung carcinogenesis in experimental animals.
2008 Jun
Modulation of P450 enzymes by Cuban natural products rich in polyphenolic compounds in rat hepatocytes.
2008 Mar 10
Mangifera indica L. extract (Vimang) and its main polyphenol mangiferin prevent mitochondrial oxidative stress in atherosclerosis-prone hypercholesterolemic mouse.
2008 May
Effect of mangiferin on benzo(a)pyrene induced lung carcinogenesis in experimental Swiss albino mice.
2008 May 20
Mangiferin inhibits cyclooxygenase-2 expression and prostaglandin E2 production in activated rat microglial cells.
2008 Sep 15
Characterization of the mangiferin-human serum albumin complex by spectroscopic and molecular modeling approaches.
2009 Apr 5
Mechanisms of blood glucose-lowering effect of aqueous extract from stems of Kothala himbutu (Salacia reticulata) in the mouse.
2009 Jan 21
Effect of mangiferin on the development of periodontal disease: involvement of lipoxin A4, anti-chemotaxic action in leukocyte rolling.
2009 May 15
Agarwood induced laxative effects via acetylcholine receptors on loperamide-induced constipation in mice.
2010
In vitro modulation of ABCB1/P-glycoprotein expression by polyphenols from Mangifera indica.
2010 Aug 5
A Mangifera indica L. extract could be used to treat neuropathic pain and implication of mangiferin.
2010 Dec 9
[Effects of mangiferin on cell cycle status and CDC2/Cyclin B1 expression of HL-60 cells].
2010 Jan
Mangiferin prevents diabetic nephropathy progression in streptozotocin-induced diabetic rats.
2010 Jun
Mangiferin, a naturally occurring glucoxilxanthone improves long-term object recognition memory in rats.
2010 Jun 10
Study on interaction of mangiferin to insulin and glucagon in ternary system.
2010 May
[Mangiferin promotes uric acid excretion and kidney function improvement and modulates related renal transporters in hyperuricemic mice].
2010 Oct
Establishment of a novel model for studying the effects of extracts of Chinese herb medicine on human type II 5alpha-reductase in vitro.
2010 Sep
The Ayurvedic Medicine Salacia oblonga Attenuates Diabetic Renal Fibrosis in Rats: Suppression of Angiotensin II/AT1 Signaling.
2011
Mangiferin: a possible strategy for periodontal disease to therapy.
2011 Apr
Polysulfated xanthones: multipathway development of a new generation of dual anticoagulant/antiplatelet agents.
2011 Aug 11
Beneficial effects of mangiferin on hyperlipidemia in high-fat-fed hamsters.
2011 Dec
Mangiferin attenuates osteoclastogenesis, bone resorption, and RANKL-induced activation of NF-κB and ERK.
2011 Jan
Gallic acid indanone and mangiferin xanthone are strong determinants of immunosuppressive anti-tumour effects of Mangifera indica L. bark in MDA-MB231 breast cancer cells.
2011 Jun 1
Mangiferin induces apoptosis by suppressing Bcl-xL and XIAP expressions and nuclear entry of NF-κB in HL-60 cells.
2011 Mar
[Effects of mangiferin on cytokines in rats with chronic bronchitis and expression of macrophage COX-2 in mice].
2011 May
Mangiferin, an anti-HIV-1 agent targeting protease and effective against resistant strains.
2011 May 24
Mangiferin ameliorates 6-hydroxydopamine-induced cytotoxicity and oxidative stress in ketamine model of schizophrenia.
2012
Combination of mangiferin and dipeptidyl peptidase-4 inhibitor sitagliptin improves impaired glucose tolerance in streptozotocin-diabetic rats.
2012
Cardioprotective effect of mangiferin on left ventricular remodeling in rats.
2012
Mangiferin decreases plasma free fatty acids through promoting its catabolism in liver by activation of AMPK.
2012
D(+) galactosamine induced oxidative and nitrosative stress-mediated renal damage in rats via NF-κB and inducible nitric oxide synthase (iNOS) pathways is ameliorated by a polyphenol xanthone, mangiferin.
2012 Feb
Mangiferin, a dietary xanthone protects against mercury-induced toxicity in HepG2 cells.
2012 Feb
Norathyriol suppresses skin cancers induced by solar ultraviolet radiation by targeting ERK kinases.
2012 Jan 1
Selective inhibition of MMP-9 gene expression by mangiferin in PMA-stimulated human astroglioma cells: involvement of PI3K/Akt and MAPK signaling pathways.
2012 Jul
Neuropharmacological effect of Mangiferin on brain cholinesterase and brain biogenic amines in the management of Alzheimer's disease.
2012 May 15
Protective nature of mangiferin on oxidative stress and antioxidant status in tissues of streptozotocin-induced diabetic rats.
2013
Mangiferin, a natural xanthone, protects murine liver in Pb(II) induced hepatic damage and cell death via MAP kinase, NF-κB and mitochondria dependent pathways.
2013
Up-regulation of glyoxalase 1 by mangiferin prevents diabetic nephropathy progression in streptozotocin-induced diabetic rats.
2013 Dec 5
Mangifera indica L. extract and mangiferin modulate cytochrome P450 and UDP-glucuronosyltransferase enzymes in primary cultures of human hepatocytes.
2013 May
Mangiferin attenuates MPTP induced dopaminergic neurodegeneration and improves motor impairment, redox balance and Bcl-2/Bax expression in experimental Parkinson's disease mice.
2013 Nov 25
Mangiferin exerts antitumor activity in breast cancer cells by regulating matrix metalloproteinases, epithelial to mesenchymal transition, and β-catenin signaling pathway.
2013 Oct 1
Peripheral antinociceptive action of mangiferin in mouse models of experimental pain: role of endogenous opioids, K(ATP)-channels and adenosine.
2013 Sep
[Relationship between endothelial damage and p120-catenin in paraquat intoxication and the protective effect of mangiferin].
2014 Jun
Mangiferin treatment inhibits hepatic expression of acyl-coenzyme A:diacylglycerol acyltransferase-2 in fructose-fed spontaneously hypertensive rats: a link to amelioration of fatty liver.
2014 Oct 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Humans: Participants were randomly allocated to groups, either receiving mangiferin (150 mg/day, p.o) or identical placebo for 12 weeks. https://www.ncbi.nlm.nih.gov/pubmed/25989216
Mouse tumor xenograft model: Mangiferin (10, 50 and 100 mg/kg) was intraperitoneally injected into the mice, and the therapy lasted for 2 weeks
Route of Administration: Intraperitoneal
Mangiferin (30–300 uM), isolated from A. asphodeloides, specifi- cally inhibited MMP-9 gene expression in PMA-stimulated human astroglioma U87MG, U373MG, and CRT-MG cells. Mangiferin (80 uM) could inhibit the proliferation of HL-60, block the cell cycle progression in G2/M phase, and significantly increased the expressions of CDC2 mRNA and Cyclin B1 mRNA of HL-60 cells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:35:34 UTC 2021
Edited
by admin
on Sat Jun 26 16:35:34 UTC 2021
Record UNII
1M84LD0UMD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANGIFERIN
INCI   WHO-DD  
INCI  
Official Name English
HEDYSARID
Common Name English
9H-XANTHEN-9-ONE, 2-.BETA.-D-GLUCOPYRANOSYL-1,3,6,7-TETRAHYDROXY-
Common Name English
MANGIFERA INDICA BARK DRY EXTRACT [USP-RS]
Common Name English
CHINONIN
Common Name English
MANGIFERIN [INCI]
Common Name English
APHLOIOL
Common Name English
ALPIZARINE
Common Name English
MANGIFERIN [USP-RS]
Common Name English
NSC-248870
Code English
MANGIFERIN [WHO-DD]
Common Name English
ALPIZARIN
Common Name English
Classification Tree Code System Code
DSLD 4454 (Number of products:4)
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
Code System Code Type Description
FDA UNII
1M84LD0UMD
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY
MESH
C013592
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY
PUBCHEM
5281647
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY
USP_CATALOG
1375156
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY USP-RS
CAS
4773-96-0
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY
WIKIPEDIA
MANGIFERIN
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY
USP_CATALOG
1375173
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY USP-RS
RXCUI
1362895
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY RxNorm
EPA CompTox
4773-96-0
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY
EVMPD
SUB197209
Created by admin on Sat Jun 26 16:35:34 UTC 2021 , Edited by admin on Sat Jun 26 16:35:34 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT