MANGIFERIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H18O11
Molecular Weight	422.3396
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C2=C(O)C3=C(OC4=C(C=C(O)C(O)=C4)C3=O)C=C2O

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27367721 | https://www.ncbi.nlm.nih.gov/pubmed/28464819 | https://www.ncbi.nlm.nih.gov/pubmed/27219221

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27417526	Inhibitor 8297
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27367721 \| https://www.ncbi.nlm.nih.gov/pubmed/28464819 \| https://www.ncbi.nlm.nih.gov/pubmed/26935347	Activator 1430
Aldose reductase 44 Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510595	Inhibitor 8297	3.2 µM [IC50]
Alpha-glucosidase MAL62 4 Target ID: CHEMBL4357 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28168055 \| https://www.ncbi.nlm.nih.gov/pubmed/22523004	Inhibitor 8297	358.54 µM [IC50]
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28664112 \| https://www.ncbi.nlm.nih.gov/pubmed/18636380	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27367721 https://www.ncbi.nlm.nih.gov/pubmed/27219221	Primary	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22426032	Primary	Preclinical	Unknown Approved Use Unknown
Dermatitis 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28222357	Primary	Preclinical	Unknown Approved Use Unknown
Ischemia-reperfusion injury 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26656757	Primary	Preclinical	Unknown Approved Use Unknown
Hyperlipidemia 80 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25989216	Primary	Phase I 428	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848064 https://www.ncbi.nlm.nih.gov/pubmed/27457691 https://www.ncbi.nlm.nih.gov/pubmed/27534809 https://www.ncbi.nlm.nih.gov/pubmed/25590730 https://www.ncbi.nlm.nih.gov/pubmed/22523004	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
19.94 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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

Value	Dose	Analyte	Population
167.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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

T_1/2

Value	Dose	Analyte	Population
4.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26434292/	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

Dose	Population	Adverse events
900 mg single, oral (unknown) Highest studied dose Dose: 900 mg Route: oral Route: single Dose: 900 mg Sources: https://pubmed.ncbi.nlm.nih.gov/26434292	healthy n = 7 Health Status: healthy Sex: M Food Status: FASTED Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/26434292	Sources: https://pubmed.ncbi.nlm.nih.gov/26434292

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 UGT1A1 204 UGT1A8 36 CYP2A6 707 UGT1A3 84 UGT1A6 108 UGT1A7 21 UGT1A10 32 UGT1A9 116 UGT2B4 19 UGT2B17 18 UGT2B7 146 P-gp 1461 MRP1 106 UGT2B15 64 BCRP 699		P-gp 257

Drug as perpetrator

Target	Modality	Activity	Metabolite
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	likely [Inhibition 100 uM]
UGT2B15 64	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	likely [Inhibition 100 uM]
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	moderate [Inhibition 100 uM]	Norathyriol 1
UGT1A10 41	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	no [Inhibition 100 uM]
UGT1A10 41	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	no [Inhibition 100 uM]	Norathyriol 1
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	no [Inhibition 100 uM]
UGT1A8 48	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	no [Inhibition 100 uM]
UGT2B17 20	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	no [Inhibition 100 uM]
UGT2B4 19	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	no [Inhibition 100 uM]
UGT2B4 19	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	no [Inhibition 100 uM]	Norathyriol 1
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/24641381/	no
MRP1 172	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/24641381/	no
UGT1A7 23	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	weak [Inhibition 100 uM]
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [IC50 12.3 uM]	Norathyriol 1
UGT1A7 23	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [IC50 4.4 uM]	Norathyriol 1
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [IC50 8.2 uM]	Norathyriol 1
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [Inhibition 100 uM]	Norathyriol 1
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [Inhibition 100 uM]	Norathyriol 1
UGT1A8 48	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [Inhibition 100 uM]	Norathyriol 1
UGT2B15 64	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [Inhibition 100 uM]	Norathyriol 1
UGT2B17 20	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28621744/	yes [Inhibition 100 uM]	Norathyriol 1
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/	yes
CYP2A6 739	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/	yes
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/	yes
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/	yes
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/	yes
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/20513373/	yes
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/24641381/	yes
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19632288/	yes	Norathyriol 1
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/ \| https://pubmed.ncbi.nlm.nih.gov/28621744/	yes
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/ \| https://pubmed.ncbi.nlm.nih.gov/28621744/	yes
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22815239/ \| https://pubmed.ncbi.nlm.nih.gov/28621744/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00I95K	https://www.1pchem.com/search?query=1P00I95K
A2B Chem	AI50872	http://a2bchem.com/prod/AI50872
AK Scientific	O907	https://aksci.com/item_detail.php?cat=O907
Ambeed	A397158	http://www.ambeed.com/search/Search.html?keyword=A397158
Angene	AGN-PC-0RVZ3C	http://www.angenechemical.com/productshow/AGN-PC-0RVZ3C.html
ApexBio Technology	N1329	https://www.apexbt.com/catalogsearch/result/?q=N1329
AstaTech	40321	http://astatechinc.com/CPSResult.php?CRNO=40321
BLD Pharm	BD33735	http://www.bldpharm.com/search/Search.html?keyword=BD33735
BOC Sciences	4773-96-0	http://www.bocsci.com/description.asp?cas=4773-96-0
BioSynth	Q-100508	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100508
Biopurify Phytochemicals	BP0922	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0922&searchhtmp=simplesearch&t=1
Chem Scene	CS-4663	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4663
Combi-Blocks	QV-5320	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-5320
Frontier Scientific Services	501003639	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=501003639&type=hts
Indofine	M-001	https://indofinechemical.com/details.aspx?Sku=M-001
KeyOrganics	AS-15337	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-15337
Lab Seeker	SC-47346	http://www.labseeker.com/search.php?keywords=SC-47346&category=0
LabSeeker	SC-47346	http://www.labseeker.com/search.php?keywords=SC-47346&category=0
MedChem Express	HY-N0290	https://www.medchemexpress.com/search.html?q=HY-N0290&ft=&fa=&fp=
MolPort	MolPort-001-741-747	https://www.molport.com/shop/molecule-link/MolPort-001-741-747
MolPort	MolPort-035-923-651	https://www.molport.com/shop/molecule-link/MolPort-035-923-651
Molnova	M18595	https://www.molnova.com/en/serch-list.html?keywords=M18595
Ryan Scientific	Gossypol_acetic_acid	https://ryansci.com/products?q=Gossypol_acetic_acid&list_q=&search_type=exact
TargetMol	BBP02160	https://www.targetmol.com/search?keyword=BBP02160
TargetMol	T3012	https://www.targetmol.com/search?keyword=T3012
Tetrahedron	TS81728	http://www.thsci.com/search.do?q=TS81728
TimTec	ST057240	http://www.echemstore.com/catalogsearch/result/?q=ST057240
Toronto Research Chemicals	M163800	https://www.trc-canada.com/product-detail/?CatNum=M163800
Vitas-M Laboratory	STL564509	http://www.vitasmlab.biz/search/STL564509
W&J PharmaChem	50C362404	http://wjpharmachem.com/new/searcht.php?keyword=50C362404
eMolecules	43296335	https://orderbb.emolecules.com/search/#?query=43296335
eMolecules	48882993	https://orderbb.emolecules.com/search/#?query=48882993
eMolecules	591853	https://orderbb.emolecules.com/search/#?query=591853
eMolecules	72980367	https://orderbb.emolecules.com/search/#?query=72980367
mcule	MCULE-2311808114	https://mcule.com/MCULE-2311808114/
mcule	MCULE-3926908782	https://mcule.com/MCULE-3926908782/

PubMed

Title	Date	PubMed
In vitro effects of mangiferin on superoxide concentrations and expression of the inducible nitric oxide synthase, tumour necrosis factor-alpha and transforming growth factor-beta genes.	2003 Apr 15	12694877
Anthelminthic and antiallergic activities of Mangifera indica L. stem bark components Vimang and mangiferin.	2003 Dec	14669257
An Anacardiaceae preparation reduces the expression of inflammation-related genes in murine macrophages.	2004 Aug	15222974
Expression profiles of genes involved in the mouse nuclear factor-kappa B signal transduction pathway are modulated by mangiferin.	2004 Jun	15135318
In vitro effects of the polyphenols resveratrol, mangiferin and (-)-epigallocatechin-3-gallate on the scuticociliate fish pathogen Philasterides dicentrarchi.	2004 May 5	15212284
Anti-allergic properties of Mangifera indica L. extract (Vimang) and contribution of its glucosylxanthone mangiferin.	2006 Mar	16536907
Novel screening assay for antioxidant protection against peroxyl radical-induced loss of protein function.	2007 Nov	17705259
Cytoprotective effect of mangiferin on benzo(a)pyrene-induced lung carcinogenesis in swiss albino mice.	2008 Aug	18816296
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	18243014
Modulation of P450 enzymes by Cuban natural products rich in polyphenolic compounds in rat hepatocytes.	2008 Mar 10	18053976
Mangiferin inhibits cyclooxygenase-2 expression and prostaglandin E2 production in activated rat microglial cells.	2008 Sep 15	18621015
Effect of mangiferin on the development of periodontal disease: involvement of lipoxin A4, anti-chemotaxic action in leukocyte rolling.	2009 May 15	19026997
In vitro modulation of ABCB1/P-glycoprotein expression by polyphenols from Mangifera indica.	2010 Aug 5	20513373
The Ayurvedic Medicine Salacia oblonga Attenuates Diabetic Renal Fibrosis in Rats: Suppression of Angiotensin II/AT1 Signaling.	2011	19706694
Mangiferin: a possible strategy for periodontal disease to therapy.	2011 Apr	21194846
Mangiferin decreases plasma free fatty acids through promoting its catabolism in liver by activation of AMPK.	2012	22292039
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	22118634
Norathyriol suppresses skin cancers induced by solar ultraviolet radiation by targeting ERK kinases.	2012 Jan 1	22084399
Protective nature of mangiferin on oxidative stress and antioxidant status in tissues of streptozotocin-induced diabetic rats.	2013	24167738
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	23451106
Up-regulation of glyoxalase 1 by mangiferin prevents diabetic nephropathy progression in streptozotocin-induced diabetic rats.	2013 Dec 5	24036348
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	24095822
Mangiferin exerts antitumor activity in breast cancer cells by regulating matrix metalloproteinases, epithelial to mesenchymal transition, and β-catenin signaling pathway.	2013 Oct 1	23707762
Peripheral antinociceptive action of mangiferin in mouse models of experimental pain: role of endogenous opioids, K(ATP)-channels and adenosine.	2013 Sep	23747933

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

MANGIFERIN

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

Mangiferin [WHO-DD]

Common Name

English

ALPIZARINE

Common Name

English

MANGIFERIN [USP-RS]

Common Name

English

NSC-248870

Code

English

ALPIZARIN

Common Name

English

Classification Tree Code System Code

DSLD

4454 (Number of products:4)