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Details

Stereochemistry ACHIRAL
Molecular Formula C24H26O6
Molecular Weight 410.4596
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANGOSTIN

SMILES

COC1=C(CC=C(C)C)C2=C(OC3=C(C2=O)C(O)=C(CC=C(C)C)C(O)=C3)C=C1O

InChI

InChIKey=GNRIZKKCNOBBMO-UHFFFAOYSA-N
InChI=1S/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3

HIDE SMILES / InChI
Molecular Formula C24H26O6
Molecular Weight 410.4596
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

α-Mangostin is a bioactive compound isolated from Garcinia mangostana L. known as the queen of fruits. Traditionally, numerous parts of G. mangostana have been utilized to treat various ailments such as abdominal pain, food allergies, arthritis, leucorrhoea, gonorrhea, diarrhea, and chronic ulcer. Experiments on animal have revealed that alpha-mangostin, an acid sphingomyelinase inhibitor, plays a protective role in diabetic neuropathy by relieving ER stress induced-renal cell apoptosis. Besides, it used against gastric ulcer, but this study was discontinued. α-Mangostin is also a histamine H1 receptor antagonist and is a specific inhibitor of lysine-specific demethylase 1 (LSD1), which has been reported to be overexpressed in several human cancers. α-mangostin has anti-carcinogenic effects against several cancers, including breast, colorectal cancers, and renal cell carcinoma. Thus, α-mangostin can be used to produce more potent LSD1 inhibitors with potential anticancer activity.

CNS Activity

Originator

Approval Year

2022
324
Targets

Targets

Primary TargetPharmacologyConditionPotency
Histamine H1 receptor
316
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
Antagonist
2849
Sphingomyelin phosphodiesterase
7
Target ID: P17405
Gene ID: 6609.0
Gene Symbol: SMPD1
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 14.1 µM [IC50]
Lysine-specific histone demethylase 1A
1
Target ID: O60341|||Q96AW4
Gene ID: 23028.0
Gene Symbol: KDM1A
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 2.81 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Palliative
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Neuroprotective Effects of Alpha-Mangostin on MPP(+)-Induced Apoptotic Cell Death in Neuroblastoma SH-SY5Y Cells.
2015
α-Mangostin-induced apoptosis is mediated by estrogen receptor α in human breast cancer cells.
2014-04
Anti-cancer effects of naturally occurring compounds through modulation of signal transduction and miRNA expression in human colon cancer cells.
2013-11
Phytochemical, antimicrobial and antiprotozoal evaluation of Garcinia mangostana pericarp and α-mangostin, its major xanthone derivative.
2013-09-02
Oxidative stress contributes to outcome severity in a Drosophila melanogaster model of classic galactosemia.
2013-01
Apoptotic effects of γ-mangostin from the fruit hull of Garcinia mangostana on human malignant glioma cells.
2010-12-07
The alpha-mangostin prevention on cisplatin-induced apoptotic death in LLC-PK1 cells is associated to an inhibition of ROS production and p53 induction.
2010-10-06
Alpha-mangostin suppresses phorbol 12-myristate 13-acetate-induced MMP-2/MMP-9 expressions via alphavbeta3 integrin/FAK/ERK and NF-kappaB signaling pathway in human lung adenocarcinoma A549 cells.
2010-09
alpha-Mangostin, a novel dietary xanthone, suppresses TPA-mediated MMP-2 and MMP-9 expressions through the ERK signaling pathway in MCF-7 human breast adenocarcinoma cells.
2010-05-25
New medicinal properties of mangostins: analgesic activity and pharmacological characterization of active ingredients from the fruit hull of Garcinia mangostana L.
2010-04
The biological activity of alpha-mangostin, a larvicidal botanic mosquito sterol carrier protein-2 inhibitor.
2010-03
Effects of alpha-mangostin on mitochondrial energetic metabolism.
2010-03
Free radical scavenging and anti-acne activities of mangosteen fruit rind extracts prepared by different extraction methods.
2010-02
Mangifera indica (mango).
2010-01
Antioxidant, free radical-scavenging activity and cytotoxicity of different solvent extracts and their phenolic constituents from the fruit hull of mangosteen (Garcinia mangostana).
2010-01
Anti-acne-inducing bacterial activity of mangosteen fruit rind extracts.
2010
Antioxidant activity of mangostin in cell-free system and its effect on K562 leukemia cell line in photodynamic therapy.
2009-12
Bioavailability and antioxidant effects of a xanthone-rich Mangosteen (Garcinia mangostana) product in humans.
2009-10-14
Antifungal activity of alpha-mangostin against Candida albicans.
2009-09
ROS scavenging capacity and neuroprotective effect of alpha-mangostin against 3-nitropropionic acid in cerebellar granule neurons.
2009-09
Cytotoxic geranylated xanthones and O-alkylated derivatives of alpha-mangostin.
2009-08
Bioaccessibility, biotransformation, and transport of alpha-mangostin from Garcinia mangostana (Mangosteen) using simulated digestion and Caco-2 human intestinal cells.
2009-05
Validation of LC for the determination of alpha-mangostin in mangosteen peel extract: a tool for quality assessment of Garcinia mangostana L.
2009-03
Antibacterial activity of Thai medicinal plants against methicillin-resistant Staphylococcus aureus.
2009-03
Alpha-mangostin suppresses PC-3 human prostate carcinoma cell metastasis by inhibiting matrix metalloproteinase-2/9 and urokinase-plasminogen expression through the JNK signaling pathway.
2009-02-25
The natural xanthone alpha-mangostin reduces oxidative damage in rat brain tissue.
2009-02
Anti-oxidative and anti-inflammatory activities of some isolated constituents from the stem bark of Allanblackia monticola Staner L.C (Guttiferae).
2009-02
Renoprotection by alpha-Mangostin is related to the attenuation in renal oxidative/nitrosative stress induced by cisplatin nephrotoxicity.
2009
Mitigation of mitochondrial dysfunction and regulation of eNOS expression during experimental myocardial necrosis by alpha-mangostin, a xanthonic derivative from Garcinia mangostana.
2009
Apoptotic effects on B-cell chronic lymphocytic leukemia (B-CLL) cells of heterocyclic compounds isolated from Guttiferaes.
2008-12
Thin-layer chromatography-densitometric analysis of alpha-mangostin content in Garcinia mangostana fruit rind extracts.
2008-11-05
Cancer is a preventable disease that requires major lifestyle changes.
2008-09
Ameliorative prospective of alpha-mangostin, a xanthone derivative from Garcinia mangostana against beta-adrenergic cathecolamine-induced myocardial toxicity and anomalous cardiac TNF-alpha and COX-2 expressions in rats.
2008-08
Xanthones from the botanical dietary supplement mangosteen (Garcinia mangostana) with aromatase inhibitory activity.
2008-07
Garcinia mangostana: a source of potential anti-cancer lead compounds against CEM-SS cell line.
2008-05-09
Anti-cancer effects of xanthones from pericarps of mangosteen.
2008-03
Anti-inflammatory activity of mangostins from Garcinia mangostana.
2008-02
Oligomeric proanthocyanidins from mangosteen pericarps.
2007-09-19
Characterized mechanism of alpha-mangostin-induced cell death: caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells.
2007-08-15
HPLC analysis of selected xanthones in mangosteen fruit.
2007-06
Antimalarial and vasorelaxant constituents of the leaves of Allanblackia monticola (Guttiferae).
2007-01
Effects of alpha-mangostin from mangosteen pericarp extract and imidacloprid on Nilaparvata lugens (Stal.) and non-target organisms: toxicity and detoxification mechanism.
2007
Cardioprotective effect of alpha-mangostin, a xanthone derivative from mangosteen on tissue defense system against isoproterenol-induced myocardial infarction in rats.
2007
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Natural products that reduce rotavirus infectivity identified by a cell-based moderate-throughput screening assay.
2006-09-01
Prenylated xanthones as potential antiplasmodial substances.
2006-08
Garcinone B reduces prostaglandin E2 release and NF-kappaB-mediated transcription in C6 rat glioma cells.
2006-02-20
Prenylated xanthone derivatives with antiplasmodial activity from Allanblackia monticola STANER L.C.
2006-01
The novel botanical insecticide for the control brown planthopper (Nilaparvata lugens Stal.).
2006
Active constituents against HIV-1 protease from Garcinia mangostana.
1996-08
Patents

Patents

JP2001247469A
1
JP2002047180A
1
JP2004194554A
1
JP2005075791A
1
JP2011524337A
22
JPH04154804A
4
JPH09110688A
1

Sample Use Guides

In Vivo Use Guide
type 2 diabetic rats: Alpha-mangostin (200 mg/kg BW/day) were fed followed by i.p. injection of streptozotocin
Route of Administration: Oral
In Vitro Use Guide
α-mangostin at 10 μg/ml significantly suppressed the expression and phosphorylation of key proteins implicated in NF-κB pathway and inhibited nucleus translocation of p65. These changes led to increased apoptosis and proliferation inhibition of HFLS-RA cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:22:23 GMT 2025
Edited
by admin
on Mon Mar 31 21:22:23 GMT 2025
Record UNII
U6RIV93RU1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANGOSTIN
INCI   MI  
INCI  
Official Name English
NSC-139154
Preferred Name English
MANGOSTIN [MI]
Common Name English
.ALPHA.-MANGOSTEN
Common Name English
NSC-30552
Code English
1,3,6-TRIHYDROXY-7-METHOXY-2,8-BIS-(3-METHYL-2-BUTEN-1-YL)-9H-XANTHEN-9-ONE
Systematic Name English
7-O-METHYL-4-DESPRENYLCOSTATIN
Common Name English
.ALPHA.-MANGOSTIN
Common Name English
1,3,6-TRIHYDROXY-7-METHOXY-2,8-DI(3-METHYL-2-BUTENYL)XANTHONE
Systematic Name English
NSC-27593
Code English
7-O-METHYL-.GAMMA.-MANGOSTIN
Common Name English
1,3,6-TRIHYDROXY-7-METHOXY-2,8-BIS(3,3-DIMETHYLALLYL)XANTHONE
Systematic Name English
9H-XANTHEN-9-ONE, 1,3,6-TRIHYDROXY-7-METHOXY-2,8-BIS(3-METHYL-2-BUTENYL)-
Systematic Name English
XANTHEN-9-ONE, 1,3,6-TRIHYDROXY-7-METHOXY-2,8-BIS(3-METHYL-2-BUTENYL)-
Systematic Name English
Classification Tree Code System Code
DSLD 3371 (Number of products:1)
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
Code System Code Type Description
HSDB
8103
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
CAS
6147-11-1
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
NSC
30552
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
PUBCHEM
5281650
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
DRUG BANK
DB14371
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
WIKIPEDIA
MANGOSTIN
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
DAILYMED
U6RIV93RU1
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID00210420
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
MESH
C021053
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
NSC
139154
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
CHEBI
67547
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
NSC
27593
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
FDA UNII
U6RIV93RU1
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
MERCK INDEX
m7077
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY Merck Index
RXCUI
2619910
Created by admin on Mon Mar 31 21:22:23 GMT 2025 , Edited by admin on Mon Mar 31 21:22:23 GMT 2025
PRIMARY
Related Record Type Details
GARCINIA MANGOSTANA FRUIT RIND
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