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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
358
Targets

Targets

Primary TargetPharmacologyConditionPotency
Histamine H1 receptor
315
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
Antagonist
2778
Sphingomyelin phosphodiesterase
7
Target ID: P17405
Gene ID: 6609.0
Gene Symbol: SMPD1
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 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
8297
 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
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Biological activities of alpha-mangostin derivatives against acidic sphingomyelinase.
2003 Oct 6
Alpha-mangostin induces Ca2+-ATPase-dependent apoptosis via mitochondrial pathway in PC12 cells.
2004 May
Antimicrobial effects of Thai medicinal plants against acne-inducing bacteria.
2005 Oct 3
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Apoptotic effects on B-cell chronic lymphocytic leukemia (B-CLL) cells of heterocyclic compounds isolated from Guttiferaes.
2008 Dec
Garcinia mangostana: a source of potential anti-cancer lead compounds against CEM-SS cell line.
2008 May-Jun
Thin-layer chromatography-densitometric analysis of alpha-mangostin content in Garcinia mangostana fruit rind extracts.
2008 Sep-Oct
Renoprotection by alpha-Mangostin is related to the attenuation in renal oxidative/nitrosative stress induced by cisplatin nephrotoxicity.
2009
Antioxidant activity of mangostin in cell-free system and its effect on K562 leukemia cell line in photodynamic therapy.
2009 Dec
Anti-oxidative and anti-inflammatory activities of some isolated constituents from the stem bark of Allanblackia monticola Staner L.C (Guttiferae).
2009 Feb
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 Feb 25
Bioaccessibility, biotransformation, and transport of alpha-mangostin from Garcinia mangostana (Mangosteen) using simulated digestion and Caco-2 human intestinal cells.
2009 May
Anti-acne-inducing bacterial activity of mangosteen fruit rind extracts.
2010
Apoptotic effects of γ-mangostin from the fruit hull of Garcinia mangostana on human malignant glioma cells.
2010 Dec 7
Effects of alpha-mangostin on mitochondrial energetic metabolism.
2010 Mar
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 Sep
Neuroprotective Effects of Alpha-Mangostin on MPP(+)-Induced Apoptotic Cell Death in Neuroblastoma SH-SY5Y Cells.
2015
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 Sat Dec 16 04:29:21 UTC 2023
Edited
by admin
on Sat Dec 16 04:29:21 UTC 2023
Record UNII
U6RIV93RU1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANGOSTIN
INCI   MI  
INCI  
Official Name English
MANGOSTIN [MI]
Common Name English
MANGOSTIN [INCI]
Common Name English
NSC-139154
Code 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 Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
Code System Code Type Description
HSDB
8103
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
CAS
6147-11-1
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
NSC
30552
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
PUBCHEM
5281650
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
DRUG BANK
DB14371
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
WIKIPEDIA
MANGOSTIN
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
DAILYMED
U6RIV93RU1
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID00210420
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
MESH
C021053
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
NSC
139154
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
CHEBI
67547
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
NSC
27593
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
FDA UNII
U6RIV93RU1
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
MERCK INDEX
m7077
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY Merck Index
RXCUI
2619910
Created by admin on Sat Dec 16 04:29:21 UTC 2023 , Edited by admin on Sat Dec 16 04:29:21 UTC 2023
PRIMARY
Related Record Type Details
GARCINIA MANGOSTANA FRUIT RIND
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