MANGOSTIN

Possibly Marketed Outside US

First approved in 2022

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23634169 | https://www.ncbi.nlm.nih.gov/pubmed/29317203 | https://www.ncbi.nlm.nih.gov/pubmed/29274582 | https://www.ncbi.nlm.nih.gov/pubmed/29190630

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

Targets

Primary Target	Pharmacology	Potency
Histamine H1 receptor 315 Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8957258	Antagonist 2778
Sphingomyelin phosphodiesterase 7 Target ID: P17405 Gene ID: 6609.0 Gene Symbol: SMPD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10938539	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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29274582	Inhibitor 8297	2.81 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Gastric ulcer 67 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23634169	Primary	Preclinical	Unknown Approved Use Unknown
Diabetic nephropathy 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29317203	Palliative	Preclinical	Unknown Approved Use Unknown
Renal cell carcinoma 31 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29190630	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory effects of crude alpha-mangostin, a xanthone derivative, on two different categories of colon preneoplastic lesions induced by 1, 2-dimethylhydrazine in the rat.	2004 Oct-Dec	15546251
Xanthones induce cell-cycle arrest and apoptosis in human colon cancer DLD-1 cells.	2005 Nov 1	16112579
Antimicrobial effects of Thai medicinal plants against acne-inducing bacteria.	2005 Oct 3	16009519
Prenylated xanthones as potential antiplasmodial substances.	2006 Aug	16902859
Garcinone B reduces prostaglandin E2 release and NF-kappaB-mediated transcription in C6 rat glioma cells.	2006 Feb 20	16260090
Prenylated xanthone derivatives with antiplasmodial activity from Allanblackia monticola STANER L.C.	2006 Jan	16394561
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Effects of alpha-mangostin from mangosteen pericarp extract and imidacloprid on Nilaparvata lugens (Stal.) and non-target organisms: toxicity and detoxification mechanism.	2007	18399471
Cardioprotective effect of alpha-mangostin, a xanthone derivative from mangosteen on tissue defense system against isoproterenol-induced myocardial infarction in rats.	2007	17994576
Antimalarial and vasorelaxant constituents of the leaves of Allanblackia monticola (Guttiferae).	2007 Jan	17244407
Oligomeric proanthocyanidins from mangosteen pericarps.	2007 Sep 19	17715900
Anti-inflammatory activity of mangostins from Garcinia mangostana.	2008 Feb	18029076
Xanthones from the botanical dietary supplement mangosteen (Garcinia mangostana) with aromatase inhibitory activity.	2008 Jul	18558747
Antioxidant activity of mangostin in cell-free system and its effect on K562 leukemia cell line in photodynamic therapy.	2009 Dec	20011978
Antibacterial activity of Thai medicinal plants against methicillin-resistant Staphylococcus aureus.	2009 Mar	19022354
Anti-acne-inducing bacterial activity of mangosteen fruit rind extracts.	2010	20516704
New medicinal properties of mangostins: analgesic activity and pharmacological characterization of active ingredients from the fruit hull of Garcinia mangostana L.	2010 Apr	20064550
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 Jan-Feb	20492173
The biological activity of alpha-mangostin, a larvicidal botanic mosquito sterol carrier protein-2 inhibitor.	2010 Mar	20380307
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 Oct 6	20603111
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	20652762
Oxidative stress contributes to outcome severity in a Drosophila melanogaster model of classic galactosemia.	2013 Jan	22773758

Patents

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 GMT 2023` Edited by `admin` on `Sat Dec 16 04:29:21 GMT 2023`
Record UNII	U6RIV93RU1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MANGOSTIN

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)