20931-37-7

Basic information

• Product Name: Beta-mangostin
• Synonyms: Beta-mangostin;1,6-Dihydroxy-3,7-dimethoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one;1,6-Dihydroxy-3,7-dimethoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one;Beta-mangostin β-Mangostin;β-Mangostin, 98%, from Garcinia mangostana L.
• CAS NO: 20931-37-7
• Molecular Formula: C25H28O6
• Molecular Weight: 424.49
• Product Categories: reagent;standard substance
• Mol File: 20931-37-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 175-176℃
• Boiling Point: 616.5 °C at 760 mmHg
• Flash Point: 208.3 °C
• Appearance: /
• Density: 1.212
• Vapor Pressure: 8.64E-16mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: 2-8°C
• PKA: 7.05±0.20(Predicted)
• CAS DataBase Reference: Beta-mangostin(CAS DataBase Reference)
• NIST Chemistry Reference: Beta-mangostin(20931-37-7)
• EPA Substance Registry System: Beta-mangostin(20931-37-7)

Safety Data

• Hazardous Substances Data: 20931-37-7(Hazardous Substances Data)

Usage

Description

β-Mangostin is a xanthone originally isolated from G. mangostana with diverse biological activites. It inhibits growth of methicillin-resistant S. aureus (MRSA) and methicillin-susceptible S. aureus (MSSA; MICs = 6.25-12.5 and 6.25-25 μg/ml, respectively), P. falciparum (IC50 = 3 μg/ml), and M. tuberculosis (MIC = 6.25 μg/ml). β-Mangostin inhibits fatty acid synthase (FASN) with an IC50 value of 24.83 μM. It induces cell cycle arrest at the G2/M phase and intrinsic and mitochondrial apoptosis in MCF-7 breast cancer cells. β-Mangostin also inhibits LPS-induced nitric oxide and prostaglandin E2 (PGE2; ) production in RAW264.7 cells and reduces neutrophil infiltration and TNF-α and IL-1β production in a mouse model of carrageenan-induced peritonitis.

InChI:InChI=1/C25H28O6/c1-13(2)7-9-15-18(29-5)12-20-22(23(15)27)24(28)21-16(10-8-14(3)4)25(30-6)17(26)11-19(21)31-20/h7-8,11-12,26-27H,9-10H2,1-6H3

Upstream product

• 65697-05-4 3,6-dimethoxy-1,7-dihydroxy-2,8-diallyl-9H-xanthone 
• 132031-39-1 3,6-dimethoxy-1,7-dihydroxy-2,8-diisopent-2-enyl-9H-xanthone 
• 42833-92-1 1,7-dihydroxy-3,6-dimethoxy-9H-xanthen-9-one 
• 15404-76-9 dimethylmangostin 
• 1193121-26-4 3-(allyloxy)-6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-en-1-yl)-9H-xanthene-9-one 
• 6147-11-1 α-mangostin 
• 1607022-18-3 3-(allyloxy)-8-hydroxy-2,6-dimethoxy-1,7-bis(3-methylbut-2-en-1-yl)-9H-xanthene-9-one 
• 15404-67-8 dimethyl-1-isonormangostin 
• 77-78-1 dimethyl sulfate 
• 15404-68-9 3',3''-dichlorotetrahydrodimethylmangostin 
• 80902-89-2 1,7-bis(3-chloro-3-methylbutyl)-2,8-dihydroxy-3,6-dimethoxyxanthen-9-one 
• 80910-25-4 3,4-dihydro-7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-8-yl 3,4-dihydro-6,8-dimethoxy-2,2-dimethyl-2H-1-benzopyran-5-yl ketone 
• 80902-90-5 1,7-bis-(3-chloro-3-methylbutyl)-2,3,6-trimethoxy-8-methoxycarbonyloxyxanthen-9-one 

Downstream Products

• 15404-76-9 dimethylmangostin 

Relevant articles and documents

Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1

Somatic heterozygous mutations of isocitrate dehydrogenase-1 (IDH1) are abundantly found in several types of cancer and strongly implicate altered metabolism in carcinogenesis. In the present study, we have identified α-mangostin as a novel selective inhibitor of mutant IDH1 (IDH1-R132H). We have observed that α-mangostin competitively inhibits the binding of α-ketoglutarate (α-KG) to IDH1-R132H. The structure-relationship study reveals that α-mangostin exhibits the strongest core inhibitor structure. Finally, we have observed that α-mangostin selectively promotes demethylation of 5-methylcytosine (5mC) and histone H3 trimethylated lysine residues in IDH1 (+/R132H) MCF10A cells, presumably via restoring the activity of cellular α-KG-dependent DNA hydroxylases and histone H3 lysine demethylases. Collectively, we provide evidence that α-mangostin selectively inhibits IDH1-R132H.

Mangostin the whole synthetic method

The invention belongs to the field of chemical synthesis and particularly relates to a novel synthesis method of mangostin as shown in the formula (I), wherein the mangostin as a natural effective component has favorable anti-tumor activity, cardiovascular activity, antioxidant activity, anti-inflammatory activity, antibacterial activity and other pharmacological activities. The novel synthesis method comprises the steps: with 1, 7-dihydroxyl-3, 6-dialkoxyl-9H-xanthenone as a raw material, sequentially carrying out nucleophilic substitution, Claisen rearrangement, alkylation, deprotection and the like to obtain alpha-mangostin, beta-mangostin, belt-mangostin-OMe and gamma-mangostin. The novel synthesis method is simple in step and suitable for industrial production.

Synthesis of xanthone derivatives based on α-mangostin and their biological evaluation for anti-cancer agents

A xanthone-derived natural product, α-mangostin is isolated from various parts of the mangosteen, Garcinia mangostana L. (Clusiaceae), a well-known tropical fruit. Novel xanthone derivatives based on α-mangostin were synthesized and evaluated as anti-cancer agents by cytotoxicity activity screening using 5 human cancer cell lines. Some of these analogs had potent to moderate inhibitory activities. The structure-activity relationship studies revealed that phenol groups on C3 and C6 are critical to anti-proliferative activity and C4 modification is capable to improve both anti-cancer activity and drug-like properties. Our findings provide new possibilities for further explorations to improve potency.