Gamma-Mangostin
(Synonyms: γ-倒捻子素,γ-Mangostin) 目录号 : GC38227
A xanthone with diverse biological activities
Cas No.:31271-07-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
γ-Mangostin is a xanthone that has been found in G. mangostana and has diverse biological activities.1,2,3,4 It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in vitro with an IC50 value of 23.6 μM.1 γ-Mangostin is cytotoxic to HL-60, SMMC-7721, A549, MCF-7, and SW480 cancer cells and BEAS-2B non-cancerous pulmonary epithelial cells in vitro (IC50s = 7.39, 6.57, 10.07, 5.33, 8.4, and 7.43 μM, respectively).2 It inhibits LPS-induced expression of IL-6, IL-10, and TNF-α in human macrophages in a concentration-dependent manner.3 Macrophage-conditioned media from macrophages pre-incubated with γ-mangostin (30 μM) prior to stimulation with LPS has a reduced ability to induce inflammation and insulin resistance in primary human adipocytes. γ-Mangostin (5 and 10 mg/kg) inhibits carbon tetrachloride-induced increases in serum levels of aspartate transaminase (AST) and alanine aminotransferase (ALT) and decreases in hepatic superoxide dismutase 2 (SOD2) activity and glutathione (GSH) content in a mouse model of liver fibrosis.4
1.Li, X.Comparative study of 1,1-diphenyl-2-picryl-hydrazyl radical (DPPH?) scavenging capacity of the antioxidant xanthones familyChemistry Select3(46)13081-13086(2018) 2.Chi, X.-Q., Zi, C.-T., Li, H.-M., et al.Design, synthesis and structure–activity relationships of mangostin analogs as cytotoxic agentsRSC Adv.8(72)41377-41388(2018) 3.Bumrungpert, A., Kalpravidh, R.W., Chuang, C.-C., et al.Xanthones from mangosteen inhibit inflammation in human macrophages and in human adipocytes exposed to macrophage-conditioned mediaJ. Nutr.140(4)842-847(2010) 4.Wang, A., Zhou, F., Li, D., et al.γ-Mangostin alleviates liver fibrosis through Sirtuin 3-superoxide-high mobility group box 1 signaling axisToxicol. Appl. Pharmacol.363142-153(2019)
| Cas No. | 31271-07-5 | SDF | |
| 别名 | γ-倒捻子素,γ-Mangostin | ||
| Canonical SMILES | O=C1C2=C(OC3=C1C(C/C=C(C)\C)=C(O)C(O)=C3)C=C(O)C(C/C=C(C)\C)=C2O | ||
| 分子式 | C23H24O6 | 分子量 | 396.43 |
| 溶解度 | DMSO: 250 mg/mL (630.63 mM) | 储存条件 | Store at 2-8°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.5225 mL | 12.6126 mL | 25.2251 mL |
| 5 mM | 0.5045 mL | 2.5225 mL | 5.045 mL |
| 10 mM | 0.2523 mL | 1.2613 mL | 2.5225 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Gamma-Mangostin isolated from garcinia mangostana suppresses colon carcinogenesis and stemness by downregulating the GSK3β/β-catenin/CDK6 cancer stem pathway
Phytomedicine 2022 Jan;95:153797.PMID:34802869DOI:10.1016/j.phymed.2021.153797.
Background: Despite advances in chemotherapies and targeted drugs, colorectal cancer (CRC) remains challenging to treat due to drug resistance. Emerging evidence indicates that cancer-associated fibroblasts (CAFs) facilitate the generation of cancer stem-like cells (CSCs) and drug resistance. Glycogen synthase kinase-3 (GSK) associated signaling pathways have been implicated in the generation of CSCs and represent a target for therapeutics development. Hypothesis: Gamma-Mangostin (gMG) isolated from Garcinia mangostana was evaluated for its ability to downregulate GSK3β-associated signaling in CRC cells and overcome CAF-induced 5-fluorouracil resistance and CSC generation. Methods: Bioinformatics analysis, in silico molecular docking, in vitro assays, including cell viability tests, colony- and tumor sphere-formation assays, transwell migration assays, ELISA, SDS-PAGE, Western blotting, miR expression, qPCR, and flow cytometry, as well as in vivo mouse xenograft models were used to evaluate the antitumor effects of gMG. Results: Bioinformatics analyses indicated that GSK3β/CDK6/β-catenin mRNA signature was significantly higher in colon cancer patients. Additional algorithms predicted a higher miR-26b level was associated with significantly higher survival in CRC patients and GSK3β and CDK6 as targets of miR-26b-5p. To validate these findings in vitro, we showed that CAF-cocultured CRC cells expressed an increased expression of GSK3β, β-catenin, CDK6, and NF-κB. Therapeutically, we demonstrated that gMG treatment suppressed GSK3β-associated signaling pathways while concomitantly increased the miR-26b-5p level. Using a xenograft mouse model of CAFs cocultured HCT116 tumorspheres, we showed that gMG treatment reduced tumor growth and overcame CAF-induced 5-fluorouracil resistance. Conclusions: Pharmacological intervention with gMG suppressed CRC carcinogenesis and stemness via downregulating GSK3/β-catenin/CDK6 and upregulating the miR-26b-5p tumor suppressor. Thus, gMG represents a potential new CRC therapeutic agent and warrants further investigation.
Protective Effects of Gamma-Mangostin on Hydrogen Peroxideinduced Cytotoxicity in Human Retinal Pigment Epithelial Cells
In Vivo 2022 Jul-Aug;36(4):1676-1683.PMID:35738618DOI:10.21873/invivo.12879.
Background: The role of epigenetic alterations in the pathogenesis of retinal degenerative diseases, such as macular degeneration is not well established. This study aimed to evaluate whether treatments with Gamma-Mangostin can rescue the hydrogen peroxide (H2O2)-induced cytotoxicity in human retinal pigment epithelial (ARPE-19) cells. Materials and methods: ARPE-19 cells were treated with H2O2 alone or with Gamma-Mangostin plus H2O2 to investigate changes relating to cell viability, appearance of sub-G1 cells, antioxidant enzymes, and apoptotic-related proteins. Results: The data showed that under H2O2 treatment of 400 μM, there was a significant decrease in cell viability and enhanced apoptosis, together with an increased expression of Bax, Bad, cleaved-caspase-3, -8, and -9 at the protein level. On the contrary, the protein expression levels of Bcl2 and Bcl-xl were decreased. Gamma-Mangostin pre-treatments (2-16 μM) could effectively prevent all alterations. Conclusion: Gamma-Mangostin may conduct its eye-protective effects against H2O2-induced oxidative damage via anti- apoptotic and antioxidant mechanisms in ARPE-19 cells.
Gamma-Mangostin, a micronutrient of mangosteen fruit, induces apoptosis in human colon cancer cells
Molecules 2012 Jul 3;17(7):8010-21.PMID:22759914DOI:10.3390/molecules17078010.
Recently colorectal cancer rates have increased rapidly in Taiwan. The treatment of colorectal cancer includes surgery, radiation therapy and chemotherapy. Mangosteen (Garcinia mangostana) is a famous Asian tropical fruit. γ-Mangostin is a xanthone derivative isolated from the fruit hull. In previous studies, we found evidence of anti-inflammatory and anti-brain tumor activities in γ-mangostin. In this study, we performed further studies to assess the apoptotic effects of γ-mangostin on colorectal adenocarcinoma cells HT29. γ-Mangostin showed concentration and time-dependent cytotoxic effects on HT29 cells. Microscopic observation under Giemsa staining showed that γ-mangostin induced cellular swelling and the appearance of apoptotic bodies, characteristic of apoptosis in HT29 cells. In addition, flow cytometry analysis showed an increase of hypodiploid cells in γ-mangostin-treated HT29 cells, while enhancement of intracellular peroxide production was detected in the same γ-mangostin-treated cells by DCHDA assay and DiOC6(3) staining. In view of the above results, γ-mangostin has demonstrated anticancer activity and induces apoptosis in HT29 colorectal adenocarcinoma cells. The evidence suggests that γ-mangostin could serve as a micronutrient for colon cancer prevention and is a potential lead compound for the development of anti-colon cancer agents.
Discovery of Gamma-Mangostin from Garcinia mangostana as a potent and selective natural SIRT2 inhibitor
Bioorg Chem 2020 Jan;94:103403.PMID:31711765DOI:10.1016/j.bioorg.2019.103403.
Studies have suggested that sirtuin inhibition may have beneficial effects on several age-related diseases such as neurodegenerative disorders and cancer. Garcinia mangostana is a well-known tropical plant found mostly in South East Asia with several positive health effects. Some of its phytochemicals such as α-mangostin was found to be able to modulate sirtuin activity in mice and was implicated with inflammation, diabetes and obesity. However, comprehensive studies on sirtuin activity by the prenylated xanthones extracted from Garcinia mangostana have yet to be reported. The present study led to the discovery and identification of γ-mangostin as a potent and selective SIRT2 inhibitor. It was demonstrated that γ-mangostin was able to increase the α-tubulin acetylation in MDA-MD-231 and MCF-7 breast cancer cells. It was also found to possess potent antiproliferative activity against both cell lines. In addition, it was able to induce neurite outgrowth in the N2a cells.
Gamma-Mangostin, a novel type of 5-hydroxytryptamine 2A receptor antagonist
Naunyn Schmiedebergs Arch Pharmacol 1998 Jan;357(1):25-31.PMID:9459569DOI:10.1007/pl00005134.
Gamma-Mangostin, purified from the fruit hull of the medicinal plant Garcinia mangostana caused a parallel rightwards shift of the concentration/response curve for the contraction elicited by 5-hydroxytryptamine (5-HT) in the rabbit aorta (pA2 = 8.2) without affecting the contractile responses to KCl, phenylephrine (alpha1) or histamine (H1). The perfusion pressure response of rat coronary artery to 5-HT (5-HT2A) was reduced concentration dependently by Gamma-Mangostin (IC50 = 0.32 microM). 5-HT amplified, ADP-induced aggregation of rabbit platelets (5-HT2A) was inhibited by Gamma-Mangostin (IC50 = 0.29 microM), whereas that induced by thrombin was not affected, nor did Gamma-Mangostin affect 5-HT-induced contraction of the guinea-pig ileum (5-HT3)in the presence of 5-HT1, 5-HT2 and 5-HT4 receptor antagonists. Furthermore, 5-HT-induced contraction of the rat fundus (5-HT2B) and 5-HT-induced relaxation of the rabbit aorta in the presence of ketanserin (5-HT1) and carbachol-induced contraction of the guinea-pig ileum (muscarinic M3) were not affected by Gamma-Mangostin (5 microM). Gamma-Mangostin inhibited [3H]spiperone binding to cultured rat aortic myocytes (IC50 = 3.5 nM). The Kd for [3H]spiperone binding was increased by Gamma-Mangostin (3 nM) from 11.7 to 27.4 nM without affecting Bmax. These results suggest that Gamma-Mangostin is a novel competitive antagonist, free from a nitrogen atom, for the 5-HT2A receptors in vascular smooth muscles and platelets.