Gartanin
(Synonyms: 1,3,5,8-四羟基-2,4-双(3-甲基-2-丁烯基)-9H-氧杂蒽-9-酮) 目录号 : GC38087
A prenylated xanthone with anticancer activity
Cas No.:33390-42-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Gartanin is a prenylated xanthone that has been found in G. mangostana and has anticancer activity.1,2 It inhibits the growth of T24, UM-UC-3, HT-1376, and TCCSUP bladder cancer cells (IC50s = 4.1-18.1 ?M).1 Gartanin (10 and 50 ?M) increases the number of LC3 puncta, a marker of autophagy, in T24 cells expressing pEGFP-LC3, as well as induces apoptosis in T24 and RT4 cells. It binds to NEDD8-activating enzyme (NAE) and inhibits NEDDylation of cullin 1 and ubiquitin-conjugating enzyme 12 (UBC12) in PC3 and 22Rv1 prostate cancer cells.2
1.Liu, Z., Antalek, M., Nguyen, L., et al.The effect of gartanin, a naturally occurring xanthone in mangosteen juice, on the mTOR pathway, autophagy, apoptosis, and the growth of human urinary bladder cancer cell linesNutr. Cancer65 Suppl. 1 (0 1)68-77(2013) 2.Pham, V., Rendon, R., Le, V.X., et al.Gartanin is a novel NEDDylation inhibitor for induction of Skp2 degradation, FBXW2 expression, and autophagyMol. Carcinog.59(2)193-201(2020)
| Cas No. | 33390-42-0 | SDF | |
| 别名 | 1,3,5,8-四羟基-2,4-双(3-甲基-2-丁烯基)-9H-氧杂蒽-9-酮 | ||
| Canonical SMILES | O=C1C2=C(OC3=C(O)C=CC(O)=C13)C(C/C=C(C)\C)=C(O)C(C/C=C(C)/C)=C2O | ||
| 分子式 | C23H24O6 | 分子量 | 396.43 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C,protect from light |
| 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。
Metabolism of Gartanin in liver microsomes and its modulating effects on cytochrome P450s
Xenobiotica 2022 Apr;52(4):335-345.PMID:35607983DOI:10.1080/00498254.2022.2076631.
Gartanin, a compound found in mangosteen, has various pharmacological activities, including anticancer, anti-inflammation, and antioxidation.In the present study, we reported differences of Gartanin metabolism among species and the effect of Gartanin on cytochrome P450 (CYP) activities and protein expression.We found significant difference in Gartanin metabolism among species, where rabbits and humans had similar metabolic characteristics. Five CYP-catalysed metabolites and three glucuronosyltransferase (UGT)-catalysed metabolites were identified by LC-MS/MS. Hydroxylation was the major metabolic pathway. Gartanin exhibited mixed inhibition on CYP1A2 activity with IC50 and Ki values of 1.48 and 3.71 μM, respectively. In addition, Gartanin down-regulated the protein expressions of CYP2C9 and CYP2D6 and up-regulated the protein expression of CYP2D6. The present study supports the pharmacological and toxicological research of Gartanin.
Gartanin is a novel NEDDylation inhibitor for induction of Skp2 degradation, FBXW2 expression, and autophagy
Mol Carcinog 2020 Feb;59(2):193-201.PMID:31782573DOI:10.1002/mc.23140.
Gartanin, a 4-prenylated xanthone, has been identified from the purple mangosteen fruit as a potent growth inhibitor of various cancer cell lines, including prostate cancer. However, much of Gartanin's anticancer mechanism remains unknown. We have discovered that Gartanin docked onto the regulatory subunit of the precursor cell-expressed developmentally downregulated 8 (NEDD8)-activating enzyme (NAE) complex and next to the NEDD8 binding complex, which leads to inhibit NEDD8 conjugations to both Cullin1 and Ubc12 in prostate cancer cell lines and Ubc12 NEDDylation in an in vitro assay. The S phase kinase-associated protein (Skp2) and F-box and WD-repeat domain-containing 2 (FBXW2), the NEDD8 family members of E3 ubiqutin ligases, were also downregulated and upregulated by Gartainin, respectively. Knock-down of NEDD8 expression by short harpin (Sh) RNAs blocked or attenuated these effects of Gartainin. Finally, Gartanin demonstrated its ability to inhibit growth of prostate cancer lines via autophagy initiation. Our data support that Gartanin is a naturally occurring NEDDylation inhibitor and deserves further investigation for prostate cancer prevention and treatment.
Gartanin induces autophagy through JNK activation which extenuates caspase-dependent apoptosis
Oncol Rep 2015 Jul;34(1):139-46.PMID:25955534DOI:10.3892/or.2015.3948.
Hepatocellular carcinoma (HCC) is the third leading cause of cancer-related death worldwide. Development of novel agents to eradicate liver cancer cells is required for treatment of HCC. Gartanin, a xanthone-type compound isolated from mangosteen, is known to possess potent antioxidant, anti-inflammatory, antifungal and antineoplastic properties. In the present study, we investigated the cytotoxic effect of Gartanin on HCC and explored the cell death mechanism. We showed that Gartanin induced both the extrinsic and intrinsic apoptotic pathways, which were interconnected by caspase-8, -9 and -3 activation. We also provided convincing evidence that Gartanin induced autophagy in various cancer cells, as demonstrated by acridine orange staining of intracellular acidic vesicles, the degradation of p62, the conversion of LC3-I to LC3-II and GFP-LC3 punctate fluorescence. Additionally, Gartanin induced the formation of typical autophagosomes and autolysosomes and enhanced the degradation rate of intracellular granule(s), including mitochondria. Notably, gartanin-mediated apoptotic cell death was further potentiated by pretreatment with autophagy inhibitors (3-methyladenine and bafilomycin A1) or small interfering RNAs against the autophagic genes (Atg5). These findings suggested that gartanin-mediated autophagic response protected against eventual cell death induced by Gartanin. Moreover, Gartanin treatment led to phosphorylation/activation of JNK and JNK-dependent phosphorylation of Bcl-2. Importantly, JNK inhibitor (SP600125) inhibited autophagy yet promoted gartanin-induced apoptosis, indicating a key requirement of the JNK-Bcl-2 pathway in the activation of autophagy by Gartanin. Taken together, our data suggested that the JNK-Bcl-2 pathway was the critical regulator of gartanin-induced protective autophagy and a potential drug target for chemotherapeutic combination.
Gartanin Compounds from Extract Ethanol Pericarp Mangosteen ( Garcinia mangostana Linn.)
Open Access Maced J Med Sci 2019 Nov 14;7(22):3891-3895.PMID:32127999DOI:10.3889/oamjms.2019.527.
Aim: The study aimed to isolate and identification secondary metabolite from pericarp Garcinia mangostana Linn. Methods: The first step of this research was maceration of sample using alcohol 70% solvent. The separation and purification of compounds using Vacuum Liquid Chromatography (VLC), Radial Chromatography (RC). The purity of isolate was analyzed by thin layer chromatography (TLC) and melting point. Compounds identified using spectroscopi IR, NMR-1D (1H, 13C-NMR and DEPT) and 2-D NMR (HMQC and HMBC). Results: The compound has melting point at 165-167°C. The result showed isolate was Gartanin. Conclusion: The secondary metabolite found in pericarp Garcinia mangostana Linn. is Gartanin.
Gartanin, an isoprenylated xanthone from the mangosteen fruit (Garcinia mangostana), is an androgen receptor degradation enhancer
Mol Nutr Food Res 2016 Jun;60(6):1458-69.PMID:27019217DOI:10.1002/mnfr.201600037.
Scope: Androgen receptor (AR) has been a target of prostate cancer for nearly seven decades. In the last several years there has been an interest in identifying compounds that promote degradation of the androgen receptor. In the present study, Gartanin, an isoprentylated xanthone in the mangosteen fruit, was evaluated for enhancing AR degradation, and inducing the unfolded protein response pathway. Methods and results: The interaction of Gartanin with the ligand-binding domain was characterized using a fluorescence polarization cell-free assay and cell-based FRET assay. Western blot analysis identified modulation of ER stress markers (BiP, PERK, IRE1, and CHOP) along with androgen receptor degradation. A computation simulation was performed to identify possible orientations of Gartanin with the ligand-binding domain. Utilizing a cell-free and cell-based FRET assays Gartanin was found to interact with the ligand-binding domain through a solely antagonist interaction. Interestingly, inhibition of CHOP, a critical component of the ER stress pathway, was observed to stabilize AR. Conclusions: Gartanin is an isoprenylated xanthone that promotes AR degradation with evidence suggesting this process is critically regulated by the unfolded protein response pathway.