Isogarcinol
(Synonyms: Cambogin) 目录号 : GC40901A natural benzophenone that has immunosuppressant actions
Cas No.:71117-97-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isogarcinol is a natural polyisoprenylated benzophenone first isolated from plant species in the genus Garcinia. It has immunosuppressant actions, inhibiting the protein phosphatase calcineurin (IC50 = 36 µM) and suppressing the proliferation of T cells. Oral administration of isogarcinol in mice decreases delayed type hypersensitivity, prolongs graft survival in allogeneic skin transplants, suppresses inflammation in collagen-induced arthritis, and reduces clinical symptoms in experimental autoimmune encephalomyelitis. Isogarcinol inhibits the proliferation of HL-60 and PC-3 cancer cells (IC50s = 4 and 8 µg/ml, respectively) through cell cycle arrest and apoptosis.
| Cas No. | 71117-97-0 | SDF | |
| 别名 | Cambogin | ||
| Canonical SMILES | CC([C@H](C/C=C(C)/C)C[C@]1(C[C@H](C/C=C(C)/C)C(C)(C)O2)C2=C3C(C4=CC(O)=C(O)C=C4)=O)(C)[C@](C/C=C(C)\C)(C1=O)C3=O | ||
| 分子式 | C38H50O6 | 分子量 | 602.8 |
| 溶解度 | DMF: 25 mg/ml,DMSO: 25 mg/ml,DMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml,Ethanol: 20 mg/ml | 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 | 1.6589 mL | 8.2946 mL | 16.5893 mL |
| 5 mM | 0.3318 mL | 1.6589 mL | 3.3179 mL |
| 10 mM | 0.1659 mL | 0.8295 mL | 1.6589 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。
Chemical and Biological Aspects of Garcinol and Isogarcinol: Recent Developments
Chem Biodivers 2019 Sep;16(9):e1900366.PMID:31386266DOI:10.1002/cbdv.201900366.
The natural polyisoprenylated benzophenone derivatives garcinol and Isogarcinol are secondary plant metabolites isolated from various Garcinia species including Garcinia indica. This review takes stock of the recent chemical and biological research into these interesting natural compounds over the last five years. New biological sources and chemical syntheses are discussed followed by new insights into the activity of garcinol and Isogarcinol against cancer, pathogenic bacteria, parasite infections and various inflammatory diseases.
(1S,5R,7R,30S)-14-De-oxy-isogarcinol
Acta Crystallogr Sect E Struct Rep Online 2012 Jun 1;68(Pt 6):o1861-2.PMID:22719626DOI:10.1107/S1600536812020788.
The title compound, C(38)H(50)O(5) {systematic name: 10-(3-hy-droxy-benzo-yl)-2,2,7,7-tetra-methyl-3,6,8-tris-(3-methyl-but-2-en-yl)-3,4,4a,5,6,7-hexa-hydro-4a,8-methano-2H-cyclo-octa-[b]pyran-9,11(8H)-dione}, is a polyisoprenylated benzophenone, isolated for the first time from the fruits of Garcinia indica during our investigation of bioactive compounds from this plant and their large-scale extraction. The relative configuration of the title compound was chosen based on comparison of its spectroscopic and optical rotation data with that of the isomorphous and isostructural compound Isogarcinol, whose absolute configuration is known. The crystal packing features O-H⋯O hydrogen bonds. A Cambridge Structural Database analysis revealed that the crystal structure reported here is isomorphous and isostructural with that of Isogarcinol.
The antioxidant activity and genotoxicity of Isogarcinol
Food Chem 2018 Jul 1;253:5-12.PMID:29502843DOI:10.1016/j.foodchem.2018.01.074.
The antioxidant activity and genotoxicity of Isogarcinol were assessed by several in vitro tests. Its IC50 values for DPPH and ABTS were 36.3 ± 3.35 µM and 16.6 ± 3.98 µM, respectively, which were all lower than those of VC and BHT. Isogarcinol had no cyctotoxic or promotional activities at 1-10 µM in the CCK-8 assay, and negligible genotoxic effects at 50-500 µM on HepG2 cells by the single-cell gel electrophoresis assay. Pre-incubation of the cells with 0.5-1.5 µM Isogarcinol, before exposure to H2O2, significantly increased cell viability in a concentration-dependent manner. Isogarcinol also reduced intercellular reactive oxygen species accumulation, lactate dehydrogenase release and malondialdehyde levels, and increased superoxide dismutase activity and glutathione levels. Western-blot analysis revealed that it up-regulated pro-caspase-3 and reduced cleaved caspase-3 during H2O2-induced oxidative stress. All the above results indicate that Isogarcinol promises to be useful as a natural antioxidant.
Isogarcinol is a new immunosuppressant
PLoS One 2013 Jun 13;8(6):e66503.PMID:23785505DOI:10.1371/journal.pone.0066503.
Calcineurin (CN), a unique protein phosphatase, plays an important role in immune regulation. In this study we used CN as a target enzyme to investigate the immunosuppressive properties of a series of natural compounds from Garcinia mangostana L., and discovered an active compound, Isogarcinol. Enzymatic assays showed that Isogarcinol inhibited CN in a dose-dependent manner. At concentrations resulting in relatively low cytotoxicity Isogarcinol significantly inhibited proliferation of murine spleen T-lymphocytes induced by concanavalin A (ConA) and the mixed lymphocyte reaction (MLR). In addition, it performed much better in acute toxicity tests and via oral administration in mice than cyclosporin A (CsA), with few adverse reactions and low toxicity in experimental animals. Oral administration of Isogarcinol in mice resulted in a dose-dependent decrease in delayed type hypersensitivity (DTH) and prolonged graft survival in allogeneic skin transplantation. These findings suggest that Isogarcinol could serve as a new oral immunomodulatory drug for preventing transplant rejection, and for long-term medication in autoimmune diseases.
Isogarcinol Extracted from Garcinia mangostana L. Ameliorates Systemic Lupus Erythematosus-like Disease in a Murine Model
J Agric Food Chem 2015 Sep 30;63(38):8452-9.PMID:26330173DOI:10.1021/acs.jafc.5b03425.
Isogarcinol is a new immunosuppressant that we extracted from Garcinia mangostana L. In the present study, we elucidate its beneficial effect in chronic graft-versus-host disease (cGVHD) in mice -- a model for systemic lupus erythematosus (SLE) in human. The oral administration of 60 mg/kg Isogarcinol significantly reduced proteinuria, corrected the abnormal serum biochemical indicator, and decreased the amount of serum antibodies and lowered the renal histopathology score. In addition, Isogarcinol alleviated the abnormal activation of CD4 T cells and decreased the expression of inflammatory genes and cytokines in the kidneys and peritoneal macrophages. The mechanism of action of Isogarcinol is associated with downregulation of CD4 T cells and inflammatory effects. Therefore, we believe that Isogarcinol may be a potential therapeutic drug candidate for future treatment of SLE.