Isogarcinol |
| Catalog No.: GC40901 |
Isogarcinol is a natural polyisoprenylated benzophenone first isolated from plant species in the genus Garcinia.
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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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 | |
| 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 | ||
| Formula | C38H50O6 | M.Wt | 602.8 |
| Solubility | DMF: 25 mg/ml,DMSO: 25 mg/ml,DMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml,Ethanol: 20 mg/ml | Storage | Store at -20°C, protect from light |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
| Shipping Condition | Evaluation sample solution : ship with blue ice All other available size: ship with RT , or blue ice upon request |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
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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.
Average Rating: 5 (Based on Reviews and 26 reference(s) in Google Scholar.)
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