ObacunoneCAS# 751-03-1 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 751-03-1 | SDF | Download SDF |
PubChem ID | 119041 | Appearance | White powder |
Formula | C26H30O7 | M.Wt | 454.5 |
Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
Synonyms | Obacunoic acid 3,4-lactone; Tricoccin S3 | ||
Solubility | DMSO : 250 mg/mL (550.04 mM; Need ultrasonic) | ||
SMILES | CC1(C2CC(=O)C3(C(C2(C=CC(=O)O1)C)CCC4(C35C(O5)C(=O)OC4C6=COC=C6)C)C)C | ||
Standard InChIKey | MAYJEFRPIKEYBL-OASIGRBWSA-N | ||
Standard InChI | InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1 | ||
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. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Obacunone is a novel activator of Nrf2, which exhibits anti-cancer, anti-inflammatory, antivirulence, insecticidal, anti-proliferative and anti-aromatase activities. Obacunone stimulates muscle hypertrophy and prevents obesity and hyperglycemia, and that these beneficial effects are likely to be mediated through the activation of TGR5 and inhibition of PPARγ transcriptional activity. Obacunone significantly inhibits aromatase activity in an in vitro enzyme assay with an IC50 value of 28.04 μM, and it also inhibits the p38 MAPK signaling pathway. |
Targets | Caspase | Akt | p38MAPK | PPAR | Nrf2 | P450 (e.g. CYP17) | Bcl-2/Bax | NF-kB | COX | Antifection | TGR5 |
In vitro | Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death.[Pubmed: 25592883]Toxicology. 2015 Mar 2;329:88-97.Obacunone and Obacunone glucoside (OG) are naturally occurring triterpenoids commonly found in citrus and other plants of the Rutaceae family.
The current study reports the mechanism of cytotoxicity of citrus-derived Obacunone and OG on human androgen-dependent prostate cancer LNCaP cells.
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In vivo | Obacunone represses Salmonella pathogenicity islands 1 and 2 in an envZ-dependent fashion.[Pubmed: 22843534]Appl Environ Microbiol. 2012 Oct;78(19):7012-22.Obacunone belongs to a class of unique triterpenoids called limonoids, present in Citrus species. Previous studies from our laboratory suggested that Obacunone possesses antivirulence activity and demonstrates inhibition of cell-cell signaling in Vibrio harveyi and Escherichia coli O157:H7.
Dietary obacunone supplementation stimulates muscle hypertrophy, and suppresses hyperglycemia and obesity through the TGR5 and PPARγ pathway.[Pubmed: 26051277 ]Biochem Biophys Res Commun. 2015 Aug 7;463(4):846-52.Obacunone is a limonoid that is predominantly found in Citrus. Although various biological activities of limonoids have been reported, little is known about the beneficial effects of Obacunone on metabolic disorders. In the present study, we examined the effects of dietary Obacunone supplementation on obese KKAy mice, to clarify the function of Obacunone in metabolic regulation.
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Kinase Assay | Obacunone activates the Nrf2-dependent antioxidant responses.[Reference: WebLink]Protein Cell. 2016 Sep;7(9):684-8.The transcription factor nuclear factor erythroid 2-relatedfactor 2 (Nrf2) plays a crucial role in human antioxidantdefense response against environmental insults.
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Cell Research | Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells.[Pubmed: 24927687]Biochimie. 2014 Oct;105:36-44.Overexpression of the aromatase enzyme CYP19 has been implicated in the onset of estrogen-dependent breast carcinogenesis. Obacunone, a natural compound present in citrus fruits, has been demonstrated for various biological activities including anti-cancer and anti-inflammatory properties.
|
Animal Research | Insight into reduction of obacunone, and their ester derivatives as insecticidal agents against Mythimna separata Walker.[Pubmed: 25465171]Bioorg Med Chem Lett. 2015 Jan 1;25(1):25-9.Here we have prepared a series of ester compounds of Obacunone, a naturally occurring limonoid, isolated from plants such as Citrus and Dictamnus angustifolius.
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Obacunone Dilution Calculator
Obacunone Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.2002 mL | 11.0011 mL | 22.0022 mL | 44.0044 mL | 55.0055 mL |
5 mM | 0.44 mL | 2.2002 mL | 4.4004 mL | 8.8009 mL | 11.0011 mL |
10 mM | 0.22 mL | 1.1001 mL | 2.2002 mL | 4.4004 mL | 5.5006 mL |
50 mM | 0.044 mL | 0.22 mL | 0.44 mL | 0.8801 mL | 1.1001 mL |
100 mM | 0.022 mL | 0.11 mL | 0.22 mL | 0.44 mL | 0.5501 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells.[Pubmed:24927687]
Biochimie. 2014 Oct;105:36-44.
Overexpression of the aromatase enzyme CYP19 has been implicated in the onset of estrogen-dependent breast carcinogenesis. Obacunone, a natural compound present in citrus fruits, has been demonstrated for various biological activities including anti-cancer and anti-inflammatory properties. In the present study, we have isolated Obacunone and Obacunone glucoside (OG) from lemon seeds, then fractionated these compounds using chromatographic techniques and characterized them by HPLC, LC-MS, and 2D NMR spectral analysis. To investigate the mechanism of anti-cancer and anti-aromatase activities of limonoids, their cytotoxic effect was tested on human breast cancer (MCF-7) and non-malignant (MCF-12F) breast cells. MTT assays confirmed that Obacunone was strongly inhibited MCF-7 cell proliferation without affecting non-malignant breast cells. Treatment with Obacunone increased apoptosis by up-regulating expression of the pro-apoptotic protein Bax and down-regulating the anti-apoptotic protein Bcl2, as well as inducing G1 cell cycle arrest. In addition, Obacunone significantly inhibited aromatase activity in an in vitro enzyme assay. Exposure of MCF-7 breast cancer cells to Obacunone down-regulated expression of inflammatory molecules including nuclear factor-kappa B (NF-kappaB) and cyclooxygenase-2 (COX-2). Furthermore, we found that Obacunone inhibited COX-2 and NF-kappaB by activation of the p38 mitogen-activated protein kinase (MAPK). Finally, the uptake level of Obacunone into MCF-7 cells was measured by HPLC and its structure was confirmed by LC-HR-MS. This study demonstrated that Obacunone may have the potential to prevent estrogen-responsive breast cancer through inhibition of the aromatase enzyme and inflammatory pathways, as well as activation of apoptosis.
Obacunone represses Salmonella pathogenicity islands 1 and 2 in an envZ-dependent fashion.[Pubmed:22843534]
Appl Environ Microbiol. 2012 Oct;78(19):7012-22.
Obacunone belongs to a class of unique triterpenoids called limonoids, present in Citrus species. Previous studies from our laboratory suggested that Obacunone possesses antivirulence activity and demonstrates inhibition of cell-cell signaling in Vibrio harveyi and Escherichia coli O157:H7. The present work sought to determine the effect of Obacunone on the food-borne pathogen Salmonella enterica serovar Typhimurium LT2 by using a cDNA microarray. Transcriptomic studies indicated that Obacunone represses Salmonella pathogenicity island 1 (SPI1), the maltose transporter, and the hydrogenase operon. Furthermore, phenotypic data for the Caco-2 infection assay and maltose utilization were in agreement with microarray data suggesting repression of SPI1 and maltose transport. Further studies demonstrated that repression of SPI1 was plausibly mediated through hilA. Additionally, Obacunone seems to repress SPI2 under SPI2-inducing conditions as well as in Caco-2 infection models. Furthermore, Obacunone seems to repress hilA in an EnvZ-dependent fashion. Altogether, the results of the study seems to suggest that Obacunone exerts an antivirulence effect on S. Typhimurium and may serve as a lead compound for development of antivirulence strategies for S. Typhimurium.
Dietary obacunone supplementation stimulates muscle hypertrophy, and suppresses hyperglycemia and obesity through the TGR5 and PPARgamma pathway.[Pubmed:26051277]
Biochem Biophys Res Commun. 2015 Aug 7;463(4):846-52.
Obacunone is a limonoid that is predominantly found in Citrus. Although various biological activities of limonoids have been reported, little is known about the beneficial effects of Obacunone on metabolic disorders. In the present study, we examined the effects of dietary Obacunone supplementation on obese KKAy mice, to clarify the function of Obacunone in metabolic regulation. Mice were pair-fed a normal diet either alone or supplemented with 0.1% w/w Obacunone for 28 days. Compared with the control, Obacunone-fed mice had lower glycosylated hemoglobin, blood glucose, and white adipose tissue weight, although there was no significant difference in body weight. Obacunone treatment also significantly increased the weight of the gastrocnemius and quadriceps muscles. Reporter gene assays revealed that Obacunone stimulated the transcriptional activity of the bile acids-specific G protein-coupled receptor, TGR5, in a dose-dependent manner. In addition, Obacunone inhibited adipocyte differentiation in 3T3-L1 cells and antagonized ligand-stimulated peroxisome proliferator-activated receptor gamma (PPARgamma) transcriptional activity. These results suggest that Obacunone stimulates muscle hypertrophy and prevents obesity and hyperglycemia, and that these beneficial effects are likely to be mediated through the activation of TGR5 and inhibition of PPARgamma transcriptional activity.
Insight into reduction of obacunone, and their ester derivatives as insecticidal agents against Mythimna separata Walker.[Pubmed:25465171]
Bioorg Med Chem Lett. 2015 Jan 1;25(1):25-9.
Here we have prepared a series of ester compounds of Obacunone, a naturally occurring limonoid, isolated from plants such as Citrus and Dictamnus angustifolius. Their insecticidal activity was evaluated at 1 mg/mL against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker), a typical lepidopteran pest. When Obacunone reacted with NaBH(4), the ratio of two reduction products, C7alpha-hydroxyObacunone (2) and C7beta-hydroxyObacunone (3), was related to the reaction mixing solvents. C7alpha-Propionyloxybacunone (4b) and C7beta-(n)heptanoyloxybacunone (5g) exhibited the more promising insecticidal activity than their precursor Obacunone and toosendanin.
Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death.[Pubmed:25592883]
Toxicology. 2015 Mar 2;329:88-97.
Obacunone and Obacunone glucoside (OG) are naturally occurring triterpenoids commonly found in citrus and other plants of the Rutaceae family. The current study reports the mechanism of cytotoxicity of citrus-derived Obacunone and OG on human androgen-dependent prostate cancer LNCaP cells. Both limonoids exhibited time- and dose-dependent inhibition of cell proliferation, with more than 60% inhibition of cell viability at 100 muM, after 24 and 48 h. Analysis of fragmentation of DNA, activity of caspase-3, and cytosolic cytochrome-c in the cells treated with limonoids provided evidence for activation of programmed cell death by limonoids. Treatment of LNCaP cells with Obacunone and OG resulted in dose-dependent changes in expression of proteins responsible for the induction of programmed cell death through the intrinsic pathway and down-regulation of Akt, a key molecule in cell signaling pathways. In addition, Obacunone and OG also negatively regulated an inflammation-associated transcription factor, androgen receptor, and prostate-specific antigen, and activated proteins related to the cell cycle, confirming the ability of limonoids to induce cytotoxicity through multiple pathways. The results of this study provided, for the first time, an evidence of the cytotoxicity of Obacunone and OG in androgen-dependent human prostate cancer cells.