Beta-SitosterolCAS# 83-46-5 |
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| Cas No. | 83-46-5 | SDF | Download SDF |
| PubChem ID | 222284 | Appearance | White powder |
| Formula | C29H50O | M.Wt | 414.69 |
| Type of Compound | Steroids | Storage | Desiccate at -20°C |
| Synonyms | β-Sitosterol; 22,23-Dihydrostigmasterol | ||
| Solubility | DMSO : < 1 mg/mL (insoluble or slightly soluble) Ethanol : 3.85 mg/mL (9.28 mM; Need ultrasonic) | ||
| Chemical Name | (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | ||
| SMILES | CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C | ||
| Standard InChIKey | KZJWDPNRJALLNS-VJSFXXLFSA-N | ||
| Standard InChI | InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/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 | Beta-Sitosterol is a novel plant-derived angiogenic factor which may have potential pharmaceutical applications for the management of chronic wounds. It has potent anti-inflammatory, anti-proliferation, and pro- apoptosis activities, it also possesses antipyretic activity, similar to acetylsalicylic acid. |
| Targets | PARP | Bcl-2/Bax | Caspase | IAP |
| In vitro | Beta-sitosterol induces anti-proliferation and apoptosis in human leukemic U937 cells through activation of caspase-3 and induction of Bax/Bcl-2 ratio.[Pubmed: 17603173]Biol Pharm Bull. 2007 Jul;30(7):1317-23.Beta-Sitosterol is the main dietary phytosterol found in plants and has been shown to inhibit proliferation and induce apoptosis in human solid tumors such as colon and breast cancers. However, the mechanism by which Beta-Sitosterol induces apoptosis is not completely understood in leukemic cells.
A novel angiogenic factor derived from Aloe vera gel: beta-sitosterol, a plant sterol.[Pubmed: 14517429]Angiogenesis. 1999;3(2):117-23.Aloe vera gel has a beneficial effect on wound healing. Because angiogenesis is an essential process in wound healing, we hypothesized that Aloe vera gel might contain potent angiogenic compounds.
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| In vivo | Anti-inflammatory and antipyretic activities of beta-sitosterol[Reference: WebLink]Planta Med. 1980 Jun;39(2):157-63.
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| Cell Research | Induction of Bax and activation of caspases during beta-sitosterol-mediated apoptosis in human colon cancer cells.[Pubmed: 14612938]Int J Oncol. 2003 Dec;23(6):1657-62.Beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer.
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Beta-Sitosterol Dilution Calculator
Beta-Sitosterol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4114 mL | 12.0572 mL | 24.1144 mL | 48.2288 mL | 60.286 mL |
| 5 mM | 0.4823 mL | 2.4114 mL | 4.8229 mL | 9.6458 mL | 12.0572 mL |
| 10 mM | 0.2411 mL | 1.2057 mL | 2.4114 mL | 4.8229 mL | 6.0286 mL |
| 50 mM | 0.0482 mL | 0.2411 mL | 0.4823 mL | 0.9646 mL | 1.2057 mL |
| 100 mM | 0.0241 mL | 0.1206 mL | 0.2411 mL | 0.4823 mL | 0.6029 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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Beta-Sitosterol weakly inhibits porcine pancreatic lipase (PPL) activity. Sitosterol is an important compound extracted from the leaves of Aloe vera.
In Vitro:Bioactivity-guided isolation afforded three compounds from the hexane fraction of E. indica, namely, Beta-Sitosterol (β-sitosterol), Stigmasterol, and Lutein. Both compounds are found to possess very low PPL inhibition activity, that is, 2.99±0.80% (Beta-Sitosterol) of inhibition at 100 μg/mL (242 μM) and 2.68±0.38% (Stigmasterol) of inhibition at 100 μg/mL (243 μM), respectively. Weak PPL inhibition activity of Beta-Sitosterol and Stigmasterol isolated from Alpinia zerumbet with IC50 value of 99.99±1.86 μg/mL and 125.05±4.76 μg/mL, respectively, in comparison with the inhibition shown by Curcumin (IC50=4.92±0.21 μg/mL) and Quercetin (IC50=18.60±0.86 μg/mL) which are used as positive controls in their study. Beta-Sitosterol and Stigmasterol are recorded with weak PPL inhibitory activity of only 3.0±0.8% and 2.7±0.4% at 100 μg/mL, respectively, (i.e., 242 μM and 243 μM) in contrast (34.5±5.4% at 100 μg/mL), which are comparatively lower than that recorded in literature (i.e., 50% PPL inhibition at 100 μg/mL)[1]. Sitosterol is an important compound extracted from the leaves of Aloe vera. It inhibits the growth of promastigotes of L. donovani, a causative agent for life threatening visceral leishmaniasis disease[2].
In Vivo:Beta-Sitosterol (β-sitosterol) treatment significantly reduced the immobility time at three doses (10, 20, and 30 mg/kg) in the Forced Swim Test (FST) and Tail Suspension Test (TST), indicating an antidepressant effect. This effect is similar to the positive control fluoxetine (20 mg/kg) at a dose of 30 mg/kg, where the strongest effect is observed compared with the control group (P < 0.001). The same effects are observed for three doses of Beta-Sitosterol in the TST. The % DID values are as follows: FST: 39.27% (10 mg/kg), 51.23% (20 mg/kg), and 57.48% (30 mg/kg); TST: 31.63% (10 mg/kg), 43.95% (20 mg/kg), and 53.38% (30 mg/kg). These results indicate that Beta-Sitosterol has a significant antidepressant activity in mice during the FST and TST. Furthermore, Beta-Sitosterol exhibits the antidepressant effect in a dose-dependent manner[3].
References:
[1]. Ong SL, et al. Porcine Pancreatic Lipase Inhibitory Agent Isolated from Medicinal Herb and Inhibition Kinetics of Extracts from Eleusine indica (L.) Gaertner. J Pharm (Cairo). 2016;2016:8764274.
[2]. Tariq A, et al. Ethnomedicines and anti-parasitic activities of Pakistani medicinal plants against Plasmodia and Leishmania parasites. Ann Clin Microbiol Antimicrob. 2016 Sep 20;15(1):52.
[3]. Zhao D, et al. Structural Features and Potent Antidepressant Effects of Total Sterols and β-sitosterol Extracted from Sargassum horneri. Mar Drugs. 2016 Jun 28;14(7).
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Induction of Bax and activation of caspases during beta-sitosterol-mediated apoptosis in human colon cancer cells.[Pubmed:14612938]
Int J Oncol. 2003 Dec;23(6):1657-62.
Beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. The purpose of the present study was to examine the effect of Beta-Sitosterol on the growth of HT116 human colon cancer cells. Treatment with Beta-Sitosterol resulted in a dose-dependent growth inhibition coupled with the characteristic morphological features of apoptosis and with the increase of a sub-G1 cell population. Apoptosis-inducing concentrations of Beta-Sitosterol induced caspase-3 and caspase-9 activation accompanied by proteolytic cleavage of poly(ADP-ribose)-polymerase. In addition, Beta-Sitosterol-induced apoptosis in HT116 cells was associated with a decreased expression of the anti-apototic Bcl-2 protein and mRNA and a concomitant increase of the pro-apototic Bax protein and mRNA, and with release of cytochrome c from the mitochondria into the cytosol. Beta-Sitosterol treatment also inhibited the expression of cIAP-1 without significant changes in the level of cIAP-2. Taken together, these findings provide important new insights into the possible molecular mechanisms of the anti-cancer activity of Beta-Sitosterol.
Beta-sitosterol induces anti-proliferation and apoptosis in human leukemic U937 cells through activation of caspase-3 and induction of Bax/Bcl-2 ratio.[Pubmed:17603173]
Biol Pharm Bull. 2007 Jul;30(7):1317-23.
Beta-Sitosterol is the main dietary phytosterol found in plants and has been shown to inhibit proliferation and induce apoptosis in human solid tumors such as colon and breast cancers. However, the mechanism by which Beta-Sitosterol induces apoptosis is not completely understood in leukemic cells. This study investigated the mechanism of apoptosis induced by Beta-Sitosterol in human leukemic U937 cells. Beta-Sitosterol induced cytotoxicity and apoptosis in U937 cells in a concentration dependent manner, as measured by hemocytometer counts, fluorescence microscopy, agarose gel electrophoresis, and flow cytometry analysis. The increase in apoptosis induced by Beta-Sitosterol was associated with down-regulation of Bcl-2, degradation of poly-(ADP-ribose) polymerase (PARP) and phospholipase C (PLC)-gamma1 protein, and activation of caspase-3. Beta-Sitosterol induced apoptosis was not associated with changes in the expression of Bcl-xL, Bax, or inhibitor of apoptosis proteins (IAPs). z-DEVD-fmk, a caspase-3 specific inhibitor, blocked caspase-3 activation and PARP degradation, and significantly attenuated Beta-Sitosterol-induced apoptosis. This suggests that caspase-3 activation is partially essential for Beta-Sitosterol-induced apoptosis. Bcl-2 overexpression also significantly blocked caspase-3 activation and the decrease in PARP cleavage by Beta-Sitosterol, and effectively attenuated the apoptotic response to Beta-Sitosterol. These results show that Beta-Sitosterol potently induces apoptosis in U937 cells and that Beta-Sitosterol-induced apoptosis is related to the selective activation of caspase-3 and induction of Bax/Bcl-2 ratio.
A novel angiogenic factor derived from Aloe vera gel: beta-sitosterol, a plant sterol.[Pubmed:14517429]
Angiogenesis. 1999;3(2):117-23.
Aloe vera gel has a beneficial effect on wound healing. Because angiogenesis is an essential process in wound healing, we hypothesized that Aloe vera gel might contain potent angiogenic compounds. Here we demonstrate that Aloe vera gel and its extracts are angiogenic on the chorioallantoic membrane (CAM) of chick embryo. Out of the three compounds purified from the final fraction of Aloe vera gel, Beta-Sitosterol showed a potent angiogenic activity in the CAM assay. In the presence of heparin, Beta-Sitosterol stimulated neovascularization in the mouse Matrigel plug assay and the motility of human umbilical vein endothelial cells in an in vitro wound migration assay. Thus Beta-Sitosterol is a novel plant-derived angiogenic factor which may have potential pharmaceutical applications for the management of chronic wounds.
