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    Stigmasterol
    Information
    CAS No. 83-48-7 Price $30 / 20mg
    Catalog No.CFN97326Purity>=98%
    Molecular Weight412.7 Type of CompoundSteroids
    FormulaC29H48OPhysical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Stigmasterol is used as a precursor in the manufacture of synthetic progesterone, it is an antagonist of the bile acid nuclear receptor FXR, which has anti-inflammatory, thyroid inhibitory, cholesterol-lowering, antiperoxidative and hypoglycemic effects; it has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate, breast, and colon cancers. Stigmasterol inhibits the NF-kappaB pathway.
    Targets: IL Receptor | MMP(e.g.TIMP) | PGE | NF-kB | Bcl-2/Bax | Caspase | p53 | ERK | cAMP | NMDAR | SOD
    In vitro:
    Osteoarthritis Cartilage. 2010 Jan;18(1):106-16.
    Stigmasterol: a phytosterol with potential anti-osteoarthritic properties.[Pubmed: 19786147]
    Although most studies have focused on the cholesterol-lowering activity of Stigmasterol, other bioactivities have been ascribed to this plant sterol compound, one of which is a potential anti-inflammatory effect. To investigate the effects of Stigmasterol, a plant sterol, on the inflammatory mediators and metalloproteinases produced by chondrocytes.
    METHODS AND RESULTS:
    We used a model of newborn mouse chondrocytes and human osteoarthritis (OA) chondrocytes in primary culture stimulated with or without IL-1beta (10 ng/ml), for 18 h. Cells were pre-incubated for 48 h with Stigmasterol (20 microg/ml) compared to untreated cells. We initially investigated the presence of Stigmasterol in chondrocyte, compared to other phytosterols. We then assessed the role of Stigmasterol on the expression of various genes involved in inflammation (IL-6) and cartilage turn-over (MMP-3, -13, ADAMTS-4, -5, type II collagen, aggrecan) by quantitative Reverse Transcriptase-Polymerase Chain Reaction (RT-PCR). Additional experiments were carried out to monitor the production of MMP-3 and prostaglandin E2 (PGE(2)) by specific immuno-enzymatic assays. We eventually looked at the role of Stigmasterol on NF-kappaB activation by western blot, using an anti-IkappaBalpha antibody. After 18 h of IL-1beta treatment, MMP-3, MMP-13, ADAMTS-4, but not ADAMTS-5 RNA expression were elevated, as well as MMP-3 and PGE(2) protein levels in mouse and human chondrocytes. Type II collagen and aggrecan mRNA levels were significatively reduced. Pre-incubation of Stigmasterol to IL-1beta-treated cells significantly decreased these effects described above (significant reduction of MMP-3 mRNA in human and mouse, MMP-3 protein in mouse, MMP-13 mRNA in mouse and human, ADAMTS-4 mRNA in human, PGE(2) protein in human and mouse) Finally, Stigmasterol was capable of counteracting the IL-1beta-induced NF-kappaB pathway.
    CONCLUSIONS:
    This study shows that Stigmasterol inhibits several pro-inflammatory and matrix degradation mediators typically involved in OA-induced cartilage degradation, at least in part through the inhibition of the NF-kappaB pathway. These promising results justify further ex vivo and in vivo investigations with Stigmasterol.
    In vivo:
    Eur J Pharmacol. 2012 Feb 15;676(1-3):64-70.
    The ameliorating effects of stigmasterol on scopolamine-induced memory impairments in mice.[Pubmed: 22173129]
    Stigmasterol, a kind of phytosterol, is present in small amounts in various foods.
    METHODS AND RESULTS:
    In the present study, we investigated the effects of Stigmasterol on scopolamine-induced memory impairments using the passive avoidance and the Morris water maze tasks in mice. In addition, changes in memory-related molecules, including extracellular signal-regulated kinase (ERK) and cAMP response element-binding protein (CREB), were examined following the administration of Stigmasterol. Scopolamine-induced memory impairments were significantly attenuated by the administration of Stigmasterol (10mg/kg) in the passive avoidance task. In the Morris water maze task, the escape latencies were significantly decreased in the Stigmasterol-treated group compared to the scopolamine-treated group during the training phase. The swimming times within the target zone during the probe trial were significantly increased as compared to scopolamine-treated mice. Furthermore, the ameliorating effect of Stigmasterol on scopolamine-induced memory dysfunction was blocked by a sub-effective dose of dizocilpine (MK-801), an NMDA receptor antagonist, and tamoxifen, an estrogen receptor antagonist, in the passive avoidance task. In addition, the expression levels of phosphorylated ERK and CREB in the hippocampus were significantly increased by Stigmasterol, which was blocked by tamoxifen or MK-801 with scopolamine.
    CONCLUSIONS:
    These results suggest that Stigmasterol-induced cognitive ameliorative effects are mediated by the enhancement of cholinergic neurotransmission system via the activation of estrogen or NMDA receptors.
    Metabolism. 2006 Mar;55(3):292-9.
    Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat.[Pubmed: 16483871]
    Plant sterols compete with cholesterol (cholest-5-en-3beta-ol) for intestinal absorption to limit absorption and lower plasma concentrations of cholesterol. Stigmasterol (24-ethyl-cholesta-5,22-dien-3beta-ol; Delta(22) derivative of sitosterol [24-ethyl-cholest-5-en-3beta-ol]), but not campesterol (24-methyl-cholest-5-en-3beta-ol) and sitosterol, is reported to inhibit cholesterol biosynthesis via inhibition of sterol Delta(24)-reductase in human Caco-2 and HL-60 cell lines.
    METHODS AND RESULTS:
    We studied the effect of feeding 0.5% Stigmasterol on plasma and liver sterols and intestinal cholesterol and sitosterol absorption in 12 wild-type Kyoto (WKY) and 12 Wistar rats. After 3 weeks of feeding, cholesterol and sitosterol absorption was determined in 6 rats from each group by plasma dual-isotope ratio method. After 3 more weeks, plasma and hepatic sterols and hepatic enzyme activities were determined in all rats. After feeding Stigmasterol, baseline plasma cholesterol was 1.3 times and plant sterols 3 times greater in WKY compared with Wistar rats. Stigmasterol feeding lowered plasma cholesterol by approximately 11%, whereas plasma campesterol and sitosterol levels were virtually unchanged in both rat strains, and Stigmasterol constituted 3.2% of plasma sterols in WKY rats and 1% in Wistar rats. After 6 weeks of feeding, cholesterol and sitosterol absorption decreased 23% and 30%, respectively, in WKY, and 22% and 16%, respectively, in the Wistar rats as compared with untreated rats. The intestinal bacteria in both rat strains metabolized Stigmasterol to mainly the 5beta-H stanol (>40%), with only small amounts of 5alpha-H derivative (approximately 1.5%), whereas the C-22 double bond was resistant to bacterial metabolism. Hepatic Stigmasterol levels increased from 11 microg/g liver tissue to 104 mug/g in WKY rats and from 5 microg/g liver tissue to 21 microg/g in Wistar rats. 3-Hydroxy-3-methylglutaryl coenzyme A reductase activity was suppressed 4-fold in the WKY and almost 1.8-fold in Wistar rats, cholesterol 7alpha-hydroxylase activity was suppressed 1.6-fold in the WKY and 3.5-fold in Wistar rats, whereas cholesterol 27-hydroxylase activity was unchanged after feeding.
    CONCLUSIONS:
    In conclusion, Stigmasterol, when fed, lowers plasma cholesterol levels, inhibits intestinal cholesterol and plant sterol absorption, and suppresses hepatic cholesterol and classic bile acid synthesis in Wistar as well as WKY rats. However, plasma and hepatic incorporation of Stigmasterol is low.
    Stigmasterol Description
    Source: The herbs of Delphinium grandiflorum L.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.4231 mL 12.1153 mL 24.2307 mL 48.4614 mL 60.5767 mL
    5 mM 0.4846 mL 2.4231 mL 4.8461 mL 9.6923 mL 12.1153 mL
    10 mM 0.2423 mL 1.2115 mL 2.4231 mL 4.8461 mL 6.0577 mL
    50 mM 0.0485 mL 0.2423 mL 0.4846 mL 0.9692 mL 1.2115 mL
    100 mM 0.0242 mL 0.1212 mL 0.2423 mL 0.4846 mL 0.6058 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Cell Research:
    BMB Rep. 2014 Aug;47(8):433-8.
    Stigmasterol isolated from marine microalgae Navicula incerta induces apoptosis in human hepatoma HepG2 cells.[Pubmed: 24286323]
    Plant sterols have shown potent anti-proliferative effects and apoptosis induction against breast and prostate cancers. However, the effect of sterols against hepatic cancer has not been investigated.
    METHODS AND RESULTS:
    In the present study, we assessed whether the Stigmasterol isolated from Navicula incerta possesses apoptosis inductive effect in hepatocarcimona (HepG2) cells. According to the results, Stigmasterol has up-regulated the expression of pro-apoptotic gene expressions (Bax, p53) while down-regulating the anti-apoptotic genes (Bcl-2). Probably via mitochondrial apoptosis signaling pathway. With the induction of apoptosis caspase-8, 9 were activated. The DNA damage and increase in apoptotic cell numbers were observed through Hoechst staining, annexin V staining and cell cycle analysis.
    CONCLUSIONS:
    According to these results, we can suggest that the Stigmasterol shows potent apoptosis inductive effects and has the potential to be tested as an anti-cancer therapeutic against liver cancer.
    Animal Research:
    Pharm Biol. 2012 Jun;50(6):747-53.
    Fractionation of stigmasterol derivative and study of the effects of Celsia coromandelina aerial parts petroleum ether extract on appearance of puberty and ovarian steroidogenesis in immature mice.[Pubmed: 22092072]
    Celsia coromandelina Vahl (Scrophulariaceae) is a shrub found throughout Bangladesh and India, and it is distributed widely in the plains of West Bengal. It is used by the tribal people to treat diarrhea, dysentery, insomnia, skin eruption, fever, syphilis, helminthes infection, and to control fertility. The objective of this study was to fractionate Stigmasterol derivative and to investigate the effects of petroleum ether extract of C. coromandelina (PECC) aerial parts on the onset of reproductive maturity and the ovarian steroidogenesis in immature female mice.
    METHODS AND RESULTS:
    PECC was prepared by hot extraction process and one compound was isolated by preparative TLC from it. PECC was completely freed from solvent and administered in immature female mice intraperitoneally once on every alternate day for nine doses. The sexual maturity was observed by means of vaginal opening, first estrus (days), rate of body growth, changes in weight of ovary, uterus and pituitary. The content of ascorbic acid, cholesterol, Δ⁵-3β-hydroxy steroid dehydrogenase (Δ⁵-3β-HSD) and glucose 6-phosphate dehydrogenase (G 6-PDH) activities in ovaries and carbonic anhydrase activity in uterus were measured by means of biochemical technique in control and treated mice. The activity of PECC was compared with standard marker compound ethinyl estradiol. The isolated compound was characterized as Stigmasterol derivative. PECC treatment caused a remarkable delay (30.27 and 18.56%, respectively, by low dose) in sexual maturity compared to vehicle control as evidenced by the age of vaginal opening and appearance of first estrus (cornified smear). PECC treatment also caused a significant fall (58.6 and 50.0%, respectively, by low dose) in Δ⁵-3β-HSD and G 6-PDH activities involved in ovarian steroidogenesis compared to vehicle control. Total cholesterol and ascorbic acid content in ovaries and carbonic anhydrase activity in uterus were increased significantly (low dose by 49.3, 424.6 and 82.4%, respectively) along with a reduction in the weight of ovary, uterus and pituitary in comparison to that of control.
    CONCLUSIONS:
    Overall, these results demonstrate that PECC has a good antifertility effect and is responsible for the delayed development of sexual maturity, suppression of ovarian steroidogenesis and elevation of carbonic anhydrase activity in uterus of immature mice. This supports the claim by tribal people as a potential remedy for birth control.
    Fitoterapia. 2009 Mar;80(2):123-6.
    Thyroid inhibitory, antiperoxidative and hypoglycemic effects of stigmasterol isolated from Butea monosperma.[Pubmed: 19105977 ]
    Stigmasterol, isolated from the bark of Butea monosperma was evaluated for its thyroid hormone and glucose regulatory efficacy in mice.
    METHODS AND RESULTS:
    Its administration at 2.6 mg/kg/d for 20 days reduced serum triiodothyronine (T(3)), thyroxin (T(4)) and glucose concentrations as well as the activity of hepatic glucose-6-phophatase (G-6-Pase) with a concomitant increase in insulin indicating its thyroid inhibiting and hypoglycemic properties.
    CONCLUSIONS:
    A decrease in the hepatic lipid peroxidation (LPO) and an increase in the activities of catalase (CAT), superoxide dismutase (SOD) and glutathione (GSH) suggested its antioxidative potential. The highest concentration tested (5.2 mg/kg) evoked pro-oxidative activity.