guggulsterone E
pregna-4,17(20)-diene-3,16-dione, (17E)-
Identification
| Name | guggulsterone E |
| IUPAC | (8R,9S,10R,13S,14S,17E)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione |
| CAS Number | 39025-24-6 |
| FDA UNII | 9B259YE66O |
| Molecular Formula | C21 H28 O2 |
| Molecular Weight | 312.45256000 |
| MDL Number | MFCD01310758 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 463.30 °C. @ 760.00 mm Hg (est) |
| Flash Point | 342.00 °F. TCC ( 172.30 °C. ) (est) |
| logP (o/w) | 3.650 (est) |
| Soluble in | water, 5.144 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for guggulsterone E usage levels up to | not for fragrance use. |
| Recommendation for guggulsterone E flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(8R,9S,10R,13S,14S,17E)-17-
ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
(E)-
guggulsterone
E-
guggulsterone
trans-
guggulsterone
guggulsterone, (E)-
pregna-4,17(20)-diene-3,16-dione, (17E)-
PubMed:
Alisol B 23-acetate promotes liver regeneration in mice after partial hepatectomy via activating farnesoid X receptor.
PubMed:
Reversal of doxorubicin resistance by guggulsterone of Commiphora mukul in vivo.
PubMed:
Protective Effects of Calycosin Against CCl4-Induced Liver Injury with Activation of FXR and STAT3 in Mice.
PubMed:
The appetite regulatory effect of guggulsterones in rats: a repertoire of plasma hormones and neurotransmitters.
PubMed:
Amiloride and guggulsterone suppression of esophageal cancer cell growth in vitro and in nude mouse xenografts.
PubMed:
Guggulsterone inhibits prostate cancer growth via inactivation of Akt regulated by ATP citrate lyase signaling.
PubMed:
Conformational dynamics of human FXR-LBD ligand interactions studied by hydrogen/deuterium exchange mass spectrometry: insights into the antagonism of the hypolipidemic agent Z-guggulsterone.
PubMed:
Guggulsterone of Commiphora mukul resin reverses drug resistance in imatinib-resistant leukemic cells by inhibiting cyclooxygenase-2 and P-glycoprotein.
PubMed:
Development and Validation of RP-HPLC Method for Simultaneous Estimation of Picroside I, Plumbagin, and Z-guggulsterone in Tablet Formulation.
PubMed:
[Farnesoid-X-receptor blockade reduces myocardial reperfusion injury in cholesterol-fed apolipoprotein E knockout mice].
PubMed:
Guggulsterone regulates the function and expression of P-glycoprotein in rat brain microvessel endothelial cells.
PubMed:
Guggulsterone decreases proliferation and metastatic behavior of pancreatic cancer cells by modulating JAK/STAT and Src/FAK signaling.
PubMed:
Targeting beta-catenin signaling to induce apoptosis in human breast cancer cells by z-guggulsterone and Gugulipid extract of Ayurvedic medicine plant Commiphora mukul.
PubMed:
Guggulsterone attenuates activation and survival of hepatic stellate cell by inhibiting nuclear factor kappa B activation and inducing apoptosis.
PubMed:
Identification of 15d-PGJ2 as an antagonist of farnesoid X receptor: molecular modeling with biological evaluation.
PubMed:
Dietary phytochemicals as potent chemotherapeutic agents against breast cancer: Inhibition of NF-κB pathway via molecular interactions in rel homology domain of its precursor protein p105.
PubMed:
The guggulsterone derivative GG-52 inhibits NF-κB signaling in bone marrow-derived dendritic cells and attenuates colitis in IL-10 knockout mice.
PubMed:
Expression of DNA methyltransferases in breast cancer patients and to analyze the effect of natural compounds on DNA methyltransferases and associated proteins.
PubMed:
Guggulsterone sensitizes glioblastoma cells to Sonic hedgehog inhibitor SANT-1 induced apoptosis in a Ras/NFκB dependent manner.
PubMed:
Deriving dopaminergic neurons for clinical use. A practical approach.
PubMed:
Inhibition of farnesoid X receptor controls esophageal cancer cell growth in vitro and in nude mouse xenografts.
PubMed:
Proteomic analysis of rosiglitazone and guggulsterone treated 3T3-L1 preadipocytes.
PubMed:
Cis-guggulsterone inhibits the IKK/NF-κB pathway, whereas trans-guggulsterone inhibits MAPK/AP-1 in MCFâ7 breast cancer cells: guggulsterone regulates MMPâ9 expression in an isomer-specific manner.
PubMed:
Farnesoid X receptor targeting for hepatitis C: study protocol for a proof-of-concept trial.
PubMed:
The guggulsterone derivative GG-52 inhibits NF-κB signaling in gastric epithelial cells and ameliorates ethanol-induced gastric mucosal lesions in mice.
PubMed:
Src-mediated cross-talk between farnesoid X and epidermal growth factor receptors inhibits human intestinal cell proliferation and tumorigenesis.
PubMed:
Reversion of P-glycoprotein-mediated multidrug resistance by guggulsterone in multidrug-resistant human cancer cell lines.
PubMed:
Protective effect of guggulsterone against cardiomyocyte injury induced by doxorubicin in vitro.
PubMed:
Up-regulation of FXR isoforms is not required for stimulation of the expression of genes involved in the lack of response of colon cancer to chemotherapy.
PubMed:
Cancer chemopreventive and therapeutic potential of guggulsterone.
PubMed:
Guggulsterone inhibits melanogenesis in B16 murine melanoma cells by downregulating tyrosinase expression.
PubMed:
Guggulsterone enhances antitumor activity of gemcitabine in gallbladder cancer cells through suppression of NF-κB.
PubMed:
Enhanced antitumor effect of combination therapy with gemcitabine and guggulsterone in pancreatic cancer.
PubMed:
Bile acids acutely stimulate insulin secretion of mouse β-cells via farnesoid X receptor activation and K(ATP) channel inhibition.
PubMed:
Three new α-glucosidase inhibitors from guggul, the oleogum resin of Commiphora wightii.
PubMed:
Hypolipidemic agent Z-guggulsterone: metabolism interplays with induction of carboxylesterase and bile salt export pump.
PubMed:
Novel stereoselective synthesis and chromatographic evaluation of E-guggulsterone.
PubMed:
Guggulsterone induces heme oxygenase-1 expression through activation of Nrf2 in human mammary epithelial cells: PTEN as a putative target.
PubMed:
TO901317 regulating apolipoprotein M expression mediates via the farnesoid X receptor pathway in Caco-2 cells.
PubMed:
Guggulsterone sensitizes hepatoma cells to TRAIL-induced apoptosis through the induction of CHOP-dependent DR5: involvement of ROS-dependent ER-stress.
PubMed:
Role of farnesoid X receptor (FXR) in the process of differentiation of bone marrow stromal cells into osteoblasts.
PubMed:
Effective separation and analysis of E- and Z-guggulsterones in Commiphora mukul resin, guggulipid and their pharmaceutical product by high performance thin-layer chromatography-densitometric method.
PubMed:
Guggulsterone targets smokeless tobacco induced PI3K/Akt pathway in head and neck cancer cells.
PubMed:
Farnesoid X receptor, overexpressed in pancreatic cancer with lymph node metastasis promotes cell migration and invasion.
PubMed:
Reversal of multidrug resistance by guggulsterone in drug-resistant MCF-7 cell lines.
PubMed:
Simultaneous estimation of E- and Z-isomers of guggulsterone in rabbit plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study.
PubMed:
Guggulsterone-mediated enhancement of radiosensitivity in human tumor cell lines.
PubMed:
Guggulsterone (GS) inhibits smokeless tobacco and nicotine-induced NF-κB and STAT3 pathways in head and neck cancer cells.
PubMed:
Inhibition of EGFR-STAT3 signaling with erlotinib prevents carcinogenesis in a chemically-induced mouse model of oral squamous cell carcinoma.
PubMed:
14-3-3 zeta is a molecular target in guggulsterone induced apoptosis in head and neck cancer cells.
PubMed:
Reactive oxygen species-dependent apoptosis by gugulipid extract of Ayurvedic medicine plant Commiphora mukul in human prostate cancer cells is regulated by c-Jun N-terminal kinase.
PubMed:
Guggulsterone suppresses LPS induced inflammation of human middle ear epithelial cells (HMEEC).
PubMed:
Regulation of human carbonyl reductase 3 (CBR3; SDR21C2) expression by Nrf2 in cultured cancer cells.
PubMed:
Guggulsterone suppresses bile acid-induced and constitutive caudal-related homeobox 2 expression in gut-derived adenocarcinoma cells.
PubMed:
Overcoming multidrug resistance in human cancer cells by natural compounds.
PubMed:
Prevention of endotoxin-induced uveitis in rats by plant sterol guggulsterone.
PubMed:
Novel guggulsterone derivative GG-52 inhibits NF-kappaB signaling in intestinal epithelial cells and attenuates acute murine colitis.
PubMed:
Guggullipid derivatives: synthesis and applications.
PubMed:
Bile acids induce cdx2 expression through the farnesoid x receptor in gastric epithelial cells.
PubMed:
Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile.
PubMed:
Reversal of P-glycoprotein-mediated multidrug resistance by guggulsterone in doxorubicin-resistant human myelogenous leukemia (K562/DOX) cells.
PubMed:
Guggulsterone enhances head and neck cancer therapies via inhibition of signal transducer and activator of transcription-3.
PubMed:
Anti-obesity effects of xanthohumol plus guggulsterone in 3T3-L1 adipocytes.
PubMed:
Bortezomib up-regulates activated signal transducer and activator of transcription-3 and synergizes with inhibitors of signal transducer and activator of transcription-3 to promote head and neck squamous cell carcinoma cell death.
PubMed:
Effects of guggulsterone isolated from Commiphora mukul in high fat diet induced diabetic rats.
PubMed:
The plant sterol guggulsterone attenuates inflammation and immune dysfunction in murine models of inflammatory bowel disease.
PubMed:
Protection against hydrogen peroxide-induced cytotoxicity in PC12 cells by guggulsterone.
PubMed:
Guggulsterone induces apoptosis in colon cancer cells and inhibits tumor growth in murine colorectal cancer xenografts.
PubMed:
The guggul for chronic diseases: ancient medicine, modern targets.
PubMed:
Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
PubMed:
Deoxycholate promotes survival of breast cancer cells by reducing the level of pro-apoptotic ceramide.
PubMed:
Guggulsterone inhibits angiogenesis by blocking STAT3 and VEGF expression in colon cancer cells.
PubMed:
Guggulsterone suppresses the activation of transcription factor IRF3 induced by TLR3 or TLR4 agonists.
PubMed:
Guggulsterone: a potent farnesoid X receptor antagonist and its rapidly evolving role as a systemic anticarcinogenic agent.
PubMed:
Guggulsterone, an anti-inflammatory phytosterol, inhibits tissue factor and arterial thrombosis.
PubMed:
Guggulsterone modulates MAPK and NF-kappaB pathways and inhibits skin tumorigenesis in SENCAR mice.
PubMed:
Enhanced pro-apoptotic and anti-adipogenic effects of genistein plus guggulsterone in 3T3-L1 adipocytes.
PubMed:
Guggulsterone, a farnesoid X receptor antagonist, inhibits constitutive and inducible STAT3 activation through induction of a protein tyrosine phosphatase SHP-1.
PubMed:
Bile acid-stimulated expression of the farnesoid X receptor enhances the immune response in Barrett esophagus.
PubMed:
Guggulsterone blocks IL-1beta-mediated inflammatory responses by suppressing NF-kappaB activation in fibroblast-like synoviocytes.
PubMed:
Guggulsterone, a plant sterol, inhibits NF-kappaB activation and protects pancreatic beta cells from cytokine toxicity.
PubMed:
Effects of plant sterols on human multidrug transporters ABCB1 and ABCC1.
PubMed:
Guggulsterone inhibits adipocyte differentiation and induces apoptosis in 3T3-L1 cells.
PubMed:
z-Guggulsterone, a constituent of Ayurvedic medicinal plant Commiphora mukul, inhibits angiogenesis in vitro and in vivo.
PubMed:
Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities.
PubMed:
Enhancement of genotype 1 hepatitis C virus replication by bile acids through FXR.
PubMed:
Therapeutic effects of guggul and its constituent guggulsterone: cardiovascular benefits.
PubMed:
Enhanced effects of guggulsterone plus 1,25(OH)2D3 on 3T3-L1 adipocytes.
PubMed:
Guggulsterone-induced apoptosis in human prostate cancer cells is caused by reactive oxygen intermediate dependent activation of c-Jun NH2-terminal kinase.
PubMed:
Bile acids promote the expression of hepatitis C virus in replicon-harboring cells.
PubMed:
Gugulipid, an extract of Commiphora whighitii with lipid-lowering properties, has protective effects against streptozotocin-induced memory deficits in mice.
PubMed:
Natural products as a gold mine for arthritis treatment.
PubMed:
Guggulsterone inhibits tumor cell proliferation, induces S-phase arrest, and promotes apoptosis through activation of c-Jun N-terminal kinase, suppression of Akt pathway, and downregulation of antiapoptotic gene products.
PubMed:
Guggulsterone production in cell suspension cultures of the guggul tree, Commiphora wightii, grown in shake-flasks and bioreactors.
PubMed:
Fungal metabolites of (E)-guggulsterone and their antibacterial and radical-scavenging activities.
PubMed:
The hypolipidemic agent guggulsterone regulates the expression of human bile salt export pump: dominance of transactivation over farsenoid X receptor-mediated antagonism.
PubMed:
Plant sterol guggulsterone inhibits nuclear factor-kappaB signaling in intestinal epithelial cells by blocking IkappaB kinase and ameliorates acute murine colitis.
PubMed:
Expression of the bile acid receptor FXR in Barrett's esophagus and enhancement of apoptosis by guggulsterone in vitro.
PubMed:
The farnesoid X receptor promotes adipocyte differentiation and regulates adipose cell function in vivo.
PubMed:
The nuclear hormone receptor farnesoid X receptor (FXR) is activated by androsterone.
PubMed:
Lipids isolated from bone induce the migration of human breast cancer cells.
PubMed:
Guggulsterone inhibits osteoclastogenesis induced by receptor activator of nuclear factor-kappaB ligand and by tumor cells by suppressing nuclear factor-kappaB activation.
PubMed:
Guggulsterones induce apoptosis and differentiation in acute myeloid leukemia: identification of isomer-specific antileukemic activities of the pregnadienedione structure.
PubMed:
Caspase-dependent apoptosis induction by guggulsterone, a constituent of Ayurvedic medicinal plant Commiphora mukul, in PC-3 human prostate cancer cells is mediated by Bax and Bak.
PubMed:
Is antagonism of E/Z-guggulsterone at the farnesoid X receptor mediated by a noncanonical binding site? A molecular modeling study.
PubMed:
Xanthohumol, the chalcone from beer hops (Humulus lupulus L.), is the ligand for farnesoid X receptor and ameliorates lipid and glucose metabolism in KK-A(y) mice.
PubMed:
The ratio of constitutive androstane receptor to pregnane X receptor determines the activity of guggulsterone against the Cyp2b10 promoter.
PubMed:
Bile acid signaling through FXR induces intracellular adhesion molecule-1 expression in mouse liver and human hepatocytes.
PubMed:
The hypolipidemic natural product guggulsterone is a promiscuous steroid receptor ligand.
PubMed:
HPTLC method for guggulsterone. I. Quantitative determination of E- and Z-guggulsterone in herbal extract and pharmaceutical dosage form.
PubMed:
HPTLC method for guggulsterone. II. Stress degradation studies on guggulsterone.
PubMed:
Guggulsterone inhibits NF-kappaB and IkappaBalpha kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis.
PubMed:
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.
PubMed:
Guggulsterone activates multiple nuclear receptors and induces CYP3A gene expression through the pregnane X receptor.
PubMed:
The hypolipidemic natural product Commiphora mukul and its component guggulsterone inhibit oxidative modification of LDL.
PubMed:
A natural product ligand of the oxysterol receptor, liver X receptor.
PubMed:
Cardioprotective activity of synthetic guggulsterone (E and Z-isomers) in isoproterenol induced myocardial ischemia in rats: A comparative study.
PubMed:
Guggulsterone antagonizes farnesoid X receptor induction of bile salt export pump but activates pregnane X receptor to inhibit cholesterol 7alpha-hydroxylase gene.
PubMed:
GUGULIPID: a natural cholesterol-lowering agent.
PubMed:
Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump.
PubMed:
Inhibition of LPS-induced NO production by the oleogum resin of Commiphora wightii and its constituents.
PubMed:
Brine shrimp lethality bioassay of selected Indian medicinal plants.
PubMed:
Guggulsterone: an old approach to a new problem.
PubMed:
The hypolipidemic natural product guggulsterone acts as an antagonist of the bile acid receptor.
PubMed:
A natural product that lowers cholesterol as an antagonist ligand for FXR.
PubMed:
Simultaneous determination of E- and Z-guggulsterones in dietary supplements containing Commiphora mukul extract (guggulipid) by liquid chromatography.
PubMed:
High-performance liquid chromatographic method for fingerprinting and quantitative determination of E- and Z-guggulsterones in Commiphora mukul resin and its products.
PubMed:
Simultaneous determination of the stereoisomers of guggulsterone in serum by high-performance liquid chromatography.
PubMed:
Microbial transformations of hypolipemic E-guggulsterone.
PubMed:
A study of effect of guggulsterone on hyperlipidemia of secondary glomerulopathy.
PubMed:
Sensitive high-performance liquid chromatographic assay method for the determination of guggulsterone in serum.
PubMed:
Nodulocystic acne: oral gugulipid versus tetracycline.
PubMed:
Stimulation of low density lipoprotein receptor activity in liver membrane of guggulsterone treated rats.
PubMed:
Reversal of changes of lipid peroxide, xanthine oxidase and superoxide dismutase by cardio-protective drugs in isoproterenol induced myocardial necrosis in rats.
PubMed:
Cardiac sarcolemma enzymes & liver microsomal cytochrome P450 in isoproterenol treated rats.
PubMed:
Thyroid stimulatory action of (Z)-guggulsterone: mechanism of action.
PubMed:
Thyroid Stimulating Action of Z-Guggulsterone Obtained from Commiphora mukul.
PubMed:
Thyroid stimulating action of Z-guggulsterone obtained from Commiphora mukul.