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guggulsterone Z
pregna-4,17(20)-diene-3,16-dione, (17Z)-

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Name:(8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
CAS Number: 39025-23-5Picture of molecule3D/inchi
Other(deleted CASRN):137682-26-9
FDA UNII: 6CST3U34GN
Nikkaji Web:J16.524G
MDL:MFCD01310757
XlogP3-AA:3.90 (est)
Molecular Weight:312.45256000
Formula:C21 H28 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Z-Guggulsterone ≥98%
Odor: characteristic
Use: Z-Guggulsterone is a broad spectrum steroid receptor ligand that acts as a min
ExtraSynthese
For experimental / research use only.
Guggulsterone Z (HPLC) ≥90%
Santa Cruz Biotechnology
For experimental / research use only.
Z-Guggulsterone >98%
Sigma-Aldrich: Sigma
For experimental / research use only.
(Z)-Guggulsterone ≥89% (HPLC), powder
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for guggulsterone Z usage levels up to:
 not for fragrance use.
 
Recommendation for guggulsterone Z flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6450278
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
Chemidplus:0039025235
 
References:
 (8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:39025-23-5
Pubchem (cid):6450278
Pubchem (sid):135259863
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
(8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
(Z)-guggulsterone
cis-guggulsterone
Z-guggulsterone
 guggulsterone, (Z)-
 pregna-4,17(20)-diene-3,16-dione, (17Z)-
 

Articles:

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 MCF‑7 breast cancer cells: guggulsterone regulates MMP‑9 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.
 
Notes:
None found
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