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39025-23-5,MFCD01310757
Catalog No.:AA00C09W

39025-23-5 | (Z)-Guggulsterone

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1mg
≥95%
in stock  
$63.00   $44.00
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5mg
≥95%
in stock  
$156.00   $109.00
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10mg
≥95%
in stock  
$276.00   $193.00
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50mg
>98%
in stock  
$1,152.00   $807.00
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100mg
>98%
in stock  
$1,613.00   $1,129.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C09W
Chemical Name:
(Z)-Guggulsterone
CAS Number:
39025-23-5
Molecular Formula:
C21H28O2
Molecular Weight:
312.4458
MDL Number:
MFCD01310757
SMILES:
C/C=C/1\C(=O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
Properties
Properties
 
Form:
Solid  
MP:
>191°C (dec.)  
Storage:
2-8℃;Keep in dry area;  

Computed Properties
 
Complexity:
640  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
2  
XLogP3:
3.9  

Literature

Title: Alisol B 23-acetate protects against non-alcoholic steatohepatitis in mice via farnesoid X receptor activation.

Journal: Acta pharmacologica Sinica 20170101

Title: Development and validation of HPLC method for simultaneous estimation of piperine and guggulsterones in compound Unani formulation (tablets) and a nanoreservoir system.

Journal: Biomedical chromatography : BMC 20121001

Title: Enhanced antitumor effect of combination therapy with gemcitabine and guggulsterone in pancreatic cancer.

Journal: Pancreas 20121001

Title: Guggulsterone enhances antitumor activity of gemcitabine in gallbladder cancer cells through suppression of NF-κB.

Journal: Journal of cancer research and clinical oncology 20121001

Title: Discovery and optimization of 1,3,4-trisubstituted-pyrazolone derivatives as novel, potent, and nonsteroidal farnesoid X receptor (FXR) selective antagonists.

Journal: Journal of medicinal chemistry 20120823

Title: Bile acids acutely stimulate insulin secretion of mouse β-cells via farnesoid X receptor activation and K(ATP) channel inhibition.

Journal: Diabetes 20120601

Title: [Progress in the ligands and their complex structures of farnesoid X receptor].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20120601

Title: Hypolipidemic agent Z-guggulsterone: metabolism interplays with induction of carboxylesterase and bile salt export pump.

Journal: Journal of lipid research 20120301

Title: Guggulsterone induces heme oxygenase-1 expression through activation of Nrf2 in human mammary epithelial cells: PTEN as a putative target.

Journal: Carcinogenesis 20120201

Title: Novel stereoselective synthesis and chromatographic evaluation of E-guggulsterone.

Journal: Steroids 20120201

Title: Role of farnesoid X receptor (FXR) in the process of differentiation of bone marrow stromal cells into osteoblasts.

Journal: Bone 20111201

Title: Guggulsterone sensitizes hepatoma cells to TRAIL-induced apoptosis through the induction of CHOP-dependent DR5: involvement of ROS-dependent ER-stress.

Journal: Biochemical pharmacology 20111201

Title: 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.

Journal: Journal of pharmaceutical and biomedical analysis 20110910

Title: Simultaneous estimation of E- and Z-isomers of guggulsterone in rabbit plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study.

Journal: Biomedical chromatography : BMC 20110901

Title: Guggulsterone (GS) inhibits smokeless tobacco and nicotine-induced NF-κB and STAT3 pathways in head and neck cancer cells.

Journal: Carcinogenesis 20110301

Title: Reversal of multidrug resistance by guggulsterone in drug-resistant MCF-7 cell lines.

Journal: Chemotherapy 20110101

Title: Guggulsterone targets smokeless tobacco induced PI3K/Akt pathway in head and neck cancer cells.

Journal: PloS one 20110101

Title: TO901317 regulating apolipoprotein M expression mediates via the farnesoid X receptor pathway in Caco-2 cells.

Journal: Lipids in health and disease 20110101

Title: Guggulsterone suppresses LPS induced inflammation of human middle ear epithelial cells (HMEEC).

Journal: International journal of pediatric otorhinolaryngology 20101201

Title: Prevention of endotoxin-induced uveitis in rats by plant sterol guggulsterone.

Journal: Investigative ophthalmology & visual science 20101001

Title: Retinoic acid represses CYP7A1 expression in human hepatocytes and HepG2 cells by FXR/RXR-dependent and independent mechanisms.

Journal: Journal of lipid research 20100801

Title: Novel guggulsterone derivative GG-52 inhibits NF-kappaB signaling in intestinal epithelial cells and attenuates acute murine colitis.

Journal: Laboratory investigation; a journal of technical methods and pathology 20100701

Title: Guggulsterone suppresses bile acid-induced and constitutive caudal-related homeobox 2 expression in gut-derived adenocarcinoma cells.

Journal: Anticancer research 20100601

Title: Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile.

Journal: Chemico-biological interactions 20100330

Title: 14-3-3 zeta is a molecular target in guggulsterone induced apoptosis in head and neck cancer cells.

Journal: BMC cancer 20100101

Title: The plant sterol guggulsterone attenuates inflammation and immune dysfunction in murine models of inflammatory bowel disease.

Journal: Biochemical pharmacology 20091101

Title: Guggulsterone enhances head and neck cancer therapies via inhibition of signal transducer and activator of transcription-3.

Journal: Carcinogenesis 20091101

Title: Effects of guggulsterone isolated from Commiphora mukul in high fat diet induced diabetic rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20091001

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Reversal of P-glycoprotein-mediated multidrug resistance by guggulsterone in doxorubicin-resistant human myelogenous leukemia (K562/DOX) cells.

Journal: Die Pharmazie 20091001

Title: Anti-obesity effects of xanthohumol plus guggulsterone in 3T3-L1 adipocytes.

Journal: Journal of medicinal food 20090801

Title: Guggulsterone induces apoptosis in colon cancer cells and inhibits tumor growth in murine colorectal cancer xenografts.

Journal: Cancer letters 20090628

Title: Guggulsterone, an anti-inflammatory phytosterol, inhibits tissue factor and arterial thrombosis.

Journal: Basic research in cardiology 20090501

Title: Guggulsterone suppresses the activation of transcription factor IRF3 induced by TLR3 or TLR4 agonists.

Journal: International immunopharmacology 20090101

Title: Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.

Journal: Journal of natural products 20090101

Title: Guggulsterone: a potent farnesoid X receptor antagonist and its rapidly evolving role as a systemic anticarcinogenic agent.

Journal: Hepatology (Baltimore, Md.) 20081201

Title: Guggulsterone inhibits angiogenesis by blocking STAT3 and VEGF expression in colon cancer cells.

Journal: Oncology reports 20081201

Title: Protection against hydrogen peroxide-induced cytotoxicity in PC12 cells by guggulsterone.

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20081201

Title: Guggulsterone modulates MAPK and NF-kappaB pathways and inhibits skin tumorigenesis in SENCAR mice.

Journal: Carcinogenesis 20081001

Title: Guggulsterone, a plant sterol, inhibits NF-kappaB activation and protects pancreatic beta cells from cytokine toxicity.

Journal: Molecular and cellular endocrinology 20080716

Title: Guggulsterone blocks IL-1beta-mediated inflammatory responses by suppressing NF-kappaB activation in fibroblast-like synoviocytes.

Journal: Life sciences 20080606

Title: Guggulsterone, a farnesoid X receptor antagonist, inhibits constitutive and inducible STAT3 activation through induction of a protein tyrosine phosphatase SHP-1.

Journal: Cancer research 20080601

Title: Effects of plant sterols on human multidrug transporters ABCB1 and ABCC1.

Journal: Biochemical and biophysical research communications 20080502

Title: Omega-(2-Naphthyloxy) amino alkanes as a novel class of anti-hyperglycemic and lipid lowering agents.

Journal: Bioorganic & medicinal chemistry 20080301

Title: z-Guggulsterone, a constituent of Ayurvedic medicinal plant Commiphora mukul, inhibits angiogenesis in vitro and in vivo.

Journal: Molecular cancer therapeutics 20080101

Title: Guggulsterone inhibits adipocyte differentiation and induces apoptosis in 3T3-L1 cells.

Journal: Obesity (Silver Spring, Md.) 20080101

Title: Enhanced effects of guggulsterone plus 1,25(OH)2D3 on 3T3-L1 adipocytes.

Journal: Biochemical and biophysical research communications 20071221

Title: Guggulsterone-induced apoptosis in human prostate cancer cells is caused by reactive oxygen intermediate dependent activation of c-Jun NH2-terminal kinase.

Journal: Cancer research 20070801

Title: 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.

Journal: Biochemical pharmacology 20070630

Title: Guggulsterone production in cell suspension cultures of the guggul tree, Commiphora wightii, grown in shake-flasks and bioreactors.

Journal: Biotechnology letters 20070601

Title: Natural products as a gold mine for arthritis treatment.

Journal: Current opinion in pharmacology 20070601

Title: Design, synthesis, and evaluation of non-steroidal farnesoid X receptor (FXR) antagonist.

Journal: Bioorganic & medicinal chemistry 20070401

Title: The hypolipidemic agent guggulsterone regulates the expression of human bile salt export pump: dominance of transactivation over farsenoid X receptor-mediated antagonism.

Journal: The Journal of pharmacology and experimental therapeutics 20070301

Title: Therapeutic effects of guggul and its constituent guggulsterone: cardiovascular benefits.

Journal: Cardiovascular drug reviews 20070101

Title: Enhanced pro-apoptotic and anti-adipogenic effects of genistein plus guggulsterone in 3T3-L1 adipocytes.

Journal: BioFactors (Oxford, England) 20070101

Title: Plant sterol guggulsterone inhibits nuclear factor-kappaB signaling in intestinal epithelial cells by blocking IkappaB kinase and ameliorates acute murine colitis.

Journal: Inflammatory bowel diseases 20061201

Title: The nuclear hormone receptor farnesoid X receptor (FXR) is activated by androsterone.

Journal: Endocrinology 20060901

Title: Guggulsterone inhibits osteoclastogenesis induced by receptor activator of nuclear factor-kappaB ligand and by tumor cells by suppressing nuclear factor-kappaB activation.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060115

Title: Expression of the bile acid receptor FXR in Barrett's esophagus and enhancement of apoptosis by guggulsterone in vitro.

Journal: Molecular cancer 20060101

Title: Guggulsterones induce apoptosis and differentiation in acute myeloid leukemia: identification of isomer-specific antileukemic activities of the pregnadienedione structure.

Journal: Molecular cancer therapeutics 20051201

Title: Is antagonism of E/Z-guggulsterone at the farnesoid X receptor mediated by a noncanonical binding site? A molecular modeling study.

Journal: Journal of medicinal chemistry 20051103

Title: 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.

Journal: Molecular cancer therapeutics 20051101

Title: The ratio of constitutive androstane receptor to pregnane X receptor determines the activity of guggulsterone against the Cyp2b10 promoter.

Journal: The Journal of pharmacology and experimental therapeutics 20050701

Title: Fungal metabolites of (E)-guggulsterone and their antibacterial and radical-scavenging activities.

Journal: Chemistry & biodiversity 20050401

Title: Regulation of carbohydrate metabolism by the farnesoid X receptor.

Journal: Endocrinology 20050301

Title: The hypolipidemic natural product guggulsterone is a promiscuous steroid receptor ligand.

Journal: Molecular pharmacology 20050301

Title: Guggulsterone inhibits NF-kappaB and IkappaBalpha kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis.

Journal: The Journal of biological chemistry 20041105

Title: HPTLC method for guggulsterone. II. Stress degradation studies on guggulsterone.

Journal: Journal of pharmaceutical and biomedical analysis 20040921

Title: HPTLC method for guggulsterone. I. Quantitative determination of E- and Z-guggulsterone in herbal extract and pharmaceutical dosage form.

Journal: Journal of pharmaceutical and biomedical analysis 20040921

Title: Guggulsterone activates multiple nuclear receptors and induces CYP3A gene expression through the pregnane X receptor.

Journal: The Journal of pharmacology and experimental therapeutics 20040801

Title: The hypolipidemic natural product Commiphora mukul and its component guggulsterone inhibit oxidative modification of LDL.

Journal: Atherosclerosis 20040201

Title: Guggulipid for the treatment of hypercholesterolemia: a randomized controlled trial.

Journal: JAMA 20030813

Title: Guggulsterone antagonizes farnesoid X receptor induction of bile salt export pump but activates pregnane X receptor to inhibit cholesterol 7alpha-hydroxylase gene.

Journal: Biochemical and biophysical research communications 20030425

Title: Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump.

Journal: The Journal of biological chemistry 20030321

Title: Guggulsterone: an old approach to a new problem.

Journal: Trends in endocrinology and metabolism: TEM 20020901

Title: The hypolipidemic natural product guggulsterone acts as an antagonist of the bile acid receptor.

Journal: Molecular endocrinology (Baltimore, Md.) 20020701

Title: A natural product that lowers cholesterol as an antagonist ligand for FXR.

Journal: Science (New York, N.Y.) 20020531

Title: Simultaneous determination of E- and Z-guggulsterones in dietary supplements containing Commiphora mukul extract (guggulipid) by liquid chromatography.

Journal: Journal of AOAC International 20010101

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Tags:39025-23-5 Molecular Formula|39025-23-5 MDL|39025-23-5 SMILES|39025-23-5 (Z)-Guggulsterone