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34080-08-5,MFCD11041271
Catalog No.:AA00C5MI

34080-08-5 | PROTOPANAXTRIOL

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1mg
≥95%
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$52.00   $36.00
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5mg
≥95%
in stock  
$172.00   $120.00
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10mg
≥95%
in stock  
$319.00   $223.00
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25mg
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$729.00   $510.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C5MI
Chemical Name:
PROTOPANAXTRIOL
CAS Number:
34080-08-5
Molecular Formula:
C30H52O4
Molecular Weight:
476.7315
MDL Number:
MFCD11041271
SMILES:
CC(=CCC[C@@]([C@H]1CC[C@@]2([C@@H]1[C@H](O)C[C@H]1[C@@]2(C)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)O)C)(O)C)C
Properties
Computed Properties
 
Complexity:
817  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
11  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
5.9  

Literature

Title: Cytochrome P450 CYP716A53v2 catalyzes the formation of protopanaxatriol from protopanaxadiol during ginsenoside biosynthesis in Panax ginseng.

Journal: Plant & cell physiology 20120901

Title: Fungal sensitivity to and enzymatic deglycosylation of ginsenosides.

Journal: Phytochemistry 20120601

Title: Panax ginseng extract rich in ginsenoside protopanaxatriol attenuates blood pressure elevation in spontaneously hypertensive rats by affecting the Akt-dependent phosphorylation of endothelial nitric oxide synthase.

Journal: Journal of agricultural and food chemistry 20120328

Title: Protective effect of ginseng sapogenins against 2,2'-azobis (1-aminopropane) dihydrochloride (AAPH)-induced LLC-PK₁ cell damage.

Journal: Bioorganic & medicinal chemistry letters 20120101

Title: The in vitro structure-related anti-cancer activity of ginsenosides and their derivatives.

Journal: Molecules (Basel, Switzerland) 20111219

Title: A novel ginsenosidase from an Aspergillus strain hydrolyzing 6-O-multi-glycosides of protopanaxatriol-type ginsenosides, named ginsenosidase type IV.

Journal: Journal of microbiology and biotechnology 20111001

Title: Simultaneous determination of ginsenoside (G-Re, G-Rg1, G-Rg2, G-F1, G-Rh1) and protopanaxatriol in human plasma and urine by LC-MS/MS and its application in a pharmacokinetics study of G-Re in volunteers.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110715

Title: Protopanaxatriol-type ginsenosides from the root of Panax ginseng.

Journal: Journal of agricultural and food chemistry 20110112

Title: Effect of 20(S)-protopanaxatriol and its epimeric derivatives on myocardial injury induced by isoproterenol.

Journal: Arzneimittel-Forschung 20110101

Title: Anti-Obesity effects of protopanaxdiol types of Ginsenosides isolated from the leaves of American ginseng (Panax quinquefolius L.) in mice fed with a high-fat diet.

Journal: Fitoterapia 20101201

Title: Microsomal cytochrome p450-mediated metabolism of protopanaxatriol ginsenosides: metabolite profile, reaction phenotyping, and structure-metabolism relationship.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20101001

Title: [Pharmacokinetics of ginsenosides Rg1 and its metabolites in rats].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20100501

Title: Protopanaxatriol metabolites identified by LC-MS/MS after oral administration in mice.

Journal: International journal of clinical pharmacology and therapeutics 20100401

Title: The ginsenoside protopanaxatriol protects endothelial cells from hydrogen peroxide-induced cell injury and cell death by modulating intracellular redox status.

Journal: Free radical biology & medicine 20100201

Title: Isolation, synthesis and structures of ginsenoside derivatives and their anti-tumor bioactivity.

Journal: Molecules (Basel, Switzerland) 20100119

Title: Microbial conversion of rare ginsenoside Rf to 20(S)-protopanaxatriol by Aspergillus niger.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Antioxidant and apoptotic effects of korean white ginseng extracted with the same ratio of protopanaxadiol and protopanaxatriol saponins in human hepatoma HepG2 cells.

Journal: Annals of the New York Academy of Sciences 20090801

Title: Improvement of memory in mice and increase of hippocampal excitability in rats by ginsenoside Rg1's metabolites ginsenoside Rh1 and protopanaxatriol.

Journal: Journal of pharmacological sciences 20090401

Title: Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells.

Journal: British journal of pharmacology 20090201

Title: Comparison of the antiobesity effects of the protopanaxadiol- and protopanaxatriol-type saponins of red ginseng.

Journal: Phytotherapy research : PTR 20090101

Title: Determination of 20(S)-ginsenoside Rh1 and its aglycone 20(S)-protopanaxatriol in rat plasma by sensitive LC-APCI-MS method and its application to pharmacokinetic study.

Journal: European journal of mass spectrometry (Chichester, England) 20090101

Title: [Clinical value of protoparaxotril saporlirs combined with aspirin in the secondary prevention of cerebral infarction].

Journal: Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20080901

Title: Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra.

Journal: Journal of natural products 20080301

Title: Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products.

Journal: Phytochemistry 20071001

Title: Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea.

Journal: Journal of natural products 20070701

Title: Adjuvant effects of protopanaxadiol and protopanaxatriol saponins from ginseng roots on the immune responses to ovalbumin in mice.

Journal: Vaccine 20070122

Title: [Analysis of ginsenosides in Sheng-Mai-Yin decoction by high performance liquid chromatography-diode array detection-electrospray mass spectrometry].

Journal: Se pu = Chinese journal of chromatography 20060701

Title: Ginsenoside metabolites, rather than naturally occurring ginsenosides, lead to inhibition of human cytochrome P450 enzymes.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20060601

Title: Natural products from ginseng inhibit [3H]batrachotoxinin A 20-alpha-benzoate binding to Na+ channels in mammalian brain.

Journal: European journal of pharmacology 20060113

Title: Structure and biological activity of protopanaxatriol-type saponins from the roots of Panax notoginseng.

Journal: International immunopharmacology 20060101

Title: Microbial transformation of 20(S)-protopanaxatriol by Mucor spinosus.

Journal: Journal of natural products 20050501

Title: Protopanaxatriol-type ginsenosides differentially modulate type 1 and type 2 cytokines production from murine splenocytes.

Journal: Planta medica 20050301

Title: Immunoenhancing activity of protopanaxatriol-type ginsenoside-F3 in murine spleen cells.

Journal: Acta pharmacologica Sinica 20041201

Title: The inhibitory effect of intestinal bacterial metabolite of ginsenosides on CYP3A activity.

Journal: Biological & pharmaceutical bulletin 20041001

Title: 20(S)-Protopanaxatriol, one of ginsenoside metabolites, inhibits inducible nitric oxide synthase and cyclooxygenase-2 expressions through inactivation of nuclear factor-kappaB in RAW 264.7 macrophages stimulated with lipopolysaccharide.

Journal: Cancer letters 20040308

Title: Ginsenosides 20(S)-protopanaxadiol and Rh2 reduce cell proliferation and increase sub-G1 cells in two cultured intestinal cell lines, Int-407 and Caco-2.

Journal: Canadian journal of physiology and pharmacology 20040301

Title: In vitro inhibition of adrenal catecholamine secretion by steroidal metabolites of ginseng saponins.

Journal: Biochemical pharmacology 20031201

Title: Differential effect of bovine serum albumin on ginsenoside metabolite-induced inhibition of alpha3beta4 nicotinic acetylcholine receptor expressed in Xenopus oocytes.

Journal: Archives of pharmacal research 20031001

Title: Reversal of P-glycoprotein-mediated multidrug resistance by protopanaxatriol ginsenosides from Korean red ginseng.

Journal: Planta medica 20030301

Title: Ginsenosides inhibit EGF-induced proliferation of renal proximal tubule cells via decrease of c-fos and c-jun gene expression in vitro.

Journal: Planta medica 20021101

Title: Can ginsenosides protect human erythrocytes against free-radical-induced hemolysis?

Journal: Biochimica et biophysica acta 20020815

Title: Prevention of growth and metastasis of murine melanoma through enhanced natural-killer cytotoxicity by fatty acid-conjugate of protopanaxatriol.

Journal: Biological & pharmaceutical bulletin 20020701

Title: Ginsenosides protect apical transporters of cultured proximal tubule cells from dysfunctions induced by h(2)o(2).

Journal: Kidney & blood pressure research 20020101

Title: Regioselective enzymatic glycosylation of natural polyhydroxylated compounds: galactosylation and glucosylation of protopanaxatriol ginsenosides.

Journal: The Journal of organic chemistry 20010112

Title: Korean red ginseng saponins with low ratios of protopanaxadiol and protopanaxatriol saponin improve scopolamine-induced learning disability and spatial working memory in mice.

Journal: Journal of ethnopharmacology 19990801

Title: Leung KW, et al. Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. Br J Pharmacol. 2009 Feb;156(4):626-37.

Title: Oh GS, et al. 20(S)-protopanaxatriol inhibits liver X receptor α-mediated expression of lipogenic genes in hepatocytes. J Pharmacol Sci. 2015 Jun;128(2):71-7.

Title: Huang Q, et al. Co-administration of 20(S)-protopanaxatriol (g-PPT) and EGFR-TKI overcomes EGFR-TKI resistance by decreasing SCD1 induced lipid accumulation in non-small cell lung cancer. J Exp Clin Cancer Res. 2019;38(1):129. Published 2019 Mar 15.

Title: Zhang H, et al. 20(S)-Protopanaxadiol-Induced Apoptosis in MCF-7 Breast Cancer Cell Line through the Inhibition of PI3K/AKT/mTOR Signaling Pathway. Int J Mol Sci. 2018;19(4):1053. Published 2018 Apr 2.

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