Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H52O3 |
| Molecular Weight | 460.7321 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@]2(C)[C@]1([H])[C@H](O)C[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]23C)[C@](C)(O)CCC=C(C)C
InChI
InChIKey=PYXFVCFISTUSOO-VUFVRDRTSA-N
InChI=1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30+/m0/s1
| Molecular Formula | C30H52O3 |
| Molecular Weight | 460.7321 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26420067 | https://clinicaltrials.gov/ct2/show/record/NCT02395263 | https://www.ncbi.nlm.nih.gov/pubmed/25453798
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26420067 | https://clinicaltrials.gov/ct2/show/record/NCT02395263 | https://www.ncbi.nlm.nih.gov/pubmed/25453798
Protopanaxadiol (PPD, Yuxintine) is an organic compound characterizing a group of ginsenosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng). Protopanaxadiol has a wide range of pharmacologic activities, including antiestrogen, anti-inflammatory, antitumor, vasodilating, cardioprotection, and antidepressant effects. The antidepressant effect of oral Protopanaxadiol had been confirmed by several different animal models, such as forced swimming test tail suspension test, and rat olfactory bulbectomy depression models. Protopanaxadiol was found to have much fewer adverse drug reactions than currently-used first-line antidepressants. It is almostdevoid of sedation, sexual dysfunction, weight gain, cardiovascular complications, and anticholinergic effects. Protopanaxadiol was in phase II clinical trials as a novel antidepressant in China.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Metabolism of ginsenoside Rb1 and panaxadiol saponins by fungi]. | 2001 Aug |
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| In vitro study of the relationship between the structure of ginsenoside and its antioxidative or prooxidative activity in free radical induced hemolysis of human erythrocytes. | 2003 Apr 23 |
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| Modulating effects of Korean ginseng saponins on ovarian function in immature rats. | 2003 Nov |
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| A novel ginseng saponin metabolite induces apoptosis and down-regulates fibroblast growth factor receptor 3 in myeloma cells. | 2003 Oct |
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| Transformation of ginseng saponins to ginsenoside Rh2 by acids and human intestinal bacteria and biological activities of their transformants. | 2004 Jan |
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| Ginsenoside Rh2 reduces ischemic brain injury in rats. | 2004 Mar |
|
| The inhibitory effect of intestinal bacterial metabolite of ginsenosides on CYP3A activity. | 2004 Oct |
|
| Anti-inflammatory activity of 20(S)-protopanaxadiol: enhanced heme oxygenase 1 expression in RAW 264.7 cells. | 2005 Dec |
|
| Relationship between haemolytic and adjuvant activity and structure of protopanaxadiol-type saponins from the roots of Panax notoginseng. | 2005 Dec 1 |
|
| Uptake and metabolism of ginsenoside Rh2 and its aglycon protopanaxadiol by Caco-2 cells. | 2005 Feb |
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| A role for the carbohydrate portion of ginsenoside Rg3 in Na+ channel inhibition. | 2005 Feb 28 |
|
| Cyclooxygenase-2 inhibits novel ginseng metabolite-mediated apoptosis. | 2005 Mar 1 |
|
| Natural products from ginseng inhibit [3H]batrachotoxinin A 20-alpha-benzoate binding to Na+ channels in mammalian brain. | 2006 Jan 13 |
|
| Metabolite 1 of protopanaxadiol-type saponins, an axonal regenerative factor, stimulates teneurin-2 linked by PI3-kinase cascade. | 2006 Jun |
|
| Antiestrogenic effect of 20S-protopanaxadiol and its synergy with tamoxifen on breast cancer cells. | 2007 Jun 1 |
|
| Eastern blotting and immunoaffinity concentration using monoclonal antibody for ginseng saponins in the field of traditional chinese medicines. | 2007 May 16 |
|
| Anti-proliferation and apoptosis induced by a novel intestinal metabolite of ginseng saponin in human hepatocellular carcinoma cells. | 2007 Oct |
|
| [Advances in the study of ginsenoside compound K]. | 2007 Sep |
|
| 20(S)-protopanaxadiol and the ginsenoside Rh2 inhibit Na+ channel-activated depolarization and Na+ channel-dependent amino acid neurotransmitter release in synaptic fractions isolated from mammalian brain. | 2008 Apr |
|
| Protopanaxadiol 6-hydroxylase and its role in regulating the ginsenoside heterogeneity in Panax notoginseng cells. | 2008 Aug 1 |
|
| Manipulation of ginsenoside heterogeneity of Panax notoginseng cells in flask and bioreactor cultivations with addition of phenobarbital. | 2008 Feb |
|
| Comparative analysis on microbial and rat metabolism of ginsenoside Rb1 by high-performance liquid chromatography coupled with tandem mass spectrometry. | 2008 Jul |
|
| Pharmacokinetics of salvianolic acids after intravenous injection, with and without Panax quinquefolium protopanaxadiol saponins, in rats. | 2008 May 22 |
|
| Inhibitory mechanisms of dihydroginsenoside Rg3 in platelet aggregation: critical roles of ERK2 and cAMP. | 2008 Nov |
|
| 20S-protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells. | 2009 Aug |
|
| New achievements in ginseng research and its future prospects. | 2009 Dec |
|
| Compound K, a metabolite of ginseng saponin, induces apoptosis via caspase-8-dependent pathway in HL-60 human leukemia cells. | 2009 Dec 18 |
|
| Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. | 2009 Feb |
|
| Comparison of the antiobesity effects of the protopanaxadiol- and protopanaxatriol-type saponins of red ginseng. | 2009 Jan |
|
| Compound K induces apoptosis via CAMK-IV/AMPK pathways in HT-29 colon cancer cells. | 2009 Nov 25 |
|
| 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. | 2010 Dec |
|
| 20(S)-protopanaxadiol, an active ginseng metabolite, exhibits strong antidepressant-like effects in animal tests. | 2010 Dec 1 |
|
| Ginseng for cognition. | 2010 Dec 8 |
|
| Biotransformation of ginsenosides Rb1, Rg3 and Rh2 in rat gastrointestinal tracts. | 2010 May 26 |
|
| Enzymatic preparation of 20(S, R)-protopanaxadiol by transformation of 20(S, R)-Rg3 from black ginseng. | 2010 Sep |
Patents
Sample Use Guides
MDA-MB-231 breast cancer cells were used for activity evaluation. Cell viability was measured using MTT-based colorimetric assay. The cells were seeded in 96-well culture plates at 10^4 cells per well and allowed to adhere for 2 h. Thereafter, the Protopanaxadiol and/or radical donor, 1 mM AAPH, were added to culture medium, and the plates were incubated under routine conditions for 24 h. Fifty microliters of MTT (1 mg/mL) solution was added to each well. After incubation for 4 h at 37 C, the medium containing MTT was removed. The incorporated formazan crystals in the viable cells were solubilized with 100 mkL of dimethylsulfoxide. An absorbance at 540 nm of each well was then read using a SPECTRAmax 340PC
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:44:49 GMT 2023
by
admin
on
Sat Dec 16 10:44:49 GMT 2023
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| Record UNII |
P6717R7BP8
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| Record Status |
Validated (UNII)
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| Record Version |
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P6717R7BP8
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7755-01-3
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76237
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PROTOPANAXADIOL
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DTXSID301028626
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9920281
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