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
CC(C)=CCC[C@@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]3[C@@]4(C)CC[C@H](O)C(C)(C)[C@@H]4CC[C@@]23C
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 |
|---|---|---|
| (3R,6R,12R,20S,24S)-3,6,12-Triacetyl-20,24-ep-oxy-dammarane-3,6,12,25-tetra-ol. | 2010-12-11 |
|
| Ginseng for cognition. | 2010-12-08 |
|
| 20(S)-protopanaxadiol, an active ginseng metabolite, exhibits strong antidepressant-like effects in animal tests. | 2010-12-01 |
|
| 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. | 2010-12 |
|
| (3R,6R,12R,20S,24S)-20,24-Ep-oxy-dammarane-3,6,12,25-tetraol dihydrate. | 2010-11-17 |
|
| Antiobesity and antihyperglycemic effects of ginsenoside Rb1 in rats. | 2010-10 |
|
| Effects of American ginseng (Panax quinquefolius) on neurocognitive function: an acute, randomised, double-blind, placebo-controlled, crossover study. | 2010-10 |
|
| Enzymatic preparation of 20(S, R)-protopanaxadiol by transformation of 20(S, R)-Rg3 from black ginseng. | 2010-09 |
|
| Pharmacology of ginsenosides: a literature review. | 2010-06-11 |
|
| Biotransformation of ginsenosides Rb1, Rg3 and Rh2 in rat gastrointestinal tracts. | 2010-05-26 |
|
| De novo sequencing and analysis of the American ginseng root transcriptome using a GS FLX Titanium platform to discover putative genes involved in ginsenoside biosynthesis. | 2010-04-24 |
|
| [Preparation and study in vitro of 20 (S)-protopanaxadiol pharmacosomes]. | 2010-04 |
|
| Validated quantification for selective cellular uptake of ginsenosides on MCF-7 human breast cancer cells by liquid chromatography-mass spectrometry. | 2010-04 |
|
| Dietary saponins of sea cucumber alleviate orotic acid-induced fatty liver in rats via PPARalpha and SREBP-1c signaling. | 2010-03-09 |
|
| Effect of protopanaxadiol derivatives in high glucose-induced fibronectin expression in primary cultured rat mesangial cells: role of mitogen-activated protein kinases and Akt. | 2010-01 |
|
| Development of a UPLC-ESI-MS/MS assay for 20(S)-protopanaxadiol and pharmacokinetic application of its two formulations in rats. | 2010 |
|
| Compound K, a metabolite of ginseng saponin, induces apoptosis via caspase-8-dependent pathway in HL-60 human leukemia cells. | 2009-12-18 |
|
| New achievements in ginseng research and its future prospects. | 2009-12 |
|
| Compound K induces apoptosis via CAMK-IV/AMPK pathways in HT-29 colon cancer cells. | 2009-11-25 |
|
| Pharmacokinetic characterization of ginsenoside Rh2, an anticancer nutrient from ginseng, in rats and dogs. | 2009-09 |
|
| Antioxidant and apoptotic effects of korean white ginseng extracted with the same ratio of protopanaxadiol and protopanaxatriol saponins in human hepatoma HepG2 cells. | 2009-08 |
|
| Induction of chemoprotective phase 2 enzymes by ginseng and its components. | 2009-08 |
|
| 20S-protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells. | 2009-08 |
|
| [Preparation and isolation on the rare ginsenoside derivatives with anti-cancer activity]. | 2009-05 |
|
| [Determination of content and entrapment efficiency of 20 (S)-protopanaxadiol in pharmacosomes by RP-HPLC method]. | 2009-05 |
|
| Rapid and sensitive LC-MS/MS assay for the quantitation of 20(S)-protopanaxadiol in human plasma. | 2009-02-15 |
|
| Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. | 2009-02 |
|
| Comparison of the antiobesity effects of the protopanaxadiol- and protopanaxatriol-type saponins of red ginseng. | 2009-01 |
|
| Sensitive determination of 20(S)-protopanaxadiol in rat plasma using HPLC-APCI-MS: application of pharmacokinetic study in rats. | 2008-12-15 |
|
| Two new dammarane triterpene glycosides from the rhizomes of Panax notoginseng. | 2008-11-06 |
|
| Inhibitory mechanisms of dihydroginsenoside Rg3 in platelet aggregation: critical roles of ERK2 and cAMP. | 2008-11 |
|
| Protopanaxadiol 6-hydroxylase and its role in regulating the ginsenoside heterogeneity in Panax notoginseng cells. | 2008-08-01 |
|
| Enhanced inhibitory effect of ultra-fine granules of red ginseng on LPS-induced cytokine expression in the monocyte-derived macrophage THP-1 cells. | 2008-08 |
|
| Structure-activity relationship and substrate-dependent phenomena in effects of ginsenosides on activities of drug-metabolizing P450 enzymes. | 2008-07-16 |
|
| Effects of ginsenosides Re and Rg3 on intracellular redox state and cell proliferation in C6 glioma cells. | 2008-07-11 |
|
| Comparative analysis on microbial and rat metabolism of ginsenoside Rb1 by high-performance liquid chromatography coupled with tandem mass spectrometry. | 2008-07 |
|
| Biotransformation of 20(S)-protopanaxadiol by Mucor spinosus. | 2008-06-05 |
|
| Pharmacokinetics of salvianolic acids after intravenous injection, with and without Panax quinquefolium protopanaxadiol saponins, in rats. | 2008-05-22 |
|
| 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. | 2008-04 |
|
| Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra. | 2008-03 |
|
| 20(S)-25-methoxyl-dammarane-3beta, 12beta, 20-triol, a novel natural product for prostate cancer therapy: activity in vitro and in vivo and mechanisms of action. | 2008-02-26 |
|
| Manipulation of ginsenoside heterogeneity of Panax notoginseng cells in flask and bioreactor cultivations with addition of phenobarbital. | 2008-02 |
|
| Potential role of ginseng in the treatment of colorectal cancer. | 2008 |
|
| 20-O-β-d-Xylopyranos-yl(1→6)-β-d-glucopyranosyl-20(S)-protopanaxadiol methanol solvate. | 2007-12-06 |
|
| Marked production of ginsenosides Rd, F2, Rg3, and compound K by enzymatic method. | 2007-10 |
|
| Anti-proliferation and apoptosis induced by a novel intestinal metabolite of ginseng saponin in human hepatocellular carcinoma cells. | 2007-10 |
|
| [Advances in the study of ginsenoside compound K]. | 2007-09 |
|
| Antiestrogenic effect of 20S-protopanaxadiol and its synergy with tamoxifen on breast cancer cells. | 2007-06-01 |
|
| Eastern blotting and immunoaffinity concentration using monoclonal antibody for ginseng saponins in the field of traditional chinese medicines. | 2007-05-16 |
|
| Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I. | 2007-02 |
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
Mon Mar 31 23:25:13 GMT 2025
by
admin
on
Mon Mar 31 23:25:13 GMT 2025
|
| Record UNII |
P6717R7BP8
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
P6717R7BP8
Created by
admin on Mon Mar 31 23:25:13 GMT 2025 , Edited by admin on Mon Mar 31 23:25:13 GMT 2025
|
PRIMARY | |||
|
7755-01-3
Created by
admin on Mon Mar 31 23:25:13 GMT 2025 , Edited by admin on Mon Mar 31 23:25:13 GMT 2025
|
PRIMARY | |||
|
76237
Created by
admin on Mon Mar 31 23:25:13 GMT 2025 , Edited by admin on Mon Mar 31 23:25:13 GMT 2025
|
PRIMARY | |||
|
PROTOPANAXADIOL
Created by
admin on Mon Mar 31 23:25:13 GMT 2025 , Edited by admin on Mon Mar 31 23:25:13 GMT 2025
|
PRIMARY | |||
|
DTXSID301028626
Created by
admin on Mon Mar 31 23:25:13 GMT 2025 , Edited by admin on Mon Mar 31 23:25:13 GMT 2025
|
PRIMARY | |||
|
9920281
Created by
admin on Mon Mar 31 23:25:13 GMT 2025 , Edited by admin on Mon Mar 31 23:25:13 GMT 2025
|
PRIMARY |