(20S)-Protopanaxadiol

Catalog No.S4746 Synonyms: 20-Epiprotopanaxadiol

For research use only.

20(S)-Protopanaxadiol (PPD, 20-Epiprotopanaxadiol), the main intestinal metabolite of ginsenosides, is one of the active ingredients in ginseng. 20(S)-Protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells.

(20S)-Protopanaxadiol Chemical Structure

CAS No. 30636-90-9

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Biological Activity

Description 20(S)-Protopanaxadiol (PPD, 20-Epiprotopanaxadiol), the main intestinal metabolite of ginsenosides, is one of the active ingredients in ginseng. 20(S)-Protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells.
In vitro

Concentrations causing growth inhibition of 50% of cells (LC50) for the compounds PPD is 23 μg/ml, for Int-407 cells. The the LC50 for PPD is determined to be 24 μg/ml in Caco-2 cells. In the Int-407 cell line, PPD produces great percentage of sub-G1 (apoptotic) cells(The Int-407 cell line is a human embryonic nonmalignant cell line originating from fetal tissue of approximately 2 months gestation, whereas Caco-2 is a human colon adenocarcinoma cell line). This response is attributed to differences in individual ginsenoside glycosylation and, thus, the hydrophobic-hydrophilic balance [2]. Incubation with PPD also significantly reduces the viability of U251-MG and U87-MG cells in a dose- and time-dependent manner. The cytotoxic effect of PPD is accompanied by reduced expression of cell adhesion proteins, including N-cadherin and integrin β1, which leads to reduced phosphorylation of focal adhesion kinase. Furthermore, incubation with PPD reduces the expression of cyclin D1 and subsequently induces cell-cycle arrest at the G1 phase[3].

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
SF188 cells M3jlNWN6fG:2b4jpZ4l1gSCjc4PhfS=> MkjHNlQhcA>? MUTDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDTSlE5QCClZXzsd{Bi\nSncjCyOEBpenN? MXKxO|I3OTB4Nx?=
U87MG cells NFHXPJFEgXSxdH;4bYNqfHliYYPzZZk> NIrmeIkzPCCq MoHSR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gWVg4VUdiY3XscJMh[W[2ZYKgNlQhcHK| NHnBZZQyPzJ4MUC2Oy=>
U87MG cells M4XpUWZ2dmO2aX;uJIF{e2G7 NV;yW401OiCq MmDzTY5kemWjc3WgbY4he3WyZYLvfIll\SCjbnnvckBt\X[nbDDpckBpfW2jbjDVPFdOTyClZXzsd{Bi\nSncjCyJIhzew>? NFvCXIEyPzJ4MUC2Oy=>
U87MG cells MVLGeY5kfGmxbjDhd5NigQ>? M2HnT|Q{NjRizszN MWG0JIg> MXfJcoR2[3Srb36gc4Yh[XW2b4DoZYd6KGmwIHj1cYFvKFV6N13HJINmdGy|IHL5JG1FSyC|dHHpcolv\yCjdDC0N{41KHWPIHHmeIVzKDRiaILz NUHXRnl5OTd{NkGwOlc>
U87 cell NE\BRo9EgXSxdH;4bYNqfHliYYPzZZk> MV:3NkBp M1W0VmN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJHU5PyClZXzsd{Bi\nSncjC3NkBpenNiYomgUXRVKGG|c3H5 NGf1V2EzOjN2MkGwNS=>
Hep3B cells M2PiV2N6fG:2b4jpZ4l1gSCjc4PhfS=> Mm\pO|IhcA>? NID4[nVEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJ\XB|QjDj[YxteyCjZoTldkA4OiCqcoOgZpkhVVSWIHHzd4F6 Ml[wNlI{PDJzMEG=
MDA-MB-231 cells Mo\xSpVv[3Srb36gZZN{[Xl? MXeyMlUuPS56IN88US=> MWqyOEBp M3rkfmlv\HWldHnvckBw\iCjcH;weI9{cXNiaX6gbJVu[W5iTVTBMW1DNTJ|MTDj[YxteyCjc4Pld5Nm\CCjczDpcoNz\WG|ZTDpckBmgHC{ZYPzbY9vKG:oIHPs[YF3\WRiUFHSVEBifCB{LkWgeI8hPS56IIXNJIFnfGW{IEK0JIhzeyCkeTDTSHMueG:ueXHjeJlt[W2rZHWg[4VtKGWuZXP0do9xcG:{ZYPpdy=> MUWyOVQ2Ozd7OB?=
LLC-PK1 NIfqd|FEgXSxdH;4bYNqfHliYYPzZZk> MW[0JIg> MYfDfZRwfG:6aXPpeJkh[WejaX7zeEBxcWdiTFzDMXBMOSClZXzsd{Bi\nSncjC0JIhzeyCkeTDNWHQh[XO|YYm= NHz1WGIzPTR3M{e5PC=>
MDA-MB-231 cells M{C4NXBzd2yrZnXyZZRqd25iYYPzZZk> M1TCeFQhcA>? NFvncmZCdnSrcILvcIln\XKjdHn2[UBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIF3ERU1OSi1{M{GgZ4VtdHNiYX\0[ZIhPCCqcoOgZpkhVVSWIHHzd4F6 MXeyOVQ2Ozd7OB?=
COLO205 cells NIrjc4lEgXSxdH;4bYNqfHliYYPzZZk> Mn32O|IhcA>? NUDVcVF6S3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hS0:OT{KwOUBk\WyuczDh[pRmeiB5MjDodpMh[nliTWTUJIF{e2G7 NX;0OI9jOjF{MU[xOFU>
HL60 cells NFfzdHdEgXSxdH;4bYNqfHliYYPzZZk> NEn2WJE4OiCq M1myWmN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGhNPjBiY3XscJMh[W[2ZYKgO|IhcHK|IHL5JG1VXCCjc4PhfS=> NHHtVYYzOTJzNkG0OS=>
HepG2 cells MkPvR5l1d3SxeHnjbZR6KGG|c3H5 NUf2R3VXPzJiaB?= M3i2OWN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGhmeEd{IHPlcIx{KGGodHXyJFczKGi{czDifUBOXFRiYYPzZZk> MlrxNlEzOTZzNEW=
MCF7 cells MnvNR5l1d3SxeHnjbZR6KGG|c3H5 MWO3NkBp MYLDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDNR2Y4KGOnbHzzJIFnfGW{IEeyJIhzeyCkeTDNWHQh[XO|YYm= MkjTNlEzOTZzNEW=
SF188 cells MlKySpVv[3Srb36gZZN{[Xl? NEnON4MyODhwNDFOwG0> NHvNXlg1KGh? MXTJcoR2[3Srb36gc4Yh[XW2b4DoZYd6KGmwIHj1cYFvKFOIMUi4JINmdGy|IHL5JG1FSyC|dHHpcolv\yCjdDCxNFgvPCC3TTDh[pRmeiB2IHjydy=> NVfqS|NuOTd{NkGwOlc>
SF188 cells NILzW4NHfW6ldHnvckBie3OjeR?= NXfIXYR6OTB6LkSg{txO MWXBZ5RqfmG2aX;uJI9nKGOjc4Dhd4UhOyCrbjDoeY1idiCVRkG4PEBk\WyuczDheEAyODhwNDD1US=> M3m3cFE4OjZzME[3
SF188 cells NWPiS4FKTnWwY4Tpc44h[XO|YYm= MWKyJIg> NVf3dHlwUW6lcnXhd4UhcW5ic4Xw[ZJwgGmmZTDhcolwdiCuZY\lcEBqdiCqdX3hckBUTjF6ODDj[YxteyCjZoTldkAzKGi{cx?= NWDhZ4d1OTd{NkGwOlc>
SF188 cells NU\ieVZoTnWwY4Tpc44h[XO|YYm= NGX0cZkyODhwNDFOwG0> MlfpRYN1cX[jdHnvckBw\iClYYPwZZNmKDdiaX6gbJVu[W5iU1[xPFgh[2WubIOgZZQhOTB6LkSgeW0> MmXRNVczPjFyNke=
SF188 cells MoPUSpVv[3Srb36gZZN{[Xl? NYrMWnlWPDNwNDFOwG0> MWS0JIg> NWD0cY5OUW6mdXP0bY9vKG:oIHH1eI9xcGGpeTDpckBpfW2jbjDTSlE5QCClZXzsd{BjgSCPRFOgd5RicW6rbnegZZQhPDNwNDD1UUBi\nSncjC0JIhzew>? NXewU2dxOTd{NkGwOlc>
HepG2 cells MYLDfZRwfG:6aXPpeJkh[XO|YYm= NW[xUnV3PDhiaB?= Mn6wR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gTIVxTzJiY3XscJMh[W[2ZYKgOFghcHK|IHL5JG1VXCCjc4PhfS=> Mlq3NlY1OjByNke=
HL60 cells NIf5WnREgXSxdH;4bYNqfHliYYPzZZk> NV;lTnZvPDhiaB?= MVnDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDIUFYxKGOnbHzzJIFnfGW{IES4JIhzeyCkeTDNWHQh[XO|YYm= NF2wTZAzPjR{MEC2Oy=>
In vivo

Treatment with PPD(20(S)-Protopanaxadiol) and PPT(20(S)-Protopanaxatriol) prior to immobilization stress increase the time spent in open arms and open arm entries in the elevated plus-maze (EPM) test. Treatment with PPD potently suppresses immobilization stress-induced serum levels of corticosterone and interleukin (IL)-6 by the enzyme-linked immunosorbent assay. PPD and PPT may exhibit the anxiolytic effect via γ-aminobutyrateA (GABAA) receptor(s) and serotonergic receptor(s), respectively, and PPD may have an anti-inflammatory effect that is more potent than that of PPT[1].

Protocol (from reference)

Cell Research:

[2]

  • Cell lines: Int-407 and Caco-2 cell lines
  • Concentrations: 23 μg/ml(Int-407 cells); 24 µg/mL(Caco-2 cells)
  • Incubation Time: 24, 48, 72 h
  • Method:

    Int-407 and Caco-2 cells are seeded at a concentration of 1×106 cells/mL in 24-well plates in separate experiments. Test ginsenosides (PPD, PPT, Rh2) are added to wells to the LC50 concentration determined previously from the MTT assays. The ginsenoside concentrations used for Int-407 cells are 23, 26, and 53 µg/mL, respectively, for PPD, PPT, and Rh2. In a similar experiment using Caco-2 cells, 24 µg/mL for both PPD and PPT and 55 µg/mL for Rh2 is used. Untreated cells represented the control. Cells are incubated at 37℃ in a 5% CO2 humidified incubator for 24, 48, and 72 h. Cell-free supernatant are obtained by centrifugation(400g) for 10 min, and the lactate dehydrogenase (LDH) assay is conducted as previously reported.

  • (Only for Reference)
Animal Research:

[1]

  • Animal Models: Male ICR mice
  • Dosages: 5 or 10 mg/kg
  • Administration: p.o.
  • (Only for Reference)

Solubility (25°C)

In vitro

DMSO 92 mg/mL
(199.68 mM)
Ethanol 33 mg/mL
(71.62 mM)
Water Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 460.73
Formula

C30H52O3

CAS No. 30636-90-9
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)O)C

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