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Protopanaxdiol

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-P1014

  • Specification : 98%

  • CAS number : 30636-90-9

  • Formula : C30H52O3

  • Molecular Weight : 460.73208

  • PUBCHEM ID : 11213350

  • Volume : 20mg

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Catalogue Number

BF-P1014

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

460.73208

Appearance

White crystalline powder

Botanical Source

Panax ginseng,Panax notoginseng

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)O)C

Synonyms

Protopanaxadiol/Protopanaxtriol/(20S)-Protopanaxadiol/20(S)-Protopanaxdiol/(3β,12β)-Dammar-24-ene-3,12,20-triol/PROTOPANAXDIOL/Dammar-24-ene-3,12,20-triol, (3β,12β)-/Protopanaxadiol, 20S-

IUPAC Name

(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol

Density

1.0±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate; Acetone

Flash Point

226.1±21.9 °C

Boiling Point

559.5±40.0 °C at 760 mmHg

Melting Point

InChl

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

InChl Key

PYXFVCFISTUSOO-HKUCOEKDSA-N

WGK Germany

RID/ADR

HS Code Reference

2906190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:30636-90-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31805304

Abstract

20(S)-Protopanaxadiol [20(S)-PPD], one of the metabolites of ginsenosides, was investigated to determine its potential mechanism for targeting to epidermal growth factor receptor (EGFR) pathway in lung cancer cell A549. Results of kinase inhibitory assay showed that 20(S)-PPD was an EGFR tyrosine kinase inhibitor. By binding to EGFR, 20(S)-PPD disrupted the EGFR/MAPK signaling. The expression of genes in the pathway was altered and the upregulation of Ras and MEK1 was extremely notable. The accumulation and phosphorylation of EGFR, Ras, BRAF, Raf-1, MEK, and ERK were variously altered. The above alteration subsequently resulted in cell cycle arrest. 20(S)-PPD interfered the cell cycle regulation network and eventually blocked cell cycle progression at G0/G1 phase, which may be the key reason for proliferation inhibition. Although some apoptosis related genes and proteins were influenced, apoptosis was not the main reason for proliferation inhibition. The cell wound healing assay confirmed that the inhibition of 20(S)-PPD to A549 cells could suppress the migration and invasion thereof. The results of molecular docking and molecular dynamics simulation provide a possible interaction mechanism between EGFR and 20(S)-PPD. The results described above suggested that 20(S)-PPD could block cell cycle progression by targeting the EGFR/MAPK signaling pathway.

Copyright © 2019 Elsevier Ltd. All rights reserved.

KEYWORDS

20(S)-Protopanaxadiol; Cell cycle; Epidermal growth factor receptor; Interaction mechanism

Title

20(S)-Protopanaxadiol blocks cell cycle progression by targeting epidermal growth factor receptor.

Author

Zhang T1, Liang Y1, Zuo P2, Jing S1, Li T2, Wang Y2, Lv C2, Li D2, Zhang J3, Wei Z4.

Publish date

2020 Jan

PMID

31749618

Abstract

BACKGROUND:
20(S)-Protopanaxadiol (PPD) has a higher anti-wrinkle effect than the other glycone forms of ginsenosides. However, as PPD has low solubility in water and a high molecular weight, it cannot easily penetrate the stratum corneum layer, which is the rate-limiting step of topical skin delivery. Thus, the objective was to enhance the topical skin deposition of PPD using an optimized nanostructured lipid carriers (NLC) formulation. NLC formulations were optimized using a Box-Behnken design.

MATERIALS AND METHODS:
NLC formulations were optimized using a Box-Behnken design, where the amount of PDD (X1), volume of the liquid lipid (X2), and amount of surfactant (X3) were set as the independent variables, while the particle size (Y1), polydispersity index (PDI) (Y2), and entrapment efficiency (EE) (Y3) were dependent factors. An in vitro deposition study was performed using Strat-M® and human cadaver skin, while in vivo skin irritation effect of the NLC formulation was evaluated in humans.

RESULTS:
An NLC was successfully prepared based on the optimized formulation determined using the Box-Behnken design. The particle size, PDI, and EE of the NLC showed less than 5% difference from the predicted values. The in vitro deposition of PPD after the application of the NLC formulation on a Strat-M® artificial membrane and human cadaver skin was significantly higher than that of the controls. Moreover, NLC formulations with and without PDD were not skin irritants in a human study.

CONCLUSION:
An NLC formulation for the topical delivery of PPD was successfully optimized using the Box-Behnken design, and could be further developed to enhance the topical skin deposition of PPD.

© 2019 Kim et al.

KEYWORDS

20(S)-Protopanaxadiol; Box-Behnken design; Strat-M™; nanostructured lipid carrier; NLC; topical delivery

Title

Formulation And Evaluation Of Nanostructured Lipid Carriers (NLCs) Of 20(S)-Protopanaxadiol (PPD) By Box-Behnken Design.

Author

Kim MH1, Kim KT2, Sohn SY1, Lee JY3, Lee CH4, Yang H4, Lee BK5, Lee KW4,5, Kim DD1.

Publish date

2019 Oct 25;

PMID

31506831

Abstract

The aim of this study was to prepare a 20(S)-protopanaxadiol nanocrystalline suspension and enhance the bioavailability of 20(S)-protopanaxadiol by intramuscular injection. 20(S)-Protopanaxadiol nanocrystalline suspension was prepared using an anti-solvent combined with ultrasonic approach, in which meglumine and bovine serum albumin were screened as the optimized stabilizer and the coating agent during spray drying process, respectively. The optimal nanocrystallines were nearly spherical with a uniform particle size distribution, the mean particle size, polydispersity index, and drug loading of which were 151.20 ± 2.54 nm, 0.11 ± 0.01, and 47.15% (w/w), respectively. Sterile 20(S)-protopanaxadiol nanocrystalline suspension was obtained by passing through a 0.22-μm membrane, and the average filtration efficiency (FE%) was 99.96%. The cumulative release percentage of 20(S)-protopanaxadiol nanocrystalline suspension was 92.36% 20(S)-protopanaxadiol within 60 min in vitro, which was relatively rapid compared with that of the physical mixture for 12.51% and the 20(S)-protopanaxadiol bulk powder for 9.71% during the same time interval. The sterile 20(S)-protopanaxadiol nanocrystalline suspension caused minimal irritation responses by histological examination, indicating a good biocompatibility between the 20(S)-protopanaxadiol nanocrystalline suspension and muscle tissues. In pharmacokinetic study, the absolute bioavailability of 20(S)-protopanaxadiol nanocrystalline suspension for intramuscular injection and for oral gavage was 5.99 and 0.03, respectively. In summary, the 20(S)-protopanaxadiol nanocrystalline via intramuscular injection is an efficient drug delivery system to improve its bioavailability.

KEYWORDS

bioavailability; biocompatibility; intramuscular injection; nanocrystallines; oral gavage

Title

Enhanced the Bioavailability of Sterile 20(S)-Protopanaxadiol Nanocrystalline Suspension Coated by Bovine Serum Albumin for Intramuscular Injection: In Vitro and In Vivo Evaluation.

Author

Zhang H1, Liu H1, Qi P1, Wang S2, Hu H3, Gou J1, Zhang Y1, He H1, Tang X1, Yin T4,5, Yuan Y6.

Publish date

2019 Sep 10;


Description :

(20S)-Protopanaxadiol (20-Epiprotopanaxadiol) is an aglycon metabolic derivative of the protopanaxadiol-type ginseng saponin; apoptosis inducer.IC50 value:Target: apoptosis inducer(20S)-Protopanaxadiol was used to induce cytotoxicity for two human glioma cell lines, SF188 and U87MG. For the SF188 cells, (20S)-Protopanaxadiol activated caspases-3, -8, -7, and -9 within 3 h and induced rapid apoptosis, which could be partially inhibited by a general caspase blocker and completely abolished when the caspase blocker was used in combination with an antioxidant. (20S)-Protopanaxadiol also induced cell death in U87MG cells but did not activate any caspases in these cells [1]. aPPD was able to inhibit P-gp activity as potently as verapamil on MDR cells. The blockage of P-gp activity was highly reversible as wash-out of aPPD resulted in an immediate recovery of P-gp activity. Unlike verapamil, aPPD did not affect ATPase activity of P-gp suggesting a different mechanism of action [2].