14197-60-5

Basic information

• Product Name: Ginsenoside Rg3
• Synonyms: beta-d-glucopyranoside,(3-beta,12-beta)-12,20-dihydroxydammar-24-en-3-yl2-o-b;dammar-24-ene-12-beta,20-diol,3-beta-((2-o-beta-d-glucopyranosyl-beta-d-gluc;eta-d-glucopyranosyl-;opyransoyl)oxy)-;(3beta,12beta)-12,20-dihydroxydammar-24-en-3-yl 2-o-beta-d-glucopyranosyl-beta-d-glucopyranoside;20(s)-ginsenoside-rg3;(20S)-PROPANAXADIOL;Dammar-24-ene-12β,20-diol, 3β-[(2-O-β-D-
• CAS NO: 14197-60-5
• Molecular Formula: C₄₂H₇₂O₁₃
• Molecular Weight: 785.02
• Product Categories: Saponins;The group of Ginsenosides;Ginsenoside series;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 14197-60-5.mol

Chemical Properties

• Melting Point: 315-318°C
• Boiling Point: 885.017 °C at 760 mmHg
• Flash Point: 489.041 °C
• Appearance: white to beige/
• Density: 1.30
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥5mg/mL
• PKA: 12.85±0.70(Predicted)
• CAS DataBase Reference: Ginsenoside Rg3(CAS DataBase Reference)
• NIST Chemistry Reference: Ginsenoside Rg3(14197-60-5)
• EPA Substance Registry System: Ginsenoside Rg3(14197-60-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: LY9537300
• Hazardous Substances Data: 14197-60-5(Hazardous Substances Data)

Usage

Uses

Used in Cardiology:
Ginsenoside Rg3 is used as a modulatory agent for delayed rectifier potassium current (IKr) channels in long QT syndrome (LQTS) human induced pluripotent stem cells (hiPSC-CMs). This application aims to investigate its potential effects on cardiac ion channels, which could be beneficial for patients with LQTS.
Used in Oncology:
Ginsenoside Rg3 is used as an anti-tumor agent, demonstrating a synergistic antitumor effect with cisplatin in cisplatin-resistant bladder tumor cell lines. Its ability to induce apoptosis and inhibit angiogenesis in a variety of cancer models makes it a promising candidate for cancer treatment and a potential enhancer of chemo-sensitivity in resistant cases.

Biochem/physiol Actions

Ginsenoside Rg3 is a natural product isolated from Panax ginseng. Similar to other ginsenosides it exhibits cardio protective effects. Ginsenoside Rg3 enhances cardiac, hERG (IKr) and KCNQ (Iks), channel currents by interaction with the channel pore entryway. It also inhibits the palmitate-induced apoptosis of MIN6N8 mouse insulinoma beta-cells through modulating p44/42 MAPK activation. Ginsenoside Rg3 increases the level of the transcription factor Nrf2 and induces the mRNA levels of multidrug resistance-associated protein (Mrp) 1 and Mrp3. Rg3 modulate neuroinflammation by attenuating the activation of microglia in response to systemic LPS treatment. It activates AMPK in HepG2 cells and reduces the lipid accumulation thereby decreasing the risk of cardiovascular disease due to dyslipidemia.

Upstream product

• 126149-74-4 C₄₆H₇₆O₁₆ 
• 88156-44-9 malonyl-ginsenoside Rb₂ 
• 88140-36-7 malonyl-ginsenoside Rc 
• 88140-43-6 C₅₇H₉₄O₂₅ 
• 88140-35-6 C₅₇H₉₄O₂₅ 
• 88140-34-5 malonyl-ginsenoside Rb₁ 
• 88140-38-9 C₅₈H₉₆O₂₆ 
• 51116-90-6 12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one 
• 127750-92-9 12β-acethoxy-3β,20S-dihydroxydammar-24-ene 
• 41753-43-9 Ginsenoside Rb₁ 
• 52705-93-8 ginsenoside Rd 
• 127750-93-0 12-O-acetyl-dammar-24-ene-12β,20(S)-diol-3-one 
• 6892-79-1 (20S)-dammar-24-ene-3α,12β,20-triol 

Downstream Products

• 6892-79-1 protopanaxadiol 
• 67400-17-3 ginsenoside Rh₂ 
• 194861-70-6 ginsenoside Rs3 

Relevant articles and documents

The preparation of ginsenoside Rg5, its antitumor activity against breast cancer cells and its targeting of PI3K

Ginsenosides have been reported to possess various pharmacological effects, including anticancer effects. Nevertheless, there are few reports about the antitumor activity and mechanisms of ginsenoside Rg5 against breast cancer cells. In the present study, the major ginsenoside Rb1 was transformed into the rare ginsenoside Rg5 through enzymatic bioconversion and successive acid-assisted high temperature and pressure processing. Ginsenosides Rb1, Rg3, and Rg5 were investigated for their antitumor effects against five human cancer cell lines via the MTT assay. Among them, Rg5 exhibited the greatest cytotoxicity against breast cancer. Moreover, Rg5 remarkably suppressed breast cancer cell proliferation through mitochondria-mediated apoptosis and autophagic cell death. LC3B-GFP/Lysotracker and mRFP-EGFP-LC3B were utilized to show that Rg5 induced autophagosome-lysosome fusion. Western blot assays further illustrated that Rg5 decreased the phosphorylation levels of PI3K, Akt, mTOR, and Bad and suppressed the PI3K/Akt signaling pathway in breast cancer. Moreover, Rg5-induced apoptosis and autophagy could be dramatically strengthened by the PI3K/Akt inhibitor LY294002. Finally, a molecular docking study demonstrated that Rg5 could bind to the active pocket of PI3K. Collectively, our results revealed that Rg5 could be a potential therapeutic agent for breast cancer treatment.

Manufacturing method for mass-production of 20(S)-ginsenoside Rg3

The present invention relates to a method for selectively mass-producing 20(S)-ginsenoside Rg3 from ginsenoside Rd. The 20(S)-ginsenoside Rg3 rarely exists in white ginseng or red ginseng, and exists as an S-type isomer or an R-type isomer even though exiting in a small amount. Thus, an amount thereof refined as a single material is very low, and thus a use thereof is not easy. However, according to the present invention, 20(S)-ginsenoside Rg3 is mass-produced by using only ginsenoside Rd which can be easily separated from leaves of ginsengs, and thus addition of ginsenoside which may be generated from Rc, Re, Rf, and the like can be relatively prevented compared to when extracts of ginsengs, red ginsengs, or the like are used. A relative production amount of 20(R)-ginsenoside Rg3 is low. Thus, purification is easy, and mass-production is easy.(AA) Before steaming(BB) Example 1-1 (dry steaming, 120 anddeg;C, 2 hours, 0.13MPa)(CC) Example 1-2 (dry steaming, 120 anddeg;C, 4 hours, 0.13MPa)(DD) Example 1-3 (dry steaming, 120 anddeg;C, 6hours, 0.13MPa)COPYRIGHT KIPO 2018

Conversion of ginsenoside RB1 into six types of highly bioactive ginsenoside Rg3 and its derivatives by FeCl3 catalysis

Ginsenoside Rb1 is an important saponin of ginseng(s); however, Rb1, with 3-O- and 20-O-sugar moieties, has low bioavailability. Here, we report the derivatization of ginsenoside Rb1 to completely generate six types of highly bioactive minor ginsenoside R

Microwave degradation of floatation-enriched ginsenoside extract from Panax quinquefolium L. Leaf

Even though the degradation of ginsenosides has been thoroughly studied in animals and in vitro using acids, enzymes, and intestinal bacteria, a new degradation method is established for obtaining the ginsenosides Rg3, Rh2 and their

The chemical and hydroxyl radical scavenging activity changes of ginsenoside-Rb1 by heat processing

The chemical and hydroxyl radical ({radical dot}OH) scavenging activity changes of ginsenoside Rb1 (Rb1) by heat processing were investigated in this study. Rb1 was changed into 20(S)-Rg3, 20(R)-Rg3,

Metabolism of 20(S)- and 20(R)-ginsenoside Rg3 by human intestinal bacteria and its relation to in vitro biological activities.

When ginsenoside Rg3 was anaerobically incubated with human fecal microflora, all specimens metabolized ginsenoside Rg3 to ginsenoside Rh2 and protopanaxadiol. The main metabolite was ginsenoside Rh2. 20(S)-ginsenoside Rg3 was quickly transformed to 20(S)

Synthesis of ginsenoside Rg3, a minor constituent of Ginseng radix.

Glycosylation of 12beta-acetoxy-dammar-24-en-3beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha- and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg3, the minor component of Ginseng Radix rubra. All compounds were fully characterized by 1H and 13C NMR spectroscopy.