Ginsenoside Rg3

Description

Ginsenosides are pharmacologically active natural constituents of ginseng and other plants of the genus Panax. Structurally, they are steroid glycosides derived from the triterpene squalene. Ginsenoside Rg₃ is a panaxadiol found in white and red P. ginseng. This ginsenoside has diverse in vitro and in vivo effects, including anti-cancer, neuroprotective, anti-hypertensive, and anti-inflammatory actions. Ginsenoside Rg₃ induces apoptosis and inhibits angiogenesis in a variety of cancer models. Notably, this ginsenoside can be produced by heating other ginsenosides, leading to elevated levels in steamed or dried ginseng preparations.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from ginseng.

Uses

Ginsenoside Rg3 has been used to investigate its modulatory effects on delayed rectifier potassium current (IKr) channels in long QT syndrome (LQTS)2-human induced pluripotent stem cells (hiPSC-CMs).

Uses

Ginsenoside Rg3 shows a synergistic antitumor effect with cisplatin in cisplatin-resistant bladder tumor cell lines and is considered to be an anti-tumor agent.

Definition

ChEBI: (20S)-ginsenoside Rg3 is a ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranosyl-beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position. It has a role as an apoptosis inducer, an antineoplastic agent, a plant metabolite and an angiogenesis modulating agent. It is a ginsenoside, a tetracyclic triterpenoid and a glycoside. It is functionally related to a (20S)-protopanaxadiol. It derives from a hydride of a dammarane.

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.

Synthesis

52705-93-8

38243-03-7

14197-60-5

1. Accurately weigh 10 mg of ginsenoside Rd and dispense into five 2 mL cold sterile vials and seal (using screw plugs and silica gel rings). 2. Place the vials containing the sample in a 125 ml glass bottle. 3. Place the above glass vials in a sterilizer (SANYO autoclave, model MLS-3780) and steam treat at 120°C for 2 hours at a pressure of 0.13-0.15 MPa. 4. After 2 hours, one of the samples was removed and the rest of the samples were continued to be steam treated under the same temperature and pressure conditions. 5. The above steps were repeated and the samples were removed at 2 h, 4 h, 6 h, 8 h and 10 h to obtain the treatment products at different time points. 6. Ginsenosides Rd, Rg3-S and Rg3-R were analyzed using HPLC and the results were recorded in Table 2.

in vivo

IC 50

Na⁺ channel: 32.2 μM (IC₅₀); hKv1.4 channel: 32.6 μM (IC₅₀); p65; COX-2; Aβ40; Aβ42

References

[1] Patent: KR2018/76498, 2018, A. Location in patent: Paragraph 0029; 0031-0043