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SML0184

Sigma-Aldrich

Ginsenoside Rg3

≥98% (HPLC)

Synonym(s):

(3β,12β)-12,20-Dihydroxydammar-24-en-3-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside, 20(S)-Ginsenoside-Rg3, Rg3

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About This Item

Empirical Formula (Hill Notation):
C42H72O13
CAS Number:
14197-60-5
Molecular Weight:
785.01
MDL number:
MFCD06410950
UNSPSC Code:
12352200
PubChem Substance ID:
329825213
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +10 to +20°, c = 1 in methanol

storage condition

desiccated

color

white to beige

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

C\C(C)=C\CC[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@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]4CC[C@@]23C

InChI

1S/C42H72O13/c1-21(2)10-9-14-42(8,51)22-11-16-41(7)29(22)23(45)18-27-39(5)15-13-28(38(3,4)26(39)12-17-40(27,41)6)54-37-35(33(49)31(47)25(20-44)53-37)55-36-34(50)32(48)30(46)24(19-43)52-36/h10,22-37,43-51H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37-,39-,40+,41+,42-/m0/s1

InChI key

RWXIFXNRCLMQCD-JBVRGBGGSA-N

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Application

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).
Ginsenoside Rg3 may be used in cell signaling studies.

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.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Seohyun Lee et al.
International journal of molecular sciences, 13(5), 5729-5739 (2012-07-04)
Cardiovascular disease (CVD) is one of the main causes of mortality worldwide, and dyslipidemia is a major risk factor for CVD. Ginseng has been widely used in the clinic to treat CVD. Ginsenoside Rg3, one of the major active components
Dongsun Park et al.
Environmental toxicology and pharmacology, 31(3), 397-405 (2011-07-27)
Antitumor effects of a ginsenoside Rg(3)-fortified red ginseng preparation (Rg(3)-RGP) were investigated in human non-small cell lung carcinoma (H460) cells using in vitro cytotoxicity assay and in vivo nude mouse xenograft model. Immunomodulatory effects of the preparation were also assessed
Jin-Kwang Kim et al.
Food chemistry, 141(2), 1369-1377 (2013-06-26)
The ginsenoside Rg3(S), which is one of the exceptional components of Korean red ginseng extract, has been known to have anti-cancer, anti-metastatic, and anti-obesity effects. An enzymatic bioconversion method was developed to obtain the ginsenoside Rg3(S) with a high specificity
J-P Liu et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(10), 3388-3396 (2012-07-24)
The purpose of this study is to investigate the potential subchronic toxicity of 20(S)-Ginsenoside Rg3(Rg3), by a 26-week repeated intramuscular administration in rats. Rg3 was administrated to rats at dose levels of 0, 4.2, 10.0 or 20.0 mg/kg/day. There was
Xue-Yang Pan et al.
European journal of pharmacology, 683(1-3), 27-34 (2012-03-20)
Ginsenoside Rg3 (Rg3), one of the bioactive extracts found in ginseng root, was reported to have anti-cancer activity in various cancer models. The anti-proliferation effect of Rg3 on prostate cancer cells has been well reported. To test whether Rg3 has
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