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20(R)-Ginsenoside Rg3

HCID 181573
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Grundinformationen

CAS
38243-03-7
Standard-SMILES
CC(C)=CCC[C@@](C)(O)[C@H]1CC[C@]2(C)C3CCC4C(C)(C)C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)C3C[C@H](O)[C@]12C
Summenformel
C42H72O13
Durchschnittliche Molmasse
785,01 g/mol

Namen und Bezeichner

Bevorzugter Name
20(R)-Ginsenoside Rg3
Englischer Name
20(R)-Ginsenoside Rg3
Summenformel
C42H72O13
Molmasse
785.01

Namen und Synonyme

Ginsenoside Rg3 (R-Form)CID 9918693dNTP SolutionGinsenoside RgGinseonoside Rg320(r)-propanaxadiolGinsenoside Rg3 Rh2Ginsenosides rg3(R)Ginsenoside Rg3 (R-)20(R)-Ginsenoside Rg3

Datenbank-Bezeichner

CAS
38243-03-7
PubChem CID
181573

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
315 · 315-318 ºC
Siedepunkt
885 · 885.0±65.0 °C(Predicted)
Dichte
1.3 · 1.30
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit
Chloroform (Very Slightly, Heated Sonicated), Pyridine (Slightly, Heated, Sonicated)
Aggregatzustand
Solid
pka
12.85 · 12.85±0.70(Predicted)
Farbe
White to Off-White
Stabilität
Hygroscopic
InChIKey
VMFHKVMQSYOBAV-KQVQOVSDNA-N

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungGinsenoside Rg3 is mainly derived from the dried roots of Araliaceae Panax ginseng C.A.Mey. and Panax quinquefolius L.Ginseng has a long history of medicinal uses, well known as “king of herbs.” Ginseng is listed as the top grade in “Shen Nong’s herbal class,” with “the main security set up the five internal organs, spirit, soul, stop fright, in addition to evil, eyesight, fun puzzle” account. The traditional Chinese medicine regards ginseng as the top grade of reinforcing Qi, with Dabu strength, spleen and lungs, Sheng Jin, Anshen Yizhi, etc.

HistoryGinseng is currently one of the most studied traditional medicines. Chemical researches certificate that ginseng contains a variety of ginseng saponin, ginseng polysaccharide, protein, polypeptide, amino acids, and other chemical constituents. Ginseng saponins are the main active components, accounting for about 4%. Ginsenoside is a kind of sterol compound, which has a similar basic structure. Ginsenoside contains the steroid nucleus of 17 carbon atoms arranged in 4 rings. At present, more than 40 kinds of ginsenosides have been isolated from ginseng. They are divided into four types according to their chemical structure, the protopanaxadiol, the protopanaxatriol, the ocotillol, and the oleanolic acid.Ginsenoside Rg3 is a dammarane tetracyclic triterpenoid saponin found in natural ginseng, which belongs to the protopanaxadiol . It is also the natural ingredient with prominent activity extracted from red ginseng (processed ginseng). Modern medicine has proved that Rg3 has certain biological activity. Since 1983, Rg3 has been widely studied by many scholars in the world . The results showed that the content of ginsenoside Rg3 in the fresh and dried ginseng roots was less than 1 ppm while in red ginseng was 3/100,000. After several years of research, the method of extracting 20(R)-ginsenoside Rg3 from red ginseng has been successfully improved, and the industrialized production has been realized. A multicenter clinical study by eight domestic hospitals indicated that 20(R)-ginsenoside Rg3 has therapeutic effects on tumor. It has been issued the new drug certificate by the Chinese Food and Drug Administration, as a new anticancer drug approved.

Verwenden20(R)-Ginsenoside Rg3 causes an inhibition of phosphatidylinositol 3-kinase/Akt activation that, in turn, results in modulations in Bcl-2 family proteins in such a way that the apoptosis of U87 cells are regulated. Elicits a significant inhibition of in vitro cell adhesion and invasion of U87 cells. in vitro stereoselective inhibition of ginsenosides toward UDP-glucuronosyltransferase isoforms and in vivo inhibition of tumor angiogenesis of lung cancer.

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Ergänzende Hinweise · 1 Eintrag

DefinitionGinsenoside Rg3 is a tetracyclic triterpenoid saponin type rich in red ginseng. The major ginsenosides, such as Rb1, Rb2, and Rg3. Due to the different spatial structures from C20 positions, there are two enantiomers, 20(R) and 20(S)-isomers. With differential conguration, their antitumor activities exhibit certain differences. 20(R)-ginsenoside Rg3 and 20(S)-ginsenoside Rg3 can inhibit tumor metastasis by the suppression of EMT. 20(R)-ginsenoside Rg3 suppressed lung cancer migration or/and invasion by inhib-iting TGF-β1-induced EMT accompanied by the inactivation of MMP-2, p38 MAPK and Smad2. In addition, 20(S)-ginsenoside Rg3 effectively suppressed hypoxia-induced EMT, inhibiting ovarian cancer metastasis[1].