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ギンセノシドRg3

R-Ginsenoside Rg3

HCID 46887680
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基本情報名称と識別子物性化学と産業関連反応化合物ノート
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基本情報

CAS
38243-03-7
標準SMILES
CC(C)=CCC[C@@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@]12C
InChIKey
RWXIFXNRCLMQCD-CZIWJLDFSA-N
分子式
C42H72O13
平均分子量
785.025 g/mol
単同位体質量
784.49729236

名称と識別子

優先名称
R-Ginsenoside Rg3
IUPAC
(5xi,8xi,9xi,17S,20R)-12alpha,20-Dihydroxy-14beta-lanost-24-en-3-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
現地名
ギンセノシドRg3
英語名
20(R)-Ginsenoside Rg3
分子式
C42H72O13
分子量
785.01

名称と別名

(R)-ギンセノシドRg3(20R)-3β-[[2-O-(β-D-グルコピラノシル)-β-D-グルコピラノシル]オキシ]ダンマラン-24-エン-12β,20-ジオール20(R)-メトキシジンセノシドRg3(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-2-{[(1S,3aR,3bR,5aR,7S,9aR,9bR,11R,11aR)-11-ヒドロキシ-1-[(2R)-2-ヒドロキシ-6-メチルヘプタ-5-エン-2-イル]-3a,3b,6,6,9a-ペンタメチル-ヘキサデカヒドロ-1H-シクロペンタ[a]フェナントレン-7-イル]オキシ}-4,5-ジヒドロキシ-6-(ヒドロキシメチル)オキサン-3-イル]オキシ}-6-(ヒドロキシメチル)オキサン-3,4,5-トリオール(20R)-3β-[2-O-(β-D-グルコピラノシル)-β-D-グルコピラノシルオキシ]-12β,20-ジヒドロキシダンマラ-24-エンGinsenoside Rg3 (R-Form)CID 9918693dNTP SolutionGinsenoside RgGinseonoside Rg320(r)-propanaxadiolGinsenoside Rg3 Rh2
名称をさらに表示
Ginsenosides rg3(R)Ginsenoside Rg3 (R-)20(R)-Ginsenoside Rg3

データベース識別子

物性

物理化学的性質

融点
315 · 315-318 ºC
沸点
885 · 885.0±65.0 °C(Predicted)
比重(密度)
1.3 · 1.30
貯蔵温度
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
溶解性
クロロホルム (非常にマイルド、熱超音波処理)、ピリジン (マイルド、熱、超音波処理)
外見
個体
酸解離定数(Pka)
12.85 · 12.85±0.70(Predicted)
色
ホワイトからオフホワイト
安定性
吸湿性
InChIKey
VMFHKVMQSYOBAV-KQVQOVSDNA-N

化学と産業

応用分野 · 3 件

説明Ginsenoside 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.

来歴Ginseng 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.

使用20(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.

関連反応

2 件
反応記録を作成
HRID 450955 の反応式
HRID 450955反応物としてuspto-grants-2013_07
HRID 522486 の反応式
HRID 522486反応物としてuspto-grants-2016_05

化合物ノート

読み込み中…

このページの内容基本情報名称と識別子物性化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
CAS
38243-03-7
PubChem CID
46887680
DTXSID
DTXSID40959184
ChEMBL
CHEMBL1095008
ChEBI
CHEBI:67990
UNII
U9LS0C9SWP
Nikkaji
J392.504H

上流・下流製品情報

下流製品

(20R)-5α-ダンマラ-24-エン-3α,12β,20-トリオール
補足説明 · 1 件

定義Ginsenoside 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].