34367-04-9 , Ginsenoside Ro ,
Chikusetsusaponin;
Polysciasaponin P3 ,
(3b)-28-(b-D-Glucopyranosyloxy)-28-oxoolean-12-en-3-yl 2-O-(b-D-glucopyranosyl)-b-D-glucopyranosiduronic acid;
Cas:34367-04-9
C48H76O19 / 957.13
MFCD01732056
(3b)-28-(b-D-Glucopyranosyloxy)-28-oxoolean-12-en-3-yl 2-O-(b-D-glucopyranosyl)-b-D-glucopyranosiduronic acid;
Ginsenoside Ro is a non-steroid glycoside that has been found in plants of the genus Panax and has anti-inflammatory, antithrombotic, and antiviral biological activities. It inhibits LPS-induced release of reactive oxygen species (ROS) and nitric oxide (NO) as well as inducible nitric oxide synthase (iNOS) and COX-2 protein expression in RAW 264.7 murine macrophages when used at a concentration of 200 μM. Ginsenoside Ro dose-dependently inhibits human platelet aggregation induced by thrombin in vitro and thrombin-induced disseminated intravascular coagulation (DIC) in rats when administered at a dose of 100 mg/kg. It increases the 20-day survival of Sendai virus-infected mice when administered at a dose of 1 mg per day for three days prior to infection. Topical administration of ginsenoside Ro (0.2 mg per animal) also stimulates hair regrowth after shaving in a mouse model of slowed hair regrowth.
Ginsenoside Ro is an oleanane-type saponin, a natural anionic biosurfactant extracted from Panax ginseng which is of high research interest due to its anti-inflammatory, anti-platelet, anticomplementary and immunomodulatory properties. It is also a health promoter and the most widely used dietary supplement.
Ginsenoside ro belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b, 19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Ginsenoside ro exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, ginsenoside ro is primarily located in the cytoplasm and membrane (predicted from logP). Outside of the human body, ginsenoside ro can be found in tea. This makes ginsenoside ro a potential biomarker for the consumption of this food product.
Ginsenoside Ro is a ligustilide glycoside that is found in the roots of the plant Fructus Ligustri. It has been shown to inhibit P-glycoprotein and to have an effect on energy metabolism and neuronal death. Ginsenoside Ro has also been shown to have a matrix effect, which means that it can cross the blood-brain barrier. This compound has been shown to reduce postprandial blood glucose levels in rats and may be useful for treating bowel disease. The analytical method for ginsenoside Ro involves high-performance liquid chromatography (HPLC) with ultraviolet detection at 210 nm. The molecular weight of this compound is 414.3 Da and its chemical formula is C24H34O7. Ginsenoside Ro binds to bcl-2 protein, inhibiting apoptosis in cells by preventing caspase activation, thus maintaining the cell's viability.
CAS Number | 34367-04-9 |
Product Name | Ginsenoside Ro |
IUPAC Name | (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-Heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid |
Molecular Formula | C48H76O19 |
Molecular Weight | 957.13 g/mol |
InChI | InChI=1S/C48H76O19/c1-43(2)14-16-48(42(61)67-40-35(58)31(54)29(52)24(20-50)63-40)17-15-46(6)21(22(48)18-43)8-9-26-45(5)12-11-27(44(3,4)25(45)10-13-47(26,46)7)64-41-37(33(56)32(55)36(65-41)38(59)60)66-39-34(57)30(53)28(51)23(19-49)62-39/h8,22-37,39-41,49-58H,9-20H2,1-7H3,(H,59,60)/t22-,23+,24+,25-,26+,27-,28+,29+,30-,31-,32-,33-,34+,35+,36-,37+,39-,40-,41+,45-,46+,47+,48-/m0/s1 |
InChI Key | NFZYDZXHKFHPGA-QQHDHSITSA-N |
SMILES | O=C([C@H]1O[C@@H](O[C@H]2CC[C@]3(C)[C@@]4([H])CC=C5[C@]6([H])CC(C)(C)CC[C@]6(C(O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)=O)CC[C@@]5(C)[C@]4(C)CC[C@@]3([H])C2(C)C)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@@H](O)[C@@H]1O)O |
Solubility | Soluble in DMSO |
Synonyms | Ginsenoside Ro; Chikusetsusaponin 5; Chikusetsusaponin V; Polysciasaponin P3; |
Canonical SMILES | CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C |
Isomeric SMILES | C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O |
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