b-D-Glucopyranoside, (3b,12b,20Z)-12-hydroxydammara-20(22),24-dien-3-yl
ginsenoside Rh3
CAS: 105558-26-7
Molecular Formula: C36H60O7
b-D-Glucopyranoside, (3b,12b,20Z)-12-hydroxydammara-20(22),24-dien-3-yl - Names and Identifiers
| Name | ginsenoside Rh3 |
| Synonyms | ginsenoside Rh3 [(20Z)-12β-Hydroxy-5α-dammara-20(22),24-dien-3β-yl]β-D-glucopyranoside β-D-Glucopyranoside, (3β,12β,20Z)-12-hydroxydammara-20(22),24-dien-3-yl b-D-Glucopyranoside, (3b,12b,20Z)-12-hydroxydammara-20(22),24-dien-3-yl (5xi,9xi,12alpha,14beta,20Z)-12-hydroxydammara-20(22),24-dien-3-yl beta-D-glucopyranoside (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(8R,10R,12S,13R,14S,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2Z)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol |
| CAS | 105558-26-7 |
| InChI | InChI=1/C36H60O7/c1-20(2)10-9-11-21(3)22-12-16-36(8)28(22)23(38)18-26-34(6)15-14-27(33(4,5)25(34)13-17-35(26,36)7)43-32-31(41)30(40)29(39)24(19-37)42-32/h10-11,22-32,37-41H,9,12-19H2,1-8H3/b21-11-/t22-,23+,24-,25?,26?,27?,28+,29-,30+,31-,32+,34+,35-,36+/m1/s1 |
b-D-Glucopyranoside, (3b,12b,20Z)-12-hydroxydammara-20(22),24-dien-3-yl - Physico-chemical Properties
| Molecular Formula | C36H60O7 |
| Molar Mass | 604.86 |
| Density | 1.17±0.1 g/cm3(Predicted) |
| Boling Point | 695.0±55.0 °C(Predicted) |
| Flash Point | 374.1°C |
| Vapor Presure | 2.44E-22mmHg at 25°C |
| pKa | 12.91±0.70(Predicted) |
| Refractive Index | 1.569 |
| Physical and Chemical Properties | White powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from ginseng rhizome. |
| In vitro study | Ginsenoside Rh3 inhibits UV-induced oxidative damages in retinal cells via activating nuclear-factor-E2-related factor 2 (Nrf2) signaling. Ginsenoside Rh3 treatment in retinal cells induces Nrf2 activation. The potential activity of Ginsenoside Rh3 is tested on Nrf2 signaling in the retinal pigment epithelium cells (RPEs). The qRT-PCR assay results demonstrate that treatment with Ginsenoside Rh3 dose-dependently increases mRNA transcription and expression of key Nrf2-regulated genes, including HO1 , NQO1 and GCLC . Consequently, protein expressions of these Nrf2-dependent genes (HO1, NQO1 and GCLC) are also significantly increased in Ginsenoside Rh3 (3-10 μM)-treated RPEs. Notably, although Nrf2 mRNA level is unchanged after Ginsenoside Rh3 treatment, its protein level is significantly increased by Rh3. EZ-Cytox assay is used to assess the effect of ginsenoside-Rh3 on SP 1-keratinocytes viability. Ginsenoside Rh3 (0.01, 0.1, 1 and 10 μM) shows no cytotoxic effect at all concentrations. |
| In vivo study | The potential effect of Ginsenoside Rh3 is examined on mouse retina, using the light-induced retinal damage model. Ginsenoside Rh3 intravitreal injection (5 mg/kg body weight, 30 min pre-treatment) significantly attenuates light-induced decrease of both a- and b-wave amplitude. The electroretinography (ERG)'s a-wave decreases to 46.03±1.62% % of control level after light exposure, which is back to 71.84±7.51% with Ginsenoside Rh3 administration. The b-wave is 40.19±3.34% of control level by light exposure, and Rh3 intravitreal injection brings back to 80.01±2.37% of control level. |
b-D-Glucopyranoside, (3b,12b,20Z)-12-hydroxydammara-20(22),24-dien-3-yl - Reference Information
| introduction | ginsenoside Rh3 is a kind of ginsenoside with smaller molecular weight converted from Rg5 through biological metabolism, and its efficacy is stronger than Rg5. |
| use | ginsenoside Rh3 is a metabolite of ginsenoside Rg5, isolated from ginseng. Ginsenoside Rh3 can be used as a reference standard for the determination of ginsenoside Rg5 in Korean red ginseng by high performance liquid chromatography combined with evaporative light scattering detection (HPLC-ELSD). used for content determination/identification/pharmacological experiment, etc. Pharmacological effect: It has anti-inflammatory effect and can significantly inhibit the expression of iNOs and proinflammatory cytokines in LPS-induced activated microglia. ginsenoside Rh3 is a metabolite of ginsenoside Rg5 and has anti-inflammatory activities. |
| biological activity | Ginsenoside Rh3 is a bacterial metabolite Ginsenoside Rg5. Ginsenoside of Rh3 in human retinal cells induces Nrf2 activation. |
| target | Nrf2 |
| in vitro study | Ginsenoside Rh3 inhibits UV-induced oxidative damages in retinal cells via activating nuclear-factor-E2-related factor 2 (Nrf2) signaling. Ginsenoside Rh3 treatment in retinal cells induces Nrf2 activation. The potential activity of Ginsenoside Rh3 is examined on Nrf2 signaling in the retinal pigment epithelium cells (RPEs). The qRT-PCR say results demonstrate that treatment with Ginsenoside Rh3 dose-dependently increases mRNA transcription and expression of key nrf2-regulated genes, including HO1, NQO1 and GCLC . Consequently, protein expressions of these Nrf2-dependent genes (HO1, NQO1 and GCLC) are also significantly increased in Ginsenoside Rh3 (3-10 μM)-treated RPEs. Notably, although Nrf2 mRNA level is unchanged after Ginsenoside Rh3 treatment, its protein level is significantly increased by Rh3. EZ-Cytox assayis used to assess the effect of ginsenoside-Rh3 on SP 1-keratinocytes viability. Ginsenoside Rh3 (0.01, 0.1, 1 and 10 μ m) shows no cytotoxic effect at all concentrations. |
| in vivo study | the potential effect of Ginsenoside Rh3 is examined on mouse retina, using the light-induced retinal damage model. Ginsenoside Rh3 intravitreal injection (5 mg/kg body weight, 30 min pre-treatment) significantly attenuates light-induced decrease of both a- and b-wave amplitude. The electroretinography (ERG)'s a-wave decreases to 46.03±1.62% % of control level after light exposure, which is back to 71.84±7.51% with Ginsenoside Rh3 administration. The b-wave is 40.19±3.34% of control level by light exposure, and Rh3 intravitreal injection brings back to 80.01±2.37% of control level. |
| chemical properties | white powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from ginseng rhizome. |
Last Update：2024-04-09 20:52:54
