80681-45-4
prim-O-Glucosylcimifugin
CAS: 80681-45-4
Molecular Formula: C22H28O11
80681-45-4 - Names and Identifiers
| Name | prim-O-Glucosylcimifugin |
| Synonyms | Cimifugin 7-glucoside rim-O-glucosylcimifugin prim-O-Glucosylcimifugin CIMIFUGIN BETA-D-GLUCOPYRANOSIDE Cimifugin Beta-D-Glucopyranoside 5H-Furo[3,2-g][1]benzopyran-5-one,7-[(β-D- glucopyranosyloxy)methyl]-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-4-methoxy-,(2S)- (2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrofuro[3,2-g]chromen-5-one |
| CAS | 80681-45-4 |
| InChI | InChI=1/C22H28O11/c1-22(2,28)15-5-10-12(32-15)6-13-16(20(10)29-3)11(24)4-9(31-13)8-30-21-19(27)18(26)17(25)14(7-23)33-21/h4,6,14-15,17-19,21,23,25-28H,5,7-8H2,1-3H3/t14-,15+,17-,18+,19-,21-/m1/s1 |
80681-45-4 - Physico-chemical Properties
| Molecular Formula | C22H28O11 |
| Molar Mass | 468.45 |
| Density | 1.53±0.1 g/cm3(Predicted) |
| Melting Point | 118～120℃ |
| Boling Point | 736.9±60.0 °C(Predicted) |
| Appearance | Powder |
| pKa | 12.94±0.70(Predicted) |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.648 |
| Physical and Chemical Properties | White crystalline powder, soluble in methanol, derived from Fangji, Fangfeng, Huashan Qianhu. |
| In vitro study | Prim-O-glucosylcimifugin (POG) is the highest content chromone and one of the major active constituents in Radix Saposhnikoviae (RS). Prim-O-glucosylcimifugin exerts anti-inflammatory effects in RAW 264.7 macrophages through the inhibition of iNOS and COX-2 expression by inhibiting JAK2/STAT3 signaling. The cytotoxicity of Prim-O-glucosylcimifugin is measured to LPS-activated Raw 264.7 macrophages. Raw 264.7 macrophages are treated with LPS (1 μg/mL) and increasing concentrations of Prim-O-glucosylcimifugin (15, 50, and 100 μg/mL) for 24 h and cell viability is evaluated by CCK-8 assay. Cell viability is not significantly affected after 24 h and exposure to 15-100 μg/mL Prim-O-glucosylcimifugin as compared with DMSO-treated cells (control). To investigate the anti-inflammatory effect of Prim-O-glucosylcimifugin, whether Prim-O-glucosylcimifugin can affect NO synthesis is examined in LPS-activated RAW 264.7 cells. Macrophages are treated with LPS (1 μg/mL) and various concentrations of Prim-O-glucosylcimifugin (15, 50, and 100 μg/mL) for 24 h. No concentrations are measured in the culture supernatants by Griess reaction. The concentrations of NO in the culture supernatants are markedly increased in response to LPS exposure, and Prim-O-glucosylcimifugin significantly inhibits LPS-induced NO production in a concentration-dependent manner. |
| In vivo study | Bronchoalveolar lavage fluid (BALF) is collected at 7 h after lipopolysaccharide (LPS) administration and the cytokine levels in BALF are measured by ELISA. The levels of TNF-α, IL-1β and IL-6 in BALF are increased dramatically compared with control group. However, pretreatment with Prime-O-glucosylcimifugin (2.5, 5 or 10 mg/kg) significantly down-regulates the levels of TNF-α, IL-1β and IL-6 in a dose-dependent manner (P<0.05, P<0.01). |
80681-45-4 - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| HS Code | 29389090 |
80681-45-4 - Reference
| Reference Show more | 1. Xie Jing, Li Bo, Teng Fei, et al. Screening of phosphodiesterase 4-inhibiting active components from traditional Chinese medicine by ultrafiltration liquid chromatography [J]. Chemical Research & Application, 2018, 30(11):26-31. |
80681-45-4 - Reference Information
| Overview | coxigenin is a Saposhnikovia divarionate (Turcz.) schischk) dried roots of non-drawn stem plants are mainly produced in Heilongjiang, Inner Mongolia, Jilin, Hunan, Guizhou, Shandong and other places. |
| biological activity | Prim-O-glucosylcimifugin (CIMI fugin beta-D-glucopyranoside, CIMI fugin 7-glucoside) is the main component of Radix Saposhnikovia, it has long been used in traditional Chinese medicine for the treatment of Fever, rheumatism and cancer, it shows potential anti-cancer activity. In LPS-activated RAW 264.7 macrophages, Prim-O-glucosylcimifugin can down-regulate the mRNA and protein expression of NO synthase (iNOS) and cycloxygenase 2 (COX-2) in a concentration-dependent manner. |
| Target | COX-2 iNOS |
| in vitro study | Prim-O-glucosylcimifugin (POG) is the high content chrome and one of the major active constituents in Radix sapohnikoviae (RS). Prim-O-glucosylcimifugin exerts anti-inflammatory effects in RAW 264.7 macrophages through the inhibition of iNOS and COX-2 expression by inhibiting JAK2/STAT3 signaling. The cytotoxicity of Prim-O-glucosylcimifugin is measured to LPS-activated Raw 264.7 macrophages. Raw 264.7 macrophages are treated with LPS (1 μg/mL) and increasing concentrations of Prim-O-glucosylcimifugin (15, 50, and 100 μg/mL) for 24 h and cell viability is evaluated by CCK-8 assay. Cell viability is not significantly affected after 24 h and exposure to 15-100 μg/mL Prim-O-glucosylcimifugin as compared with DMSO-treated cells (control). To investigate the anti-inflammatory effect of Prim-O-glucosylcimifugin, whether Prim-O-glucosylcimifugin can affect NO synthesis is examined in LPS-activated RAW 264.7 cells. Macrophages are treated with LPS (1 μg/mL) and various concentrations of Prim-O-glucosylcimifugin (15, 50, and 100 μg/mL) for 24 h. No concentrations are measured in the culture supernatants Griess reaction. The concentrations of NO in the culture supernatants are markedly increased in response to LPS exposure, and Prim-O-glucosylcimifugin significantly inhibits LPS-induced NO production in a concentration-dependent manner. |
| in vivo study | bronchoalage fluid (BALF) is collected at 7 h after lipopolyacamide (LPS) administration and the cytokine levels in BALF are measured by ELISA. The levels of TNF-α, IL-1β and IL-6 in BALF are incremental. House, treatment with Prime-O-glucosylcimifugin (2.5, 5 or 10 mg/kg) significantly down-regulates the levels of TNF-α, IL-1β and IL-6 in a dose-dependent manner (P<0.05, P<0.01). |
| Chemical properties | white crystalline powder, soluble in methanol, derived from anti-versicolor, saposhnikovia, Mount Huashen. |
| Use | coxigenin has anti-inflammatory and immunosuppressive effects. for content determination/identification/pharmacological experiments. Pharmacological effects: antipyretic, analgesic, anti-inflammatory, anti-platelet aggregation and other effects. |
Last Update：2024-04-09 20:02:46
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