73069-28-0
73069-28-0 structure
- Name: Praeruptorin B
- Chemical Name: [8,8-dimethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (Z)-2-methylbut-2-enoate
- CAS Number: 73069-28-0
- Molecular Formula: C24H26O7
- Molecular Weight: 426.459
- Catalog: Research Areas Metabolic Disease
- Create Date: 2018-03-30 08:00:00
- Modify Date: 2024-01-06 21:14:39
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Praeruptorin B is an inhibitor of sterol regulatory element-binding proteins (SREBPs).
| Name | [8,8-dimethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (Z)-2-methylbut-2-enoate |
|---|---|
| Synonyms |
(9S,10S)-8,8-Dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f]chromene-9,10-diyl (2Z,2'Z)bis(2-methyl-2-butenoate)
Praeruptorin D 8,8-Dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f]chromene-9,10-diyl (2Z,2'Z)bis(2-methyl-2-butenoate) 2-Butenoic acid, 2-methyl-, 9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9,10-diyl ester, (2Z,2'Z)- (-)-praeruptorin B 2-Butenoic acid, 2-methyl-, (9S,10S)-9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9,10-diyl ester, (2Z,2'Z)- 8,8-Dimethyl-2-oxo-2,8,9,10-tetrahydropyrano(2,3-f)chromene-9,10-diyl bis((Z)-2-methyl-2-butenoate) HMS2270D13 (9S,10S)-8,8-Dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f]chromene-9,10-diyl (2Z,2'Z)bis(2-methylbut-2-enoate) (-)-cis-(3S,4S)-3,4-diangeloxylkhellactone (+)-Anomalin Praeruptorin B |
| Description | Praeruptorin B is an inhibitor of sterol regulatory element-binding proteins (SREBPs). |
|---|---|
| Related Catalog | |
| Target |
SREBP[1]. |
| In Vitro | Praeruptorin B inhibits the SREBPs activity and decreases intracellular lipid levels. Praeruptorin B is found to powerfully decrease the SRE-luciferase activity, and this effect is dose dependent. Praeruptorin B shows negligible cytotoxicity, even at the higher concentration. Praeruptorin B also significantlytly down-regulates the expression of SREBP-1c and SREBP-2[1]. Praeruptorin B also exhibits significant inhibition on the activity of UGT1A9[2]. |
| In Vivo | The mice treated with Praeruptorin B (50 mg/kg) are significantly lighter than the vehicle treated mice, although they are still heavier than the chow diet-fed mice, suggesting that Praeruptorin B can ameliorate diet-induced obesity (DIO). More importantly, the fat/lean and fat/body-weight ratios are obviously dropped at the same dosage of Praeruptorin B treated mice. It is also showed that the serum TC and TG levels of Praeruptorin B treated mice are significantly lower than those of the HFD-fed mice. Praeruptorin B increases HDL-c and decreases LDL-c similar as lovastatin. In addition, compared with vehicle treated mice, Praeruptorin B significantly lowers the level of TC and TG in liver, comparable to lovastatin. The staining results reveal that Praeruptorin B-treated mice exhibit less lipid accumulation than that of vehicle treated mice. The elevated fasting blood glucose and insulin in HFD-fed mice are significantly reduced by Praeruptorin B[1]. |
| Cell Assay | HepG2 cells and HL-7702 cells are used in the study. Cell proliferation is determined by the MTT assays. The HepG2 cells are seeded in 96-well plates with 2.0×104 cells per well in DMEM containing 10% FBS for 24 h. Cells are further treated with Praeruptorin B (0, 2.5, 5, 10, 20, 40, 80 μM) for 18 h[1]. |
| Animal Admin | Mice[1] Sixweek-old male C57BL/6J mice are housed in colony cages and maintained on a light/dark cycle. On a caloric basis, the HFD contains 60% fat, 20.6% carbohydrate and 19.4% protein, whereas the normal diet contains 13% fat, 60% carbohydrate and 27% protein. The mice are randomly divided into the following four groups (n=6 per group): vehicle-treated chow group, vehicle-treated HFD group, lovastatin-treated HFD group (30 mg per kg per day) and Praeruptorin B-treated HFD group (25 or 50 mg per kg per day). HFD-fed mice are gavaged with Praeruptorin B or lovastatin dissolved in 0.5% CMC-Na for 6 weeks[1]. |
| References |
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 524.8±50.0 °C at 760 mmHg |
| Melting Point | 175-176ºC |
| Molecular Formula | C24H26O7 |
| Molecular Weight | 426.459 |
| Flash Point | 225.5±30.2 °C |
| Exact Mass | 426.167847 |
| PSA | 92.04000 |
| LogP | 5.99 |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.573 |
| Storage condition | 2-8℃ |