216450-65-6
Sophoflavescenol
CAS: 216450-65-6
Molecular Formula: C21H20O6
216450-65-6 - Names and Identifiers
216450-65-6 - Physico-chemical Properties
| Molecular Formula | C21H20O6 |
| Molar Mass | 368.38 |
| Density | 1.359±0.06 g/cm3(Predicted) |
| Melting Point | 273-275 °C |
| Boling Point | 631.8±55.0 °C(Predicted) |
| Appearance | Yellow powder |
| pKa | 7.03±0.40(Predicted) |
| Storage Condition | 2-8℃ |
| In vitro study | Sophoflavescenol shows cytotoxicity against human leukaemia (HL-60), Lewis lung carcinoma (LLC), and human lung adenocarcinoma epithelial (A549) cells. Sophoflavescenol exerts notable anti-inflammatory activity by inhibiting nitric oxide generation and tert-butylhydroperoxide-induced ROS generation rather than inhibiting nuclear factor kappa B activation in RAW 264.7 cells. Sophoflavescenol exhibits remarkable inhibition of RLAR activity with an IC 50 value of 0.30 µM, compared with 0.07 µM for epalrestat, a well known ARI. Sophoflavescenol also shows potent inhibitory activity with an IC 50 value of 0.17 µM, comparable to epalrestat (0.15 µM) in the HRAR assay. In the AGE assay, sophoflavescenol (IC 50 17.89 µg/mL) is a more potent inhibitor of AGE formation than aminoguanidine (IC 50 81.05 µg/mL). Sophoflavescenol exerts both potent AChE and BChE inhibitory effects with respective IC 50 values of 8.37 and 8.21 µM. Sophoflavescenol also exhibits good BACE1 inhibition in a dose-dependent manner with an IC 50 value of 10.98 µM. Sophoflavescenol is a mixed inhibitor (K i =0.005 μM) against cGMP PDE5. Sophoflavescenol shows greatest selectivity toward PDE5, 31.5- and 196.2-fold over PDE3 and PDE4, respectively. |
| In vivo study | Sophoflavescenol exerts potent invivoantitumoractivityby tumor growth inhibition in the LLC tumor model as well as apoptoticactivityby caspase-3 activation in HL-60 cells. |
216450-65-6 - Reference Information
| action | flavonoids, including anti-tumor, anti-inflammatory and anti-osteoporosis activities, enzyme inhibition and vascular protection and estrogen-regulated activity. Sophorinol, a C- 8-isopentenylated flavonoid from S.flavescens, is the most potent and selective inhibitor of CGMP phosphodiesterase 5(PDE5; Ic500.013 μm) and is therefore considered to be a therapeutic lead. Sophorinol also showed inhibitory activity against HL-60,LLC and A549 tumor cells. |
| preparation | 7,8-(2, 2-dimethyl-2h-pyran)-5, 4-dihydroxyflavonol (sophorinol, 12):(CH3)2SO4(10.53mmol,1.0mL) was added dropwise to a stirred solution of 11(500mg,1.02mmol) in NaOH(5% aqueous solution; 15mL) in solution. The mixture was stirred at room temperature and maintained at pH9-10 for 5 hours. Thereafter, the reaction mixture was adjusted to pH 6 using HCl(2% aqueous solution) and then extracted with the mixture. Water was dried over anhydrous Na2SO4 and the solvent was evaporated. The solid residue was recrystallized from EtOAc/petroleum ether to give sophorinol (181mg,96%) as yellow needles, melting point 272-274 °c. |
| biological activity | sophorafensol is an isopentenyl flavonoid that inhibits the activity of PDE5, the IC50 value was 0.013 μm; The simultaneous inhibition of RLAR,HRAR,BACE1,AChE and BChE was 0.30 μm, 0.17 μm and 10.98 μm, respectively, 8.37 µm and 8.21 µm. |
| Target | IC50: 0.013 μm (PDE5), 0.30 μm (RLAR), 0.17 µm (HRAR), 17.89 µg/mL (AGE), 10.98 µm (BACE1), 8.37 µm (AChE), 8.21 µm (BChE) |
Last Update：2024-04-09 20:52:54
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Product Name: Sophoflavescenol Visit Supplier Webpage Request for quotationCAS: 216450-65-6
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Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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