Sophoflavescenol

Datasheet MSDS
Catalog Number
ANC02112
Product Name
Sophoflavescenol
Structure
Sophoflavescenol
CAS Number
216450-65-6
IUPAC Name
3,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms
3,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)chromen-4-one
Molecular Formula
C21H20O6
Molecular Weight
368.385
Purity
>98%
Solubility
Soluble in DMSO
Description
Sophoflavescenol is a prenylated flavonol, which shows great inhibitory activity with IC50 of 13 nM against Phosphodiesterase 5 (PDE5), and also inhibits RLAR, HRAR, AGE, BACE1, AChE and BChE with IC50s of 0.30 μM, 0.17 μM, 17.89 μg/mL, 10.98 μM, 8.37 μM and 8.21 μM, respectively.IC50: 13 nM (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)Target:In Vitro: 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[1]. Sophoflavescenol exhibits remarkable inhibition of RLAR activity with an IC50 value of 0.30 μM, compared with 0.07 μM for epalrestat, a well known ARI. Sophoflavescenol also shows potent inhibitory activity with an IC50 value of 0.17 μM, comparable to epalrestat (0.15 μM) in the HRAR assay. In the AGE assay, sophoflavescenol (IC50 17.89 μg/mL) is a more potent inhibitor of AGE formation than aminoguanidine (IC50 81.05 μg/mL). Sophoflavescenol exerts both potent AChE and BChE inhibitory effects with respective IC50 values of 8.37 and 8.21 μM. Sophoflavescenol also exhibits good BACE1 inhibition in a dose-dependent manner with an IC50 value of 10.98 μM[2]. Sophoflavescenol is a mixed inhibitor (Ki = 0.005 μM) against cGMP PDE5. Sophoflavescenol shows greatest selectivity toward PDE5, 31.5- and 196.2-fold over PDE3 and PDE4, respectively[3].In Vivo: Sophoflavescenol exerts potent in vivo antitumor activity by tumor growth inhibition in the LLC tumor model as well as apoptotic activity by caspase-3 activation in HL-60 cells[1].
SMILES
CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)C(=C(O2)C3=CC=C(C=C3)O)O)C
InChI
InChI=1S/C21H20O6/c1-11(2)4-9-14-15(23)10-16(26-3)17-18(24)19(25)20(27-21(14)17)12-5-7-13(22)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
InChI Key
VMLJAWUWVVHRNG-UHFFFAOYSA-N
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