| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H10O3 |
| Molecular Weight | 238.2381 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(OC(=CC2=O)C3=CC=CC=C3)C=C1
InChI
InChIKey=GPZYYYGYCRFPBU-UHFFFAOYSA-N
InChI=1S/C15H10O3/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-9,16H
6-Hydroxyflavone is a naturally occurring flavone found in the leaves of Barleria prionitis, a plant species in the Acanthaceae family native to India that is widely used against neurological disorders such as paraplegia, sciatica, etc. 6-Hydroxyflavone partially potentiated GABA-induced currents in native GABAA receptors expressed in cortical neurons via BZ site, as the enhancement was blocked by the antagonist flumazenil. Furthermore, in patch clamp studies, 6-Hydroxyflavone displayed the significant preference for a2- and a3- containing subtypes, which were thought to mediate anxiolytic effect, compared to a1- and a5- containing subtypes expressed in HEK 293T cells. In mice, 6-Hydroxyflavone exhibited the anxiolytic-like effect in the elevated plus-maze test, unaccompanied at anxiolytic doses by the sedative, cognitive impairing, myorelaxant, motor incoordination and anticonvulsant effects commonly associated with classical BZs when tested in the hole-board, step-through passive avoidance, horizontal wire, rotarod, and pentylenetetrazol (PTZ)-induced seizure tests, respectively. The findings, therefore, identified 6-Hydroxyflavone as a promising drug candidate for the treatment of anxiety-like disorders.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
ICR mice were treated with 6, 12, 25, 50 or 100 mg/kg, p.o.
Route of Administration:
Oral
The cytotoxic effects of the flavones (flavone, 6-OH-F, 7-OH-F, baicalein, and luteolin) on the MC3T3 cells were evaluated using an MTT assay. The MC3T3-E1 cells were seeded in a 96-well plate at 3000 cells per well and cultured for 48 h. After rinsing with PBS, the cells were treated with various concentrations of the selected flavones in a fresh medium for 24 h. The viable cells were then treated with a newly prepared medium containing 10 𝜇L of 5mg/mL MTT and 90 𝜇L of the 𝛼-MEM (10% FBS, 1x anti-anti) in a CO2 incubator for 2 h. The MTT was transformed by the living cells to a purple formazan dye which was dissolved in 100 𝜇L DMSO by shaking at 150 rpm for 10min with an ELISA shaker. Finally, the relative colorimetric intensity of each well was evaluated using a Varioskan flash multimode reader (Thermo Fisher Scientific Inc., MA, USA) at a 570 nm wavelength. The cell viability of the control group without exposure to the flavones was defined as 100%.
SUBSTANCE RECORD
