Warangalone

Names

[ Name ]:
Warangalone

[Synonym ]:
2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-buten-1-yl)-
5-Hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-buten-1-yl)-2H,6H-pyrano[3,2-g]chromen-6-one
2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 5-hydroxy-7-(p-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
5-Hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-en-1-yl)-2H,6H-pyrano[3,2-g]chromen-6-one
Warangalone
Scandenone
2H,6H-Benzo(1,2-b:5,4-b')dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
Scandenolone

Biological Activity

[Description]:

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA

Signaling Pathways >> Stem Cell/Wnt >> PKA

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

Research Areas >> Infection

[Target]

IC50: 4.8 μg/mL (3D7), 3.7 μg/mL (K1)[1] IC50: 3.5 μM (cAK)[2]

[In Vitro]

Warangalone is an anti-malarial compound which can inhibit the growth of both strains of parasite 3D7 (chloroquine sensitive) and K1 (chloroquine resistant) with IC50s of 4.8 μg/mL and 3.7 μg/mL, respectively[1]. Warangalone can also inhibit cyclic AMP-dependent protein kinase catalytic subunit (cAK) with an IC50 of 3.5 μM[2]. When HL-60 cells are exposed to Warangalone (30 μM) for 24 h, Warangalone induces a significant decrease (8%) in cell viability compare to controls. Warangalone also inhibits HL-60 cell growth within 24 h in a time-dependent fashion. A time-dependent increase in caspase-9 activity is observed in Warangalone-treated cells[3].

[Kinase Assay]

The enzyme activities of caspase-3 and caspase-9 are measured using a caspase fluorometric assay kit. Cells are seeded in 24-well plates at a density of 3×106 cells per well. After exposure of the cells to Warangalone for the allotted time periods, the cells are washed three times with PBS, and then lysed in a lysis buffer for 10 min on ice. The protein content of the cell lysates is assayed with a Micro BCA reagent. Cell lysates containing 50 μg of protein are incubated with a caspase-3 fluorogenic substrate (DEVD-AFC) or a caspase-9 fluorogenic substrate (LEHD-AFC) for 1 h at 37°C. Caspase activity is measured by fluorometric detection[3].

[Cell Assay]

Cell viability is determined using the Cell Titer 96 Aqueous assay kit. Cells are seeded in 96-well plates at a density of 1×105 cells per well. The cells are maintained for 24 h at 37°C and then Warangalone (30 μM) is added to the culture medium. MTS solution is added to the 96-well plates at the indicated time points, and the cells are incubated for 1 h at 37°C. The absorbance is measured at a wavelength of 490 nm with a microplate counter[3].

[References]

[1]. Tati Herlina, et al. ANTI-MALARIAL COMPOUND FROM THE STEM BARK OF Erythrina variegate. Indo. J. Chem., 2009, 9 (2), 308-311.

[2]. Wang BH, et al. Specific inhibition of cyclic AMP-dependent protein kinase by warangalone and robustic acid. Phytochemistry. 1997 Mar;44(5):787-96.

[3]. Induction of apoptosis by isoflavonoids from the leaves of Millettia taiwaniana in human leukemia HL-60 cells. Planta Med. 2006 Apr;72(5):424-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
627.0±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₂₄O₅

[ Molecular Weight ]:
404.455

[ Flash Point ]:
216.7±25.0 °C

[ Exact Mass ]:
404.162384

[ PSA ]:
79.90000

[ LogP ]:
7.87

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.628

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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