4449-55-2

4449-55-2 structure

Name: Warangalone
Chemical Name: 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
CAS Number: 4449-55-2
Molecular Formula: C₂₅H₂₄O₅
Molecular Weight: 404.455
Catalog: Natural product Flavonoids
Create Date: 2016-07-26 08:55:45
Modify Date: 2024-01-02 17:56:56
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. Warangalone can also inhibit cyclic AMP-dependent protein kinase catalytic subunit (cAK) with an IC50 of 3.5 μM.

Name	5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
Synonyms	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

Description	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. Warangalone can also inhibit cyclic AMP-dependent protein kinase catalytic subunit (cAK) with an IC50 of 3.5 μM.
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.

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

51225-28-6

4449-55-2

482-53-1

Literature: Singhal, Ashok K.; Sharma, Ram P.; Thyagarajan, Gopalakrishna; Herz, Werner; Govindan, Serengolam V. Phytochemistry (Elsevier), 1980 , vol. 19, p. 929 - 934

Precursor 1
51225-28-6
DownStream 0

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