Galangin

Names

[ CAS No. ]:
548-83-4

[ Name ]:
Galangin

[Synonym ]:
EINECS 208-960-4
3,5,7-trihydroxyflavone
Galangin
teptochrysin
Galengin
3,5,7-trihydroxy-2-phenyl-chromen-4-one
3,5,7-trihydroxy-flavon
3,5,7-Trihydroxy-2-phenyl-4H-chromen-4-one
3,5,7-Trihydroxy-Flavone
galangine
5,7-dihydroxyflavonol
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl-
NORIZALPININ
3,5,7-trihydroxyfalvone
MFCD00006833
3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one

Biological Activity

[Description]:

Galangin is an agonist/antagonist of the arylhydrocarbon receptor, and also shows inhibition of CYP1A1 activity.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Cancer

Natural Products >> Flavonoids

[In Vitro]

Galangin inhibits the catabolic breakdown of DMBA, as measured by thin-layer chromatography, in a dose-dependent manner. Galangin also inhibits the formation of DMBA-DNA adducts, and prevents DMBA-induced inhibition of cell growth. Galangin causes a potent, dose-dependent inhibition of CYP1A1 activity, as measured by ethoxyresorufin-O-deethylase activity, in intact cells and in microsomes isolated from DMBA-treated cells. Analysis of the inhibition kinetics by double-reciprocal plot demonstrates that galangin inhibits CYP1A1 activity in a noncompetitive manner. Galangin causes an increase in the level of CYP1A1 mRNA, indicating that it may be an agonist of the aryl hydrocarbon receptor, but it inhibits the induction of CYP1A1 mRNA by DMBA or by 2,3,5,7-tetrachlorodibenzo-p-dioxin (TCDD). Galangin also inhibits the DMBA- or TCDD-induced transcription of a reporter vector containing the CYP1A1 promoter[1]. Galangin treatment inhibits cell proliferation and induced autophagy (130 μM) and apoptosis (370 μM). In particular, galangin treatment in HepG2 cells causes (1) an accumulation of autophagosomes, (2) elevated levels of microtubule-associated protein light chain 3, and (3) an increased percentage of cells with vacuoles. p53 expression is also increased. The galangin-induced autophagy is attenuated by the inhibition of p53 in HepG2 cells, and overexpression of p53 in Hep3B cells restored the galangin-induced higher percentage of cells with vacuoles to normal level[2].

[Cell Assay]

Cells (5.0×103) are seeded and treated with different concentrations of galangin for different periods of time in 96-well plates. The number of viable cells in each well is determined by adding 10 µL of 5 mg/mL MTT solution. Following the 4 hour incubation at 37°C, the cells are dissolved in a 100 µL solution containing 20% SDS and 50% dimethy formamide. The optical densities are quantified at a test wavelength of 570 nm with a reference wavelength of 630 nm using a Varioskan Flash Reader spectrophotometer.

[References]

[1]. Ciolino HP, et al. The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Br J Cancer. 1999 Mar;79(9-10):1340-6.

[2]. Wen M, et al. Galangin induces autophagy through upregulation of p53 in HepG2 cells. Pharmacology. 2012;89(5-6):247-55.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
518.6±50.0 °C at 760 mmHg

[ Melting Point ]:
214-215 °C(lit.)

[ Molecular Formula ]:
C₁₅H₁₀O₅

[ Molecular Weight ]:
270.237

[ Flash Point ]:
202.0±23.6 °C

[ Exact Mass ]:
270.052826

[ PSA ]:
90.90000

[ LogP ]:
2.83

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.748

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LK9275500

CHEMICAL NAME :: Flavone, 3,5,7-trihydroxy-

CAS REGISTRY NUMBER :: 548-83-4

BEILSTEIN REFERENCE NO. :: 0272179

LAST UPDATED :: 199803

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C15-H10-O5

MOLECULAR WEIGHT :: 270.25

WISWESSER LINE NOTATION :: T66 BO EVJ CR& DQ GQ IQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 20 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 113,45,1983

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LK9275500

[ HS Code ]:
2914400090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914400090

[ Summary ]:
2914400090 other ketone-alcohols and ketone-aldehydes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

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Related Compounds

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