Apigenin

Names

[ CAS No. ]:
520-36-5

[ Name ]:
Apigenin

[Synonym ]:
5,7,4'-trihydroxyflavone
apigenol
Versuline
Versulin
4',5,7-Trihydroxyflavone
CHAMOMILE
Celery seed extract
C.I. NATURAL YELLOW 1
T66 BO EVJ CR DQ& GQ IQ
Apigenine
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Apigenin
EINECS 208-292-3
Pelargidenone
MFCD00006831

Biological Activity

[Description]:

Apigenin is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

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

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[Target]

Ki: 2 μM (CYP2C9)[1]

[In Vitro]

Apigenin inhibits cytochrome P450 2C9 (CYP2C9) with a Ki of 2 μM in the CYP2C9 RECO system (a purified, reconstituted enzyme system containing recombinant human CYP2C9, P450 reductase, cytochrome b5, and liposomes)[1]. Apigenin inhibits the cell proliferation. The growth inhibition rate (IR) of 20, 40, and 80 μM of Apigenin is 38%, 71%, and 99% respectively on the 7thd. after exposure to Apigenin for 24 or 48 h, the clone formation of SGC-7901 cells is suppressed in a dose- and time-dependent manner. The cloning efficiency in 80 μM is 9.8% and 5% after treatment with Apigenin for 24 and 48 h, while in the control group it is 40.4% and 43.4%[2].

[In Vivo]

Apigenin (API), a natural flavonoid, possesses a broad spectrum of biological properties, including antioxidative, anti-inflammatory, anticancer, and neuroprotective effects. Apigenin (125 mg/kg and 250 mg/kg) alleviates Adriamycin (ADR) (24 mg/kg)-induced myocardial injury. Apigenin inhibits serum aspartate amino transferase (AST) release. Apigenin reduces serum lactate dehydrogenase (LDH) release. Apigenin reduces serum creatine kinase (CK) contents[3].

[Cell Assay]

The effect of Apigenin on the viability of cells is determined by MTT assay. Near-confluent stock cultures of human gastric cancer SGC-7901 cells are harvested with 0.2% EDTA and plated at a density of 2.5×103/well in 96-well microtiter plates. After an overnight incubation to allow cell attachment, the medium is replaced by fresh medium containing different concentrations (0, 20, 40, and 80 μM) of Apigenin. Control wells receive DMSO (0.2%). Each concentration of Apigenin is repeated in four wells. After incubation for 24 h, one plate is assayed with a microplate reader at the wavelength of 570 nm. Before the assay, MTT (5 mg/mL in PBS) is added to each well and incubated for 4 h, then MTT solution is removed from the wells by aspiration. After careful removal of the medium, 0.1 mL of DMSO is added to each well, and the plate is shaken for 15 min. The data of 7 d are fed into the computer and the growth curve is drawn. The growth inhibition rate (IR) is calculated[2].

[Animal admin]

Mice[3] Sixty healthy Kunming mice (26±2 g) are randomly assigned into two groups: a control group (n=15) and an ADR group (n=45). The ADR group is divided into three subgroups: ADR only without Apigenin (ADR, n=15), low-dose Apigenin (125 mg/kg/day, n=15), and high-dose Apigenin (250 mg/kg/day, n=15). All Apigenin-treated groups are treated daily via gastric gavage for seventeen days with a 125 or 250 mg/kg/day dose. ADR (3 mg/kg/day) is injected intraperitoneally into animals at an interval of 48 h (in total, eight times at a cumulative dose of 24 mg/kg). The mice in the control group receive injections of 0.9% sterile saline. On the 17th day after the first treatment, the mice are sacrificed, and blood samples are collected. A number of hearts are fixed with 2.5% glutaraldehyde fixative for electron microscopy analysis, and the others are stored at -80°C for western blot analysis.

[References]

[1]. Si D, et al. Mechanism of CYP2C9 inhibition by flavones and flavonols. Drug Metab Dispos. 2009 Mar;37(3):629-34.

[2]. Wu K, et al. Inhibitory effects of apigenin on the growth of gastric carcinoma SGC-7901 cells. World J Gastroenterol. 2005 Aug 7;11(29):4461-4.

[3]. Yu W, et al. Apigenin Attenuates Adriamycin-Induced Cardiomyocyte Apoptosis via the PI3K/AKT/mTOR Pathway. Evid Based Complement Alternat Med. 2017;2017:2590676.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
555.5±50.0 °C at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₁₅H₁₀O₅

[ Molecular Weight ]:
270.237

[ Flash Point ]:
217.1±23.6 °C

[ Exact Mass ]:
270.052826

[ PSA ]:
90.90000

[ LogP ]:
2.10

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.732

[ Water Solubility ]:
DMSO: 27 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LK9276000

CHEMICAL NAME :: Flavone, 4',5,7-trihydroxy-

CAS REGISTRY NUMBER :: 520-36-5

BEILSTEIN REFERENCE NO. :: 0262620

LAST UPDATED :: 199707

DATA ITEMS CITED :: 3

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

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 10 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 246,205,1991

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-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LK9276000

[ HS Code ]:
2942000000

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914501900

[ Summary ]:
2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

Rapid evaluation and comparison of natural products and antioxidant activity in calendula, feverfew, and German chamomile extracts.

J. Chromatogr. A. 1385 , 103-10, (2015)

The present study describes a simple high performance thin layer chromatographic (HPTLC) method for the simultaneous quantification of apigenin, chamazulene, bisabolol and the use of DPPH free radical...

Effects of flavonoids on senescence-associated secretory phenotype formation from bleomycin-induced senescence in BJ fibroblasts.

Biochem. Pharmacol. 96 , 337-48, (2015)

During senescence, cells express molecules called senescence-associated secretory phenotype (SASP), including growth factors, proinflammatory cytokines, chemokines, and proteases. The SASP induces a c...

Apigenin induces caspase-dependent apoptosis by inhibiting signal transducer and activator of transcription 3 signaling in HER2-overexpressing SKBR3 breast cancer cells.

Mol. Med. Report. 12 , 2977-84, (2015)

Phytoestrogens have been demonstrated to inhibit tumor induction; however, their molecular mechanisms of action have remained elusive. The present study aimed to investigate the effects of a phytoestr...