Hispidulin

Names

[ Name ]:
Hispidulin

[Synonym ]:
Dinatin
Scutellarein 6-methyl ether
6-O-Methylapigenin
TCMDC-123942
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-
4',5,7-Trihydroxy-6-methoxyflavone
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxychromen-4-one
Hispidulin
6-O-Methoxyapigenin
5,7,4'-trihydroxy-6-methoxyflavone
5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
Flavone, 4',5,7-trihydroxy-6-methoxy-

Biological Activity

[Description]:

Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM.

[Related Catalog]:

Signaling Pathways >> JAK/STAT Signaling >> Pim

Research Areas >> Cancer

Natural Products >> Flavonoids

[Target]

IC50: 2.71 μM (Pim-1)[1]

[In Vitro]

Hispidulin induces cell death in a dose- and time-dependent manner in HepG2 cells. Hispidulin induces apoptosis through mitochondrial dysfunction, which is characterized by decreased Bcl-2/Bax ratio, disrupted mitochondrial membrane potential and increased release of cytochrome C and activated capase-3[2].

[In Vivo]

Hispidulin shows significant inhibitory effect on mice tumor size[2]. Hispidulin treatment effectively prevents ovariectomy-induced body weight loss and attenuates ovariectomy-induced bone loss. Hispidulin treatment also decreases trabecular spacing in ovariectomy mice[3]. Intraperitoneally administering hispidulin(10 or 50mg/ kg) to rats 30 min before intraperitoneally injecting kainic acid (15mg/kg) increases seizure latency and decreases seizure score. In addition, hispidulin substantially attenuates kainic acid-induced hippocampal neuronal cell death, and this protective effect is accompanied by the suppression of microglial activation and the production of proinflammatory cytokines such as interleukin-1β, interleukin-6, and tumor necrosis factor-α in the hippocampus[4].

[Cell Assay]

HepG2 cells are treated with different concentrations of hispidulin (50, 100, 200 μM) for 24, 48 and 72 h. Following treatment, cells are further incubated with MTT reagents at 37°C for 4 h before DMSO is added, to dissolve farmazan crystals, and absorbance is measured at 570 nm in a microplate reader[2].

[Animal admin]

Mice: Tumor are established in mice. Mice are treated with DMSO or Hispidulin at a dosage of 10, 20 or 40 mg/kg/day for 35 days. The body weight of tumour-bearing mice is recorded every week and tumour volume is calculated [2].

[References]

[1]. Chao SW, et al. Total Synthesis of Hispidulin and the Structural Basis for Its Inhibition of Proto-oncogene KinasePim-1. J Nat Prod. 2015 Aug 28;78(8):1969-76.

[2]. Gao H, et al. Hispidulin induces apoptosis through mitochondrial dysfunction and inhibition of P13k/Akt signalling pathway in HepG2 cancer cells. Cell Biochem Biophys. 2014 May;69(1):27-34.

[3]. Zhou R, et al. Hispidulin exerts anti-osteoporotic activity in ovariectomized mice via activating AMPK signaling pathway. Cell Biochem Biophys. 2014 Jun;69(2):311-7.

[4]. Lin TY, et al. Protective effect of hispidulin on kainic acid-induced seizures and neurotoxicity in rats. Eur J Pharmacol. 2015 May 15;755:6-15.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
601.5±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₆H₁₂O₆

[ Molecular Weight ]:
300.263

[ Flash Point ]:
230.1±25.0 °C

[ Exact Mass ]:
300.063385

[ PSA ]:
100.13000

[ LogP ]:
1.60

[ Appearance of Characters ]:
white to beige

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.697

[ Storage condition ]:
Desiccate at -20°C

[ Water Solubility ]:
DMSO: soluble20mg/mL, clear

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DJ2996000

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

Analysis of vervain flavonoids by HPLC/Diode array detector method. Its application to quality control.

J. Agric. Food Chem. 47(11) , 4579-82, (1999)

A reversed-phase HPLC procedure is proposed for the determination of seven flavonoids (luteolin, nepetin, hispidulin, jaceosidin, cirsimaritin, cirsilineol, and eupatorin) in vervain samples. A simple...

Inhibition of [methyl-3H]diazepam binding to rat brain membranes in vitro by dinatin and skrofulein.

Zhongguo Yao Li Xue Bao 15(5) , 385-8, (1994)

Two flavones, 4',5,7-trihydroxy-6-methoxy flavone (dinatin) and 4',5-dihydroxy-6, 7-dimethoxy flavone (skrofulein), were extracted from Artemisia herba alba L. Dinatin and skrofulein inhibited the bin...

Chemical fingerprint and quantitative analysis of Salvia plebeia R.Br. by high-performance liquid chromatography.

J. Pharm. Biomed. Anal. 48(1) , 100-4, (2008)

To control the quality of Salvia plebeia R.Br., a simple and reliable method of high-performance liquid chromatography coupled with photodiode array detector (HPLC-DAD) was developed both for fingerpr...