Dihydrotanshinone I

Names

[ Name ]:
Dihydrotanshinone I

[Synonym ]:
1,6-Dimethyl-1,2-dihydrophenanthro[1,2-b]furan-10,11-dione
1,2-dihydrotanshinone
Tanshinone I,dihydro
dihydrotanshinone 1
1,2-dihydrotanshinone I
15,16-dihydrotanshinone I
Phenanthro[1,2-b]furan-10,11-dione, 1,2-dihydro-1,6-dimethyl-
Dihydrotanshinone I

Biological Activity

[Description]:

Dihydrotanshinone I is a natural compound extracted from Salvia miltiorrhiza Bunge which has been widely used for treating cardiovascular diseases.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cardiovascular Disease

Natural Products >> Quinones

[In Vitro]

In lipopolysaccharide (LPS)-stimulated human umbilical vein endothelial cells (HUVECs), DHT (10 nM) decreases lectin-like ox-LDL receptor-1 (LOX-1) and NADPH oxidase 4 (NOX4) expression, reactive oxygen species (ROS) production, NF-κB nuclear translocation, ox-LDL endocytosis and monocytes adhesion[1]. Dihydrotanshinone I induces caspase dependent apoptosis induced in HCT116 cells. Dihydrotanshinone I induces concentration and ROS dependent caspase activation. Apoptosis induced by Dihydrotanshinone I is completely prevented by Z-VAD-fmk. Apoptosis induced by Dihydrotanshinone I is significantly inhibited by pretreatment of Z-LEHD-fmk but only is partially inhibited by Z-IETD-fmk. Apoptosis induced by Dihydrotanshinone I is significantly increased by caspase-2 knockdown[3].

[In Vivo]

DHT (10 and 25 mg/kg) significantly attenuates atherosclerotic plaque formation, alteres serum lipid profile, decreases oxidative stress and shrinks necrotic core areas in ApoE-/- mice. DHT dramatically inhibits the enhanced expression of LOX-1, NOX4, and NF-κB in aorta[1]. Dihydrotanshinone I (1, 2, 4 mg/kg) treatment can improve cardiac function, reduce infarct size, ameliorate the variations in myocardial zymogram and histopathological disorders, decrease 20-HETE generation, and regulate apoptosis-related protein in myocardial ischemia-reperfusion rats[2].

[Kinase Assay]

Cells are treated with various concentrations of Dihydrotanshinone I (3.13-20 µM) for 48 h. For the activity assay, Ac-DEVD-AMC (1 µg/µL), Ac-IETD-AMC (1 µg/µL) or Ac-LEDH-AMC (1 µg/µL) and cell lysate are added into Protease Assay Buffer in 96-well plate. Reaction mixtures with lysis buffer are used as negative controls. Cells treated with DMSO (0.1%) are treated as vehicle control. The reaction mixtures are incubated for 1 h at 37°C. The AMC liberated from the substrates is measured using spectrofluorometer of Victor 2 plate reader with an excitation wavelength of 380 nm and an emission wavelength of 430 nm.

[Animal admin]

Male ApoE-/- mice (6-8 weeks old) on C57BL/6J background and age-matched wild-type C57BL/6J controls housed in SPF-grade animal facilities with a 12 h light/dark cycle, at 23°C (±2°C). Starting from 6 weeks, the mice are fed with a HCD (54.35% raw grain, 20% lard, 0.15% cholesterol, 15% sucrose, 0.5% Sodium Cholate, 10% yolk powder) for 12 weeks. All ApoE-/- mice are dosed daily via intragastric gavage with 10 and 25 mg/kg Dihydrotanshinone I dissolved in 0.5% CMC-Na or administered 0.5% CMC-Na alone (vehicle control) (n=8 per group).

[References]

[1]. Zhao W, et al. Dihydrotanshinone I Attenuates Atherosclerosis in ApoE-Deficient Mice: Role of NOX4/NF-κB Mediated Lectin-Like Oxidized LDL Receptor-1 (LOX-1) of the Endothelium. Front Pharmacol. 2016 Nov 8;7:418. eCollection 2016.

[2]. Wei Y, et al. The cardioprotection of dihydrotanshinone I against myocardial ischemia-reperfusion injury via inhibition of arachidonic acid ω-hydroxylase. Can J Physiol Pharmacol. 2016 Dec;94(12):1267-1275. Epub 2016 Jun 24.

[3]. Wang L, et al. Dihydrotanshinone I induced apoptosis and autophagy through caspase dependent pathway in colon cancer. Phytomedicine. 2015 Nov 15;22(12):1079-87.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
479.2±45.0 °C at 760 mmHg

[ Melting Point ]:
214.0 to 218.0 °C

[ Molecular Formula ]:
C₁₈H₁₄O₃

[ Molecular Weight ]:
278.302

[ Flash Point ]:
214.9±28.8 °C

[ Exact Mass ]:
278.094299

[ PSA ]:
43.37000

[ LogP ]:
3.90

[ Appearance of Characters ]:
red

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.671

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
ethanol: soluble1mg/mL, clear, orange to red

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H400

[ Precautionary Statements ]:
P273

[ Hazard Codes ]:
Xn,N

[ Risk Phrases ]:
22-50

[ Safety Phrases ]:
61

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
SF8282630

Articles

Dihydrotanshinone-I interferes with the RNA-binding activity of HuR affecting its post-transcriptional function.

Sci. Rep. 5 , 16478, (2015)

Post-transcriptional regulation is an essential determinant of gene expression programs in physiological and pathological conditions. HuR is a RNA-binding protein that orchestrates the stabilization a...

Comparison of neuroprotective effects of five major lipophilic diterpenoids from Danshen extract against experimentally induced transient cerebral ischemic damage.

Fitoterapia 83 , 1666-1674, (2012)

We observed neuroprotective effects of five major lipophilic diterpenes derived from Danshen (Radix Salvia miltiorrhiza) extract, such as cryptotanshinone (CTs), dihydrotanshinone I (DTsI), tanshinone...

Modeling gradient elution in countercurrent chromatography: efficient separation of tanshinones from Salvia miltiorrhiza Bunge.

J. Sep. Sci. 35 , 964-976, (2012)

Countercurrent chromatography (CCC) is a support-free liquid-liquid chromatography using centrifugal fields to hold the liquid stationary phase. CCC has been widely applied in the separation of variou...

Related Compounds

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