Dihydrotanshinone I 87205-99-0
Dihydrotanshinone I
CAS: 87205-99-0
Molecular Formula: C18H14O3
Dihydrotanshinone I 87205-99-0 - Names and Identifiers
| Name | Dihydrotanshinone I |
| Synonyms | Dihydrotanshinone I 15,16-Dihydrotanshine I Dihydrotanshinone I 87205-99-0 Dihydrotanshinone Ⅰ, froM Salvia Miltiorrhiza 4,17-Dimethyl-15-oxagona-1,3,5(10),6,8,13-hexene-11,12-dione (-)-1,2-Dihydro-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione (1R)-1,6-dimethyl-1,2-dihydrophenanthro[1,2-b]furan-10,11-dione 1,6-Dimethyl-1,2,10,11-tetrahydrophenanthro[1,2-b]furan-10,11-dione (1R)-1,6-diMethyl-1,2-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione phenanthro[1,2-b]furan-10,11-dione, 1,2-dihydro-1,6-dimethyl-, (1R)- |
| CAS | 87205-99-0 |
| InChI | InChI=1S/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-7,10H,8H2,1-2H3/t10-/m0/s1 |
Dihydrotanshinone I 87205-99-0 - Physico-chemical Properties
| Molecular Formula | C18H14O3 |
| Molar Mass | 278.3 |
| Density | 1.32±0.1 g/cm3(Predicted) |
| Melting Point | 214.0 to 218.0 °C |
| Boling Point | 479.2±45.0 °C(Predicted) |
| Flash Point | 215°C |
| Solubility | Soluble in ethanol, acetone, ether, benzene and other organic solvents, slightly soluble in water. |
| Vapor Presure | 2.41E-09mmHg at 25°C |
| Appearance | reddish brown needle crystal |
| Color | red |
| Maximum wavelength(λmax) | 239nm(lit.) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.67 |
| MDL | MFCD28016070 |
| Physical and Chemical Properties | Red needle-like crystals, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Salvia miltiorrhiza. |
| In vitro study | 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. 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. |
| In vivo study | 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. 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. |
Dihydrotanshinone I 87205-99-0 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R50 - Very Toxic to aquatic organisms |
| Safety Description | 61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| RTECS | SF8282630 |
| HS Code | 29329990 |
Dihydrotanshinone I 87205-99-0 - Reference
| Reference Show more | 1. Li Huifen, song Meng, Cui Weiliang et al. Determination of the content of four kinds of Salvia miltiorrhiza ketone components before and after the wine of Salvia miltiorrhiza by a multi-evaluation method [J]. Shandong Journal of Traditional Chinese Medicine 2018 037(005):416-419 428. 2. Sun Beiye, Ying Tao, Wang Dong, Qian Junqiang, Lou Jianshi. Inhibitory effect of dihydrotanshinone on human lung cancer GLC-82 cells and its mechanism [J]. China pharmacy 2015 26(34):4775-4778. 3. Zhong Guangjun, Wang Zhao, Wang Daorong et al. Effects of dihydrotanshinone on proliferation and apoptosis of human gastric cancer cell line MKN-45 [J]. Chinese Journal of Clinical Pharmacology, 2019 035(022):2872-2874. 4. Liang Chen, Dong Changcheng. Effect of dihydrotanshinone on proliferation and apoptosis of human non-Hodgkin lymphoma Raji cells and its mechanism [J]. World Traditional Chinese Medicine 2019 v.14(12):119-122. 5. Ge Yuqing Cheng Ru Bin Chen Meng et al. Inhibitory effect of dihydrotanshinone on invasion and migration of human gastric cancer SGC7901 cells and its mechanism [J]. Chinese herbal medicine 2017 48(015):3138-3144. 6. Ni Jianhua, Zhu Jiangbo, Yin Guolin, et al. Mechanism of dihydrotanshinone regulating proliferation and invasion of bladder cancer T-24 cells via GSK3β/Wnt pathway [J]. Chinese pharmacist 2020(7):1256-1260. 7. Cheng Yizhi, Huang feichao, Chen Jiangtian. Dihydrotanshinone regulates Wnt/β-catenin signaling pathway to inhibit proliferation of colorectal cancer cells [J]. Chinese Journal of Clinical Pharmacology 2019(15). 8. Cheng, Rubin, Lou, Zhao, Huan Ge Yuqing, et al. Effect and mechanism of dihydrotanshinone on proliferation, migration and apoptosis of gastric cancer cells [J]. Chinese Journal of Traditional Chinese Medicine 2017 032(007):2936-2941. 9. Hu Weihui, Han Dong, Qijiang Kun, et al. Simultaneous determination of 12 components in Salvia przewalskii by RP-HPLC [J]. Journal of Pharmaceutical Analysis 2016 v.36(03):486-493. 10. Feng, missing Wang, Rui, Guwen, et al. Effects of different intensities of red and blue light on root morphology and accumulation of effective components of Salvia miltiorrhiza [J]. Chinese herbal medicine 2019(21). 11. Cheng Pei, Han Dongqi, Hu Weihui, etc. Simultaneous determination of 10 water-soluble and 4 fat-soluble components in Salvia miltiorrhiza by high performance liquid chromatography [J]. Journal of Pharmaceutical Analysis, 2015(06):991-996. 12. Cui Weiliang, Li Huifen, Zhang Xuelan, et al. Analysis of 5 kinds of qualitative change compounds before and after wine processing of Danshen by UPLC-QE/MS [J]. Chinese patent medicine 2019 041(004):844-849. 13. Zhang ruigan, Wu Xiaoyi, Hu Tianyuan, Song Yadi, Gao Wei, Huang Luqi. Study on quality markers of Salvia miltiorrhiza based on biogenic pathway of Tanshinones [J]. Chinese Journal of Traditional Chinese Medicine, 2020,45(13):3098-3103. 14. Zhang Yu, Qi Yingxue, Wang Lei, etc. Study on regional distribution characteristics of liposoluble components in Salvia miltiorrhiza in Shandong province [J]. Chinese herbal medicines, 2018, 041(011):2522-2526. 15. Liang conglian, Zhang Yongqing, Li Jia, et al. Comparative study on effective components of different strains of Salvia miltiorrhiza [J]. Shandong Science 2018(4):31-38. 16. Wei Guang Fei, Liu Qian, Li Jia, et al. Distribution of active components in root of Salvia miltiorrhiza [J]. Shandong Science 2015 28(05):7-13. 17. Minmin, Zhao, Zhiguo, Liu, Wei et al. Simultaneous determination of water-soluble and fat-soluble components in radix salviae Miltiorrhizae from three sources by HPLC-DAD method [J]. Shandong Science 2019(6). 18. Wang Yun, Chen Junfeng, Zhang Lei, et al. Evaluation of quality of Salvia miltiorrhiza Bunge based on association analysis of "active components-traits" [J]. World Science and Technology: modernization of traditional Chinese medicine, 2019(5):835-843. 19. Cui Weiliang. Comparison of the distribution of chromatographic peaks of HPLC fingerprint before and after the processing of Danshen wine [J]. Liaoning Journal of Traditional Chinese Medicine, v.46;No.507(08):1707-1709. 20. [IF = 7.514] tie Hua Zhang et al."In vitro and in siltiorrhiza." Food Chem. Jan 2019; 270:281 21. [IF = 7.514] Tong Wang et al."A hydrophobic deep eutectic solvents-based integrated method for efficient and green extraction and recovery of natural products from Rosmarinus officinalis leaves, Ginkgo biloba leaves and Salvia miltiorrhiza roots."Food Chem. 2021 Nov;3 22. [IF=4.411] Yuanyuan Li et al."Quantitative Determination and Validation of Four Ketones in Salvia miltiorrhiza Bunge Using Quantitative Proton Nuclear Magnetic Resonance Spectroscopy."Molecules. 2020 Jan;25(9):2043 23. [IF=3.411] Liu Hongyan et al."Effect Study of Continuous Monoculture on the Quality of Salvia miltiorrhiza Bge Roots."Biomed Res Int. 2020;2020:4284385 24. [IF=7.376] Chengtao Sun et al."Dihydrotanshinone I inhibits ovarian tumor growth by activating oxidative stress through Keap1-mediated Nrf2 ubiquitination degradation."Free Radical Bio Med. 2022 Feb;180:220 |
Dihydrotanshinone I 87205-99-0 - Reference Information
| overview | salvia miltiorrhiza is the dry root and rhizome of salvia miltiorrhiza (SalviamiltiorrhizaBunge), a labiatae plant, which was first recorded in Shennong's Materia Medica. Salvia miltiorrhiza is bitter in taste and slightly cold in nature. It has the traditional effects of promoting blood circulation and removing blood stasis, calming the mind and calming the heart. Phytochemical studies show that the chemical composition of Salvia miltiorrhiza mainly includes fat-soluble and water-soluble. Danshen ketones are the main fat-soluble components in Salvia miltiorrhiza. They are rosin-type diterpenoids with orange-yellow or orange-red characteristics. Pharmacological studies have proved that salvia miltiorrhiza ketones have antioxidant, antibacterial and anti-tumor effects. Dihydrotanshinone I(DihydrotanshinoneI, referred to as DHT) is a member of the tanshinone family. Its molecular formula is C18H14O3 and its molecular weight is 278.3. Studies have shown that DHT has anti-tumor and cardiovascular protective pharmacological activities. |
| application | dihydrotanshinone I is the extract of salvia miltiorrhiza rhizome. salvia miltiorrhiza is the most commonly used traditional Chinese medicine for promoting blood circulation and removing blood stasis in clinic. relevant literature reports that salvia miltiorrhiza has cardiovascular effects such as increasing coronary blood flow, dilating coronary arteries and preventing myocardial ischemia, and for the treatment of gastric cancer, liver cancer, cervical cancer and other diseases. Experiments show that dihydrotanshinone I(DHT) can effectively improve the general state of experimental ulcerative colitis mice, including weight loss, diarrhea, bloody stool and mental state, significantly improve pathological changes, significantly reduce inflammation, reduce the level of plasma inflammatory factors, etc., showing that DHT has obvious anti-ulcerative colitis effect. The advantages of dihydrotanshinone I in the treatment of ulcerative colitis are rapid action, definite curative effect and good efficacy. In addition, dihydrotanshinone I is a natural ingredient extracted from Salvia miltiorrhiza. There are no obvious side effects and toxic reactions during the experiment, which reveals that dihydrotanshinone I is a safe and effective anti-ulcerative colitis drug. |
| biological activity | Dihydrotanshinone I is a natural product isolated from salvia miltiorrhiza, which is widely used in the research of cardiovascular diseases. Dihydrotanshinone I can inhibit MERS-CoV. |
| in vitro study | 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. 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. |
| in vivo study | 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. 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. |
| chemical properties | red needle crystal, soluble in methanol, ethanol, DMSO and other organic solvents, derived from salvia miltiorrhiza. |
| use | antibacterial activity, inhibit hemolytic streptococcus, and improve heart function. used for content determination/identification/pharmacological experiment, etc. Pharmacological effect: antibacterial activity. The diameter of the bacteriostatic roll for 209 P of Staphylococcus aureus is 23mm (filter paper method), and the minimum inhibitory concentration for H↓ 37RV of human Mycobacterium tuberculosis is 1.5 μg/ml. It also has a certain inhibitory effect on hemolytic streptococcus |
| toxic substance data | The information is: pubchem.ncbi.nlm.nih.gov Provide (external link) |
Last Update：2024-04-09 20:52:54
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QQ: 2853786052
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