Tanshinone derivatives: A patent review (January 2006 - September 2012)

Expert Opinion on Therapeutic Patents

Volumn 23, Issue 1, 2013, Pages 19-29

  Tian, Xiao Hong ^a,b   Wu, Jian Hui ^a,b  

^a MCGILL UNIVERSITY   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

Anti atherosclerosis; Anti cancer; Cardioprotection; Danshen; Neuroprotection; Tanshinone IIA; Tanshinones

Indexed keywords

AMINO ACID TRANSPORTER; CASPASE 12; CASPASE 3; CRYPTOTANSHINONE; ENDOTHELIAL NITRIC OXIDE SYNTHASE; GELATINASE A; GROWTH ARREST AND DNA DAMAGE INDUCIBLE PROTEIN 153; MACROPHAGE MIGRATION INHIBITION FACTOR; MICRORNA 1; MITOGEN ACTIVATED PROTEIN KINASE; POTASSIUM TANSHINONE IIA SULFONATE; PROTEIN BAX; PROTEIN BCL 2; PROTEIN BCL XL; STRESS ACTIVATED PROTEIN KINASE; TANSHINONE I; TANSHINONE IIA; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ATHEROSCLEROSIS; BIOLOGICAL ACTIVITY; BONE MARROW CELL; BREAST CANCER; CANCER CELL; CASTRATION RESISTANT PROSTATE CANCER; CELL STRAIN HEPG2; CELL STRAIN LNCAP; CELL STRAIN MCF 7; CEREBROVASCULAR ACCIDENT; COLON CANCER; COLORECTAL CANCER; COMPARATIVE STUDY; DEGENERATIVE DISEASE; GLIOMA CELL; HEART ARRHYTHMIA; HEART INFARCTION; HEART MUSCLE CELL; HEART MUSCLE ISCHEMIA; HEART PROTECTION; HEART VENTRICLE HYPERTROPHY; HUMAN; HYPOXIC ISCHEMIC ENCEPHALOPATHY; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; LEUKEMIA CELL; LIVER CELL CARCINOMA; LUNG CANCER; MESENCHYMAL STEM CELL; MUSCLE CELL; MUSCLE ISCHEMIA; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; OSTEOSARCOMA CELL; OXIDATIVE STRESS; PANCREAS CANCER; PHEOCHROMOCYTOMA CELL; PROSTATE CANCER; PROTEIN EXPRESSION; REVIEW; STOMACH CANCER;

ANIMALS; ATHEROSCLEROSIS; CARDIOVASCULAR DISEASES; DITERPENES, ABIETANE; DRUG DESIGN; DRUGS, CHINESE HERBAL; HUMANS; NEOPLASMS; NEURODEGENERATIVE DISEASES; PATENTS AS TOPIC; PRODRUGS; SOLUBILITY;

EID: 84871490589     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2013.736494     Document Type: Review

References (89)

1. Wang BQ. Salvia miltiorrhiza: chemical and pharmacological review of a medicinal plant. J Med Plants Res 2010;4:2813-20
2. Jia Y, Huang F, Zhang S, Leung SW. Is danshen (Salvia miltiorrhiza) dripping pill more effective than isosorbide dinitrate in treating angina pectoris? A systematic review of randomized controlled trials. Int J Cardiol 2012;157:330-40
3. Zhao A, Han Y. Strategy for screening leading compounds from botanicals. China Pharm 2002;13:516-18
4. Wang X, Morris-Natschke SL, Lee KH. New developments in the chemistry and biology of the bioactive constituents of Tanshen. Med Res Rev 2007;27:133-48 (Pubitemid 44975189)
5. Zhou L, Zuo Z, Chow MSS. Danshen: an overview of its chemistry, pharmacology, pharmacokinetics, and clinical use. J Clin Pharmacol 2005;45:1345-59 (Pubitemid 41643896)
6. Cheng TO. Cardiovascular effects of danshen. Int J Cardiol 2007;121:9-22 (Pubitemid 47287779)
7. Chan P, Liu IM, Li YX, et al. Antihypertension induced by tanshinone IIA isolated from the roots of salvia miltiorrhiza. Evid Based Complement Alternat Med 2011;2011:1-8
8. Bi HC, Zuo Z, Chen X, et al. Preclinical factors affecting the pharmacokinetic behaviour of tanshinone IIA, an investigational new drug isolated from salvia miltiorrhiza for the treatment of ischaemic heart diseases. Xenobiotica 2008;38:185-222
9. Shanghai Cooperative Group for the Study of Tanshinone IIA. Therapeutic effect of sodium tanshinone IIA sulfonate in patients with coronary heart disease. A double blind study. J Tradit Chin Med 1984;4:20-4
10. Steinberg D. Low density lipoprotein oxidation and its pathobiological significance. J Biol Chem 1997;272:20963-6 (Pubitemid 27373946)
11. Galkina E, Ley K. Immune and inflammatory mechanisms of atherosclerosis. Annu Rev Immunol 2009;27:165-97
12. Sorescu D, Weiss D, Lassegue B, et al. Superoxide production and expression of nox family proteins in human atherosclerosis. Circulation 2002;105:1429-35 (Pubitemid 34263273)
13. Vendrov AE, Hakim ZS, Madamanchi NR, et al. Atherosclerosis is attenuated by limiting superoxide generation in both macrophages and vessel wall cells. Arterioscler Thromb Vasc Biol 2007;27:2714-21 (Pubitemid 350158927)
14. Chen W, Tang F, Xie B, et al. Amelioration of atherosclerosis by tanshinone IIA in hyperlipidemic rabbits through attenuation of oxidative stress. Eur J Pharmacol 2012;674:359-64
15. Fang Z, Lin R, Yuan B, et al. Tanshinone IIA downregulates the CD40 expression and decreases MMP-2 activity on atherosclerosis induced by high fatty diet in rabbit. J Ethnopharmacol 2008;115:217-22
16. Tang F, Wu X, Wang T, et al. Tanshinone II A attenuates atherosclerotic calcification in rat model by inhibition of oxidative stress. Vascul Pharmacol 2007;46:427-38 (Pubitemid 46552282)
17. Xu S, Little PJ, Lan T, et al. Tanshinone IIA attenuates and stabilizes atherosclerotic plaques in Apolipoprotein-E knockout mice fed a high cholesterol diet. Arch Biochem Biophys 2011;515:72-9
18. Tang FT, Cao Y, Wang TQ, et al. Tanshinone IIA attenuates atherosclerosis in ApoE -/- mice through down-regulation of scavenger receptor expression. Eur J Pharmacol 2011;650:275-84
19. Niu XL, Ichimori K, Yang X, et al. Tanshinone II-A inhibits low density lipoprotein oxidation in vitro. Free Radic Res 2000;33:305-12
20. Xu S, Liu Z, Huang Y, et al. Tanshinone II-A inhibits oxidized LDL-induced LOX-1 expression in macrophages by reducing intracellular superoxide radical generation and NF-kB activation. Transl Res 2012;160:114-24
21. Zhu H, Itoh K, Yamamoto M, et al. Role of Nrf2 signaling in regulation of antioxidants and phase 2 enzymes in cardiac fibroblasts: protection against reactive oxygen and nitrogen species-induced cell injury. FEBS Lett 2005;579:3029-36 (Pubitemid 40797830)
22. Zhang HS, Wang SQ. Nrf2 is involved in the effect of tanshinone IIA on intracellular redox status in human aortic smooth muscle cells. Biochem Pharmacol 2007;73:1358-66
23. Tan X, Li J, Wang X, et al. Tanshinone IIA protects against cardiac hypertrophy via inhibiting cal-cineurin/Nfatc3 pathway. Int J Biol Sci 2011;7:383-9
24. Shan H, Li X, Pan Z, et al. Tanshinone MA protects against sudden cardiac death induced by lethal arrhythmias via repression of microRNA-1. Br J Pharmacol 2009;158:1227-35
25. Pan C, Lou L, Huo Y, et al. Salvianolic acid B and tanshinone IIA attenuate myocardial ischemia injury in mice by no production through multiple pathways. Ther Adv Cardiovasc Dis 2011;5:99-111
26. Zhang Y, Zhang L, Chu W, et al. Tanshinone IIA inhibits miR-1 expression through p38 MAPK signal pathway in post-infarction rat cardiomyocytes. Cell Physiol Biochem 2010;26:991-8
27. Fan G, Zhu Y, Guo H, et al. Direct vasorelaxation by a novel phytoestrogen tanshinone IIA is mediated by nongenomic action of estrogen receptor through endothelial nitric oxide synthase activation and calcium mobilization. J Cardiovasc Pharmacol 2011;57:340-7
28. Yang B, Lin H, Xiao J, et al. The muscle-specific microRNA miR-1 regulates cardiac arrhythmogenic potential by targeting GJA1 and KCNJ2. Nat Med 2007;13:486-91 (Pubitemid 46559834)
29. Sun DD, Wang HC, Wang XB, et al. Tanshinone IIA: a new activator of human cardiac KCNQ1/KCNE1 (I Ks) potassium channels. Eur J Pharmacol 2008;590:317-21
30. Yang P, Jia YH, Li J, et al. Study of anti-myocardial cell oxidative stress action and effect of tanshinone IIA on prohibitin expression. J Tradit Chin Med 2010;30:259-64
31. Tong Y, Xu W, Han H, et al. Tanshinone IIA increases recruitment ofreceptor 4 axis in a myocardial ischemia model. Phytomedicine 2011;18:443-50
32. Chen Y, Wu X, Yu S, et al. Neuroprotection of tanshinone IIA against cerebral ischemia/reperfusion injury through inhibition of macrophage migration inhibitory factor in rats. PLoS ONE 2012;7(6):e40165
33. Liu L, Zhang X, Wang L, et al. The neuroprotective effects of tanshinone IIA are associated with induced nuclear translocation of TORC1 and upregulated expression of TORC1, pCREB and BDNF in the acute stage of ischemic stroke. Brain Res Bull 2010;82:228-33
34. Wang W, Zheng LL, Wang F, et al. Tanshinone IIA attenuates neuronal damage and the impairment of long-term potentiation induced by hydrogen peroxide. J Ethnopharmacol 2011;134:147-55
35. Chen Y, Wu X, Yu S, et al. Neuroprotective capabilities of tanshinone IIA against cerebral ischemia/ reperfusion injury via anti-apoptotic pathway in rats. Biol Pharm Bull 2012;35:164-70
36. Dong K, Xu W, Yang J, et al. Neuroprotective effects of Tanshinone IIA on permanent focal cerebral ischemia in mice. Phytother Res 2009;23:608-13
37. Qian YH, Xiao Q, Xu J. The protective effects of tanshinone IIA on +w-amyloid protein (1-42)-induced cytotoxicity via activation of the Bcl-xL pathway in neuron. Brain Res Bull 2012;88:354-8
38. Shi LL, Yang WN, Chen XL, et al. The protective effects of tanshinone IIA on neurotoxicity induced by beta-amyloid protein through calpain and the p35/ Cdk5 pathway in primary cortical neurons. Neurochem Int 2012;61:227-35
39. Dong HM, Mao SP, Wei JJ, et al. Tanshinone IIA protects PC12 cells from beta-amyloid(25-35)-induced apoptosis via PI3K/Akt signaling pathway. Mol Biol Rep 2012;39:6495-503
40. Sasaki T, Takemori H, Yagita Y, et al. SIK2 is a key regulator for neuronal survival after ischemia via TORC1-CREB. Neuron 2011;69:106-19
41. Inacio AR, Ruscher K, Leng L, et al. Macrophage migration inhibitory factor promotes cell death and aggravates neurologic deficits after experimental stroke. J Cereb Blood Flow Metab 2011;31:1093-106
42. Hei M, Luo Y, Zhang X, Liu F. Tanshinone IIa alleviates the biochemical changes associated with hypoxic ischemic brain damage in a rat model. Phytother Res 2011;25:1865-9
43. Patrick GN, Zukerberg L, Nikolic M, et al. Conversion of p35 to p25 deregulates Cdk5 activity and promotes neurodegeneration. Nature 1999;402:615-22 (Pubitemid 129516324)
44. Jiang P, Chen M, Lu J, et al. Effect of tanshinone II A on MMP-2 and iNOS expression and free radical release in hippocampus of rat Alzheimer's disease model. Acad J Second Mil Med Univ 2010;31:380-4
45. Dong Y, Morris-Natschke SL, Lee KH. Biosynthesis, total syntheses, and antitumor activity of tanshinones and their analogs as potential therapeutic agents. Nat Prod Rep 2011;28:529-42
46. Cheng CY, Su CC. Tanshinone IIA may inhibit the growth of small cell lung cancer H146 cells by up-regulating the Bax/Bcl-2 ratio and decreasing mitochondrial membrane potential. Mol Med Rep 2010;3:645-50
47. Chiu TL, Su CC. Tanshinone IIA induces apoptosis in human lung cancer A549 cells through the induction of reactive oxygen species and decreasing the mitochondrial membrane potential. Int J Mol Med 2010;25:231-6
48. Liu F, Yu G, Wang G, et al. An NQO1-initiated and p53-independent apoptotic pathway determines the anti-tumor effect of tanshinone. IIA against non-small cell lung cancer. PLoS One 2012;7(7):e42138
49. Won SH, Lee HJ, Jeong SJ, et al. Tanshinone IIA induces mitochondria dependent apoptosis in prostate cancer cells in association with an inhibition of phosphoinositide 3-kinase/AKT pathway. Biol Pharm Bull 2010;33:1828-34
50. Liu W, Zhou J, Geng G, et al. Antiandrogenic, maspin induction, and antiprostate cancer activities of tanshinone IIA and its novel derivatives with modification in ring A. J Med Chem 2012;55:971-5
51. Zhang Y, Won SH, Jiang C, et al. Tanshinones from Chinese medicinal herb Danshen (Salvia miltiorrhiza Bunge) suppress prostate cancer growth and androgen receptor signaling. Pharm Res 2012;29:1595-608
52. Taplin ME, Ho SM. The endocrinology of prostate cancer. J Clin Endocrinol Metab 2001;86:3467-77
53. Yan MY, Chien SY, Kuo SJ, et al. Tanshinone IIA inhibits BT-20 human breast cancer cell proliferation through increasing caspase 12, GADD153 and phospho-p38 protein expression. Int J Mol Med 2012;29:855-63
54. Su CC, Chien SY, Kuo SJ, et al. Tanshinone IIA inhibits human breast cancer MDA-MB-231cells by decreasing LC3-II, Erb-B2 and NF-+wBp65. Mol Med Rep 2012;5:1019-22
55. Xu CL, Xi T. Anti-migration and anti-angiogenic effects of tanshinone IIA on breast cancer cell MDA-MB-435. J China Pharm Univ 2009;40:565-70
56. Chien SY, Kuo SJ, Chen YL, et al. Tanshinone IIA inhibits human hepatocellular carcinoma J5 cell growth by increasing Bax and caspase 3 and decreasing CD31 expression in vivo. Mol Med Rep 2012;5:282-6
57. Xu YX, Tian F, Li R, Liu ZC. Tanshinone II-A inhibits invasion and metastasis of human hepatocellular carcinoma cells in vitro and in vivo. Tumori 2009;95:789-95
58. Xu Y, Tian F, Li R, Liu Z. Tanshinone H-A inhibits invasion and metastasis of human hepatocellular carcinoma cells in vitro and in vivo. Tumori 2009;95:789-95
59. Fu H, He SX, Xu JL, et al. Effect of tanshinone IIA on vascular endothelial growth factor expression in hepatocellular carcinoma cell line SMMC-7721. J Xian Jiaotong Univ (Medical Sciences) 2009;30:115-18
60. Wang Y, Li Q, Fan ZZ, et al. Tanshinone II A induces apoptosis of liver cancer cells via p38MAPK signal transduction. World Chin J Digestology 2009;17:124-9
61. Shan YF, Shen X, Xie YK, et al. Inhibitory effects of tanshinone II-A on invasion and metastasis of human colon bone marrow mesenchymal stem cells to infarct region via up-regulating stromal cell-derived factor-1/CXC chemokine carcinoma cells. Acta Pharmacol Sin 2009;30:1537-42
62. Su CC, Lin YH. Tanshinone IIA down-regulates the protein expression of ErbB-2 and up-regulates TNF-alpha in colon cancer cells in vitro and in vivo. Int J Mol Med 2008;22:847-51
63. Chen J, Zhong L, Qian LP, et al. Anticancer effects and mechanisms of tanshinone IIA sulfonic acid in nude mouse xenograft model bearing MKN-45 gastric cancer cells. World Chin J Digestology 2008;16:2507-11
64. Zhou LH, Liu X, Wang Y, et al. Tanshinone IIA inhibits angiogenesis in subcutaneous colorectal cancer xenografts in mice. World Chin J Digestology 2009;17:3203-9
65. Liu JJ, Lin DJ, Liu PQ, et al. Induction of apoptosis and inhibition of cell adhesive and invasive effects by tanshinone IIA in acute promyelocytic leukemia cells in vitro. J Biomed Sci 2006;13:813-23
66. Wang Y, Li Q, Fan ZZ, et al. Tanshinone IIA induces apoptosis of pancreatic cancer cells via the SAPK/JNK signal pathway. World Chin J Digestology 2011;19:1028-33
67. Zhang Y, Wei RX, Zhu XB, et al. Tanshinone IIA induces apoptosis and inhibits the proliferation, migration, and invasion of the osteosarcoma MG-63 cell line in vitro. Anticancer Drugs 2012;23:212-19
68. Tang C, Xue HL, Huang HB, Wang XG. Tanshinone IIA inhibits constitutive STAT3 activation, suppresses proliferation, and induces apoptosis in rat C6 glioma cells. Neurosci Lett 2010;470:126-9
69. Pan TL, Hung YC, Wang PW, et al. Functional proteomic and structural insights into molecular targets related to the growth inhibitory effect of tanshinone IIA on HeLa cells. Proteomics 2010;10:914-29
70. Zhang Z, Gao J, Wang Y, et al. Tanshinone IIA triggers p53 responses and apoptosis by RNA polymerase II upon DNA minor groove binding. Biochem Pharmacol 2009;78:1316-22
71. Zhang Z, Zhang J, Jin L, et al. Tanshinone IIA interacts with DNA by minor groove-binding. Biol Pharm Bull 2008;31:2342-5
72. Soares J, Keppler BR, Wang X, et al. Ortho-Quinone tanshinones directly inhibit telomerase through an oxidative mechanism mediated by hydrogen peroxide. Bioorg Med Chem Lett 2011;21:7474-8
73. Tsai MY, Yang RC, Wu HT, et al. Anti-angiogenic effect of tanshinone IIA involves inhibition of matrix invasion and modification of MMP-2/TIMP- 2 secretion in vascular endothelial cells. Cancer Lett 2011;310:198-206
74. Zhou LH, Wang Y, Fan ZZ, et al. Tan IIA inhibits COX-2-regulated VEGF expression in human colon cancer HCT-116 cells. World Chin J Digestology 2011;19:1561-7
75. Qin YL. Hydroxy tanshinone IIA sodium sulfonate and its application. CN1844113A; 2006
76. Huang ZH, Ju S, Chen JT. 3-hydroxytanshinone IIA sodium sulfonate as well as preparation method and application. CN102002092A; 2011
77. Liu XH. Tanshinone IIA potassium sulfonate used for preparing medicine for preventing and treating cerebral ischemia and cerebral anoxia and myocardial ischemia and myocardio anoxia. CN101070338A; 2007
78. Qin YL, Xie P, Zhang Q, et al. Class I tanshinone II A derivative and its application in pharmaceutic. CN1955170A; 2007
79. Qin YL, Xia P, Zhang Q, et al. Tanshinon IIA crylic acid or sodium salt thereof, preparation method and application thereof. CN101974068A; 2011
80. Qin YL. Tanshinone I derivatives and pharmaceutical application thereof. CN1837200; 2006
81. Qin YL. Tanshinone IIA derivatives and pharmaceutical application thereof. CN1837198A; 2006
82. Li J, Liu W, Juang WG, et al. Naphthofurans ortho-quinone compound, preparation and use thereof. CN101274925; 2008
83. Mei WJ, Yin P. Tanshinone II A derivative and preparation method and application thereof. CN101863894A; 2012
84. Don MJ, Shen CC, Lin YL, et al. Nitrogen-containing compounds from salvia miltiorrhiza. J Nat Prod 2005;68:1066-70
85. An LK, Zhang DL, Cheng X, et al. Niacin salvia miltiorrhiza phenolic ester derivative, preparation method and application thereof. CN102079774A; 2011
86. Wang X, Bastow KF, Sun CM, et al. Antitumor Agents. 239. Isolation, structure elucidation, total synthesis, and anti-breast cancer activity of neo-tanshinlactone from salvia miltiorrhiza. J Med Chem 2004;47:5816-19 (Pubitemid 39447277)
87. Lee KH, Wang XH, Bastow KF, et al. Neo-tanshinlactone and analogs as potent and selective anti-breast cancer agents. US20090118356A1; 2009
88. Wang X, Nakagawa-Goto K, Bastow KF, et al. Antitumor agents. 254. Synthesis and biological evaluation of novel neo-tanshinlactone analogues as potent anti-breast cancer agents. J Med Chem 2006;49:5631-4 (Pubitemid 44373195)
89. Kwak TW, Yoo SK, Park MG. Compound for treatment or prevention of prostate-related diseases and pharmaceutical composition of colon delivery system containing the same. WO2008066298A1; 2008