Review Article

丹参酮:近 5 年药物化学进展

卷 28, 期 14, 2021

发表于: 21 May, 2020

页: [2807 - 2827] 页: 21

弟呕挨: 10.2174/0929867327666200521124850

价格: $65

摘要

丹参酮是从丹参中分离得到的一种重要的天然产物,具有多种生物活性。 丹参酮Ⅱa、隐丹参酮和丹参酮Ⅰ是被广泛研究的三种丹参酮。 特别是丹参酮Ⅱa磺酸钠是丹参酮Ⅱa的水溶性衍生物,在我国临床上用于治疗心血管疾病。 近年来,丹参酮衍生物在各种疾病中的研究越来越受到关注。 本文综述了近年来丹参酮的抗动脉粥样硬化作用、心脏保护作用、抗癌活性、抗菌活性和抗病毒活性以及结构修饰工作。

关键词: 丹参酮、结构修饰、抗动脉粥样硬化作用、心脏保护作用、抗癌活性、抗菌活性、抗病毒活性。

[1]
Mohammadhosseini, M.; Pazoki, A.; Akhlaghi, H. Chemical composition of the essential oils from flowers, stems, and roots of Salvia multicaulis growing wild in Iran. Chem. Nat. Compd., 2008, 44, 127-128.
[http://dx.doi.org/10.1007/s10600-008-0039-3]
[2]
Vallejo, M.C.G.; Moujir, L.; Burillo, J.; Guerra, L.L.; González, M.; Peñate, R.D.; Andrés, L.S.; Luis, J.G.; Blanco, F.L.; de Galarreta, C.M. Ruiz. Chemical composition and biological activities of the essential oils of Salvia canariensis. Flavour Fragrance J., 2006, 21, 72-76.
[http://dx.doi.org/10.1002/ffj.1504]
[3]
Wu, Y.B.; Ni, Z.Y.; Shi, Q.W.; Dong, M.; Kiyota, H.; Gu, Y.C.; Cong, B. Constituents from Salvia species and their biological activities. Chem. Rev., 2012, 112(11), 5967-6026.
[http://dx.doi.org/10.1021/cr200058f] [PMID: 22967178]
[4]
Wang, B. Salvia miltiorrhiza: Chemical and pharmacological review of a medicinal plant. J. Med. Plants Res., 2010, 4, 2813-2821.
[5]
Zhou, L.; Zuo, Z.; Chow, M.S.S. Danshen: an overview of its chemistry, pharmacology, pharmacokinetics, and clinical use. J. Clin. Pharmacol., 2005, 45(12), 1345-1359.
[http://dx.doi.org/10.1177/0091270005282630] [PMID: 16291709]
[6]
Chen, X.; Guo, J.; Bao, J.; Lu, J.; Wang, Y. The anticancer properties of Salvia miltiorrhiza Bunge (Danshen): a systematic review. Med. Res. Rev., 2014, 34(4), 768-794.
[http://dx.doi.org/10.1002/med.21304] [PMID: 24123144]
[7]
Li, Z.M.; Xu, S.W.; Liu, P.Q. Salvia miltiorrhiza Burge (Danshen): a golden herbal medicine in cardiovascular therapeutics. Acta Pharmacol. Sin., 2018, 39(5), 802-824.
[http://dx.doi.org/10.1038/aps.2017.193] [PMID: 29698387]
[8]
Dong, Y.; Morris-Natschke, S.L.; Lee, K.H. Biosynthesis, total syntheses, and antitumor activity of tanshinones and their analogs as potential therapeutic agents. Nat. Prod. Rep., 2011, 28(3), 529-542.
[http://dx.doi.org/10.1039/c0np00035c] [PMID: 21225077]
[9]
Tian, X.H.; Wu, J.H. Tanshinone derivatives: a patent review (January 2006 - September 2012). Expert Opin. Ther. Pat., 2013, 23(1), 19-29.
[http://dx.doi.org/10.1517/13543776.2013.736494] [PMID: 23094864]
[10]
Du, J.R.; Li, X.; Zhang, R.; Qian, Z.M. Tanshinone inhibits intimal hyperplasia in the ligated carotid artery in mice. J. Ethnopharmacol., 2005, 98(3), 319-322.
[http://dx.doi.org/10.1016/j.jep.2005.01.038] [PMID: 15814266]
[11]
Li, X.; Du, J.R.; Yu, Y.; Bai, B.; Zheng, X.Y. Tanshinone IIA inhibits smooth muscle proliferation and intimal hyperplasia in the rat carotid balloon-injured model through inhibition of MAPK signaling pathway. J. Ethnopharmacol., 2010, 129(2), 273-279.
[http://dx.doi.org/10.1016/j.jep.2010.03.021] [PMID: 20363310]
[12]
Chen, W.; Tang, F.; Xie, B.; Chen, S.; Huang, H.; Liu, P. Amelioration of atherosclerosis by tanshinone IIA in hyperlipidemic rabbits through attenuation of oxidative stress. Eur. J. Pharmacol., 2012, 674(2-3), 359-364.
[http://dx.doi.org/10.1016/j.ejphar.2011.10.040] [PMID: 22088276]
[13]
Fang, Z.Y.; Lin, R.; Yuan, B.X.; Liu, Y.; Zhang, H. Tanshinone IIA inhibits atherosclerotic plaque formation by down-regulating MMP-2 and MMP-9 expression in rabbits fed a high-fat diet. Life Sci., 2007, 81(17-18), 1339-1345.
[http://dx.doi.org/10.1016/j.lfs.2007.08.043] [PMID: 17942126]
[14]
Liu, X.; Guo, C.Y.; Ma, X.J.; Wu, C.F.; Zhang, Y.; Sun, M.Y.; Pan, Y.T.; Yin, H.J. Anti-inflammatory effects of tanshinone IIA on atherosclerostic vessels of ovariectomized ApoE mice are mediated by estrogen receptor activation and through the ERK signaling pathway. Cell. Physiol. Biochem., 2015, 35(5), 1744-1755.
[http://dx.doi.org/10.1159/000373986 ] [PMID: 25832326]
[15]
Liu, Z.; Wang, J.; Huang, E.; Gao, S.; Li, H.; Lu, J.; Tian, K.; Little, P.J.; Shen, X.; Xu, S.; Liu, P. Tanshinone IIA suppresses cholesterol accumulation in human macrophages: role of heme oxygenase-1. J. Lipid Res., 2014, 55(2), 201-213.
[http://dx.doi.org/10.1194/jlr.M040394] [PMID: 24302760]
[16]
Tang, F.; Wu, X.; Wang, T.; Wang, P.; Li, R.; Zhang, H.; Gao, J.; Chen, S.; Bao, L.; Huang, H.; Liu, P. Tanshinone II A attenuates atherosclerotic calcification in rat model by inhibition of oxidative stress. Vascul. Pharmacol., 2007, 46(6), 427-438.
[http://dx.doi.org/10.1016/j.vph.2007.01.001] [PMID: 17337361]
[17]
Tang, F.T.; Cao, Y.; Wang, T.Q.; Wang, L.J.; Guo, J.; Zhou, X.S.; Xu, S.W.; Liu, W.H.; Liu, P.Q.; Huang, H.Q. Tanshinone IIA attenuates atherosclerosis in ApoE(-/-) mice through down-regulation of scavenger receptor expression. Eur. J. Pharmacol., 2011, 650(1), 275-284.
[http://dx.doi.org/10.1016/j.ejphar.2010.07.038] [PMID: 20854809]
[18]
Xu, S.; Little, P.J.; Lan, T.; Huang, Y.; Le, K.; Wu, X.; Shen, X.; Huang, H.; Cai, Y.; Tang, F.; Wang, H.; Liu, P. Tanshinone II-A attenuates and stabilizes atherosclerotic plaques in apolipoprotein-E knockout mice fed a high cholesterol diet. Arch. Biochem. Biophys., 2011, 515(1-2), 72-79.
[http://dx.doi.org/10.1016/j.abb.2011.08.006] [PMID: 21889487]
[19]
Xu, S.; Liu, Z.; Huang, Y.; Chen, J.; Chen, S.; Shen, X.; Huang, H.; Liu, P. Effectiveness of combination therapy of atorvastatin and non-lipid-modifying tanshinone IIA from Danshen in a mouse model of atherosclerosis. Int. J. Cardiol., 2014, 174(3), 878-880.
[http://dx.doi.org/10.1016/j.ijcard.2014.04.226] [PMID: 24814901]
[20]
Zhao, D.; Tong, L.; Zhang, L.; Li, H.; Wan, Y.; Zhang, T. Tanshinone II A stabilizes vulnerable plaques by suppressing RAGE signaling and NF-κB activation in apolipoprotein-E-deficient mice. Mol. Med. Rep., 2016, 14(6), 4983-4990.
[http://dx.doi.org/10.3892/mmr.2016.5916] [PMID: 27840935]
[21]
Zhu, J.; Xu, Y.; Ren, G.; Hu, X.; Wang, C.; Yang, Z.; Li, Z.; Mao, W.; Lu, D.; Tanshinone, I.I.A. Tanshinone IIA Sodium sulfonate regulates antioxidant system, inflammation, and endothelial dysfunction in atherosclerosis by downregulation of CLIC1. Eur. J. Pharmacol., 2017, 815, 427-436.
[http://dx.doi.org/10.1016/j.ejphar.2017.09.047] [PMID: 28970012]
[22]
Shang, T.; Liu, Z.; Zhou, M.; Zarins, C.K.; Xu, C.; Liu, C.J. Inhibition of experimental abdominal aortic aneurysm in a rat model by way of tanshinone IIA. J. Surg. Res., 2012, 178(2), 1029-1037.
[http://dx.doi.org/10.1016/j.jss.2012.04.068] [PMID: 22640888]
[23]
Niu, X.L.; Ichimori, K.; Yang, X.; Hirota, Y.; Hoshiai, K.; Li, M.; Nakazawa, H. Tanshinone II-A inhibits low density lipoprotein oxidation in vitro. Free Radic. Res., 2000, 33(3), 305-312.
[http://dx.doi.org/10.1080/10715760000301471] [PMID: 10993484]
[24]
Bi, X.; Zhang, K.; He, L.; Gao, B.; Gu, Q.; Li, X.; Chen, J.; Wang, J. Synthesis and biological evaluation of tanshinone IIA derivatives as novel endothelial protective agents. Future Med. Chem., 2017, 9(10), 1073-1085.
[http://dx.doi.org/10.4155/fmc-2016-0241] [PMID: 28632415]
[25]
Chang, C.C.; Chu, C.F.; Wang, C.N.; Wu, H.T.; Bi, K.W.; Pang, J.H.S.; Huang, S.T. The anti-atherosclerotic effect of tanshinone IIA is associated with the inhibition of TNF-α-induced VCAM-1, ICAM-1 and CX3CL1 expression. Phytomedicine, 2014, 21, 207-216.
[http://dx.doi.org/10.1016/j.phymed.2013.09.012 ] [PMID: 24157079]
[26]
Nizamutdinova, I.T.; Kim, Y.M.; Jin, H.; Son, K.H.; Lee, J.H.; Chang, K.C.; Kim, H.J. Tanshinone IIA inhibits TNF-α-mediated induction of VCAM-1 but not ICAM-1 through the regulation of GATA-6 and IRF-1. Int. Immunopharmacol., 2012, 14(4), 650-657.
[http://dx.doi.org/10.1016/j.intimp.2012.09.017] [PMID: 23085565]
[27]
Tang, C.; Xue, H.L.; Bai, C-L.; Fu, R. Regulation of adhesion molecules expression in TNF-α-stimulated brain microvascular endothelial cells by tanshinone IIA: involvement of NF-κB and ROS generation. Phytother. Res., 2011, 25(3), 376-380.
[http://dx.doi.org/10.1002/ptr.3278] [PMID: 20687137]
[28]
Li, Y.H.; Xu, Q.; Xu, W.H.; Guo, X.H.; Zhang, S.; Chen, Y-D. Mechanisms of protection against diabetes-induced impairment of endothelium-dependent vasorelaxation by Tanshinone IIA. Biochim. Biophys. Acta, 2015, 1850(4), 813-823.
[http://dx.doi.org/10.1016/j.bbagen.2015.01.007] [PMID: 25613563]
[29]
Chen, L.; Guo, Q.H.; Chang, Y.; Zhao, Y.S.; Li, A.Y.; Ji, E.S. Tanshinone IIA ameliorated endothelial dysfunction in rats with chronic intermittent hypoxia. J. Soc. Cardiovasc. Pathol., 2017, 31, 47-53.
[http://dx.doi.org/10.1016/j.carpath.2017.06.008] [PMID: 28985491]
[30]
Zhou, Z.W.; Xie, X.L.; Zhou, S.F.; Li, C.G. Mechanism of reversal of high glucose-induced endothelial nitric oxide synthase uncoupling by tanshinone IIA in human endothelial cell line EA.hy926. Eur. J. Pharmacol., 2012, 697(1-3), 97-105.
[http://dx.doi.org/10.1016/j.ejphar.2012.09.051] [PMID: 23063542]
[31]
Maione, F.; De Feo, V.; Caiazzo, E.; De Martino, L.; Cicala, C.; Mascolo, N. Tanshinone IIA, a major component of Salvia milthorriza Bunge, inhibits platelet activation via Erk-2 signaling pathway. J. Ethnopharmacol., 2014, 155(2), 1236-1242.
[http://dx.doi.org/10.1016/j.jep.2014.07.010] [PMID: 25038434]
[32]
Wang, Y.; Li, J.X.; Wang, Y.Q.; Miao, Z.H. Tanshinone I inhibits tumor angiogenesis by reducing Stat3 phosphorylation at Tyr705 and hypoxia-induced HIF-1α accumulation in both endothelial and tumor cells. Oncotarget, 2015, 6(18), 16031-16042.
[http://dx.doi.org/10.18632/oncotarget.3648] [PMID: 26202747]
[33]
Huang, B.; Zhou, Z.Y.; Li, S.; Huang, X.H.; Tang, J.Y.; Hoi, M.P.M.; Lee, S.M.Y. Tanshinone I prevents atorvastatin-induced cerebral hemorrhage in zebrafish and stabilizes endothelial cell-cell adhesion by inhibiting VE-cadherin internalization and actin-myosin contractility. Pharmacol. Res., 2018, 128, 389-398.
[http://dx.doi.org/10.1016/j.phrs.2017.09.025] [PMID: 29017932]
[34]
Ahmad, Z.; Ng, C.T.; Fong, L.Y.; Bakar, N.A.A.; Hussain, N.H.M.; Ang, K.P.; Ee, G.C.L.; Hakim, M.N. Cryptotanshinone inhibits TNF-α-induced early atherogenic events in vitro. J. Physiol. Sci., 2016, 66(3), 213-220.
[http://dx.doi.org/10.1007/s12576-015-0410-7] [PMID: 26732386]
[35]
Liu, Z.; Xu, S.; Huang, X.; Wang, J.; Gao, S.; Li, H.; Zhou, C.; Ye, J.; Chen, S.; Jin, Z.G.; Liu, P. Cryptotanshinone, an orally bioactive herbal compound from Danshen, attenuates atherosclerosis in apolipoprotein E-deficient mice: role of lectin-like oxidized LDL receptor-1 (LOX-1). Br. J. Pharmacol., 2015, 172(23), 5661-5675.
[http://dx.doi.org/10.1111/bph.13068] [PMID: 25572313]
[36]
Zhao, W.; Wu, C.; Chen, X. Cryptotanshinone inhibits oxidized LDL-induced adhesion molecule expression via ROS dependent NF-κB pathways. Cell Adhes. Migr., 2016, 10(3), 248-258.
[http://dx.doi.org/10.1080/19336918.2015.1119361] [PMID: 26647279]
[37]
Suh, S.J.; Jin, U.H.; Choi, H.J.; Chang, H.W.; Son, J.K.; Lee, S.H.; Jeon, S.J.; Son, K.H.; Chang, Y.C.; Lee, Y.C.; Kim, C.H. Cryptotanshinone from Salvia miltiorrhiza BUNGE has an inhibitory effect on TNF-alpha-induced matrix metalloproteinase-9 production and HASMC migration via down-regulated NF-kappaB and AP-1. Biochem. Pharmacol., 2006, 72(12), 1680-1689.
[http://dx.doi.org/10.1016/j.bcp.2006.08.013] [PMID: 16999937]
[38]
Ma, S.; Zhang, D.; Lou, H.; Sun, L.; Ji, J. Evaluation of the anti-inflammatory activities of tanshinones isolated from Salvia miltiorrhiza var. alba roots in THP-1 macrophages. J. Ethnopharmacol., 2016, 188, 193-199.
[http://dx.doi.org/10.1016/j.jep.2016.05.018] [PMID: 27178632]
[39]
Zhou, G.; Jiang, W.; Zhao, Y.; Ma, G.; Xin, W.; Yin, J.; Zhao, B. Sodium tanshinone IIA sulfonate mediates electron transfer reaction in rat heart mitochondria. Biochem. Pharmacol., 2003, 65(1), 51-57.
[http://dx.doi.org/10.1016/S0006-2952(02)01447-8] [PMID: 12473378 ]
[40]
Wei, B.; You, M.G.; Ling, J.J.; Wei, L.L.; Wang, K.; Li, W.W.; Chen, T.; Du, Q.M.; Ji, H. Regulation of antioxidant system, lipids and fatty acid β-oxidation contributes to the cardioprotective effect of sodium tanshinone IIA sulphonate in isoproterenol-induced myocardial infarction in rats. Atherosclerosis, 2013, 230(1), 148-156.
[http://dx.doi.org/10.1016/j.atherosclerosis.2013.07.005] [PMID: 23958267]
[41]
Hu, Q.; Wei, B.; Wei, L.; Hua, K.; Yu, X.; Li, H.; Ji, H. Sodium tanshinone IIA sulfonate ameliorates ischemia-induced myocardial inflammation and lipid accumulation in Beagle dogs through NLRP3 inflammasome. Int. J. Cardiol., 2015, 196, 183-192.
[http://dx.doi.org/10.1016/j.ijcard.2015.05.152] [PMID: 26143630]
[42]
Ren, Z.H.; Tong, Y.H.; Xu, W.; Ma, J.; Chen, Y. Tanshinone II A attenuates inflammatory responses of rats with myocardial infarction by reducing MCP-1 expression. Phytomedicine, 2010, 17(3-4), 212-218.
[http://dx.doi.org/10.1016/j.phymed.2009.08.010] [PMID: 19800776]
[43]
Gu, Y.; Liang, Z.; Wang, H.; Jin, J.; Zhang, S.; Xue, S.; Chen, J.; He, H.; Duan, K.; Wang, J.; Chang, X.; Qiu, C. Tanshinone IIA protects H9c2 cells from oxidative stress-induced cell death via microRNA-133 upregulation and Akt activation. Exp. Ther. Med., 2016, 12(2), 1147-1152.
[http://dx.doi.org/10.3892/etm.2016.3400] [PMID: 27446335]
[44]
Yang, R.; Liu, A.; Ma, X.; Li, L.; Su, D.; Liu, J. Sodium tanshinone IIA sulfonate protects cardiomyocytes against oxidative stress-mediated apoptosis through inhibiting JNK activation. J. Cardiovasc. Pharmacol., 2008, 51(4), 396-401.
[http://dx.doi.org/10.1097/FJC.0b013e3181671439] [PMID: 18427283]
[45]
Shan, H.; Li, X.; Pan, Z.; Zhang, L.; Cai, B.; Zhang, Y.; Xu, C.; Chu, W.; Qiao, G.; Li, B.; Lu, Y.; Yang, B. Tanshinone IIA protects against sudden cardiac death induced by lethal arrhythmias via repression of microRNA-1. Br. J. Pharmacol., 2009, 158(5), 1227-1235.
[http://dx.doi.org/10.1111/j.1476-5381.2009.00377.x] [PMID: 19775284]
[46]
Jin, H.J.; Xie, X.L.; Ye, J.M.; Li, C.G. TanshinoneIIA and cryptotanshinone protect against hypoxia-induced mitochondrial apoptosis in H9c2 cells. PLoS One, 2013, 8(1)e51720
[http://dx.doi.org/10.1371/journal.pone.0051720] [PMID: 23341883]
[47]
Hong, H.J.; Liu, J.C.; Cheng, T.H.; Chan, P. Tanshinone IIA attenuates angiotensin II-induced apoptosis via Akt pathway in neonatal rat cardiomyocytes. Acta Pharmacol. Sin., 2010, 31(12), 1569-1575.
[http://dx.doi.org/10.1038/aps.2010.176] [PMID: 21102479]
[48]
Wei, B.; Li, W.W.; Ji, J.; Hu, Q.H.; Ji, H. The cardioprotective effect of sodium tanshinone IIA sulfonate and the optimizing of therapeutic time window in myocardial ischemia/reperfusion injury in rats. Atherosclerosis, 2014, 235(2), 318-327.
[http://dx.doi.org/10.1016/j.atherosclerosis.2014.05.924] [PMID: 24911635]
[49]
Hu, H.; Zhai, C.; Qian, G.; Gu, A.; Liu, J.; Ying, F.; Xu, W.; Jin, D.; Wang, H.; Hu, H.; Zhang, Y.; Tang, G. Protective effects of tanshinone IIA on myocardial ischemia reperfusion injury by reducing oxidative stress, HMGB1 expression, and inflammatory reaction. Pharm. Biol., 2015, 53(12), 1752-1758.
[http://dx.doi.org/10.3109/13880209.2015.1005753] [PMID: 25864557]
[50]
Zhang, Y.; Wei, L.; Sun, D.; Cao, F.; Gao, H.; Zhao, L.; Du, J.; Li, Y.; Wang, H. Tanshinone IIA pretreatment protects myocardium against ischaemia/reperfusion injury through the phosphatidylinositol 3-kinase/Akt-dependent pathway in diabetic rats. Diabetes Obes. Metab., 2010, 12(4), 316-322.
[http://dx.doi.org/10.1111/j.1463-1326.2009.01166.x] [PMID: 20380652]
[51]
Pan, Y.; Qian, J.X.; Lu, S.Q.; Chen, J.W.; Zhao, X.D.; Jiang, Y.; Wang, L-H.; Zhang, G-X. Protective effects of tanshinone IIA sodium sulfonate on ischemia-reperfusion-induced myocardial injury in rats. Iran. J. Basic Med. Sci., 2017, 20(3), 308-315.
[http://dx.doi.org/10.22038/ijbms.2017.8361] [PMID: 28392904]
[52]
Zhang, M.Q.; Zheng, Y.L.; Chen, H.; Tu, J.F.; Shen, Y.; Guo, J.P.; Yang, X.H.; Yuan, S.R.; Chen, L.Z.; Chai, J.J.; Lu, J.H.; Zhai, C.L. Sodium tanshinone IIA sulfonate protects rat myocardium against ischemia-reperfusion injury via activation of PI3K/Akt/FOXO3A/Bim pathway. Acta Pharmacol. Sin., 2013, 34(11), 1386-1396.
[http://dx.doi.org/10.1038/aps.2013.91] [PMID: 24077633]
[53]
Zhang, M.Q.; Tu, J.F.; Chen, H.; Shen, Y.; Pang, L.X.; Yang, X.H.; Sun, R.H.; Zheng, Y.L. Janus kinase/signal transducer and activator of transcription inhibitors enhance the protective effect mediated by tanshinone IIA from hypoxic/ischemic injury in cardiac myocytes. Mol. Med. Rep., 2015, 11(4), 3115-3121.
[http://dx.doi.org/10.3892/mmr.2014.3063] [PMID: 25502794]
[54]
Fu, Y.; Chen, J. Synthesis and application of sulfonamide compounds. Patent number: CN104341481A, 2015.
[55]
Fu, Y.; Chen, J. Synthesis and pharmaceutical application of sulfamide derivative. CN104341450A, 2015 11February;
[56]
Wang, J.; Chen, J.; He, L. Use of tanshinone IIA derivatives in preparation of drug for protecting endothelial cells. Patent number: CN105837538A, 2016.
[57]
Ding, L.; Wang, J.; Huang, Z. Application of tanshinone II A derivative in drugs. Patent number: CN105884856A, 2016.
[58]
Chen, J. Tanshinone IIA phosphoric acid derivative and synthesis and use thereof as medicine. Patent number: CN106478764A, 2017.
[59]
Chen, J. Sulfotanshinone IIA derivatives, and synthesis and applications thereof as drug. Patent number: CN106478765A, 2017.
[60]
Bi, Y.; Wang, Z. Danproone compound 15-site amide derivative, and preparation process and application thereof. Patent number: CN106831934A, 2017.
[61]
Sun, Q.; Zhang, W.; Yuan, H. Water-soluble tanshinone II A derivative, preparation and application thereof. Patent number: CN107540725A, 2018.
[62]
Qin, Y.L.; Chen, L.; He, W.; Su, M.; Jin, Q.; Fang, Z.; Ouyang, P.K.; Guo, K. Continuous synthesis and anti-myocardial injury of tanshinone IIA derivatives. J. Asian Nat. Prod. Res., 2018, 20(2), 139-147.
[http://dx.doi.org/10.1080/10286020.2017.1337751] [PMID: 28595458]
[63]
Su, M.; Wang, W. Tanshinone IIA derivative and preparation method thereof. Patent number: CN107663224A, 2018.
[64]
Tan, H.; Li, W.; Tang, A. Synthesis and application of tanshinone IIA derivatives. Patent number: CN109369771A, 2019.
[65]
Song, W.Y.; Liu, Y.; Yu, W.; Mu, J.; Yin, B.; Zuo, C.; Wei, H.; Zhang, R. Tanshinone IIA piperazine compounds as well as preparation method and application thereof. Patent number: CN110016069A, 2019.
[66]
Gimbrone, M.A. Jr; García-Cardeña, G. Endothelial cell dysfunction and the Pathobiology of atherosclerosis. Circ. Res., 2016, 118(4), 620-636.
[http://dx.doi.org/10.1161/CIRCRESAHA.115.306301] [PMID: 26892962]
[67]
Huang, C.S.; Song, Y.R.; Huang, Q. L. Tanshinone IIA thiophene pyridine compound and preparation method and application thereof Tanshinone IIA thiophene pyridine compound and preparation method and application thereof. Patent number: CN110066310A, 2019.
[68]
Zhang, B.; Shi, L.; Liu, S.; Guo, R. Tanshinone IIA derivate comprising polyethylene glycol group and preparation and application of tanshinone IIA derivate. Patent number: CN105037484A, 2015.
[69]
Wang, J.; Gong, Z. Application of tanshinone IIA derivative in preparation of ischemic stroke drugs. Patent number: CN109908154A, 2019.
[70]
Zhang, Q.; Zhu, Y.; Liu, X.; Zhou, Y. 9-hydroxytanshinone IIA sodium sulfonate ester derivative and medicinal use thereof. Patent number: CN104974216A, 2015.
[71]
Bi, Y.; Wang, Y.; Wu, Z.; Yang, X. 1-tanshinone acid ester derivatives with cardioprotective effect and application of 1- tanshinone acid ester derivatives. Patent number: CN106800582A, 2017.
[72]
Zhao, Y.P.; Wang, F.; Jiang, W.; Liu, J.; Liu, B.L.; Qi, L.W.; Zhou, W. A mitochondrion-targeting tanshinone IIA derivative attenuates myocardial hypoxia reoxygenation injury through a SDH-dependent antioxidant mechanism. J. Drug Target., 2019, 27(8), 896-902.
[http://dx.doi.org/10.1080/1061186X.2019.1566338] [PMID: 30632415]
[73]
Nizamutdinova, I.T.; Lee, G.W.; Son, K.H.; Jeon, S.J.; Kang, S.S.; Kim, Y.S.; Lee, J.H.; Seo, H.G.; Chang, K.C.; Kim, H.J. Tanshinone I effectively induces apoptosis in estrogen receptor-positive (MCF-7) and estrogen receptor-negative (MDA-MB-231) breast cancer cells. Int. J. Oncol., 2008, 33(3), 485-491.
[PMID: 18695877]
[74]
Wang, L.; Wu, J.; Lu, J.; Ma, R.; Sun, D.; Tang, J. Regulation of the cell cycle and PI3K/Akt/mTOR signaling pathway by tanshinone I in human breast cancer cell lines. Mol. Med. Rep., 2015, 11(2), 931-939.
[http://dx.doi.org/10.3892/mmr.2014.2819] [PMID: 25355053]
[75]
Su, C.C.; Chen, G-W.; Lin, J-G. Growth inhibition and apoptosis induction by tanshinone I in human colon cancer Colo 205 cells. Int. J. Mol. Med., 2008, 22(5), 613-618.
[PMID: 18949381]
[76]
Lee, C.Y.; Sher, H.F.; Chen, H.W.; Liu, C.C.; Chen, C.H.; Lin, C.S.; Yang, P.C.; Tsay, H.S.; Chen, J.J.W. Anticancer effects of tanshinone I in human non-small cell lung cancer. Mol. Cancer Ther., 2008, 7(11), 3527-3538.
[http://dx.doi.org/10.1158/1535-7163.MCT-07-2288] [PMID: 19001436]
[77]
Liu, X.D.; Fan, R.F.; Zhang, Y.; Yang, H.Z.; Fang, Z.G.; Guan, W-B.; Lin, D.J.; Xiao, R.Z.; Huang, R.W.; Huang, H.Q.; Liu, P.Q.; Liu, J.J. Down-regulation of telomerase activity and activation of caspase-3 are responsible for Tanshinone I-induced apoptosis in monocyte leukemia cells in vitro. Int. J. Mol. Sci., 2010, 11(6), 2267-2280.
[http://dx.doi.org/10.3390/ijms11062267] [PMID: 20640151]
[78]
Shin, E.A.; Sohn, E.J.; Won, G.; Choi, J.U.; Jeong, M.; Kim, B.; Kim, M.J.; Kim, S.H. Upregulation of microRNA135a-3p and death receptor 5 plays a critical role in Tanshinone I sensitized prostate cancer cells to TRAIL induced apoptosis. Oncotarget, 2014, 5(14), 5624-5636.
[http://dx.doi.org/10.18632/oncotarget.2152] [PMID: 25015549]
[79]
Yu, H.; Subedi, R.K.; Nepal, P.R.; Kim, Y.G.; Choi, H-K. Enhancement of solubility and dissolution rate of cryptotanshinone, tanshinone I and tanshinone IIA extracted from Salvia miltiorrhiza. Arch. Pharm. Res., 2012, 35(8), 1457-1464.
[http://dx.doi.org/10.1007/s12272-012-0816-1] [PMID: 22941489]
[80]
Liu, Y.; Li, X.; Li, Y.; Wang, L.; Xue, M. Simultaneous determination of danshensu, rosmarinic acid, cryptotanshinone, tanshinone IIA, tanshinone I and dihydrotanshinone I by liquid chromatographic-mass spectrometry and the application to pharmacokinetics in rats. J. Pharm. Biomed. Anal., 2010, 53(3), 698-704.
[http://dx.doi.org/10.1016/j.jpba.2010.03.041] [PMID: 20430561]
[81]
Park, E.J.; Ji, H.Y.; Kim, N.J.; Song, W.Y.; Kim, Y.H.; Kim, Y.C.; Sohn, D.H.; Lee, H.S. Simultaneous determination of tanshinone I, dihydrotanshinone I, tanshinone IIA and cryptotanshinone in rat plasma by liquid chromatography-tandem mass spectrometry: application to a pharmacokinetic study of a standardized fraction of Salvia miltiorrhiza, PF2401-SF. Biomed. Chromatogr., 2008, 22(5), 548-555.
[http://dx.doi.org/10.1002/bmc.968] [PMID: 18205136]
[82]
Qin, Y.L. Preparation of tanshinone I derivatives for pharmaceutical use. Patent number: CN1837200A, 2006.
[83]
Xu, W.; Jiang, C.; Yang, F.; Shen, X.; Li, R.; Xue, D. Preparation of tanshinone derivatives as anti-tumor agents. Patent number: CN103288916A, 2012.
[84]
Jiao, M.; Ding, C.; Zhang, A. Preparation of 2-aryl derivatives of tanshinone I through a palladium-catalyzed Csp2-H activation/arylation approach. Tetrahedron Lett., 2015, 56, 2799-2802.
[http://dx.doi.org/10.1016/j.tetlet.2015.04.040]
[85]
Luan, D.; Qin, L.; Huang, W.; Luan, S. Tanshinone derivative, preparation method and application thereof. Patent number: CN105884723A, 2016.
[86]
Luan, D.; Qin, L.; Luan, S. Tanshinone derivative useful in treatment of various diseases and its preparation. Patent number: CN 105884857A, 2016.
[87]
Jiao, M.; Ding, C.; Zhang, A. Facile construction of 3-hydroxyphenanthrene-1,4-diones: key intermediates to tanshinone I and its A-ring-modified analogue. Tetrahedron, 2014, 70, 2976-2981.
[http://dx.doi.org/10.1016/j.tet.2014.03.019]
[88]
Jin, H.; Li, H.; Mao, S.; Ma, W.; Chen, Y.; Liu, S. Tanshinone I derivatives, synthetic method and antitumor application. Patent number: CN 102702302B, 2014.
[89]
Ding, C.; Tian, Q.; Li, J.; Jiao, M.; Song, S.; Wang, Y.; Miao, Z.; Zhang, A. Structural modification of natural product Tanshinone I leading to discovery of novel nitrogen-enriched derivatives with enhanced anticancer profile and improved drug-like properties. J. Med. Chem., 2018, 61(3), 760-776.
[http://dx.doi.org/10.1021/acs.jmedchem.7b01259] [PMID: 29294282]
[90]
Ding, C.; Song, S.; Jiao, M.; Wang, Y.; Miao, Z.; Zhang, A. Tanshinone I derivative, preparation method and applications thereof Tanshinone I derivative, preparation method and applications thereof. Patent number: CN105622709A, 2016.
[91]
Yoon, Y.; Kim, Y.O.; Jeon, W.K.; Park, H.J.; Sung, H.J. Tanshinone IIA isolated from Salvia miltiorrhiza BUNGE induced apoptosis in HL60 human premyelocytic leukemia cell line. J. Ethnopharmacol., 1999, 68(1-3), 121-127.
[http://dx.doi.org/10.1016/S0378-8741(99)00059-8] [PMID: 10624871]
[92]
Zhou, L.; Chan, W.K.; Xu, N.; Xiao, K.; Luo, H.; Luo, K.Q.; Chang, D.C. Tanshinone IIA, an isolated compound from Salvia miltiorrhiza Bunge, induces apoptosis in HeLa cells through mitotic arrest. Life Sci., 2008, 83(11-12), 394-403.
[http://dx.doi.org/10.1016/j.lfs.2008.07.011] [PMID: 18721815]
[93]
Wang, J.; Wang, X.; Jiang, S.; Yuan, S.; Lin, P.; Zhang, J.; Lu, Y.; Wang, Q.; Xiong, Z.; Wu, Y.; Ren, J.; Yang, H. Growth inhibition and induction of apoptosis and differentiation of tanshinone IIA in human glioma cells. J. Neurooncol., 2007, 82(1), 11-21.
[http://dx.doi.org/10.1007/s11060-006-9242-x] [PMID: 16955220]
[94]
Liu, J.J.; Lin, D.J.; Liu, P.Q.; Huang, M.; Li, X.D.; Huang, R.W. 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(6), 813-823.
[http://dx.doi.org/10.1007/s11373-006-9110-x] [PMID: 16955348]
[95]
Liu, J.J.; Zhang, Y.; Lin, D.J.; Xiao, R.Z. Tanshinone IIA inhibits leukemia THP-1 cell growth by induction of apoptosis. Oncol. Rep., 2009, 21(4), 1075-1081.
[http://dx.doi.org/10.3892/or_00000326] [PMID: 19288011]
[96]
Yuan, S.L.; Wei, Y.Q.; Wang, X.J.; Xiao, F.; Li, S.F.; Zhang, J. Growth inhibition and apoptosis induction of tanshinone II-A on human hepatocellular carcinoma cells. World J. Gastroenterol., 2004, 10(14), 2024-2028.
[http://dx.doi.org/10.3748/wjg.v10.i14.2024] [PMID: 15237427]
[97]
Sung, H.J.; Choi, S.M.; Yoon, Y.; An, K.S. Tanshinone IIA, an ingredient of Salvia miltiorrhiza BUNGE, induces apoptosis in human leukemia cell lines through the activation of caspase-3. Exp. Mol. Med., 1999, 31(4), 174-178.
[http://dx.doi.org/10.1038/emm.1999.28] [PMID: 10630370]
[98]
Pan, T.L.; Hung, Y.C.; Wang, P.W.; Chen, S.T.; Hsu, T.K.; Sintupisut, N.; Cheng, C.S.; Lyu, P.C. Functional proteomic and structural insights into molecular targets related to the growth inhibitory effect of tanshinone IIA on HeLa cells. Proteomics, 2010, 10(5), 914-929.
[http://dx.doi.org/10.1002/pmic.200900178] [PMID: 20049856]
[99]
Dong, X.; Dong, J.; Peng, G. Growth-inhibiting and apoptosis-inducing effects of tanshinone II A on human gastric carcinoma cells. J. Huazhong Univ. Sci. Technolog. Med. Sci., 2007, 27(6), 706-709.
[http://dx.doi.org/10.1007/s11596-007-0623-y ] [PMID: 18231749]
[100]
Zhang, Z.; Gao, J.; Wang, Y.; Song, T.; Zhang, J.; Wu, G.; Zhang, T.; Du, G. Tanshinone IIA triggers p53 responses and apoptosis by RNA polymerase II upon DNA minor groove binding. Biochem. Pharmacol., 2009, 78(10), 1316-1322.
[http://dx.doi.org/10.1016/j.bcp.2009.06.110] [PMID: 19591811]
[101]
Zhang, Z.; Zhang, J.; Jin, L.; Song, T.; Wu, G.; Gao, J. Tanshinone IIA interacts with DNA by minor groove-binding. Biol. Pharm. Bull., 2008, 31(12), 2342-2345.
[http://dx.doi.org/10.1248/bpb.31.2342] [PMID: 19043224]
[102]
Shan, Y.F.; Shen, X.; Xie, Y.K.; Chen, J.C.; Shi, H.Q.; Yu, Z.P.; Song, Q.T.; Zhou, M.T.; Zhang, Q.Y. Inhibitory effects of tanshinone II-A on invasion and metastasis of human colon carcinoma cells. Acta Pharmacol. Sin., 2009, 30(11), 1537-1542.
[http://dx.doi.org/10.1038/aps.2009.139] [PMID: 19820721]
[103]
Jang, S.I.; Kim, H.J.; Kim, Y.J.; Jeong, S.I.; You, Y.O. Tanshinone IIA inhibits LPS-induced NF-kappaB activation in RAW 264.7 cells: possible involvement of the NIK-IKK, ERK1/2, p38 and JNK pathways. Eur. J. Pharmacol., 2006, 542(1-3), 1-7.
[http://dx.doi.org/10.1016/j.ejphar.2006.04.044] [PMID: 16797002]
[104]
Liu, W.; Zhou, J.; Geng, G.; Shi, Q.; Sauriol, F.; Wu, J.H. Antiandrogenic, maspin induction, and antiprostate cancer activities of tanshinone IIA and its novel derivatives with modification in ring A. J. Med. Chem., 2012, 55(2), 971-975.
[http://dx.doi.org/10.1021/jm2015292] [PMID: 22175694]
[105]
Zhang, B.; Shi, L.; Liu, S.; Guo, R. Tanshinone IIA derivative, and preparation and application of tanshinone IIA derivative. Patent number: CN104961794A, 2015.
[106]
Zhang, B.; Shi, L.; Liu, S.; Guo, R. Tanshinone IIA ethylidene imine phosphate derivative, as well as preparation method and application thereof. Patent number: CN105037427A, 2015.
[107]
Zhang, H.; Liu, W.; Liu, Z.; Ju, Y.; Xu, M.; Zhang, Y.; Wu, X.; Gu, Q.; Wang, Z.; Xu, J. Discovery of indoleamine 2,3-dioxygenase inhibitors using machine learning based virtual screening. Med. Chem. Comm., 2018, 9(6), 937-945.
[http://dx.doi.org/10.1039/C7MD00642J] [PMID: 30108982]
[108]
Gu, Q.; Zhang, H.; Xu, J.; Zhou, H. Indoleamine 2, 3- dioxygenase inhibitor containing tanshinone compound. Patent number: CN107698652A, 2018.
[109]
Zhao, Q.; Liu, J.; Ren, J.; Wu, X.; Yang, K. Tanshinone IIA derivative with IDO/TDO doubly-selective inhibitory activity. Patent number: CN109824753A, 2019.
[110]
Zhou, C.; Gan, L.; Zeng, L.; Zhu, Z. Amino acid tanshinone phenolic ester derivatives and preparation method thereof. Patent number: CN103980341A, 2014.
[111]
Bao, G.; Yuan, L.; He, X.; Liu, Z.; Peng, S.; Dong, Y.; Wang, H. Tanshinone IIA novel derivative, preparation method and applications thereof. Patent number: CN106243071A, 2016.
[112]
VanPatten, S.; Al-Abed, Y. High mobility group box-1 (HMGb1): current wisdom and advancement as a potential drug target. J. Med. Chem., 2018, 61(12), 5093-5107.
[http://dx.doi.org/10.1021/acs.jmedchem.7b01136] [PMID: 29268019]
[113]
Guo, S.; Luo, W.; Liu, L.; Pang, X.; Zhu, H.; Liu, A.; Lu, J.; Ma, D-L.; Leung, C-H.; Wang, Y.; Chen, X. Isocryptotanshinone, a STAT3 inhibitor, induces apoptosis and pro-death autophagy in A549 lung cancer cells. J. Drug Target., 2016, 24(10), 934-942.
[http://dx.doi.org/10.3109/1061186X.2016.1157882] [PMID: 26904961]
[114]
Liu, X.; Chen, Z.; Yu, Z.; Zhou, Y.; Feng, T.; Zhou, Y.; Peng, L.; Tian, M.; Zhang, M. Tanshinone framework spliced bisindole or bispyrrole compound as well as preparation method and application thereof. Patent number: CN107188924A, 2017
[115]
Wu, Q.; Zheng, K.; Huang, X.; Li, L.; Mei, W. Tanshinone-IIA-based analogues of imidazole alkaloid act as potent inhibitors to block breast cancer invasion and metastasis in vivo. J. Med. Chem., 2018, 61(23), 10488-10501.
[http://dx.doi.org/10.1021/acs.jmedchem.8b01018] [PMID: 30398868]
[116]
Mei, W. Application of tanshinone IIA derivatives in preparation of anti-gastric cancer drugs. Patent number: CN110123811A, 2019
[117]
Wang, D.; Zhang, W.; Wang, T.; Li, N.; Mu, H.; Zhang, J.; Duan, J. Unveiling the mode of action of two antibacterial tanshinone derivatives. Int. J. Mol. Sci., 2015, 16(8), 17668-17681.
[http://dx.doi.org/10.3390/ijms160817668] [PMID: 26263982]
[118]
Zeng, L.W.; Zhou, C.X.; Liu, J.D.; Liu, C.H.; Mo, J.X.; Hou, A.F.; Yao, W.; Wang, Z.Z.; Gan, L.S. Design, synthesis, and antimicrobial activities of new tanshinone IIA esters. Nat. Prod. Res., 2016, 30(23), 2662-2668.
[http://dx.doi.org/10.1080/14786419.2016.1138302] [PMID: 26829106]
[119]
Zhang, D.; Guo, J.; Zhang, M.; Liu, X.; Ba, M.; Tao, X.; Yu, L.; Guo, Y.; Dai, J. Oxazole-containing diterpenoids from cell cultures of Salvia miltiorrhiza and their anti-HIV-1 activities. J. Nat. Prod., 2017, 80(12), 3241-3246.
[http://dx.doi.org/10.1021/acs.jnatprod.7b00659] [PMID: 29185738]
[120]
Liu, W.; Yu, B.; Xu, G.; Xu, W-R.; Loh, M.L.; Tang, L-D.; Qu, C-K. Identification of cryptotanshinone as an inhibitor of oncogenic protein tyrosine phosphatase SHP2 (PTPN11). J. Med. Chem., 2013, 56(18), 7212-7221.
[http://dx.doi.org/10.1021/jm400474r] [PMID: 23957426]
[121]
Wang, J.; Huang, Z.; He, L.; He, L.; You, Q.; Li, Q. New application of tanshinone IIA derivatives as MAGL (monoacylglycerol lipase) inhibitor. Patent number: CN107118254A, 2017.
[122]
Wang, X.; Guo, J.; Ning, Z.; Wu, X. Discovery of a natural Syk inhibitor from chinese medicine through a docking-based virtual screening and biological assay study. Molecules, 2018, 23(12), 23.
[http://dx.doi.org/10.3390/molecules23123114] [PMID: 30487406]
[123]
Manzoni, L.; Zucal, C.; Maio, D.D.; D’Agostino, V.G.; Thongon, N.; Bonomo, I.; Lal, P.; Miceli, M.; Baj, V.; Brambilla, M.; Cerofolini, L.; Elezgarai, S.; Biasini, E.; Luchinat, C.; Novellino, E.; Fragai, M.; Marinelli, L.; Provenzani, A.; Seneci, P. Interfering with HuR-RNA interaction: design, synthesis and biological characterization of tanshinone mimics as novel, effective HuR Inhibitors. J. Med. Chem., 2018, 61(4), 1483-1498.
[http://dx.doi.org/10.1021/acs.jmedchem.7b01176] [PMID: 29313684]
[124]
Provenzani, A.; D'Agostino, V.G.; Thongon, N.; Zucal, C.; Lal, P.; Adami, V.; Seneci, P.; Manzoni, L.; Marubelli, L.; Novellino, E.; Fragai, M.; Luchinat, C.; Cerofolinl, L.; Fuccio, C. Aza-tanshinone derivatives, process for their preparation and their use in therapy. Patent number: WO2017216732A1, 2017
[125]
Potter, P.M.; Wadkins, R.M. Carboxylesterases-detoxifying enzymes and targets for drug therapy. Curr. Med. Chem., 2006, 13(9), 1045-1054.
[http://dx.doi.org/10.2174/092986706776360969] [PMID: 16611083]
[126]
Hatfield, M.J.; Tsurkan, L.G.; Hyatt, J.L.; Edwards, C.C.; Lemoff, A.; Jeffries, C.; Yan, B.; Potter, P.M. Modulation of esterified drug metabolism by tanshinones from Salvia miltiorrhiza (“Danshen”). J. Nat. Prod., 2013, 76(1), 36-44.
[http://dx.doi.org/10.1021/np300628a] [PMID: 23286284]
[127]
Hatfield, M.J.; Binder, R.J.; Gannon, R.; Fratt, E.M.; Bowling, J.; Potter, P.M. Potent, irreversible inhibition of human carboxylesterases by tanshinone anhydrides isolated from Salvia miltiorrhiza (“Danshen”). J. Nat. Prod., 2018, 81(11), 2410-2418.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00378] [PMID: 30351923]
[128]
Binder, R.J.; Hatfield, M.J.; Chi, L.; Potter, P.M. Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors. Eur. J. Med. Chem., 2018, 149, 79-89.
[http://dx.doi.org/10.1016/j.ejmech.2018.02.052] [PMID: 29499489]
[129]
Ding, C.; Chen, H.; Liang, B.; Jiao, M.; Liang, G.; Zhang, A. Biomimetic synthesis of the natural product salviadione and its hybrids: discovery of tissue-specific anti-inflammatory agents for acute lung injury. Chem. Sci. (Camb.), 2019, 10(17), 4667-4672.
[http://dx.doi.org/10.1039/C9SC00086K] [PMID: 31123577]
[130]
Yang, Z.; Mei, W.; Ma, L.; Zhao, Z.; Luo, S.; Zhou, L. Tanshinone IIA derivative TAN20, preparation method and application thereof. CN110330545A, 2019.
[131]
Ma, X.H.; Ma, Y.; Tang, J.F.; He, Y.L.; Liu, Y.C.; Ma, X.J.; Shen, Y.; Cui, G.H.; Lin, H.X.; Rong, Q.X.; Guo, J.; Huang, L.Q. The Biosynthetic Pathways of Tanshinones and Phenolic Acids in Salvia miltiorrhiza. Molecules, 2015, 20(9), 16235-16254.
[http://dx.doi.org/10.3390/molecules200916235] [PMID: 26370949]
[132]
Gao, W.; Sun, H.X.; Xiao, H.; Cui, G.; Hillwig, M.L.; Jackson, A.; Wang, X.; Shen, Y.; Zhao, N.; Zhang, L.; Wang, X.J.; Peters, R.J.; Huang, L. Combining metabolomics and transcriptomics to characterize tanshinone biosynthesis in Salvia miltiorrhiza. BMC Genomics, 2014, 15, 73.
[http://dx.doi.org/10.1186/1471-2164-15-73] [PMID: 24467826]
[133]
Xu, J.; Zhang, C.; Shi, X.; Li, J.; Liu, M.; Jiang, W.; Fang, Z. Efficacy and safety of sodium tanshinone IIA sulfonate injection on hypertensive nephropathy: a systematic review and meta-analysis. Front. Pharmacol., 2019, 10, 1542-1555.
[http://dx.doi.org/10.3389/fphar.2019.01542] [PMID: 31920681]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy