Abstract
The available scientific literature regarding tanshinones is very abundant, and after its review, it is noticeable that most of the articles focus on the properties of tanshinone I, cryptotanshinone, tanshinone IIA, sodium tanshinone IIA sulfonate and the dried root extract of Salvia miltiorrhiza (Tan- Shen). However, although these products have demonstrated important biological properties in both in vitro and in vivo models, their poor solubility and bioavailability have limited their clinical applications. For these reasons, many studies have focused on the search for new pharmaceutical formulations for tanshinones, as well as the synthesis of new derivatives that improve their biological properties. To provide new insights into the critical path ahead, we systemically reviewed the most recent advances (reported since 2015) on tanshinones in scientific databases (PubMed, Web of Science, Medline, Scopus, and Clinical Trials). With a broader perspective, we offer an update on the last five years of new research on these quinones, focusing on their synthesis, biological activity on noncommunicable diseases and drug delivery systems, to support future research on its clinical applications.
Keywords: Tanshinone IIA, Tanshinones, synthesis, biological activities, drug delivery systems, nanoparticles, bioavailability, solubility.
Graphical Abstract
[http://dx.doi.org/10.1021/cr200058f] [PMID: 22967178]
[http://dx.doi.org/10.1016/S0040-4039(00)89532-5]
[http://dx.doi.org/10.1039/c0np00035c] [PMID: 21225077]
[http://dx.doi.org/10.1016/S0140-6736(15)00516-4 ] [PMID: 26520231]
[PMID: 26792989]
[http://dx.doi.org/10.1055/s-0035-1546196] [PMID: 26190397]
[http://dx.doi.org/10.1248/cpb.53.1524] [PMID: 16327182]
[http://dx.doi.org/10.1016/j.tet.2014.03.019]
[http://dx.doi.org/10.1039/C8OB00567B] [PMID: 29670981]
[http://dx.doi.org/10.1080/10286020.2015.1136906 ] [PMID: 26828227]
[http://dx.doi.org/10.1021/acs.jnatprod.7b00238] [PMID: 28443671]
[http://dx.doi.org/10.1016/j.bmcl.2012.05.014] [PMID: 22765898]
[http://dx.doi.org/10.1021/acs.jnatprod.6b00370] [PMID: 27672695]
[http://dx.doi.org/10.1016/j.tetlet.2017.03.078]
[http://dx.doi.org/10.1021/acs.jmedchem.8b01018] [PMID: 30398868]
[http://dx.doi.org/10.1016/j.tetlet.2017.11.046]
[http://dx.doi.org/10.1080/00397911.2017.1378359]
[http://dx.doi.org/10.1021/acs.joc.7b01064] [PMID: 28653529]
[http://dx.doi.org/10.1021/ol400164e] [PMID: 23452325]
[PMID: 24716403]
[http://dx.doi.org/10.1016/j.chroma.2013.02.055] [PMID: 23522260]
[http://dx.doi.org/10.1016/j.bmcl.2010.06.076] [PMID: 20637608]
[http://dx.doi.org/10.1016/j.resmic.2016.08.002] [PMID: 27545500]
[http://dx.doi.org/10.1016/j.tetlet.2015.04.040]
[http://dx.doi.org/10.1039/C3RA45146A]
[http://dx.doi.org/10.1007/s00253-016-7488-6] [PMID: 27198724]
[http://dx.doi.org/10.3322/caac.21551] [PMID: 30620402]
[http://dx.doi.org/10.1038/nrc3599] [PMID: 24060863]
[http://dx.doi.org/10.12659/MSM.914446] [PMID: 31250836]
[http://dx.doi.org/10.1002/ptr.6392] [PMID: 31268205]
[http://dx.doi.org/10.1155/2019/2374565] [PMID: 31281233]
[http://dx.doi.org/10.1186/s12918-018-0606-6] [PMID: 30373594]
[http://dx.doi.org/10.1016/j.biopha.2018.06.028] [PMID: 29909343]
[http://dx.doi.org/10.1038/s41419-017-0247-5] [PMID: 29416003]
[http://dx.doi.org/10.1186/s12885-016-2921-x] [PMID: 27863471]
[http://dx.doi.org/10.2147/OTT.S161534] [PMID: 29636623]
[http://dx.doi.org/10.1055/s-0033-1360126] [PMID: 24414309]
[http://dx.doi.org/10.1002/ptr.6353] [PMID: 30945389]
[http://dx.doi.org/10.3892/etm.2016.2984] [PMID: 26998041]
[http://dx.doi.org/10.1016/j.apjtm.2016.09.003] [PMID: 27890369]
[http://dx.doi.org/10.1007/s00262-019-02326-8] [PMID: 30972427]
[http://dx.doi.org/10.1016/j.intimp.2003.12.003] [PMID: 14996412]
[http://dx.doi.org/10.1142/S0192415X05002990] [PMID: 16047556]
[http://dx.doi.org/10.1007/s00280-016-3034-6] [PMID: 27100736]
[http://dx.doi.org/10.1016/j.intimp.2018.10.035] [PMID: 30388517]
[http://dx.doi.org/10.1016/j.ccell.2014.10.006] [PMID: 25517747]
[http://dx.doi.org/10.3389/fonc.2018.00248] [PMID: 30013950]
[http://dx.doi.org/10.18632/oncotarget.3648] [PMID: 26202747]
[http://dx.doi.org/10.1371/journal.pone.0117440] [PMID: 25659153]
[http://dx.doi.org/10.1016/j.canlet.2017.05.013] [PMID: 28602978]
[http://dx.doi.org/10.3892/or.2014.3592] [PMID: 25376085]
[http://dx.doi.org/10.1371/journal.pone.0100416] [PMID: 24992590]
[PMID: 30787992]
[http://dx.doi.org/10.1016/j.bbrc.2019.09.106] [PMID: 31623833]
[http://dx.doi.org/10.1016/S1474-4422(15)70016-5 ] [PMID: 25792098]
[http://dx.doi.org/10.1111/jphp.12650] [PMID: 27882565]
[http://dx.doi.org/10.1097/WNR.0000000000000419 ] [PMID: 26164608]
[http://dx.doi.org/10.1016/j.neulet.2016.11.024] [PMID: 27845241]
[http://dx.doi.org/10.1016/j.bbr.2019.03.001] [PMID: 30831140]
[http://dx.doi.org/10.1016/j.neulet.2017.08.059] [PMID: 28859867]
[http://dx.doi.org/10.1371/journal.pone.0202532] [PMID: 30138344]
[http://dx.doi.org/10.1016/j.phytol.2018.05.016]
[http://dx.doi.org/10.1016/j.jep.2015.01.042] [PMID: 25666429]
[http://dx.doi.org/10.1186/s13195-018-0457-9] [PMID: 30591071]
[http://dx.doi.org/10.1055/s-2004-815535] [PMID: 15114495]
[http://dx.doi.org/10.1021/cn400051e] [PMID: 23506133]
[http://dx.doi.org/10.1016/j.etap.2011.02.006] [PMID: 21787715]
[http://dx.doi.org/10.1016/j.ejphar.2007.07.042] [PMID: 17714702]
[http://dx.doi.org/10.1016/j.cbi.2010.03.026] [PMID: 20350537]
[http://dx.doi.org/10.1021/np800318m] [PMID: 19007183]
[http://dx.doi.org/10.3109/14756366.2015.1057724 ] [PMID: 26114310]
[http://dx.doi.org/10.1016/j.ejmech.2016.06.036] [PMID: 27376495]
[http://dx.doi.org/10.1016/j.amjmed.2014.10.047] [PMID: 25460529]
[http://dx.doi.org/10.1038/s41598-017-16980-4] [PMID: 29234038]
[http://dx.doi.org/10.18632/oncotarget.14328] [PMID: 28053285]
[http://dx.doi.org/10.1093/ecam/nep056] [PMID: 19542183]
[http://dx.doi.org/10.1080/10286020.2017.1337751 ] [PMID: 28595458]
[http://dx.doi.org/10.1021/acsami.8b20158] [PMID: 30592403]
[http://dx.doi.org/10.1016/j.yjmcc.2019.09.012] [PMID: 31629735]
[PMID: 25589975]
[http://dx.doi.org/10.2147/IJN.S165590] [PMID: 30022826]
[http://dx.doi.org/10.1016/j.ejphar.2016.09.041] [PMID: 27693799]
[http://dx.doi.org/10.1039/C8NJ04819C]
[http://dx.doi.org/10.1073/pnas.1621375114] [PMID: 28424250]
[http://dx.doi.org/10.1016/j.jep.2016.12.042] [PMID: 28038955]
[http://dx.doi.org/10.1371/journal.pone.0129655] [PMID: 26061047]
[http://dx.doi.org/10.1016/j.intimp.2015.02.027] [PMID: 25744602]
[http://dx.doi.org/10.1155/2015/867140] [PMID: 26885500]
[http://dx.doi.org/10.4314/tjpr.v16i12.9]
[http://dx.doi.org/10.1016/j.biopha.2019.109586] [PMID: 31706104]
[http://dx.doi.org/10.3892/mmr.2015.3333] [PMID: 25672255]
[http://dx.doi.org/10.1155/2018/6712585] [PMID: 30140368]
[http://dx.doi.org/10.1038/s41467-018-06514-5] [PMID: 30258187]
[http://dx.doi.org/10.1016/j.resp.2014.09.025] [PMID: 25305099]
[http://dx.doi.org/10.1016/j.ejphar.2017.09.047] [PMID: 28970012]
[http://dx.doi.org/10.1371/journal.pone.0178226] [PMID: 28542554]
[http://dx.doi.org/10.3389/fphar.2018.00062] [PMID: 29456510]
[http://dx.doi.org/10.1016/j.ejphar.2019.04.049] [PMID: 31051158]
[PMID: 27936472]
[http://dx.doi.org/10.1016/j.jep.2013.03.045] [PMID: 23542145]
[http://dx.doi.org/10.1111/exd.13511] [PMID: 29427477]
[PMID: 30344684]
[http://dx.doi.org/10.1080/14786419.2016.1138302 ] [PMID: 26829106]
[http://dx.doi.org/10.1124/mol.107.034447] [PMID: 17429005]
[http://dx.doi.org/10.1016/j.phymed.2015.12.004] [PMID: 26902408]
[http://dx.doi.org/10.1080/14786419.2019.1607337] [PMID: 31104489]
[http://dx.doi.org/10.1124/jpet.105.100701] [PMID: 16497784]
[http://dx.doi.org/10.1142/S0192415X13500146] [PMID: 23336516]
[http://dx.doi.org/10.1039/C5BM00224A] [PMID: 26484363]
[http://dx.doi.org/10.1088/0957-4484/27/49/495101 ] [PMID: 27834307]
[http://dx.doi.org/10.1007/s11434-016-1046-6]
[http://dx.doi.org/10.1016/j.jddst.2018.10.024]
[http://dx.doi.org/10.1039/C6CC08502D] [PMID: 27966687]
[http://dx.doi.org/10.1016/j.biochi.2016.07.008] [PMID: 27436182]
[http://dx.doi.org/10.1016/j.bmcl.2016.03.097] [PMID: 27040657]
[PMID: 21348419]
[http://dx.doi.org/10.1208/s12249-010-9410-3] [PMID: 20352534]
[http://dx.doi.org/10.1080/21691401.2018.1508028] [PMID: 30284484]
[http://dx.doi.org/10.1016/j.ejps.2015.03.002] [PMID: 25769523]