Abstract
Coumarins are the secondary metabolites of some plants, fungi, and bacteria. Coumarins and the hybrid molecules of coumarins are the compounds which have been widely studied for their potential anticancer effects. They belong to benzopyrone chemical class, more precisely benzo-α-pyrones, where benzene ring is fused to pyrone ring. In nature, coumarins are found in higher plants like Rutaceae and Umbelliferae and some essential oils like cinnamon bark oil, cassia leaf oil and lavender oil are also rich in coumarins. The six main classes of coumarins are furanocoumarins, dihydrofuranocoumarins, pyrano coumarins, pyrone substituted coumarins, phenylcoumarins and bicoumarins. As well as their wide range of biological activities, coumarins and the hybrid molecules of coumarins are proven to have an important role in anticancer drug development due to the fact that many of its derivatives have shown an anticancer activity on various cell lines. Osthol, imperatorin, esculetin, scopoletin, umbelliprenin, angelicine, bergamottin, limettin, metoxhalen, aurapten and isopimpinellin are some of these coumarins. This review summarizes the anticancer effects of coumarins and their hybrid molecules including the novel pharmaceutical formulations adding further information on the topic for the last ten years and basically focusing on the structureactivity relationship of these compounds in cancer.
Keywords: Coumarines, coumarine derivatives, coumarine nanoformulations, coumarine hybride molecules, anticancer effect, metabolites.
[http://dx.doi.org/10.3389/fphar.2018.00245 ] [PMID: 29623040]
[http://dx.doi.org/10.1371/journal.pone.0187925] [PMID: 29121120]
[http://dx.doi.org/10.3390/ijms19010263 ] [PMID: 29337925]
[http://dx.doi.org/10.1016/S2221-1691(13)60060-X ] [PMID: 23620848]
[http://dx.doi.org/10.2174/1874104501711010196 ] [PMID: 29387274]
[http://dx.doi.org/10.1002/ardp.201600369] [PMID: 28543820]
[http://dx.doi.org/10.1016/j.bmcl.2017.07.069 ] [PMID: 28797799]
[http://dx.doi.org/10.1016/j.ejmech.2015.07.010 ] [PMID: 26188907]
[http://dx.doi.org/10.3390/molecules191220839 ] [PMID: 25514225]
[http://dx.doi.org/10.3390/ijms20061300 ] [PMID: 30875859]
[http://dx.doi.org/10.4103/2231-4040.101006 ] [PMID: 23057000]
[PMID: 24363556]
[http://dx.doi.org/10.1186/s12951-018-0392-8 ] [PMID: 30231877]
[http://dx.doi.org/10.1080/14756366.2018.1477137 ] [PMID: 29944015]
[PMID: 18210747]
[http://dx.doi.org/10.1016/j.ejphar.2014.10.048 ] [PMID: 25445053]
[http://dx.doi.org/10.1016/j.bmcl.2006.06.007 ] [PMID: 16793260]
[http://dx.doi.org/10.1186/s12950-015-0087-y ] [PMID: 26221081]
[http://dx.doi.org/10.2174/092986708786242877 ] [PMID: 18991629]
[http://dx.doi.org/10.1016/j.bmcl.2019.05.008 ] [PMID: 31104996]
[http://dx.doi.org/10.1021/acsomega.8b02481 ] [PMID: 31459961]
[http://dx.doi.org/10.2174/1871520619666190207140120 ] [PMID: 30734685]
[http://dx.doi.org/10.2174/1871520618666181119110934 ] [PMID: 30451120]
[http://dx.doi.org/10.1016/j.bmc.2015.12.032 ] [PMID: 26740157]
[http://dx.doi.org/10.2174/1381612043382693 ] [PMID: 15579072]
[http://dx.doi.org/10.3109/14756366.2015.1063624 ] [PMID: 26207513]
[http://dx.doi.org/10.1016/j.bmc.2010.03.026 ] [PMID: 20363143]
[http://dx.doi.org/10.3109/14756366.2012.677838 ] [PMID: 22512727]
[http://dx.doi.org/10.17344/acsi.2018.4519]
[http://dx.doi.org/10.1155/BCA/2006/68274 ] [PMID: 17497014]
[http://dx.doi.org/10.1016/j.bmcl.2005.07.041 ] [PMID: 16137881]
[http://dx.doi.org/10.2174/1871520616666160902094739 ] [PMID: 27592545]
[http://dx.doi.org/10.2174/1871520616666160926112508 ] [PMID: 27671300]
[http://dx.doi.org/10.1016/j.biopha.2016.12.117 ] [PMID: 28081470]
[http://dx.doi.org/10.1021/acsami.7b15434 ] [PMID: 29171261]
[http://dx.doi.org/10.1016/j.dyepig.2017.07.001]
[http://dx.doi.org/10.1021/acs.organomet.7b00750]
[http://dx.doi.org/10.1021/acs.orglett.5b02728 ] [PMID: 26451846]
[http://dx.doi.org/10.1016/j.msec.2017.05.126 ] [PMID: 28866169]
[http://dx.doi.org/10.2174/1567201813666161017130612 ] [PMID: 27745545]
[http://dx.doi.org/10.1016/j.msec.2016.05.093 ] [PMID: 27524002]
[http://dx.doi.org/10.1039/C4BM00134F]
[http://dx.doi.org/10.3109/02652048.2012.746749 ] [PMID: 23517067]
[http://dx.doi.org/10.1021/bm101206g ] [PMID: 21158381]
[http://dx.doi.org/10.1016/j.ijpharm.2013.07.017 ] [PMID: 23856033]
[http://dx.doi.org/10.1016/j.colsurfb.2015.06.043 ] [PMID: 26164204]
[PMID: 23696703]
[http://dx.doi.org/10.2147/DDDT.S127328 ] [PMID: 28293102]
[http://dx.doi.org/10.1016/j.actbio.2018.03.057 ] [PMID: 29649635]
[http://dx.doi.org/10.1016/j.colsurfb.2016.06.054 ] [PMID: 27419647]
[http://dx.doi.org/10.1038/s41467-019-09928-x ] [PMID: 31019192]
[http://dx.doi.org/10.1039/C5RA12676B]
[http://dx.doi.org/10.1021/acsami.7b17711 ] [PMID: 29302967]
[http://dx.doi.org/10.1021/ja401350x ] [PMID: 23461361]
[http://dx.doi.org/10.3109/08923973.2013.863912 ] [PMID: 24325354]
[http://dx.doi.org/10.1021/am401059k ] [PMID: 23730930]
[http://dx.doi.org/10.1039/C5TB00694E]
[http://dx.doi.org/10.1039/C6CC05707A ] [PMID: 27477036]
[http://dx.doi.org/10.1016/j.biomaterials.2015.02.108 ] [PMID: 25890760]
[http://dx.doi.org/10.1016/j.actbio.2015.04.021 ] [PMID: 25910639]
[http://dx.doi.org/10.1016/j.nano.2017.03.006 ] [PMID: 28343019]
[http://dx.doi.org/10.7314/APJCP.2015.16.13.5325 ] [PMID: 26225673]
[http://dx.doi.org/10.1016/j.taap.2011.04.010 ] [PMID: 21549736]
[http://dx.doi.org/10.1039/C5PP00057B ] [PMID: 26066468]
[http://dx.doi.org/10.3892/ijmm.2017.2974 ] [PMID: 28487974]
[http://dx.doi.org/10.1039/C7NR03964F ] [PMID: 28805867]
[http://dx.doi.org/10.1021/acsanm.8b01533]
[http://dx.doi.org/10.1016/j.msec.2010.05.005]
[http://dx.doi.org/10.1002/tox.22530 ] [PMID: 29319219]
[http://dx.doi.org/10.3892/mmr.2012.1044 ] [PMID: 22923177]
[http://dx.doi.org/10.1097/CAD.0000000000000812 ] [PMID: 31283543]
[http://dx.doi.org/10.1016/j.jep.2017.03.033 ] [PMID: 28341244]
[PMID: 11497276]
[http://dx.doi.org/10.3390/ijms20153802 ] [PMID: 31382639]
[http://dx.doi.org/10.1186/s12943-016-0550-2 ] [PMID: 27756327]
[http://dx.doi.org/10.1016/j.mvr.2016.04.009 ] [PMID: 27133199]
[http://dx.doi.org/10.1007/s11010-012-1372-1 ] [PMID: 22766766]
[http://dx.doi.org/10.3892/or.2016.4833 ] [PMID: 27222242]
[http://dx.doi.org/10.2147/IJN.S96614 ] [PMID: 26893562]
[http://dx.doi.org/10.2147/IJN.S191940 ] [PMID: 31015760]
[http://dx.doi.org/10.1089/jmf.2013.0029 ] [PMID: 24070132]
[http://dx.doi.org/10.3736/jcim20070111 ] [PMID: 17214937]
[PMID: 29251335]
[http://dx.doi.org/10.4103/pm.pm_432_16 ] [PMID: 28808378]
[http://dx.doi.org/10.1016/j.lfs.2019.01.029 ] [PMID: 30682342]
[http://dx.doi.org/10.1186/s12906-016-1368-6 ] [PMID: 27729078]
[http://dx.doi.org/10.4103/pm.pm_13_17 ] [PMID: 29142404]
[http://dx.doi.org/10.4062/biomolther.2015.145 ] [PMID: 27098859]
[http://dx.doi.org/10.1111/jphp.13013 ] [PMID: 30229910]
[http://dx.doi.org/10.1016/j.bmcl.2013.04.081 ] [PMID: 23746477]
[http://dx.doi.org/10.3390/molecules19044046 ] [PMID: 24699147]
[http://dx.doi.org/10.1007/s40495-015-0033-y ] [PMID: 26623248]
[http://dx.doi.org/10.3390/molecules22122170 ] [PMID: 29215592]
[http://dx.doi.org/10.1158/1940-6207.CAPR-15-0051 ] [PMID: 26116406]
[PMID: 21875271]
[http://dx.doi.org/10.3390/molecules201219738 ] [PMID: 26610461]
[http://dx.doi.org/10.3390/ijms19010010 ] [PMID: 29267213]
[http://dx.doi.org/10.3390/molecules15118060 ] [PMID: 21063269]
[http://dx.doi.org/10.1016/j.biopha.2019.108987] [PMID: 31112870]
[http://dx.doi.org/10.18632/oncotarget.24686 ] [PMID: 29682182]
[http://dx.doi.org/10.1080/10286020.2017.1292256 ] [PMID: 28276763]
[http://dx.doi.org/10.1111/j.2042-7158.2011.01378.x ] [PMID: 22150676]
[http://dx.doi.org/10.3390/molecules18044158 ] [PMID: 23567363]
[http://dx.doi.org/10.1016/j.biopha.2018.12.005 ] [PMID: 30544062]
[http://dx.doi.org/10.1016/j.biopha.2017.09.050 ] [PMID: 28946189]
[http://dx.doi.org/10.1111/cbdd.13120 ] [PMID: 29052945]