Abstract
Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.
Highlights
IntroductionCoumarins are a wide family of secondary metabolites found in various species of plants (more than 1300 coumarins have been identified from natural sources, especially green plants) and fungi and microorganisms [1,2]
This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches
Coumarins are a wide family of secondary metabolites found in various species of plants and fungi and microorganisms [1,2]
Summary
Coumarins are a wide family of secondary metabolites found in various species of plants (more than 1300 coumarins have been identified from natural sources, especially green plants) and fungi and microorganisms [1,2]. The main pathway of coumarin biosynthesis occurs by shikimic acid route, via cinnamic acid, through phenylalanine metabolism [3]. The history of these natural products began 200 years ago—the name of the class derived from the plant Coumarouna odorata (Dipteryx odorata) from which the simplest member of this family, coumarin itself (Figure 1), was isolated by Vogel in 1820 [3,4]. Rgreocuenpts.stRuedcieens thastvuedsihesowhanvaefushnocwtionnaal fruonlectoiof nliaplorxoylgeeonfasleipso(xLyOgXens)aisnesca(rLcOinXosg)einnesciasr, cpirneocgiseenleysiins, pprroesctiasteilcyciannpcerrosatnadticthceacnacpearbainlidtythoef 5c-afpaarbnielsityylooxfy5c-ofuamrnaersiynlo(1x8y,cFoiugumraer8in) t(o18in, hFiibgiut r1e5-8L)OtoXi-n1h[i4b2i–t4145]- Starting from these observations, Orafaie and collaborators investigated the inhibitory activity oasfoscafoycmoomSpntoFaptuirwogtnuiuondnrgecd1a8f81rr.c8oCoimnohneonmt1mh15i5eac--sLaLcelOeOsoltXlrXbu-ls-1ic1entru[e[v44rse5a5(]t]oP.i.foCT5nTh--shf3e,aeraOcnnycreydtasotyfoDtalootiUoexxyxi1acci4ncoe5dufe)fmffecacoaentrclsdiltnasoba(fo1on18fr8o)a1ratw8omnredwasr8leei-ncrfeaeevvrleanleslevlutisianyagleltuaoet(axdeHtydebcFdoytFuhb3mme)y,eainuarminhsneisinb(a1ogin9tfos)4M.r-oyMTf aTMMcatPTisvBsTiatyy 11w(pPμ23CccDPcf94Mmooma2es4oo8a942ihhxC4n88CgfnoUa-mcf94Mmoma2escau.lree.oh,.arm/dc5onlf03si3hho1xhn4n88nmtc1oasromstocii24ree1hco4lh,.hr,w,dbdeli4cbeeemDoa1rhlmeSt8canoLyrteacio5ia±2.9ixt4±oh±4nmrhwt,beolrtUmD2hgollab5nv88hDaanpAraeyflc-doa2i44±4myt3as.oo.2porreitd1Uienioclsca45ni1vUs8,n.aebt.t-l-rrrnsl4thDo4ra92d.u7t.4mio-2pei.(ld1n,a4usgicie4in135s28r2uc4r,Ptmr-nrnc4lctUoat8sd.±7cdm4o,±eo.-(gi)-s7,u4tonoCo3h5udrnui(4.Pmoh5d4myimcc128na1±r4cdd[m,nlul-7fe3nf48eoCoMh4s4.a1it.nmo-ro4eyds2h9acpn1me8hdmmn6r5w8oup1amc3fdht8m,P[e,td.e,.ooo],ehd8emc94s3moitha,olh.wp71neaCa2cherntmuhtlltay76,a,etun6,hnlt28eeisocuuA5csooa,u3n2]s7nlaoh42tncltlohaayn.a.pcdumnd6hiP1lh2isosgd4ns8.oybcrtdcvnesahlo52iAyn5aoei7n,Caepca,PindlpeelPnaheoen,1.hncr-pstdlsse1i1r±5gilwdCaineo±rLsiin,Cen8ame,Papuelrd,l8t8ios,la,rslss1e11pir±,O-3iamCcaiel.6uocPaneoai1uehwdodnr98tnt87ttelernsro2z1dnieXcnh.-b3cChir7cale..eoeasler9ahwdna,o93.imti7deceleesddsu-spa5anzsndea,Pnscs±a7,afe.el1teluoeatzs3isdelge7chylptdCrds7p(naD±rinwscesu-so2±if,l[onlrPo2olve2con:dtoeoe4aln3ytii).7(tNnDuwdesnetCu8naeo2f1buln2p5hPuyeslhi2c:psoldocrmd;et).o7dtN4e]iAo-psdnol,eoCnai8e,ibe2tuy.n3)Dh.gnopsurnpi1ned;ueat3dlo4m4wehATo-rvnitte,lnop,dny8nn3rcUDt,1dguamris,nhedi4om1imhiiyeo.searat8:.dttnt7nntdbf9n41U81eh8sar,iDra,atmnrr-i2w2demi70ooei4ieaa5ot8gec.fneiaOtrdf4cds18dhh4naNm.aan5mnre-iiatahdy1±0m±i45e1tcfsnDoeraoarttndaddghrsa.t,Aarc5een98tia5atdf1±7ep±toad2ioeisUDo,r[enndf-df-4gewmvat.4icentaofnt5.oa4lro8±7d7nnhts1sa8eie1Uaola[et,fnen-uewi0pimdi;sy5.e.4e.ana;rheoa4retlxt98t7[8ss.at:1nl-I-tiinh,ldfsnirD1m45diiii,i;sy5.vvecodC5botnav4s2abtnd-ec9te,)ti:a-I-4hlpeais±ix]r5dU54enewdmniia,5isedCbog±ve2nn-ti8tn0tay-p)rybidgssss4iphfx]id1thn4eeb7fci5ioeneoidcvyhfielhe8ethn0f7ayan4preb.i,]tioes-lonhcdeotnhunle9offiaoi.niti,drd5cyceho3aexoh8fvbrufnfμ,dw,znclo5cd2tetenunldec5enyxsa;laic,ee4mhesoo3age-lru7ferhpnμt.dyzcnecediDnaI28se25ehaxtnanla/offf.tomneCodotleacgeh0lb7mraz2n.hntyletUtDthf,ise2uonwortnai5cs/.rioh5onntaaichw0vimr1a±,a2uLn:oDt0mrddn1tUtrntecodorneei5±c8iehz2mnhnae4m2vheiaie1a±iUnuLodrduf1ai7tanetsnt5ai4c±wc3nDnez.onimh(anit4rmo.aey9rca1b1rec1.-f0iarctiielrc5ah9ccezr3,Ueeμrcl.pon4itntnn(a95e9rea)oetsirehic4,1ds.ioar4c,5reglr,rhtovcnr9sn,1erlxten(a-9±ees7r8on3eei)lteit/ir4,1iiaMc44cyenasseF,lhtvm2n5tcbscleylcasae-9leso7hr58)y3ictlvtireie.MveaitrcflasseMF,il2gih2fot.,Letaloalaleeolenonhmc9taoytioFsial2uua,c2trtscfsrnMsiegni,hf,lt,P;nlohbrireofetnsa7tou2tremrilgt±e7uisyo,I2rtrsaiBfnwreoeelnha.t6vPnnCahbgeuee2s8m7e2rrisatote:t.s(ei1tavBosacfroaieei4h4nh.r56intHr8ehtPfnte48ete.eosaec0yretot:3io.(hec9d)oscr±e4,-4nnhcCmlbtioHnF8Pfevu8,Mleetinaarohdc23±cbof)vshsFb3b2±a)Cmnl4tbaiccayrFhn6caeultohni.tcy3ecMy±v2yl8ttbolcoot.h2cFn3bt2ihucihayrtt4eh)1co.byeiccytemvf2s.hm31siyv2h,yvele3oPth5e2cli4tesHil,u)i;o.ebbcaiocsts,clHaeu-omm2l-1tBp,ciev±so7iLolDar4ltesHMioyxlo2nl,nons;eiesa:oot:lav2uorml-npmO7itsiaso7h.lof2UDlonh2sMxooulcPnhsiMsliss:.1oCh2r.vfin41Xfc8sGseiispinen.1g(C1Ucbo2s5bucan,eMy49acsI4oPiCh-;yoo4tdh4-0fiGCgiin3eon1ng(1tm1-lh/ntL4aDtnB5,fcou±oI,oM.PGioe9m4yotdho50o-eCgclniO1cynM3th0ne/Wn4nUM.erB5ncmrar,e.o1fGe52e9yMmp2c5s-eieydctmXcnPr30Wxln21i.pnM.ThcPt.mahMeole1e2l5nn.0(2hde-Cic4liePstachTanraChlIuec±22s1pni1μ.hahM:5leleenCcWPGnnB03la:ndcr,lsn13hauahrlget4±s±ii1μsagB2icc275lc8igdc0Pnnas:nss.raP/she1aawv0eeau44e92g4e/3ms±emistgB2n.nfnG8lClnei1(nl2lsha.P/P.inewloalat4l4hhh9lA2d3mddnn8sisLtd)yygss.31efCtsCnr(n-2h.,,,,:...oao4hA2Ld)g33esrf-.,, collaborators [46]. The coumarin derivative showed inhibitory activity on 15-LOX-1 in PC3 and DU145 cell lines, inducing apoptosis of the cancer cell, with the same mechanism of.
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