1/16/2015

CurcuminWikipedia,thefreeencyclopedia

Curcumin
FromWikipedia,thefreeencyclopedia

Curcumin

Enolform

Ketoform

IUPACname

methoxyphenyl)1,6

Othernames
DiferuloylmethanecurcuminIC.I.75300NaturalYellow3

Identifiers

hemapps.stolaf.edu/jmol/jmol.php?
%28%5CC%3DC%5Cc1ccc%28O%29c%28OC%29c1%29CC%28%3DO%29%5CC%3DC%5Cc2cc%28OC%29c%28O%29cc2)
SMILES
http://en.wikipedia.org/wiki/Curcumin#Demonstrated_medical_uses

1/7

1/16/2015

CurcuminWikipedia,thefreeencyclopedia

InChI

Properties

ngepowder

dataaregivenformaterialsintheirstandardstate(at25C(77F),100kPa)

(verify)(whatis: / ?)
Infoboxreferences

Curcumin(/krkjumn/)isadiarylheptanoid.Itistheprincipalcurcuminoidofturmeric,whichisa
memberofthegingerfamily(Zingiberaceae).Turmeric'sothertwocurcuminoidsaredesmethoxycurcumin
andbisdesmethoxycurcumin.Thecurcuminoidsarenaturalphenolsthatareresponsiblefortheyellow
colorofturmeric.Curcumincanexistinseveraltautomericforms,includinga1,3diketoformandtwo
equivalentenolforms.Theenolformismoreenergeticallystableinthesolidphaseandinsolution.[1]
Curcumincanbeusedforboronquantificationinthecurcuminmethod.Itreactswithboricacidtoforma
redcolorcompound,rosocyanine.
Curcuminisabrightyellowcolorandmaybeusedasafoodcoloring.Asafoodadditive,itsEnumberis
E100.[2]

Contents
1Chemistry
2Biosynthesis
3Preliminaryresearchforpotentialhealtheffects
4Bioavailability
5Potentialrisksandsideeffects

Curcumin

6Possiblediagnosticuse
7References
8Externallinks

Chemistry

http://en.wikipedia.org/wiki/Curcumin#Demonstrated_medical_uses

2/7

1/16/2015

CurcuminWikipedia,thefreeencyclopedia

Curcuminincorporatesseveralfunctionalgroups.Thearomaticringsystems,whicharephenols,are
connectedbytwo,unsaturatedcarbonylgroups.Thediketonesformstableenolsandarereadily
deprotonatedtoformenolatesthe,unsaturatedcarbonylgroupisagoodMichaelacceptorand
undergoesnucleophilicaddition.Thestructurewasfirstidentifiedin1910byJ.Miobdzka,Stanisaw
KostaneckiandWiktorLampe.[3]
Curcuminisusedasanindicatorforboron.[4]

Biosynthesis
Thebiosyntheticrouteofcurcuminhasproventobeverydifficultforresearcherstodetermine.In1973,
RoughlyandWhitingproposedtwomechanismsforcurcuminbiosynthesis.Thefirstmechanisminvolved
achainextensionreactionbycinnamicacidand5malonylCoAmoleculesthateventuallyarylizedintoa
curcuminoid.ThesecondmechanisminvolvedtwocinnamateunitscoupledtogetherbymalonylCoA.
Bothmechanismsusecinnamicacidastheirstartingpoint,whichisderivedfromtheaminoacid
phenylalanine.Thisisnoteworthybecauseplantbiosynthesesemployingcinnamicacidasastartingpoint
arerarecomparedtothemorecommonuseofpcoumaricacid.[5]Onlyafewidentifiedcompounds,such
asanigorufoneandpinosylvin,usecinnamicacidastheirstartmolecule.[6][7]Anexperimentallybacked
routewasnotpresenteduntil2008.Thisproposedbiosyntheticroutefollowsboththefirstandsecond
mechanismssuggestedbyRoughleyandWhiting.However,thelabelingdatasupportedthefirst
mechanismmodelinwhich5malonylCoAmoleculesreactwithcinnamicacidtoformcurcumin.
However,thesequencinginwhichthefunctionalgroups,thealcoholandthemethoxy,introduce
themselvesontothecurcuminoidseemstosupportmorestronglythesecondproposedmechanism.[5]
Therefore,itwasconcludedthesecondpathwayproposedbyRoughlyandWhitingwascorrect.

http://en.wikipedia.org/wiki/Curcumin#Demonstrated_medical_uses

3/7

1/16/2015

CurcuminWikipedia,thefreeencyclopedia

Preliminaryresearchforpotentialhealtheffects
Asurveyoftheliteratureshowsanumberofpotentialeffectsunderstudyandthatdailydosesovera3
monthperiodofupto12gramsweresafe.[8]
Clinicaltrialsinhumansarestudyingtheeffectofcurcuminonvariousdiseases,includingmultiple
myeloma,pancreaticcancer,myelodysplasticsyndromes,coloncancer,psoriasis,arthritis,majordepressive
disorderandAlzheimer'sdisease.[9][10][11][12][13][14]
A2014reviewofhumanclinicaltrialsfoundnobenefitto58weeksofcurcuminconsumptioncompared
toplaceboornotreatmentforpatientswithmajordepressivedisorder.[15]
Anumberoftrialsstudyingcurcuminefficacyandsafetyrevealedpoorabsorptionandlow
bioavailability.[11]

Bioavailability
InPhaseIclinicaltrials,dietarycurcuminwasshowntoexhibitpoorbioavailability(i.e.,lowlevelsin
plasmaandtissues).[16]Potentialfactorsthatlimitthebioavailabilityofcurcuminincludeinsolubilityin
water(moresolubleinalkalinesolutions),poorabsorption,rapidmetabolismandsystemicelimination.
Numerousapproachestoincreasingcurcuminbioavailabilityhavebeenexplored,includingtheuseof
absorptionfactorssuchaspiperine.[16]Becauseofitsstabilityandphysicalproperties,purecurcumincan
bevaporizedorsmoked,obviatingtheneedfororalabsorptionfactors.ThisROAhowevercarrieshigher
riskofchelatingironfromhemoglobin,andpotentiallyhigherriskofcarcinogenicity.
Thebioavailabilityofcurcuminingestedinfoodsmaybeincreasedasaresultofcookingordissolutionin
oil.[17]

Potentialrisksandsideeffects
Clinicalstudiesinhumanswithhighdoses(212grams)ofcurcuminhaveshownfewsideeffects,[18]with
somesubjectsreportingmildnauseaordiarrhea.[19]Morerecently,curcuminwasfoundtoalteriron
metabolismbychelatingironandsuppressingtheproteinhepcidin,potentiallycausingirondeficiencyin
susceptiblepatients.[20]

Possiblediagnosticuse
PreliminaryresearchhasfoundthatcurcuminoidbindstoamyloidproteinsassociatedwithAlzheimer's
disease.[21]Becausecurcuminincreasesfluorescentactivityafteritbindstoamyloidprotein,curcuminis
beingstudiedasapossibleidentifier.Testshavedetectedamyloidproteinsinhumaneyes,offeringthe
possibilitythatsimpleeyeexamscouldprovideearlydetectionofthedisease.[22][23]

References
http://en.wikipedia.org/wiki/Curcumin#Demonstrated_medical_uses

4/7

1/16/2015

CurcuminWikipedia,thefreeencyclopedia

Notes
1. ^Manolova,YanaDeneva,VeraAntonov,LiudmilatalMomekova,DenitsaLambov,Nikolay(2014)."The
effectofthewateronthecurcumintautomerism:Aquantitativeapproach".SpectrochimicaActa132A(1):815
820.Bibcode:2014AcSpA.132..815M(http://adsabs.harvard.edu/abs/2014AcSpA.132..815M).
doi:10.1016/j.saa.2014.05.096(http://dx.doi.org/10.1016%2Fj.saa.2014.05.096).
2. ^EuropeanCommission."FoodAdditives"(https://webgate.ec.europa.eu/sanco_foods/main/?
event=substance.view&identifier=5).Retrieved20140215.
3. ^Miobdzka,J.v.Kostanecki,St.Lampe,V.(1910)."ZurKenntnisdesCurcumins".Berichtederdeutschen
chemischenGesellschaft43(2):216370.doi:10.1002/cber.191004302168
(http://dx.doi.org/10.1002%2Fcber.191004302168).
4. ^"EPAMethod212.3:Boron(Colorimetric,Curcumin)"(http://www.caslab.com/EPAMethods/PDF/EPA
Method2123.pdf).
5. ^abcKita,TomokoImai,ShinsukeSawada,HiroshiKumagai,HidehikoSeto,Haruo(2008)."The
BiosyntheticPathwayofCurcuminoidinTurmeric(Curcumalonga)asRevealedby13CLabeledPrecursors".
Bioscience,Biotechnology,andBiochemistry72(7):1789.doi:10.1271/bbb.80075
(http://dx.doi.org/10.1271%2Fbbb.80075).
6. ^Schmitt,BettinaHlscher,DirkSchneider,Bernd(2000)."Variabilityofphenylpropanoidprecursorsinthe
biosynthesisofphenylphenalenonesinAnigozanthospreissii".Phytochemistry53(3):3317.
doi:10.1016/S00319422(99)005440(http://dx.doi.org/10.1016%2FS00319422%2899%29005440).
PMID10703053(https://www.ncbi.nlm.nih.gov/pubmed/10703053).
7. ^Gehlert,R.Schoeppner,A.Kindl,H.(1990)."StilbeneSynthasefromSeedlingsofPinussylvestris:
PurificationandInductioninResponsetoFungalInfection"
(http://www.apsnet.org/publications/mpmi/backissues/Documents/1990Articles/Microbe03_444.pdf)(pdf).
MolecularPlantMicrobeInteractions3(6):444449.doi:10.1094/MPMI3444
(http://dx.doi.org/10.1094%2FMPMI3444).
8. ^Goel,AjayKunnumakkara,AjaikumarB.Aggarwal,BharatB.(2008)."Curcuminas"Curecumin":From
kitchentoclinic".BiochemicalPharmacology75(4):787809.doi:10.1016/j.bcp.2007.08.016
(http://dx.doi.org/10.1016%2Fj.bcp.2007.08.016).PMID17900536
(https://www.ncbi.nlm.nih.gov/pubmed/17900536)."PilotphaseIclinicaltrialshaveshowncurcumintobesafe
evenwhenconsumedatadailydoseof12gfor3months."
9. ^Hatcher,H.Planalp,R.Cho,J.Torti,F.M.Torti,S.V.(2008)."Curcumin:Fromancientmedicineto
currentclinicaltrials".CellularandMolecularLifeSciences65(11):163152.doi:10.1007/s0001800874524
(http://dx.doi.org/10.1007%2Fs0001800874524).PMID18324353
(https://www.ncbi.nlm.nih.gov/pubmed/18324353).
10. ^Yan,JiaoWilkinson,Di,Wang,Hatcher,Kock,D'Agostino,Jr,Knovich,Torti,Torticorrespondingauthor(8
January2009)."RedCells,Iron,andErythropoiesisCurcumin,acancerchemopreventiveand
chemotherapeuticagent,isabiologicallyactiveironchelator"
(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2615657).Blood.113(2):(Prepublishedonline2008September
24.):462469.doi:10.1182/blood200805155952(http://dx.doi.org/10.1182%2Fblood200805155952).
PMC2615657(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2615657).PMID18815282
(https://www.ncbi.nlm.nih.gov/pubmed/18815282).

http://en.wikipedia.org/wiki/Curcumin#Demonstrated_medical_uses

5/7

1/16/2015

CurcuminWikipedia,thefreeencyclopedia

(https://www.ncbi.nlm.nih.gov/pubmed/18815282).
11. ^ab"ClinicalTrials.gov:Currentclinicaltrialsoncurcumin"(http://clinicaltrials.gov/ct2/results?
term=curcumin&pg=1).USNationalInstitutesofHealth,ClinicalTrialRegistry.2013.
12. ^Zhao,LN.Chiu,SW.Benoit,J.Chew,LY.Mu,Y.(Jun2012)."Theeffectofcurcuminonthestabilityof
Adimers".JPhysChemB116(25):742835.doi:10.1021/jp3034209
(http://dx.doi.org/10.1021%2Fjp3034209).PMID22690789(https://www.ncbi.nlm.nih.gov/pubmed/22690789).
13. ^Sanmukhani,JSatodia,VTrivedi,JPatel,TTiwari,DPanchal,BGoel,ATripathi,C.B.(2014).
"Efficacyandsafetyofcurcumininmajordepressivedisorder:Arandomizedcontrolledtrial".Phytotherapy
Research28(4):57985.doi:10.1002/ptr.5025(http://dx.doi.org/10.1002%2Fptr.5025).PMID23832433
(https://www.ncbi.nlm.nih.gov/pubmed/23832433).
14. ^Mancuso,C.Barone,E.(2009)."Curcumininclinicalpractice:mythorreality?".TrendsinPharmacological
Science30(7):333334.doi:10.1016/j.tips.2009.04.004(http://dx.doi.org/10.1016%2Fj.tips.2009.04.004).
PMID19523696(https://www.ncbi.nlm.nih.gov/pubmed/19523696).
15. ^Andrade,Chittaranjan(2014)."Acriticalexaminationofstudiesoncurcuminfordepression".TheJournalof
ClinicalPsychiatry75(10):e11101112.doi:10.4088/JCP.14f09489
(http://dx.doi.org/10.4088%2FJCP.14f09489).PMID25373119
(https://www.ncbi.nlm.nih.gov/pubmed/25373119).
16. ^abAnand,P.Kunnumakkara,A.B.Newman,R.A.Aggarwal,B.B.(2007)."Bioavailabilityofcurcumin:
problemsandpromises".MolecularPharmaceutics4(6):807818.doi:10.1021/mp700113r
(http://dx.doi.org/10.1021%2Fmp700113r).PMID17999464(https://www.ncbi.nlm.nih.gov/pubmed/17999464).
17. ^Marczylo,T.H.Verschoyle,R.D.Cooke,D.N.Morazzoni,P.Steward,W.P.Gescher,A.J.(2007).
"Comparisonofsystemicavailabilityofcurcuminwiththatofcurcuminformulatedwithphosphatidylcholine".
CancerChemotherapyandPharmacology60(2):171177.doi:10.1007/s002800060355x
(http://dx.doi.org/10.1007%2Fs002800060355x).PMID17051370
(https://www.ncbi.nlm.nih.gov/pubmed/17051370).
18. ^Cheng,A.L.Hsu,C.H.Lin,J.K.Hsu,M.M.Ho,Y.F.Shen,T.S.Ko,J.Y.Lin,J.T.Lin,B.R.
MingShiang,WYu,H.S.Jee,S.H.Chen,G.S.Chen,T.M.Chen,C.A.Lai,M.K.Pu,Y.S.Pan,M.
H.Wang,Y.J.Tsai,C.C.Hsieh,C.Y.(2001)."PhaseIclinicaltrialofcurcumin,achemopreventiveagent,
inpatientswithhighriskorpremalignantlesions".Anticancerresearch21(4B):2895900.PMID11712783
(https://www.ncbi.nlm.nih.gov/pubmed/11712783).
19. ^Hsu,C.H.Cheng,A.L.(2007)."Clinicalstudieswithcurcumin".AdvancesinExperimentalMedicineand
Biology.ADVANCESINEXPERIMENTALMEDICINEANDBIOLOGY595:471480.doi:10.1007/9780
387464015_21(http://dx.doi.org/10.1007%2F9780387464015_21).ISBN9780387464008.
PMID17569225(https://www.ncbi.nlm.nih.gov/pubmed/17569225).
20. ^JiaoYetal.(January2009)."Curcumin,acancerchemopreventiveandchemotherapeuticagent,isa
biologicallyactiveironchelator"(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2615657).Blood113(2):462
469.doi:10.1182/blood200805155952(http://dx.doi.org/10.1182%2Fblood200805155952).PMC2615657
(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2615657).PMID18815282
(https://www.ncbi.nlm.nih.gov/pubmed/18815282).
21. ^Yanagisawa,D.TaguchiHYamamotoAShiraiNHiraoKTooyamaI.(2011)."Curcuminoidbindsto
amyloid142oligomerandfibril"(http://www.ncbi.nlm.nih.gov/pubmed/21335654).JournalofAlzheimer's
Disease.24Suppl2:3342.doi:10.3233/JAD2011102100(inactive20150111).PMID21335654
http://en.wikipedia.org/wiki/Curcumin#Demonstrated_medical_uses

6/7

1/16/2015

CurcuminWikipedia,thefreeencyclopedia
Disease.24Suppl2:3342.doi:10.3233/JAD2011102100(inactive20150111).PMID21335654

(https://www.ncbi.nlm.nih.gov/pubmed/21335654).RetrievedJuly13,2014.
22. ^SmellAndEyeTestsMightDetectAlzheimer'sEarly
(http://www.science20.com/news_articles/smell_and_eye_tests_might_detect_alzheimers_early140457),retrieved
July13,2014
23. ^"EyetestscoulddetectearlyAlzheimer's:ResearcherssayAlzheimer'smarkercanbedetectedinretinaand
lensofeye"(http://www.theguardian.com/society/2014/jul/13/eyetestsdetectearlyalzheimersretinalens).The
Guardian.July13,2014.RetrievedJuly13,2014.

Externallinks
Turmericandcurcumin(http://www.mskcc.org/mskcc/html/11571.cfm?RecordID=429&tab=HC),
fromMemorialSloanKetteringCancerCenter
Turmericandcurcumin(http://www.mdanderson.org/departments/cimer/dindex.cfm?pn=915cd45e
7c3743058e778e10de640e0c),fromM.D.AndersonCancerCenter
Turmeric(http://www.umm.edu/altmed/articles/turmeric000277.htm),fromtheUniversityof
MarylandMedicalCenter
Retrievedfrom"http://en.wikipedia.org/w/index.php?title=Curcumin&oldid=642049157"
Categories: Curcuminoids Antiinflammatoryagents Phenolantioxidants Biologicallybasedtherapies
Experimentalmedicaltreatments Monoamineoxidaseinhibitors Naturaldyes Foodcolorings
Fishembryotoxins
Thispagewaslastmodifiedon11January2015,at19:41.
TextisavailableundertheCreativeCommonsAttributionShareAlikeLicenseadditionaltermsmay
apply.Byusingthissite,youagreetotheTermsofUseandPrivacyPolicy.Wikipediaisa
registeredtrademarkoftheWikimediaFoundation,Inc.,anonprofitorganization.

http://en.wikipedia.org/wiki/Curcumin#Demonstrated_medical_uses

7/7