a n ew met h od for t h e est i mat i ... - world olive center
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A new method for the estimation of olive oil healthfulness
Article ¡ April 2013
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Prokopios Magiatis
National and Kapodistrian University of Athens
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Evangelia Karkoula
National and Kapodistrian University of Athens
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Eleni Melliou
National and Kapodistrian University of Athens
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Several epidemiological studies have shown that the traditional Mediterranean diet is associated with a lower incidence of athero-sclerosis, cardiovascular disease, neurodegen-erative diseases, and certain kinds of cancer. These appreciable health-promoting proper-ties have been partially correlated with the regular consumption of extra virgin olive oil as the principal source of fat. Olive oil is the most famous agricultural product in the Mediter-ranean, with a history as old as that regionâs civilization. Olive fruits and olive oil not only are delicious but also have been considered as medicines since ancient times.
of olive oil healthfulnessA new method for the estimation
Evangelia Karkoula, Eleni Melliou, and Prokopios Magiatis⢠A growing body of evidence suggests that
the healthfulness of olive oils could be clas-sified based on their content of oleocanthal, oleacein, and related secoiridoids. However, such compounds are difficult to measure be-cause they react with the water or methanol used during the mobile phase of liquid chro-matography.
⢠Recently, a new method allowing olive oil polyphenols to be extracted without the use of reacting solvent was developed, making it possible to measure oleocanthal and olea-cein levels directly by quantitative 1H nucle-ar magnetic resonance (NMR) in CDCl3 at 600 MHz and 800 MHz.
⢠Measurements of 300 olive oil samples using this method revealed wide variations in the concentrations of these healthful com-pounds among extra virgin olive oils.
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of olive oil healthfulness
Dioscoridesâ(ca.â40â90âce)âandâseveralâotherâancientâdoctorsâclaimedâthatâoliveâoilâandâotherâolive-relatedâproductsâhadânumerousâtherapeuticâapplications.âInâhisâmonumentalâworkââDeâMateriaâMedica,ââwhichâisâtheâbasisâofâmodernâpharmacol-ogyâandâpharmacopoeia,âDioscoridesâclearlyâstatedâthatâoliveâoilâfromâspecificâvarietiesâparticularlyâearly-harvestedâextraâvirginâoliveâoilâhasâanti-inflammatoryâactivities.âAncientârecipesâdescribedâinâincredibleâdetailâhowâoliveâoilâcouldâbeâusedâasârem-ediesâagainstâconditionsâsuchâasâheadacheâandâtoothache,âclearâindicationsâofâin vivo anti-inflammatoryâactivity.âYet,âaccordingâtoâdescriptionsâinâancientâmanuscripts,ânotâallâoliveâoilsâdisplayâsuchâproperties.âWeâwereâintriguedâandâdecidedâtoâinvestigateâwhetherâthatâcouldâbeâtrueâandâwhy.
Inâ2005âBeauchampâandâco-workersâreportedâ inâtheâjournalâNatureâthatâoliveâoilâcontainsâaâchemicalâcompoundâcalledâoleocanthal,âwhichâisâresponsibleâforâtheâpungencyâofâsomeâoliveâoilsâandâwhichâhasâaâveryâstrongâanti-inflammatoryâactivityâwithâibuprofen-likeâcyclooxygenaseâ(COX-1âandâCOX-2)-inhibitingâactivity.âThisâmayâexplainâtheâtherapeuticâprop-ertiesâofâvirginâoliveâoil,âsinceâinflammationâplaysâaâsignificantâroleâinâtheâdevelopmentâofânumerousâchronicâdiseases,âsuchâasâcardiovascularâdisease,âasâwellâasâinâcertainâkindsâofâcancer.â
Inâaddition,ârecentâresearchâhasâdemonstratedâthatâoleo-canthalâisâaâpromisingâtherapeuticâagentâforâtheâtreatmentâofâinflammatoryâdegenerativeâjointâdiseases.âMoreover,âoleocan-thalâcanâbeâaâpotentiallyâusefulâagentâforâtheâdevelopmentâofânewâtreatmentsâforâneurodegenerativeâtauopathiesâ(diseasesâassociatedâwithâtheâpathologicalâaggregationâofâtauâproteinâinâtheâhumanâbrain),âsuchâasâAlzheimerâsâdisease,âorâasâanâagentâagainstâHelicobacter pylori,âwhichâisâlinkedâtoâaâmajorityâofâpepticâulcersâandâtoâsomeâtypesâofâgastricâcancer.âOleocanthalâalsoâexhibitsâbiologicalâpropertiesâthatâcanâcontrolâskinâagingâandâaâgrowingâbodyâofâevidenceâsuggestsâthatâitâcouldâbeâusedâtoâtreatâdamagedâskinâorâtoâreduceâaâvarietyâofâdisordersâthatâariseâfromâmetabolicâsyndrome.
Anotherâcompoundâwithâaâsimilarâstructureâthatâisârelatedâtoâtheâbitterâtasteâofâsomeâoliveâoilsâisâtheâdialdehydicâformâofâdecarboxymethylâoleuropeinâaglycone,âknownâasâoleacein.âThisâcompoundâhasâshownâactivitiesâsimilarâtoâthoseâofâoleocan-thal,âbutâtheâformerâhasâalsoâdisplayedâsignificantâanti-breastâcancerâproperties.âMostâimportantly,âoleaceinâalsoâhasâpotentâantioxidantâactivities,âevenâbetterâthanâthoseâofâhydroxytyro-sol,âanotherâactiveâcompoundâfoundâinâtableâolivesâandâoliveâoil.âOleaceinâcanâadditionallyâprotectâlowâdensityâlipoproteinâfromâoxidation,âaâhealthâclaimâalreadyârecognizedâbyâEuropeanâUnionâlegislation.â
Modernâfindingsâaboutâoleocanthalâandâoleaceinâandâtheirâpotentialâhealthâeffectsâthatâconfirmedâtheâancientâreportsâpromptedâusâtoâassumeâthatâseveralâvarietiesâofâoliveâoilsâcouldâbeâclassifiedâonâtheâbasisâofâtheirâcontentâofâsecoiridoids,âsuchâasâoleocanthal,âoleacein,âandârelatedâcompounds.âTowardâthisâend,âweâinvestigatedâtheâlevelsâofâoleocanthalâandâitsârelatedâanalogâoleaceinâinâaâlargeânumberâofâGreekâandâCaliforniaâoliveâoilsâofâmonovarietalâoriginâinârelationâwithâtheâvariety,âtheâgeo-graphicâorigin,âandâtheâtimeâofâharvest.âToâachieveâthisâtarget,âweârecognizedâtheâneedâtoâdevelopâaânew,âfast,âandâaccurateâanalyticalâmethodâthatâcanâcircumventâaâpreviouslyâknownâana-lyticalâproblemâforâtheâoleocanthalâandâoleaceinâmeasurement.â
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Thatâproblemâarisesâbecauseâbothâcompoundsâreactârapidlyâwithâtheâwaterâorâmethanolâcommonlyâusedâinâtheâmobileâphaseâofâliquidâchromatography,âleadingâtoâbroadenedâorâmul-tipleâpeaks.âThisâreactivityânecessitatesâtheâuseâofâderivatiza-tionâreactions.
Forâthisâreason,âweâdevelopedâmethodsâtoâextractâoliveâoilâpolyphenolsâwithoutâusingâanyâreactingâsolventâandâtoâmeasureâoleocanthalâandâoleaceinâlevelsâdirectlyâbyâquantita-tiveâ1H-NMRâinâCDCl3âatâ600âMHzâandâ800âMHzâ(Fig.â1).â
Theâmethodsâwereâappliedâinâtheâstudyâofâoverâ300âoliveâoilâsamples.âOneâofâtheâmainâfindingsâwasâaâhighlyâimportantâvaria-tionâinâtheâconcentrationsâofâoleocanthalâandâoleaceinâamongâtheâstudiedâextraâvirginâoliveâoilâsamples.âTheâconcentrationsâofâbothâcompoundsârangedâfromânonâdetectableâtoâoverâ500âmg/kg,ârespectively,âandâtheirâsumâfromâ0âmg/kgâtoâoverâ750âmg/kg.â
ItâisâimportantâtoânoteâthatâaccordingâtoâtheâdefinitionâestablishedâbyâEuropeanâUnionâlegislationâallâtheâstudiedâsamplesâwereâconsideredâasâextraâvirginâoliveâoils.âHowever,âtheâobservedâimportantâvariationâofâtheâconcentrationâofâtheâbioac-tiveâpolyphenolicâsecoiridoidsârevealedâtheâneedâforâaânewâtypeâofâclassificationâespeciallyârelatedâtoâpossibleâhealthâclaimsâofâ
FIG. 1. Example of two 1H nuclear magnetic resonance spectra of extra virgin olive oils presenting high and low levels of oleocanthal and oleacein. The arrows denote the peaks that are used for the quantification of each compound (IS: internal standard).
⢠Beauchamp, G.K., R.S.J. Keast, D. Morel, J. Lin, J. Pika, Q. Han, C. Lee, A.B. Smith, and P.A.S. Breslin, Phyto-chemistry: ibuprofen-like activity in extra-virgin olive oil, Nature 437:45â46 (2005).
⢠Cicerale, S., L.J. Lucas, and R.S.J. Keast, Oleocanthal: a naturally occurring anti-inflammatory agent in vir-gin olive oil, in Olive OilâConstituents, Quality, Health Properties and Bioconversions, edited by B. Dimitrios, ISBN: 978-953-307-921-9, InTech (2012). Available from http://tinyurl.com/oleocanthal.
⢠EFSA Journal 9(4), 2033 (2011). Available at http://www.efsa.europa.eu/en/efsajournal/doc/2033.pdf.
⢠Karkoula, E., A. Skantzari, E. Melliou, and P. Magiatis, Direct measurement of oleocanthal and oleacein lev-els in olive oil by quantitative 1H-NMR. Establishment of a new index for the characterization of extra virgin olive oils, J. Agric. Food Chem. 60:11696â11703 (2012).
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thoseâcompounds.âForâthisâreasonâweâproposeâaânewâindex,âD1,âasâtheâsumâofâtheâconcentrationsâofâoleocanthalâandâoleacein.
GREEK OIL SAMPLESTheâhighestâconcentrationsâofâoleocanthalâandâoleaceinâamongâtheâGreekâsamplesâwereârecordedâinâoliveâoilâsamplesâproducedâfromâtheâKoroneikiâcultivar.âHowever,âaâportionâofâoliveâoilâsamplesâcomingâfromâcvâKoroneikiâshowedâsignificantlyâlowâconcentrationsâ(Fig.â2).âThisâresultâinâmostâcasesâcouldâbeâattrib-utedâeitherâtoâveryâlateâharvestâ(fullyâripeâfruit)âorâtoâhighâtem-peratureâduringâmalaxationâorâboth.
Weâalsoâfoundâthatâthereâwasâaâgroupâofâoliveâvarietiesâthat,âindependentâofâgeographicâorigin,âharvestâtimeâ(earlyâorâlate),âorâoliveâmill-relatedâparameters,âproducedâoliveâoilâcontainingâbothâcompoundsâinâlowâlevelsâ(meanâvalueâD1â=â49âmg/mg).âTheâoliveâoilâproducedâbyâthoseâvarietiesâisâtraditionallyâpre-ferredâforâconfectionaryâowingâtoâitsâlowerâsensationâofâbitter-nessâandâpungency.âOurâfindingsâconfirmedâtheirâlowerâcontentâofâoleocanthalâandâoleacein,âwhichâareârelatedâwithâthoseâspecificâorganolepticâproperties.
Anotherâobservationâwasâthatâtheâratioâbetweenâoleocan-thalâandâoleaceinâ(indexâD2â=âoleacein/oleocanthal)âseemsâtoâbeâdependentâonâtheâoliveâtreeâvariety,âprobablyâdueâtoâgeneticâreasons,âandâindependentâofâtheâoliveâmillâprocedure.â
Weâalsoâdiscoveredâaâpositiveâcorrelationâofâoleocanthalâandâoleaceinâconcentrationâwithâtheâearlyâtimeâofâharvest.âItâisânote-worthyâthatâtheâhighestâD1âindexâ(750âmg/kg)âwasârecordedâforâaâsampleâfromâKoroneikiâvarietyâ(AntiparosâIsland)âproducedâinâlateâOctoberâ2012.âSimilarly,âtheâsecond-âandâthird-highestâD1âindexesâwereârecordedâforâearly-harvestedâ(earlyâNovember)âKoroneikiâvarietyâfromâMessini.âTheâsameâvarietyâfromâtheâsameâoliveâgroveâcollectedâafterâtwoâmonthsâandâprocessedâinâtheâsameâoliveâmillâunderâtheâsameâconditionsâaffordedâanâoliveâoilâwithâD1âindexâatâ87âmg/kg.â
CALIFORNIA OIL SAMPLESSimilarlyâtoâtheâGreekâsamples,âsignificantâdifferencesâwereâalsoâobservedâforâtheâCaliforniaâoliveâoilâsamples.âSamplesâfromâsevenâdifferentâvarietiesâwereâstudied,âandâbigâdifferencesâwereârecorded.âForâexample,âtheâhighestâvariabilityâinâD1âindexâwasâfoundâforâTaggiasca,âLeccinoâandâBarouniâcultivars,ârangingâfromâ45âtoâ275âtoâ406âmg/kg,ârespectively.
Althoughâweâmeasuredâonlyâtwoâcompoundsâbearingâalde-hydeâgroups,âtheâNMRâspectrumâinâtheârangeâ9.1â9.8âppmâseemsâtoâpresentâaâuniqueârecognitionâpatternâespeciallyâcharacteris-ticâforâsomeâoliveâoilâvarieties.âTheâ1H-NMRâspectrumânotâonlyâ
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offersâaâmethodâforâquantitationâbutâalsoâoffersâaâtoolâforâvarietyârecognitionâbutâthisâfindingâneedsâfurtherâelaboration.
Whileâthereâisâneedâforâmoreâextensiveâstudy,âbasedâonâourâobservationsâtheânewâindexâforâtheâcharacterizationâofâextraâvirginâoliveâoilsâaâcombinationâofâD1â=âoleocanthalâ+âoleaceinâlevelâwithâtheâD2â=âoleocanthal/oleaceinâmolarâratioâcanâbeâveryâusefulâforâtheâestimationâofâtheâhealthfulnessâofâanâoliveâoilâandâcanâbeâunderstoodâeasilyâbyâconsumers.
INDEXES D1 AND D2 IN PERSPECTIVEInâconfirmingâtheâancientâobservations,âitâwasâobviousâthatâtheâoilsâcanâbeâcategorizedâaccordingâtoâtheirâcontentâofâbioactiveâ
compounds.âTheânewâindexesâD1âandâD2âreflectâsuchâsignificantâdifferencesâamongâtheâoliveâoilsâthatâalthoughâtheâoilsâmayâbelongâtoâtheâofficialâcategoryâofâextraâvirginâoliveâoil,âaânewâsubcategoryâofââsuperââoliveâoilsâwithâhighâD1âandâD2âcanâbeâestablished.âItâhasâtoâbeâclearâthatâthoseâindexesâmainlyâconcernâtheâsupportâofâhealthâclaimsâandâareâmoreâspecificâthanâtheâtotalâpolyphenolsâ(expressedâasâgallicâacidâequivalent)ârelatedâtoâantioxidantâactivity.
ItâisâalsoânoteworthyâthatâinâpreliminaryâstudiesâtheâindexesâD1âandâD2âcanâpredictâtheâpungentâandâbitterâtasteâofâanâoliveâoil.âInâmostâcasesâtheâhighestââhealthfulnessââisârelatedâwithâincreasedâpungencyâandâbitterness,âwhichâareâorganolepticâpropertiesâthatâareâhighlyâappreciatedâbyâoliveâoilâexperts.
Prokopios Magiatis is an assistant professor in the laboratory of pharmacognosy and natural products chemistry at the Univer-sity of Athens. He can be contacted at [email protected]. Evangelia Karkoula is a graduate student in the laboratory of pharmacognosy and natural products chemistry at the Uni-versity of Athens.
Eleni Melliou is a visiting scientist at the UC Davis Olive Cen-ter at the University of California in Davis, California, USA.
FIG. 2. Diagram showing the wide variability of oleocanthal and oleacein content among the several varieties studied.
Mayonnaise is said to be the invention of the French chef of the Duke de Richelieu in 1756. While the Duke was defeating the British at Port Mahon, his chef was creating a victory feast that included a sauce made of cream and eggs. When the chef real-ized that there was no cream in the kitchen, he improvised, sub-stituting olive oil for the cream. A new culinary masterpiece was born, and the chef named it "Mahonnaise" in honor of the Duke's victory. (Copied from http://www.bestfoods.com/home/about)
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