Department of Food Science, Via Sondrio 2/a, University of Udine, Udine, Italy

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1 Influence of mlxtion time on phenols nd voltile compounds of virgin olive oil otined from phenol enriched olive pste (Buž cv.) Vlerij Mjetić Germek, Oliver Koprivnjk, Bojn Butinr, Loren Pizzle c, Milen Bučr- Miklvčič d,lnfrnco S. Conte c Deprtment of Food Technology nd Control, Fculty of Medicine, University of Rijek, Brće Brnchett 20, Rijek, Croti (vmjetic@medri.hr, oliver.koprivnjk@medri.uniri.hr) Lortory for Oil Testing, Institute for Oliveculture, Science nd Reserch Centre, University of Primorsk, Zelen ulic 8c, 6310 Izol, Sloveni (ojn.utinr@zrs.upr.si) c Deprtment of Food Science, Vi Sondrio 2/, University of Udine, Udine, Itly (loren.pizzle@uniud.it, lnfrnco.conte@uniud.it) d Institute for Ecology, Olive Oil nd Control, LABS LLC, Zelen ulic 8, 6310 Izol, Sloveni (milen.miklvcic@guest.rnes.si) ABSTRACT The mlxtion of olive pste is n essentil olive oil production step which llows not only stisfctory yields of oil extrction. During mlxtion, chnges of oil composition lso occur ecuse of the prtition phenomen mong oil, wter nd solid phse nd the ctivity of fruit enzymes relesed during crushing. Qulity nd quntity of extrcted oil cn e influenced y vrying the conditions of this opertion (such s time, temperture, ddition of technologicl codjuvnts). Different mlxtion times (30, 45 nd 60 min) were pplied to olive pste of Buž cultivr which ws previously enriched with the phenolic extrct otined from the freeze-dried olive pulp of Istrsk Bjelic cultivr. Olive pste ws phenol enriched t the level of 38% (w/w) in order to improve the phenolic content in resulting oils nd to check the influence on voltile compounds. Phenols in olive pstes nd corresponding olive oils were determined y RP HPLC with UV-DAD detection, wheres voltile compounds in oils were nlyzed y SPME-GC-MS. An ddition of phenolic extrct to olive pste mostly ffected the mounts of dildehydic form of oleuropein glycone nd pigenin which incresed y 473% nd 90% in Buž pste, respectively. The mjor phenolic compound in olive pste ws dildehydic form of decroxymethyloleuropein glycone, s well s in the oil. By incresing the mlxtion time, the decrese of free hydroxytirosol, tyrosol nd verscoside in enriched olive pste ws oserved. The similr ws oserved for oil smples, except for vnillin which incresed (y 31%) long with the mlxtion time. Among voltile compounds responsile for positive odour notes, the prolonged mlxtion time hd significnt negtive effect (Tukey s test, p<0.05) on hexnl, hexn-1-ol nd Z-3-hexenyl cette. Longer mlxtion time (60 min) of olive pste enriched with the phenolic extrct showed more pronounced effect on phenols thn on voltile compounds. Keywords: Buž cultivr; mlxtion time; olive oil; phenols; voltiles INTRODUCTION Voltile nd phenolic compounds re lrgely responsile for the complex nd desirle flvour of virgin olive oils (VOOs). Although the synthesis nd iotrnsformtion of these compounds minly tke plce during the olive fruit tissue disruption in the crushing step of the VOO production process (Inrejos-Grcí et l., 2011), these rections lso continue during the mlxtion of olive pste (Clodoveo, 2012). During the mlxtion step noticele chnges in VOO s chemicl composition occur ecuse of the prtition phenomen of minor compounds etween oil nd wter phses nd the ctlytic ctivities of endogenous enzymes, which re relesed in the moment of the crushing. Mlxtion conditions, such s time nd temperture, influence not only oil yield ut lso the voltile nd phenol composition of finl VOOs (Angeros et l., 2001; Rnlli et l., 2003; Gomez-Rico et l., 2009). Voltile compounds, responsile for the plesnt green nd fruity odour notes of VOOs, re synthesised through the lipoxygense pthwy from free polyunsturted ftty cids. Linoleic nd linolenic ftty cid, detched y cyl hydrolse, re oxidized y lipoxygense (LOX) nd cleved y hydroperoxide lyse (HPL) into C6 ldehydes, which cn e lter reduced to C6 lcohols y lcohol dehydrogense (ADH) nd trnsformed to C6 esters y lcohol cyl trnsferse (AAT) (Olís et l., 1993). Besides hydroperoxides formtion, LOX cn cleve them producing lkoxy rdicls which led to C5 voltile compounds formtion tht re contriutors to green, sweet nd pungent sensory perceptions (Angeros et l., 2000).

2 During processing, considerle chnges of the olive phenolic compounds tke plce due to the endogenous enzyme ction. Sánchez-Ortiz et l. (2012) tested the effect of reltively high dose of synthetic phenol ntioxidnts, which re known s LOX inhiitors, on the synthesis of Arequin nd Picul VOO voltile compounds. In this study the impct of the incresed level of phenolic compounds nturlly present in olive fruits on the voltile compounds formtion nd the VOO phenol content ws exmined. Moreover, different mlxtion times (30, 45 nd 60 min) were pplied to phenol enriched olive pste of Buž cultivr in order to improve the phenolic content in resulting oils nd to check the influence on VOO voltile nd phenolic compounds. MATERIALS & METHODS Olive fruits. Olive fruits of the cultivr Istrsk Bjelic (mturity index, MI=0.7) nd the cultivr Buž (MI=4.0) were hndpicked during Octoer nd Novemer of Fruits of Istrsk Bjelic were used to otin n queous solution of phenolic compounds intended for enrichment of Buž olive pste. Preprtion of the queous solution of phenolic compounds. The queous solution of phenolic compounds were prepred from the pulp of previously freeze-dried Istrsk Bjelic fruits using methnol s the extrction solvent, ccording to the procedure descried y Mjetić Germek et l. (2013). VOO smples preprtion. Oil smples from Buž fruits were prepred using the lortory plnt (Aencor, MC2 Ingeneri y Sistems, Spin) consisting of the hmmer crusher, thermostted verticl olive pste mixers nd the centrifuge. After fruit milling, n pproprite volume of the queous solution of phenolic compounds ws dded to the olive pste in order to increse the phenolic content y 30% (w:w) ccording to the colorimetric determintion of the totl phenols mss frction. Control smples were otined y the ddition of the sme volume of distilled wter. Enriched olive pstes were mlxed for 30, 45 nd 60 min t 25 ± 0.5 C. Oil smples were extrcted y centrifugtion t 3600 rpm for 70 s nd stored in the fully filled drk ottles t room temperture efore eing nlysed. Two independent oil extrction procedures were performed for ech oil smple. Colorimetric determintion of the totl phenols mss frction in olive pste nd the queous solution. The totl phenol mss frction in oth mtrices ws determined in order to define the mount of the queous solution to e dded to olive pste. Totl phenols were determined colorimetriclly using Folin-Cioclteu regent s descried in our previous work (Mjetić Germek et l., 2013). Determintion of phenols composition of the olive pste nd olive oil smples. Phenols were extrcted from freeze-dried olive pstes ccording to the procedure descried y Vlenčič et l. (2010). Phenols extrcted from the olive pste nd olive oil smples were determined y RP HPLC with UV-DAD detection (Agilent Technologies 1100 series HPLC, Germny) ccording to slightly modified method pulished y Interntionl Olive Council (2009). Tyrosol, pigenin nd luteolin were used s clirtion stndrds nd syringic cid s n internl stndrd. For ech smple four nlyses were crried out. Anlysis of voltile compounds. The SPME smpling procedure descried y Vichi et l. (2003) ws used. Gs chromtogrph (Shimtzu 2010, Jpn) equipped with Supelco equity 5 cpillry column 60 m 0.25 mm i.d., 1 µm film tickness (Supelco, USA), nd qudrupole mss detector Shimdzu QP2010 (Jpn) were used. A detiled description of nlysis of voltile compounds is provided in our previous work (Mjetić Germek et l., 2013). Voltile compounds were semiquntitted using the reltive response fctor of internl stndrd 4-methyl-2-pentnol nd expressed s mg/kg of oil. Ech smple ws nlysed in two prllel repetitions. Sttisticl nlysis. Differences mong smples with different mlxtion time were tested y onewy nlysis of vrince t 5% significnce level. The homogeneity of vrince ws tested y the Brown-Forsythe test. The men vlues were compred y Tukey s honest significnt difference test (p<0.5). Sttisticl nlyses were performed using the softwre pckge Sttistic 10.

3 RESULTS & DISCUSSION For this study, Buž cultivr ws selected on the sis of its reltively low phenols content nd high content of voltile compounds (Škevin et l., 2003; Brkić Buol et l., 2012). Becuse of these chrcteristics Buž olive pste ws considered suitle mtrix for the enrichment with phenols in order to improve the phenolic content in resulting oils nd to check the influence of mlxtion time on phenolic nd voltile compounds. For the olive pste enrichment, phenolic compound were extrcted from the pulp of freeze-dried unripe fruits of Istrsk Bjelic (MI=0.7), known s cultivr with high phenols content (Vlenčič et l., 2010). After enrichment of Buž olive pste, n increse of totl phenols content compred to the control smple, determined y HPLC, ws higher thn intended (38% vs. 30%). This difference etween the intended nd chieved level of enrichment could e cused y different mesuring pproches of spectrophotometric nd HPLC method (chromtogrphic seprtion nd sornce mesurement of single phenols in the cse of HPLC). The phenol composition of enriched olive pstes mlxed for 30, 45 nd 60 min is shown in Tle 1. Among identified phenolic compounds the most undnt (20% of the totl phenols mss frction) ws dildehydic form of decroxymethyloleuropein glycone (DMO-Agl-dA), proly product of β-glucosidse nd methylesterse ctivity on oleuropein during fruit crushing (El Richy et l., 2011; Romero-Segur et l., 2012). Gómez-Rico et l. (2009) hve reported tht the mjority of the oleuropein in olive fruits ws trnsformed in its derivtives only few minutes fter crushing, mong which DMO-Agl-dA ws predominnt. An ddition of the phenolic extrct to olive pste mostly ffected the mounts of dildehydic form of oleuropein glycone (O-Agl-dA) nd pigenin which incresed y 473% nd 90% in Buž pste, respectively. Also, in the enriched Buž olive pste (mlxtion time 0 min) sttisticlly significnt increse of DMO-Agl-dA, verscoside, luteolin nd luteolin-7-o-glucoside ws oserved. The increse of mlxtion time up to 60 min hs led to decrese of free hdroxytirosol, tirosol nd verscoside in enriched olive pste. The mss frction of flvonoids, such s luteolin-7-o-glucoside, luteolin nd pigenin ws slightly ffected y the mlxtion time, s lso reported Gómez-Rico et l. (2009) for olive pste of cultivr Cornicr. Also, slight decrese, ut not sttisticlly significnt, ws oserved for the totl phenols mss frction. Tle 1. Mss frction (mg/kg) of single phenolic compounds in Buž olive pstes enriched with phenol extrct (38%) during different mlxtion times. Phenolic compound Mlxtion time (min) (mg/kg) Control Tyr-OH c 839 ± ± ± ± 32 c 620 ± 42 c Tyr 214 ± ± ± ± ± 18 DMO-Agl-dA 1916 ± ± ± ± ± 270 iso-oleuropein 204 ± ± ± ± ± 10 O-Agl-dA 78 ± ± ± 26 cd 425 ± 16 c 383 ± 32 d verscoside 709 ± ± ± 26 cd 739 ± 25 d 802 ± 98 dc luteolin-7-o-glucoside 243 ± ± ± ± ± 42 luteolin 168 ± ± 9 c 228 ± ± 15 c 206 ± 20 c pigenin 4 ± 0 8 ± 0 c 8 ± 0 8 ± 1 c 7 ± 1 c totl unidentified d 5219 ± ± ± 547 c 7948 ± 440 c 7567 ± 436 c totl phenols 9595 ± ± ± ± ± 950 Results re mens of eight vlues (two independent repetitions of pste preprtion qudruplicte nlyses) ± SD; mens within ech row mrked with different letters re significntly different (Tukey s test, p<0.05). Control smple is Buž olive pste smple without ddition of phenols extrct, mlxed 0 min. c Full nmes in Arevitions. d Sum of the mss frction of ll peks of unidentified phenolic compounds on chromtogrm. An increse of phenols in Buž olive pste y 38% resulted in higher increse of the totl phenols in corresponding olive oils. A mss frction of the totl phenols in Buž olive oil otined from enriched pste mlxed for 30 min ws 82% higher thn the control smple which ws otined without phenol ddition (dt not shown). The composition of phenol compounds in enriched Buž olive oils mlxed for 30, 45 nd 60 min is shown in Tle 2. Oils otined from the enriched olive pste

4 mlxed 45 nd 60 min hd sttisticlly significnt lower mss frction of totl phenols thn oils with the mlxtion time 30 min. A negtive effect of longer mlxtion times on olive oil totl phenols is lso reported y Rnlli et l. (2003) nd Stefnoudki et l. (2011). During mlxtion phenolic compounds prtition etween oil nd wter depends on the composition nd reltive mounts of the phses nd reltive polrities of phenols (Rodis et l., 2002). A longer mlxtion time mostly negtively ffected mss frction of the most identified phenolic compounds in Buž oils. A sttisticlly significnt decrese of O-Agl-A, L-Agl-dA nd lignns ws determinted with prolonged mlxtion times. The reduction of the olive oil phenols during mlxtion could e due to interctions with polyscchrides present in olive pste (Servili, Montedoro, 2002) nd due to oxidtion y polyphenol oxidse nd peroxidse ctivity (Grcí-Rodríguez et l., 2011). Unlike the other phenolic compounds, vnillin incresed (y 31%) long with the mlxtion time. Tle 2. Mss frction (mg/kg) of single phenolic compounds in Buž VOOs otined from olive pste enriched with phenol extrct (38%) during different mlxtion times. Phenolic compound Mlxtion time (min) (mg/kg) Tyr-OH 10.7 ± ± ± 0,7 DMO-Agl-dA ± ± ± 11.3 O-Agl-dA 24.5 ± ± ± 2.0 O-Agl-A 62.9 ± ± ± 2.1 c Tyr 7.3 ± ± ± 0.2 DML-Agl-dA 57.3 ± ± ± 2.2 (DML-Agl-dA)ox 63.5 ± ± ± 2.4 L-Agl-dA 26.1 ± ± ± 0.8 c L-Agl-A 19.1 ± ± ± 0.8 luteolin 8.3 ± ± ± 0.9 methyl-luteolin 0.4 ± ± ± 0.0 pigenin 1.9 ± ± ± 0.1 vnillin 3.9 ± ± ± 0.7 vnillic+cffeic cid 2.2 ± ± ± 0.1 p-coumric cid 5.7 ± ± ± 0.3 lignns 31.8 ± ± ± 1.0 c totl unidentified c ± ± ± 9.6 totl phenols ± ± ± 29.8 Results re mens of eight vlues (two independent repetitions of pste preprtion qudruplicte nlyses) ± SD; mens within ech row mrked with different letters re significntly different (Tukey s test, p<0,05). Full nmes in Arevitions. c Sum of the mss frction of ll peks of unidentified phenolic compounds on chromtogrm. An ddition of phenolic compounds to olive pste cused sttisticlly significnt decrese of C6 ldehydes hexnl nd Z-3-hexenl, nd C6 lcohol E-2-hexen-1-ol (Figure 1). A reduction of these voltile compounds could e consequence of reduced ctivity of LOX, HPL nd ADH y phenols dded to olive pste (Sánchez-Ortiz et l., 2012; Sánchez-Ortiz et l., 2012). A reverse effect ws oserved on C6 ester Z-3-hexenyl cette nd C5 voltile compounds. It seems tht AAT, n enzyme responsile for the synthesis of voltile esters, ws unffected y dded phenols. An increse of ll C5 compounds could e due to the induced homolytic ctivity of lipoxygense y ccumultion of 13- hydroperoxides in enriched Buž pste. Vncnneyet et l. (2001) suggested LOX involvement in hydroperoxide clevge sed on higher levels of C5 compounds in the leves of HPL-deficient trnsgenic potto plnts. These results suggest tht some enzymes in the LOX pthwy might e prtilly dectivted y dded phenols. A slight decrese of mss frction of the most voltile compounds cn e oserved long with the mlxtion time (Figure 1). Among these voltile compounds responsile for positive odour notes, the mlxtion time hd significnt negtive effect on hexnl, hexn-1-ol nd Z-3-hexenyl cette. Mss frctions of these voltiles were reduced y 12, 28 nd 38%, respectively, in oil smples mlxed 60 min compred to 30 min.

5 Mss frction (mg/kg) in oil Mss frction (mg/kg) in oil 6,0 5,0 4,0 3,0 2,0 1,0 0,0 0,10 0,09 0,08 0,07 0,06 0,05 0,04 0,03 0,02 0,01 0,00 control smple 30 min 45 min 60 min c hexnl E-2-hexenl Z-3-hexenl E-3-hexen-1-ol E-2-hexen-1-ol hexn-1-ol Z-3-hexenyl cette c c hexyl cette A decrese of C6 esters y the mlxtion time, especilly of Z-3-hexenyl cette, ws reported y Angeros et l. (2001) nd Rnlli et l. (2003) nd could e due to inctivtion of AAT during mlxtion. A slight positive effect of mlxtion time, ut not sttisticlly significnt, ws oserved for C5 voltile compounds wht is in ccordnce with results of Angeros et l., Minor chnges of totl nd single voltile compounds indicte tht voltile compounds re influenced more y phenol enrichment of olive pste thn y the mlxtion time. CONCLUSION Phenol enrichment of olive pste cused decrese of C6 ldehydes nd C6 lcohols in VOO, while C6 esters nd C5 compounds incresed. Longer mlxtion time (60 min) of olive pste showed more pronounced effect on phenols thn on voltile compounds. Mss frction (mg/kg) in oil 0,50 0,45 0,40 0,35 0,30 0,25 0,20 0,15 0,10 0,05 0,00 c pentnl E-2-pentenl Z-2-penten-1- ol 1-penten-3-ol 1-penten-3- one Figure 1. Mss frction (mg/kg) of voltile compounds in Buž VOO smples otined from olive pstes enriched with phenol extrct during different mlxtion times. Control smple is Buž VOO smple otined from pste without ddition of phenols extrct, mlxed 45 min. Results re mens of four vlues (two independent repetitions of oil preprtion duplicte nlyses) ± SD. Mens within ech voltile compound, mrked with different letters, re significntly different (Tukey s test, p < 0,05). Arevitions: Tyr-OH - hidroxytirosol; Tyr - tyrosol; DMO-Agl-dA - dildehydic form of decroxymethyloleuropein glycone; O-AgldA = dildehydic form of oleuropein glycone; O-Agl-A = ldehydic form of oleuropein glycone; DML-Agl-dA = dildehydic form of decroxymethylligstroside glycone; (DML- Agl-dA)ox = oxidized form of DML-Agl-dA; L-Agl-dA = dildehydic form of ligstroside glycone; L-Agl-A = ldehydic form of ligstroside glycone. Funding nd Acknowledgments These results re derived from the scientific project Bioctive nd voltile compounds of VOO in processing nd finishing ( ) supported y Ministry of Science, Eduction nd Sports of Repulic of Croti. Ph.D student V.M.G. hs een prtilly supported y n Alpe-Adri Reserch Grnt from the University of Udine nd Bilterl Moility Grnt from the Ministry of the Repulic of Sloveni for Higher Eduction, Science nd Sport. Authors re grteful to V. Vlenčič nd M. Mreg for technicl ssistnce nd to E. Bellé nd M. Vošten for olive fruits dontion. REFERENCES 1. Angeros F., Mostllino R., Bsti C., Vito R Virgin olive oil odour notes: Their reltionships with the voltile compound from the lipoxygense pthwy nd secoiridoid compounds. Food Chemistry 68,

6 2. Angeros F., Mostllino R., Bsti C., Vito R Influence of mlxtion temperture nd time on the qulity of virgin olive oils. Food Chemistry 72, Brkić Buol K., Koprivnjk O., Sldonj B., Lukić I Voltile compounds nd sensory profiles of monovrietl virgin olive oil from Buž, Črn nd Rosinjol cultivrs in Istri (Croti). Food Technology nd Biotechnology 50, Clodoveo M. L Mlxtion: Influence on virgin olive oil qulity. Pst, present nd future-n overview. Trends in Food Science nd Technology 25(1), El Richy M., Priego-Cpote F., León L., Rllo L., Luque de Cstro M. D Hydrophilic ntioxidnts of virgin olive oil. Prt 2: Biosynthesis nd iotrnsformtion of phenolic compounds in virgin olive oil s ffected y gronomic nd processing fctors. Europen Journl of Lipid Science nd Technology 113, Grcí-Rodríguez R., Romero-Segur C., Snz C., Sánchez-Ortiz A., Pérez A. G Role of polyphenol oxidse nd peroxidse in shping the phenolic profile of virgen olive oil. Food Reserch Interntionl 44(2), Gómez-Rico A., Inrejos-Grcí A. M., Desmprdos Slvdor M., Fregpne G Effect of mlxtion conditions on phenol nd voltile profiles in olive pste nd the corresponding virgin olive oils (Ole europe L. cv. Cornicr). Journl of Agriculturl nd Food Chemistry 57, Inrejos-Grcí A. M., Fregpne G., Desmprdos Slvdor M Effect of crushing on olive pste nd virgin olive oil minor components. Europen Food Reserch nd Technology 232, Interntionl Olive Council Determintion of iophenols in olive oils y HPLC. COI/T.20/Doc No Mjetić Germek V., Koprivnjk O., Butinr B., Pizzle L., Bučr-Miklvčič M., Conte S. L Influence of phenols mss frction in olive (Ole europe L.) pste on voltile compounds in Buž cultivr virgin olive oil. Journl of Agriculturl nd Food Chemistry 61, Olís J. M., Pérez A.G., Rios J. J., Snz L. C Arom of virgin olive oil: Biogenesis of the green odor notes. Journl of Agriculturl nd Food Chemistry (12), Rnlli A., Pollstri L., Contento S., Innucci E., Lucer L Effect of olive pste kneding process time on the overll qulity of virgin olive oil. Europen Journl of Lipid Science nd Technology 105, Rodis P. S., Krthnos V. J., Mntzvinou A Prtitioning of olive oil ntioxidnts etween oil nd wter phses. Journl of Agriculturl nd Food Chemistry 50, Romero-Segur C., Grcí-Rodríguez R., Sánchez-Ortiz A., Snz C., Pérez, A. G The role of olive β- glucosidse in shping the phenolic profile of virgin olive oil. Food Reserch Interntionl 45, Servili M., Montedoro GF Contriution of phenolic compounds to virgin olive oil qulity. Europen Journl of Lipid Science nd Technology 104, Sánchez-Ortiz A., Romero-Segur C., Gzd V. E., Grhm I. A., Snz C., Pérez A. G Fctors limiting the synthesis of virgin olive oil voltile esters. Journl of Agriculturl nd Food Chemistry 60, Sánchez-Ortiz A., Romero-Segur C., Snz C., Pérez A. G Synthesis of voltile compounds of virgin olive oil is limited y the lipoxygense ctivity lod during the oil extrction process. Journl of Agriculturl nd Food Chemistry 60, Stefnoudki E., Koutsftkis A., Hrwood J. L Influence of mlxtion conditions on chrcteristic qulities of olive oil. Food Chemistry 127, Škevin D., Rde D., Štrucelj D., Mokrovčk Ž., Neñerl S., Benčić, ð The influence of vriety nd hrvest time on the itterness nd phenolic compounds of olive oil. Europen Journl of Lipid Science nd Technology 105, Vlenčič V., Bndelj Mvsr D., Bučr-Miklvčič M., Butinr B., Čdež N., Golo T., Rspor P., Smole Možin S The impct of production technology on the growth of indigenous microflor nd qulity of tle olives from Slovenin Istri. Food Technology nd Biotechnolgy 48(3), Vncnneyt G., Snz C., Frmki T., Pneque M., Ortego F.,Cstñer P., Sánchez-Serrno J. J Hydroperoxide lyse depletion in trnsgenic potto plnts leds to n increse in phid performnce. Proceedings of the Ntionl Acdemy of Sciences of the United Sttes of Americ 98, Vichi S., Cstellote A. I., Pizzle L., Conte L. S., Buxders S., López-Tmmes E Anlysis of virgin olive oil voltile compounds y hedspce solid-phse microextrction coupled to gs chromtogrphy with mss spectrometric nd flme ioniztion detection. Journl of Chromtogrphy A 983,

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