An Optimised Aqueous Extract of Phenolic Compounds from Bitter Melon with High Antioxidant Capacity

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1 Antioxidnts 2014, 3, ; doi:10.33/ntiox Artile OPEN ACCESS ntioxidnts ISSN An Optimised Aqueous Extrt of Phenoli Compounds from Bitter Melon with High Antioxidnt Cpity Sing Pei Tn 1, *, Costs Stthopoulos 2, Sophie Prks 1,3 nd Pul Roh 1 1 Shool of Environmentl nd Life Sienes, University of Newstle, Ourimh, NSW 2258, Austrli; E-Mils: sophie.prks@dpi.nsw.gov.u (S.P.); pul.roh@newstle.edu.u (P.R.) 2 Fulty of Biosiene Engineering, Ghent University Glol Cmpus, Inheon , Kore; E-Mil: osts.stthopoulos@ghent..kr 3 Centrl Cost Primry Industries Centre, NSW Deprtment of Primry Industries, Ourimh, NSW 2258, Austrli * Author to whom orrespondene should e ddressed; E-Mil: sing.p.tn@uon.edu.u; Tel.: ; Fx: Externl Editors: Antonio Segur-Crretero nd Dvid Arráez-Román Reeived: 9 Septemer 2014; in revised form: 13 Novemer 2014 / Aepted: 14 Novemer 2014 / Pulished: 2 Deemer 2014 Astrt: Bitter melon (Momordi hrnti L.) is tropil fruit limed to hve mediinl properties ssoited with its ontent of phenoli ompounds (TPC). The im of the study ws to ompre wter with severl orgni solvents (etone, utnol, methnol nd % ethnol) for its effiieny t extrting the TPC from freeze-dried itter melon powder. The TPC of the extrts ws mesured using the Folin-Ciolteu regent nd their ntioxidnt pity (AC) ws evluted using three ssys. Before optimistion, the TPC nd AC of the queous extrt were 63% nd 20% lower, respetively, thn for the est orgni solvent, % ethnol. However, fter optimising for temperture ( C), time (5 min), wter-to-powder rtio (40:1 ml/g), prtile size (1 mm) nd the numer of extrtions of the sme smple (1 ), the TPC nd the AC of the queous extrt were equl or higher thn for % ethnol. Furthermore, less solvent (40 ml wter/g) nd less time (5 min) were needed thn ws used for the % ethnol extrt ( ml/g for 1 h). Therefore, this study provides evidene to reommend the use of wter s the solvent of hoie for the extrtion of the phenoli ompounds nd their ssoited ntioxidnt tivities from itter melon.

2 Antioxidnts 2014, Keywords: itter melon; phenoli ompounds; ntioxidnt pity; queous extrtion; orgni solvents 1. Introdution Bitter melon (Momordi hrnti L.) is populr mediinl fruit prtiulrly in Asi nd Afri, where mny vrieties re grown. For exmple, itter melon hs een ssoited with nti-ner [1], nti-miroil [2], nti-inflmmtory [3] nd nti-dieti properties [4]. The potentil mediinl vlues of the fruit hve een linked to its ontent of phenolis nd their ntioxidnt properties [4 7]. The phenoli struture is omprised of n romti group with one or more hydroxyl groups [8]. Owing to the hydroxyl groups, most phenolis in itter melon re hydrophili ompounds, suh s glli id, gentisi id, tehin, hlorogeni id, epitehin, vnillin id, prototehui id, p-oumri id, o-oumri id, nd t-innmi id [9,10]. Studies hve reported tht phenolis hve potent ntioxidnt nd free rdil-svenging tivities [11,12]. Whole itter melon (flesh, ril nd seeds) hs een shown to e good soure of phenoli ompounds [9] nd one study demonstrted tht the flesh, ril nd seeds ll hd very high ntioxidnt tivity [9]. Another study suggested tht the ntioxidnt nd free rdil svenging properties in the extrts of itter melon ould e ttriuted to flvonoids nd other phenoli ompounds [11]. The results lso reveled tht, on weight per weight sis, the itter melon hd etter 2,2-diphenyl-1-pirylhydrzyl (DPPH) rdil svenging nd ferri reduing ntioxidnt power (FRAP) thn vitmin E [11]. The phenoli ompounds extrted from plnt mtries nd their ssoited ntioxidnt tivities re dependent on the prmeters of the method used, inluding the solvent type nd polrity, the temperture, the length of the extrtion, the numer of times smple is extrted, nd on the ondition of the rw mteril, inluding its prtile size [13,14]. To dte, severl solvents, inluding methnol [15], wter [12] nd the omintion of ethnol nd wter [10], hve een used for extrting phenoli ompounds from itter melon. Although studies hve reported tht orgni solvents n e more effetive thn wter t extrting phenoli ompounds from plnt mterils [16,17], wter is more desirle extrtnt for the food industry euse it is non-toxi, environmentlly friendly nd inexpensive ompred to orgni solvents [18]. To our knowledge, no pulished study hs omprehensively investigted nd optimised the queous extrtion of phenoli ompounds nd their ssoited ntioxidnt tivities from itter melon nd ompred the optimised queous extrtion of these ompounds with tht hieved with orgni solvents. Therefore, this study imed to mximise the queous extrtion of the phenoli ompounds from freeze-dried nd powdered itter melon nd to ompre the optimised queous extrt with tht otined with the est orgni solvent from methnol, % ethnol, utnol nd etone. The onditions investigted for the queous extrtion of the phenoli ompounds from the powdered itter melon were temperture, time, wter-to-powder rtio, powder prtile size nd the numer of extrtions of the sme smple. The optimised queous extrt ws then ompred to the est of the orgni solvent extrt in terms of totl phenoli ontent (TPC) nd ntioxidnt pity (AC). The orreltion etween the TPC nd the AC of the extrts ws lso determined.

3 Antioxidnts 2014, Mterils nd Methods 2.1. Plnt Mteril Bitter melon (Moonlight vriety) fruits (20 kg), grown in the Northern Territory (Drwin, NT, Austrli), were purhsed from the Sydney mrkets (Sydney, NSW, Austrli) nd frozen t 20 C until used. The frozen itter melons were ut into slies (~1 to 2 mm) nd pled in liquid nitrogen efore drying in FD3 freeze dryer (Rietshle Thoms, Seven Hills, NSW, Austrli) t 40 C for 72 h t mr. After freeze-drying, smples were ground into powder using ommeril lender (John Morris Sientifi, Chtswood, NSW, Austrli). The powders were mixed thoroughly nd sorted into six prtile sizes (<0.25, , 1 0.5, 1 2, nd >2.8 mm) y sieving through series of EFL 2000 stinless steel sieves (Endeotts Limited, London, Englnd). The powders were then kept in seled ontiners t 20 C until used Chemils Methnol nd etone were otined from Merk (Kilsyth, VIC, Austrli). Ethnol ws purhsed from Fronine (Tren Point, NSW, Austrli). Hydrohlori id (36%) ws otined from Ajx Finehem (North Ryde, NSW, Austrli) nd n-utnol ws purhsed from Swift Austrli Chemil Supplier (Mulgrve, VIC, Austrli). Folin-Ciolteu (FC) regent, 2,2 -zinois-(3-ethylenzothiozoline-6-sulfoni id (ABTS), 2,2 -diphenyl-1-pirylhydrzyl (DPPH), sodium ronte, sodium nitrite, luminium hloride, sodium hydroxide, vnillin, sodium ette trihydrte, eti id, 2,4,6-tripyridyl-s-trizine (TPTZ), ferri (III) hloride hexhydrte, sulphuri id nd stndrds (trolox, glli id, rutin nd esin) were purhsed from Sigm-Aldrih (Cstle Hill, NSW, Austrli) Initil Solvent Extrtions The overll experimentl design for the study is illustrted in Figure 1. Initilly, extrtions were done with five solvents: etone, n-utnol, % ethnol ( ethnol/20 wter, v/v), methnol nd deionised wter. Bitter melon extrts were prepred y dding 1 g of freeze-dried itter melon powder to ml of solvent nd extrting for 1 h using shking wter th (Rtek Instruments, Boroni, VIC, Austrli). The extrtion tempertures were set elow the oiling point of eh solvent: C for etone, C for methnol nd C for n-utnol, % ethnol nd deionised wter. After extrtion, the smples were llowed to ool nd settle on ie for 10 min. The extrts were then entrifuged t 43 g for 10 min t 10 C (Bekmn Instruments In., Plo Alto, CA, USA) nd the superntnt from eh smple ws filtered through 0.45 μm syringe filter (Phenomenex, Pennnts Hills, NSW, Austrli) prior to nlysis. All extrtions were onduted in triplite.

4 Antioxidnts 2014, Figure 1. Digrm for the experimentl design. Initilly, the totl phenoli ontent (TPC) nd ntioxidnt pity (AC) of the extrts of freeze-dried itter melon powder otined with five different solvents, inluding wter, were ompred. The queous extrtion onditions were then optimised in terms of TPC nd AC nd ompred to the % ethnol extrt, whih hd the highest vlues in the initil solvent sreening experiment. Bitter melon Freeze-drying nd grinding into powder Extrtion using five solvents (etone, n-utnol, % ethnol, methnol nd wter) * Aqueous extrtion onditions optimised sed on five prmeters: temperture, time, wter-to-powder rtio, prtile size nd numer of extrtions *All vlues were ompred with the est solvent (% ethnol) Optiml queous extrtion onditions for TPC nd AC 2.4. Optimising the Aqueous Extrtion The queous extrtion ws then optimised y testing, in sequentil order, rnge of tempertures, times, wter-to-powder rtios, prtile sizes nd the numer of times the sme smple ws extrted. To determine the effet of the extrtion temperture on the queous extrtion of phenoli ompounds, 1 g of freeze-dried itter melon powder ws extrted with ml of deionised wter t 5 C nd t intervls of 10 from 10 to C for 1 h using the shking wter th. The optiml tempertures for extrtion (40 nd C) were then used to determine the effet of the extrtion time; 1 g of freeze-dried itter melon powder ws extrted with ml of deionised wter t 40 nd C for 5, 10, 15, 20, 25, 30, 40, nd min. The optiml omintion of time (5 min) nd temperture ( C) ws then used to determine the effet of the wter-to-powder rtio; 1 g of freeze-dried powder ws extrted in 10, 20, 25, 30, 40, nd ml of deionised wter. To determine the effet of the freeze-dried prtile size, the optimum onditions for temperture ( C), time (5 min) nd wter-to-powder rtio (40:1 ml/g) were used to extrt 2.5 g of ground freeze-dried itter melon hving vrious sizes (<0.25, , , , nd >2.8 mm in dimeter) with ml of deionised wter. Finlly, to evlute the effet of extrting the sme smple severl times, 2.5 g of ground freeze-dried powder (1 mm) ws extrted one, two or three times with ml of deionised wter t C for 5 min.

5 Antioxidnts 2014, After eh of the queous extrtion experiments, the smples were llowed to ool on ie for 10 min efore they were entrifuged nd their superntnt ws filtered through 0.45 μm syringe filter (Phenomenex, Pennnts Hills, NSW, Austrli) prior to nlysis.. All experiments were onduted in triplite Extrtion Effiieny From the initil extrtions done with the five solvents (etone, n-utnol, % ethnol, methnol nd deionised wter), it ws found tht the % ethnol extrt hd the highest TPC nd AC. Therefore, the % ethnol extrt ws hosen s the ontrol extrt for ompring the extrtion effiieny for the vrious queous extrtions in terms of TPC nd ntioxidnt pity. The extrtion effiieny for the queous extrtions, with respet to their TPC nd AC, ws lulted nd expressed s perentge of the % ethnol (EtOH) extrt s follows: Extrtion effiieny % = (TPC or AC for queous extrt/tpc or AC for EtOH extrt) Totl Phenoli Content The TPC of smples ws determined ording to [19] with some modifitions. Briefly, 300 μl of ppropritely diluted itter melon extrt or stndrd solution (pproprite for eh of the five extrting solvents, inluding lnk) ws mixed nd inuted with 300 μl of FC solution for 2 min efore 2400 μl of g/l sodium ronte solution ws dded. The solutions were mixed well nd pled in the drk t room temperture for 2 h efore the sorption ws mesured t 765 nm using spetrophotometer (Crry Bio, Vrin Pty. Ltd., Mulgrve, VIC, Austrli). Glli id ws used s the stndrd nd the TPC ws expressed s mg glli id equivlents (GAE) per g of dry powder weight (mg GAE/g) ABTS Assy The ABTS ssy ws onduted ording Re et l. [20] with some modifitions. Stok solutions of 7.4 mmol/l ABTS nd 2.6 mmol/l potssium persulfte in deionised wter were prepred nd kept t 4 C until used. Fresh working solution ws prepred for eh ssy y mixing the two stok solutions in equl quntities nd inuting for h in the drk t room temperture. Then, 1 ml of the working solution ws mixed with ml methnol to otin n sorne of 1.1 ± 0.02 units t 734 nm. Eh ppropritely diluted itter melon extrt nd stndrd solution (1 μl) ws mixed nd inuted with 28 μl of the working solution for 2 h in the drk t room temperture efore the sorption ws mesured t 734 nm. Trolox ws used s stndrd nd the AC ws expressed s μmol of trolox equivlents (TE) per g of dry powder weight (μmol TE/g) DPPH Assy The DPPH ssy ws onduted ording to Brnd-Willims et l. [21] with some modifitions. In rief, stok solution of 0.6 mol/l DPPH in methnol ws prepred nd kept t 20 C until used. Fresh working solution ws prepred for eh ssy y mixing 10 ml of stok solution with 45 ml of methnol to otin n sorne of 1.1 ± 0.02 units t 515 nm. Eh ppropritely diluted itter melon extrt nd stndrd solution (1 μl) ws mixed nd inuted with 28 μl of working solution for 30 min

6 Antioxidnts 2014, t room temperture efore the sorption ws mesured t 515 nm. Trolox ws used s stndrd nd the AC ws expressed s μmol trolox equivlents (TE) per g of dry powder weight (μmol TE/g) FRAP Assy The FRAP ssy ws onduted ording to Benzie nd Strin [22] with some modifitions. The stok solutions of 300 mmol/l ette uffer ph 3.6, 10 mmol/l TPTZ in 40 mmol/l HCl nd 20 mmol/l ferri (III) hloride hexhydrte were prepred nd kept t 4 C until used. Fresh working solution ws prepred for eh ssy y mixing ml of ette uffer, 10 ml of TPTZ nd 10 ml of ferri (III) hloride hexhydrte in rtio of 10:1:1 nd inuted t 37 C efore it ws used. Eh ppropritely diluted itter melon extrt nd stndrd solution (1 μl) ws mixed nd inuted with 28 μl of the working solution for 30 min in the drk t room temperture efore the sorption ws mesured t 593 nm. Trolox ws used s stndrd nd AC ws expressed s μmol trolox equivlents (TE) per g of dry powder weight (μmol TE/g) Sttistil Anlysis The Sttistil Pkge for Soil Siene (SPSS) Version 19 (IBM Austrli Limited, St Leonrds, NSW, Austrli) ws used for dt nlyses. All experiments were onduted in triplite nd the one-wy ANOVA nd the Bonferroni post-ho test were used to determine ny signifint differenes etween the men vlues for the different tretments within n experiment. The Person orreltion test ws performed to estlish the signifine of orreltions etween the TPC nd AC. 3. Results 3.1. Initil Solvent Extrtions Initilly, the freeze-dried itter melon powder ws extrted with five solvents: etone, n-utnol, % ethnol, methnol nd deionised wter. The % ethnol extrt hd the highest TPC (Figure 2) nd the highest AC in ll three ntioxidnt ssys (Figure 3). The methnol extrt lso exhiited the highest TPC (Figure 2) nd the highest AC in the DPPH nd FRAP ntioxidnt ssys ut hd signifintly lower AC thn the % ethnol extrt in the ABTS ssy (Figure 3). The extrtion of phenoli ompounds y wter ws signifintly less effetive thn for % ethnol nd methnol ut ws out three times more effetive thn for utnol nd etone. The AC for the queous extrt ws lso muh higher thn for the utnol nd etone extrts in ll three ntioxidnt ssys (Figure 3). There ws no signifint differene etween the ABTS vlues for the queous nd the methnol extrts ut the AC for the queous extrt ws lower thn for the % ethnol extrt (Figure 3). In the DPPH nd FRAP ssys, the queous extrt hd signifintly lower AC thn oth the methnol nd % ethnol extrts (Figure 3). Overll, strong orreltions were oserved etween the TPC of the vrious solvent extrts (Figure 2) nd their AC (Figure 3) s mesured with the three ssys: ABTS (R = 0.94), DPPH (R = 0.95) nd FRAP (R = 0.99).

7 Trolox equivlents (µmol/g) Glli id equivlents (mg/g) Antioxidnts 2014, Figure 2. Totl phenoli ontent of itter melon extrts otined with five solvents. Vlues re mens ± stndrd devitions (n = 3) nd those not shring supersript letter re signifintly different (p < 0.05) from eh other Figure 3. The 2,2 -zinois-(3-ethylenzothiozoline-6-sulfoni id (ABTS), 2,2 -diphenyl-1- pirylhydrzyl (DPPH) nd ferri reduing ntioxidnt power (FRAP) ssys were used to determine the ntioxidnt pity. Vlues re mens ± stndrd devitions (n = 3) nd those not shring supersript letter re signifintly different (p < 0.05) from eh other. 120 d Butnol Aetone Methnol %Ethnol Wter d ABTS DPPH FRAP 3.2. Optimising the Aqueous Extrtion The optiml onditions for the queous extrtion of the itter melon phenoli ompounds nd their ntioxidnt tivities were then determined y testing, in sequentil order, rnge of tempertures, times, wter-to-powder rtios, prtile sizes nd the numer of times the sme smple ws extrted. The results,

8 Extrtion Effiieny (%) Extrtion Effiieny (%) Extrtion Effiieny (%) Extrtion Effiieny (%) Antioxidnts 2014, expressed s extrtion effiieny reltive to the % ethnol extrt, for TPC re presented in Figure 4 nd those for AC in Figure 5. Figure 4. The extrtion effiieny for phenoli ompounds from itter melon using wter. The queous extrtion ws optimised using one-vrile-t--time method nd eh vrile ws tested in sequentil order: (A) temperture; (B) time; (C) wter-to-powder rtio; (D) powder prtile size nd (E) numer of times the sme smple is extrted. The powder prtile size tegories were: (1) <0.25, (2) , (3) , (4) , (5) nd (6) >2.8 mm. The extrtion effiieny ws reltive to the % ethnol extrt nd dt re mens ± stndrd devitions (n = 3) nd those not shring letter re signifintly different (p < 0.05) from eh other. * This vlue is lso signifintly different (p < 0.05) from the vlues otined t 40 C (A) de d de d e d Temperture ( C) (C) Wter/Powder (ml/g) (B) * 40 d de e e Time (min) (D) Powder Prtile Size Ctegories

9 Extrtion Effiieny (%) Antioxidnts 2014, Figure 4. Cont. (E) 110 1x 2x 3x Numer of Extrtions The extrtion effiieny for TPC ws highest t tempertures etween 20 nd C nd t C (Figure 4A). Therefore, the extrtion time experiment ws done t two tempertures, 40 nd C, whih showed tht C for 5 min ws the optiml omintion of temperture nd time (Figure 4B). Notly, the extrtion effiieny for TPC otined for 5 min t C ws higher thn the highest effiieny t 40 C, whih ws otined t 10 min (Figure 4B). Importntly, only 5 min ws needed for the extrtion, whih is muh shorter time thn the 1 h usully used for orgni solvent extrtions. Using C for 5 min, it ws then found tht vlues etween 25 nd ml/g for the wter-to-powder rtio gve the highest extrtion effiieny for TPC (Figure 4C). From these results, wter-to-powder rtio of 40 ml/g ws hosen s eing in the optiml rnge. Therefore, less wter ws needed thn ml/g, whih is usully used for orgni solvent extrtions. The extrtion onditions of C for 5 min nd wter-to-powder rtio of 40 ml/g were then used for testing the effet of powder prtile size. As seen in Figure 4D, the extrtion effiieny for TPC ws higher t powder prtile sizes 2.0 mm in dimeter ompred to sizes 2.0 mm. Therefore, powder prtile size of 1.0 mm ws hosen s eing in the optiml rnge. Finlly, the numer of times the sme powder sme is extrted ws tested using powder prtile dimeter size of 1.0 mm with wter-to-powder rtio of 40 ml/g t C for 5 min. There ws no signifint differene in the extrtion effiieny for TPC whether smple for extrted one, twie or thrie (Figure 4E) nd thus, single step ws onsidered optiml. Similrly, for the AC of the queous extrts, the highest extrtion effiieny ws oserved t C for the DPPH nd FRAP ssys (Figure 5A) while the extrtion temperture hd less of n effet on the AC mesured using the ABTS ssy. Therefore, these results supported the hoie of C s the optiml temperture. Furthermore, doing the queous extrtion t C for 5 min lso gve optiml AC vlues (Figure 5B). Susequently, wter-to-powder rtio of 40 ml/g (Figure 5C), powder prtile dimeter size of 1.0 mm (Figure 5D) nd one extrtion (Figure 5D) proved to e optiml for the queous extrtion done t C for 5 min, in terms of AC mesured y the three ntioxidnt ssys, the sme optiml onditions s for TPC (Figure 4).

10 Extrtion Effiieny (%) Extrtion Effiieny (%) Extrtion Effiieny (%) Extrtion Effiieny (%) Antioxidnts 2014, Figure 5. The extrtion effiieny for ntioxidnt pity from itter melon using wter. The queous extrtion ws optimised using one-vrile-t--time method nd eh vrile ws tested in sequentil order: (A) temperture; (B) time; (C) wter-to-powder rtio; (D) powder prtile size nd (E) numer of times the sme smple is extrted. The powder prtile size tegories were: (1) <0.25, (2) , (3) , (4) , (5) nd (6) >2.8 mm. The extrtion effiieny ws reltive to the % ethnol extrt nd dt re mens ± stndrd devitions (n = 3) nd those not shring letter re signifintly different (p < 0.05) from eh other (A) d d ABTS DPPH FRAP Temperture ( C) e (B) d d d de ABTS DPPH FRAP Time (min) e e f f f d f (C) (D) Wter/Powder (ml/g) ABTS DPPH FRAP Powder Prtile Size Ctegories ABTS DPPH FRAP

11 Extrtion Effiieny (%) Antioxidnts 2014, Figure 5. Cont (E) ABTS DPPH FRAP 1x 2x 3x As seen in Tle 1, the TPC nd the AC of the queous extrt were sustntilly improved under the optimised onditions ompred to the vlues shown in Figures 2 nd 3, respetively. Importntly, this ment tht the TPC nd the AC (mesured with the ABTS ssy) of the optimised queous extrt were lso the sme s for the % ethnol extrt (Tle 1). Furthermore, the AC of the queous extrt ws 20% nd 10% higher for the DPPH nd FRAP ssys, respetively, ompred to the % ethnol extrt (Tle 1). Tle 1. The phenoli ompound ontent (TPC) nd the ntioxidnt pity of the optimised queous extrt of itter melon ompred with the % ethnol extrt. Chemil Properties Aqueous Extrt % Ethnol Extrt TPC (mg GAE/g dry sis) 10.6 ± ± 0.3 ABTS (μmol TE/g dry sis) 94.8 ± ± 3.5 DPPH (μmol TE/g dry sis) 58.6 ± ± 4.0 FRAP (μmol TE/g dry sis) 91.9 ± ± 4.3 Vlues re mens ± stndrd devitions (n = 3) nd those in row not shring supersript letter re signifintly different from eh other (p < 0.05). Finlly, the TPC of the vrious queous extrts ws shown to hve high ssoition with AC mesured with the three ntioxidnt ssys (Tle 2). However, the ssoition with TPC ws 10% nd 15% lower for the AC mesured with the ABTS nd the DPPH ssys, respetively, ompred to with the FRAP ssy. This ws despite the AC eing highly orrelted etween the three ssys ( 0.). Tle 2. Person orreltion oeffiients (R) for the totl phenoli ontent (TPC) of queous extrts nd their totl ntioxidnt pity mesured with the three ssys. Correltion ABTS DPPH FRAP TPC ** ** ** FRAP ** ** DPPH 0.1 ** ** All orreltions were signifint t p < 0.01 (n = 132).

12 Antioxidnts 2014, Disussion This study demonstrted tht the queous extrtion of phenoli ompounds from itter melon ws s effiient s orgni solvent extrtions, when the extrtion onditions were optimised. In the present study, efore optimistion, % ethnol ws shown to e the most suitle solvent for extrting phenolis nd their ssoited AC from itter melon (Figures 2 nd 3). This finding is onsistent with the study on phenolis nd ntioxidnt tivity of itter melon y Horx et l. (2010), whih demonstrted tht mixture of ethnol/20 wter (v/v) ws the optiml ethnol: wter solvent [10]. The TPC of the queous extrt ws 63% lower thn for the est orgni solvent, % ethnol (Figure 2), nd the AC ws t lest 20% lower (Figure 3). However, fter optimistion, the TPC nd the AC of the queous extrt were equl or higher thn for % ethnol (Tle 1). Furthermore, less solvent (40 ml wter/g) nd less time (5 min) were needed thn ws used for the % ethnol extrt ( ml/g for 1 h). In generl, low tempertures (5 nd 10 C ) redued the extrtion of phenoli ompounds from itter melon wheres higher tempertures (20 C) improved the extrtion (Figures 4A nd 5A). Inresing the temperture of wter is known to derese its visosity, whih n inrese the diffusion oeffiients of solutes, inluding wter solule phenoli ompounds, nd therey inrese the extrtion effiieny of the phenoli ompounds from the itter melon y the queous solvent [23]. Furthermore, heting llows the ell wll of plnt mterils to e more permele, therey llowing the solvent nd the solutes, from inside the plnt ell wlls, to diffuse in nd out of the plnt ells more esily [18,24]. However, tempertures ove C lowered the extrtion effiieny; this my hve refleted degrdtion of the phenoli ompounds, whih n our t these high tempertures [25]. The length of the extrtion t C lso hd signifint impt (Figures 4B nd 5B); interestingly, only 5 min ws needed to reh the mximum for the extrtion. This result indites tht the phenoli ompounds in itter melon my e highly solule in wter t C [26]. They re firly polr ompounds euse, the polr orgni solvents, % ethnol nd methnol, were lso more effiious t extrting the phenoli ompounds from itter melon ompred to the less polr solvents, etone nd utnol (Figure 2). Phenoli ompounds hve lso een extrted from itter melon in previous studies using polr solvents, inluding wter [10,12]. Doing more thn one extrtion of the sme smple lso did not improve the extrtion of the phenoli ompounds or the ntioxidnt tivity of the queous extrt (Figures 4E nd 5E). This supports the suggestion tht the predominnt phenoli ompounds in itter melon re very hydrophili; they were very effiiently extrted within 5 min during the first extrtion. Other studies hve lso reported tht the phenoli ompounds were suessfully extrted from itter melon using wter [11,12]. Although less likely, exposure of the phenoli ompounds to tempertures higher thn C (Figures 4A nd 5A) nd for longer thn 5 min t C (Figures 4B nd 5B) my hve led to their degrdtion [25]. In the present study, gret re ws tken to redue the length of time the extrts were exposed to the extrtion temperture eing tested; ll smples were pled on ie immeditely fter the intended extrtion time nd llowed to ool down for 10 min. This is importnt euse it hs previously een noted tht phenoli ompounds in hot wter extrts n sustntilly degrde when the extrts re left to ool down t room temperture [27]. The present finding on the length of the queous extrtion re in greement with study on penut skins [28] nd on ppy leves [29]. In ontrst, the extrtion effiieny for TPC nd AC of olive

13 Antioxidnts 2014, seeds [30] nd pomegrnte leves [31] extrts inresed with longer extrtion times. This suggests tht the type of phenoli ompounds in itter melon re likely to e more like those in penut skins nd ppy leves thn in olive seeds nd pomegrnte leves. Inresing the wter-to-powder rtio resulted in higher extrtion of the phenoli ompounds (Figures 4C nd 5C), whih ws onsistent with the extrtion of wter solule omponents from plnt mteril in generl [32]. This is due to the high osmoti pressure, whih results from the steep onentrtion grdient of the omponents in the plnt mteril vs. the solvent tht is generted t the high wter-to-powder rtios [32]. The urrent finding ws lso in greement with the results of studies on the extrtion of other solutes from plnt mterils [33,34]. The powder prtile sizes 2 mm, lso resulted in higher extrtion effiienies thn the powder sizes 2 mm (Figures 4D nd 5D). This ws onsistent with previous studies, whih hve shown tht smller powder prtile size results in higher extrtion effiieny of iotive ompounds from powdered pln mteril euse the surfe re of the powder in ontt with the solvent is inresed [18]. Furthermore, the diffusion distne within the powder prtile is shorter nd the onentrtion grdient is steeper etween the plnt mteril nd the solvent, resulting in higher extrtion effiieny [35]. Finlly, the TPC of the vrious queous extrts ws highly orrelted with the AC of the extrts s mesured with the FRAP, DPPH nd ABTS ssys (Tle 2). Similrly high orreltions (R 0.94) were lso oserved etween the TPC nd the AC of the extrts in the originl experiment with the five different solvents (Figures 2 nd 3). These findings re in greement with previous study on greenhouse-grown itter melons of different vrieties, whih showed strong positive orreltions etween TPC nd the AC mesured with the three ssys [12]. Therefore, these high orreltions strongly suggest tht the extrted phenoli ompounds, inluding those in the queous extrts of itter melon, possess potent ntioxidnt nd free rdil svenging tivities. This study supports the use of wter s the solvent of hoie for the extrtion of the phenoli ompounds from itter melon. However, whether the effiieny of extrtion for phenoli ompounds nd their ssoited AC from itter melon n e further improved using wter with other emerging modern ssisted-extrtion tehnologies, suh s ultrsonis [36], mirowve [37], pulsed eletri field [38], superritil fluid [39] nd pressurized liquid [40], needs to e investigted in future studies. 5. Conlusions This study demonstrted tht wter ould e used to effetively extrt phenoli ompounds nd their ssoited ntioxidnt tivities from itter melon. It ws shown tht the queous method ould e optimised to give n extrtion equivlent to tht otined with the est orgni solvent tested (% ethnol) nd less solvent nd less time ws required with wter thn with % ethnol. The optiml onditions for the queous extrtion were single extrtion t C for 5 min t wter-to-powder rtio of 40:1 ml/g nd powder prtile size of 1 mm. Therefore, this study provides evidene to reommend the use of wter s the solvent of hoie for the extrtion of the phenoli ompounds from itter melon.

14 Antioxidnts 2014, Aknowledgments The uthors grtefully knowledge the University of Newstle for grnting Sing P. Tn University of Newstle Postgrdute Reserh Sholrship (UNPRS). Author Contriutions Sing Pei Tn, Costs Stthopoulos, Sophie Prks nd Pul Roh ontriuted in experimentl design nd dt nlysis. Sing Pei Tn, Sophie Prks nd Pul Roh hve done mnusript preprtion nd dt interprettion. All uthors red nd pproved the finl mnusript. Conflits of Interest The uthors delre no onflit of interest. Referenes 1. Fng, E.F.; Zhng, C.Z.; Zhng, L.; Fong, W.P.; Ng, T.B. In vitro nd in vivo ntirinogeni effets of RNse MC2, rionulese isolted from dietry itter gourd, towrd humn liver ner ells. Int. J. Biohem. Cell Biol. 2012, 44, Ptel, S.; Ptel, T.; Prmr, K.; Bhtt, Y.; Ptel, Y.; Ptel, N.M. Isoltion, hrteriztion nd ntimiroil tivity of hrntin from Momordi hrnti linn. fruit. Int. J. Drug Dev. Res. 2010, 2, Hsu, C.; Tsi, T.-H.; Li, Y.-Y.; Wu, W.-H.; Hung, C.-J.; Tsi, P.-J. Wild itter melon (Momordi hrnti linn. vr. revit Ser.) extrt nd its iotive omponents suppress Propioniterium nes-indued inflmmtion. Food Chem. 2012, 135, Grover, J.K.; Ydv, S.P. Phrmologil tions nd potentil uses of Momordi hrnti: A review. J. Ethnophrmol. 2004, 93, Sthishsekr, D.; Surmnin, S. Antioxidnt properties of Momordi hrnti (itter gourd) seeds on streptozotoin indued dieti rts. Asi P. J. Clin. Nutr. 2005, 14, Semiz, A.; Sen, A. Antioxidnt nd hemoprotetive properties of Momordi hrnti L. (itter melon) fruit extrt. Afr. J. Biotehnol. 2007, 6, Lii, C.K.; Chen, H.W.; Yun, W.T.; Liu, K.L. Suppressive effets of wild itter gourd (Momordi hrnti linn. vr. revit Ser.) fruit extrts on inflmmtory responses in rw mrophges. J. Ethnophrmol. 2009, 122, Hminiuk, C.W.I.; Miel, G.M.; Plt-Oviedo, M.S.V.; Perlt, R.M. Phenoli ompounds in fruits An overview. Int. J. Food Si. Teh. 2012, 47, Horx, R.; Hettirhhy, N.; Islm, S. Totl phenoli ontents nd phenoli id onstituents in 4 vrieties of itter melons (Momordi hrnti) nd ntioxidnt tivities of their extrts. J. Food Si. 2005,, C275 C Horx, R.; Hettirhhy, N.; Chen, P. Extrtion, quntifition, nd ntioxidnt tivities of phenolis from perirp nd seeds of itter melons (Momordi hrnti) hrvested t three mturity stges (immture, mture, nd ripe). J. Agri. Food Chem. 2010, 58,

15 Antioxidnts 2014, Wu, S.J.; Ng, L.T. Antioxidnt nd free rdil svenging tivities of wild itter melon (Momordi hrnti linn. vr. revit Ser.) in Tiwn. LWT-Food Si. Tehnol. 2008, 41, Tn, S.P.; Prks, S.E.; Stthopoulos, C.E.; Roh, P.D. Greenhouse-grown itter melon: Prodution nd qulity hrteristis. J. Si. Food Agri. 2014, 94, Cerd, A.; Mrtínez, M.E.; Soto, C.; Poirrier, P.; Perez-Corre, J.R.; Vergr-Slins, J.R.; Zúñig, M.E. The enhnement of ntioxidnt ompounds extrted from Thymus vulgris using enzymes nd the effet of extrting solvent. Food Chem. 2013, 139, Negrão Murkmi, A.N.; de Mello Cstnho Amoni, R.D.; Prudênio, E.S.; Amnte, E.R.; de Mores Znott, L.; Mrshin, M.; Cunh Petrus, J.C.; Teófilo, R.F. Conentrtion of phenoli ompounds in queous mte (Ilex prguriensis A. St. Hil) extrt through nnofiltrtion. LWT-Food Si. Tehnol. 2011, 44, Kuol, J.; Sirimornpun, S. Phenoli ontents nd ntioxidnt tivities of itter gourd (Momordi hrnti L.) lef, stem nd fruit frtion extrts in vitro. Food Chem. 2008, 110, Meneses, N.G.T.; Mrtins, S.; Teixeir, J.A.; Musstto, S.I. Influene of extrtion solvents on the reovery of ntioxidnt phenoli ompounds from rewer s spent grins. Sep. Purif. Tehnol. 2013, 108, Alothmn, M.; Bht, R.; Krim, A.A. Antioxidnt pity nd phenoli ontent of seleted tropil fruits from mlysi, extrted with different solvents. Food Chem. 2009, 115, Vuong, Q.V.; Golding, J.B.; Stthopoulos, C.E.; Nguyen, M.H.; Roh, P.D. Optimizing onditions for the extrtion of tehins from green te using hot wter. J. Sep. Si. 2011, 34, Cio, N.; Lnorte, M.T.; Prggio, M.; Viggino, M.; Lttnzio, V. A reproduile, rpid nd inexpensive folin-iolteu miro-method in determining phenolis of plnt methnol extrts. Mirohem. J. 2009, 91, Re, R.; Pellegrini, N.; Proteggente, A.; Pnnl, A.; Yng, M.; Rie-Evns, C. Antioxidnt tivity pplying n improved ABTS rdil tion deoloriztion ssy. Free Rdi. Biol. Med. 1999, 26, Brnd-Willims, W.; Cuvelier, M.E.; Berset, C. Use of free rdil method to evlute ntioxidnt tivity. LWT-Food Si. Tehnol. 1995, 28, Benzie, I.F.F.; Strin, J.J. The ferri reduing ility of plsm (FRAP) s mesure of ntioxidnt power : The FRAP ssy. Anl. Biohem. 1996, 239, Spigno, G.; de Fveri, D.M. Antioxidnts from grpe stlks nd mr: Influene of extrtion proedure on yield, purity nd ntioxidnt power of the extrts. J. Food Eng. 2007, 78, Wissm, Z.; Ghd, B.; Wssim, A.; Wrid, K. Effetive extrtion of polyphenols nd pronthoynidins from pomegrnte s peel. Int. J. Phrm. Phrm. Si. 2012, 4, Sólyom, K.; Solá, R.; Coero, M.J.; Mto, R.B. Therml degrdtion of grpe mr polyphenols. Food Chem. 2014, 159, Rispil, N.; Morris, P.; We, K. Phenoli ompounds: Extrtion nd nlysis. In Lotus Jponius Hndook; Márquez, A., Ed.; Springer: Dordreht, The Netherlnds, 2005; pp Hirun, S.; Roh, P.D. An improved solvent extrtion method for the nlysis of tehins nd ffeine in green te. J. Food Nutr. Res. 2011,,

16 Antioxidnts 2014, Nepote, V.; Grosso, N.R.; Guzmán, C.A. Optimiztion of extrtion of phenoli ntioxidnts from penut skins. J. Si. Food Agri. 2005, 85, Vuong, Q.V.; Hirun, S.; Roh, P.D.; Bowyer, M.C.; Phillips, P.A.; Srlett, C.J. Effet of extrtion onditions on totl phenoli ompounds nd ntioxidnt tivities of Cri ppy lef queous extrts. J. Herl Med. 2013, 3, Alu dtt, M.H.; Alli, I.; Ereifej, K.; Alhmd, M.N.; Alsd, A.; Reh, T. Optimistion nd hrteristion of vrious extrtion onditions of phenoli ompounds nd ntioxidnt tivity in olive seeds. Nt. Prod. Res. 2011, 25, Wng, C.; Shi, L.; Fn, L.; Ding, Y.; Zho, S.; Liu, Y.; M, C. Optimiztion of extrtion nd enrihment of phenolis from pomegrnte (Puni grntum L.) leves. Ind. Crop. Prod. 2013, 42, Gertenh, D.D. Solid-liquid extrtion tehnologies for mnufturing nutreutils. In Funtionl Foods: Biohemil nd Proessing Aspets; Shi, J., Mzz, G., Mguer, M.L., Eds.; CRC Press: Bo Rton, FL, USA, 2002; pp You, Q.; Yin, X.; Zhng, S.; Jing, Z. Extrtion, purifition, nd ntioxidnt tivities of polyshrides from Triholom mongolium Imi. Crohydr. Polym. 2014, 99, Tn, S.P.; Prks, S.E.; Stthopoulos, C.E.; Roh, P.D. Extrtion of flvonoids from itter melon. Food Nutr. Si. 2014, 5, Wng, Z.; Pn, Z.; M, H.; Atungulu, G.G. Extrtion of phenolis from pomegrnte peels. Open Food Si. J. 2011, 5, Zu, G.; Zhng, R.; Yng, L.; M, C.; Zu, Y.; Wng, W.; Zho, C. Ultrsound-ssisted extrtion of rnosi id nd rosmrini id using ioni liquid solution from Rosmrinus offiinlis. Int. J. Mol. Si. 2012, 13, Chirem, C.; Rooney, L.W.; Bet, T. Mirowve-ssisted extrtion of ound phenoli ids in rn nd flour frtions from sorghum nd mize ultivrs vrying in hrdness. J. Agri. Food Chem. 2012,, Delsrt, C.; Ghidossi, R.; Poupot, C.; Cholet, C.; Grimi, N.; Voroiev, E.; Milisi, V.; Peuhot, M.M. Enhned extrtion of phenoli ompounds from merlot grpes y pulsed eletri field tretment. Am. J. Enol. Viti. 2012, 63, Ginnuzzo, A.N.; Boggetti, H.J.; Nzreno, M.A.; Mishim, H.T. Superritil fluid extrtion of nringin from the peel of Citrus prdisi. Phytohem. Anl. 2003, 14, Erdogn, S.; Ates, B.; Durmz, G.; Yilmz, I.; Sekin, T. Pressurized liquid extrtion of phenoli ompounds from Antoli propolis nd their rdil svenging pities. Food Chem. Toxiol. 2011, 49, y the uthors; liensee MDPI, Bsel, Switzerlnd. This rtile is n open ess rtile distriuted under the terms nd onditions of the Cretive Commons Attriution liense (

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