De elopmen o new ac i e packaging ilms coa ed wi h na u al phenolic
compounds o imp o e he oxida i e s abili y o bee
Le icia Ba bosa-Pe ei a, Goizane P. Au ekoe xea, Inmaculada Angulo,
Pe ec o Pasei o-Losada, Jos´e M. C uz
PII: S0309-1740(14)00042-4
DOI: doi: 10.1016/j.mea sci.2014.02.006
Re e ence: MESC 6365
To appea in: Mea Science
Recei ed da e: 23 Augus 2013
Re ised da e: 31 Janua y 2014
Accep ed da e: 4 Feb ua y 2014
Please ci e his a icle as: Ba bosa-Pe ei a, L., Au ekoe xea, G.P., Angulo, I., Pasei o-
Losada, P. & C uz, J.M., De elopmen o new ac i e packaging films coa ed wi h na u al
phenolic compounds o imp o e he oxida i e s abili y o bee , Mea Science (2014), doi:
10.1016/j.mea sci.2014.02.006
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DEVELOPMENT OF NEW ACTIVE PACKAGING FILMS COATED WITH
NATURAL PHENOLIC COMPOUNDS TO IMPROVE THE OXIDATIVE
STABILITY OF BEEF
[email p o ec ed]
Le icia Ba bosa-Pe ei a 1; Goizane P. Au ekoe xea2; Inmaculada Angulo2; Pe ec o
Pasei o-Losada, 1 José M. C uz3.
1Depa men o Analy ical Chemis y, Nu i ion and Food Science, Facul y o
Pha macy. Uni e si y o San iago de Compos ela, E-15782 Spain.
2 GAIKER Technological Cen e, 48170 Zamudio, Spain.
3Depa men o Chemical Enginee ing, Indus ial Enginee ing School, Uni e si y o
Vigo, 36310 Vigo, Spain.
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Abs ac
The aim o de elop ac i e packaging ilms con aining na u al an ioxidan s and o
e alua e hei capaci y o enhance he oxida i e s abili y o bee du ing e ige a ion.
The an ioxidan ac i i y o a na u al ex ac ob ained om a b ewe y esidual was e was
e alua ed and compa ed wi h ha o a comme cial osema y ex ac and wo syn he ic
an ioxidan s (BHT and p opyl galla e). Di e en concen a ions o each an ioxidan
we e also added di ec ly o bee samples, esul ing in a educ ion in lipid oxida ion o
up o 70-80 % ela i e o he con ol. Ac i e an ioxidan ilms coa ed wi h PVPP-WS
ex ac educed lipid oxida ion by up o 80 %, ela i e o he con ol, du ing cold
s o age. The use o ac i e packaging ilms con aining na u al ex ac s could imp o e he
oxida i e s abili y o mea p oduc s and should he e o e be o g ea in e es in he ood
indus y.
Keywo ds: Lipid oxida ion, bee , na u al an ioxidan s, coa ing, ac i e packaging.
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1. In oduc ion
Lipid pe oxida ion is a majo cause o de e io a ion o mea quali y du ing p ocessing,
dis ibu ion and e ige a ion, he eby educing shel s abili y and accep abili y. Lipid
oxida ion can p oduce changes in mea quali y pa ame e s, such as o ganolep ic
p ope ies and nu i ional alue, and i leads o he gene a ion and accumula ion o
compounds ha may pose isks o human heal h (G ay, Gomaa, & Buckley, 1996).
The oxida i e s abili y o mea can be ex ended by using an ioxidan s and p ope
packaging ma e ials (Zhou, Xu, & Liu, 2010).
Syn he ic an ioxidan s ha e long been used in he ood indus y o p e en o minimize
lipid oxida ion in ood p oduc s. Because o g owing conce ns abou he po en ial heal h
haza ds associa ed wi h syn he ic an ioxidan s commonly used in he ood indus y (e.g.
BHT, BHA and PG) and inc eased consume demand o na u al p oduc s, he e is a
g owing in e es in he use o na u ally occu ing an ioxidan s o use in ood p ocessing
(Shahidi, & Zhong, 2010).
Residual was e subs ances ob ained om ag o-indus ial by-p oduc s o e a p ac ical
and economic sou ce o po en an ioxidan s ha could eplace syn he ic p ese a i es
(Balasund am, Sund am, & Samman, 2006).
Poly inylpolypy olidone washing solu ion (PVPP-WS) ex ac is a na u al ex ac
ob ained om a b ewe y was e s eam. Du ing s o age o bee , colloidal haze can
de elop as a esul o he o ma ion o complexes be ween polypep ides and
polyphenols (Siebe , 1999). The nega i e impac o polyphenols on haze s abili y is
minimized by using poly inylpolypy olidone esin (PVPP) o s abilize bee and ex end
i s shel li e. PVPP s abiliza ion emo es a subs an ial pa o he polyphenols in bee
(bo h haze and non-haze ac i e polyphenols), which can be eco e ed om he PVPP
by an alkaline ea men (Mi chell, Hong, May, W igh , & Bam o h 2005).
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>The high an ioxidan ac i i y o he ex ac has been demons a ed in di e en in i o
expe imen s (Ba bosa-Pe ei a, Angulo, Pasei o-Losada, & C uz, 2013a). The
an ioxidan ac i i y o PVPP-WS ex ac is ela ed o he high concen a ions o
phenolic compounds, such as la onols (ca echin, galloca echin and epigalloca echin)
and hyd oxycinnamic and hyd oxybenzoic acids (gallic acid, ca eic acid, p-couma ic
acid and e ulic acid), which ac as ee adical accep o s and chain b eake s and a e
he e o e esponsible o he high ee adical sca enging ac i i y o he ex ac
(Ba bosa-Pe ei a e al, 2013a; Ba bosa-Pe ei a, Poche ille, Angulo, Pasei o-Losada, &
C uz, 2013b).
Na u al ex ac s om many he bs and spices ha e been s udied and used o ex end he
shel li e o oods (Balasund am e al., 2006; Fe nández-Lopez, Zhi, Aleson-Ca bonell,
Pé ez-Al a ez, & Ku i, 2005; Sánchez-Escalan e, Djenane, To escano, Bel án,
Roncales, 2003). Rosema y ex ac has been shown o possess s ong an ioxidan
ac i i y because o he high con en s o phenolic di e penes (e.g. ca nosic acid, ca nosol
and osmanol) and phenolic acids (e.g. osma inic acid), which ac as oxida i e chain
b eake s ia elec on dona ion (Zheng, & Wang, 2001).
Rosema y ex ac s ha e been widely used in he ood indus y, and many au ho s ha e
epo ed hei e ec i eness in educing lipid oxida ion in mea p oduc s. Ne e heless,
mos s udies epo ed in ol e he di ec addi ion o osema y o he packaged ood, and
ela i ely ew deal wi h he inclusion o osema y in he packaging ma e ial (Sánchez-
Escalan e e al., 2003; McB ide, Hogan, & Ke y, 2007; Ne ín e al., 2006).
Ac i e packaging is cu en ly one o he mos dynamic echnologies used o p ese e
he quali y o ood ia he elease o ac i e agen s om he packaging ilm. Release o
he ac i e agen s can be con olled o e an ex ended pe iod o ime o main ain o
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ex end he quali y and shel -li e o p oduc s, wi hou he need o di ec addi ion o any
subs ances o he oods u (Zhou e al., 2010; Lee, 2010).
Some s udies ha e e alua ed how an ioxidan s (such as BHT, BHA, alpha- ocophe ol
and na u al ex ac s) inco po a ed in packaging ilm mig a e ou o he ilm and e a d
lipid oxida ion in he s o ed oods u (Moo e, Han, Ac on, Ogale, Ba mo e, &Dawson,
2000; Ba bosa-Pe ei a e al., 2013c). The inco po a ion o osema y ex ac in ac i e
packaging ilm has been desc ibed by Ne ín e al. (2006), wi h p omising esul s in
ela ion o ex ending he shel li e o bee .
Ano he concep in ac i e packaging is he addi ion o bioac i e subs ances by a coa ing
p ocess. The de elopmen o coa ings wi h an imic obial capaci y has been s udied in
ela ion o p ese a ion o mea p oduc s (Zhou e al., 2010; Lee, 2010; Ke y, O’G ady,
& Hogan, 2006; Bonilla, A a és, Va gas, & Chi al , 2012). An ioxidan addi i es can
also be inco po a ed by coa ing hem on o ood packaging ma e ials o con ol spoilage
by oxida ion and o p ese e ood quali y (Ve mei en, D elieghe e, an Bees , & de
K uij , Debe e e, 1999; Lee, An, Lee, Pa k, & Lee, 2003).
The aim o his s udy was o e alua e and compa e he an ioxidan e ec o wo na u al
ex ac s (PVPP-WS and osema y ex ac ) and wo syn he ic an ioxidan s (BHT and
PG) on he oxida i e s abili y o bee du ing cold s o age. The na u al ex ac s we e
used o coa ac i e ilms wi h an ioxidan p ope ies. Finally, he e ec i eness o he
new an ioxidan ac i e packaging ilms in delaying lipid oxida ion o bee du ing cold
s o age was e alua ed in samples in which he packaging was wi h and wi hou di ec
con ac wi h he ood sample.
2. Ma e ials and me hods
2.1. Chemicals
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Bu yla ed hyd oxy oluene (BHT) (99.0%, CAS No. [128-37-0]), sodium azide
(99.0%, CAS No. [26628-22-8]), 2- hioba bi u ic acid (TBA) (≥98%, CAS No. [504-
17-6]) and ichlo oace ic acid (TCA) (pu iss. p.a. 99.5%, CAS No. [76-03-9]) we e
pu chased om Sigma-Ald ich (S einheim, Ge many). P opyl galla e (PG) (98%, CAS
No. [121-79-9]), 1,1,3,3- e ae hoxyp opane (TEP) (pu um ≥95% (GC), CAS No. [122-
31-6]) and 2, 2-diphenyl-1-pic ylhyd azyl (DPPH) (TECHN ≥85%, CAS No. [1898-66-
4]) we e supplied by Fluka Chemie AG (Buchs, Swi ze land). Me hanol (GC≥99.9%,
CAS No. [67-56-1]), o hophospho ic acid (85% GR o analysis, CAS No. [7664-38-
2]) and e hanol (absolu e o analysis, CAS No. [64-17-5]) we e p o ided by Me ck
(Da ms ad , Ge many).
2.2. Na u al ex ac s
PVPP-WS ex ac : his ex ac , which con ains na u al an ioxidan s, was ob ained om
a esidual s eam gene a ed du ing he PVPP cleaning p ocess in he b ewing indus y
by a p ocess desc ibed by Ba bosa-Pe ei a e al., (2014). In bee p oduc ion, a
cla i ica ion s ep is essen ial o imp o e bee s abili y. As a esul o his p ocess, a
PVPP sludge is ob ained. The PVPP sludge loaded wi h polyphenolic compounds was
washed wi h a NaOH solu ion (2% w/w) a oom empe a u e. A e he NaOH-PVPP
was il e ed, a clean PVPP esin and a PVPP washing solu ion (PVPP-WS) con aining
phenolic compounds we e ob ained.
The PVPP washing solu ion (PVPP-WS) was acidi ied o pH 1.5 wi h HCl (37%), and
polyphenolic compounds we e ex ac ed wi h e hyl ace a e by s i ing o 30 minu es a
oom empe a u e. O ganic and aqueous phases we e sepa a ed by decan a ion and he
o ganic phase was collec ed and e apo a ed o d yness a 40 ºC. Residual wa e was
emo ed om he ex ac by lyophilisa ion o yield he d y c ude ex ac (Ba bosa-
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Pe ei a, Angulo, Pasei o-Losada, & C uz, 2013a). The con en o phenolic compounds
is shown in Table 1a (Ba bosa-Pe ei a e al., 2013b).
Rosema y ex ac : comme cial osema y ex ac (MS-198-08 GIN 601331 Rosema y
Ex ac P) was supplied in powde o m by INGRENAT (Ing edien es na u ales SL.,
Mu cia, Spain). The composi ion o he osema y ex ac is shown in Table 1b.
2.3. Ins umen s
The concen a ion o 2- hioba bi u ic acid eac i e subs ances (TBARs) and he
abso bance in he DPPH me hod we e de e mined in a dual-beam spec opho ome e
(U ikon XL, Bio-Tek Ins umen s, Milan, I aly).
Seconda y oxida ion compounds we e ex ac ed om bee by use o a T 25
ULTRA-TURRAX digi al homogenize and an MS2 Mini Vo ex Shake (bo h om
IKA).
2.4. An ioxidan ac i i y o na u al ex ac s – DPPH me hod
The an ioxidan ac i i y o he na u al ex ac s was de e mined by he DPPH
(2,2-diphenyl-1-pic ylhyd azyl) adical sca enging me hod desc ibed by on Gadow,
Joube , and Hansmann (1997), wi h sligh modi ica ions.
S anda d solu ions o he di e en an ioxidan s and o wo syn he ic compounds
wi h an ioxidan p ope ies usually used in he ood indus y, PG and BHT, we e
p epa ed in me hanol. An aliquo o an ioxidan (50 µL) was added o 2 mL o DPPH
adical me hanolic solu ion (3.6 × 10-5 M), and he solu ion was shaken igo ously on a
o ex shake and le o s and in he da k, o 16 min a oom empe a u e. The
abso bance o he solu ion was hen de e mined a 515 nm. All de e mina ions we e
pe o med in iplica e. The dec ease in abso bance was con e ed o DPPH inhibi ion
pe cen age (IP), acco ding o he ollowing equa ion:
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whe e
A0 is he abso bance o he con ol a ini ial ime;
A16 is he abso bance o he sample a e incuba ion o 16 minu es.
The concen a ion o an ioxidan compound o na u al ex ac equi ed o achie e 50 %
inhibi ion o he adical DPPH (Equi alen concen a ion=EC50) was de e mined om
he linea eg ession cu e (i.e. he di e en concen a ions o an ioxidan [wi hin he
ange 0.1 o 5 g L-1] plo ed agains he pe cen age o ee adical sca enging ac i i y
[IP %]).
2.5. P ocessing o ac i e packaging samples by coa ing
Se e al o mula ions o he an ioxidan compounds plus a low densi y polye hylene
(LDPE) ma ix we e p epa ed. Ac i e ilms we e p epa ed wi h di e en an ioxidan
con en s and pe cen ages o compounds o s udy he an ioxidan e ec i eness o he
polyme o mula ions in he bee . All coa ings we e applied wi h a od o 40 mic ons
(TR40) a a speed o 90 mm/sec. The inal weigh was simila o ha used in he
packaging indus y (3.2 g m-2). The o mula ions a e shown in Table 2. The
concen a ions employed o o mula e he ac i e ilms (exp essed in %) e e o he
weigh o poly inylic esin used in he p ocess o coa ing, so ha he amoun o na u al
ex ac used o p oduce hese ilms is lowe han in he assay o which he ex ac was
di ec ly added.
2.6. E alua ion o an ioxidan ac i i y in ood
2.6.1. Bee samples
F eshly cu bee , o hickness 1 cm, was pu chased in a local e ail s o e. The
mea was di ided in o small pieces o 50 1 g and o su ace a ea 8.5 × 8.5 cm. A small
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oxida ion in bee samples du ing he s o age. The esul s, exp essed as mg MDA Kg-1 o
sample, a e shown in Table 5. Two con ol es s we e pe o med, a es wi hou ilm o
e alua e he oxida ion o bee (con ol wi hou ilm), and a es wi h LDPE ilm wi hou
an ioxidan ex ac added , o e alua e he e ec o he ilm on he su ace o he mea
sample (con ol ilm). LDPE ilms spiked wi h osema y ex ac a di e en
concen a ions (3, 10 and 20 % (w/w) yielded ilms R 3 %, R 10 % and R 20 %
espec i ely (Table 2). Film R 20 % HS is he same as ilm R 20 %, excep ha i is no
in di ec con ac wi h he samples, exe ing i s e ec in he headspace o he con aine .
The same nomencla u e (Table 2) was used wi h he ilms inco po a ing he PVPP-WS
ex ac a he same concen a ions (PVPP-WS 3 %, 10 %, 20 % and 20 % HS). All he
ac i e ilms es ed exhibi ed an e ec ha p o ec ed he bee om oxida ion (Table 5).
The osema y ex ac -coa ed ac i e ilms in con ac wi h mea samples yielded a
educ ion o app oxima ely 50 % in he TBARs alues. A he 9 h day o s o age he
educ ion o TBARs alues was a ound 60% wi h espec o he con ol. Sligh
di e ences we e obse ed o he h ee concen a ions used in he educ ion o lipid
oxida ion ela i e o he con ol . This e ec inc eased wi h he amoun o osema y
ex ac used o de elop he ac i e ilm in he o de 20% > 10% > 3%. The PVPP-WS
ex ac was mo e e ec i e in educing lipid oxida ion han he osema y ex ac , wi h
educ ions in TBARs alues highe han 60% a he 9 h day o s o age. This was mo e
e iden a he highes concen a ion applied (20 %), which delayed he onse o
oxida ion un il he nin h day, a e which sligh oxida ion was obse ed, bu which was
much lowe han in he o he samples, wi h a educ ion o 93 % wi h espec o he
con ol wi hou ilm. Howe e , all he ac i e ilms subs an ially educed lipid oxida ion
in bee . The con ol ilm in con ac wi h he su ace educes lipid oxida ion because less
sample su ace is in con ac wi h he oxygen in he headspace o he con aine when
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compa ed wi h he con ol wi hou ilm. This may explain he e ec o he ac i e ilms
in he headspace o he con aine , which showed less educ ion in lipid oxida ion han
he con ol ilm. The e was some e ec o hese na u al ex ac s in he headspace o he
con aine ha could be due o hei capaci y o ac as sca enge s o oxygen and/o
adicals esponsible o he oxida ion p ocess. These esul s a e in ag eemen wi h
esul s o polyp opylene ilms spiked wi h osema y ex ac a a concen a ion o 1%
when s o ed o 29 days (Ne ín e al., 2008). The PVPP-WS ex ac was also e ec i e,
al hough o a lesse ex en ( educ ion o 6.6% wi h espec o con ol wi hou ilm).
Howe e , inhibi ion o oxida ion was less han ha ob ained wi h a simple polyme in
close con ac wi h he sample wi hou ac i e compounds. I appea s ha close con ac
be ween he ac i e ilm and he mea sample is equi ed o a la ge educ ion in lipid
oxida ion in mea samples.
The ac i e ilms de eloped in he p esen s udy ha e an inhibi o y e ec on lipid
oxida ion compa able o ha obse ed a e di ec addi ion o he an ioxidan s o he
mea sample sec ion 3.2). The esul s ob ained wi h he PVPP-WS 20 % ilm (p oduced
wi h he PVPP-WS ex ac ) showed he e ec i eness o he na u al ex ac ob ained
om he b ewe y indus y and con i m he possible use o he ex ac as a ood
an ioxidan , as ecognised o osema y ex ac (Bozku e al., 2008; T indade e al.,
2010; Fe nandez-Lopez e al., 2005). The esul s ob ained wi h he ood samples a e
consis en wi h hose ob ained wi h he DPPH me hod (sec ion 3.1), which con i ms ha
hese na u al ex ac s display a adical sca enging capaci y and ha his may be one o
he mechanisms o ac ion whe eby he ex ac s educe lipid oxida ion in mea samples.
4. Conclusions
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The PVPP-WS ex ac displays a highe deg ee o adical sca enging ac i i y han
osema y ex ac and BHT, a syn he ic an ioxidan commonly used in he ood indus y.
Na u al ex ac s p o ed o be e ec i e an ioxidan s and educed lipid oxida ion
when added di ec ly o he su ace o e ige a ed bee samples and he e o e he di ec
con ac wi h oods u is manda o y o ob ain a signi ican educ ion in lipid oxida ion
o bee samples. The e o e, i may be possible o use hese na u al ex ac s o eplace
syn he ic an ioxidan s in ood. The PVPP-WS ex ac displays a simila an ioxidan
e ec o PG in educing lipid oxida ion, and was mo e e ec i e han BHT and osema y
ex ac . Ac i e ilms con aining na u al ex ac s we e success ully p oduced, and he use
o hese ac i e ilms coa ed wi h na u al an ioxidan s enhanced oxida i e s abili y o
bee ela i e o ha ob ained wi h he ilm con ol du ing cold s o age. The bes esul s
we e ob ained wi h he ex ac ob ained om he b ewe y esidual s eam (PVPP-WS),
which educed lipid oxida ion by up o 90 %. These ac i e ilms appea p omising o
he de elopmen o ac i e an ioxidan packaging o use wi h mea p oduc s.
Acknowledgemen s
This wo k was inancially suppo ed by he Minis y o Educa ion and Science
o Spain - CENIT P og am - Na ional S a egic Conso ium in Technical Resea ch
(CENIT-2007-2016-FUTURAL). The au ho s a e g a e ul o he Mahou-San Miguel
G oup and FUTURAL p ojec (Ingenio P og am – CDTI).
The au ho s exp ess hei since e hanks o Ms. Pa icia Blanco Ca o, Ms.
C is ina Casal Rome o and M . Gonzalo He melo Vidal o hei excellen echnical
assis ance.
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Table 1a. To al and indi idual phenolic compounds (mg g-1) in he PVPP-WS ex ac
Phenolic compound (mg g-1)
Benzoic acid de i a es
38.1
Cinnamic acids
59.2
Fla onols
48.9
Gallic acid
20.1
Ca eic acid
14.1
Isoque ce in
28.3
P o oca echuic acid
15.5
p-couma ic acid
11.4
Que ce in
14.5
4-hyd oxybenzoic acid
2.54
Fe ulic acid
33.7
Kaemp e ol
6.06
Fla an-3-ols
214
Fla anones
14.6
Ace ophenone de i a es
14.6
Galloca echin
132
Na ingenin
Ace osy ingone
Epigalloca echin
30.6
Ca echin
29.9
Fla ones
8.10
S ilbenoids
5.35
Epica echin
21.4
Apigenin
Res e a ol
To al phenolic compounds p esen in he PVPP-WS ex ac , 403 mg g-1
Table 1b. MS-198-08 GIN 601331 Phenolic composi ion o he osema y ex ac .
Compound (mg g-1)
Phenolic di e penes
101.32
Ca nosic acid
87.18
Ca nosol
14.14
Excipien
Mal odex in
898.68
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Table 2. Fo mula ions o he LDPE coa ings (% (w/w)).
Fo mula ions
Na u al ex ac s
Rosema y
PVPP-WS
Film Con ol
-
-
Film R 3%
3 %
-
Film R 10%
10 %
-
Film R 20%
20 %
-
Film PVPP-WS 3%
-
3 %
Film PVPP-WS 10%
-
10 %
Film PVPP-WS 20%
-
20 %
Table 3. F ee adical sca enging ac i i y – DPPH
An ioxidan
EC50 (g L-1)*
BHT
2.64±0.025a
PG
0.046±0.002b
Rosema y ex ac
2.10±0.013c
PVPP-WS ex ac
0.346 ±0.007d
Values a e means o h ee de e mina ions. Di e en le e s mean s a is ically signi ican di e ences a P
< 0.05.
