Professional Documents
Culture Documents
DOI 10.1007/s13197-012-0887-5
REVIEW
Revised: 9 August 2012 / Accepted: 30 October 2012 / Published online: 23 November 2012
# Association of Food Scientists & Technologists (India) 2012
al. 2011; González-Montelongo et al. 2009), longan (Prasad et radiation, deactivating singlet oxygen or binding of metal ion
al. 2009), dragon fruit (Wu et al. 2006), rambutan (Okonogi et (Maisuthisakul et al. 2007; Shahidi and Naczk 1995;
al. 2007), sapodilla (Devatkal et al. 2011) and mangosteen Tachakittirungrod et al. 2007).
(Zadernowski et al. 2009). In general, antioxidant assays are classified as single
Mangosteen (Garcinia mangostana L.) is known as “the electron transfer and hydrogen atom transfer based assays.
queen of fruits” because it is one of the best tasting tropical Selection of methods for evaluating antioxidant property
fruits. The edible aril of mangosteen is milky white, while depends on the oxidation sources. Thus, many analytical
the peel is dark red and composes about two times of the methods are necessary to evaluate different antioxidant
edible portion (Fu et al. 2007; Zarena and Udaya Sankar effects. As shown in Table 1, the antioxidant properties of
2012). The traditional use of mangosteen is manifold. mangosteen peel extract can be divided into four groups
Mangosteen is mainly consumed fresh as dessert. including free radical scavenging, chelating ability, reducing
However, the production of wine, preserves, jam and puree power and lipid oxidation inhibitory ability based on the
from the aril are further traditional food applications (Bin antioxidant measurements. The antioxidant activity of man-
Osman and Milan 2006). Processing of mangosteen gener- gosteen peel extract has been reported using the following
ally involves separating the desired aril from the peel con- methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, 2,2-
sidered as waste. Recently, the mangosteen fruit extract is azinobis(3-ethylbenzothia-zoline-6-sulfonic acid) diammo-
popularly used as a food supplement, while the fruit peel nium salt (ABTS) cation radical, superoxide anion radical
extract has been used in herbal medicines. The mangosteen (O2•-), nitric oxide radical (•NO) and peroxynitrite (ONOO-)
peel has been reported to contain a variety of bioactive scavenging activity, the deoxyribose assay, hydroxyl radical
compounds with potential applications as therapeutic agents (•OH) scavenging activity, oxygen radical absorbance capac-
or as functional food additives such as phenolic acids ity (ORAC), ferrous ion (Fe2+) chelating activity, ferric reduc-
(Zadernowski et al. 2009), tannins (Pothitirat et al. 2009), ing antioxidant power (FRAP), phosphomolybdenum
xanthones (Zarena and Udaya Sankar 2009b), anthocyanins method, cytochrome c reducing capacity, ferric thiocyanate
(Palapol et al. 2009) and other bioactive compounds. These method (FTC) and thiobarbituric acid (TBA) assay.
isolated compounds have various biological effects such as
antioxidant (Jung et al. 2006), antimicrobial (Suksamrarn et 1) The measurement techniques of free radical scavenging
al. 2002) and anti-inflammatory (Chen et al. 2008) activi- abilities
ties. The objective of the present work is to review the
methods for determining antioxidant activity of mangosteen DPPH radical scavenging activity measures the antioxi-
peel extract with respect to its bioactive components. dant ability for donating hydrogen atom to capture the
Factors influencing antioxidant property and the potential DPPH radical (DPPH•). As the DPPH• are quenched by
uses of the mangosteen peel extract are also included. antioxidant, the color of DPPH solution changes from a
deep purple to a light yellow and the absorbance at
515 nm decreases. (Bondet et al. 1997; Lim et al. 2007;
Methods for determining antioxidant activity Surveswaran et al. 2007). ABTS radical cation (ABTS•+)
of mangosteen peel extract scavenging activity measures the relative ability of antioxi-
dant to scavenge the ABTS•+ similar to the DPPH method.
Antioxidants are substances that can delay or prevent the In this analysis, the ABTS•+ are generated by reaction of a
oxidation process by inhibiting the initiation or propagation strong oxidizing agent (potassium persulfate) with the
of oxidation chain reaction. Antioxidants act through several ABTS. The reduction of ABTS•+ concentration (decreased
mechanisms: free radical scavenging, chelating of metal ion, blue-green color of the solution) occurs by donating hydro-
reducing activity and quenching of singlet oxygen. gen atom to quench the ABTS•+, which can be measured by
Antioxidants can be classified according to their protective the absorption spectrum at characteristic wavelength (734 or
properties at different stages in the oxidation process and 414 nm) (Surveswaran et al. 2007; Villaño et al. 2004).
since they act by different mechanisms, they are divided into DPPH and ABTS assays are effective and frequently
two main types of antioxidants, i.e., primary and secondary employed methods for evaluating the radical scavenging
antioxidants. Primary antioxidants can inhibit or retard ox- activity of antioxidant compounds because they are rapid
idation by scavenging free radicals (i.e. reactive oxygen and simple measurement techniques. Considering the occur-
species, e.g. hydroxyl, superoxide, nitric oxide, thiyl and rence of radical compound of both assays, the ABTS•+ are
peroxyl) by donating of hydrogen atom or electron, which generated by reaction of a strong oxidizing agent with the
convert their radicals to more stable products. Secondary ABTS whereas DPPH• need not to be generated (Kedare
antioxidants display a function by many mechanisms includ- and Singh 2011; Re et al. 1999; Villaño et al. 2004). It is
ing scavenging oxygen and hydrogen peroxide, absorbing UV revealed that DPPH• is more stable than ABTS•+. However,
3548 J Food Sci Technol (December 2014) 51(12):3546–3558
Table 1 Analytical methods used to assess antioxidant activity of DPPH• can only be dissolved in organic media (especially in
mangosteen peel
alcoholic media), not in aqueous media, which is an impor-
Assay References tant limitation when interpreting the role of hydrophilic
antioxidants (Arnao 2000). On the other hand, ABTS•+
Scavenging of radical can be solubilized in both aqueous and in organic media
1,1-diphenyl-2-picrylhydrazyl Yoshikawa et al. (1994) and is not affected by ionic strength, so the antioxidant
radical scavenging activity Kosem et al. (2007) activity can be measured due to the hydrophilic and lipo-
Maisuthisakul et al. (2007) philic nature of the compounds (Arnao 2000). Floegel et al.
Okonogi et al. (2007) (2011) reported that the high-pigmented and hydrophilic
Surveswaran et al. (2007) antioxidants were better reflected by ABTS assay than
Yu et al. (2007) DPPH assay. O2•- scavenging activity is measured by elec-
Pothitirat et al. (2009) tron spin resonance (ESR) spin-trapping technique. In the
Zarena and Udaya ESR spin-trapping, the O2•- generators are trapped by spin-
Sankar (2009a) trapping (5,5-dimethyl-1-pyrroline N-oxide, DMPO) to
2,2´-azinobis(3-ethylbenzothiazoline- Okonogi et al. (2007) form the spin adducts (DMPO-OOH). The ESR signal in-
6-sulfonic acid) radical cation Surveswaran et al. (2007)
scavenging activity
tensities are dependent on the amount of DMPO-OOH, that
Tachakittirungrod et al. measured by the ESR spectrometry under the specific con-
(2007)
dition (Kosem et al. 2007; Shimamura et al. 2007). •NO
Zarena and Udaya
scavenging activity is based on the amount of nitrite ion
Sankar (2009a)
(NO2-). The •NO generator (sodium nitroprusside) sponta-
Superoxide anion radical Kosem et al. (2007)
scavenging activity neously generates •NO, which interacts with oxygen to
Yu et al. (2007)
produce NO2- and the subsequent NO2- reacts with Griess
Nitric oxide radical scavenging Kosem et al. (2007)
activity reagent. The reaction products are measured at 550 nm
Peroxynitrite scavenging activity Jung et al. (2006) (Amano and Noda 1995; Kosem et al. 2007). ONOO- scav-
The deoxyribose assay Zarena and Udaya enging activity is determined by monitoring the oxidation of
Sankar (2009c) dihydrorhodamine 123 (DHR 123). In this assay, DHR 123
Hydroxyl radical scavenging Garcia et al. (2005) is oxidized by native ONOO- and ONOO--derived from the
activity Kosem et al. (2007) peroxynitrite donor 3-morpholinosydnonimine hydrochlo-
Yu et al. (2007) ride (SIN-1). The oxidized DHR 123 is evaluated by the
Chin et al. (2008) luminescence spectrometer on the excitation and emission
Oxygen radical absorbance Fu et al. (2007) wavelengths at 480 and 530 nm, respectively. The ONOO-
capacity scavenging activity relates to the fluorescence intensities of
Chelating of metal ions
oxidized DHR 123 (Shin et al. 2005; Zou et al. 2005). The
Ferrous ion chelating activity Zarena and Udaya
deoxyribose assay measures the scavenging of HO•. This
Sankar (2009a)
assay consists of deoxyribose, hydrogen peroxide (H2O2),
Kosem et al. (2007)
ferric ion (Fe3+), ethylene diamine tetraacetic acid (EDTA),
Reducing activity
reducing agent (ascorbate) and thiobarbituric acid (TBA).
Ferric reducing antioxidant Kosem et al. (2007)
power The deoxyribose is attacked by HO•, which is generated by
Surveswaran et al. (2007)
the reaction of H2O2 and Fe 2+-EDTA complex. During
Zarena and Udaya
Sankar (2009a) heating with TBA at low pH, deoxyribose- HO• complex
Phosphomolybdenum method Zarena and Udaya
is changed to a pink chromogen, which can be measured by
Sankar (2009b) the absorbance at 535 nm (Halliwell et al. 1987; Zarena and
Cytochrome c reducing capacity Zarena and Udaya Udaya Sankar 2009c). ORAC contains a peroxyl radical
Sankar (2009b) (RO2•) induced by 2, 2’-azobis(2-amidinopropane) dihy-
Scavenging of lipid oxidation products drochloride and the fluorescent marker protein, i.e.,
Ferric thiocyanate method Yoshikawa et al. (1994) fluorescein. This method is based on the inhibition of
Garcia et al. (2005) RO2•-induced oxidation of the fluorescein. The loss of
Kosem et al. (2007) fluorescence of fluorescein indicates the RO2• -induced
Yu et al. (2007) free radical damage. The antioxidant efficiency is deter-
Thiobarbituric acid assay (TBA) Zarena and Udaya mined by assessing the area under the fluorescence
Sankar (2009b) decay curve of the sample as compared to that of the
blank in which no antioxidant exists (Huang et al. 2002;
Prior et al. 2003).
J Food Sci Technol (December 2014) 51(12):3546–3558 3549
2) The measurement technique of chelating ability consists of ammonium thiocyanate and Fe2+ in acidic solu-
tion. H2O2 induced by lipid oxidation oxidizes Fe2+ to Fe3+,
The metal chelating ability is an important antioxidant
resulting in the formation of a red colored Fe3+-thiocyanate
property. This technique evaluates the ability of substances
complex. The levels of oxidation are determined by mea-
to reduce the concentration of free transition metals ion that
suring the absorbance at 500 nm (Kosem et al. 2007; Yu et
may act as a catalyst to generate the free radical to initiate
al. 2007). On the other hand, TBA measures the amount of
the oxidation reaction. Among the transition metals, iron is
malondialdehyde (MDA) produced during the second stage
known as the most important lipid oxidation pro-oxidant
of the lipid oxidation. This method is based on the MDA
due to its high reactivity. Ferrous ion (Fe2+) is the most
reaction with thiobarbituric acid to obtain a red pigment,
powerful pro-oxidant among the various species of metal
resulting from the condensation of two molecules of TBA
ions (Gülçin et al. 2004). The Fe2+-chelating activity test is
with one molecule of MDA. The levels of oxidation are
one of the most effective methods for measuring the chelat-
determined by measuring the absorbance at 535 nm
ing ability of antioxidant compounds because Fe2+ is an
(Fernández et al. 1997; Zarena and Udaya Sankar 2009b).
important catalyst for Fenton reaction and hydrogenperox-
ide decomposition that are cause of many diseases (Jayasri
et al. 2009; Lim et al. 2007; Liu et al. 2010; Yeh et al. 2011).
Factors affecting antioxidant activity of mangosteen peel
The Fe2+ chelating activity measures the ability of antioxi-
extract
dant to combine with Fe2+, whereas residual Fe2+ can com-
bine with particular compounds (ferrozine or potassium
The quality of mangosteen peel extract and its antioxidative
ferricyanide) to form the complex compounds (Ferrozine-
performances depends not only on the quality of mangosteen
Fe2+ or potassium hexacyanoferrate), which can be measured
peel but also environmental and technological factors affect-
using absorbance at specific wavelength (562 or 700 nm)
ing the activities of antioxidants from mangosteen peel.
(Kosem et al. 2007; Zarena and Udaya Sankar 2009a). The
Fe2+ chelating activity is calculated by Ferrozine-Fe2+ or 1) Maturation stage
potassium hexacyanoferrate absorbance which decreasing in
Total bioactive compound content and antioxidant activity
absorbance indicates strong chelating ability.
were found to be different in various maturation stages of
3) The measurement techniques of reducing ability mangosteen fruit (Pothitirat et al. 2009). The young fruit peel
FRAP measures antioxidant power with the assistance of (green peel) contained higher total phenolic (42.57 g gallic
an oxidant, i.e., Fe3+. In the FRAP assay, the antioxidants acid equivalents/100 g) and total tannin contents (51.25 g
reducing the Fe3+-tripyridyltriazine complex at low pH tannic acid equivalents/100 g) than the mature fruit peel (dark
causes the formation of a blue colored Fe2+-tripyridyltria- reddish purple peel) (28.88 g gallic acid equivalents/100 g and
zine complex. FRAP values are obtained by comparing the 36.66 g tannic acid equivalents/100 g), whereas the mature
absorbance change at 593 nm in test reaction mixtures with fruit peel had higher total flavonoid content (4.08 g quercetin
those containing standard antioxidant in known concentra- equivalents/100 g) than the young fruit peel (2.91 g quercetin
tion (Surveswaran et al. 2007; Zarena and Udaya Sankar equivalents/100 g). The results suggest that total phenolic and
2009a). Phosphomolybdenum method is based on the re- total tannin contents decreasing during the maturity stage of
duction of molybdate (Mo) ion from Mo6+ to Mo5+ by the the mangosteen fruit may be indicated by the reduction of a
action of electron donating antioxidants and the subsequent bitter yellowish resin. In addition, total flavonoid content
formation of a green phosphate-Mo5+ complex at acid pH, increasing during the maturity stage of the mangosteen fruit
which can be measured at 695 nm (Prieto et al. 1999; Zarena is indicated by dark purple color of anthocyanin accumulation.
and Udaya Sankar 2009b). The cytochrome c reducing capac- Congruently, it was found that total anthocyanin content (167,
ity measures ferrocytochrome c quantity at 550 nm, due to its 278, 509, 1,111, 1,824 and 4,235 g/kg for stage 1–6, respec-
active heme group containing a Fe2+, which has a character- tively) increased continuously during maturation and reached
istic spectrum at 550 nm. In this assay, cytochrome c is a maximum value (4,235 g/kg) at fully mature stage (Palapol
oxidized by oxygen saturated phosphate buffer to ferric cyto- et al. 2009). In consideration of antioxidant activity, the young
chrome c, thereafter the antioxidants reduce ferric cytochrome fruit peel possessed about two-fold higher free radical scav-
c to ferrocytochrome c (Zarena and Udaya Sankar 2009b). enging activity (EC50 05.56 μg/ml) than the mature fruit peel
(EC50 010.94 μg/ml) (Pothitirat et al. 2009). The higher anti-
4) The measurement techniques of lipid oxidation inhibitory oxidant activity of the young fruit peel may be resulted from
abilities the higher total phenolic and total tannin contents. The results
possibly indicate that the tannin present in the mangosteen
FTC measures the amount of peroxide produced during peel mainly acts through the mechanism of free radical
the initial stage of the lipid oxidation. The FTC assay scavenging.
3550 J Food Sci Technol (December 2014) 51(12):3546–3558
anthocyanins, proanthocyanidins, (−)-epicatechin and Trolox equivalents/g) than grape seed proanthocyanidins
xanthones were noticed in the mangosteen peel. (1.0×104 μmol Trolox equivalents/g), pine bark proantho-
Anthocyanins are the main compounds for indicating the cyanidins (7.5×103 μmol Trolox equivalents/g) and Trolox
maturation stages of mangosteen. Cyanidin-3-sophoroside (4.0×103 μmol Trolox equivalents/g) (Fu et al. 2007). The
(Fig. 2b) and cyanidin-3-glucoside (Fig. 2c) were identified results may be due to the compositional difference and the
as the main anthocyanins in the mangosteen peel (Du and difference of the degree of polymerization of the mango-
Francis 1977). Furthermore, the changes of these anthocya- steen proanthocyanidins, compared with other proanthocya-
nins during mangosteen development are reported. The con- nidins from different sources. In addition, the mangosteen
centration of cyanidin-3-sophoroside and cyanidin-3- OPCs contain (−)epicatechin as the predominant monomeric
glucoside increased according to increasing of mangosteen unit, reported as a better free radical scavenger (Fu et al.
maturation. In addition, other anthocyanins (cyanidin-gluco- 2010; Schwartz et al. 2007; Yu et al. 2007). (−)Epicatechin
side-pentoside, cyanidin-glucoside-X, cyanidin-X2 and is a polyphenol and the presence of two OH substitutions at
cyanidin-X, X denotes a residue of m/z 190 which is unified the ortho position of the phenolic ring results in higher
atomic mass units) were identified in the mangosteen peel of antioxidant activity. α-Mangostin was the first xanthone,
mangosteen (Palapol et al. 2009). Recently, pelargonidin-3- which was isolated from mangosteen peel (Pedraza-
glucoside (Fig. 2d) was identified from the mangosteen peel. Chaverrí et al. 2008) and has been reported as an antioxi-
The molecular formula of this compound was C21H21O10. In dant. Wittenauer et al. (2012) showed that α-mangostin was
addition, the quantities of three anthocyanins were reported. the major xanthone in mangosteen peel which was about
Cyanidin-3-sophoroside was the largest amount (76.1 %) fol- 69 % of the total amount of xanthones. α-Mangostin was
lowed by cyanidin-3-glucoside (13.4 %) and pelargonidin 3- able to scavenge in a concentration-dependent way singlet
glucoside (6.2 %), respectively (Zarena and Udaya Sankar oxygen (IC50 04.6 μM), O2•- (IC50 024.8 μM) and ONOO-
2012). Fu et al. (2007) reported that the high quantity of (IC50 023.3 μM). However, α-mangostin was unable to
anthocyanins in the peel related to the occurrence of proan- scavenge •OH and H2O2 (Guzmán-Beltrán et al. 2008;
thocyanidins or condensed tannins (Chen et al. 2009; Pedraza-Chaverrí et al. 2009). Chin et al. (2008) revealed
Schwartz et al. 2007). Correspondingly, procyanidin A-2 that γ-mangostin was only found to be active for HO•
(Fig. 2e) and procyanidin B-2 (Fig. 2f) were demonstrated scavenging assay (IC50 00.20 μg/ml) when compared with
as active principle compounds in the mangosteen peel fifteen xanthones (IC50 >10 μg/ml). Similarly, γ-mangostin
(Yoshikawa et al. 1994). (−)Epicatechin (Fig. 2g) is one of possessed DPPH • scavenging activity similar to α-
the most flavan-3-ols (Shahidi and Naczk 1995), which are tocopherol. Additionally, in vitro effect of γ-mangostin on
predominant monomeric unit of mangosteen proanthocyani- inhibitory ability of lipid oxidation exhibited higher antiox-
dins; consequently, they are often found together in the man- idant activity than BHA and α-tocopherol (Yoshikawa et al.
gosteen peel (Yoshikawa et al. 1994; Yu et al. 2007). On the 1994). Furthermore, the antioxidant activities of three man-
other hand, the isolated xanthones from mangosteen peel are gosteen xanthones, i.e., 1,3,6,7-tetrahydroxy-2,8-(3-methyl-
the most studied by several research groups. Fifty-two isolated 2-butenyl) (P1), 1,3,6-trihydroxy-7-methoxy-2,8-(3-methyl-
xanthones from mangosteen peel were reviewed (Chin et al. 2-butenyl)xanthone (P2) and (−)epicatechin (P3), were eval-
2008; Pedraza-Chaverrí et al. 2008). Recently, garcimangos- uated by different tests. P1 exhibited the highest DPPH• and
xanthone A (Fig. 2h), garcimangosxanthone B (Fig. 2i) and HO• scavenging activity, and inhibitory ability on lipid
garcimangosxanthone C (Fig. 2j) were identified from the oxidation, whereas P2 and P3 exhibited higher O2•- scaveng-
mangosteen peel. The molecular formula of these compounds ing activity than P1. The three phenolic compounds showed
were C21H18O6, C23H24O7 and C19,H22O6, respectively higher DPPH• and O2•- scavenging activity than Trolox and
(Zhang et al. 2010). Currently fifty-five isolated xanthones BHA, respectively. P1 showed higher HO• scavenging ac-
from mangosteen peel have been reported. tivity than α-tocopherol, Trolox and BHA, and higher in-
hibitory ability on lipid oxidation than α-tocopherol and
Trolox. Correspondingly, P2 and P3 showed higher inhibi-
Antioxidant activity of bioactive compounds tory ability on lipid oxidation than Trolox (Yu et al. 2007).
from mangosteen peel Additionally, the potential antioxidant activities of fourteen
mangosteen xanthones were demonstrated (Jung et al. 2006).
Effectiveness of oligomeric proanthocyanidins (OPCs) iso- Of these, 8-hydroxycudraxanthone G (Fig. 3b), smeathxan-
lated from mangosteen peel for scavenging RO2• were thone A (Fig. 3c) and gartanin (Fig. 3d) possessed better
reported, compared with Trolox (6-hydroxy-2,5,7,8-tetra ONOO- scavenging activities. Suvarnakuta et al. (2011)
methylchroman-2-carboxylic acid) and commercially avail- reported that 8-deoxygartanin (Fig. 3e) revealed higher anti-
able sources. The mangosteen OPCs are excellent RO2• oxidant activity than α-mangostin (Fig. 3f). The results are
scavengers, showing higher ORAC value (1.7×104 μmol possibly due to the specific form of chemical structure.
3554 J Food Sci Technol (December 2014) 51(12):3546–3558
Considering the correlation between antioxidant activity as electron withdrawing effect was observed when the OH is
and chemical structure of bioactive compounds, some con- at the meta (m-) position (Fig. 5). The results are possibly due
clusions can be summarized. Firstly, polyphenol structure to the appearance of two OH groups at the o- or p-positions of
shows higher antioxidant activity than monophenol structure. conjugated ring resulting in the decrease of the O-H bond
For example, hydroquinone, catechol and resorcinol strength and the subsequent excellent hydrogen or electron
expressed higher ONOO- scavenging activity than phenol
(Fig. 4) (Heijnen et al. 2001). Correspondingly, it was reported
that increasing the number of OH groups increased the anti-
oxidant activity (Cao et al. 1997). Secondly, the position of the
OH substitution at the conjugated ring contributes to the
antioxidant activity. Considering the one position of OH sub-
stitution, the substitution at position C-5 (Fig. 3a, 3e) exhibits
better free radical scavenging activities than the substitution at
position C-6 (Fig. 3a, f). Beyond the two position of OH
substitution, the substitution at position C-6 and C-3
(Fig. 3a, f) can decrease the antioxidant activities due to the
steric hindrance of the molecule structure (Suvarnakuta et al.
2011). Furthermore, Heijnen et al. (2001) reported that the
most negative Hammett Sigma constant as electron donating
Fig. 4 Peroxynitrite scavenging activity of monophenol and polyphenol.
effect was observed when the OH is at the o- or p-positions of IC50 stands for the concentration giving 50 % inhibition of the oxidation
conjugated ring. In contrast, positive Hammett Sigma constant of dihydrorhodamine-123 (modified from Heijnen et al. 2001)
J Food Sci Technol (December 2014) 51(12):3546–3558 3555
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