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 Food Chemistry 125 (2011) 660–664

Contents lists available at ScienceDirect

Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Phenolic composition and antioxidant activity of culms and sugarcane

(Saccharum officinarum L.) products
Joaquim Maurício Duarte-Almeida a,⇑, Antonio Salatino b, Maria Inés Genovese a, Franco M. Lajolo a
a
Departamento de Alimentos e Nutrição Experimental, FCF, Universidade de São Paulo, Av. Prof. Lineu Prestes 580, Bloco 14, CEP 05508-900 São Paulo, SP, Brazil
b
Departamento de Botânica, Instituto de Biociências, Universidade de São Paulo, C. Postal 11461, CEP 05422-970 São Paulo, SP, Brazil

a r t i c l e i n f o a b s t r a c t

Article history: The present work reports amounts of flavonoids and phenylpropanoids of culms of three sugarcane vari-
Received 14 April 2010 eties and of raw juice, syrup, molasse and VHP sugar. The antioxidant activity of those materials was eval-
Received in revised form 21 July 2010 uated by the DPPH and b-carotene/linoleic acid methods. The predominant phenolics in culms were
Accepted 15 September 2010
phenylpropanoids (caffeic, chlorogenic and coumaric acids), while flavones (apigenin, tricin and luteolin
derivatives) appeared in lower amounts. Differences were noted either among phenolic profiles of sugar-
cane culms or between culms and sugarcane products. The antioxidant activities of solutions from most
Keywords:
samples were similar or higher than a 80 lM Trolox solution.
Sugar cane products
Phenolic compounds
Ó 2010 Elsevier Ltd. All rights reserved.
Antioxidant activity
Flavonoids
Tricin
Chlorogenic acid

1. Introduction
Sugarcane (Saccharum officinarum L.) is a source not only of su-
gar and raw material for alcohol production, but also for a variety
of other products. Raw juice is a liquid with 14–16° Brix obtained
upon squeezing of the culms. Concentration of the juice to 55–65°
Brix produces sugarcane syrup. Further evaporation up to about
80° Brix leads to molasse, a dark product almost as thick as bee
honey. ‘‘Rapadura” is a hard, dark green food consumed mainly
in Brazilian rural areas, obtained by solidification of molasse. It is
similar to kokuto, a sugarcane product consumed as candies in
Japan. VHP (Very High Polarisation) sugar, a dark brown product,
is sold in the sugar market for industrial production of refined,
white sugar. VHP processing may lead either to crystal, amorphous
or granulated refined sugar (Cosan, 2002). Conventional methods
for sugar production include thermal and chemical treatment of
the juice, syrup and molasse, aiming to increase the sucrose con-
centration and pigment removal.
Pigments present in sugarcane juice are mainly phenolic com-
pounds. Paton and Duong (1992) reported the phenolic composi-
tion of sugarcane and its products. Such compounds are mainly
phenylpropanoids and flavonoids, major representatives of the
latter being derivatives of naringenin, tricin, apigenin and luteolin
(Smith & Paton, 1986; Williams, Harborne, & Clifford, 1974). Naka-
⇑ Corresponding author. Tel.: +55 11 4043 4412; fax: +55 11 5084 2793.
E-mail address: maudal@usp.br (J.M. Duarte-Almeida).
sone, Takara, Wada, Tanaka, and Yogi (1996) isolated five antioxi-
dant compounds from a kokuto extract; Takara et al. (2002)
increased the number to thirteen, including several glycosylated
phenolic compounds. Some compounds showed antioxidant activ-
ity higher than a-tocoferol. Payet, Cheong, and Smadja (2005,
2006) reported antioxidant activity by different samples of brown
sugar and suggested that some phenolic acids and flavonoids may
account for at least part of the observed activity. Phenolic sub-
stances in sugarcane juice may exert biological activities
(Duarte-Almeida, Vidal Novoa, Fallarero Linares, Lajolo, & Genov-
ese, 2006). An acylated tricin glycoside isolated from sugarcane
juice was shown to have antiproliferative activity (Duarte-Almei-
da, Negri, Salatino, Carvalho, & Lajolo, 2007).
The present work aims to analyse the phenolic composition of
culms of three varieties of sugarcane and products obtained during
sugar production, as well as the corresponding antioxidant
activities.
2. Materials and methods
2.1. Materials
Samples of sugarcane culms and sugarcane products from pro-
gressive stages of sugar production were obtained from Cosan
(Piracicaba, Brazil, a manufacturer enterprise of sugarcane prod-
ucts). Sugarcane culms analysed were of the varieties SP801842

0308-8146/$ - see front matter Ó 2010 Elsevier Ltd. All rights reserved.
doi:10.1016/j.foodchem.2010.09.059
 J.M. Duarte-Almeida et al. / Food Chemistry 125 (2011) 660–664 661

(V1), SP813250 (V2) and RB855486 (V3). Sugarcane products ana-

Total cinnamic acids

lysed were raw juice (RJ), syrup (SY), molasse (MO) and VHP sugar.

2.2. Chemicals

2.29 ± 0.01b
3.12 ± 0.00a

2.46 ± 0.07c
All chemicals used were reagent or HPLC grade. DPPH (2,2-di-

nd

nd

nd
phenyl-1-picrylhydrazyl free radical), Trolox, Tween 40, b-caro-
tene, linoleic acid, apigenin, luteolin, and coumaric acids were
purchased from Sigma–Aldrich Chemical Co. (St. Louis, MO). Caf-
feic, ferulic and chlorogenic acids were purchased from Apin

Total flavonoids
Chemicals Ltd. (Abingdon, UK). Tricin was isolated as described
elsewhere (Duarte-Almeida et al., 2007).

0.29 ± 0.03d
0.34 ± 0.02b

0.35 ± 0.01b
1.24 ± 0.01a

1.23 ± 0.00e
0.77 ± 0.00c
2.3. Extraction of phenolic substances

Extraction was performed in triplicate according to Duarte-Al-

meida et al. (2007), with slight modifications. Solid samples were
thoroughly homogenised by powdering with liquid nitrogen.

Ferulic
Duplicate samples of the fresh powder (20 g) were extracted three

nd
nd
nd
nd
nd
nd
times with methanol/water 70:30, including the water conveyed
by the samples, at speed five on a Brinkmann homogenizer (Poly-

Values with different superscript letters within the same columns are significantly different (p < 0.05; one-way ANOVA and Newman Keuls test).
tron-Kinematica GmbH, Kriens-Luzern, Sweden) for 1 min in an ice
bath. The homogenate was filtered under reduced pressure

0.59 ± 0.01b
1.41 ± 0.00a

1.21 ± 0.06c
through filter paper (Whatman No. 6). Other liquid samples were

Coumaric
extracted with methanol/water 70:30, including the volume of
water contained in the sample, at speed five for 1 min, as above.

nd

nd

nd
The solvent of the extracts were evaporated almost to dryness at
40 °C under reduced pressure on a Rotavapor RE 120 (Büchi, Flawil,
Sweden). The concentrated extracts were diluted with water to the
final volume of 25 ml.

Chlorogenic

1.11 ± 0.00b
1.52 ± 0.00a

1.60 ± 0.00a
2.4. Solid-phase extraction

nd

nd

nd
Purification of extracts, aiming to maximise phenolic contents,
was carried out by fractionation of 10 ml aliquots of the extracts
on polyamide columns (CC 6, Macherey–Nagel Gmbh and Co., Du-
Cinnamic acids

ren, Germany), soaked previously with 20 ml methanol and 60 ml

0.10 ± 0.00b
0.20 ± 0.00a

0.13 ± 0.00c
water. The columns were washed with water (20 ml) and eluted
Caffeic

with methanol (50 ml), followed by methanol/ammonia (99.5:0.5

nd

nd

nd

v/v, 50 ml). Each eluate was evaporated to dryness under reduced

pressure at 40 °C, resuspended in 1 ml methanol and filtered
Phenolic compounds contentsA of sugarcane culm varieties determined by HPLC-DAD.

through a 0.22 lm PTFE filter (Millipore Ltd., Bedford, MA) prior

to HPLC analysis and evaluation of antioxidant activities.
0.29 ± 0.03b
0.34 ± 0.02a

0.35 ± 0.01a

2.5. Analytical HPLC

Tricin

Obs: V1, SP801842; V2, SP813250; V3, RB855486; nd, Not detected.
nd

nd

nd

Data are expressed in mg/100 g as means ± SD from triplicate.

Identification and quantification of phenolic substances in the

eluates were carried out in duplicates, using analytical reversed-
phase HPLC on an Agilent 1100 system with autosampler and qua-
ternary pump coupled to a diode array detector. The column used
0.51 ± 0.00b
0.67 ± 0.00a

0.63 ± 0.00c

was a Prodigy 5 l ODS3 reversed phase silica (250  4.6 mm i.d.,

Luteolin

Phenomenex Ltd.) and elution solvents were: A, water:tetrahydro-

nd

nd

nd

furan:trifluoroacetic acid 98:2:0.1 and B, acetonitrile. Solvent gradi-

ent used was based on Duarte-Almeida et al. (2007). Identification
followed comparison of UV spectra and retention times with
authentic standards, and quantification based on external calibra-
0.26 ± 0.00b
0.56 ± 0.01a

0.60 ± 0.00c

tion. Standards used for phenylpropanoid analyses were caffeic,

Flavonoids
Apigenin

coumaric, ferulic and chlorogenic acids, and for flavones, tricin,

luteolin and apigenin. Results were expressed as mg/100 g of
nd

nd

nd

sample.

2.6. Antioxidant activity

Table 1

V1m

V2m

V3m
V1a

V2a

V3a

a,b,c,d,e

Care was taken to avoid the influence of differences in phenolic

A

concentrations among samples. After solid-phase extraction, all

662 J.M. Duarte-Almeida et al. / Food Chemistry 125 (2011) 660–664

Table 2
Phenolic compounds contentA of the sugarcane products obtained by HPLC-DAD.

Flavonoids Cinnamic acids Total flavonoids Total cinnamic acids

Apigenin Luteolin Tricin Caffeic Chlorogenic Coumaric Ferulic
RJm 1.73 ± 0.16a 0.27 ± 0.05a 0.59 ± 0.06a nd nd 0.90 ± 0.06a 0.28 ± 0.13a 2.60 ± 0.18a 1.18 ± 0.19a
RJa nd nd 1.87 ± 0.48a nd 0.51 ± 0.12a nd nd 1.87 ± 0.48a,f 0.51 ± 0.12a,d
SYm 2.31 ± 0.01a 1.05 ± 0.12b 2.15 ± 0.14a nd 2.93 ± 0.13b 5.55 ± 1.07b 1.41 ± 0.06b 5.51 ± 0.02b 9.89 ± 1.18b
SYa nd nd 3.53 ± 0.22b nd 0.77 ± 0.12a nd nd 3.53 ± 0.22a,g 0.77 ± 0.12a,d
MOm 16.82 ± 0.96b 6.35 ± 0.51c 13.23 ± 1.59c nd 24.29 ± 1.81c 23.43 ± 0.4c 7.88 ± 1.34c 36.40 ± 0.50c 55.60 ± 3.03c
MOa nd nd 26.16 ± 2.38d nd 3.29 ± 0.16b nd nd 26.16 ± 2.38d 3.29 ± 0.16d
VHPm 0.71 ± 0.10c 0.42 ± 0.01a 0.31 ± 0.11a nd 0.57 ± 0.01a 0.38 ± 0.02a 0.13 ± 0.01a 1.43 ± 0.09a,f 1.08 ± 0.04a,d
VHPa nd nd 0.46 ± 0.12a nd nd nd nd 0.46 ± 0.12e nd

Obs: RJ, raw juice; SY, syrup; MO, molasses; VHP, VHP sugar; nd, Not detected.
A
Data are expressed in mg/100 g as means ± SD from triplicate.
a,b,c,d,e,f
Values with different superscript letters within the same columns are significantly different (p < 0.05; one-way ANOVA and Newman Keuls test).

samples were diluted to the concentration of 100 lM of chlorogen- ison of relative RSA efficiency of the samples analysed. All assays
ic acid, based on estimates by HPLC analyses (Tables 1 and 2). were run in five replicates.

2.6.2. b-Carotene/linoleic acid method (b-CLAM)

2.6.1. Radical scavenging activity (RSA)
The method evaluates the antioxidant activity at inhibiting the
The method determines the activity of substances at scavenging
discolouration of b-carotene caused by free radicals yielded during
free radicals (Brand-Williams, Cuvelier, & Berset, 1995). Analyses
peroxidation of linoleic acid (Yanishilieva & Marinova, 1995). The
were carried out using the DPPH (2,2-diphenyl-1-picrylhydrazyl)
procedure used was based on Duarte-Almeida et al. (2006). Reac-
method (Brand-Williams et al., 1995; Laskar, Sk, Roy, & Begum,
tive solutions were prepared mixing 25 ll of 2 mg/ml chloroform
2010). Solutions of samples in methanol were individually added
solution of b-carotene with 20 lg linoleic acid, 200 mg Tween 40
to 0.1 mM DPPH in methanol. The mixture was incubated in the
and 0.5 ml chloroform. Chloroform was then completely evapo-
dark at 25 °C for 30 min (Duarte-Almeida, Santos, Genovese, & Laj-
rated under nitrogen flow, and 25 ml distiled water saturated with
olo, 2006). Scavenging capacity was determined by monitoring the
oxygen was added to the mixture. The absorbance was adjusted
absorbance at 517 nm. Lower absorbance indicates higher free rad-
with water to 0.6. For the oxidation reaction, 10 ll of the solutions
ical scavenging activities. The RSA percent was calculated as
of concentrated extracts were mixed with 250 ll of the b-carotene/
follows:
linoleic acid solution in a microplate. The samples were submitted
acontrol  asample to autoxidation at 45 °C for 120 min. The absorbance at 470 nm
%RSA ¼  100 was measured at time zero and at 15 min intervals using a micro-
acontrol
plate spectrophotometer (Benchmark Plus, Bio-Rad). Methanol was
where acontrol is the absorbance of the control (methanol plus used as control and Trolox (6-hydroxy-2,5,7,8-tetramethylchro-
DPPH), and asample is the absorbance of the sample plus DPPH. A man-2-carboxylic acid) as reference antioxidant. All assays were
Trolox 80 lM methanol solution was used as reference for compar- run in five replicates. Antioxidant activity of the sample was calcu-

Fig. 1. HPLC chromatograms of sugarcane syrup from solid-phase extraction by elution with methanol (a) and methanol/ammonium hydroxide (b) monitored at 370 nm.
Peaks (1) chlorogenic acid; (2) apigenin derivative; (3) luteolin derivative; (4) ferulic acid derivative; (5) coumaric acid derivative; (6) tricin derivative.
 J.M. Duarte-Almeida et al. / Food Chemistry 125 (2011) 660–664
lated as percent inhibition of oxidation versus control, using the
equation
" #
ða0sample  a120
sample Þ
%Inhibition ¼ 100  1 
ða0control  a120
control Þ
where asample and acontrol are the absorbances of sample and control
at t = 0 min and t = 120 min, respectively.
2.7. Statistical analysis
Results are expressed as means ± standard deviation. The statis-
tical analyses were carried out using Statistica version 5.0 (StatSoft
Inc., Tulsa, OK). Comparison of means of triplicate determinations,
using a significance level p < 0.05, was performed by one way anal-
ysis of variance (ANOVA). When significant differences were de-
tected, Newman-Keuls post hoc test was used to determine the
degree of statistical significance of the differences.
3. Results and discussion
3.1. Phenolic profiles of sugarcane culms and products
In the present paper, flavonoids, irrespective of being aglycones
or glycosides, are referred to by the respective aglycon. Thus, all
apigenin derivatives are designated ‘‘apigenin”. Although compris-
ing several isomers, all chlorogenic acids are designated ‘‘chloro-
genic acid”. Derivatives of caffeic and ferulic acids, conjugated or
not, are designated ‘‘caffeic” and ‘‘ferulic acid”, respectively. The
same applies to methoxycoumaric acid derivatives, irrespective
of being the o-, m- or p-isomer and being conjugated or not.
Most phenylpropanoids and flavones were obtained in the solid
phase by methanol elution. Tricin was eluted mostly with metha-
nol/ammonium hydroxide. Fig. 1 contains chromatograms of
methanol and methanol/ammonium hydroxide eluates.
Phenolic compounds in culms are predominantly cinnamic
acids (caffeic, chlorogenic and coumaric acids). Flavonoid contents
are lower, represented exclusively by flavones (apigenin, luteolin
and tricin) (Table 1). To date, only flavones have been reported
for sugarcane (Colombo, Yariwake, Queiroz, Hdjoko, & Hostett-
mann, 2005; Paton, 1978; Takara et al., 2002). Phenolic profiles dif-
fer among the culm varieties analysed. For example, contents of
coumaric acid and apigenin are much lower in V2 than in V1 and
V3 (Table 1).
Phenolic profiles differ comparing sugarcane culms and derived
products (RJ, SY, MO and VHF). A remarkable difference is the mu-
tual exclusiveness between caffeic and ferulic acids, the former
present only in culms and the latter in sugarcane products (Table
1 and 2). Seemingly, enzymatic processes take place after sugar
grinding, promoting methylation of caffeic acid from culms, giving
rise to ferulic acid in sugarcane products. Another difference is the
predominance of chlorogenic acid (a phenylpropanoid) in culms
and of tricin (a flavonoid) in sugarcane products. In addition, the
predominant flavonoid in culms is luteolin and in sugarcane prod-
ucts, tricin (Table 2).
Procedures for extraction and processing of sugarcane products
may account for some of the observed differences. RJ is produced
by grinding sugarcane culms. Thus, substances more water-soluble
tend to be washed away from culms into the juice flush. On the
other hand, extraction for chemical analysis of culms starts with
treatment of powdered material with 70% methanol, which favours
extraction of alcohol-soluble and fibre-associated phenylpropa-
noids (Pan, Bolton, & Leary, 1998). In addition, methanol probably
turns enzymes inactive (Paton, 1992) and high temperatures
aimed at accelerating concentration of solids may lead to thermal
degradation of more susceptible substances.
663
Table 3
Antioxidant activity (% inhibition) of solutions of sugarcane products containing
chlorogenic acid at 100 lM concentration.
Products RSAA b-CLAMSB
RJm 28.6 ± 0.4a
77.3 ± 1.4a
RJa 38.4 ± 0.4b 55.7 ± 2.4b
SYm 32.0 ± 0.6c 76.3 ± 1.4a,d
SYa 57.8 ± 1.2d 72.4 ± 6.0a
MOm 23.9 ± 0.6e 73.2 ± 3.8a
MOa 45.2 ± 2.6f 74,4 ± 0.5a
VHPm 32.6 ± 1.3c 85.8 ± 0.6c
VHPa 32.4 ± 1.9c 83.2 ± 1.6c,d
TroloxC 33.2 ± 2.8c 72.1 ± 3.2a
Obs.: RJ, raw juice; SY, syrup; MO, molasses; VHP, VHP sugar. Extracts m, obtained
with methanol and extracts a, obtained with methanol/ammonium hydroxide.
A
RSA, Radical Scavenging Activity.
B
b-CLAMS, b-carotene/linoleic acid method system.
C
Activity of solution of Trolox (at 80 lM for RSA and at 10 lM for b-CLAMS).
a,b,c,d,e,f
Values with different superscript letters within the same columns are
significantly different (p < 0.05; one-way ANOVA and Newman Keuls test). Data are
expressed as means ± SD from five replicates.
An increase of total solids implies higher contents of phenolic
substances: SY has more phenolic substances than RJ (p = 0.0017)
and MO has the highest values. At the latter phase, chlorogenic acid
becomes the predominant phenylpropanoid (Table 2). An inverse
relationship between browning and chlorogenic acid, some neutral
phenolic compounds and luteolin derivatives contents was previ-
ously observed (Paton & Duong, 1992). This finding suggests that
these compounds participate in the browning process, undergoing
enzymatic and oxidative reactions (Bucheli & Robinson, 1995).
Chlorogenic acid still predominates among phenylpropanoids in
VHP (Table 2). Results of Table 1 disagree with the data of Payet,
Cheong, and Smadja (2005), who reported neither chlorogenic
nor flavones in their analyses of seven samples of brown sugar.
Predominance of tricin is maintained throughout the sugar pro-
cessing (Table 2). Tricin derivatives are relatively rare in nature
(Cai, Steward, & Gescher, 2005; Harborne & Hall, 1964; Hudson,
Dinh, Kokubun, Simmonds, & Gescher, 2000) and is probably re-
lated to resistance of plants to several illnesses (Harborne & Hall,
1964; McGhie, 1993).
3.2. Antioxidant activity
3.2.1. RSA
Some eluates from sugarcane products presented activity high-
er than Trolox 80 lM (Table 3). SYa had the highest activity (57.8%
of DPPH reduction), 74% over Trolox. Other products stood out,
such as MOa (45.2%) and RJa (38.4%) (Table 3), both with values
higher than Trolox (p < 0.01). Activities of eluates RJm, SYm, VHPa
and VHPm were not distinct from Trolox. Except for VHP, a eluates
had RSA higher than m eluates from the same product (Table 3)
(p < 0.05). Eluates a of RJ, MO and SY were 35%, 89% and 80% high-
er, respectively, than the m counterparts. No significant difference
was observed between the activities of VHPa and VHPm eluates.
3.2.2. b-Carotene/linoleic acid method (b-CLAM)
Except for RJa, antioxidant activity of eluates and Trolox varied
in the range 72–85% (Table 3). Contrary to results of RSA, differ-
ences between a and m eluates were not the rule. Activities of elu-
ates RJa and RJm were significantly distinct; however, higher
activity corresponded to the m eluate (a eluates were more active
by RSA, Table 3). Activities of VHP eluates were low by RSA, but by
b-CLAM were the highest, being the only samples exceeding Trolox
activity (Table 3).
Antioxidant activity depends on many factors, such as contents
of phenolic compounds and structural details (Moure et al., 2001).
664 J.M. Duarte-Almeida et al. / Food Chemistry 125 (2011) 660–664
Phenolic substances with o-dihydroxy systems tend to be highly
active (Cuyckens & Clayes, 2004; Hopia & Heinonem, 1999).
Often no correlation is observed between results by RSA and b-
CLAM (Tsao, Yang, Xie, Sockovie, & Khanizadeh, 2005). RAS is more
selective toward hydrophilic compounds, while b-CLAM reflects
contents of lipophilic substances (Sahreen, Khan, & Khan, 2010;
Xu, Tang, Liu, Li, & Dai, 2010). For these reasons, conclusions based
only on one method may lead to underestimation of antioxidant
activities. Hence it is prudent to evaluate antioxidant activities at
least by two different methods (Tsao et al., 2005; Verhagen et al.,
2003).
4. Conclusions
Sugarcane products are appreciated as food in social-economi-
cally disfavoured areas of Brazil and other countries. Results of
the present work indicate that consumption of these products
should be encouraged. Some of them, such as ‘‘rapadura”, are
cheap sources of antioxidant substances, vitamins (A, C and D)
and minerals (Fe, Ca, P, K, Mg) (Bernal, Guzman, & Jimenez,
2004). These facts lend support to programs, now in course, aiming
to stimulate or reintroduce the use of ‘‘rapadura” as complement
food for children in elementary school.
Acknowledgements
The authors thank CNPq (Conselho Nacional para o Desenvolvi-
mento Científico e Tecnológico) and FAPESP (Fundação de Amparo
a Pesquisa de São Paulo) for financial support.
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