JFS
C: Food Chemistry and Toxicology
Effect of Seed Roasting Conditions
on the Antioxidant Activity of
Defatted Sesame Meal Extracts
ABSTRACT: Antioxidant activities of defatted sesame meal extract increased as the roasting temperature of sesame
seed increased, but the maximum antioxidant activity was achieved when the seeds were roasted at 200 °C for 60 min.
Roasting sesame seeds at 200 °C for 60 min significantly increased the total phenolic content, radical scavenging activity (RSA), reducing powers, and antioxidant activity of sesame meal extract; and several low-molecularweight phenolic compounds such as 2-methoxyphenol, 4-methoxy-3-methylthio-phenol, 5-amino-3-oxo-4hexenoic acid, 3,4-methylenedioxyphenol (sesamol), 3-hydroxy benzoic acid, 4-hydroxy benzoic acid, vanillic
acid, filicinic acid, and 3,4-dimethoxy phenol were newly formed in the sesame meal after roasting sesame seeds
at 200 °C for 60 min. These results indicate that antioxidant activity of defatted sesame meal extracts was significantly affected by roasting temperature and time of sesame seeds.
Keywords: defatted sesame meal extract; roasting conditions; antioxidant activity; phenolic compounds
Introduction
A
ntioxidants such as flavonoids, tannins, coumarins, curcumi
noids, xanthons, phenolics, and terpenoids are found in various
plant products (such as fruits, leaves, seeds, and oils) (Larson 1988).
For this reason, there is a growing interest in separating these plant
antioxidants and using them as natural antioxidants. Some components of extracts isolated from fruits and vegetables are proven as effective as synthetic antioxidants in model systems (Pratt and Hudson 1990).
Sesame (Sesamum indicum L.) seed is composed of 45% to 50%
lipid, 5% to 6% moisture, 10% to 15% carbohydrate, 5% to 6% ash,
4% to 5% fiber, and 15% to 20% protein. It is one of the most important oil seed crops in the world. Sesame seed is not only a good
source for edible oil but also is widely used in baked goods and confectionery products (Namiki 1995). Budowski (1964) noted that
sesame oil is much more stable against oxidative changes than other vegetable oils, although it contains nearly 85% unsaturated fatty
acids such as olic acid and linoleic acid (Budowski and Markely
1951). Its remarkable stability is due to the presence of sesamin,
sesamolin, sesaminol, sesamol, and ␣-tocopherol (Fukuda and
others 1986). Sesamin showed antioxidant (Yamashita and others
2000), anticarcinogenic (Hirose and others 1992), blood pressure–
lowering (Matsumura and others 1998), and serum lipid-lowering
effects (Hirose and others 1991; Hirata and others 1996; Ashakumary
and others 1999) in experimental animals and humans. The conventional process for sesame oil preparation involves cleaning, optional dehulling, roasting, grinding, and oil extraction (Fukuda and
Namiki 1988). Roasting is a key unit operation that influences color,
composition, and quality as well as oxidative stability of sesame oil
(Yen and Shyu 1989).
MS 20030701 Submitted 12/11/03, Accepted 2/10/04. Authors Jeong, S.-Y. Kim,
D.-R. Kim, and Lee are with Dept. of Food Science and Biotechnology,
Kyungnam Univ., Masan 631-701, Korea. Authors Nam and Ahn are with
Dept. of Animal Science, Iowa State Univ., Ames, IA 50011-3150. Direct inquiries to author Lee (E-mail: sclee@kyungnam.ac.kr).
© 2004 Institute of Food Technologists
Further reproduction without permission is prohibited
Defatted sesame meal (DSM) obtained from oil extraction is
mainly used as a feed ingredient for domestic animals or is composted. It has been reported that sesame oil extracted from seeds
with hulls is more stable than that extracted from dehulled seeds
(Abou-Gharbia and others 1997), indicating that antioxidant components may exist in sesame hull. Chang and others (2002) reported
that sesame coat has a significant antioxidant activity in various in
vitro systems. Feeding defatted sesame oil meal showed a hypercholesterolemic effect in rabbits (Kang and others 1999a) and promoted detoxifying capability of ethanol-medicated rats (Kang and
others 1999b).
The objective of this research was to elucidate the relationship
between roasting temperature and time on the antioxidant activity
of extract from defatted sesame meal.
Materials and Methods
Materials
White sesame seeds (Sesamum indicum L.) were purchased from
a local market in South Korea. 2-Thiobarbituric acid (TBA), tannic
acid, lard oil, and 1,1-diphenyl-2-picrylhydrazyl (DPPH) were purchased from Sigma Chemical Co. (St. Louis, Mo., U.S.A.). FolinCiocalteu reagent was from Wako Pure Chemical Industries, Ltd.
(Osaka, Japan).
Heat treatment
Whole sesame seeds (20 g) were placed in a Pyrex petri dish (8.0cm dia) and roasted in an electric muffle furnace (Model DMF-802;
Daeil Engineering, Masan, Korea) at 50 °C, 100 °C, 150 °C, or 200 °C
for 10, 20, 30, 40, 60, 90, or 120 min. After roasting, the seeds were
allowed to cool to ambient temperature before oil extraction.
Preparation of DSM and its methanolic extract
The roasted sesame seeds (20 g) were crushed, and oil was extracted using an electric oil extractor (Model Do-9001; Donga Oscar
Co., Gimhae, Korea), 1st. The remaining oil in residue was extracted
Vol. 69, Nr. 5, 2004—JOURNAL OF FOOD SCIENCE C377
Published on Web 6/15/2004
C: Food Chemistry & Toxicology
S.-M. J EONG, S.-Y. KIM, D.-R. K IM, K.C. NAM , D.U. AHN, AND S.-C. LEE
Antioxidant activity of defatted sesame meals . . .
Table 1—Effect of heat treatments with different temperatures and periods on total phenolic contents of methanol extracts
from defatted sesame meals
Roasting time (min) a
Temp (°C)
␮ M)
0 (␮
␮ M)
10 (␮
50
100
150
200
SEM
35.6d
35.6d
35.6f
35.6f
0.1
27.2fz
33.2ey
38.0ex
50.7ew
0.9
␮ M)
20 (␮
39.3bx
35.7dy
33.4gz
73.8bcw
0.4
␮ M)
30 (␮
34.9dz
39.7cy
43.5dx
72.3cdw
1.1
␮ M)
40 (␮
␮ M)
60 (␮
33.0ez
40.1cy
83.6aw
69.0dx
0.4
33.5ez
47.0ay
84.4ax
87.4aw
0.5
␮ M)
90 (␮
37.1cy
35.4dz
46.7cx
70.9cdw
0.4
␮ M)
120 (␮
SEM
40.5az
43.8 by
67.9bx
76.8bw
0.3
0.2
0.4
0.3
1.1
a Different letters (a through f) within a row indicate significant differences ( P < 0.05); n = 3. Different letters (x through w) within a column with same color
value indicate significant differences ( P < 0.05).
C: Food Chemistry & Toxicology
Table 2—Effect of heat treatments with different temperatures and periods on radical scavenging activity of methanol extracts
from defatted sesame meals
Roasting time (min) a
Temp (°C)
50
100
150
200
SEM
0 (%)
10 (%)
20 (%)
30 (%)
40 (%)
60 (%)
90 (%)
120 (%)
SEM
34.01a
34.01bc
34.01f
34.01e
0.68
26.25cz
28.88dy
31.37gx
61.49dw
0.65
35.71ax
31.35cdy
28.57hy
77.33cw
0.88
30.90bz
33.85bcy
42.85ex
79.81bw
0.53
29.35by
37.43bx
78.73bw
78.26cw
0.47
27.94bcz
44.72ay
80.59ax
82.14aw
0.59
30.44bz
34.94bcy
60.67dx
77.95cw
0.72
28.73bcz
36.80by
74.38cx
79.35bw
0.64
0.76
0.91
0.48
0.27
a Different letters (a through f) within a row indicate significant differences ( P < 0.05); n = 3. Different letters (x through w) within a column with same color
value indicate significant differences ( P < 0.05).
with 100 mL of n-hexane by vigorous shaking in a 3-cycle shaker,
filtered through a Whatman nr 1 filter paper (Whatman Int’l Ltd.,
Maidstone, England), and the residue (defatted sesame meal,
DSM) was collected and dried at room temperature.
The DSM (10 g) was extracted overnight with 100 mL of methanol in a shaking incubator at room temperature and filtered through
Whatman nr 1 filter paper. The residue was re-extracted under the
same conditions. The 1st and 2nd extracts were pooled and filtered
through Whatman nylon membrane filter (0.2-␮m, Millipore filtration kit MA 01730, Millipore Co., Bedford, U.K.). The methanol in
the filtrate was evaporated under vacuum at 40 °C using a rotary
evaporator (Model Eyela N-1000; Tokyo Rikakikai Co., Tokyo, Japan).
The dried methanolic extract of DSM was redissolved in methanol
(1 mg/mL) and used for further analyses.
Total phenolic content
The total phenolic content (TPC) of DSM extracts was determined using the method by Gutfinger (1981). The DSM extract (1 mL,
1 mg/mL) was mixed with 1 mL of 50% Folin-Ciocalteu reagent and
1 mL of 2% Na2CO3, and centrifuged at 13400 ⫻ g for 5 min. The
absorbance of upper phase was measured using a spectrophotometer (Model UV-1601; Shimadzu, Tokyo, Japan) at 750 nm after 30
min incubation at room temperature. TPC was expressed as a tannic acid equivalent.
DPPH radical scavenging activity
The effect of extracts on DPPH radical scavenging activity was
estimated using the method of Blois (1958). After mixing 1 mL of
0.041 mM DPPH in ethanol with 0.2 mL of DSM extract (1 mg/mL)
for 10 min, the absorbance was measured at 517 nm. Radical scavenging activity was expressed as the inhibition percentage and was
calculated using the following formula:
% DPPH radical scavenging activity =
(1 – sample absorbance/control absorbance) ⫻ 100
C378
JOURNAL OF FOOD SCIENCE—Vol. 69, Nr. 5, 2004
Reducing power
The reducing power of DSM extract was determined according
to the method of Oyaizu (1986). The DSM extract (1 mL, 1 mg/mL),
phosphate buffer (1 mL, 0.2 M, pH 6.6), and potassium ferricyanide
(1.0 mL, 10 mg/mL) were mixed and incubated at 50 °C for 20 min.
Trichloroacetic acid (1.0 mL, 100 mg/mL) was added to the mixture
and centrifuged at 13400 ⫻ g for 5 min. The supernatant (1.0 mL)
was mixed with distilled water (1.0 mL) and ferric chloride (0.1 mL,
1.0 mg/mL), and then the absorbance was measured at 700 nm.
Rancimat method
The induction periods of lard as affected by the addition of antioxidant were determined according to the method of Chen and Ho
(1997). A Metrohm 793 Rancimat instrument (Herisau, Switzerland)
was used to determine the oxidation of lard with or without addition of sesame meal extract. Oxidation was induced at 120 °C with
air at a flow rate of 20 L/h. One milliliter of each sample (10 mg/mL)
was added to the lard (2.5 g) and then mixed vigorously with vortex
for 8 s immediately before starting the Rancimat measurement.
Composition of defatted sesame meals extract
Each DSM extract from unroasted control or roasted at 200 °C for
60 min was dissolved in ethanol (200 mg/mL) and centrifuged at
13400 ⫻ g for 5 min to precipitate undissolved materials. Analysis
was carried out with or without derivatization. Derivatization was
done by mixing DSM extract with 4 volumes of N,Obis(trimethylsilyl)acetamide (BSA) and incubating in a water bath
(70 °C) for 15 min (Du and Ahn 2002). The compounds in the DSM
extract were identified using gas chromatography-mass spectrometry (Model GC6890/MS5973; Hewlett-Packard Co., Wilmington,
Del., U.S.A.). A split inlet (100:1) was used to inject samples (5 ␮L)
into an HP-5 column (30 m, 0.32-mm inner dia, 0.25 ␮m film;
Hewlett-Packard Co.). A ramped oven temperature was used
(100 °C for 2 min, increased to 270 °C at 10 °C/min, and held for 6
min). The inlet temperature was 250 °C and the carrier gas was He
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Antioxidant activity of defatted sesame meals . . .
Table 3—Effect of heat treatments with different temperatures and periods on reducing power of methanol extracts from defatted sesame meals
Roasting time (min) a
Temp.
(°C)
50
100
150
200
SEM
0
10
20
30
40
60
90
120
Absorbance at 700 nm
0.182e
0.182f
0.182g
0.182f
0.004
0.169fz
0.265ax
0.208fy
0.346ew
0.003
0.193cdy
0.186fy
0.230ex
0.510dw
0.008
0.248by
0.198ez
0.381cx
0.571bw
0.004
0.199cy
0.201ey
0.622aw
0.577bx
0.006
a Different letters (a through f) within a row indicate significant differences ( P < 0.05);
SEM
0.189dz
0.248by
0.615ax
0.660aw
0.005
0.200cz
0.229cy
0.340dx
0.535cw
0.004
0.259ay
0.215dz
0.454bx
0.580bw
0.003
0.002
0.003
0.007
0.006
n = 3. Different letters (x through w) within a column with same color
Table 4—Induction time of lipid peroxidation of different methanol extracts from defatted sesame meals
Roasting time (min)
Temp.
(°C)
50
100
150
200
SEM
Control
0
10
20
30
40
60
90
120
Induction time (min)
0.18b
0.18c
0.18d
0.18d
0.01
0.74a
0.74b
0.74c
0.70c
0.02
0.72a
0.7b
0.71c
0.85bc
0.05
0.73ax
0.71bxy
0.67cy
0.88abcw
0.02
0.70ax
0.72bx
0.70cx
0.97abw
0.02
0.71ax
0.74bx
1.04aw
0.98abw
0.03
a Different letters (a through f) within a row indicate significant differences ( P < 0.05);
SEM
0.74ax
0.86ax
1.02aw
1.09aw
0.04
0.77ax
0.73bx
0.75cx
0.96abw
0.03
0.76ax
0.79abx
0.85bx
1.00abw
0.04
0.02
0.03
0.03
0.05
n = 3. Different letters (x through w) within a column with same color
value indicate significant differences ( P < 0.05).
at constant flow of 1.5 mL/min. The ionization potential of the mass
selective detector was 70 eV and the scan range was 19.1 to 400 m/
z. Identification of compounds was achieved by comparing mass
spectral data of samples with those of the Wiley library (HewlettPackard Co.).
Statistical analysis
All measurements were done in triplicate with 3 different samples, and the analysis of variance was conducted by the procedure
of the General Linear Model, using SAS Inst. (1995) software. Student-Newman-Keul’s multiple range tests were used to compare the
significant differences of the mean values of treatments (P < 0.05).
Results and Discussion
Effects of seed roasting conditions on the antioxidant
activities of DSM extract
Phenolic compounds are known to act as antioxidants not only
because of their ability to donate hydrogen or electrons but also
because they are stable radical intermediates, which prevent various food ingredients from oxidation (Cuvelier and others 1992;
Maillard and others 1996). The TPC in methanolic extract of DSM
increased significantly as the roasting temperature increased (Table 1). The amount of total phenolics in the extract of sesame meal
increased from 35.6 ␮M in unroasted control to 87.4 ␮M in 200 °C, 60
min roasting.
Kim (2000) reported that the storage stability of unroasted sesame oil was low, but roasting of sesame seed at 170 °C or higher significantly increased the stability of sesame oil. The highest sesamol
content and storage stability of sesame oil was accomplished when
sesame seeds were roasted at 200 °C to 220 °C. Yoshida and Takagi
(1997) also reported that sesamol, a potent phenolic antioxidant,
increased as the roasting temperature of sesame seeds increased
to 180 °C or higher. Our results indicated that roasting of sesame
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seeds cleaved and liberated phenolic compounds (Table 1). However, our previous study (Lee and others 2003) showed that simple
heat treatment could not cleave covalently bound phenolic compounds from rice hull while far-infrared treatment could. This indicates that the effective processing step for liberating antioxidant
compounds from plants should be different depending on species.
The DPPH radical scavenging activities of DSM extract significantly increased with roasting time at 150 °C and 200 °C (Table 2).
The radical scavenging activities of DSM extracts increased from
34.01% to 80.59% after treating them at 150 °C for 60 min, and from
34.01% to 82.14% after 200 °C for 60 min. Roasting sesame seeds at
50 °C or 100 °C, however, did not change the radical scavenging
activity of DSM extracts significantly. Roasting sesame seeds between 160 °C and 200 °C increased the stability of sesame oil.
The antioxidant power of certain compounds is associated with
reducing power (Jayaprakasha and others 2003). Duh (1998) reported that the reducing properties of antioxidants are generally associated with the presence of reductones. The reducing power of DSM
extract increased from 0.182 to 0.622 (absorbance value) with 150 °C,
40 min heat treatment, and from 0.182 to 0.660 with 200 °C, 60 min
heat treatment (Table 3). With 50 °C or 100 °C heat treatment, the
reducing power of DSM extract was not increased significantly.
The Rancimat method is commonly used to evaluate antioxidant
potency of various antioxidants (Chen and Ho 1995). The longer the
induction period of lard, the better is the antioxidant activity of the
compound. The induction time of lard increased from 0.74 to 0.86 h
when the extract from sesame seeds roasted at 100 °C for 60 min was
added and from 0.74 to 1.04 h when 150 °C, 40 min was used. The
highest inhibiting effect of DSM extract was observed when the seeds
were roasted at 200 °C for 60 min (Table 4). Thus, antioxidant effect
of DSM extract depends upon roasting temperature and time.
Identification of DSM extracts
Several low-molecular-weight phenolic compounds such as pVol. 69, Nr. 5, 2004—JOURNAL OF FOOD SCIENCE
C379
C: Food Chemistry & Toxicology
value indicate significant differences ( P < 0.05).
Antioxidant activity of defatted sesame meals . . .
Table 5—Characteristic ions present in the mass spectra of defatted sesame meal extracts unroasted and roasted at 200 °C
for 60 min
Compound
C: Food Chemistry & Toxicology
Retention time (min)
Identified ions (m/z)
Match quality (%)
19.54
7.33
7.69
13.26
15.37
43, 57, 71, 73, 85, 338
73, 136, 151, 166, 181, 196
42, 69, 75, 100, 170
43, 73, 117, 129, 147, 177, 193, 223
73, 84, 126, 165, 193, 223, 253, 397
94
97
38
90
97
9.47
9.96
12.40
13.26
15.38
24.90
77, 107, 135, 150
39, 52, 69, 80, 107, 117, 138, 254
73, 116, 129, 147, 193, 223, 267, 282
73, 84, 147, 158, 177, 195, 267, 282
73, 84, 165, 193, 253, 267, 297, 312
42, 55, 69, 93, 111, 139, 154
90
95
89
70
93
48
BSA-derivatized a
Ferulic acid
2-Methoxy phenol
4-Methoxy-3-methylthio phenol
4-Hydroxy benzoic acid
Vanillic acid
Non-derivatized
4-Vinyl-2-methoxy phenol
3,4-Methylenedioxy phenol
3-Hydroxy benzoic acid
4-Hydroxy benzoic acid
Vanillic acid
3,4-Dimethoxy phenol
a Identified as trimethylsilyl (TMS) derivatives.
hydroxybenzoic acid, p-coumaric acid, and vanillic acid were detected in the methanolic extracts of DSM (Table 5). In addition to sesamol and tocopherols, many other antioxidant compounds such as
polyphenol compounds are present in sesame seeds and its defatted sesame meals (Fukuda and others 1981). Fenton and others
(1980) reported that polyphenol compounds such as caffeic, p-coumaric, ferulic, p-hydroxybenzoic, sinapic, trans-cinnamic, and chlorogenic acids were present in the hydrolysate of rapeseed meal.
The sesame seed extracts from unroasted and roasted (at 200 °C
for 60 min) after BSA derivatization showed significant differences
in kinds and amounts of phenolic compounds (Figure 1): ferulic
acid was detected only in unroasted DSM extracts whereas 2-methoxyphenol, 4-methoxy-3-methylthio-phenol, 4-hydroxy benzoic
acid, and vanillic acid were detected only in roasted DSM extracts.
In addition, under nonderivatized conditions, a significant amount
of 3,4-methylenedioxyphenol (sesamol), a well-known antioxidant
phenolic compound, was detected in roasted DSM extract samples. Although species of detected compounds may be different by
derivatization, it is clear that roasting of sesame seeds helped liberating phenolic compounds from DSM.
Phenolic acids and their derivatives are widely distributed in
plants (Deshpande and others 1984). A number of phenolic acids
are linked to various cell wall components such as carbohydrate and
protein molecules (Harris and Hartley 1976; Hartley and others
1990). It was reported that 75.3% of phenolic compounds in DMS
was present as soluble esters and 24.7% as insoluble residue (Dabrowski and Sosulski 1984). In nature, low-molecular-weight phenolic compounds present as bound form in plants have little antioxidant activities (Niwa and others 1991). Liberated forms of phenolic
compounds by far-infrared radiation (Niwa and Miyachi 1986; Niwa
and others 1998) or gastric juices (Niwa and others 1991) show
strong antioxidant activities.
Conclusions
Figure 1—Typical gas chromatograms of defatted sesame
meal extracts, unroasted (A) and roasted (B) at 200 °C for
60 min after BSA derivatization. Peaks in (A) are 1: 3,7dioxa-2, 8-disilanonane; 2: tricosane; 3: D-glucitol; 4:
eicosane; 5: 2-azathianthrene; 6: a-D-glucopyranose; 7:
inositol; 8: palmitic acid; 9: oleic acid; 10: linoleic acid;
11: ferulic acid; 12: 1H-indole-1-acetic acid; 13: linoleic
acid; and 14: stearic acid. Peaks in (B) are 1: 3hydroxypyridine; 2: 2-methoxyphenol; 3: 4-methoxy-3methylthio-phenol; 4: 5-oxo-1-hydroxy L-proline; 5: 5-amino3-oxo-4-hexenoic acid; 6: 4-hydroxy benzoic acid; 7: 2azathianthrene; 8: levoglucosan; 9: galactofuranoside; 10:
vanillic acid; 11: glutamine; 12: glucofuranoside; 13: palmitic acid; 14: b-D-galactofuranoside; 15: 1H-indole-1-acetic acid; and 16: linoleic acid.
C380
JOURNAL OF FOOD SCIENCE—Vol. 69, Nr. 5, 2004
A
lthough simple heat treatment is not effective in cleaving co
valently bound phenolic compounds from seeds, heat treatment is highly effective in converting insoluble phenolic compounds to soluble forms. To obtain the highest antioxidant activity
from defatted sesame meal extracts, sesame seeds should be roasted at 200 °C for 60 min.
Acknowledgments
This study was supported by the Ministry of Science and Technology (MOST) and the Korea Science and Engineering Foundation
(KOSEF) through the Coastal Resource and Environmental Research
Center (CRERC) at Kyungnam Univ. (R12-1999-025-10001-0), Korea,
and State of Iowa Funds. Seok-Moon Jeong and So-Young Kim reURLs and E-mail addresses are active links at www.ift.org
ceived scholarships from the Brain Korea 21 Program of the Korean
Ministry of Education.
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