JFS C: Food Chemistry and Toxicology

Oregano and Rosemary Extracts

Inhibit Oxidation of Long-Chain
n-3 Fatty Acids in Menhaden Oil
S.D. BHALE, Z. Xu, W. Prinyawiwatkul, J.M. King, AND J.S. GODBER
C: Food Chemistry & Toxicology

ABSTRACT: Capabilities of methanol extracts from oregano and rosemary in retarding oxidation of long-chain
polyunsaturated fatty acids, docosahexaenoic acid C22:6 (DHA) and eicosapentaenoic acid C20:5 (EPA), in men-
haden oil were investigated. The fish oils after mixing with the extracts at different concentrations were oxidized in
an accelerated study by heating at 150 ◦ C for 30 min or incubating at 60 ◦ C for 5 d. After heating at 150 ◦ C, only 15.9%
of DHA and 18.5% of EPA remained in the fish oil without extract, while 38.8% to 65.9% of DHA and 44.7% to 69.0%
of EPA were retained in the fish oil mixed with 1% to 5% of oregano extract. The highest retained DHA (56.9%) and
EPA (58.0%) in the fish oils mixed with rosemary extract were observed at 2.5% addition. Increasing rosemary ex-
tract to 5% lowered its capability of inhibiting DHA and EPA oxidation. After incubation at 60 ◦ C for 5 d, the highest
inhibition capability was also found at 2.5% of added rosemary extract, and the oil retained 88.2% DHA and 88.3%
EPA. However, only 18.8% DHA and 23.6% EPA were retained in the fish oil mixed with 5% of oregano extract and no
DHA and EPA were detected in the fish oil without extract after 5-d incubation at 60 ◦ C. Thus, antioxidant activity
of the rosemary extract was greater than that of oregano extract, but was sensitive to heat. The rosemary extract
also demonstrated higher DPPH (2,2 -diphenyl-1-picrylhydrazyl) free radical scavenging capability, which was ap-
proximately 3 times higher than oregano extract, although there was no significant difference in the total phenolic
contents between both extracts.
Keywords: antioxidant, fish oil, menhaden, oregano, oxidation, rosemary

Introduction Kikuzaki and Nakatani (1993) found that the spices like ginger and

C ulinary herbs have been grown and used for hundreds of years.
They are becoming increasingly popular in the United States
for their ability to enhance and complement the flavors of vari-
turmeric in the Zingiberaceae family have higher antioxidant ac-
tivity than synthetic α-tocopherol. As consumers are increasingly
more conscious about the use of synthetic antioxidants due to tox-
ous foods (Shan and others 2005). The herbs are used for not only icological concerns, natural antioxidants from plants such as herbs
for their savory and aromatic characteristics but also for medicinal and vegetables are increasingly of interest to the food industry.
benefits such as antioxidant activity, anti-inflammatory, and an- Fish oil comprises long-chain unsaturated fatty acids (PUFA)
timicrobial, and for their ability to stimulate digestive action (Shansuch as eicosapentaenoic acid (EPA) and docosahexaenoic acid
and others 2005). Several studies have confirmed that leafy spices (DHA). Numerous studies have concluded that fish oil can reduce
such as rosemary, sage, oregano, basil, parsley, and thyme show risk factors associated with degenerative diseases, including can-
strong antioxidant activity (Hirasa and Takemasa 1998; Hinneb- cer, cardiovascular disorders, and other inflammatory conditions
urg and others 2006). Frankel (1999) demonstrated that rosemary (Perez-Mateos and others 2004). However, omega-3 PUFAs in fish
extracts contain a large number of phenolic compounds, includ- oil are readily oxidized to produce off- or rancid-flavor volatiles
ing carnosic acid, carnosol, and rosmarinic acid. The rosmarinic when exposed to light, oxygen, prooxidants, and high temperatures
acid and other phenolic compounds were found in the leaves of (McClements and Decker 2000). Thus, the quality of fish oil or foods
oregano as well (Kikuzaki and Nakatani 1993; Almeida and Regit- fortified with fish oil usually deteriorates rapidly without any stabi-
ano 2000). Kahkonen and others (1999) have also reported that phe- lizing treatments. The instability of omega-3 PUFAs during process-
nolic compounds found in spice herb plants are mainly responsi- ing and storage is becoming a serious hurdle for developing fish
ble for the biological effects such as antioxidant potential. Phenolicoil-based functional foods. Synthetic antioxidants such as EDTA,
compounds exhibit antioxidant properties through various possi- BHA, and BHT can be added to retard fish oil oxidation, but antioxi-
ble mechanisms such as free-radical scavenging activity, transition- dants from natural sources may be used to replace synthetic antiox-
metal-chelating activity, and/or singlet-oxygen-quenching capac- idants in preventing fish oil oxidation. This would not only prevent
ity (Shan and others 2005). Antioxidant activities of plant extracts omega-3 fatty acid oxidation but also enhance the health benefits
could be used to retard or prevent lipid oxidation in a variety of of the foods by having the additional health promoting bioactivity
food products (Birch and others 2001; Rababah and others 2004). from the herbs or spices.
In the present study, antioxidant capabilities of oregano and
rosemary methanol extracts in preventing DHA and EPA oxida-
MS 20070347 Submitted 5/9/2007, Accepted 7/16/2007. Authors are with ◦ ◦
Dept. of Food Science, Louisiana State Univ. Agricultural Center, Ba- tion in menhaden oil at 150 C heating and 60 C incubation were
ton Rouge, LA 70803, U.S.A. Direct inquiries to author Xu (E-mail: evaluated. The total phenolic contents and DPPH (2,2 -diphenyl-
zxu@agctr.lsu.edu). 1-picrylhydrazyl) free radical scavenging activities of the extracts

C504 JOURNAL OF FOOD SCIENCE—Vol. 72, Nr. 9, 2007 

C 2007 Institute of Food Technologists
doi: 10.1111/j.1750-3841.2007.00569.x
Further reproduction without permission is prohibited
Oregano and rosemary retard FA oxidation . . .

were measured. This information would be helpful in the develop- where Abst 0 min was the absorbance of DPPH at zero time and
ment and utilization of oregano and rosemary as a natural antioxi- Abst 30 min was the absorbance of DPPH after 30 min of incubation.
dant to be applied in fish oil or fish oil fortified foods. The inhibition percentage of the absorbance of DPPH was plot-
ted against each quantity of the extract solution to obtain a re-
gression line. Trolox (0.5 mM) in methanol was used as a stan-
Materials and Methods
dard to convert the inhibition capability of the extract solution
to the Trolox equivalent antioxidant activity. The ratio between
Chemicals
the slopes of the regression lines of the extract solution and the
Rosemary and oregano plants were obtained from the Dept.
Trolox solution was defined as the Trolox equivalent antioxidant
of Horticulture, Louisiana State Univ., Baton Rouge, La. Men-
activity.
haden oil was purchased from Sigma Aldrich Co. (St. Louis, Mo.,
◦
U.S.A.) and stored at –80 C before use. Methanol was HPLC
grade and purchased from Fisher Scientific Inc. (Fair Lawn, N.J., Fish oil preparation and accelerated oxidation
U.S.A.). BCl 3 -methanol and 2, 2-dimethoxypropane were pur- (heating and incubation) experiments

C: Food Chemistry & Toxicology

chased from Supelco (Bellefonte, Pa., U.S.A.). DPPH (2, 2 -diphenyl- The oregano or rosemary extract was homogenized with men-
1-picrylhydrazyl), Folin–Ciocalteau reagent, heptadecanoic acid haden oil at 0% (control), 1%, 2.5%, and 5% (w/w) using an ultra-
(C17:0), docosahexaenoic acid C22:6 (DHA), and eicosapentaenoic sonic distributor (60 Sonic Dismembrator; Fisher Scientific Inc.).
acid C20:5 (EPA) standards were from Sigma-Aldrich Co. Then, the oils were sampled twice to determine their initial (0 d)
DHA and EPA concentrations.
For the heating experiment, 0.5 g of the fish oils with or with-
Extraction
out extract was added into two 15-mL test tubes. Then, the test
Oregano and rosemary leaves were freeze-dried for 48 h and
tubes were immersed in a 150 ◦ C sand bath for 30 min. For the
ground to pass through a Nr. 40 sieve (0.425 mm). The ground pow-
incubation experiment, 0.5 g of the fish oil with or without ex-
ders were stored at 4 ◦ C before extraction. Ten grams of each ground
tract was added into eight 15-mL test tubes. The test tubes were
powder was weighed and extracted with 100 mL of methanol for 2 h
wrapped with aluminum foil and placed in a 60 ◦ C incubator. Two
at 30 ◦ C. The methanol supernatant was separated by centrifuging
tubes of each group, with or without extract, were taken after 1,
at 1500 × g for 15 min. The residual was re-extracted with 50 mL
2, 3, and 5 d of incubation. Each experiment was conducted in
of methanol for 2 h. The supernatant was separated using the cen-
triplicate.
trifugation and combined with the previous extract. The oregano or
rosemary extract was obtained after all methanol solvent was evap-
orated at 30 ◦ C using a centrifuge vacuum evaporator (CentriVap Determination of DHA and EPA in fish oil using GC
Mobile System; Labconco, Kansas City, Mo., U.S.A.). One hundred microliters of the fish oils were added to each test
tube (13 ×100 mm) to which 1 mL of heptadecanoic acid (C17:0) (1
mg/mL hexane) was added as an internal standard. After adding 2
Determination of total phenolic compound content mL of BCl 3 -methanol and 1 mL of 2,2 -dimethoxypropane, all test
The total phenolic content in the extracts was determined us- tubes were capped and incubated in a 60 ◦ C water bath for 10 min
ing the Folin–Ciocalteau reagent (Velioglu and others 1998). Folin– to perform the derivatization of fatty acid methyl esters. Then, 1
Ciocalteau reagent was diluted 10 times with deionized water. The mL of hexane and 1 mL of water were added to the tubes and vor-
extract (50 mg each) was dissolved in 10 mL methanol and 0.1 mL texed for 30 s. The upper hexane layer was transferred to another
of this solution was mixed with 0.75 mL diluted Folin–Ciocalteau tube, dried with anhydrous sodium sulfate, and transferred to a GC
reagent. The reaction was carried out at 25 ◦ C for 5 min. Then vial.
0.75 mL of sodium bicarbonate solution (60 g/L) was added. The A gas chromatograph (Hewlett Packard 5890, Agilent Technolo-
mixture was incubated at 25 ◦ C for 90 min and filtered through a gies, Palo Alto, Calif., U.S.A.) with an FID detector was used to de-
0.45 µm syringe filter (Pall Corp., Ann Arbor, Mich., U.S.A.). The termine DHA and EPA concentration. Helium was used as a carrier
absorbance of the filtered solution was determined at 750 nm us- gas with a column flow rate of 1.2 mL/min. The injection volume
ing a UV-Visible SpectraMax Plus384 spectrophotometer (Molecu- was 5 µL and the split ratio was 1:100. The injector and detector
lar Devices, Sunnyvale, Calif., U.S.A.). Catechin was used to prepare temperature was 250 and 270 ◦ C, respectively. The oven tempera-
a standard curve. The total phenolic content of the extract was cal- ture program was set to hold at 50 ◦ C for 3 min and then increased
culated and expressed as µg catechin equivalent/gram of freeze- at 4.0 ◦ C/min to 250 ◦ C. The column was a Supelco SP2380 (30 m ×
dried extract. 0.25 mm) (Bellefonte, Pa., U.S.A.). The concentrations of DHA and
EPA were calculated using the C17:0 internal standard as a ref-
Determination of antioxidant activity using erence. The percentages of retained DHA or EPA after heating or
the DPPH free radical scavenging method incubation were obtained by comparing the concentration in the
The extract solution for the DPPH test was prepared by dissolv- heated or incubated sample to its corresponding initial (or day 0)
ing 0.20 g of each extract in 10 mL methanol. The concentration of concentration.
DPPH solution was 0.025 g in 1000 mL of methanol. Two milliliters
of the DPPH solution were mixed with 40, 80, and 120 µL of the Statistical analysis
extract/methanol solution and transferred to a cuvette. The reac- The total phenolic content and DPPH free radical scavenging ca-
tion solution was monitored at 515 nm for 30 min at 25 ◦ C using a pability tests were carried out in triplicate. The heating and incuba-
UV-Visible SpectraMax Plus384 spectrophotometer (Molecular De- tion experiments were performed 3 times with freshly prepared fish
vices). The inhibition percentage of the absorbance of DPPH solu- oil each time. In each experiment, the results of 2 samples were av-
tion was calculated using the following equation: eraged to obtain the data at that condition. All data were analyzed
using analysis of variance (ANOVA) followed by the adjusted Tukey’s
Inhibition% = [(Abst0 min − Abst30 min )/Abst0 min ] × 100 test at P < 0.05.

Vol. 72, Nr. 9, 2007—JOURNAL OF FOOD SCIENCE C505

 Oregano and rosemary retard FA oxidation . . .
Results and Discussion
Total phenolic contents and DPPH free radical
scavenging capabilities of the extracts
The extraction yields of oregano and rosemary using methanol
as a solvent were 8.4% and 27.0% based on freeze-dried weight.
Hinneburg and others (2006) reported that the extraction yields
were from 8.8% to 25.8% for culinary herbs by using hydrodistil-
lation method. The total phenolic contents in oregano and rose-
mary extracts were similar, 58.1 and 59.2 µg catechin equivalent/g,
respectively (Table 1). Phenolic compounds in spicy vegetables
are one of the important factors responsible for the antioxidant
property (Hinneburg and others 2006; Sun and others 2007). In a
C: Food Chemistry & Toxicology
previous study, total phenolic content in the extract obtained by
methanol was usually much higher than that in the extract pro-
duced by hexane or acetone due to the higher polarity of pheno-
lic compounds (Sun and others 2006). Although the total pheno-
lic contents of oregano and rosemary extracts are not significantly
different, the free radical scavenging capability of rosemary extract
was significantly higher than that of oregano extract (Table 1). The
DPPH free radical scavenging capabilities of oregano and rosemary
extracts were 0.18 and 0.60 µmol Trolox equivalent/g, respectively.
The DPPH test has been used for evaluating antioxidant activity of
the extracts from sweet bell peppers and culinary herbs and spices
(Hinneburg and other 2006; Tiwari and others 2006; Sun and oth-
ers 2007). The DPPH free radical scavenging capabilities of different
colored sweet bell extracts were 2.1 to 3.9 µmol Trolox equivalent/g
(Sun and others 2007). In the study of Hinneburg and others (2006),
the extracts from basil and parsley exhibited antioxidant activity
in different lipid oxidation models and their activity was approxi-
Table 1 --- Total phenolic content and DPPH free radical levels of oregano and rosemary extracts were significantly different
scavenging capability of the oregano and rosemary ex- (Figure 2). The 2 extracts demonstrated significant capabilities in
tracts.
Oregano
Total phenolic content (µg catechin 58.1a
equivalent/g)
DPPH free radical scavenging capability 0.18a
(µmol Trolox equivalent/g)
Means in each row with different letters are significantly different (P < 0.05). extract and retained 38.8%, 57.6%, and 65.9% of DHA and 44.7%,
C506 JOURNAL OF FOOD SCIENCE—Vol. 72, Nr. 9, 2007
mately 16 and 400 times lower than pure gallic acid in the DPPH
free radical scavenging test, respectively.
Higher antioxidant activity has been positively correlated with
the concentration of phenolic compounds in extracts (Bryngelsson
and others 2002; Sun and others 2006; Sun and others 2007). How-
ever, in this study, the free radical scavenging capabilities between
the 2 extracts were about 3-fold different, even though no differ-
ence was found in their total phenolic contents (Table 1). Similarly,
no significant correlation between the DPPH free radical scaveng-
ing capability and total phenolic content was observed in the study
of Henneburg and others (2006). It should be especially noted that
in their study, the parsley extract with lower total phenolic content
exhibited higher activity in scavenging DPPH free radical. Thus,
the difference in antioxidant activity between oregano and rose-
mary extracts may be largely due to the different types of phenolic
compounds present in the extracts, but not the absolute amount of
phenolics. It was reported that antioxidant capability of rosemary
extract was due to rosmarinic acid, which is a flavonoid with high
antioxidant activity (Loliger 1983). Almeida and Regitano (2000) re-
ported the presence of thymol and carvacrol phenolic acids and
terpene derivatives in oregano may be responsible for its antioxi-
dant activity. Shahidi and Wanasundara (1992) suggested that an-
tioxidant capacity of substances may not be solely characterized by
the total phenolic content without consideration of the presence
and abundance of specific phenolic components and their particu-
lar structural characteristics.
Inhibition of DHA and EPA oxidation
in menhaden oil during heating
A chromatogram of EPA, DHA, and IS in menhaden oil without
heating is shown in Figure 1. After heating at 150 ◦ C for 30 min,
the retained DHA and EPA in menhaden oil mixed with different
retarding DHA and EPA oxidation during heating. Without any ex-
Rosemary tract, DHA and EPA in menhaden oil decreased to below 15.9% and
59.2a 18.5% of initial concentration after 30 min of heating, respectively.
The oxidation inhibition capability of oregano extract increased
0.60b significantly with increasing extract concentration (Figure 2). The
oregano extract had higher antioxidant capacity than the rosemary
Figure 1 --- The chromatogram of
fatty acids in the menhaden oil
used in this study.
Oregano and rosemary retard FA oxidation . . .

61.6%, and 69.0% of EPA at 1%, 2.5%, and 5% of added concentra-
tion. Oregano extract was also found to be effective against lipid ox-
idation in lard and oils with less unsaturated fatty acids (Economou
and others 1991). In their study, oregano extract was the most effec-
tive in stabilizing lard at added concentrations of 0.01% to 0.25% at
75 ◦ C storage temperature compared with dittany, thyme, marjo-
ram, spearmint, lavender, and basil extracts. In the fish oils mixed
with rosemary extract, 20.8%, 56.9%, and 45.8% of DHA and 25.0%,
58.0%, and 46.9% of EPA were retained at added concentration
of 1%, 2.5%, and 5%, respectively. Rosemary extract was reported
to have strong antioxidant activity for food lipids (Hirasa and
Takemasa 1998).
In this study, an interesting phenomenon was that the antiox-
be more complicated. Other compounds in the rosemary extract
could have prooxidant effects and suppress its antioxidant capa-
bility when the extract concentration increases to certain levels.
For example, carotenoids abundant in leafy plants are antioxidant
but not stable in the presence of oxygen and are oxidized to pro-
oxidants, hydroperoxide compounds, due to their long conjugated
polyene backbone (Subagio and Morita 2001). High heating tem-
perature may significantly affect the stability of those antioxidants
in the rosemary extract. Tiwari and others (2006) found that higher
temperatures may be related to degradation of the antioxidants in
spicy vegetable extracts and caused decreases in the antioxidant ac-
tivity. However, Shobana and Naidu (2000) studied the stabilities of
antioxidant activity of ginger, garlic, pepper, and cinnamon, and

C: Food Chemistry & Toxicology

idant capacity of rosemary extract did not increase with increas- found that they were heat stable in the temperature range of 105
ing extract concentration, particularly from 2.5% to 5%. Compared to 165 ◦ C. The heat stabilities of antioxidants in plant tissue ma-
with the oregano extract, the composition of rosemary extract may trix and extract could be different. The antioxidants in extract may

Figure 2 --- The percentages

of retained DHA and EPA in
menhaden oils added with
different concentrations of
oregano and rosemary
extracts after heating at
150 ◦ C for 30 min. Bars
with different letters are
significantly different
(P < 0.05).

0% 1% 2.5% 5% 0% 1% 2.5% 5% Figure 3 --- The percentages

of retained DHA and EPA in
100 100.0 menhaden oils with
different concentrations of
oregano extract added
80 80.0 during incubation at 60 ◦ C.
Retained EPA (%)
Retained DHA (%)

60 60.0

40 40.0

20 20.0

0 0.0
0 1 2 3 4 5 0 1 2 3 4 5
Day Day

0% 1% 2.5% 5% 0% 1% 2.5% 5% Figure 4 --- The percentages

of retained DHA and EPA in
100.0 100.0 menhaden oils with
different concentrations of
rosemary extract added
80.0 80.0 during incubation at 60 ◦ C.
Retained EPA (%)
Retained DHA (%)

60.0 60.0

40.0 40.0

20.0 20.0

0.0 0.0
0 1 2 3 4 5 0 1 2 3 4 5
Day Day

Vol. 72, Nr. 9, 2007—JOURNAL OF FOOD SCIENCE C507

 Oregano and rosemary retard FA oxidation . . .

be quickly exposed to heat and oxygen and decompose at a faster higher than that of oregano extract. Thus, for food preservation pur-
rate during heating than when they are dispersed and protected by poses, rosemary extract may be more effective than oregano ex-
plant tissues. tract. However, at higher cooking temperature, the antioxidants in
oregano extract are more stable and stronger than those in rose-
Inhibition of DHA and EPA oxidation mary extract in retarding fish oil oxidation. This study provides use-
in menhaden oil during incubation ful information relative to natural antioxidants used in stabilizing
After incubation at 60 ◦ C, retained DHA and EPA of menhaden oil fish oil during cooking and storage. It could also be beneficial to the
without extract dropped to approximately 50% and 60% after day 1, food industry in the development of functional foods enriched with
and 20% and 25% after day 3, respectively (Figure 3 and 4). Their healthy long chain unsaturated fatty acids with a longer shelf life.
levels decreased to undetectable after 5 d of storage. The mecha- The results in this study support the use of spicy plants as sources
nism of lipid oxidation at 60 ◦ C is considered similar to that at room of natural antioxidants.
temperature (Frankel 1993; Pike 2003). At 25 ◦ C, it was reported that
approximately 20% of n-3 fatty acids in fish oil remained after 6 wk References
C: Food Chemistry & Toxicology

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