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Fatty acid and tocopherol contents and oxidative stability of walnut oils

Article in Journal of the American Oil Chemists' Society · September 1999

DOI: 10.1007/s11746-999-0204-2

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 Fatty Acid and Tocopherol Contents
1
and Oxidative Stability of Walnut Oils
G.P. Savagea,*, P.C. Duttab, and D.L. McNeila
a
Food Group, Animal and Food Sciences Division, Lincoln University, Canterbury, New Zealand,
and bDepartment of Food Science, Swedish University of Agricultural Sciences, Uppsala, Sweden

ABSTRACT: Walnuts (Juglans regia L.) were collected during value of the nut. Lower linoleic and linolenic acid content oils
the 1997 harvest from 13 different cultivars of trees grown in a may have a longer shelf life, and monounsaturated fatty acids
replicated trial in an experimental orchard at Lincoln Univer- may be more desirable because of their potential health bene-
sity. Two U.S. commercial cultivars (Tehama and Vina), three fits (5–7). The high linoleic acid content of walnut oil makes
European commercial cultivars (Esterhazy, G139, G120), and it undesirable for use in cooking as it is more prone to char-
eight New Zealand selections (Rex, Dublin’s Glory, Meyric,
ring, but walnuts are a perfect ingredient in a variety of
Stanley, Mckinster, 150, 151, 153) were evaluated. Total lipids
were analyzed for fatty acids by capillary gas chromatography,
breads, muffins, cakes, and biscuits (8).
tocopherols by high-performance liquid chromatography, and Walnut lipids contain about 70% polyunsaturated fatty
oxidation stability by Rancimat. The total oil content of the nuts acids, and their oxidation is linked to the appearance of un-
ranged from 64.2 to 68.9% while the stability of the oil ranged pleasant odors and flavors. Tocopherol isomers provide some
from 3.9 to 7.8 h. The oleic acid content of the oils ranged from protection against oxidation. The measurement of the tocoph-
12.7 to 20.4% of the total fatty acids, while 18:2 content ranged erol isomers in nut oils is important owing to their antioxida-
from 57.0 to 62.5% and the 18:3 contents ranged from 10.7 to tive effect and their positive nutritional effects in human me-
16.2%. Reduced stability of the oil as measured by the Ranci- tabolism. Interestingly, the measurement of these isomers in
mat method appears to be correlated to higher levels of 18:2 in nut oils and walnuts in particular was not well-documented
the extracted oil. The total tocopherol contents of these nuts apart from some data on the tocopherol content of walnuts
ranged from 268.5 to 436.0 µg/g oil. γ-Tocopherol dominated
grown in France, the United States (9), and Germany (10).
the profile while α-tocopherol was only 6% of the total content.
Peroxide values of the fresh oil were measured spectrophoto-
Lavedrine et al. (9) identified α-, γ-, and δ-tocopherol in fresh
metrically to give an indication of the overall stability. The lev- and stored nuts and noted the significant losses that occurred
els of total tocopherols when combined with the level of unsat- after 3 mon storage at 4°C. They identified γ-tocopherol as
uration in the oil in a multiple regression analysis had a signifi- the main tocopherol in walnut oil. No β-tocopherol was iden-
cant relationship (R2 = 45.2%, P < 0.001) with the peroxide tified in their samples, but low levels were observed in a
value in the oil. mixed commercial sample of walnut oil in Germany (10).
Paper no. J8955 in JAOCS 76, 1059–1063 (September 1999). The efficient extraction of fat from walnut samples for
analysis must be rapid to prevent loss of tocopherols which
KEY WORDS: Fatty acids, Juglans regia L., lipids, oxidative are unstable in the presence of unsaturated fats, oxygen, al-
stability, tocopherol, walnut. kali, and metal ions (11). Saponification of the oil or acid hy-
drolysis did not improve the recovery of the individual vita-
min isomers, and direct solvent extraction was both rapid and
efficient (9).
Walnut kernels (Juglans regia L.) generally contain about The positive nutritional advantages of walnuts in lowering
60% oil (1), but this can vary from 52 to 70% depending on blood cholesterol should not be overlooked (12). These ad-
the cultivar, location grown, and irrigation rate (2–4). The vantages come from the high levels of mono- and polyunsat-
major constituents of the oil are triacylglycerols; free fatty urated fatty acids and possibly the tocopherol content (6,7).
acids, diacylglycerols, monoacylglycerols, sterols, sterol es- These experiments are unusual as they used specific foods,
ters, and phosphatides are all present in only minor quantities walnuts and almonds, to lower total plasma and low-density
(1). The major fatty acids found in walnut oil are oleic (18:1), lipoprotein cholesterol, thus reducing the potential risk of
linoleic (18:2), and linolenic (18:3) acids. The ratios of these coronary heart disease (6,7). The experiments carried out
to each other are important to the economic and nutritional (6,7) showed the positive effect of addition of walnuts to the
1
diet, but neither of these experiments recorded the fatty acid
Presented as a poster at the 89th AOCS Annual Meeting, Chicago, Illinois, profile of the nuts fed to their experimental subjects. This is
May 10–13, 1998.
*To whom correspondence should be addressed.
important as it was shown that the fatty acid profile of walnut
E-mail: [email protected] oil varies between cultivars (2). It is important to identify

Copyright © 1999 by AOCS Press 1059 JAOCS, Vol. 76, no. 9 (1999)
1060 G.P. SAVAGE ET AL.

these differences in locally grown cultivars and to identify ing for 1 h in steel tubes containing four steel balls to facili-
which fatty acids give the best nutritional qualities. tate homogenization of the seeds (17,18). The homogenates
Interestingly, the fatty acid profiles of different walnut cul- were filtered through defatted filter papers on a Buchner fun-
tivars may influence flavor stability during storage. Consumer nel (Kimble, Vineland, NJ) under vacuum, and the residues
taste tests showed that locally grown cultivars have markedly were washed twice with 20 mL of the same solvent; thereafter
differing organoleptic properties after only short-term storage 35 mL of 6.7% sodium sulfate was added, and the upper layer
of in-shell nuts in dry cool conditions (13). These differences was rotary-evaporated under reduced pressure at 40°C. The
in flavor stability may depend on the types and amounts of pure oil was stored at −20°C until analysis commenced the
fatty acids present in the different cultivars of walnuts evalu- following day.
ated. However, the major cause of decreased walnut palatabil- Peroxide value. The peroxide value was determined, after
ity is oxidation of oils during storage and the resulting appear- calibration with iron chloride solution, following the Interna-
ance of unpleasant odors and flavors. An investigation of this tional Dairy Federation standard Method 74A (19). Freshly
phenomenon forms part of an ongoing series of experiments. extracted oil (0.4 g) was weighed into a 15-mL Kimax (Kim-
The present study is a preliminary investigation of the fat ble) tube, and 9.6 mL chloroform/methanol (70:30) was
and fatty acid compositions, tocopherols, and stability of 13 added and mixed. Following this, 0.05 mL ammonium thio-
of the potentially most useful cultivars of walnuts from Eu- cyanate solution (30 g/100 mL) was added and vortexed. The
rope and the United States that can be grown in the Canter- absorbance of this mixture was measured at 500 nm, and after
bury region of New Zealand. These data may help in select- adding 0.05 mL of the iron chloride solution (0.35 g
ing cultivars that are useful for future commercial production FeCl3·4H2O in 100 mL distilled water and add 2 mL 10 mol/l
in the region and in identifying suitable cultivars for use in HCl) the mixed solution was allowed to stand in the dark for
food products. 5 min. The increase in absorbance was measured against a
reagent blank (9.9 mL chloroform/methanol mix and 0.05 mL
ammonium thiocyanate solution). The peroxide value of the
MATERIALS AND METHODS
fat was expressed as meq of oxygen/kg fat.
Sources of the walnuts. Two replicated walnut variety trials Oxidative stability, Rancimat method. Extracted oil (2.5 g)
were planted at Lincoln University in 1985 and 1987, respec- was weighed into a 25 × 150 mm test tube and connected to a
tively, by the Walnut Action Group (Rex Baker Memorial Rancimat 679 (Metrohm, Herisau, Switzerland). Air was
Trial). The trees were grafted clonal material on seedling root- passed through the samples at 15 L/min while being heated at
stock (primarily J. regia but with some trees on J. nigra to ob- 110°C. The gases released during oxidation of the oil sample
tain adequate rootstock numbers). There were six replicates of were carried into a cell containing 60 mL of water. The
17 cultivars/selections and two replicates of a further five cul- change in conductivity of the cell was plotted on a graph for
tivars in total. Two U.S. commercial cultivars (Tehama and 18 h. The oxidative stability was taken as the time corre-
Vina), three European commercial cultivars (Esterhazy, G139, sponding to the point of intersection of the two parts of the
G120), and eight New Zealand selections [Dublin’s Glory graph (the linear part at the beginning of the analysis and the
(143), Meyric (1199), Stanley (Ble 300), McKinster, Rex exponential part at the end of the analysis). All analyses were
(152), 150, 151, 153] were evaluated. The numbers in paren- carried out in triplicate.
theses are the Walnut Action Group’s Accession Number. The Analyses of tocopherol by high-pressure liquid chromatog-
New Zealand seedling selections were made by the Walnut raphy (HPLC). The tocopherol content was determined by di-
Action Group. The trials were planted in Templeton Silt Loam, rect injection of the oil samples into an HPLC following the
and the entire block was surrounded by guard trees to act as method of Dutta et al. (20). In brief, oil samples weighing 0.5
pollenizers. Details of the management practices and climate g were dissolved in 5.0 mL n-heptane, and 25 µL was injected
conditions are given elsewhere (14). The harvesting and dry- into a guard column (4 × 4 mm) LiChroCART 4-4 coupled to
ing conditions followed the standard methods (14). The wal- a 25 × 0.4 cm LiChroCART 250-4 packed with Lichrospher
nuts analyzed in this experiment were harvested in April and 100 NH2, 5-mm particle-size column (Merck KGaA, Darm-
May 1997 with harvests at 3-d intervals. The walnuts were stadt, Germany). Both columns were fitted onto a Waters
collected from the ground and were then washed and dried in 600E solvent delivery system (Waters, Milford, CT). Peaks
a forced-air drier at 30°C to a moisture content of ca. 9% (15). were detected using a Perkin-Elmer LS-2 filter fluorimeter
The nuts were then opened using a standard method (13), and (Perkin-Elmer, Buckinghamshire, United Kingdom) set at
the kernels were vacuum-packed in plastic bags and stored at wavelengths of 295 and 320 nm for excitation and emission,
−70°C until they could be extracted. Chemical analysis was respectively. The mobile phase was heptane/tert-butylmethyl-
carried out on bulked harvest samples. ether/tetrahydrofuran/methanol (79:20:0.98:0.02, by vol) at a
Chemical analysis. The total fat content was determined flow rate of 1.75 mL/min. The relative amounts of each to-
in accordance with AOAC Method 7.061 (16). copherol were calculated using an external standard method
Lipid extraction for further analysis. Finely chopped nuts using reference samples of tocopherols (Merck KGaA), and
(10 g) were extracted with 30 mL hexane/isopropanol (3:2, an HP 3396A integrator (Hewlett-Packard, Palo Alto, CA)
vol/vol) at room temperature under vigorous horizontal shak- was used to calculate the peak areas.

JAOCS, Vol. 76, no. 9 (1999)

 FATTY ACID, TOCOPHEROL CONTENT, AND OXIDATIVE STABILITY OF WALNUT OILS 1061

Preparation of fatty acid methyl esters (FAME). Approxi- RESULTS AND DISCUSSION
mately 20 mg of extracted oil was treated with 2 mL 0.01 M
NaOH in dry methanol at 60°C for 30 min under continuous The total oil content of walnut kernels ranged from 64.2 to
shaking essentially as described (17). The tubes were cooled 68.9%, while the stability of the freshly extracted oil ranged
under running water, and 2 mL of 10% NaHSO4 /25% NaCl in from 3.9 to 7.8 h (Table 1). Walnut oil is more unstable in the
water (1:1), 3 mL of water, and 1 mL hexane were added. The Rancimat test when compared to hazelnut oil (21) because
tubes were shaken vigorously and left to stand to allow the lay- walnut oil contains much higher levels of polyunsaturated
ers to separate. The upper hexane layer containing FAME was fatty acids. Interestingly, the stability of the oils extracted
transferred to a small tube and stored at −20°C for later analy- from individual cultivars ranged widely, and more unstable
sis by capillary-column gas–liquid chromatography (GC). oils such as those extracted from the European-sourced nuts
FAME analysis by GC. For this purpose, a 50 × 0.22 mm, (Esterhazy and G139) did not have higher levels of linoleic
0.25 µm film thickness fused-silica WCOT capillary column (18:2) and linolenic (18:3) acids compared to more stable oils
BPX70 (SGE, Austin, TX) was connected to a Varian 3700 extracted from Vina, G120, and Stanley. Overall the Ranci-
gas chromatograph (Palo Alto, CA) equipped with a flame- mat values for the samples of fresh oil were higher than those
ionization detector and split/splitless injector. Helium was observed by Matthäus (10) for a mixed sample of oil which
used as the carrier gas at a velocity of 23 cm/s, and as the may have been stored for some time prior to analysis. There
make-up gas at a rate of 30 mL/min. A temperature program was also some difference in the conditions used between the
of 158°C for 5 min rising to 220°C at a rate of 2°C/min was two Rancimat tests. The results from this experiment and
used. The FAME dissolved in hexane was injected (1 µL) in from Matthäus (10) confirm that walnut oil is relatively un-
a split mode of injection at a split ratio of 40:1. The injector stable compared to other common plant oils. The peroxide
and detector temperatures were 230 and 250°C, respectively. values of the oil ranged from 1.0 to 5.4 meq oxygen/kg fat.
A Varian 4270 integrator was used for recording the peak The freshly extracted oil from the New Zealand selected cul-
areas. No response factors were applied in calculating fatty tivars contained both the highest and lowest peroxide values
acid composition, since the GC temperature program showed of all the nuts tested. All the nuts had a very acceptable taste,
almost equal responses for different FAME standard mix- and no rancidity could be detected organoleptically.
tures. All analyses were carried out in duplicate. The major fatty acids in walnuts, as determined by capil-
Data analysis. The data were analyzed using multiple re- lary-column GC (Table 1), were palmitic (16:0), oleic (18:1),
gression and General Linear Model analysis of variance in linoleic (18:2), and linolenic (18:3). The polyunsaturated fatty
Minitab for Windows in which all parameters were included acids made up between 69.6 and 78.7% of the total fatty
in a stepwise fashion in all combinations. The program then acids; and analysis of the data shows that the 18:2 and 18:3
selected the best combination of factors which maximized the fatty acids increased together in particular samples, and at the
adjusted R2 value. same time the contents of the 14:0, 16:0, 16:1, and 18:0 were

TABLE 1
Total Oil, Rancimat Value (h), Peroxide Value (meq O2/kg fat) and Fatty Acid Composition (%)
of 13 Different Cultivars of Walnuts Grown at Lincoln, Canterbury, New Zealanda
Selections Total Peroxide Rancimat
and origins oil value value 16:0 18:0 18:1 18:1∆11 18:2 18:3 20:1
Europe and United States
Esterhazy 64.2 2.2 3.9 7.47 1.63 17.44 0.68 58.83 13.54 0.12
G139 64.2 4.1 3.9 6.65 1.40 16.46 0.71 61.98 12.71 0.14
G120 65.3 4.6 7.5 7.73 2.05 19.58 0.69 57.09 12.45 0.12
Tehama 67.6 2.0 6.1 7.61 1.35 19.54 0.81 57.88 12.38 0.14
Vina 66.9 3.3 7.5 6.46 1.43 17.94 0.68 58.03 15.07 0.11
New Zealand
Rex 67.7 2.9 4.8 6.59 0.07 12.66 0.81 62.48 16.17 0.11
Dublin’s Glory 66.2 1.0 4.6 7.76 0.08 18.95 0.85 57.01 13.10 0.12
Meyric 68.9 5.1 5.4 7.30 0.08 18.09 0.85 58.43 13.31 0.11
Stanley 64.9 5.1 7.8 6.72 0.08 20.36 0.63 59.24 11.18 0.11
McKinster 66.4 2.1 5.9 6.22 0.06 18.71 0.77 61.31 10.65 0.06
150 65.2 5.4 4.9 7.15 0.06 17.39 0.74 60.45 12.65 0.12
151 64.5 4.9 4.2 6.75 0.06 16.20 0.71 61.72 12.71 0.14
153 67.6 2.8 4.9 6.84 0.06 14.35 0.58 61.64 15.21 0.10

SE mean 0.5 0.2 0.1 0.15 0.08 0.48 0.40 0.52 0.23 0.02
Significance *** *** *** *** *** *** * *** *** NS
a
Means of duplicate analyses. Trace amounts of 14:0, 16:1, 20:0, and 22:0 were present in all cultivars; these fatty acids
made up <0.2% of the total fatty acids. P < * = 0.05, *** = 0.001.

JAOCS, Vol. 76, no. 9 (1999)

1062 G.P. SAVAGE ET AL.

TABLE 2 tivars generally showing an increased variability indicated by

Total and Individual Tocopherol Contents (µg/g oil) the higher SD values, when compared to European- and
of the 13 Different Cultivars of Walnuts Grown
United States-sourced material. The New Zealand selected
at Lincoln, Canterbury, New Zealanda
cultivar Rex had the lowest total tocopherol content while
Selections
and origins α β γ δ Total
Dublin’s Glory had the highest level of all the cultivars. The
proportion of the individual tocopherols remained constant in
European and United States all the nuts. The tocopherol content of walnuts in this study is
Esterhazy 25.5 5.2 343.2 62.1 436.0
G139 18.1 3.5 288.3 32.4 342.4
comparable to the mixed commercial sample of oil measured
G120 25.2 5.8 327.2 45.0 403.2 by Matthäus (10) and one sample of walnut oil measured by
Tehama 26.1 5.3 273.6 37.3 342.3 Coors (23), except that they did not observe β-tocopherol in
Vina 24.0 3.5 300.9 48.5 376.9 their samples. This is the first study to accurately record the β-
New Zealand tocopherol content of named cultivars of walnuts. As antici-
Rex 14.8 3.7 233.9 37.8 290.2
Dublin’s Glory 28.7 4.2 355.0 47.0 434.8
pated by Lavedrine et al. (9), β-tocopherol is present at low
Meyric 27.7 4.7 304.9 48.2 385.6 levels in walnut oil. Previous studies were unable to separate
Stanley 28.5 1.0 328.6 44.8 402.8 β- and γ-tocopherols in walnut oil (9). These studies confirm
McKinster 23.3 4.2 265.2 29.6 322.2 that γ-tocopherol is the predominant homolog. The tocopherol
150 20.2 3.1 206.9 38.3 268.5 values observed in the samples of fresh oil in this study are
151 20.1 8.2 284.6 42.1 355.0
153 20.6 6.8 267.2 28.0 322.6
variable between different cultivars, but overall the values are
higher than the values recorded for Hartley and Franquette by
SE mean 1.8 2.1 6.9 4.2 9.6 Lavedrine et al. (9). Notably, however, their nuts were stored
Significance ** NS *** ** *** at +4°C for 3 mon prior to analysis. They went on to show that
a
Means of duplicate analysis. P < ** = 0.01, *** = 0.001. significant losses of γ-tocopherol occurred if the nuts were
stored 5 and then 14 mon at the same temperature.
reduced together. The profile of fatty acids found in this ex- The data in Table 3 show the best statistically determined
periment is comparable to data previously reported in the lit- regression retationships for Rancimat and peroxide values
erature (2–4,11,22) except that this is the first study to report based on the tocopherol and fatty acid composition of the nut
the presence of cis-vaccenic acid (18:1∆11), which ranged oil. The regression analysis shows that the Rancimat value
from 0.6 to 0.9% in walnut oil (Table 1). Some variation in was negatively associated with the 18:2, 20:1, and 18.1∆11
the fatty acid composition between the different cultivars of contents. In contrast the peroxide value of the freshly ex-
walnuts grown at Lincoln can be seen. Interestingly, while the tracted oil was positively associated with the total tocopherol
fatty acid compositions of the European- and United States- and 20:1 contents. This is the first report of the possibility that
sourced nuts were comparable, the New Zealand selections some of the minor oil components may adversely affect oil
showed considerable variations. For instance, in the case of stability as previous reports did not look at these components.
16:0, 18:1, 18:2, and 18:3, the New Zealand selections Surprisingly the statistical analysis did not indicate strong re-
showed both the highest and the lowest values for each of lationships between 18:3 contents and the Rancimat and per-
these fatty acids. oxide values. There is thus the possibility of breeding or se-
The total tocopherol content of New Zealand nuts ranged lecting for low levels of these products to enhance storage, as
from 290 to 435 µg/g oil (Table 2) with the New Zealand cul- a substantial range was found in different cultivars (Table 1).

TABLE 3
Most Significant Regression Relationships Derived Between Measured Stability Values of the
Extracted Oil and Its Tocopherol and Fatty Acid Concentrations
R2adj P P SS P SS P SS P
Intercept overall

[18:2] [20:1] [18:1∆11]

Rancimat value 45.2 *** ** 10.1 * 8.0 ** 7.3 ***

[total tocopherol] [20:1]

Peroxide value 44.5 *** *** 22.0 * 7.0 — — ***

Regression equations
Rancimat valuea = 36.6 − 0.0377 [18:2] − 23.3 [20:1] − 8.04 [18.1∆11]c
Peroxide valueb = 8.49 − 0.0202 × [total tocopherol] + 21.7 [20:1]
a
Hours.
b
meq oxygen/kg fat.
c
Fatty acids as g/100 g oil, tocopherol as µg/g oil. P < * = 0.05, ** = 0.01, *** = 0.001. SS = sums of
squares for regression component.

JAOCS, Vol. 76, no. 9 (1999)

 FATTY ACID, TOCOPHEROL CONTENT, AND OXIDATIVE STABILITY OF WALNUT OILS 1063

Further verification of the possible involvement of these fatty α-Linolenic Acid Flaxseed (Linum usitatissimum): Some Nutri-
acids is important in the understanding of the causes of ran- tional Properties in Humans, Br. J. Nut. 62:433–453 (1993).
6. Sabaté, J., G.E. Fraser, K. Burke, S.F. Knutsen, H. Bennett, and
cidification and breakdown of walnut oils during storage.
K.D. Linstead, Effects of Walnuts on Serum Lipid Levels and
The present study is the first to record the total and indi- Blood Pressure in Normal Men, New Engl. J. Med. 329:603–607
vidual tocopherol content of fresh oil extracted from named (1993).
walnut cultivars. Studies are under way to determine the sta- 7. Abbey, M., M. Noaks, G.B. Belling, and P.J. Nestel, Partial Re-
bility of the polyunsaturated fatty acids and the tocopherol placement of Saturated Fatty Acids with Almonds or Walnuts
Lowers Total Plasma Cholesterol and Low-Density-Lipoprotein
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Owing to the high commercial value of both whole wal- Drink Rev. 121:123–125 (1991).
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taken to prevent oxidation of the unstable polyunsaturated ographic Origin, Variety and Storage on Tocopherol Concentra-
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able range in stability to the Rancimat test occurs between the Vegetable Oils by Rancimat and Conductivity and Chemilumi-
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ACKNOWLEDGMENTS pp. 19.
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greatly appreciated. sakademien, Stockholm) 28:551 (1968).
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Composition of Walnut (Juglans regia L.) Types Selected in nung von Fett- und Olvermischungen, Fat. Sci. Technol.
Darende, Ibid. 19:299–302 (1995). 93:519–526 (1991).
5. Cunnane, S.C., S. Ganguli, C. Menard, A.C. Liede, M.J.
Hamadeh, Z. Chen, T.M.S. Wolever, and D.J.A. Jerkins, High [Received July 22, 1998; accepted March 7, 1999]

JAOCS, Vol. 76, no. 9 (1999)

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