Lipid components of flax, perilla, and chia seeds
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794 Eur. J. Lipid Sci. Technol. 2012, 114, 794–800
Research Article
Lipid components of flax, perilla, and chia seeds
Ozan Nazim Ciftci1, Roman Przybylski1 and Magdalena Rudzińska2
1
Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB, Canada
2
Faculty of Food and Nutrition, Poznan University of Life Sciences, Poznan, Poland
Composition of fatty acids, tocopherols, sterols, and TAGs in the lipids of flax, perilla, and chia seeds were
investigated where lipid content was at 45, 40, and 35%, respectively. a-Linolenic acid (ALA) dominated
among fatty acids in all oils and accounted for 58.2, 60.9, and 59.8% in flax, perilla, and chia,
correspondingly in these three oils trilinolenin was the main TAG found at 19.7, 22.6, and 21.3%.
Triunsaturated TAGs accounted for 77.9, 77.5, and 74.5% of the total amounts in flax, perilla, and
chia oils. Contents of tocopherol were at 747 in flax, 734 in perilla, and 446 mg/kg in chia seed lipids.
g-Tocopherol was the dominating isomer contributing 72.7% in flax, 94.3% in perilla, and 94.4% in chia to
the total amount of tocopherols. Flaxseed lipids contained 25.6% of plastochromanol-8, derivative of
g-tocotrienol with longer side chain; perilla and chia oils contained only 1.4% of it. Phytosterols were
present at 4072, 4606, and 4132 mg/kg in those seeds, respectively. Among sterols, b-sitosterol dominated
and was found at 35.6, 73.3, and 49.8% of the total amounts of sterols in flax, perilla, and chia seed lipids.
All of the investigated oilseeds have an excellent nutritional quality and can be a potential source of
nutraceutical fats which can enrich diet in linolenic acid and other functional components.
Keywords: Fatty acids / Phytosterols / Specialty oils / Tocopherols / a-Linolenic acid
Received: June 14, 2011 / Revised: February 13, 2012 / Accepted: February 24, 2012
DOI: 10.1002/ejlt.201100207
1 Introduction Flax, perilla, and chia seeds assessed in this study are
among the important sources of specialty oils which are rich
It is well understood by consumers that good health comes in linolenic acid. For many years, flax (Linum usitatissimum)
from good diet. Lipids are one of the main nutrients of the has been grown primarily for fiber and oil used in painting and
human diet, and are of great importance to consumers and linoleum industry. Flaxseeds were used as baking ingredient,
food industry. Seed oils constitute a significant part of the mainly for decorative purpose, and at negligible amounts.
typical diet because they are a source of important essential Recently, considerable attention has been paid to its func-
nutrients such as fatty acids, tocopherols, and phytosterols. tional and nutritional properties. Health benefits offered by
Health conscious consumers command industry to provide flax nutraceuticals such as lignans, fiber, and oil, inspired
oilseeds and oils which are rich in beneficial compounds demand for flaxseed as food and feed ingredient [4].
including omega-3 fatty acids, tocopherols, and sterols. Perilla (Perilla frutescens) seed and its oil have been used as
Specialty oils have unique lipid components with inter- a food and medicinal remedy in Southeast Asia [5]. Highly
esting dietary properties, and occupy high value a niche unsaturated perilla oil has limited application as a food ingre-
market [1]. Among lipid components, linolenic acid, precur- dient and has been mainly used as drying oil in paints.
sor of the long chain n-3 fatty acids in human, antioxidants, Currently, when typical diet is deficient in n-3 fatty acids
and phytosterols get the most attention as dietary ingredients and fish sources are dwindling, plant sources of these fatty
effectively lowering risk of heart diseases [2, 3]. acids are recognized as a useful source of it.
Chia (Salvia hispanica) is an annual herbaceous plant of
the mint family native to southern Mexico and Northern
Guatemala, cultivated by natives before Hispanic colonization
Correspondence: Dr. Roman Przybylski, Department of Chemistry and [6]. Chia disappeared as crop for centuries and was rediscov-
Biochemistry, University of Lethbridge, Lethbridge, AB T1K 3M4, Canada
ered in the middle of the 20th century, and presented as
E-mail: roman.przybylski@uleth.ca
Fax: þ1 403 3292057 exceptional source of omega-3 fatty acids, linolenic acid [7].
Usually, for the most of plant seeds fatty acid composition
Abbreviations: ALA, a-linolenic acid; ECN, equivalent carbon number has been reported, lacking data for tocopherol, phytosterol,
ß 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.ejlst.comEur. J. Lipid Sci. Technol. 2012, 114, 794–800 Lipid components of flax 795
and TAG compositions [4–7]. Therefore, the main objective 308C and air pressure at 2.5 bar. Lipids were dissolved in
of this study was an assessment of the composition and hexane (5 mg/mL) and 10 mL injected into HPLC system.
content of nutraceutical lipid components in flax, perilla, TAGs were separated on two C18 columns connected
and chia seeds to fill a knowledge gap. in series (Gemini, 250 3 mm, 5 mm; Phenomenex,
Torrance, CA, USA). Temperature of the columns was set
2 Materials and methods at 308C and a binary gradient consisting of acetonitrile (A)
and dichloromethane (B) was used at 0.4 mL/min. For sep-
2.1 Materials aration the following gradient of solvent A and B were used
(%): 70/30 for 15 min, changed to 60/40 within 10 min and
Flaxseed was obtained from a local market in Lethbridge, continued for 10 min, followed by 40/60 in 15 min, sustained
Canada. Perilla seed was a gift provided by Dr. Y.C. Lee from for 5 min, and switched to 30/70 in 5 min extended for
South Korea, and chia provided by Benexia, Peru. 5 min, afterwards returned to the initial composition in
All solvents of HPLC grade, sterol standards, pyridine 20 min keeping on 5 min equilibration. TAGs were ident-
and Sylon BTZ were purchased from Sigma–Aldrich (St ified by comparison of the retention data with authentic
Louis, MO, USA). Standards of tocopherols were obtained standards and by calculating relative retention time using
from Calbiochem-Novabiochem (San Diego, CA, USA). triolein as reference. The same standards were used for
FAME and TAG standards were purchased from Nu- detector calibration. Data acquisition and peak integration
Chek-Prep (Elysian, MN, USA). were performed using the ChromQuest 4.2 software
(Thermo Electron, Waltham, MA, USA).
2.2 Lipids
2.5 Tocopherols
Seeds were ground in a coffee grinder and 20 g homogenized
with 200 mL of chloroform–methanol (2:1, v/v) following the Extracted lipids were dissolved in hexane (5 mg/mL) and
Folch procedure [8]. Extraction was repeated thrice and the tocopherols separated using a Finnigan Surveyor Plus
lipid extracts combined and concentrated under vacuum in a HPLC System (Thermo Electron, Waltham, MA, USA) with
rotary evaporator (Buchi Labortechnik, Switzerland) at a Finnigan Surveyor FL Plus fluorescence detector set for
358C. Solvent free lipids were weighed to determine the lipid excitation at 295 nm and emission at 325 nm. A sample of
content and transferred into brown vials with iso-octane, 10 mL was injected onto a diol column (Monochrom;
flushed with nitrogen, and stored at 208C until analyzed. 250 4.6 mm, 5 mm; Varian, Palo Alto, CA, USA). The
mobile phase consisted of 7% tert-butyl methyl ether in hex-
2.3 Fatty acids ane at a flow rate of 0.6 mL/min. Standard tocopherol iso-
mers were used for identification and external calibration for
FAME were prepared according to AOCS Method Ce 1-62 each isomer separately. Plastochromanol-8, derivative of
[9] and separated on a HP 5980 series GC (Hewlett Packard, g-tocotrienol with longer side chain (Fig. 1), was quantified
Palo Alto, USA) equipped with SP-2560 fused silica capillary using g-tocopherol calibration. All results are expressed in mg
column (100 m 0.25 mm, 0.25 mm; Supelco, Bellefonte,
PA, USA). One mL of FAME sample was injected into the
GC injector operated in splitless mode for 2 min. Hydrogen R1
HO
was used as carrier gas at a flow rate of 2.0 mL/min. Column CH3 CH3 CH3
temperature was programmed from 70 to 1608C at R2 O CH3
258C/min, held for 30 min, then further programmed to R3 Tocopherol
2108C at 38C/min. Initial and final temperatures were held
R1
for 5 and 30 min, respectively. Detector temperature was set HO
CH3 CH3 CH3
at 2508C. Fatty acids were identified by comparison of the
retention data with authentic standards and the results are R2 O CH3
reported as a weight percentage of the lipid. Data acquisition R3 Tocotrienol
and peak integration were performed using ChemStation HO Isomer R1 R2 R3
CH3 CH3
(Agilent Technologies, Mississauga, Canada).
CH3 O CH3 α CH3 CH3 CH3
CH3 7
2.4 TAGs Plastochromanol-8 β CH3 H CH3
γ H CH3 CH3
TAGs of seed lipids were analyzed by HPLC using a Finnigan δ H H CH3
Surveyor Plus HPLC system (Thermo Electron, Waltham,
MA, USA) equipped with a Sedex 75 evaporative light scat- Figure 1. Structure of tocopherols, tocotrienols, and plastochroma-
tering detector (Sedere, Alfortville, France) operating at nol-8.
ß 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.ejlst.com796 O. N. Ciftci et al. Eur. J. Lipid Sci. Technol. 2012, 114, 794–800
of tocopherol per kg of lipids. Data acquisition and peak Table 1. Lipid content and fatty acid composition of flax, perilla, and
integration were performed using the ChromQuest 4.2 chia seeds a)
program (Thermo Electron, Waltham, MA, USA).
Fatty acids Flax Perilla Chia
2.6 Sterols 14:0 0.07 0.01 a 0.06 0.01 a 0.06 0.01 a
15:0 0.05 0.01 a 0.03 0.01 a 0.04 0.01 a
Sterol content and composition were determined by GC 16:0 5.1 0.25 a 5.94 0.12 a 7.10 0.05 b
following a procedure described by Rudzinska et al. [10]. 16:1 0.09 0.01 a 0.12 0.02 a 0.20 0.01 b
Briefly, 50 mg of lipids were saponified with 1 M KOH 17:0 0.08 0.01 a 0.06 0.01 a 0.06 0.01 a
in methanol for 18 h at RT, then water was added and 17:1 0.06 0.01 a 0.07 0.01 a 0.06 0.01 a
unsaponifiables extracted twice with hexane/methyl tert-butyl 18:0 3.3 0.08 b 2.20 0.14 a 3.24 0.08 b
ether (1:1, v/v). The solvent was evaporated under a stream of 18:1 18.1 0.45 c 16.21 0.07 b 10.53 0.17 a
18:2 15.3 1.01 b 14.72 0.08 a 20.37 0.19 c
nitrogen and dry residues dissolved in 0.3 mL pyridine, and
20:0 0.18 0.03 a 0.20 0.01 a 0.24 0.06 a
silylated with 1 mL of Sylon BTZ (Supelco, Bellefonte, PA,
18:3 n-6 0.18 0.02 a 0.20 0.01 a 0.27 0.02 b
USA) at RT. Derivatized sterols were separated on a Trace 18:3 n-3 58.2 0.64 a 60.93 0.10 b 59.76 0.13 b
GC Ultra (Thermo Electron, Rodano, Italy) equipped with a 20:1 0.20 0.01 a 0.17 0.02 a 0.16 0.01 a
DB-35MS capillary column (25 m 0.20 mm 0.32 mm; 20:2 0.05 0.01 a 0.05 0.01 a 0.07 0.01 a
J&W Scientific, Folsom, CA). A sample of 0.5 mL was 22:0 0.14 0.01 c 0.03 0.01 a 0.08 0.01 b
injected with an AS 3000 autosampler (Thermo Electron, 24:0 0.09 0.01 b 0.01 0.00 a 0.10 0.01 b
Rodano, Italy) into a temperature-raised injector (PTV) in a Groups
splitless mode. Column temperature was held at 1008C for SFA 7.87 0.14 b 7.58 0.05 a 8.65 0.19 c
5 min, programmed to 2508C at 258C/min, held for 1 min; MUFA 18.50 0.47 c 16.57 0.11 b 10.95 0.18 a
and programmed to 2908C at 38C/min, final temperature was PUFA 73.63 0.36 a 75.85 0.17 b 80.40 0.30 c
Ratio n-6/n-3 0.27 0.22 0.35
held for 20 min. Detector temperature was set at 3008C.
Lipids (%) 44.8 1.4 a 40.0 1.6 a 35.0 2.8 a
Hydrogen was used as the carrier gas at a flow rate of
1.5 mL/min. An internal standard, 5a-cholestane, was
Means within a column with different superscript letters are signifi-
used for quantification. Phytosterols were identified by com- cantly different ( pEur. J. Lipid Sci. Technol. 2012, 114, 794–800 Lipid components of flax 797
The amount of ALA in studied flaxseed was similar to the Table 2. Composition of the main triacylglycerides in flax, perilla,
reported last 10-year average for this crop [15]. Turkish and and chia seed lipids (area %) a)
Polish flaxseed oils contained 56.5–61.0% and 57.1% of
ALA, respectively [11, 15]. Flaxseed grown at higher tem- TAG’s ECN Flax Perilla Chia
peratures in Ethiopia contained ALA at 51.9%, lower level LnLnLn 36 19.7 1.8 22.6 1.1 21.3 1.6
when compared to temper growing conditions [13]. This is LLnLn 38 16.5 0.8 16.4 0.9 21.8 2.1
well known oilseed plant adaptation phenomena, where the OLnLn 40 18.4 1.1 18.1 1.2 11.3 1.4
content of PUFA is inversely affected by the average growing LLLn 40 4.1 0.2 3.9 0.9 7.4 0.9
temperature [19]. LnLnP 40 5.2 0.6 6.6 0.8 7.6 1.1
Method and solvent used for oil extraction also is affecting LLL 42 0.4 0.2 0.3 0.2 0.9 0.4
the amount of fatty acids. Flaxseed oil extracted with StLnLn 42 3.4 0.6 2.5 0.3 3.5 0.7
supercritical CO2 contained higher amount of ALA OLLn 42 9.7 0.9 8.7 0.7 7.7 1.1
LnLP 42 2.7 0.3 3.2 1.1 5.2 0.9
(60.5%) compared to hexane extracted oil (56.7%) [20].
OLnO 44 5.7 0.9 4.8 0.9 2.0 0.6
Authors in the same study, reported fatty acids composition
OLL 44 1.3 0.6 1.1 0.4 1.3 0.3
as follows: linoleic 14.0%, oleic 15.1%, palmitic 6.9%, and StLLn 44 1.8 0.4 1.2 0.6 2.4 0.7
stearic 4.6%. The 10-year average composition of the major PLnP 44 0.5 0.2 0.6 0.2 0.9 0.1
fatty acids in Canadian flaxseed oil was: 52.6–63.6% OLnP 46 3.2 0.7 3.5 0.8 2.7 0.4
linolenic, 14.2–17.3% linoleic, 14.5–22.4% oleic, 4.9– StLL 46 0.2 0.1 0.1 0.1 0.4 0.1
5.5% palmitic, and 3.0–3.7% stearic acid [15]. OLO 46 1.5 0.6 1.2 0.3 0.7 0.2
Widespread distribution of fatty acids is mainly affected by LOP 48 0.9 0.2 0.9 0.2 0.9 0.2
growing conditions and varieties, the fatty acid composition OOO 48 0.6 0.1 0.4 0.1 0.1 0.1
can differ by 10% for the same variety grown at different parts StLO 48 0.6 0.2 0.3 0.1 0.4 0.2
of prairies [15]. OPO 48 0.5 0.1 0.5 0.2 0.2 0.1
StOO 50 0.3 0.1 0.2 0.1 0.1 0.1
Longvah and Deosthale [18] reported 56.8% ALA,
Others 2.9 0.6 2.9 0.5 1.2 0.2
17.6% linoleic, 12.9% oleic, 8.9% palmitic, and 3.8% stearic
UUU 77.9 77.5 74.5
acids in perilla seed oil. Whereas Shin and Kim [16] analyzed TPUFA 40.7 43.2 51.4
five perilla cultivars and observed 61.1–64.0% linolenic, SUU 18.8 19.0 23.4
14.3–17.0% linoleic, 13.2–14.9% oleic acid, 6.3–6.7% pal-
mitic, and 1.5–1.7% stearic acid. ECN, equivalent carbon number; Ln, linolenic; L, linoleic; O, oleic;
Published major fatty acids compositions in chia seed oil P, palmitic; St, stearic; symbols StLO, PLO, and others indicate fatty
were at: 63.5–65.1% linolenic, 17.4–18.7% linoleic, 7.6– acid present in triacyglycerols however do not represent it specific
8.7% palmitic, 6.1–6.3% oleic, and 2.6–3.0% stearic acids configuration.
[20–22]. Flax, perilla, and chia are better sources of ALA Triglycerides: UUU, triunsaturated; TPUFA, containing only
PUFA; SUU, one saturated fatty acid.
than camelina (38.1%), fenugreek (23.2%), cranberry a)
Values are reported as mean SD of three replications (n ¼ 3).
(22.3%), and hemp (19.7%) [23–25].
The ratio of n-6 to n-3 fatty acids in flax and chia was at
0.28 and 0.35 and significantly higher ( p798 O. N. Ciftci et al. Eur. J. Lipid Sci. Technol. 2012, 114, 794–800
parameter is usually in the range of 52–54 [29]. Shift to lower and it place on published chromatogram is showing at
ECN values is directly related to the higher contribution of retention time where usually plastochromanol-8 appears.
PUFA, particularly high content of linolenic acid in analyzed Syvaoja et al. [33] reported 573 mg/kg of g-tocopherol in
oils. Established in our study the flaxseed oil TAG’s compo- flaxseed oil.
sition are similar to those reported by Holcapek et al. [30] and Shin and Kim [16] analyzed five perilla seeds varieties and
Ayorinde [29]. To the best of our knowledge, there are no reported that g-tocopherol at 92% was the major tocopherol
published data on TAG’s composition in perilla and chia oils, isomer, followed by very small amounts of a isomer.
and comparison is not possible. Published data reporting the content and composition of
tocopherols in chia seed lipids is lacking, and comparison is
3.4 Tocopherols not possible.
In some publications it is reported that it is a positive
Tocopherol composition of flaxseed, perilla, and chia oils in relationship between degree of oil unsaturation and the
Table 3 is presented, where g-tocopherol was the main iso- amount of tocopherols [34]. The results for all oils rich in
mer contributing 72.7, 94.3, and 94.4% to the total amount ALA reported in this study do not support this concept and
of tocopherols, respectively. The amounts of g-tocopherol in suggest that other seed components play role in protecting
flaxseed, perilla, and chia lipids were at 542, 691, and this highly unsaturated oil [35].
422 mg/kg of oil, respectively (Table 3). Plastochromanol-
8, derivative of g-tocotrienol (Fig. 1), is unique tocopherol 3.5 Sterols
usually detected in flaxseed and canola, but rearly is present
in other oils in significant amounts. This tocopherol isomer Phytosterol composition for flax, perilla, and chia seed lipids
was observed in flaxseed at 191 mg/kg (25.6%), while in in Table 4 is presented. Perilla oil contained the highest
perilla and chia at 10 (1.4%) and 2 mg/kg (0.4%), respect- amount of sterols at 4604 mg/kg followed by chia at
ively (Table 3). Content of total tocopherols in flaxseed did 4132 mg/kg and flaxseed at 4072 mg/kg. We identified nine
not differ significantly from that in perilla, whereas in chia was sterols in perilla, eight in flaxseed, and four in chia oils.
significantly lower ( pEur. J. Lipid Sci. Technol. 2012, 114, 794–800 Lipid components of flax 799
major component. The analyzed oils had higher amounts [4] Thompson, L., Cunnane, S., In: Thompson, L., Cunnane,
of phytosterols when compared to extra virgin olive S. (Eds.), Flaxseed in Human Nutrition, AOCS Press,
Champaign 2003, pp. 62–196.
(3280 mg/kg) and safflower oils (3960 mg/kg) nevertheless
[5] Shin, H. S., in: Yu, H. C., Haga, M. (Eds.), Perilla—The
lower than soybean (4890 mg/kg), sunflower (6920 mg/kg), Genus Perilla, Harwood Academic Publishers, Amsterdam
canola (13 260 mg/kg), and corn oils (15 320 mg/kg) [36]. 1997, pp. 93–108.
To the best of our knowledge, there are no published [6] Ayerza, R., Oil content and fatty acid composition of chia
reports describing sterols in flaxseed, perilla, and chia oils, (Salvia hispanica L.), from five locations in Northwestern
eliminating possibility to do comparison. Argentina. J. Am. Oil Chem. Soc. 1995, 72, 1079–1081.
[7] Ayerza, R., Coates, W., Chia: Rediscovering a Forgotten
4 Conclusions Crop of the Aztecs, The University of Arizona Press,
Tucson 2005.
[8] Folch, J., Lees, M., Stanley, G. H. S., A simple method for
Results of the study revealed that flax, perilla, and chia seed
the isolation and purification of total lipids from animal
lipids are excellent sources of ALA, which is a precursor of the tissues. J. Biol. Chem. 1957, 266, 497–509.
long chain PUFA metabolically formed in humans. These [9] AOCS. Official and Recommended Practices of the American Oil
oils also contain important amounts of other nutraceutical Chemist’s Society, 5th Edn., American Oil Chemist’s Society,
components such as tocopherols and sterols, and reported Champaign, IL 1997.
nutritionally important amounts of lignans in flaxseed oil. [10] Rudzinska, M., Musnicki, C., Wasowicz, E., Phytosterols
Fish oil the main source of long chain n-3 fatty acids is not and their oxidized derivatives in seeds of winter oilseed rape.
available to all consumers because of price, social factors and Rosliny Oleiste 2003, 24, 51–66.
dwindling fish population due to overfishing. Therefore, [11] Kozlowska, J., in: Kozlowska, R. (Ed.), Flax in Europe
Production and Processing, Proceedings of the European
renewable resources are needed to ensure enriched supply Regional Workshop on Flax, Poznan, Poland 1989.
of these fatty acids as ingredients in food formulations.
[12] Hettiarachchy, N., Hareland, G., Ostenson, A., Balder-
Flaxseed, perilla, and chia can be used in the form of seed Shank, G., 1990, Composition of eleven flaxseed varieties
and/or oil to enriched food products with linolenic acid and grown in North Dakota. In: Proceedings of the 53rd Flax
by this way to change ratio of n-6 to n-3 in our diet [3]. Institute of the United States, Fargo, 36–40.
Production of these oilseeds is also a viable enrichment of [13] Wakjira, A., Labuschagne, M. T., Hugo, A., Variability in
alternative crops and is economically attractive to farmers and oil content and fatty acid composition of Ethiopian and
food formulators due to the premium price paid for specialty introduced cultivars of linseed. J. Sci. Food Agric. 2004,
84, 601–607.
oils and oilseeds. Canada is one of the major producers of
[14] Łukaszewicz, M., Szopa, J., Krasowska, A., Susceptibility of
flaxseed, particularly Canadian prairies where growing con- lipids from different flax cultivars to peroxidation and its
ditions supporting high level of linolenic acid and oil content lowering by added antioxidants. Food Chem. 2004, 88,
in the seed. Following example of flaxseed, Canadian farmers 225–231.
are now producing chia seeds which are directed to the health [15] Canadian Grain Commission. 2010, Quality of western
food market. These oilseeds and oils containing elevated Canadian flaxseed 2010. Grain Research Laboratory,
amounts of linolenic acid, good proportion of tocopherols, Winnipeg, MB, Canada.
and sterols can be a good food ingredient enriching diet in [16] Shin, H. S., Kim, S. W., Lipid composition of perilla seed. J.
Am. Oil Chem. Soc. 1994, 71, 619–622.
many countries.
[17] Tsuyuki, H., Itoh, S., Nakatsukasa, Y., Studies on the lipids
in perilla seeds. Bull. Coll. Agric. Vet. Med. Nihon Univ. 1978,
We acknowledge financial support for this research provided by the 35, 224–230.
Alberta Value Added Corporation, the Agriculture Funding
[18] Longvah, T., Deosthale, Y. G., Chemical and nutritional
Consortium, and Bioactive Oil Program. studies on Hanshi (Perilla frutescens), a traditional oilseed
from Northeast India. J. Am. Oil Chem. Soc. 1991, 68,
The authors have declared no conflict of interest. 781–784.
[19] Barthet, V. J., Daun, J. K., in: Daun, J. K., Eskin,
N. A. M., Hickling, D. (Eds.), Canola, Chemistry,
Production, Processing, and Utilization, AOCS Press,
References Urbana, IL 2011, pp. 122–131.
[20] Bozan, B., Temelli, F., Supercritical extraction of flaxseed
[1] Gunstone, F. D., in: Shahidi, F. (Ed.), Nutraceutical and oil. J. Am. Oil Chem. Soc. 2002, 79, 231–235.
Specialty Lipids and Their Co-products, CRC Press, Taylor [21] Heuer, B., Yaniv, Z., Ravina, I., Effect of late salinization of
& Francis Group, Boca Raton 2006, pp. 91–127. chia (Salvia hispanica), stock (Matthiola tricuspidata) and
[2] Bang, H. O., Dyerberg, J., Nielsen, A. B., Plasma lipid and evening primrose (Oenothera biennis) on their oil content
lipoprotein pattern in Greenlandic west-coast Eskimos. and quality. Ind. Crops Prod. 2002, 15, 163–167.
Lancet 1971, 1, 1143–1146. [22] Peiretti, P. E., Gai, F., Fatty acid and nutritive quality of chia
[3] Schmitz, G., Ecker, J., The opposing effects of n-3 and n-6 (Salvia hispanica L.) seeds and plant during growth. Anim.
fatty acids. Prog. Lipid Res. 2008, 47, 147–155. Feed Sci. Technol. 2009, 148, 267–275.
ß 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.ejlst.com800 O. N. Ciftci et al. Eur. J. Lipid Sci. Technol. 2012, 114, 794–800
[23] Shukla, K. S., Dutta, P. C., Artz, W. E., Camelina oil and its ionization time-of-flight mass spectrometry. Lipid. Technol.
unusual cholesterol content. J. Am. Oil Chem. Soc. 2002, 79, 2000, 12, 41–44.
965–969. [30] Holcapek, M., Jandera, P., Zderadicka, P., Hruba, L.,
[24] El-Sebaiy, A., El-Mahdy, A. R., Lipid changes during ger- Characterization of triacylglycerol and diacylglycerol compo-
mination of fenugreek seeds (Trigonella foenum-graecum). sition of plant oils using high-performance liquid chroma-
Food Chem. 1983, 10, 309–319. tography atmospheric pressure chemical ionization mass
[25] Parker, D., Adams, D. A., Zhou, K., Harris, M., Yu, L., spectrometry. J. Chromatogr. 2003, 1010, 195–215.
Fatty acid composition and oxidative stability of cold-pressed [31] Bozan, B., Temelli, F., Chemical composition and oxidative
edible seed oils. J. Food Sci. 2003, 68, 1240–1243. stability of flax, safflower and poppy seed and seed oils.
Bioresour. Technol. 2008, 99, 6354–6359.
[26] Kochhar, S. P., in: Gunstone, F. D. (Ed.), Vegetable Oils
in Food Technology, Composition, Properties and Uses, [32] Oomah, B., Kenaschuk, O., Gluseppe, M., Tocopherols in
2nd Edn., Blackwell Publishing Ltd., Oxford 2011, flaxseed. J. Agric. Food Chem. 1997, 45, 2076–2080.
pp. 291–306. [33] Syvaoja, E. L., Piironen, V., Varo, P., Koivistoinen, P.,
[27] Siriamornpun, S., Li, D., Yang, L., Suttajit, S., Suttajit, M., Salminen, K., Tocopherols and tocotrienols in finish foods:
Variation of lipid and fatty acid compositions in Thai Perilla Oils and fats. J. Am. Oil Chem. Soc. 1986, 63, 328–329.
seeds grown at different locations. J. Sci. Technol. 2006, 28, [34] Shahidi, F., Shukla, V. K. S., Nontriacylglycerol constituents
17–121. of fats, oils. Inform 1996, 7, 1227–1232.
[28] Simopoulos, A. P., The importance of the ratio of omega-6/ [35] Przybylski, R., Daun, J. K., Storage stability of milled flax-
omega-3 essential fatty acids. Biomed. Pharmacother. 2002, seed. J. Am. Oil Chem. Soc. 2001, 78, 105–106.
56, 365–379. [36] Phillips, K. M., Ruggio, D. M., Toivo, J. I., Swank, M. A.,
[29] Ayorinde, F. O., Determination of the molecular distribution Simpkins, A. H., Free and esterified sterol composition of
of triacylglycerol oils using matrix assisted laser desorption/ edible oils and fats. J. Food Comp. Anal. 2002, 15, 123–142.
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