Omega-9 Fatty Acid

Related terms:

Omega-3 Fatty Acid, Oleic Acid, Omega-6 Fatty Acid, Linoleic Acid, Polyunsaturated
Fatty Acid, Lipids, Olive Oil, Fatty Acids, Saturated Fatty Acids, Unsaturated Fatty
Acids

View all Topics

Brain lipids and ageing

J.M. Bourre, in Food for the Ageing Population, 2009

12.8 Omega-9 fatty acids

The main omega-9 fatty acid in the brain is oleic acid (18:1 9), but there are also large
quantities of long-chain derivatives, mainly 24:1, especially in the myelin sheath. The
nutritional value of oleic acid in a balanced diet has been the subject of a number
of studies, with particular emphasis on the cardiovascular system. But this fatty
acid is also important for the brain (Bourre and Dumont, 2003). Feeding rats a diet
lacking oleic acid leads to a reduction of the oleic acid concentration in many organs,
including the sciatic nerve, but not in the brain. Therefore, the endogenous synthesis
in many organs does not compensate for the absence of oleic acid from the food
(Bourre et al., 1997b). This fatty acid is therefore partially essential.

There may be several explanations for why the oleic acid concentration in cerebral
structures is not altered according to the oleic acid content of the diet. The nervous
system may selectively bind oleic acid, perhaps by specific, active transport mecha-
nisms across the blood brain barrier. Or it may be able to synthesise all of the oleic
acid that it needs, regardless of the dietary intake, as the brain contains an active
stearyl desaturase (Carreau et al., 1979). The concentration of this delta-9-desaturase
in the hippocampus of mice showing signs of accelerated ageing is low, which could
account for their observed behavioural disturbances (Kumar et al., 1999).

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Chromatographic Technique:
High-Performance Liquid Chromatog-
raphy (HPLC)
Jesús Lozano-SánchezIsabel Borrás-LinaresAgnes Sass-KissAntonio Segura-Car-
retero, in Modern Techniques for Food Authentication (Second Edition), 2018

5.4.1 Vegetable Oils

Chemical composition of edible vegetable oils extracted from oleaginous seeds and
fruits including essential -3, -6, and -9 fatty acids as well as many other minor
components belonging to a wide variety of phytochemical classes. There are three
different ways in which an oil can be misdescribed: the misdeclaration of one or all
the phases of the refining process, substituting all or a part of it with a similar but
cheaper oil, and declaring a false geographical or botanical origin. Major and minor
fractions are susceptible of analysis in order to determine the authenticity of the
sample (Fig. 10).

Fig. 10. Main adulteration of vegetable oils.

From a technological point of view, commercial differentiation of edible oils is based

on nonrefined and refined samples, due to the higher commercial value of the
former. Refining process is applied to vegetable oils for obtaining safer products
because this treatment eliminates undesirable compounds and produces highly
stable oils. The main steps of this process involve seed pretreatment, extraction,
degumming, neutralization, bleaching, and deodorization. Since the amount of the
components may be affected by conventional refining processes, chemical compo-
sition could be used as markers to determine the kind of treatment involved in the
elaboration process of edible oils (Dunford, 2004; Hidalgo and Zamora, 2006). Fig.
11 summarizes the main effect of refining process on vegetable oils composition.

Fig. 11. Effect of refining process on oil composition.

The refining process does not alter substantially the fatty acid composition, although
conjugated and trans fatty acids can be produced under specific conditions. The de-
odorization step causes the loss of volatile compounds, the thermal decomposition
of oxidation products and pigments, and the hydrolysis of conjugated polyenoic
compounds and triacylglycerols (TAGs). Concerning phospholipids, hydratable frac-
tion may be removed during water degumming while the nonhydratable one is
removed during acid degumming. With regard to lipophilic and hydrophilic phe-
nolics and other minor compounds, the final amount of these chemicals groups
are affected by degumming, neutralization, and bleaching. Degumming decreases
phytosterol and tocopherol contents in oils (Ferrari et al. 1997), neutralization gen-
erates a significant loss of phytosterols, tocopherols, o-diphenols, and flavonoids
(Verleyen et al. 2002; Garcia et al. 2006) and bleaching causes loss of carotenoids
and sterols (Verleyen et al. 2002; Rossi et al., 2001).

As it is described above, the refining process removes carotenoids and phenolic

compounds almost totally, while tocopherols and phytosterols are significantly
reduced. In addition, it is well known that several constituents of the vegetable oils
are very susceptible to heat (i.e., polyunsaturated fatty acids, minor compounds as
volatiles, and antioxidant molecules). Indeed, fraud by heat treatment, of either raw
material or resulting oil, may be detected by chemical and sensorial analysis (Gallina
Toschi et al., 2013). Concerning chemical parameters, some target compounds
could be monitoring in order to detect application of heat or refining steps in the
elaboration process (see Fig. 12, adapted from Gallina Toschi et al., 2013).
Fig. 12. Chemical markers of heating and refining process.

The second way in which an oil can be misdescribed is based on substituting all
or a part of it with a similar but cheaper oil. Olive and argan oils are the edible
oils which have been subjected to adulteration by cheaper oils due to its high
commercial profits. Health properties have been attributed to both, olive and argan
oils. Biological activities include bioactivity against inflammation, atherosclerosis,
metabolic syndrome, as well as antimicrobial activity and anticancer properties.
These reported properties have increased the illegal practices in the production
process and fraudulent commercialization, including the dilution with cheaper oil,
mainly with refined oilve oils, seed oils, and nut oils. Indeed, for virgin olive oils
(VOOs) it is estimated that in the European Union 4 million Euros per year are lost
because of this adulteration (Gallina Toschi et al., 2013).

Finally, the oil quality is also linked to botanical origin. For this reason, an important
issue is knowing the cultivars of oils as well as their location. Similar to other
food products, the European Community has introduced the denomination PDO,
PGI, and traditional specialty guaranteed (TSG) certifications, which allow certain
products to be labeled with the names of their geographical area of production.
Consequently, there is no doubt that the detection of adulteration in terms of the
misdeclaration of one or all the phases of the refining process, substituting all or a
part of it with a similar but cheaper oil, and declaring a false geographical or botanical
origin needs to be addressed in order to ensure the economic, health, and safety
quality of oil.

The main useful compounds of vegetable oils for detecting the authenticity of
oils and are triacylglycerols (TAGs). This chemical group has been used as marker
of genuine oils based on the equivalent carbon number (ECN). The experimental
determination of ECN is carried out by reverse-phase HPLC coupled to differential
refractometric detector methods. Several authors have applied this methodology
for determining authenticity of olive oils (EI-Hamdy and E1-Fizga, 1995; Cert and
Moreda, 2000; Moreda et al. 2003). EI-Hamdy and E1-Fizga (1995) measured VOO
authenticity based on the ECN42. For this purpose, soybean, sunflower, and corn oils
were used as adulterants and the detection limits based on ECNs of TAGs were estab-
lish at the level of 1%. Cert and Moreda (2000) combined TAG composition (ECN44)
determined by HPLC with chemometric tools to detect low levels of hazelnut oil in
olive oil. Moreda et al. (2003) developed a “Global method” applying an isocratic
elution with propionitrile for achieving a better resolution of critical pairs than in
official methods (ECN 42, 44, and 46). The proposed method has recently been
adopted by International Olive Council as an official method to determine olive
oils authenticity. The method and related limits are applied since January 1, 2014
(International Olive Council COI/T.20/Doc. no. 25 DEC- 22/100-V/2013, Madrid,
Spain 2013).

The analysis of this fraction has also been determined by coupling HPLC with other
detectors (Andrikopoulos, 2002a, b; Andrikopoulos et al., 2004; Buchgraber et al.,
2004; Kamm et al., 2001; Neff and Byrdwell, 1995). Fasciotti et al. (2010) proposed a
new analytical methodology combining HPLC-MS determination with PCA for the
quantitative evaluation of TAGs. The data shown that the proposed method was a
powerful tool to determine VOO adulteration with soybean at the level of 15% v/v.

With regard to minor components, tocopherols, carotenoids and chlorophylls, and

(phyto)sterols can be also used to detect adulteration (Tan, 1989; Psomiadou and
Tsimidou, 1998; Bonvehi et al., 2000; Dionisi et al., 1995). In this way, VOO au-
thenticity based on the concentration of , ß, and -tocopherols has been analyzed
by HPLC with fluorescence detection (Christodouleas et al. 2012). This research
showed that the ratio of these compounds was useful to detect percentages as low
as 1.5% and 3% of peanut and hazelnut oils in VOO, respectively (Christodouleas
et al. 2012). Puspitasari-Nienaber et al. (2002) have found that carotenoid/carotene
profile analyzed by HPLC coupled with thermal lens spectrometric (TLS) detector is
characteristic to control the authenticity of linseed, olive, sesame, and wheat germ
vegetable oils. The concentrations of total -carotene and -carotene together with
the ratio of trans to cis-isomers of -carotene are reliable indices for fast screening
of oils (Luterotti et al., 2002).

The other most studied fraction of oils and fats is sterols, which may be used to
detect authenticity. Recently, one of the most favorable analytical tools for analysis of
these compounds has been the online coupling of liquid chromatography coupled
with gas chromatography (LC-GC). The addition of solvent extracted oils to cold
pressed extra VOOs can be detected through investigation of free erythrodiol and
uvaol in olive oils. No sample preparation is needed prior to LC-GC analysis, except
filtration (Blanch et al., 1998). By determining filberton enantiomers online coupled
with HPLC-GC, the adulteration of olive oils with around 5%–10% of virgin and
refined hazelnut oils (del Castillo et al., 1998; Flores et al., 2006) could be detected.
However, it should be considered that filbertone may be partially or totally removed
upon gentle deodorization of the oil (Gallina Toschi et al., 2013).

Polyphenols have also been evaluated as possible fingerprint in oil samples. In

spite of phenolic composition of edible oils depends on the effect of some vari-
ables such as production process, pedoclimatic conditions, geographical area, and
variety, polyphenols could be used as markers of geographical area and cultivars.
Oil phenolic compounds belong to five main classes: phenolic acids, phenolic
alcohols, flavonoids, lignans, and secoiridoids (see Fig. 6). The synthesis of phenolic
compounds occurs through the shikimate pathway, phenylpropanoid metabolism,
and mevalonic acid pathway. The latter is responsible for secoiridoid synthesis, and is
typical of the Oleaceae family, which explains the presence of secoiridoids only in this
family of plants. Qualitative and quantitative characterization of these compounds
have been carried out by HPLC coupled to different detectors, and the results have
shown differences in phenolic composition which may be directly linked to their ge-
ographical origin and type of cultivars. According to the international ring test using
tyrosol and an unknown component as key compounds, HPLC analysis was suitable
to detect the addition of pressed hazelnut oil to VOO in 80% of the studied samples
(Zabaras and Gordon, 2004). Some authors have analyzed the phenolic profile of
olive oils obtained from different cultivar by HPLC-MS and reported significantly
different phenolic compositions among all varieties under study (Lozano-Sanchez et
al., 2010). Using the phenolic compounds belonging to simple phenols, secoiridoids,
lignans, and flavones, these authors constructed a latent Dirichlet allocation (LDA)
model capable of classifying the VOO samples according to their olive variety. In
addition, several works have pointed out the potential of the phenolic profile to
classify monovarietal olive oil according to their geographical area (Bakohuche et
al., 2013) (Fig. 13).
Fig. 13. Classification of VOO according to their botanical and geographical ori-
gins.Modified from Lozano-Sanchez, J., Segura-Carretero, A., Menendez, J.A., Oliv-
eras-Ferraros, C., et al., 2010. Prediction of extra virgin olive oil varieties through
their phenolic profile. Potential cytotoxic activity against human breast cancer
cells. J. Agric. Food Chem. 58, 9942–9955; Bakhouche, A., Lozano-Sanchez, J., Bel-
tran-Debon, R., Joven, J., 2013. Phenolic characterization and geographical clas-
sification of commercial Arbequina extra-virgin olive oils produced in southern
Catalonia. Food Res. Int. 50, 401–408.

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Omega-3 Polyunsaturated Fatty Acids

Added to Yogurt
Douglas Olson, Kayanush J. Aryana, in Yogurt in Health and Disease Prevention,
2017

7.1 Omega-3 Fatty Acid Classification and Structure

Fatty acids are carboxylic acids with a variable length aliphatic hydrocarbon chain.
Carbon atoms in the hydrocarbon chain are numbered starting at the carboxylic acid
end when using the systematic, or International Union of Pure and Applied Chem-
istry (IUPAC), nomenclature. The (omega) letter refers to the last carbon atom (the
carbon atom in the terminal methyl group) in a fatty acid when using the IUPAC rules
for numbering carbon atoms. Alternatively, carbon atoms are numbered starting
from the terminal methyl carbon atom when using the n-x nomenclature. Additional
details about naming fatty acids can be found at https://en.wikipedia.org/wiki/Fat-
ty_acid.

Fatty acids are classified as saturated, monounsaturated, and polyunsaturated

(PUFA). The location of the double bond in unsaturated fatty acids can be specified
using either the C-n notation (carbon numbering based on IUPAC rules) or the -n
notation (carbon numbering based on the n-x nomenclature). Different types of
omega unsaturated fatty acids exist including omega-3 fatty acids (also known as
-3 or n-3 fatty acids), omega-6 fatty acids (also known as -6 or n-6 fatty acids),
omega-7 fatty acids (also known as -7 or n-7 fatty acids), and omega-9 fatty acids
(also known as -9 or n-9 fatty acids).

Using the n-x carbon numbering system for specifying location of the first carbon
atom having a double bond but retaining the notation derived from IUPAC,
omega-3 fatty acids are PUFAs in which the first carbon–carbon double bond occurs
between the third and fourth carbon atoms and with one methylene (CH2) group
before the next carbon–carbon double bond. Therefore, the second carbon–carbon
double bond occurs between the sixth and seventh carbon atoms. Likewise, the
third carbon–carbon double bond occurs between the ninth and tenth carbon
atoms. Additional carbon–carbon double bonds may also be present closer to
the carboxyl group. The carbon–carbon double bonds are in the cis-configuration
(meaning that both hydrogen atoms bonded to these two carbon atoms are on
the same side of the double bond). The common omega-3 fatty acids are listed
at https://en.wikipedia.org/wiki/Omega-3_fatty_acid. The -linolenic acid (ALA, 18
carbons with 3 double bonds) (Fig. 7.1), eicosapentaenoic acid (EPA, 20 carbons with
5 double bonds) (Fig. 7.2), and docosahexaenoic acid (DHA, 22 carbons with 6 double
bonds) (Fig. 7.3) omega-3 fatty acids are the ones that are most important in human
nutrition and physiology. Docosapentaenoic acid (DPA, 22 carbons with 5 double
bonds) is structurally similar to EPA except for an extra two carbons in the chain.

Figure 7.1. The -linolenic acid (ALA, 18 carbons with 3 dou-

ble bonds) chemical structure. A public domain figure obtained at
https://en.wikipedia.org/wiki/Omega-3_fatty_acid#/media/File:ALAnumbering.svg.
Figure 7.2. The eicosapentaenoic acid (EPA, 20 carbons with 5
double bonds) chemical structure. A public domain figure ob-
tained at https://en.wikipedia.org/wiki/Omega-3_fatty_acid#/media/File:EPAnum-
bering.png.

Figure 7.3. The docosahexaenoic acid (DHA, 22 carbons with 6

double bonds) chemical structure. A public domain figure ob-
tained at https://en.wikipedia.org/wiki/Omega-3_fatty_acid#/media/File:DHAnum-
bering.png.

Omega-6 fatty acids are PUFAs in which the first carbon–carbon double bond occurs
between the sixth and seventh carbon atoms when using the same carbon number-
ing system as used for omega-3 fatty acids. Similar to omega-3 fatty acids, omega-6
fatty acids typically have one methylene (CH2) group before the next carbon–carbon
double bond and the carbon–carbon double bonds are in the cis-configuration. The
most recognized, as well as having the shortest chain, omega-6 fatty acid is linoleic
acid (18 carbons with 2 double bonds). A list of omega-6 fatty acids is given at
https://en.wikipedia.org/wiki/Omega-6_fatty_acid.

Omega-7 fatty acids and omega-9 fatty acids are other types of unsaturated fatty
acids and are not as well recognized by many as omega-3 fatty acids. The first
carbon–carbon double bond occurs between the seventh and eighth carbon atoms
in omega-7 fatty acids and between the ninth and tenth carbon atoms in omega-9
fatty acids. Omega-7 fatty acids have one carbon–carbon double bond. Palmitoleic
acid (16 carbon atoms with 1 double bond) and vaccenic acid (18 carbon atoms with
1 double bond) are the two most common omega-7 fatty acids, and a list of omega-7
fatty acids is provided at https://en.wikipedia.org/wiki/Omega-7_fatty_acid. Impor-
tant omega-9 fatty acids include oleic acid (18 carbon atoms with 1 double bond)
and erucic acid (22 carbon atoms with 1 double bond), and a list of omega-9 fatty
acids is provided at https://en.wikipedia.org/wiki/Omega-9_fatty_acid.

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Modulatory Role of Unsaturated Fatty

Acids in Immune Defense against Mi-
croorganisms
M.A. Puertollano, ... G.Á. de Cienfuegos, in Bioactive Food as Dietary Interventions
for Arthritis and Related Inflammatory Diseases, 2013

1.1 Dietary Lipids and Infection

Nutrient intake may be frequently considered as a critical determinant of immuno-
competence because of the impact of certain micronutrients and macronutrients
on immune system functions. Many investigations have reported the modulatory
role exerted by certain fatty acids on the immune system and the clinical benefits of
dietary lipid supplementation with fish oil or olive oil in both humans and animals.
As a result, diets containing fish oil or olive oil have been applied in the resolution,
or at least in the attenuation, of diseases characterized by an overactivation of
immune system, because unsaturated fatty acids (mainly n-3 or n-9 fatty acids)
reduced the levels of many biological mediators associated with the promotion
of the inflammatory events that participate in an inappropriate immune response.
Different studies have supported this claim by showing that n-3, n-6, or n-9 fatty
acids exert immunomodulatory effects (Kremer, 1996). However, human clinical
trials have been less conclusive. The reported reduction in the immune response
induced by the administration of these fats in the diet may have a detrimental effect
on host resistance and therefore can compromise host immunity against pathogens
(de Pablo and Alvarez de Cienfuegos, 2000). For obvious reasons, changes in the im-
mune resistance against infectious organisms have been studied in animal models
in which the administration of diets containing fish oil generally reduces the elimi-
nation of microbial pathogens from the liver or spleen and significantly decreases
survival during experimental infection (reviewed in Anderson and Fritschem, 2002).
Several reports have described the clinical consequences of dietary supplementation
with n-3 PUFAs, which are characterized by the suppression of immune system
functions. The analysis focused on the study of the action of fatty acids on immune
functions and modulation of resistance to infectious organisms has thrown up many
discrepancies that can be directly attributed to various factors including the type and
amount of food consumed, the feeding time before the challenge with the organism,
the dose, and the type and route of infection.

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Advancements in nutrition and nutri-

tional therapy
Elizabeth Koutsos • , ... Michael Scott Echols, in Current Therapy in Avian Medicine
and Surgery, 2016
Fatty acids
The omega series (primarily omegas 3, 6, and 9) fatty acids have been intensively
studied and recognized for their primary and secondary roles in many biochemical
reactions and health parameters. Depending on the specific form and the animal
in question, the omega series fatty acids are often considered essential as the
body must obtain either their precursor or final form from the diet. For example,
docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), also known as the
“fish oils,” are considered truly essential to domestic cats who cannot convert these
fatty acids from the plant-based precursor -linolenic acid (ALA). As a general rule
the more herbivorous the animal the better its conversion from ALA to DHA and/or
EPA. The converse is true of carnivorous animals who are generally poor converters.

Omega-6 series fatty acids (linoleic acid [LA] is the principle physiologic form and
comes primarily from plant-based sources and plant-eating animal tissue) often
have opposing functions to omega-3 series fats. Omega-9 series fatty acids (in-
cluding oleic acid and erucic acid) commonly come from plant oils and animal fat.
Omega-9 fatty acids are often not considered essential because many animals can
construct these fats from unsaturated fat. Studies on omega-3 and omega-6 fatty
acid supplementation are extensive in mammals. Additionally, there are numerous
studies on both fatty acid types in birds, primarily in poultry species. The value and
role(s) of omega-9 fatty acids in birds have yet to be clearly defined.

Omega series fatty acids are most often listed by their form (e.g., ALA, DHA, LA)
and in milligram amounts. Serving size and/or dose recommendations are often
included. These fatty acids may be packaged in gel capsules (preferred form for
stability reasons), gel sticks, dry powder, pump and pour-on bottles, and more. DHA
and EPA are highly unstable and currently best kept in gel capsules. All fatty acid
supplements should be stored in dark cool locations and in tightly sealed bottles or
capsules to slow oxidation.

With some exceptions, most studies on fatty acid quality pertain to contaminants.
In particular, persistent organic pollutants (POPs) are of greatest concern as these
toxic compounds bioaccumulate and biomagnify in animal tissues, particularly
marine species.19 While plants can also contain POPs, these organic compounds
are typically deposited on the leafy portions of the plants and are not bioaccumu-
lative and do not magnify as is common with predator species.19 POP exposure
is associated with a host of problems including endocrine disruptions; cancer;
and neurobehavioral, reproductive, and developmental disturbances in humans
and animals.19,20 Contamination with polychlorinated biphenyls, organochlorinated
pesticides, polybrominated diphenyl ethers, pristine, squalene, unresolved complex
mixtures, aryl hydrocarbon receptor agonist (digoxin-like), polychlorinated diben-
zo-p-dioxins/furans was noted in a number of studies of fish oils and omega-3 fatty
acid supplements.20,79-84 In 2004 ConsumerLab.com, an independent reviewer of
nutraceuticals, reported that 6 of 20 omega-3 fatty acid products did not contain
the label-stated amount of one or more essential fatty acids. The website stated “two
of the products that failed made claims on their labels that their ‘potency’ had been
‘tested’ or ‘verified’.”85 In a 2014 revised review of 30 omega-3 fatty acid supplements,
ConsumerLab.com reported that five products failed to meet basic quality testing.86

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Oleic Acid and Lung Injury

Cassiano F. Gonçalves-de-Albuquerque, ... Hugo C. Castro-Faria-Neto, in Hand-
book of Lipids in Human Function, 2016

Fatty Acid Definition and Origin

Fatty acids are carbon chains with a carboxyl group at the end of the molecule;
some of them are unsaturated fatty acids presenting double bounds. Concerning
polyunsaturated fatty acids (PUFAs), when the first double bond is found between
the third and the fourth carbon atom, they are called n-3 fatty acids. If the first
double bond is between carbons 6 and 7, they are n-6 fatty acids, and if the first
bond is between carbons 9 and 10, they are n-9 fatty acids. Fatty acids come from
the diet or are synthesized by tissues, representing 30–40% of total energy intake
in developed countries. Some of them, such as linoleic and linolenic acids, derive
only from the diet because they are essential fatty acids. Animals cannot introduce
double bonds above C9, but plants can. The most important dietary fatty acid
sources are vegetable oils, meat products, grains, and fish oils. The main saturated
fatty acid in animals and plants is palmitic acid (16:0), whereas stearic acid (18:0)
is found mainly in animals. Oleic acid (18:1n-9) is an unsaturated fatty acid in
plants and animals. Palmitoleic acid (16:1n-7) also occurs in animals and plants,
being a component of some seed oils. Linoleic acid (18:2n-6) is found in plant
lipids, and arachidonic acid (20:4n-6) is present in membrane phospholipids, being
a precursor of several signaling molecules such as prostaglandins, thromboxanes,
and leukotrienes (Catala, 2013). Animal tissues increase fatty acid synthesis from
glucose depending on the individual nutritional status. This normally occurs when
the circulating insulin level is augmented, inducing the transcription of lipogenic
enzymes (Ameer et al., 2014).

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New functional foods for age-related
diseases
D. Rivera, C. Obón, in Functional Foods, Ageing and Degenerative Disease, 2004

3.6.1 Simplifying dosage and processes

There is a strong tendency to reduce the time spent in processing food at home,
especially in Western countries. This has caused commercially viable initiatives that
tend to replace traditional food by nutritional complements that are supposed to be
at least as effective as the former. For instance Omegacoeur®, a mixture of different
natural oils enriched with 3, 6, and 9 fatty acids, is sold as a ‘Mediterranean
nutritional complement’ (Maixent et al., 2003) and presumably as an alternative to
olive oil.

The development of food products with ‘functional’ properties or health benefits can
be done in the form of dietary supplements or simply foods. Particular ingredients
provide the health benefits. The food or ingredient conferring health properties may
consist of the plants themselves, extracts thereof, or more purified components
(Schilter et al., 2003). Since the -linolenic acid (ALA) supply is found to be too low
in a French population study, Combe et al. (2003) recommended food enrichment
to increase the ALA intake. Vasiliopoulou and Trichopoulou (2003) suggested an
alternative approach: registering and standardising traditional foods could provide
an incentive for their reinstatement into the daily diet. The ‘organic’ approach is
more time consuming but it offers interesting alternatives. The use of sprouts grown
from various seeds including legumes, broccoli and sunflower seeds is presented by
Goodwin (2003) as a positive contribution to health, by suggesting they are produced
at home.

Humans can alter plant metabolism to favour the synthesis of a particular metabolite
of medicinal value (Cseke and Kaufman, 1999). For instance, there is an interest
in genetically engineering crops for herbicide resistance, by transferring genes for
this purpose but similar techniques can be applied to metabolic engineering of sec-
ondary pathways for valuable phytochemicals in food plants (Bais and Ravishankar,
2001). For instance, isoflavonoid biosynthesis in nonlegumes is intended to expand
the delivery of dietary iso- flavones and to develop new sources for the more complex
bioactive isoflavonoids (Dixon and Summer, 2003).

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Lipid emulsifiers and surfactants in
dairy and bakery products
H.M. Premlal Ranjith, U. Wijewardene, in Modifying Lipids for Use in Food, 2006

16.5 Future trends

There is wide recommendation to consume food containing polyunsaturated fat
and reduce consumption of those with saturated fatty acids. However, legislation
may restrict some products coming into the market due to health implications. In
general, the drive towards healthy eating could well develop a new generation of
products based on nutritive value and the wellbeing of the consumer. In the spreads
market, the products made from polyunsaturated fats have become well-established.
Inclusion of omega-3 fatty acids in spreads is getting popular due to its ability to
reduce blood serum lipids and to lower blood pressure and other health benefits.
Other lipids containing omega-6 and omega-9 fatty acids could be popular due
to health benefits related to heart diseases. The technology in the production of
table spreads is so well advanced that, together with the advances in lipid refining
technology, a new generation of spreads could emerge and capture this specific
market sector. More work is required to establish other economical methods to
produce cis-9, trans-11 CLA isomer for incorporation into more food products other
than spreads. Further investigations into possible use of suitable CLA precursor for
endogenous synthesis of CLA in humans would be beneficial, especially for those
who suffer from dietary restrictions. It is also important to be conscious of adverse
comments expressed in terms of calorie intake, trans fatty acids, cholesterol content,
etc. The reduced fat spreads are more popular compared to 80 % fat spreads.
Reduced fat spreads and low-fat spreads are also popular due to the fact that there
is some perceived financial advantage as a significant proportion of fat is replaced
with water. However, this perceived financial gain may be overshadowed by the cost
involved in the advanced processing technology and additional ingredient cost.

Milk is the starting material for a variety of food products including milk drinks,
creams and table spreads. Milk composition is affected due to seasonal changes
which have a direct effect on foaming characteristics, feathering in cream and
spreadability of yellow fats. Modifications to cows' feeding material and milk lipid
tempering have been successfully adjusted so that acceptable results can be obtained
to optimize the functional properties. Research work is yet to produce successful and
commercially viable methods to improve foaming characteristics of milk and cream
without having to use additives.

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Classes, Nomenclature, and Functions
of Lipids and Lipid-Related Molecules
and the Dietary Lipids
Daniel Gyamfi, ... Stephen Owusu, in The Molecular Nutrition of Fats, 2019

5.1 Saturated and Unsaturated Fatty Acids

Dietary lipids contain a lot of fatty acids, which are usually straight-chain even-num-
bered hydrocarbon molecules, saturated or unsaturated. As mentioned previously,
the unsaturated ones can be monounsaturated or polyunsaturated. Cyclic fatty acids
may also occur in diets, although they may be negligible (Pokorny and Dostalova,
2009). Saturated fatty acids that can be found in the diet are many and include
butanoic, hexanoic, octanoic, and decanoic acids. Unsaturated fatty acids taken into
the body exclusively contain double bonds. Those with triple bonds are not found in
diets (Pokorny and Dostalova, 2009). Examples of unsaturated fatty acids contained
in diets include the monounsaturated oleic acid, the dienoic (containing two double
bonds) linoleic acid, and the trienoic (containing three double bonds) linolenic acid.
From the nomenclature of fatty acids, we realized that omega notation is also used.
This notation creates the omega series where we have omega 3, omega 6, and omega
9 fatty acids. The monounsaturated fatty acids are of the omega 9 series, whereas
the polyunsaturated ones are the omega 3 and omega 6 fatty acids from which the
essential fatty acids originate.

Linoleic acids belonging to the omega 6 series are usually abundant in seeds of
most plants and vegetable oils (Rodrigo and Alfonso, 2013). They have double bonds
at carbon-6 and carbon-9. Linolenic acids have double bonds at carbons-3, -6,
and -9 and have larger quantities in green leafy vegetables (Rodrigo and Alfonso,
2013). Both linoleic and linolenic acids can be metabolized to other fatty acids that
are of longer lengths; arachidonic acid, for instance, can be obtained from the
metabolism of linoleic acid, whereas eicosapentaenoic and docosahexaenoic acids
can be obtained from linolenic acid metabolism (Thickitt and Clissold, 1994). There
is the need to maintain the right balance between omega 6 and omega 3 fatty acids
for overall quality health of humans (Simopoulos, 2010, 2011; Kang, 2003). Adequate
balance has been found to help in brain development and decrease the incidence of
certain diseases such as arthritis, cancer, and diabetes (Simopoulos, 2010). Omega
3 fatty acids have obtained an enviable position in the promotion of good health
(Simopoulos, 1991). Omega 3 fatty acid–containing diets include fish oil, whereas
omega 6 fatty acid–containing diets include safflower oil and corn (Othman, 2007).
> Read full chapter

Volume 2
Elina Zailer, in Encyclopedia of Food Chemistry, 2019

Fatty Acid Distribution by 13C NMR Spectroscopy

The 13C NMR spectroscopy provides information on the chemical structure of the
TAGs and FAs showing an individual signal for each carbon. The 13C NMR spectra
can be compared with chromatograms where each signal can be assigned to an
appropriate substance. Fig. 8 illustrates a typical 600 MHz 13C NMR spectrum of
walnut oil. In the spectrum four main regions can be identified: carbonyl region (
174–172 ppm), olefinic signals ( 134–126 ppm), glycerol region ( 74–60 ppm),
and aliphatic region ( 35–19 ppm). Since the position of the double bond within
a FA causes an anisotropic shift of the neighbored carbon atoms, -3 as well as
-6,  -7, -9 and saturated FAs can be identified in highly resolved 13C NMR spectra
by their separated signals. By normalizing all signals of the same carbon group to
100, the molar ratio of each FA can be determined. In Fig. 9 the FA distribution of
a linseed oil is analyzed by using deconvolution for quantification. The results show
that the analyzed linseed oil consists of 58.1% -3, 14.9%  -6, 0.2% -7, 17.5% -9
and 9.2% saturated FA. Since the chemical structure of saturated FAs differs only
in the chain length, signals of individual saturated FAs cannot be separated. Thus,
saturated FAs are quantified in total.

Fig. 8. 600 MHz 13C NMR spectrum of walnut oil.

Fig. 9. 600 MHz 13C NMR spectrum of linseed oil, terminal methyl group.

Besides the general FA distribution, the 13C NMR spectroscopy provides information
on the regiospecific distribution of FAs in TAGs. Since the anisotropy makes the
carbonyl signals sensitive to double bonds within the FA chain, carbonyl signals of
a neighboring single and double bonds show a difference of the chemical shift of
approx. 0.5 ppm. This effect decreases according to the distance to the next double
bond. A signal separation is still possible at a double bond distance up to eleven
carbon atoms in the chain. Thus, the carbonyl region is very sensitive for regiose-
lective analysis. Distinction of sn-1/3 and sn-2 are possible for TAGs, phospholipids
and glycolipids (Fig. 10). Free and esterified FAs are also determined by evaluating
the carbonyl region. Here, we can distinguish between total free (FFA) and total
esterified FAs including mono-, di- and triacylglycerides. By integrating both regions
and normalizing them to 100, the molar ratio (in %) of free and esterified FAs is
determinable. Furthermore, individual FFAs are assigned, as presented in Fig. 11.
After methylation the total content of individual FAs can be examined, irrespective
of whether they existed in the free or esterified form in the lipid before (Fig. 11).
 Fig. 10. 600 MHz 13C NMR spectrum of a vegetable oil, carbonyl group.

Fig. 11. 600 MHz 13C NMR spectra of a fish oil, before (bottom) and after methylation
(top).

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