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org/wiki/Omega-3_fatty_acid

Omega-3 fatty acid

From Wikipedia, the free encyclopedia

n−3 fatty acids (popularly referred to as ω−3 fatty acids or omega-3 Types of fats in food
fatty acids) are a family of unsaturated fatty acids that have in
common a final carbon–carbon double bond in the n−3 position; that Unsaturated fat
is, the third bond from the methyl end of the fatty acid. Monounsaturated fat
Polyunsaturated fat
Important nutritionally-essential n−3 fatty acids are: α-linolenic acid Trans fat
(ALA), eicosapentaenoic acid (EPA), and docosahexaenoic acid Omega fatty acids:
(DHA), all of which are polyunsaturated. The human body cannot ω−3
synthesize n−3 fatty acids de novo, but it can form 20-carbon ω−6
unsaturated n−3 fatty acids (like EPA) and 22-carbon unsaturated n−3 ω−9
fatty acids (like DHA) from the eighteen-carbon n−3 fatty acid Saturated fat
α-linolenic acid. These conversions occur competitively with n−6 fatty Interesterified fat
acids, which are essential closely related chemical analogues that are
derived from linoleic acid. Both the n−3 α-linolenic acid and n−6 See also
linoleic acid are essential nutrients which must be obtained from food.
Synthesis of the longer n−3 fatty acids from linolenic acid within the Fatty acid
body is competitively slowed by the n−6 analogues. Thus Essential fatty acid
accumulation of long-chain n−3 fatty acids in tissues is more effective
when they are obtained directly from food or when competing amounts of n−6 analogs do not greatly exceed
the amounts of n−3.

Contents
1 History
2 Chemistry
2.1 List of n−3 fatty acids
3 Biological significances
4 Health benefits
4.1 Cancer
4.2 Cardiovascular disease
4.3 Immune function
4.4 Brain health
4.5 Rheumatoid arthritis
5 Health risks
5.1 Cardiac risk
6 Research frontiers
6.1 Developmental differences
6.2 Low birth weight
6.3 Psychiatric disorders
7 Dietary sources
7.1 Daily values
7.2 Fish
7.3 Flax

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7.4 Botanical sources of n−3 fatty acids

7.5 Eggs
7.6 Meat
7.7 Other sources
8 The n−6 to n−3 ratio
9 Conversion efficiency of ALA to EPA and DHA
10 See also
11 Notes and references
11.1 Additional sources
12 Further reading
13 External links

History
Although omega-3 fatty acids have been known as essential to normal growth and health since the 1930s,
awareness of their health benefits has dramatically increased in the past few years. [1]

The heart-health benefits of the long-chain omega-3 fatty acids — DHA and EPA omega-3 — are the best
known. These benefits were discovered in the 1970s by researchers studying the Greenland Eskimos. The
Greenland Eskimos consumed large amounts of fat from seafood, but displayed virtually no cardiovascular
disease. The high level of omega-3 fatty acids consumed by the Eskimos reduced triglycerides, heart rate,
blood pressure, and atherosclerosis.

On September 8, 2004, the U.S. Food and Drug Administration gave "qualified health claim" status to
eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) n−3 fatty acids, stating that "supportive but
not conclusive research shows that consumption of EPA and DHA [n−3] fatty acids may reduce the risk of
coronary heart disease."[2] This updated and modified their health risk advice letter of 2001 (see below).
Currently regulatory agencies do not accept that there is sufficient evidence for any of the other suggested
benefits of DHA and EPA other than for cardiovascular health, and further claims should be treated with
caution.

The Canadian Government has recognized the importance of DHA omega-3 and permits the following
biological role claim for DHA: "DHA, an omega-3 fatty acid, supports the normal development of the brain,
eyes and nerves." [3]

As the importance of omega-3 fatty acids to health has received increasing awareness, the number of food
products enriched in omega-3 fatty acids has increased. Many companies add fish oil or flax oil into their
final product to enrich it in omega-3 fatty acids. Some animal products, such as milk and eggs, can be
naturally enriched for omega-3 fatty acids by feeding the animals a diet that is rich in omega-3 fatty acids.

Chemistry

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The term n−3 (also called ω−3 or omega-3)

signifies that the first double bond exists as the
third carbon-carbon bond from the terminal
methyl end (n) of the carbon chain.
n−3 fatty acids which are important in human
nutrition are: α-linolenic acid (18:3, n−3;
ALA), eicosapentaenoic acid (20:5, n−3;
EPA), and docosahexaenoic acid (22:6, n−3;
DHA). These three polyunsaturates have either
3, 5 or 6 double bonds in a carbon chain of 18,
20 or 22 carbon atoms, respectively. All double
bonds are in the cis-configuration, i.e. the two
hydrogen atoms are on the same side of the
double bond.
Chemical structure of alpha-linolenic acid (ALA), an essential
n−3 fatty acid, (18:3∆9c,12c,15c, which means a chain of 18
carbons with 3 double bonds on carbons numbered 9, 12 and
15). Although chemists count from the carbonyl carbon (Blue
Numbering), physiologists count from the n (ω) carbon (red
numbering). Note that from the n end (diagram right), the first
double bond appears as the third carbon-carbon bond (line
segment), hence the name "n−3". This is explained by the fact
that the n end is almost never changed during physiologic
transformations in the human body, as it is more stable
energetically, and other carbohydrates compounds can be
synthesized from the other carbonyl end, for example in
glycerides, or from double bonds in the middle of the chain.

Most naturally-produced fatty acids (created or

transformed in animalia or plant cells with an
even number of carbon in chains) are in
cis-configuration where they are more easily Chemical structure of eicosapentaenoic acid (EPA).
transformable. The trans-configuration results
in much more stable chains that are very
difficult to further break or transform, forming
longer chains that aggregate in tissues and
lacking the necessary hydrophilic properties. Chemical structure of docosahexaenoic acid (DHA).
This trans-configuration can be the result of
the transformation in alkaline solutions, or of the action of some bacterias that are shortening the carbonic
chains. Natural transforms in vegetal or animal cells more rarely affect the last n−3 group itself. However,
n−3 compounds are still more fragile than n−6 because the last double bond is geometrically and electrically
more exposed, notably in the natural cis configuration.

List of n−3 fatty acids

This table lists several different names for the most common n−3 fatty acids found in nature.

Common name Lipid name Chemical name

α-Linolenic acid (ALA)
Stearidonic acid (STD)
Eicosatrienoic acid (ETE)
Eicosatetraenoic acid (ETA)
Eicosapentaenoic acid (EPA)
Docosapentaenoic acid (DPA),
Clupanodonic acid
Docosahexaenoic acid (DHA)
Tetracosapentaenoic acid
16:3 (n−3) all-cis-7,10,13-hexadecatrienoic acid
18:3 (n−3) all-cis-9,12,15-octadecatrienoic acid
18:4 (n−3) all-cis-6,9,12,15-octadecatetraenoic acid
20:3 (n−3) all-cis-11,14,17-eicosatrienoic acid
20:4 (n−3) all-cis-8,11,14,17-eicosatetraenoic acid
20:5 (n−3) all-cis-5,8,11,14,17-eicosapentaenoic acid
22:5 (n−3) all-cis-7,10,13,16,19-docosapentaenoic acid
22:6 (n−3) all-cis-4,7,10,13,16,19-docosahexaenoic acid
24:5 (n−3) all-cis-9,12,15,18,21-docosahexaenoic acid

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Tetracosahexaenoic acid (Nisinic acid) 24:6 (n−3) all-cis-6,9,12,15,18,21-tetracosenoic acid

Biological significances
The biological effects of the n−3 are largely mediated by their interactions with the n−6 fatty acids;
see Essential fatty acid interactions for detail.

A 1992 article by biochemist William E.M. Lands[4] provides an overview of the research into n−3 fatty
acids, and is the basis of this section.

The 'essential' fatty acids were given their name when researchers found that they were essential to normal
growth in young children and animals. (Note that the modern definition of 'essential' is more strict.) A small
amount of n−3 in the diet (~1% of total calories) enabled normal growth, and increasing the amount had
little to no additional effect on growth.

Likewise, researchers found that n−6 fatty acids (such as γ-linolenic acid and arachidonic acid) play a
similar role in normal growth. However, they also found that n−6 was "better" at supporting dermal integrity,
renal function, and parturition. These preliminary findings led researchers to concentrate their studies on
n−6, and it was only in recent decades that n−3 has become of interest.

In 1963 it was discovered that the n−6 arachidonic acid was converted by the body into pro-inflammatory
agents called prostaglandins. By 1979 more of what are now known as eicosanoids were discovered:
thromboxanes, prostacyclins and the leukotrienes. The eicosanoids, which have important biological
functions, typically have a short active lifetime in the body, starting with synthesis from fatty acids and
ending with metabolism by enzymes. However, if the rate of synthesis exceeds the rate of metabolism, the
excess eicosanoids may have deleterious effects. Researchers found that n−3 is also converted into
eicosanoids, but at a much slower rate. Eicosanoids made from n−3 fats are often referred to as
anti-inflammatory, but in fact they are just less pro-inflammatory than those made from n−6 fats. If both n−3
and n−6 are present, they will "compete" to be transformed, so the ratio of n−3:n−6 directly affects the type
of eicosanoids that are produced.

This competition was recognized as important when it was found that thromboxane is a factor in the
clumping of platelets, which leads to thrombosis. The leukotrienes were similarly found to be important in
immune/inflammatory-system response, and therefore relevant to arthritis, lupus, and asthma. These
discoveries led to greater interest in finding ways to control the synthesis of n−6 eicosanoids. The simplest
way would be by consuming more n−3 and fewer n−6 fatty acids.

Health benefits
The 18 carbon α-linolenic acid has not been shown to have the same cardiovascular benefits as DHA or
EPA. Currently there are many products on the market which claim to contain health promoting 'omega 3',
but contain only α-linolenic acid (ALA), not EPA or DHA. These products contain mainly higher plant oils
and must be converted by the body to create DHA and therefore considered less efficient. DHA and EPA
are made by microalgae that live in seawater. These are then consumed by fish and accumulate to high levels
in their internal organs. If a person is concerned about mercury and oceanborne contaminants in fish, DHA
can be produced directly from microalgae as a vegetarian source. People with certain circulatory problems,
such as varicose veins, benefit from fish oil because it contains the EPA and DHA derived from microalgae.
Fish oil stimulates blood circulation, increases the breakdown of fibrin, a compound involved in clot and scar
formation, and additionally has been shown to reduce blood pressure.[5][6] There is strong scientific
evidence that n−3 fatty acids reduce blood triglyceride levels[7][8][9][10] and regular intake reduces the risk

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of secondary and primary heart attack.[11][12][13][14]

Some benefits have been reported in conditions such as rheumatoid arthritis[15][16] and cardiac arrhythmias.
[17][18][19]

There is preliminary evidence that n-3 fatty acids supplementation might be helpful in cases of
depression[20][21] and anxiety.[22][23] Studies report highly significant improvement from n-3 fatty acids
supplementation alone and in conjunction with medication.[24]

Some research suggests that fish oil intake may reduce the risk of ischemic and thrombotic stroke.[25][26][27]
However, very large amounts may actually increase the risk of hemorrhagic stroke (see below). Lower
amounts are not related to this risk,[27] 3 grams of total EPA/DHA daily are considered safe with no
increased risk of bleeding involved[28] and many studies used substantially higher doses without major side
effects (for example: 4.4 grams EPA/2.2 grams DHA in 2003 study).[20]

Cancer

Several studies report possible anti-cancer effects of n−3 fatty acids (particularly breast, colon and prostate
cancer).[29][30][31] Omega-3 fatty acids reduced prostate tumor growth, slowed histopathological
progression, and increased survival[32]. Among n-3 fatty acids [omega-3], neither long-chain nor short-chain
forms were consistently associated with breast cancer risk. High levels of docosahexaenoic acid, however,
the most abundant n-3 PUFA [omega-3] in erythrocyte membranes, were associated with a reduced risk of
breast cancer.[33]. A 2009 trial found that a supplement of eicosapentaenoic acid helped cancer patients
retain muscle mass.[34]

A 2006 report in the Journal of the American Medical Association concluded that their review of literature
covering cohorts from many countries with a wide variety of demographic concluded that there was no link
between n−3 fatty acids and cancer.[35] This is similar to the findings of a review by the British Medical
Journal of studies up to February 2002 that failed to find clear effects of long and shorter chain n−3 fats on
total mortality, combined cardiovascular events and cancer.[36]

Cardiovascular disease

In 1999, the GISSI-Prevenzione Investigators reported in the Lancet, the results of major clinical study in
11,324 patients with a recent myocardial infarction. Treatment 1 gram per day of n−3 fatty acids reduced
the occurrence of death, cardiovascular death and sudden cardiac death by 20%, 30% and 45%
respectively.[37] These beneficial effects were seen already from three months onwards.[38]

In April 2006, a team led by Lee Hooper at the University of East Anglia in Norwich, UK, published a
review of almost 100 separate studies into n−3 fatty acids, found in abundance in oily fish. It concluded that
they do not have a significant protective effect against cardiovascular disease.[39] This meta-analysis was
controversial and stands in stark contrast with two different reviews also performed in 2006 by the American
Journal of Clinical Nutrition[40] and a second JAMA review[41] that both indicated decreases in total
mortality and cardiovascular incidents (i.e. myocardial infarctions) associated with the regular consumption
of fish and fish oil supplements. In addition n−3 has been shown to reduce symptoms of other mental
disorders such as aggression and ADHD.[42][43]

Several studies published in 2007 have been more positive. In the March 2007 edition of the journal
Atherosclerosis, 81 Japanese men with unhealthy blood sugar levels were randomly assigned to receive
1800 mg daily of eicosapentaenoic acid (EPA — an n−3 essential fatty acid from fish oil) with the other half
being a control group. The thickness of the carotid arteries and certain measures of blood flow were

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measured before and after supplementation. This went on for approximately two years. A total of 60 patients
(30 in the EPA group and 30 in the control group) completed the study. Those given the EPA had a
statistically significant decrease in the thickness of the carotid arteries along with improvement in blood
flow. The authors indicated that this was the first demonstration that administration of purified EPA
improves the thickness of carotid arteries along with improving blood flow in patients with unhealthy blood
sugar levels.[44]

In another study published in the American Journal of Health System Pharmacy March 2007, patients with
high triglycerides and poor coronary artery health were given 4 grams a day of a combination of EPA and
DHA along with some monounsaturated fatty acids. Those patients with very unhealthy triglyceride levels
(above 500 mg/dl) reduced their triglycerides on average 45% and their VLDL cholesterol by more than
50%. VLDL is a bad type of cholesterol and elevated triglycerides can also be deleterious for cardiovascular
health.[45]

Another study on the benefits of EPA was published in The Lancet in March 2007. This study involved over
18,000 patients with unhealthy cholesterol levels. The patients were randomly assigned to receive either
1,800 mg a day of EPA with a statin drug or a statin drug alone. The trial went on for a total of five years. It
was found at the end of the study those patients in the EPA group had superior cardiovascular function.
Non-fatal coronary events were also significantly reduced in the EPA group. The authors concluded that
EPA is a promising treatment for prevention of major coronary events, especially non-fatal coronary
events.[46]

Similar to those who follow a Mediterranean diet, Arctic-dwelling Inuit - who consume high amounts of n−3
fatty acids from fatty fish - also tend to have higher proportions of n−3, increased HDL cholesterol and
decreased triglycerides (fatty material that circulates in the blood) and less heart disease. Eating walnuts (the
ratio of n−3 to n−6 is circa 1:4 respectively[47]) was reported to lower total cholesterol by 4% relative to
controls when people also ate 27% less cholesterol.[48]

A study carried out involving 465 women showed serum levels of eicosapentaenoic acid is inversely related
to the levels of anti-oxidized-LDL antibodies. Oxidative modification of LDL is thought to play an important
role in the development of atherosclerosis.[49]

Immune function

Another study regarding fish oil was published in the Journal of Nutrition in April 2007. Sixty four healthy
Danish infants from nine to twelve months of age received either cow's milk or infant formula alone or with
fish oil. It was found that those infants supplemented with fish oil had improvement in immune function
maturation with no apparent reduction in immune activation.[50]

Brain health

There was yet another study on n−3 fatty acids published in the April 2007 Journal of Neuroscience. A
group of mice were genetically modified to develop accumulation of amyloid and tau proteins in the brain
similar to that seen in people with poor memory. The mice were divided into four groups with one group
receiving a typical American diet (with high ratio of n−6 to n−3 fatty acids being 10 to 1). The other three
groups were given food with a balanced 1 to 1 n−6 to n−3 ratio and two additional groups supplemented
with DHA plus long chain n−6 fatty acids. After three months of feeding, all the DHA supplemented groups
were noted to have a lower accumulation of beta amyloid and tau protein. Some research suggests that these
abnormal proteins may contribute to the development of memory loss in later years.[51]

There is also a study published regarding n−3 supplementation in children with learning and behavioral
problems. This study was published in the April 2007 edition of the Journal of the Developmental and

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Behavioral Pediatrics (5), where 132 children, between the ages of seven to twelve years old, with poor
learning, participated in a randomized, placebo-controlled, double-blinded interventional trial. A total of 104
children completed the trial. For the first fifteen weeks of this study, the children were given polyunsaturated
fatty acids (n−3 and n−6, 3000 mg a day), polyunsaturated fatty acids plus multi-vitamins and minerals or
placebo. After fifteen weeks, all groups crossed over to the polyunsaturated fatty acids (PUFA) plus
vitamins and mineral supplement. Parents were asked to rate their children's condition after fifteen and thirty
weeks. After thirty weeks, parental ratings of behavior improved significantly in nine out of fourteen scales.
The lead author of the study, Dr. Sinn, indicated the present study is the largest PUFA trial to date with
children falling in the poor learning and focus range. The results support those of other studies that have
found improvement in poor developmental health with essential fatty acid supplementation.[45][46][50][51]
[52][53]

A study[54] examining whether omega-3 exerts neuroprotective action in Parkinson's disease found that it
did, using an experimental model, exhibit a protective effect (much like it did for Alzheimer's disease as
well). The scientists exposed mice to either a control or a high omega-3 diet from two to twelve months of
age and then treated them with a neurotoxin commonly used as an experimental model for Parkinson's. The
scientists found that high doses of omega-3 given to the experimental group completely prevented the
neurotoxin-induced decrease of dopamine that ordinarily occurs. Since Parkinson's is a disease caused by
disruption of the dopamine system, this protective effect exhibited could show promise for future research in
the prevention of Parkinson's disease.

Rheumatoid arthritis

Research in 2005 and 2006 has suggested that the in-vitro anti-inflammatory activity of n−3 acids translates
into clinical benefits. Cohorts of neck pain patients and of rheumatoid arthritis sufferers have demonstrated
benefits comparable to those receiving standard NSAIDs. Those who follow a Mediterranean-style diet tend
to have less heart disease, higher HDL ("good") cholesterol levels[55] and higher proportions of n−3 in tissue
highly unsaturated fatty acids.[56]

Health risks
In a letter published October 31, 2000,[57] the United States Food and Drug Administration Center for Food
Safety and Applied Nutrition, Office of Nutritional Products, Labeling, and Dietary Supplements noted that
known or suspected risks of EPA and DHA n−3 fatty acids may include the possibility of:

Increased bleeding if overused (normally over 3 grams per day) by a patient who is also taking aspirin
or warfarin. However, this is disputed.[58]
Hemorrhagic stroke (only in case of very large doses). [59]
Reduced glycemic control among diabetics.
An increase in concentration of LDL cholesterol in some individuals.

Subsequent advices from the FDA and national counterparts have permitted health claims associated with
heart health.

Cardiac risk

Persons with congestive heart failure, chronic recurrent angina or evidence that their heart is receiving
insufficient blood flow are advised to talk to their doctor before taking n−3 fatty acids. There have been
concerns if such persons take n−3 fatty acids or eating foods that contain them in substantial amounts.[60] In
a recent large study, n−3 fatty acids on top of standard heart failure therapy produced a small but

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statistically significant benefit in terms of mortality and hospitalization.[61]

In congestive heart failure, cells that are only barely receiving enough blood flow become electrically
hyperexcitable. This, in turn, can lead to increased risk of irregular heartbeats, which, in turn, can cause
sudden cardiac death. n−3 fatty acids seem to stabilize the rhythm of the heart by effectively preventing
these hyperexcitable cells from functioning, thereby reducing the likelihood of irregular heartbeats and
sudden cardiac death. For most people, this is obviously beneficial and would account for most of the large
reduction in the likelihood of sudden cardiac death. Nevertheless, for people with congestive heart failure,
the heart is barely pumping blood well enough to keep them alive. In these patients, n−3 fatty acids may
eliminate enough of these few pumping cells that the heart would no longer be able to pump sufficient blood
to live, causing an increased risk of cardiac death.[60]

Research frontiers
Developmental differences

Although not supported by current scientific evidence as a primary treatment for ADHD, autism, and other
developmental differences,[62][63] omega-3 fatty acids have gained popularity for children with these
conditions.[62] A 2004 Internet survey found that 29% of surveyed parents used essential fatty acid
supplements to treat children with autism spectrum disorders.[64]

Omega-3 fatty acids offer a promising complementary approach to standard treatments for ADHD and
developmental coordination disorder.[63] Fish oils appear to reduce ADHD-related symptoms in some
children.[63] Double blind studies have showed "medium to strong treatment effects of omega 3 fatty acids
on symptoms of ADHD" after administering amounts around 1 gram for three to six months.[42][43][52]

There is very little scientific evidence supporting the effectiveness of omega-3 fatty acids for autism
spectrum disorders.[65] One randomized controlled trial found that omega-3 fatty acids did not significantly
affect aberrant behavior in autistic children, and although the investigators noted reduced hyperactivity,[66]
their later reanalysis reported that the reduction was not statistically significant.[67]

Low birth weight

In a study of nearly 9,000 pregnant women, researchers found women who ate fish once a week during their
first trimester had 3.6 times less risk of low birth weight and premature birth than those who ate no fish. Low
consumption of fish was a strong risk factor for preterm delivery and low birth weight.[68] However,
attempts by other groups to reverse this increased risk by encouraging increased pre-natal consumption of
fish were unsuccessful.[69]

Psychiatric disorders

n−3 fatty acids are known to have membrane-enhancing capabilities in brain cells.[39] One medical
explanation is that n−3 fatty acids play a role in the fortification of the myelin sheaths. Not coincidentally,
n−3 fatty acids comprise approximately eight percent of the average human brain according to Dr. David
Horrobin, a pioneer in fatty acid research. Ralph Holman of the University of Minnesota, another major
researcher in studying essential fatty acids, who gave Omega-3 its name, surmised how n−3 components are
analogous to the human brain by stating that "DHA is structure, EPA is function."

A benefit of n−3 fatty acids is helping the brain to repair damage by promoting neuronal growth.[39] In a
six-month study involving people with schizophrenia and Huntington's disease who were treated with EPA

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or a placebo, the placebo group had clearly lost cerebral tissue, while the patients given the supplements had
a significant increase of grey and white matter.[70]

In the prefrontal cortex (PFC) of the brain, low brain n−3 fatty acids are thought to lower the dopaminergic
neurotransmission in this brain area, possibly contributing to the negative and neurocognitive symptoms in
schizophrenia. This reduction in dopamine system function in the PFC may lead to an overactivity in
dopaminergic function in the limbic system of the brain which is suppressively controlled by the PFC
dopamine system, causing the positive symptoms of schizophrenia. This is called the n−3 polyunsaturated
fatty acid/dopamine hypothesis of schizophrenia (Ohara, 2007). This mechanism may explain why n−3
supplementation shows effects against both positive, negative and neurocognitive symptoms in
schizophrenia.

Consequently, the past decade of n−3 fatty acid research has procured some Western interest in n−3 fatty
acids as being a legitimate 'brain food.' Still, recent claims that one's intelligence quotient, psychological tests
measuring certain cognitive skills, including numerical and verbal reasoning skills, are increased on account
of n−3 fatty acids consumed by pregnant mothers remain unreliable and controversial. An even more
significant focus of research, however, lies in the role of n−3 fatty acids as a non-prescription treatment for
certain psychiatric and mental diagnoses and has become a topic of much research and speculation.

In 1998, Andrew L. Stoll, MD and his colleagues at Harvard University conducted a small double-blind
placebo-controlled study in thirty patients diagnosed with bipolar disorder. Most subjects in this study were
already undergoing psychopharmacological treatment (e.g. 12 out of the 30 were taking lithium). Over the
course of four months, he gave 15 subjects capsules containing olive oil, and another 15 subjects capsules
containing nine grams of pharmaceutical-quality EPA and DHA. The study showed that subjects in the n−3
group were less likely to experience a relapse of symptoms in the four months of the study. Moreover, the
n−3 group experienced significantly more recovery than the placebo group. However, a commentary on the
Stoll study notes that the improvement in the n−3 group was too small to be clinically significant.[71] Though
Stoll believes that the 1999 experiment was not as optimal as it could have been and has accordingly pursued
further research, the foundation has been laid for more researchers to explore the theoretical association
between absorbed n−3 fatty acids and signal transduction inhibition in the brain.[72]

"Several epidemiological studies suggest covariation between seafood consumption and rates of mood
disorders. Biological marker studies indicate deficits in omega−3 fatty acids in people with depressive
disorders, while several treatment studies indicate therapeutic benefits from omega-3 supplementation. A
similar contribution of omega-3 fatty acids to coronary artery disease may explain the well-described links
between coronary artery disease and depression. Deficits in omega-3 fatty acids have been identified as a
contributing factor to mood disorders and offer a potential rational treatment approach."[73] In 2004, a study
found that 100 suicide attempt patients on average had significantly lower levels of EPA in their blood as
compared to controls.[74]

In 2006, a review of published trials in the American Journal of Clinical Nutrition found that "the evidence
available provides little support" for the use of fish or the n–3 long-chain polyunsaturated fatty acids
contained in them to improve depressed mood. The study used results of twelve randomized controlled trials
in its meta-analysis. The review recommended that "larger trials with adequate power to detect clinically
important benefits" be performed.[75] A further 2007 study published in the British Journal of Nutrition,
which was placebo-controlled and used 218 participants, found that increasing EPA and DHA in the diet
"was found not to have beneficial or harmful effects on mood in mild to moderate depression," confirming
previous meta-analysis "that there is an overall negligible benefit of n-3 UFA supplementation for depressed
mood". [76]

Dietary sources

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Daily values

As macronutrients, fats are not assigned recommended daily allowances. Macronutrients have AI
(Acceptable Intake) and AMDR (Acceptable Macronutrient Distribution Range) instead of RDAs. The AI
for n−3 is 1.6 grams/day for men and 1.1 grams/day for women[77] while the AMDR is 0.6% to 1.2% of total
energy.[78]

"A growing body of literature suggests that higher intakes of α-linolenic acid (ALA), eicosapentaenoic acid
(EPA), and docosahexaenoic acid (DHA) may afford some degree of protection against coronary heart
disease. Because the physiological potency of EPA and DHA is much greater than that for α-linolenic acid,
it is not possible to estimate one AMDR for all n−3 fatty acids. Approximately 10 percent of the AMDR can
be consumed as EPA and/or DHA."[78] There was insufficient evidence as of 2005 to set a UL (upper
tolerable limit) for n−3 fatty acids.[77]

A perceived risk of fish oil n−3 supplementation has been heavy metal poisoning by the body's accumulation
of traces of heavy metals, in particular mercury, lead, nickel, arsenic and cadmium as well as other
contaminants (PCBs, furans, dioxins), which potentially might be found especially in less-refined fish oil
supplements. However, in reality, heavy metal toxicity from consuming fish oil supplements is highly
unlikely. This is because heavy metals selectively bind with protein in the fish flesh rather than accumulate
in the oil. An independent test in 2006 of 44 fish oils on the US market found that all of the products passed
safety standards for potential contaminants.[79] The FDA recommends that total dietary intake of n−3 fatty
acids from fish not exceed 3 grams per day, of which no more than 2 grams per day are from nutritional
supplements.[2]

Historically, the Council for Responsible Nutrition (CRN) and the World Health Organization (WHO) have
published acceptable standards regarding contaminants in fish oil. The most stringent current standard is the
International Fish Oils Standard (IFOS). Fish oils that typically make this highest grade are those that are
molecularly distilled under vacuum, and have virtually no measurable level of contaminants (measured parts
per billion and parts per trillion).

n−3 supplementation in food has been a significant recent trend in food fortification, with global food
companies launching n−3 fortified bread, mayonnaise, pizza, yogurt, orange juice, children's pasta, milk,
eggs, confections and infant formula.

Fish

The most widely available source of EPA and DHA is cold water oily fish such as salmon, herring, mackerel,
anchovies and sardines. Oils from these fish have a profile of around seven times as much n−3 as n−6. Other
oily fish such as tuna also contain n−3 in somewhat lesser amounts. Consumers of oily fish should be aware
of the potential presence of heavy metals and fat-soluble pollutants like PCBs and dioxins which may
accumulate up the food chain.[80]

Even some forms of fish oil may not be optimally digestible. Of four studies that compare bioavailability of
the triglyceride form of fish oil vs. the ester form, two have concluded that the natural triglyceride form is
better, and the other two studies did not find a significant difference. No studies have shown the ester form
to be superior although it is cheaper to manufacture.[81][82]

Although fish is a dietary source of n−3 fatty acids, fish do not synthesize them; they obtain them from the
algae in their diet.

Flax

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Six times richer than most fish oils in n−3,[83] Flax (aka linseed)
(Linum usitatissimum) and its oil are perhaps the most widely
available botanical source of n−3. Flaxseed oil consists of
approximately 55% ALA (alpha-linolenic acid). Flax, like chia,
contains approximately three times as much n−3 as n−6.

15 grams of flaxseed oil provides ca. 8 grams of ALA, which is

converted in the body to EPA and then DHA at an efficiency of
2–15% and 2–5%, respectively.[84]

Botanical sources of n−3 fatty acids Flax seeds produce linseed oil, which has a
very high n−3 content
Table 1. n−3 content as the percentage of ALA in the seed
oil.[85]

Common name Alternative name Linnaean name % n−3

Chia chia sage Salvia hispanica 64
Kiwifruit Chinese gooseberry Actinidia chinensis 62
Perilla shiso Perilla frutescens 58
Flax linseed Linum usitatissimum 55
Lingonberry Cowberry Vaccinium vitis-idaea 49
Camelina Gold-of-pleasure Camelina sativa 36
Purslane Portulaca Portulaca oleracea 35
Black Raspberry Rubus occidentalis 33

Table 2. n−3 content as the percentage of ALA in the whole food.[86][87]

Common name Linnaean name % n−3

Flaxseed Linum usitatissimum 18.1
Butternuts Juglans cinerea 8.7
Hempseed Cannabis sativa 8.7
Walnuts Juglans regia 6.3
Pecan nuts Carya illinoinensis 0.6
Hazel nuts Corylus avellana 0.1

Eggs

Eggs produced by chickens fed a diet of greens and insects produce higher levels of n−3 fatty acids (mostly
ALA) than chickens fed corn or soybeans.[88] In addition to feeding chickens insects and greens, fish oils
may be added to their diet to increase the amount of fatty acid concentrations in eggs.[89] The addition of
flax and canola seeds to the diet of chickens, both good sources of alpha-linolenic acid, increases the
omega-3 content of the eggs.[90]

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Meat

The n−6 to n−3 ratio of grass-fed beef is about 2:1, making it a more useful source of n−3 than grain-fed
beef, which usually has a ratio of 4:1.[91]

In most countries, commercially available lamb is typically grass-fed, and thus higher in n−3 than other
grain-fed or grain-finished meat sources. In the United States, lamb is often finished (i.e. fattened before
slaughter) with grain, resulting in lower n−3.[92]

The omega-3 content of chicken meat may be enhanced by increasing the animals' dietary intake of grains
that are high in n−3, such as flax, chia, and canola.[93]

Other sources

Milk and cheese from grass-fed cows may also be good sources of n−3. One UK study showed that half a
pint of milk provides 10% of the recommended daily intake (RDI) of ALA, while a piece of organic cheese
the size of a matchbox may provide up to 88%".[94]

The microalgae Crypthecodinium cohnii and Schizochytrium are rich sources of DHA (22:6 n−3) and can be
produced commercially in bioreactors. This is the only source of DHA acceptable to vegans. Oil from brown
algae (kelp) is a source of EPA. Walnuts are one of few nuts that contain appreciable n−3 fat, with
approximately a 1:4 ratio of n−3 to n−6.[47] Acai palm fruit also contains n−3 fatty acids.

Omega-3 is also found in softgels in pharmacies and nowadays it is also found in combination with omega-6,
omega-9 and shark liver oil [95]

Some vegetables, too, contain a noteworthy amount of n-3, including strawberries and broccoli.

The n−6 to n−3 ratio

Clinical studies[4][96][97][98] indicate that the ingested ratio of n−6 to n−3 (especially Linoleic vs Alpha
Linolenic) fatty acids is important to maintaining cardiovascular health. However, two studies[99][100]
published in 2005 and 2007, found no such correlations in humans.

Both n−3 and n−6 fatty acids are essential, i.e. humans must consume them in the diet. n−3 and n−6
compete for the same metabolic enzymes, thus the n−6:n−3 ratio will significantly influence the ratio of the
ensuing eicosanoids (hormones), (e.g. prostaglandins, leukotrienes, thromboxanes etc.), and will alter the
body's metabolic function.[101] Generally, grass-fed animals accumulate more n−3 than do grain-fed animals
which accumulate relatively more n−6. Metabolites of n−6 are significantly more inflammatory (esp.
arachidonic acid) than those of n−3. This necessitates that n−3 and n−6 be consumed in a balanced
proportion; healthy ratios of n−6:n−3 range from 1:1 to 4:1.[102][103] Studies suggest that the evolutionary
human diet, rich in game animals, seafood and other sources of n−3, may have provided such a ratio.[96][104]

Typical Western diets provide ratios of between 10:1 and 30:1 - i.e., dramatically skewed toward n−6.[105]
Here are the ratios of n−6 to n−3 fatty acids in some common oils: canola 2:1, soybean 7:1, olive 3–13:1,
sunflower (no n−3), flax 1:3,[106] cottonseed (almost no n−3), peanut (no n−3), grapeseed oil (almost no
n−3) and corn oil 46 to 1 ratio of n−6 to n−3.[107]

Conversion efficiency of ALA to EPA and DHA

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It has been reported that conversion of ALA to EPA and further to DHA in humans is limited, but varies
with individuals.[108] Women have higher ALA conversion efficiency than men, probably due to the lower
rate of utilization of dietary ALA for beta-oxidation. This suggests that biological engineering of ALA
conversion efficiency is possible. Goyens et al. argue that it is the absolute amount of ALA, rather than the
ratio of n−3 and n−6 fatty acids, which affects the conversion.[109]

See also

List of n−3 fatty acids Naturopathic medicine Nutrition

n−6 fatty acid Camelina sativa Linseed oil
n−9 fatty acid Hempseed oil Chia
Essential fatty acid Cod liver oil Purslane
Essential fatty acid Fish oil Resolvins
interactions Flax Wakame
Grape seed oil Phytonutrients
Herbalism

Notes and references

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Additional sources

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Robson, A. 2006. "Shellfish view of omega-3 and sustainable fisheries (http://www.nature.com/doifinder

/10.1038/4441002d) ." Nature 444, 1002.
Robson, A. 2007. "Preventing the diseases of civilisation: shellfish, the omega-3:6 balance and human health
(http://www.cefas.co.uk/publications/shellfishnews/sfn23.pdf) ." Shellfish News 23, 25–27
Cunnane SC (2006) "Survival of the fattest: the key to human brain evolution." M S-MEDECINE
SCIENCES 22 (6–7): 659–663.
Bell, J.G., et al. 2004. "Essential fatty acids and phospholipase A2 in autistic spectrum disorders."
Prostaglandins Leukot.Essent.Fatty Acids 71(4):201–204.
Bartram, Thomas, 1998, Bartram's Encyclopedia of Herbal Medicine, p.271.
Ohara, K. "The n−3 polyunsaturated fatty acid/dopamine hypothesis of schizophrenia." Prog
Neuropsychopharmacol Biol Psychiatry. 2007 Mar 30;31(2):469–474.
Richardson, A.J., and M.A. Ross. 2000. "Fatty acid metabolism in neurodevelopmental disorder: a new
perspective on associations between attention-deficit/hyperactivity disorder, dyslexia, dyspraxia and the
autistic spectrum." Prostaglandins Leukot.Essent.Fatty Acids 63(1–2):1–9.
Young, G., and J. Conquer. 2005. "Omega-3 fatty acids and neuropsychiatric disorders." Reprod.Nutr.Dev
45(1):1–28.
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Scher, J., and Pillinger, M. "15d-PGJ2: The anti-inflammatory prostaglandin?" Clinical Immunology. 2005
Feb; 114(2):100–109

Further reading
Allport, Susan. The Queen of Fats: Why Omega-3s Were Removed from the Western Diet and What We
Can Do to Replace Them (http://worldcat.org/search?q=The+Queen+of+Fats%3A+Why+Omega-
3s+Were+Removed+from+the+Western+Diet+and+What+We+Can+Do+to+Replace+Them&qt=mozilla-
search) . University of California Press, September 2006. ISBN 978-0-520-24282-1.
Chow, Ching Kuang. Fatty Acids in Foods and Their Health Implications (http://worldcat.org
/oclc/25508943&referer=brief_results) . Routledge Publishing. New York, New York. 2001.
Clover, Charles. The End of the Line: How overfishing is changing the world and what we eat
(http://worldcat.org/oclc/67383509&referer=brief_results) . Ebury Press, London 2004. ISBN
0-09-189780-7
Stoll, Andrew L. The Omega-3 Connection (http://worldcat.org/search?q=The+Omega-3+Connection&
fq=ap%3AAndrew+L+Stoll&qt=facet_ap%3A) . Simon & Schuster 2001. ISBN 0-684-87138-6, ISBN
0-684-87139-4 (paperback).
Erasmus, Udo. Fats That Heal, Fats That Kill (http://worldcat.org
/search?q=Fats+That+Heal%2C+Fats+That+Kill&qt=mozilla-search) . 3rd ed. Burnaby (BC): Alive Books;
1993.
Boyd, Hillary & Basant, Puri K. The Natural Way to Beat Depression: the groundbreaking discovery of
EPA to change your life. (http://worldcat.org/oclc/59305855) London. Hodder and Stoughton. 2004. ISBN
0-340-82497-2
Tribole, Evelyn. "The Ultimate Omega-3 Diet (http://worldcat.org/oclc/77520775&referer=brief_results) "
New York. McGraw-Hill. 2007 ISBN 13:978-0-07-146986-9
Lands, William E.M. "Fish, Omega-3 and Human Health" Champaign. AOCS Press. 2005 ISBN
1-893997-81-2
Smithers, Lois. The Food Industry's Greed (http://www.myproductalert.com/inflammation.html) . How
Misleading Labeling of Omega-3 Foods Undermines American Health.

External links
American Heart Assoc "Fish & Omega-3 Fatty Acids" (http://www.americanheart.org
/presenter.jhtml?identifier=4632)
Omega-3 Prevents Macular Degeneration (http://www.amdsupport.ca/articles/86/1/Omega-3-Fatty-Acids-
and-the-Prevention-of-Macular-Degeneration/Page1.html)
Further topics and latest scientific research: DHA/EPA Omega-3 Institute (http://www.dhaomega3.org)
BBC News report: Oily fish helps cut inflammation (http://news.bbc.co.uk/2/hi/health/4325679.stm) , March
12, 2005.

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Omega-3 fatty acid - Wikipedia, the free encyclopedia http://en.wikipedia.org/wiki/Omega-3_fatty_acid

University of Maryland Medical Center, omega-3 Fatty Acids (http://www.umm.edu/altmed

/ConsSupplements/Omega3FattyAcidscs.html)
Durham Research: Using Fatty Acids for Enhancing Classroom Achievement (http://www.durhamtrial.org/)
Website for the Durham Schools Trial, trial on the effects of fatty acids with children who were under
performing in class. Funded by the Durham City Council and Oxford University. Their initial results
(http://pediatrics.aappublications.org/cgi/content/abstract/115/5/1360) (also available on durhamtrial.org
(http://durham.cergis.com/default.aspx?pid=228) ) were published in May 2005.
Big Pharma And Pill Peddlers (http://www.badscience.net/2006/09/big-pharma-and-pill-peddlers/) Read
criticism of the above mentioned Durham 'trial' by a columnist for the Guardian at badscience.net
(http://www.badscience.net) September 2006
Essential (Omega-3 and Omega-6) Fatty Acids: The Linus Pauling Institute Micronutrient Information Center
(http://lpi.oregonstate.edu/infocenter/othernuts/omega3fa/)
Simopoulos, AP The importance of the ratio of omega-6/omega-3 essential fatty acids.
(http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12442909&
dopt=Abstract)
Letter Responding to a Request to Reconsider the Qualified Claim for a Dietary Supplement Health Claim
for Omega-3 Fatty Acids and Coronary Heart Disease (http://www.cfsan.fda.gov/~dms/ds-ltr28.html)
MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid
(http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-fishoil.html)
Another reason why men like curves (http://www.telegraph.co.uk
/news/main.jhtml;jsessionid=NOC54WM2O44VLQFIQMFCFGGAVCBQYIV0?xml=/news/2007/11/12
/ncurves112.xml) (Daily Telegraph) Omega-3 credited with shaping a woman's figure to be more attractive
to men.
Omega Today: Taking a look at the natural benefits of Omega-3's (http://www.omegatoday.com/)
Omega-3 News and Information Resource (http://www.omegaxl.com/news/index.php)
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