Omega-3 Fatty Acid - Wikipedia, The Free Encyclopedia

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  • 8/8/2019 Omega-3 Fatty Acid - Wikipedia, The Free Encyclopedia

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    ga-3 fatty acid - Wikipedia, the free encyclopedia

    //en.wikipedia.org/wiki/Omega-3_fatty_acid[12/15/2014 10:36:25 PM]

    Omega-3 fatty acid

    Types of fats in food

    Unsaturated fat

    Monounsaturated fat

    Polyunsaturated fat

    Trans fat

    Omega numbering:

    ω−3

    ω−6

    ω−7

    ω−9

    Saturated fat

    Interesterified fat

    See also

    Fatty acid 

    Essential fatty acid 

     V · T · E

    From Wikipedia, the free encyclopedia

     

    Omega-3 fatty acids (also called ω-3 fatty acids or n-3 fatty acids[1])

     are polyunsaturated fatty acids  (PUFAs) with a double bond   (C=C) at

     the third carbon atom from the end of the carbon chain.[2] The fatty

     acids have two ends, the carboxylic acid   (-COOH) end, which is

     considered the beginning of the chain, thus "alpha", and the methyl

     (CH3) end, which is considered the "tail" of the chain, thus "omega."

     The nomenclature of the fatty acid is taken from the location of the first

     double bond, counted from the methyl end  , that is, the omega (ω-) or 

     the n- end.

    The three types of omega-3 fatty acids involved in human physiology

     are ALA (found in plant oils), EPA, and DHA (both commonly found 

     in marine oils). Marine algae  and  phytoplankton  are primary sources

     of omega-3 fatty acids. Common sources of plant oils  containing the

     omega 3 ALA fatty acid include walnut , edible seeds, clary sage  seed 

     oil, algal oil , flaxseed oil , Sacha Inchi oil, Echium oil, and hemp oil ,

     while sources of animal omega-3 EPA and DHA fatty acids include

     fish oils , egg oil , squid oils, and krill oil. Supplementation with omega-

    3 fatty acids does not appear to affect the risk of death, cancer   or heart disease .[3][4]

    Omega-3 fatty acids are important for normal metabolism .[5] Mammals have a limited ability to synthesi

     omega-3 fats when the diet includes the shorter-chain omega-3 fatty acid ALA (α-linolenic acid , 18 carbons

     and 3 double bonds) to form the more important long-chain omega-3 fatty acids, EPA (eicosapentaenoic acid ,

     20 carbons and 5 double bonds) and then from EPA, the most crucial, DHA (docosahexaenoic acid  , 22

     carbons and 6 double bonds) with even greater inefficiency.[5] The ability to make the longer-chain omega-3

     fatty acids from ALA may also be impaired in aging.[6][7] In foods exposed to air, unsaturated fatty acids are

     vulnerable to oxidation  and rancidity .[8]

    Contents

    1 Health effects

    1.1 Cancer 

    1.2 Cardiovascular disease

    1.3 Inflammation

    1.4 Developmental disorders

    1.5 Mental health

    1.6 Cognitive aging

    2 Chemistry

    2.1 List of omega-3 fatty acids

    3 Mechanism of action

    3.1 Interconversion

     Article Talk Read Edit View history

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    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y_acidhttp://en.wikipedia.org/wiki/Omega-6_fatty_acidhttp://en.wikipedia.org/wiki/Omega-6_fatty_acidhttp://en.wikipedia.org/wiki/Trans_fathttp://en.wikipedia.org/wiki/Polyunsaturated_fathttp://en.wikipedia.org/wiki/Monounsaturated_fathttp://en.wikipedia.org/wiki/Unsaturated_fathttp://en.wikipedia.org/wiki/Foodhttp://en.wikipedia.org/wiki/Fat

  • 8/8/2019 Omega-3 Fatty Acid - Wikipedia, The Free Encyclopedia

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    ga-3 fatty acid - Wikipedia, the free encyclopedia

    //en.wikipedia.org/wiki/Omega-3_fatty_acid[12/15/2014 10:36:25 PM]

    4 History

    5 Dietary sources

    5.1 Daily values

    5.2 Fish

    5.3 Krill

    5.4 Calamari oil

    5.5 Plant sources

    5.6 Eggs

    5.7 Meat

    5.8 Mammalian brains and eyes

    5.9 Seal oil

    5.10 Other sources

    6 References

    7 Further reading

    8 External links

    Health effects [edit]

    Supplementation does not appear to be associated with a lower risk of all-cause mortality.[3]

    Cancer  [edit]

    The evidence linking the consumption of fish to the risk of cancer   is poor.[9] Supplementation with omeg

     fatty acids does not appear to affect this either.[4]

    A 2006 review concluded that there was no link between omega-3 fatty acids consumption and cancer.[10] Thi

     is similar to the findings of a review of studies up to February 2002 that failed to find clear effects of long and

     shorter chain omega-3 fats on total risk of death, combined cardiovascular events and cancer.[11][12] In those

     with advanced cancer and cachexia , omega-3 fatty acids supplements may be of benefit, improving appetite,

     weight, and quality of life .

    [13]

     There is tentative evidence that marine omega-3 polyunsaturated fatty acid reduce the risk of  breast cancer   but this is not conclusive.[14][15]

    The effect of consumption on  prostate cancer   is not conclusive. [15] There is a decreased risk with higher

     levels of DPA, but an increased risk of more aggressive prostate cancer with higher blood levels of combined

     EPA and DHA (found in fatty fish oil). [16]

    Cardiovascular disease [edit]

    Evidence does not support a beneficial role for omega-3 fatty acid supplementation in preventing

     cardiovascular disease  (including myocardial infarction  and sudden cardiac death ) or stroke .[3][17] Fi

     supplementation has not been shown to benefit revascularization  or arrythmia  and has no effect on heart

     failure admission rates. [18] Eating a diet high in fish that contain long chain omega-3 fatty acids does appea

     decrease the risk of stroke .[19]

    Large amounts may increase low-density lipoproteins  (LDL) (see below), up to 46%, although LDL chan

     from small to larger, buoyant, less atherogenic particles.[20]

    Omega-3 fatty acids may have a modest effect on systolic blood pressure, though studies have produced 

     inconsistent results.[21] The 18 carbon α-linolenic acid (ALA) has not been shown to have the same

     cardiovascular benefits that DHA or EPA may have.[22]

    Some evidence suggests that people with certain circulatory problems, such as varicose veins , may benefit

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     from the consumption of EPA and DHA, which may stimulate blood circulation, increase the breakdown of 

     fibrin, a compound involved in clot and scar formation, and, in addition, may reduce blood pressure.[23][24]

     Omega-3 fatty acids reduce  blood  triglyceride  levels, [25][26][27] and regular intake may reduce the risk of

     secondary and primary heart attack.[28] ALA does not confer the cardiovascular health benefits of EPA and 

     DHA.[29]

    Large amounts may increase the risk of hemorrhagic stroke in women; lower amounts are not related to this

     risk.[30]

    Inflammation [edit]

    Some research suggests that the anti-inflammatory activity of long-chain omega-3 fatty acids may translate

     into clinical effects.[31]

    For rheumatoid arthritis  (RA), one systematic review found a consistent, but modest, evidence for the effect

     marine n-3 PUFAs on symptoms such as "joint swelling and pain, duration of morning stiffness, global

     assessments of pain and disease activity" as well as the use of non-steroidal anti-inflammatory drugs.[32]

     However, the American College of Rheumatology  (ACR) has stated that there may be modest benefit fro

     use of fish oils, but that it may take months for effects to be seen, and cautions for possible gastrointestinal

     side effects and the possibility of the supplements containing mercury  or vitamin A at toxic levels. Due to th

     lack of regulations for safety and efficacy, the ACR does not recommend herbal supplements and feels there i

     an overall lack of "sound scientific evidence" for their use.[33] The  National Center for Complementary and 

     Alternative Medicine has concluded that "[n]o dietary supplement has shown clear benefits for RA", but that

     there is preliminary evidence that fish oil may be beneficial, and called for further study.[34]

    Developmental disorders [edit]

    Although not supported by current scientific evidence as a primary treatment for ADHD, autism spectrum

     disorders, and other developmental differences,[35][36] omega-3 fatty acid supplements  are being given to

     children with these conditions.[35]

    One meta-analysis concluded that omega-3 fatty acid supplementation demonstrated a modest effect for 

     improving ADHD symptoms.[37] A Cochrane review  of PUFA (not necessarily omega-3) supplementation

     found "there is little evidence that PUFA supplementation provides any benefit for the symptoms of ADHD in

     children and adolescents",[38] while a different review found "insufficient evidence to draw any conclusion

     about the use of PUFAs for children with specific learning disorders."[39] Another review concluded that the

     evidence is inconclusive for the use of omega-3 fatty acids in behavior and non-neurodegenerative

     neuropsychiatric disorders such ADHD and depression.[40]

    Fish oil has only a small benefit on the risk of early birth. [41][42]

    Mental health [edit]

    There is some evidence that omega-3 fatty acids are related to mental health ,[43] including that they may

     tentatively be useful as an add-on for the treatment of depression associated with bipolar disorder [44] and ther

     is preliminary evidence that EPA supplementation is helpful in cases of depression .[45] There is, howev

     significant difficulty in interpreting the literature due to participant recall and systematic differences in

     diets.[46]

    Cognitive aging [edit]

    Epidemiological studies suggest that consumption of omega-3 fatty acids can reduce the risk of dementia, but

     evidence of a treatment effect in dementia patients is inconclusive.[47] However, clinical evidence suggests

    http://en.wikipedia.org/wiki/Circulatory_systemhttp://en.wikipedia.org/wiki/Fibrinhttp://en.wikipedia.org/wiki/Blood_pressurehttp://en.wikipedia.org/wiki/Bloodhttp://en.wikipedia.org/wiki/Triglyceridehttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=4http://en.wikipedia.org/wiki/Rheumatoid_arthritishttp://en.wikipedia.org/wiki/American_College_of_Rheumatologyhttp://en.wikipedia.org/wiki/Mercury_(element)http://en.wikipedia.org/wiki/Vitamin_Ahttp://en.wikipedia.org/wiki/National_Center_for_Complementary_and_Alternative_Medicinehttp://en.wikipedia.org/wiki/National_Center_for_Complementary_and_Alternative_Medicinehttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=5http://en.wikipedia.org/wiki/ADHDhttp://en.wikipedia.org/wiki/Autism_spectrum_disorderhttp://en.wikipedia.org/wiki/Autism_spectrum_disorderhttp://en.wikipedia.org/wiki/Supplementshttp://en.wikipedia.org/wiki/Cochrane_reviewhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=6http://en.wikipedia.org/wiki/Mental_disorderhttp://en.wikipedia.org/wiki/Bipolar_disorderhttp://en.wikipedia.org/wiki/Ethyl_eicosapentaenoic_acidhttp://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=7http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=7http://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/wiki/Ethyl_eicosapentaenoic_acidhttp://en.wikipedia.org/wiki/Bipolar_disorderhttp://en.wikipedia.org/wiki/Mental_disorderhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=6http://en.wikipedia.org/wiki/Cochrane_reviewhttp://en.wikipedia.org/wiki/Supplementshttp://en.wikipedia.org/wiki/Autism_spectrum_disorderhttp://en.wikipedia.org/wiki/Autism_spectrum_disorderhttp://en.wikipedia.org/wiki/ADHDhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=5http://en.wikipedia.org/wiki/National_Center_for_Complementary_and_Alternative_Medicinehttp://en.wikipedia.org/wiki/National_Center_for_Complementary_and_Alternative_Medicinehttp://en.wikipedia.org/wiki/Vitamin_Ahttp://en.wikipedia.org/wiki/Mercury_(element)http://en.wikipedia.org/wiki/American_College_of_Rheumatologyhttp://en.wikipedia.org/wiki/Rheumatoid_arthritishttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=4http://en.wikipedia.org/wiki/Triglyceridehttp://en.wikipedia.org/wiki/Bloodhttp://en.wikipedia.org/wiki/Blood_pressurehttp://en.wikipedia.org/wiki/Fibrinhttp://en.wikipedia.org/wiki/Circulatory_system

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     Chemical structure of alpha-linolenic acid (ALA), an essential omega-3 fatty acid, (18:3 Δ9c,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),

     biologists 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

     physiological transformations in the human body, as it is more energy-

    stable, and other compounds can be synthesized from the other carbonyl

     end, for example in glycerides, or from double bonds in the middle of the

     chain.

     Chemical structure of eicosapentaenoic acid   (EPA).

     Chemical structure of docosahexaenoic acid   (DHA).

     benefits of treatment specifically in patients who show signs of cognitive decline but who are not sufficiently

     impaired to meet criteria for dementia.[48]

    Chemistry  [edit]

    Omega-3 fatty acids that are important in

     human physiology [citation needed] 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. As with most

     naturally-produced fatty acids, all double

     bonds are in the cis-configuration, in

     other words, the two hydrogen atoms are

     on the same side of the double bond; and 

     the double bonds are interrupted by

     methylene bridges  (-CH 2-), so that there

     are two single bonds between each pair 

     of adjacent double bonds.

    List o f omega-3 fatty acids [edit]

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

    Common name Lipid name Chemical name

    Hexadecatrienoic acid   (HTA) 16:3 ( n-3) all-cis-7,10,13-hexadecatrienoic acid 

    α-Linolenic acid  (ALA) 18:3 ( n-3) all-cis-9,12,15-octadecatrienoic acid 

    Stearidonic acid   (SDA) 18:4 ( n-3) all-cis-6,9,12,15-octadecatetraenoic acid 

    Eicosatrienoic acid   (ETE) 20:3 ( n-3) all-cis-11,14,17-eicosatrienoic acid 

    Eicosatetraenoic acid   (ETA) 20:4 ( n-3) all-cis-8,11,14,17-eicosatetraenoic acid 

    Eicosapentaenoic acid   (EPA) 20:5 ( n-3) all-cis-5,8,11,14,17-eicosapentaenoic acid 

    Heneicosapentaenoic acid   (HPA) 21:5 ( n-3) all-cis-6,9,12,15,18-heneicosapentaenoic acid 

    Docosapentaenoic acid   (DPA),

     Clupanodonic acid 22:5 ( n-3) all-cis-7,10,13,16,19-docosapentaenoic acid 

    Docosahexaenoic acid   (DHA) 22:6 ( n-3) all-cis-4,7,10,13,16,19-docosahexaenoic acid 

    Tetracosapentaenoic acid  24:5 ( n-3) all-cis-9,12,15,18,21-tetracosapentaenoic acid 

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

    http://en.wikipedia.org/wiki/Eicosapentaenoic_acidhttp://en.wikipedia.org/wiki/Docosahexaenoic_acidhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=8http://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Polyunsaturatedhttp://en.wikipedia.org/wiki/Cis-trans_isomerismhttp://en.wikipedia.org/wiki/Methylene_bridgehttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=9http://en.wikipedia.org/w/index.php?title=Hexadecatrienoic_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Alpha-linolenic_acidhttp://en.wikipedia.org/wiki/Alpha-linolenic_acidhttp://en.wikipedia.org/wiki/Stearidonic_acidhttp://en.wikipedia.org/w/index.php?title=Eicosatrienoic_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Eicosatetraenoic_acidhttp://en.wikipedia.org/wiki/Eicosapentaenoic_acidhttp://en.wikipedia.org/w/index.php?title=Heneicosapentaenoic_acid&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Heneicosapentaenoic_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Docosapentaenoic_acidhttp://en.wikipedia.org/wiki/Docosahexaenoic_acidhttp://en.wikipedia.org/w/index.php?title=Tetracosapentaenoic_acid&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Tetracosahexaenoic_acid&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Tetracosahexaenoic_acid&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Tetracosapentaenoic_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Docosahexaenoic_acidhttp://en.wikipedia.org/wiki/Docosapentaenoic_acidhttp://en.wikipedia.org/w/index.php?title=Heneicosapentaenoic_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Eicosapentaenoic_acidhttp://en.wikipedia.org/wiki/Eicosatetraenoic_acidhttp://en.wikipedia.org/w/index.php?title=Eicosatrienoic_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Stearidonic_acidhttp://en.wikipedia.org/wiki/Alpha-linolenic_acidhttp://en.wikipedia.org/wiki/Alpha-linolenic_acidhttp://en.wikipedia.org/w/index.php?title=Hexadecatrienoic_acid&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=9http://en.wikipedia.org/wiki/Methylene_bridgehttp://en.wikipedia.org/wiki/Cis-trans_isomerismhttp://en.wikipedia.org/wiki/Polyunsaturatedhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=8http://en.wikipedia.org/wiki/Docosahexaenoic_acidhttp://en.wikipedia.org/wiki/File:DHAnumbering.pnghttp://en.wikipedia.org/wiki/File:DHAnumbering.pnghttp://en.wikipedia.org/wiki/File:DHAnumbering.pnghttp://en.wikipedia.org/wiki/Eicosapentaenoic_acidhttp://en.wikipedia.org/wiki/File:EPAnumbering.pnghttp://en.wikipedia.org/wiki/File:EPAnumbering.pnghttp://en.wikipedia.org/wiki/File:EPAnumbering.pnghttp://en.wikipedia.org/wiki/File:ALAnumbering.svghttp://en.wikipedia.org/wiki/File:ALAnumbering.svghttp://en.wikipedia.org/wiki/File:ALAnumbering.svg

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    Mechanism of action [edit]

    The 'essential' fatty acids were given their name when researchers found that they are essential to normal

     growth in young children and animals, though the modern definition of 'essential ' is more strict. A small

     amount of omega-3 in the diet (~1% of total calories) enabled normal growth, and increasing the amount had 

     little to no additional effect on growth.[49]

    Likewise, researchers found that omega-6 fatty acids (such as γ-linolenic acid  and arachidonic acid  ) p

     similar role in normal growth. However, they also found that omega-6 was "better" at supporting dermal

     integrity, renal  function, and  parturition . These preliminary findings led researchers to concentrate their 

     studies on omega-6, and it is only in recent decades that omega-3 has become of interest.[49]

    In 1964, it was discovered that enzymes found in sheep tissues convert omega-6 arachidonic acid into the

     inflammatory  agent called prostaglandin  E,2,[50] which both causes the sensation of pain and expedites

     healing and immune response in traumatized and infected tissues.[49] By 1979, more of what are now known

     as eicosanoids  were discovered: thromboxanes , prostacyclins , and the leukotrienes .[49] The eicosanoid

     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.[49] Researchers found that certain

     omega-3 fatty acids are also converted into eicosanoids, but at a much slower rate. Eicosanoids made from

     omega-3 fatty acids are often referred to as anti-inflammatory, but in fact they are just less inflammatory than

     those made from omega-6 fats. If both omega-3 and omega-6 fatty acids are present, they will "compete" to b

     transformed,[49] so the ratio of long-chain omega-3:omega-6 fatty acids directly affects the type of eicosanoid

     that are produced.[49]

    This competition was recognized as important when it was found that thromboxane is a factor in the clumping

     of platelets , which can both cause death by thrombosis  and prevent death by bleeding. Likewise, the

     leukotrienes were found to be important in immune/inflammatory-system response, and therefore relevant to

     arthritis , lupus , asthma , and recovery from infections. These discoveries led to greater interest in finding

     ways to control the synthesis of omega-6 eicosanoids. The simplest way would be by consuming more omega

    3 and fewer omega-6 fatty acids.[49]

    They are required during the prenatal period for the formation of synapses  and cell membranes. These

     processes are also essential in postnatal human development for injury response of the central nervous system

     and retinal stimulation. [51]

    Interconversion [edit]

    Conversion efficiency of ALA to EPA and DHA [edit]

    Humans can convert short-chain omega-3 fatty acids to long-chain forms (EPA, DHA) with an efficiency below 5%.[52][53] The omega-3 conversion efficiency is greater in women than in men, but less-studied.[54]

    These conversions occur competitively with omega-6 fatty acids, which are essential closely related chemical

     analogues that are derived from linoleic acid. Both the omega-3 α-linolenic acid and omega-6 linoleic acid 

     must be obtained from food. Synthesis of the longer omega-3 fatty acids from linolenic acid within the body i

     competitively slowed by the omega-6 analogues. Thus, accumulation of long-chain omega-3 fatty acids in

     tissues is more effective when they are obtained directly from food or when competing amounts of omega-6

     analogues do not greatly exceed the amounts of omega-3.[citation needed]

    The conversion of ALA to EPA and further to DHA in humans has been reported to be limited, but varies with

    http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=10http://en.wikipedia.org/wiki/Essential_fatty_acidhttp://en.wikipedia.org/wiki/Essential_fatty_acidhttp://en.wikipedia.org/wiki/Gamma-linolenic_acidhttp://en.wikipedia.org/wiki/Gamma-linolenic_acidhttp://en.wikipedia.org/wiki/Arachidonic_acidhttp://en.wikipedia.org/wiki/Dermishttp://en.wikipedia.org/wiki/Renalhttp://en.wikipedia.org/wiki/Parturitionhttp://en.wikipedia.org/wiki/Inflammationhttp://en.wikipedia.org/wiki/Prostaglandinhttp://en.wikipedia.org/wiki/Eicosanoidhttp://en.wikipedia.org/wiki/Thromboxanehttp://en.wikipedia.org/wiki/Prostacyclinhttp://en.wikipedia.org/wiki/Leukotrienehttp://en.wikipedia.org/wiki/Platelethttp://en.wikipedia.org/wiki/Thrombosishttp://en.wikipedia.org/wiki/Arthritishttp://en.wikipedia.org/wiki/Lupus_erythematosushttp://en.wikipedia.org/wiki/Asthmahttp://en.wikipedia.org/wiki/Synapseshttp://en.wikipedia.org/wiki/Central_nervous_systemhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=11http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=12http://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=12http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=11http://en.wikipedia.org/wiki/Central_nervous_systemhttp://en.wikipedia.org/wiki/Synapseshttp://en.wikipedia.org/wiki/Asthmahttp://en.wikipedia.org/wiki/Lupus_erythematosushttp://en.wikipedia.org/wiki/Arthritishttp://en.wikipedia.org/wiki/Thrombosishttp://en.wikipedia.org/wiki/Platelethttp://en.wikipedia.org/wiki/Leukotrienehttp://en.wikipedia.org/wiki/Prostacyclinhttp://en.wikipedia.org/wiki/Thromboxanehttp://en.wikipedia.org/wiki/Eicosanoidhttp://en.wikipedia.org/wiki/Prostaglandinhttp://en.wikipedia.org/wiki/Inflammationhttp://en.wikipedia.org/wiki/Parturitionhttp://en.wikipedia.org/wiki/Renalhttp://en.wikipedia.org/wiki/Dermishttp://en.wikipedia.org/wiki/Arachidonic_acidhttp://en.wikipedia.org/wiki/Gamma-linolenic_acidhttp://en.wikipedia.org/wiki/Gamma-linolenic_acidhttp://en.wikipedia.org/wiki/Essential_fatty_acidhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=10

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     individuals.[55][56] Women have higher ALA conversion efficiency than men, which is

     presumed [citation needed] to be due to the lower rate of use 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 omega-3 and omega-6 fatty acids, that controls the

     conversion efficiency.[57]

    The omega-6 to omega-3 ratio [edit]

    Main article: Essential fatty acid interactions

    Some older clinical studies [49][58] indicate that the ingested ratio of omega-6 to omega-3 (especially linoleic

     alpha-linolenic) fatty acids is important to maintaining cardiovascular health. However, three studies

     published in 2005, 2007 and 2008, including a randomized controlled trial , found that, while omega-3

     polyunsaturated fatty acids are extremely beneficial in preventing heart disease in humans, the levels of 

     omega-6 polyunsaturated fatty acids (and, therefore, the ratios) did not matter. [59][60][61]

    Both omega-6 and omega-3 fatty acids are essential; i.e., humans must consume them in their diet. Omega-6

     and omega-3 eighteen-carbon polyunsaturated fatty acids compete for the same metabolic enzymes, thus the

     omega-6:omega-3 ratio of ingested fatty acids has significant influence on the ratio and rate of production of 

     eicosanoids, a group of hormones intimately involved in the body's inflammatory and homeostatic processes,

     which include the prostaglandins , leukotrienes , and thromboxanes , among others. Altering this ratio can change the body's metabolic and inflammatory state.[11] In general, grass-fed animals accumulate more

     omega-3 than do grain-fed animals, which accumulate relatively more omega-6.[62] Metabolites  of omega-6

     are more inflammatory (esp. arachidonic acid) than those of omega-3. This necessitates that omega-6 and 

     omega-3 be consumed in a balanced proportion; healthy ratios of omega-6:omega-3, according to some

     authors, range from 1:1 to 1:4 (an individual needs more omega-3 than omega-6).[63] Other authors believe

     that ratio 4:1 (when the amount of omega-6 is only 4 times greater than that of omega-3) is already

     healthy.[64][65] Studies suggest the evolutionary human diet, rich in game animals, seafood, and other sources

     of omega-3, may have provided such a ratio.[66][67]

    Typical Western diets provide ratios of between 10:1 and 30:1 (i.e., dramatically higher levels of omega-6 than

     omega-3).[68] The ratios of omega-6 to omega-3 fatty acids in some common vegetable oils are: canola  2:1,

     hemp  2-3:1, [69] soybean  7:1, olive 3–13:1, sunflower  (no omega-3), flax 1:3, [70] cottonseed   (almost n

     omega-3), peanut  (no omega-3), grapeseed oil  (almost no omega-3) and corn oil  46:1 ratio of omega-6 to

     omega-3.[71]

    History  [edit]

    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 since the 1980s.[72][73]

    On September 8, 2004, the U.S. Food and Drug Administration gave "qualified health claim" status to EPA

     and DHA omega-3 fatty acids, stating, "supportive but not conclusive research shows that consumption of 

     EPA and DHA [omega-3] fatty acids may reduce the risk of coronary heart disease."[74] This updated and 

     modified their health risk advice letter of 2001 (see below). As of this writing, regulatory agencies[who?] do

     not accept that there is sufficient evidence for any of the 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."[75]

    http://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=13http://en.wikipedia.org/wiki/Essential_fatty_acid_interactionshttp://en.wikipedia.org/wiki/Randomized_controlled_trialhttp://en.wikipedia.org/wiki/Prostaglandinshttp://en.wikipedia.org/wiki/Leukotrieneshttp://en.wikipedia.org/wiki/Thromboxaneshttp://en.wikipedia.org/wiki/Metaboliteshttp://en.wikipedia.org/wiki/Canolahttp://en.wikipedia.org/wiki/Hemp_oilhttp://en.wikipedia.org/wiki/Soybeanhttp://en.wikipedia.org/wiki/Olivehttp://en.wikipedia.org/wiki/Sunflowerhttp://en.wikipedia.org/wiki/Flaxhttp://en.wikipedia.org/wiki/Cottonseedhttp://en.wikipedia.org/wiki/Peanuthttp://en.wikipedia.org/wiki/Grapeseed_oilhttp://en.wikipedia.org/wiki/Corn_oilhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=14http://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Words_to_watch#Unsupported_attributionshttp://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Words_to_watch#Unsupported_attributionshttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=14http://en.wikipedia.org/wiki/Corn_oilhttp://en.wikipedia.org/wiki/Grapeseed_oilhttp://en.wikipedia.org/wiki/Peanuthttp://en.wikipedia.org/wiki/Cottonseedhttp://en.wikipedia.org/wiki/Flaxhttp://en.wikipedia.org/wiki/Sunflowerhttp://en.wikipedia.org/wiki/Olivehttp://en.wikipedia.org/wiki/Soybeanhttp://en.wikipedia.org/wiki/Hemp_oilhttp://en.wikipedia.org/wiki/Canolahttp://en.wikipedia.org/wiki/Metaboliteshttp://en.wikipedia.org/wiki/Thromboxaneshttp://en.wikipedia.org/wiki/Leukotrieneshttp://en.wikipedia.org/wiki/Prostaglandinshttp://en.wikipedia.org/wiki/Randomized_controlled_trialhttp://en.wikipedia.org/wiki/Essential_fatty_acid_interactionshttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=13http://en.wikipedia.org/wiki/Wikipedia:Citation_needed

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    Grams of omega-3 per 3oz (85g) serving [76]

     [77]

    Common namegrams omega-

    3

    Flax 11.4 [78]

    Hemp 11.0

    Herring, sardines 1.3–2

    Mackerel:

     Spanish /Atlantic/Pacific1.1–1.7

    Salmon 1.1–1.9

    Halibut 0.60–1.12

    Tuna 0.21–1.1

    Swordfish 0.97

    Greenshell/lipped mussels 0.95 [78]

    Tilefish 0.9

    Tuna (canned, light) 0.17–0.24

    Pollock  0.45

    Cod  0.15–0.24

    Catfish 0.22–0.3

    Flounder  0.48

    Grouper  0.23

    Mahi mahi 0.13

    Orange roughy 0.028

    Red snapper  0.29

    Shark  0.83

    King mackerel 0.36

    Hoki (blue grenadier) 0.41 [78]

    Gemfish 0.40 [78]

    Blue eye cod  0.31 [78]

    Sydney rock oysters 0.30 [78]

    Tuna, canned  0.23 [78]

    Snapper  0.22 [78]

    Eggs, large regular  0.109 [78]

    Strawberry  or Kiwifruit 0.10-0.20

    Broccoli 0.10-0.20

    Barramundi, saltwater  0.100 [78]

    Giant tiger prawn 0.100 [78]

    Dietary sources [edit]

    Daily values [edit]

    In the United States, the Institute of Medicine publishe

     a system of Dietary Reference Intakes, which includes

     Recommended Dietary Allowances (RDAs) for 

     individual nutrients, and Acceptable Macronutrient

     Distribution Ranges (AMDRs) for certain groups of  nutrients, such as fats. When there is insufficient

     evidence to determine an RDA, the institute may

     publish an Adequate Intake  (AI) instead, which has a

     similar meaning, but is less certain. The AI for α-

    linolenic acid  is 1.6 grams/day for men and 

     1.1 grams/day for women, while the AMDR is 0.6% to

     1.2% of total energy.[79]

    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

     disease. Because the physiological potency of EPA an

     DHA is much greater than that of ALA, it is not

     possible to estimate one AMDR for all omega-3 fatty

     acids. Approximately 10 percent of the AMDR can be

     consumed as EPA and/or DHA."[79] There was

     insufficient evidence as of 2005 to set an upper 

     tolerable limit for omega-3 fatty acids.[79]

    Heavy metal poisoning  by the body's accumulation o traces of heavy metals, in particular mercury , lead ,

     nickel, arsenic , and cadmium , is a possible risk from

     consuming fish oil supplements.[medical citation needed]

     Also, other contaminants ( PCBs , furans , dioxins ,

     PBDEs) might be found, especially in less-refined fish

     oil supplements.[citation needed] However, heavy metal

     toxicity from consuming fish oil supplements is highly

     unlikely, because heavy metals selectively bind with

     protein in the fish flesh rather than accumulate in the

     oil. An independent test in 2005 of 44 fish oils on the

     US market found all of the products passed safety

     standards for potential

     contaminants.[80][unreliable source?]

    The FDA has advised that adults can safely consume a

     total of 3 grams per day of combined DHA and EPA,

     with no more than 2 g per day coming from dietary

     supplements.[81]

    Throughout their history, the Council for Responsible

    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edia.org/wiki/Salmonhttp://en.wikipedia.org/wiki/Pacific_mackerelhttp://en.wikipedia.org/wiki/Atlantic_mackerelhttp://en.wikipedia.org/wiki/Spanish_mackerelhttp://en.wikipedia.org/wiki/Hemphttp://en.wikipedia.org/wiki/Flax

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    Lean red meat 0.031 [78]

    Turkey 0.030 [78]

    Cereals, rice, pasta, etc. 0.00 [78]

    Fruit 0.00 [78]

    Milk, regular  0.00 [78]

    Bread, regular  0.00 [78]

    Vegetables 0.00 [78]

     Nutrition and the World Health Organization  have

     published acceptable standards regarding contaminant

     in fish oil. The most stringent current standard is the

     International Fish Oils

     Standard.[82][non-primary source needed] Fish oils that ar

     molecularly distilled  under vacuum typically make thi

     highest-grade, and have measurable levels of 

     contaminants (measured parts per billion and parts per

     trillion).[citation needed]

    A recent trend has been to fortify food with omega-3 fatty acid supplements. Global food companies have

     launched omega-3 fatty acid fortified bread, mayonnaise, pizza, yogurt, orange juice, children's pasta, milk,

     eggs, popcorn, confections, and infant formula.[citation needed]

    The American Heart Association  has set up dietary recommendations for EPA and DHA due to their 

     cardiovascular benefits: Individuals with no history of coronary heart disease or myocardial infarction should

     consume oily fish or fish oils two times per week; those having been diagnosed with coronary heart disease

     after infarction should consume 1 g EPA and DHA per day from oily fish or supplements; those wishing to

     lower blood triglycerides should consume 2–4 g of EPA and DHA per day in the form of 

     supplements.[83][dated info]

    Fish [edit]

    The most widely available dietary 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

     omega-3 as omega-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 are known to accumulate up the food chain . After extensive review, researchers from

     Harvard's School of Public Health  in the Journal of the American Medical Association (2006) reported

     that the benefits of fish intake generally far outweigh the potential risks. Although fish are a dietary source of

     omega-3 fatty acids, fish do not synthesize them; they obtain them from the algae  (microalgae  in particular)

     or plankton  in their diets. [84]

    Fish oil [edit]

    See also: Fish oil

    Marine and freshwater fish oil vary in content of arachidonic acid, EPA and DHA.[85] They also differ in their

     effects on organ lipids.[85] Not all forms of fish oil may be equally digestible. Of four studies that compare

     bioavailability of the glyceryl ester form of fish oil vs. the ethyl ester  form, two have concluded the natural

     glyceryl ester form is better, and the other two studies did not find a significant difference. No studies have

     shown the ethyl ester form to be superior, although it is cheaper to manufacture.[86][87]

    Krill [edit]

    Krill oilis a newly [when?] discovered source of omega-3 fatty acids. Various claims are made in support of 

     krill oil as a superior [citation needed] source of omega-3 fatty acids. The effect of krill oil, at a lower dose of 

     EPA + DHA (62.8%), was demonstrated to be similar to that of fish oil.[88]

    Calamari oil [edit]

    Calamari oil (also known as Squid oil) is another source of omega-3 fatty acid.[89] Calamari is considered to b

    http://en.wikipedia.org/wiki/Red_meathttp://en.wikipedia.org/wiki/Turkeyhttp://en.wikipedia.org/wiki/Cerealhttp://en.wikipedia.org/wiki/Fruithttp://en.wikipedia.org/wiki/Milkhttp://en.wikipedia.org/wiki/Breadhttp://en.wikipedia.org/wiki/Vegetablehttp://en.wikipedia.org/wiki/World_Health_Organizationhttp://en.wikipedia.org/wiki/Wikipedia:No_original_research#Primary.2C_secondary_and_tertiary_sourceshttp://en.wikipedia.org/wiki/Molecular_distillationhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/American_Heart_Associationhttp://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Precise_languagehttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=17http://en.wikipedia.org/wiki/Oily_fishhttp://en.wikipedia.org/wiki/Salmonhttp://en.wikipedia.org/wiki/Herringhttp://en.wikipedia.org/wiki/Mackerelhttp://en.wikipedia.org/wiki/Anchovieshttp://en.wikipedia.org/wiki/Sardinehttp://en.wikipedia.org/wiki/Tunahttp://en.wikipedia.org/wiki/Heavy_metalshttp://en.wikipedia.org/wiki/Polychlorinated_biphenylhttp://en.wikipedia.org/wiki/Biomagnificationhttp://en.wikipedia.org/wiki/Harvard_School_of_Public_Healthhttp://en.wikipedia.org/wiki/Algaehttp://en.wikipedia.org/wiki/Microalgaehttp://en.wikipedia.org/wiki/Planktonhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=18http://en.wikipedia.org/wiki/Fish_oilhttp://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=19http://en.wikipedia.org/wiki/Krill_oilhttp://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_itemshttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=20http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=20http://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_itemshttp://en.wikipedia.org/wiki/Krill_oilhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=19http://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/wiki/Fish_oilhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=18http://en.wikipedia.org/wiki/Planktonhttp://en.wikipedia.org/wiki/Microalgaehttp://en.wikipedia.org/wiki/Algaehttp://en.wikipedia.org/wiki/Harvard_School_of_Public_Healthhttp://en.wikipedia.org/wiki/Biomagnificationhttp://en.wikipedia.org/wiki/Polychlorinated_biphenylhttp://en.wikipedia.org/wiki/Heavy_metalshttp://en.wikipedia.org/wiki/Tunahttp://en.wikipedia.org/wiki/Sardinehttp://en.wikipedia.org/wiki/Anchovieshttp://en.wikipedia.org/wiki/Mackerelhttp://en.wikipedia.org/wiki/Herringhttp://en.wikipedia.org/wiki/Salmonhttp://en.wikipedia.org/wiki/Oily_fishhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=17http://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Precise_languagehttp://en.wikipedia.org/wiki/American_Heart_Associationhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Molecular_distillationhttp://en.wikipedia.org/wiki/Wikipedia:No_original_research#Primary.2C_secondary_and_tertiary_sourceshttp://en.wikipedia.org/wiki/World_Health_Organizationhttp://en.wikipedia.org/wiki/Vegetablehttp://en.wikipedia.org/wiki/Breadhttp://en.wikipedia.org/wiki/Milkhttp://en.wikipedia.org/wiki/Fruithttp://en.wikipedia.org/wiki/Cerealhttp://en.wikipedia.org/wiki/Turkeyhttp://en.wikipedia.org/wiki/Red_meat

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    Chia is grown commercially for its seeds

     rich in ALA.

    Flax seeds produce linseed oil which has

     high ALA content

     more environmentally friendly than fish or krill oil, due to it being prepared from the largely unused portions

     of calamari catches.[90]

    Plant sources [edit]

    These tables are incomplete.

    Table 1. ALA content as the percentage of the seed oil.[91]

    Common

     name

     Al ternat ive

     name

    Linnaean

     name % ALA

    Kiwifruit

     seed oil

    Chinese

     gooseberry

     Actinidia

     deliciosa63 [92]

    Perilla shisoPerilla

     frutescens61

    Chia seed chia sageSalvia

     hispanica58

    Flax linseed Linum

     usitatissimum

    53 [93] – 

     59[94]

    Lingonberry CowberryVaccinium

     vitis-idaea49

    CamelinaGold-of-

     pleasure

    Camelina

     sativa36

    Purslane PortulacaPortulaca

     oleracea35

    Black 

     raspberry

    Rubus

     occidentalis33

    Hemp Cannabis

     sativa19

    Canola 9 [93] – 11

    Table 2. ALA content as the percentage of the whole

     food.[93][95]

    Common name Linnaean name % ALA

    Flaxseed  Linum usitatissimum 18.1

    Hempseed  Cannabis sativa 8.7

    Butternuts Juglans cinerea 8.7

    Persian walnuts Juglans regia 6.3

    Pecan nuts Carya illinoinensis 0.6

    Hazel nuts Corylus avellana 0.1

    Flaxseed (or linseed) ( Linum usitatissimum) and its oil are perhaps the most widely available botanical

     source of the omega-3 fatty acid ALA. Flaxseed oil  consists of approximately 55% ALA, which makes it six

     times richer than most fish oils in omega-3 fatty acids.[96] A portion of this is converted by the body to EPA

    [97]

    http://en.wikipedia.org/wiki/Salvia_hispanicahttp://en.wikipedia.org/wiki/Flaxhttp://en.wikipedia.org/wiki/Linseed_oilhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=21http://en.wikipedia.org/wiki/Alpha-linolenic_acidhttp://en.wikipedia.org/wiki/Linnaean_namehttp://en.wikipedia.org/wiki/Linnaean_namehttp://en.wikipedia.org/w/index.php?title=Kiwifruit_seed_oil&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Kiwifruit_seed_oil&action=edit&redlink=1http://en.wikipedia.org/wiki/Actinidia_deliciosahttp://en.wikipedia.org/wiki/Actinidia_deliciosahttp://en.wikipedia.org/wiki/Perillahttp://en.wikipedia.org/wiki/Perilla_frutescenshttp://en.wikipedia.org/wiki/Perilla_frutescenshttp://en.wikipedia.org/wiki/Salvia_hispanicahttp://en.wikipedia.org/wiki/Salvia_hispanicahttp://en.wikipedia.org/wiki/Flaxhttp://en.wikipedia.org/wiki/Vaccinium_vitis-idaeahttp://en.wikipedia.org/wiki/Vaccinium_vitis-idaeahttp://en.wikipedia.org/wiki/Camelina_sativahttp://en.wikipedia.org/wiki/Camelina_sativahttp://en.wikipedia.org/wiki/Portulacahttp://en.wikipedia.org/wiki/Rubus_occidentalishttp://en.wikipedia.org/wiki/Rubus_occidentalishttp://en.wikipedia.org/wiki/Hemphttp://en.wikipedia.org/wiki/Cannabis_sativahttp://en.wikipedia.org/wiki/Cannabis_sativahttp://en.wikipedia.org/wiki/Linnaean_namehttp://en.wikipedia.org/wiki/Linum_usitatissimumhttp://en.wikipedia.org/wiki/Cannabis_sativahttp://en.wikipedia.org/wiki/Juglans_cinereahttp://en.wikipedia.org/wiki/Juglans_regiahttp://en.wikipedia.org/wiki/Carya_illinoinensishttp://en.wikipedia.org/wiki/Corylus_avellanahttp://en.wikipedia.org/wiki/Botanicalhttp://en.wikipedia.org/wiki/Linseed_oilhttp://en.wikipedia.org/wiki/Linseed_oilhttp://en.wikipedia.org/wiki/Botanicalhttp://en.wikipedia.org/wiki/Corylus_avellanahttp://en.wikipedia.org/wiki/Carya_illinoinensishttp://en.wikipedia.org/wiki/Juglans_regiahttp://en.wikipedia.org/wiki/Juglans_cinereahttp://en.wikipedia.org/wiki/Cannabis_sativahttp://en.wikipedia.org/wiki/Linum_usitatissimumhttp://en.wikipedia.org/wiki/Linnaean_namehttp://en.wikipedia.org/wiki/Cannabis_sativahttp://en.wikipedia.org/wiki/Cannabis_sativahttp://en.wikipedia.org/wiki/Hemphttp://en.wikipedia.org/wiki/Rubus_occidentalishttp://en.wikipedia.org/wiki/Rubus_occidentalishttp://en.wikipedia.org/wiki/Portulacahttp://en.wikipedia.org/wiki/Camelina_sativahttp://en.wikipedia.org/wiki/Camelina_sativahttp://en.wikipedia.org/wiki/Vaccinium_vitis-idaeahttp://en.wikipedia.org/wiki/Vaccinium_vitis-idaeahttp://en.wikipedia.org/wiki/Flaxhttp://en.wikipedia.org/wiki/Salvia_hispanicahttp://en.wikipedia.org/wiki/Salvia_hispanicahttp://en.wikipedia.org/wiki/Perilla_frutescenshttp://en.wikipedia.org/wiki/Perilla_frutescenshttp://en.wikipedia.org/wiki/Perillahttp://en.wikipedia.org/wiki/Actinidia_deliciosahttp://en.wikipedia.org/wiki/Actinidia_deliciosahttp://en.wikipedia.org/w/index.php?title=Kiwifruit_seed_oil&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Kiwifruit_seed_oil&action=edit&redlink=1http://en.wikipedia.org/wiki/Linnaean_namehttp://en.wikipedia.org/wiki/Linnaean_namehttp://en.wikipedia.org/wiki/Alpha-linolenic_acidhttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=21http://en.wikipedia.org/wiki/Linseed_oilhttp://en.wikipedia.org/wiki/Flaxhttp://en.wikipedia.org/wiki/File:Flax_seeds.jpghttp://en.wikipedia.org/wiki/File:Flax_seeds.jpghttp://en.wikipedia.org/wiki/File:Flax_seeds.jpghttp://en.wikipedia.org/wiki/Salvia_hispanicahttp://en.wikipedia.org/wiki/File:Semillas_de_Ch%C3%ADa.jpghttp://en.wikipedia.org/wiki/File:Semillas_de_Ch%C3%ADa.jpghttp://en.wikipedia.org/wiki/File:Semillas_de_Ch%C3%ADa.jpg

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     and DHA, though the actual converted percentage may differ between men and women.

    100 g of the leaves of Purslane  contains 300–400 mg ALA. [98]

    In 2013 Rothamsted Research  in the UK reported they had developed a genetically modified form of the p

     Camelina  that produced EPA and DHA. Oil from the seeds of this plant contained on average 11% EPA and 

     8% DHA in one development and 24% EPA in another.[99][100]

    Eggs [edit]

    Eggs produced by hens fed a diet of greens and insects contain higher levels of omega-3 fatty acids than those

     produced by chickens fed corn or soybeans.[101] In addition to feeding chickens insects and greens, fish oils

     may be added to their diets to increase the omega-3 fatty acid concentrations in eggs.[102]

    The addition of flax and canola seeds to the diets of chickens, both good sources of alpha-linolenic acid,

     increases the omega-3 content of the eggs, predominantly DHA.[103]

    The addition of green algae or seaweed to the diets boosts the content of DHA and EPA content, which are the

     forms of omega-3 approved by the FDA for medical claims. A common consumer complaint is "Omega-3

     eggs can sometimes have a fishy taste if the hens are fed marine oils."[104]

    Meat [edit]Omega 3 fatty acids are formed in the chloroplasts of green leaves and algae. While seaweeds and algae are th

     source of omega 3 fatty acids present in fish, grass is the source of omega 3 fatty acids present in grass fed 

     animals.[105] When cattle are taken off omega 3 fatty acid rich grass and shipped to a feedlot to be fattened on

     omega 3 fatty acid deficient grain, they begin losing their store of this beneficial fat. Each day that an animal

     spends in the feedlot, the amount of omega 3 fatty acids in its meat is diminished.[106]

    The omega-6-to-omega-3 ratio of grass-fed   beef is about 2:1, making it a more useful source of omega-3

     grain-fed beef, which usually has a ratio of 4:1.[62]

    In a 2009 joint study by the USDA and researchers at Clemson University in South Carolina, grass-fed beef 

     was compared with grain-finished beef. The researchers found that grass-finished beef is higher in moisture content, 42.5% lower total lipid content, 54% lower in total fatty acids, 54% higher in beta-carotene, 288%

     higher in vitamin E (alpha-tocopherol), higher in the B-vitamins thiamin and riboflavin, higher in the mineral

     calcium, magnesium, and potassium, 193% higher in total omega-3s, 117% higher in CLA (cis-9 trans-11,

     which is a potential cancer fighter), 90% higher in vaccenic acid (which can be transformed into CLA), lower

     in the saturated fats linked with heart disease, and has a healthier ratio of omega-6 to omega-3 fatty acids

     (1.65 vs 4.84). Protein and cholesterol content were equal.[62]

    In most countries, commercially available lamb is typically grass-fed, and thus higher in omega-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 omega-3.[107]

    The omega-3 content of chicken  meat may be enhanced by increasing the animals' dietary intake of grains

     high in omega-3, such as flax, chia, and canola.[108]

    Kangaroo meat  is also a source of omega-3, with fillet and steak containing 74 mg per 100 g of raw meat.[10

    Mammalian brains and eyes [edit]

    The  brains  and eyes of mammals are extremely rich in DHA as well as other omega-3 fatty acids.[110] DHA i

     a major structural component of the mammalian brain, and is in fact the most abundant omega-3 fatty acid in

     the brain.[111]

    http://en.wikipedia.org/wiki/Portulaca_oleraceahttp://en.wikipedia.org/wiki/Rothamsted_Researchhttp://en.wikipedia.org/wiki/Camelinahttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=22http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=23http://en.wikipedia.org/wiki/Cattle_feedinghttp://en.wikipedia.org/wiki/Chickenhttp://en.wikipedia.org/wiki/Kangaroo_meathttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=24http://en.wikipedia.org/wiki/Brain_(food)http://en.wikipedia.org/wiki/Brain_(food)http://en.wikipedia.org/wiki/Brain_(food)http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=24http://en.wikipedia.org/wiki/Kangaroo_meathttp://en.wikipedia.org/wiki/Chickenhttp://en.wikipedia.org/wiki/Cattle_feedinghttp://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=23http://en.wikipedia.org/w/index.php?title=Omega-3_fatty_acid&action=edit&section=22http://en.wikipedia.org/wiki/Camelinahttp://en.wikipedia.org/wiki/Rothamsted_Researchhttp://en.wikipedia.org/wiki/Portulaca_oleracea

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    Seal oi l [edit]

    Seal oil is a source of EPA, DPA, and DHA. According to Health Canada, it helps to support the developm

     of the brain, eyes, and nerves in children up to 12 years of age.[112] However, like all seal products , it is not

     allowed for import into the European Union.[113]

    Other sources [edit]

    The microalgae Crypthecodinium cohnii and Schizochytrium are rich sources of DHA but not EPA, and

     be produced commercially in bioreactors .[citation needed]

    Oil from brown algae  (kelp) is a source of EPA. [114] The alga, Nannochloropsis, has high levels of EPA.

    In 2006 the Journal of Dairy Science published a study entitled, "The Linear Relationship between the

     Proportion of Fresh Grass in the Cow Diet, Milk Fatty Acid Composition, and Butter Properties". The study

     found that butter made from the milk of grass-fed cows contains substantially more CLA, vitamin E, beta-

    carotene, and omega-3 fatty acids than butter made from the milk of cows that have limited access to

     pasture.[116]

    References [edit]

    1. ^  "Related terms" . Omega-3 fatty acids, fish oil, alpha-linolenic acid. Mayo Clinic . Retrieved June 20

     2012 .

    2. ^  Scorletti E, Byrne CD (2013). "Omega-3 fatty acids, hepatic lipid metabolism, and nonalcoholic fatty liver 

     disease". Annual review of nutrition 33: 231–48. doi:10.1146/annurev-nutr-071812-161230 .

     PMID 23862644 .

    3. ^ a b c Rizos EC, Ntzani EE, Bika E, Kostapanos MS, Elisaf MS (September 2012). "Association Between

     Omega-3 Fatty Acid Supplementation and Risk of Major Cardiovascular Disease Events A Systematic Review

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    4. ^ a b MacLean CH, Newberry SJ, Mojica WA, Khanna P, Issa AM, Suttorp MJ, Lim YW, Traina SB, Hilton L

     Garland R, Morton SC (2006-01-25). "Effects of omega-3 fatty acids on cancer risk: a systematic review.".

     JAMA: the Journal of the American Medical Association 295 (4): 403–15.

     doi:10.1001/jama.295.4.403 . PMID 16434631 .

    5. ^ a b "Omega-3 Fatty Acids and Health: Fact Sheet for Health Professionals" . US National Institutes of 

     Health, Office of Dietary Supplements. 2005. Retrieved 12 April 2014 .

    6. ^  Freemantle E, Vandal M, Tremblay-Mercier J, Tremblay S, Blachère JC, Bégin ME, Brenna JT, Windust A,

     Cunnane SC (2006). "Omega-3 fatty acids, energy substrates, and brain function during aging".

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     doi:10.1016/j.plefa.2006.05.011 .

    7. ^  Gao F, Taha AY, Ma K, Chang L, Kiesewetter D, Rapoport SI (2012). "Aging decreases rate of 

     docosahexaenoic acid synthesis-secretion from circulating unesterified α-linolenic acid by rat liver". AGE 35

     (3): 597–608. doi:10.1007/s11357-012-9390-1 . PMID 22388930 .

    8. ^  Chaiyasit W, Elias RJ, McClements DJ, Decker EA (2007). "Role of Physical Structures in Bulk Oils on

     Lipid Oxidation". Critical Reviews in Food Science and Nutrition 47 (3): 299–317.

     doi:10.1080/10408390600754248 . PMID 17453926 .

    9. ^  Sala-Vila A, Calder PC (October–November 2011). "Update on the relationship of fish intake with prostate,

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    10. ^  MacLean CH, Newberry SJ, Mojica WA, Khanna P, Issa AM, Suttorp MJ, Lim YW, Traina SB, Hilton L,

     Garland R, Morton SC (2006). "Effects of n-3 Fatty Acids on Cancer Risk" . JAMA 295 (4): 403–415.

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