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Wikipedia

Omega-3 fatty acid

August 22, 2023

See also: Omega-3 acid ethyl esters

Omega−3 fatty acids, also called Omega−3 oils, ω−3 fatty acids or n−3 fatty acids,[1] are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond, three atoms away from the terminal methyl group in their chemical structure.[2] They are widely distributed in nature, being important constituents of animal lipid metabolism, and they play an important role in the human diet and in human physiology.[2][3] The three types of omega−3 fatty acids involved in human physiology are α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). ALA can be found in plants, while DHA and EPA are found in algae and fish. Marine algae and phytoplankton are primary sources of omega−3 fatty acids.[4] DHA and EPA accumulate in fish that eat these algae.[5] Common sources of plant oils containing ALA include walnuts, edible seeds, and flaxseeds as well as hempseed oil, while sources of EPA and DHA include fish and fish oils,[1] and algae oil.

Mammals are unable to synthesize the essential omega−3 fatty acid ALA and can only obtain it through diet. However, they can use ALA, when available, to form EPA and DHA, by creating additional double bonds along its carbon chain (desaturation) and extending it (elongation). Namely, ALA (18 carbons and 3 double bonds) is used to make EPA (20 carbons and 5 double bonds), which is then used to make DHA (22 carbons and 6 double bonds).[1][2] The ability to make the longer-chain omega−3 fatty acids from ALA may be impaired in aging.[6] In foods exposed to air, unsaturated fatty acids are vulnerable to oxidation and rancidity.[2][7]

There is no high-quality evidence that dietary supplementation with omega−3 fatty acids reduces the risk of cancer or cardiovascular disease.[8][9][10] Furthermore, fish oil supplement studies have failed to support claims of preventing heart attacks or strokes or any vascular disease outcomes.[11][12][13]

History

In 1929, George and Mildred Burr discovered that fatty acids were critical to health. If fatty acids were absent from the diet, a life-threatening deficiency syndrome ensued. The Burrs coined the phrase "essential fatty acids".[14] Since then, researchers have shown a growing interest in unsaturated essential fatty acids as they form the framework for the organism's cell membranes.[15] Subsequently, awareness of the health benefits of essential fatty acids has dramatically increased since the 1980s.[16]

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".[17] This updated and modified their health risk advice letter of 2001 (see below).

The Canadian Food Inspection Agency has recognized the importance of DHA omega−3 and permits the following claim for DHA: "DHA, an omega−3 fatty acid, supports the normal physical development of the brain, eyes, and nerves primarily in children under two years of age."[18]

Historically, whole food diets contained sufficient amounts of omega−3, but because omega−3 is readily oxidized, the trend toward shelf-stable processed foods has led to a deficiency in omega−3 in manufactured foods.[19]

Nomenclature

Main article: Fatty acid § Nomenclature
 
Chemical structure of α-linolenic acid (ALA), a fatty acid with a chain of 18 carbons with three double bonds on carbons numbered 9, 12, and 15. The omega (ω) end of the chain is at carbon 18, and the double bond closest to the omega carbon begins at carbon 15 = 18−3. Hence, ALA is a ω−3 fatty acid with ω = 18.

The terms ω−3 ("omega−3") fatty acid and n−3 fatty acid are derived from the nomenclature of organic chemistry.[2][20] One way in which an unsaturated fatty acid is named is determined by the location, in its carbon chain, of the double bond which is closest to the methyl end of the molecule.[20] In general terminology, n (or ω) represents the locant of the methyl end of the molecule, while the number n−x (or ω−x) refers to the locant of its nearest double bond. Thus, in omega−3 fatty acids in particular, there is a double bond located at the carbon numbered 3, starting from the methyl end of the fatty acid chain. This classification scheme is useful since most chemical changes occur at the carboxyl end of the molecule, while the methyl group and its nearest double bond are unchanged in most chemical or enzymatic reactions.

In the expressions n−x or ω−x, the symbol is a minus sign rather than a hyphen (or dash), although it is never read as such. Also, the symbol n (or ω) represents the locant of the methyl end, counted from the carboxyl end of the fatty acid carbon chain. For instance, in an omega−3 fatty acid with 18 carbon atoms (see illustration), where the methyl end is at location 18 from the carboxyl end, n (or ω) represents the number 18, and the notation n−3 (or ω−3) represents the subtraction 18−3 = 15, where 15 is the locant of the double bond which is closest to the methyl end, counted from the carboxyl end of the chain.[20]

Although n and ω (omega) are synonymous, the IUPAC recommends that n be used to identify the highest carbon number of a fatty acid.[20] Nevertheless, the more common name – omega−3 fatty acid – is used in both the lay media and scientific literature.

Example

For example, α-linolenic acid (ALA; illustration) is an 18-carbon chain having three double bonds, the first being located at the third carbon from the methyl end of the fatty acid chain. Hence, it is an omega−3 fatty acid. Counting from the other end of the chain, that is the carboxyl end, the three double bonds are located at carbons 9, 12, and 15. These three locants are typically indicated as Δ9c, Δ12c, Δ15c, or cisΔ9, cisΔ12, cisΔ15, or cis-cis-cis-Δ9,12,15, where c or cis means that the double bonds have a cis configuration.

α-Linolenic acid is polyunsaturated (containing more than one double bond) and is also described by a lipid number, 18:3, meaning that there are 18 carbon atoms and 3 double bonds.[20]

Chemistry

 
Chemical structure of eicosapentaenoic acid (EPA)
 
Chemical structure of docosahexaenoic acid (DHA)

An omega−3 fatty acid is a fatty acid with multiple double bonds, where the first double bond is between the third and fourth carbon atoms from the end of the carbon atom chain. "Short-chain" omega−3 fatty acids have a chain of 18 carbon atoms or less, while "long-chain" omega−3 fatty acids have a chain of 20 or more.

Three omega−3 fatty acids are important in human physiology, α-linolenic acid (18:3, n-3; ALA), eicosapentaenoic acid (20:5, n-3; EPA), and docosahexaenoic acid (22:6, n-3; DHA).[21] 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 of omega−3 fatty acids

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

Common name Lipid number 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

Forms

Omega−3 fatty acids occur naturally in two forms, triglycerides and phospholipids. In the triglycerides, they, together with other fatty acids, are bonded to glycerol; three fatty acids are attached to glycerol. Phospholipid omega−3 is composed of two fatty acids attached to a phosphate group via glycerol.

The triglycerides can be converted to the free fatty acid or to methyl or ethyl esters, and the individual esters of omega−3 fatty acids are available.[clarification needed]

Biochemistry

Transporters

DHA in the form of lysophosphatidylcholine is transported into the brain by a membrane transport protein, MFSD2A, which is exclusively expressed in the endothelium of the blood–brain barrier.[22][23]

Mechanism of action

The 'essential' fatty acids were given their name when researchers found that they are essential to normal growth in young children and animals. The omega−3 fatty acid DHA, also known as docosahexaenoic acid, is found in high abundance in the human brain.[24] It is produced by a desaturation process, but humans lack the desaturase enzyme, which acts to insert double bonds at the ω6 and ω3 position.[24] Therefore, the ω6 and ω3 polyunsaturated fatty acids cannot be synthesized, are appropriately called essential fatty acids, and must be obtained from the diet.[24]

In 1964, it was discovered that enzymes found in sheep tissues convert omega−6 arachidonic acid into the inflammatory agent, prostaglandin E2,[25] which is involved in the immune response of traumatized and infected tissues.[26] By 1979, eicosanoids were further identified, including thromboxanes, prostacyclins, and leukotrienes.[26] The eicosanoids typically have a short period of activity in the body, starting with synthesis from fatty acids and ending with metabolism by enzymes. If the rate of synthesis exceeds the rate of metabolism, the excess eicosanoids may have deleterious effects.[26] Researchers found that certain omega−3 fatty acids are also converted into eicosanoids and docosanoids,[27] but at a slower rate. If both omega−3 and omega−6 fatty acids are present, they will "compete" to be transformed,[26] so the ratio of long-chain omega−3:omega−6 fatty acids directly affects the type of eicosanoids that are produced.[26]

Interconversion

Conversion efficiency of ALA to EPA and DHA

Humans can convert short-chain omega−3 fatty acids to long-chain forms (EPA, DHA) with an efficiency below 5%.[28][29] The omega−3 conversion efficiency is greater in women than in men, but less studied.[30] Higher ALA and DHA values found in plasma phospholipids of women may be due to the higher activity of desaturases, especially that of delta-6-desaturase.[31]

These conversions occur competitively with omega−6 fatty acids, which are essential closely related chemical analogues that are derived from linoleic acid. They both utilize the same desaturase and elongase proteins in order to synthesize inflammatory regulatory proteins.[32] The products of both pathways are vital for growth making a balanced diet of omega−3 and omega−6 important to an individual's health.[33] A balanced intake ratio of 1:1 was believed to be ideal in order for proteins to be able to synthesize both pathways sufficiently, but this has been controversial as of recent research.[34]

The conversion of ALA to EPA and further to DHA in humans has been reported to be limited, but varies with individuals.[2][35] Women have higher ALA-to-DHA conversion efficiency than men, which is presumed[36] to be due to the lower rate of use of dietary ALA for beta-oxidation. One preliminary study showed that EPA can be increased by lowering the amount of dietary linoleic acid, and DHA can be increased by elevating intake of dietary ALA.[37]

Omega−6 to omega−3 ratio

Main article: Essential fatty acid interactions

Human diet has changed rapidly in recent centuries resulting in a reported increased diet of omega−6 in comparison to omega−3.[38] The rapid evolution of human diet away from a 1:1 omega−3 and omega−6 ratio, such as during the Neolithic Agricultural Revolution, has presumably been too fast for humans to have adapted to biological profiles adept at balancing omega−3 and omega−6 ratios of 1:1.[39] This is commonly believed to be the reason why modern diets are correlated with many inflammatory disorders.[38] While omega−3 polyunsaturated fatty acids may be beneficial in preventing heart disease in humans, the level of omega−6 polyunsaturated fatty acids (and, therefore, the ratio) does not matter.[34][40]

Both omega−6 and omega−3 fatty acids are essential: 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.[41]

Metabolites of omega−6 are more inflammatory (esp. arachidonic acid) than those of omega−3. However, in terms of heart health omega-6 fatty acids are less harmful than they are presumed to be. A meta-analysis of six randomized trials found that replacing saturated fat with omega-6 fats reduced the risk of coronary events by 24%.[42]

A healthy ratio of omega-6 to omega-3 is needed; healthy ratios, according to some authors, range from 1:1 to 1:4.[43] Other authors believe that a ratio of 4:1 (4 times as much omega−6 as omega−3) is already healthy.[44][45]

Typical Western diets provide ratios of between 10:1 and 30:1 (i.e., dramatically higher levels of omega−6 than omega−3).[46] The ratios of omega−6 to omega−3 fatty acids in some common vegetable oils are: canola 2:1, hemp 2–3:1,[47] soybean 7:1, olive 3–13:1, sunflower (no omega−3), flax 1:3,[48] cottonseed (almost no omega−3), peanut (no omega−3), grapeseed oil (almost no omega−3) and corn oil 46:1.[49]

Dietary sources

Grams of omega−3 per 3oz (85g) serving[50]
Common name grams omega−3
Herring, sardines 1.3–2
Mackerel: Spanish/Atlantic/Pacific 1.1–1.7
Salmon 1.1–1.9
Halibut 0.60–1.12
Tuna 0.21–1.1
Swordfish 0.97
Greenshell/lipped mussels 0.95[51]
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
Red snapper 0.29
Shark 0.83
King mackerel 0.36
Hoki (blue grenadier) 0.41[51]
Gemfish 0.40[51]
Blue eye cod 0.31[51]
Sydney rock oysters 0.30[51]
Tuna, canned 0.23[51]
Snapper 0.22[51]
Eggs, large regular 0.109[51]
Strawberry or Kiwifruit 0.10–0.20
Broccoli 0.10–0.20
Barramundi, saltwater 0.100[51]
Giant tiger prawn 0.100[51]
Lean red meat 0.031[51]
Turkey 0.030[51]
Milk, regular 0.00[51]

Dietary recommendations

In the United States, the Institute of Medicine publishes 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. Because the physiological potency of EPA and 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.[52] The Institute of Medicine has not established a RDA or AI for EPA, DHA or the combination, so there is no Daily Value (DVs are derived from RDAs), no labeling of foods or supplements as providing a DV percentage of these fatty acids per serving, and no labeling a food or supplement as an excellent source, or "High in..."[citation needed] As for safety, there was insufficient evidence as of 2005 to set an upper tolerable limit for omega−3 fatty acids,[52] although the FDA has advised that adults can safely consume up to a total of 3 grams per day of combined DHA and EPA, with no more than 2 g from dietary supplements.[1]

The European Commission sponsored a working group to develop recommendations on dietary fat intake in pregnancy and lactation. In 2008, the working group published consensus recommendations,[53] including the following:

  • "pregnant and lactating women should aim to achieve an average dietary intake of at least 200 mg DHA/day"
  • "women of childbearing age should aim to consume one to two portions of sea fish per week, including oily fish"
  • "intake of the DHA precursor, α-linolenic acid, is far less effective with regard to DHA deposition in fetal brain than preformed DHA"

However, the seafood supply to meet these recommendations is currently too low in most European countries and if met would be unsustainable.[54]

In the EU, the EFSA publishes the Dietary Reference Values (DRVs), recommending Adequate Intake values for EPA+DHA and DHA:[55]

Dietary Reference Values (DRVs) for EPA+DHA and DHA
Age group (years) EPA+DHA (mg/day)1 DHA (mg/day)1
7-11 months2 100
1 100
2-3 250
4-6 250
7-10 250
11-14 250
15-17 250
≥18 250
Pregnancy 250 + 100—2003
Lactation 250 + 100—2003
^1 AI, Adequate Intake
^2 i.e. the second half of the first year of life (from the beginning of the 7th month to the 1st birthday)
^3 in addition to combined intakes of EPA and DHA of 250 mg/day

The American Heart Association (AHA) has made 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 two times per week; and "Treatment is reasonable" for those having been diagnosed with coronary heart disease. For the latter the AHA does not recommend a specific amount of EPA + DHA, although it notes that most trials were at or close to 1000 mg/day. The benefit appears to be on the order of a 9% decrease in relative risk.[56] The European Food Safety Authority (EFSA) approved a claim "EPA and DHA contributes to the normal function of the heart" for products that contain at least 250 mg EPA + DHA. The report did not address the issue of people with pre-existing heart disease. The World Health Organization recommends regular fish consumption (1-2 servings per week, equivalent to 200 to 500 mg/day EPA + DHA) as protective against coronary heart disease and ischaemic stroke.

Contamination

Heavy metal poisoning from consuming fish oil supplements is highly unlikely, because heavy metals (mercury, lead, nickel, arsenic, and cadmium) selectively bind with protein in the fish flesh rather than accumulate in the oil.[57][58]

However, other contaminants (PCBs, furans, dioxins, and PBDEs) might be found, especially in less-refined fish oil supplements.[59]

Throughout their history, the Council for Responsible Nutrition and the World Health Organization have published acceptability standards regarding contaminants in fish oil. The most stringent current standard is the International Fish Oils Standard.[60][non-primary source needed] Fish oils that are molecularly distilled under vacuum typically make this highest-grade; levels of contaminants are stated in parts per billion per trillion.[citation needed][61]

Rancidity

A 2022 study found that a number of products on the market used oxidised oils, with the rancidity often masked by flavourings. Another study in 2015 found that an average of 20% of products had excess oxidation. Whether rancid fish oil is harmful remains unclear. Some studies show that highly oxidised fish oil can have a negative impact on cholesterol levels. Animal testing showed that high doses have toxic effects. Furthermore, rancid oil is likely to be less effective than fresh fish oil.[62][63]

Fish

The most widely available dietary source of EPA and DHA is oily fish, such as salmon, herring, mackerel, anchovies, and sardines.[1] Oils from these fishes have around seven times as much omega−3 as omega−6. Other oily fish, such as tuna, also contain n-3 in somewhat lesser amounts.[1][64] Although fish are a dietary source of omega−3 fatty acids, fish do not synthesize omega−3 fatty acids, but rather obtain them via their food supply, including algae or plankton.[65] In order for farmed marine fish to have amounts of EPA and DHA comparable to those of wild-caught fish, their feed must be supplemented with EPA and DHA, most commonly in the form of fish oil. For this reason, 81% of the global fish oil supply in 2009 was consumed by aquaculture.[66]

Fish oil

See also: Fish oil and Cod liver oil
 
Fish oil capsules

Marine and freshwater fish oil vary in content of arachidonic acid, EPA and DHA.[67] They also differ in their effects on organ lipids.[67]

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.[68][69]

Krill

Krill oil is a source of omega−3 fatty acids.[70] The effect of krill oil, at a lower dose of EPA + DHA (62.8%), was demonstrated to be similar to that of fish oil on blood lipid levels and markers of inflammation in healthy humans.[71] While not an endangered species, krill are a mainstay of the diets of many ocean-based species including whales, causing environmental and scientific concerns about their sustainability.[72][73][74] Preliminary studies appear to indicate that the DHA and EPA omega−3 fatty acids found in krill oil may be more bio-available than in fish oil.[75] Additionally, krill oil contains astaxanthin, a marine-source keto-carotenoid antioxidant that may act synergistically with EPA and DHA.[76][77][78][79][12]

Plant sources

 
Chia is grown commercially for its seeds rich in ALA.
 
Flax seeds contain linseed oil which has high ALA content

Table 1. ALA content as the percentage of the seed oil.[80]

Common name Alternative name Linnaean name % ALA
kiwifruit (fruit) Chinese gooseberry Actinidia deliciosa 63[81]
perilla shiso Perilla frutescens 61
chia chia sage Salvia hispanica 58
linseed flax Linum usitatissimum 53[38] – 59[82]
lingonberry cowberry Vaccinium vitis-idaea 49
fig common fig Ficus carica 47.7[83]
camelina gold-of-pleasure Camelina sativa 36
purslane portulaca Portulaca oleracea 35
black raspberry Rubus occidentalis 33
hempseed Cannabis sativa 19
canola rapeseed mostly Brassica napus 9[38] – 11

Table 2. ALA content as the percentage of the whole food.[38][84]

Common name Linnaean name % ALA
linseed Linum usitatissimum 18.1
hempseed Cannabis sativa 8.7
butternut Juglans cinerea 8.7
Persian walnut Juglans regia 6.3
pecan Carya illinoinensis 0.6
hazelnut Corylus avellana 0.1

Linseed (or flaxseed) (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.[85] A portion of this is converted by the body to EPA and DHA, though the actual converted percentage may differ between men and women.[86]

In 2013, Rothamsted Research in the UK reported they had developed a genetically modified form of the plant 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.[87][88]

Seaweed and Algae are unique plant sources of EPA and DHA, Omega 3 fats that are typically found in fish. This makes them particularly beneficial for vegans. "[1]"

Eggs

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.[89] 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.[90]

The addition of flax and canola seeds, both good sources of alpha-linolenic acid, to the diets of laying chickens, increases the omega−3 content of the eggs, predominantly DHA.[91] However, this enrichment could lead to an increment of lipid oxidation in the eggs if the seeds are used in higher doses, without using an appropriate antioxidant.[92]

The addition of green algae or seaweed to the diets boosts the content of DHA and EPA, 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".[93]

Meat

Omega−3 fatty acids are formed in the chloroplasts of green leaves and algae. While seaweeds and algae are the sources of omega−3 fatty acids present in fish, grass is the source of omega−3 fatty acids present in grass-fed animals.[94] 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.[95]

The omega−6:omega−3 ratio of grass-fed beef is about 2:1, making it a more useful source of omega−3 than grain-fed beef, which usually has a ratio of 4:1.[96]

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 minerals calcium, magnesium, and potassium, 193% higher in total omega−3s, 117% higher in CLA (cis-9, trans-11 octadecenoic acid, a conjugated linoleic acid, which is a potential cancer fighter), 90% higher in vaccenic acid (which can be transformed into CLA), lower in the saturated fats, and has a healthier ratio of omega−6 to omega−3 fatty acids (1.65 vs 4.84). Protein and cholesterol content were equal.[96]

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.[97]

Kangaroo meat is also a source of omega−3, with fillet and steak containing 74 mg per 100 g of raw meat.[98]

Seal oil

Seal oil is a source of EPA, DPA, and DHA, and is commonly used in Arctic regions. According to Health Canada, it helps to support the development of the brain, eyes, and nerves in children up to 12 years of age.[99] Like all seal products, it is not allowed to be imported into the European Union.[100]

A Canadian company, FeelGood Natural Health, pleaded guilty in 2023 to illegally selling seal oil capsules to American consumers. The company sold over 900 bottles of the capsules, worth over $10,000. Seal oil is made from the blubber of dead seals, and is illegal to sell in the United States under the Marine Mammal Protection Act. The global population of harp seals stands at around 7 million, and they have been hunted in Canada for thousands of years. FeelGood was sentenced to pay a fine of $20,000 and three years of probation.[101]

Other sources

 
Schizochytrium-based omega-3 supplements

A trend in the early 21st century was to fortify food with omega−3 fatty acids.[102][103] The microalgae Crypthecodinium cohnii and Schizochytrium are rich sources of DHA, but not EPA, and can be produced commercially in bioreactors for use as food additives.[102] Oil from brown algae (kelp) is a source of EPA.[104] The alga Nannochloropsis also has high levels of EPA.[105]

Health effects of omega-3 supplementation

The association between supplementation and a lower risk of all-cause mortality is inconclusive.[11][106]

Cancer

There is insufficient evidence that supplementation with omega−3 fatty acids has an effect on different cancers.[1][9][41][107] Omega-3 supplements do not improve body weight, muscle maintenance or quality of life in cancer patients.[108]

Cardiovascular disease

Moderate and high quality evidence from a 2020 review showed that EPA and DHA, such as that found in omega−3 polyunsaturated fatty acid supplements, does not appear to improve mortality or cardiovascular health.[8] There is weak evidence indicating that α-linolenic acid may be associated with a small reduction in the risk of a cardiovascular event or the risk of arrhythmia.[2][8]

A 2018 meta-analysis found no support that daily intake of one gram of omega−3 fatty acid in individuals with a history of coronary heart disease prevents fatal coronary heart disease, nonfatal myocardial infarction or any other vascular event.[11] However, omega−3 fatty acid supplementation greater than one gram daily for at least a year may be protective against cardiac death, sudden death, and myocardial infarction in people who have a history of cardiovascular disease.[109] No protective effect against the development of stroke or all-cause mortality was seen in this population.[109]

Fish oil supplementation has not been shown to benefit revascularization or abnormal heart rhythms and has no effect on heart failure hospital admission rates.[110] Furthermore, fish oil supplement studies have failed to support claims of preventing heart attacks or strokes.[12] In the EU, a review by the European Medicines Agency of omega−3 fatty acid medicines containing a combination of an ethyl ester of eicosapentaenoic acid and docosahexaenoic acid at a dose of 1 g per day concluded that these medicines are not effective in secondary prevention of heart problems in patients who have had a myocardial infarction.[111]

Evidence suggests that omega−3 fatty acids modestly lower blood pressure (systolic and diastolic) in people with hypertension and in people with normal blood pressure.[112][113] Omega−3 fatty acids can also reduce heart rate,[114] an emerging risk factor. Some evidence suggests that people with certain circulatory problems, such as varicose veins, may benefit from the consumption of EPA and DHA, which may stimulate blood circulation and increase the breakdown of fibrin, a protein involved in blood clotting and scar formation. Omega−3 fatty acids reduce blood triglyceride levels, but do not significantly change the level of LDL cholesterol or HDL cholesterol.[115][116] The American Heart Association position (2011) is that borderline elevated triglycerides, defined as 150–199 mg/dL, can be lowered by 0.5–1.0 grams of EPA and DHA per day; high triglycerides 200–499 mg/dL benefit from 1–2 g/day; and >500 mg/dL be treated under a physician's supervision with 2–4 g/day using a prescription product.[117] In this population omega−3 fatty acid supplementation decreases the risk of heart disease by about 25%.[118]

A 2019 review found that omega-3 fatty acid supplements make little or no difference to cardiovascular mortality and that patients with myocardial infarction yield no benefit in taking the supplements.[119] A 2021 review found that omega-3 supplementation did not affect cardiovascular disease outcomes.[10] A 2021 meta-analysis showed that use of marine omega-3 supplementation was associated with an increased risk of atrial fibrillation, with the risk appearing to increase for doses greater than one gram per day.[120]

Chronic kidney disease

In people with chronic kidney disease (CKD) who require hemodialysis, there is a risk that vascular blockage due to clotting, may prevent dialysis therapy from being possible. Omega-3 fatty acids contribute to the production of eicosanoid molecules that reduce clotting. However, a Cochrane review in 2018 did not find clear evidence that omega-3 supplementation has any impact on the prevention of vascular blockage in people with CKD.[121] There was also moderate certainty that supplementation did not prevent hospitalisation or death within a 12-month period.[121]

Stroke

A 2022 Cochrane review of controlled trials did not find clear evidence that marine-derived omega-3 supplementation improves cognitive and physical recovery or social, and emotional wellbeing following stroke diagnosis, nor prevents stroke recurrence and mortality.[13] In this review, mood appeared to worsen slightly among those receiving 3g fish oil supplementation for 12 weeks; psychometric scores changed by 1.41 (0.07 to 2.75) points less than those receiving palm and soy oil.[13] However, this represented only a single small study and was not observed in a study lasting more than 3 months. Overall, the review was limited by the low number of high-quality evidence available.

Inflammation

A 2013 systematic review found tentative evidence of benefit for lowering inflammation levels in healthy adults and in people with one or more biomarkers of metabolic syndrome.[122] Consumption of omega−3 fatty acids from marine sources lowers blood markers of inflammation such as C-reactive protein, interleukin 6, and TNF alpha.[123][124][125]

For rheumatoid arthritis, one systematic review found consistent but modest evidence for the effect of 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.[126] The American College of Rheumatology has stated that there may be modest benefit from the 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.[127] The National Center for Complementary and Integrative Health has concluded that "supplements containing omega−3 fatty acids ... may help relieve rheumatoid arthritis symptoms" but warns that such supplements "may interact with drugs that affect blood clotting".[128]

Developmental disabilities

One meta-analysis concluded that omega−3 fatty acid supplementation demonstrated a modest effect for improving ADHD symptoms.[129] 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",[130] while a different review found "insufficient evidence to draw any conclusion about the use of PUFAs for children with specific learning disorders".[131] Another review concluded that the evidence is inconclusive for the use of omega−3 fatty acids in behavior and non-neurodegenerative neuropsychiatric disorders such as ADHD and depression.[132]

A 2015 meta-analysis of the effect of omega−3 supplementation during pregnancy did not demonstrate a decrease in the rate of preterm birth or improve outcomes in women with singleton pregnancies with no prior preterm births.[133] A 2018 Cochrane systematic review with moderate to high quality of evidence suggested that omega−3 fatty acids may reduce risk of perinatal death, risk of low body weight babies; and possibly mildly increased LGA babies.[134]

A 2021 umbrella review with moderate to high quality of evidence suggested that "omega-3 supplementation during pregnancy can exert favorable effects against pre-eclampsia, low-birth weight, pre-term delivery, and post-partum depression, and can improve anthropometric measures, immune system, and visual activity in infants and cardiometabolic risk factors in pregnant mothers."[135]

Mental health

Omega-3 supplementation has not been shown to significantly affect symptoms of anxiety, major depressive disorder or schizophrenia.[136][137] A 2021 Cochrane review concluded that there is not "sufficient high‐certainty evidence to determine the effects of n‐3PUFAs as a treatment for MDD".[138] Omega−3 fatty acids have also been investigated as an add-on for the treatment of depression associated with bipolar disorder although there is limited data available.[139] Two reviews have suggested that omega-3 fatty acid supplementation significantly improves depressive symptoms in perinatal women.[135][140]

In contrast to dietary supplementation studies, there is significant difficulty in interpreting the literature regarding dietary intake of omega−3 fatty acids (e.g. from fish) due to participant recall and systematic differences in diets.[141] There is also controversy as to the efficacy of omega−3, with many meta-analysis papers finding heterogeneity among results which can be explained mostly by publication bias.[142][143] A significant correlation between shorter treatment trials was associated with increased omega−3 efficacy for treating depressed symptoms further implicating bias in publication.[143]

Cognitive aging

A 2016 Cochrane review found no convincing evidence for the use of omega‐3 PUFA supplements in treatment of Alzheimer's disease or dementia.[144] There is preliminary evidence of effect on mild cognitive problems, but none supporting an effect in healthy people or those with dementia.[145][146] A 2020 review suggested that omega 3 supplementation has no effect on global cognitive function but has a mild benefit in improving memory in non-demented adults.[147]

A 2022 review found promising evidence for prevention of cognitive decline in people who regularly eat long-chain omega 3 rich foods. Conversely, clinical trials with participants already diagnosed with Alzheimer's show no effect.[148]

Brain and visual functions

Brain function and vision rely on dietary intake of DHA to support a broad range of cell membrane properties, particularly in grey matter, which is rich in membranes.[149][150] A major structural component of the mammalian brain, DHA is the most abundant omega−3 fatty acid in the brain.[151][152] Omega 3 PUFA supplementation has no effect on macular degeneration or development of visual loss.[153]

Atopic diseases

Results of studies investigating the role of LCPUFA supplementation and LCPUFA status in the prevention and therapy of atopic diseases (allergic rhinoconjunctivitis, atopic dermatitis, and allergic asthma) are controversial; therefore, as of 2013 it could not be stated either that the nutritional intake of n−3 fatty acids has a clear preventive or therapeutic role, or that the intake of n-6 fatty acids has a promoting role in the context of atopic diseases.[154]

Phenylketonuria and omega-3 intake

People with PKU often have low intake of omega−3 fatty acids, because nutrients rich in omega−3 fatty acids are excluded from their diet due to high protein content.[155]

Asthma

As of 2015, there was no evidence that taking omega−3 supplements can prevent asthma attacks in children.[156]

Diabetes

A 2019 review found that omega-3 supplements have no effect on prevention and treatment of type 2 diabetes.[157][158]

See also

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Further reading

  • Allport S (September 2006). The Queen of Fats: Why Omega−3s Were Removed from the Western Diet and What We Can Do to Replace Them. University of California Press. ISBN 978-0-520-24282-1. OCLC 801139991.
  • Chow CK (2001). Fatty Acids in Foods and Their Health Implications. New York: Routledge Publishing. OCLC 25508943.
  • Clover C (2004). The End of the Line: How overfishing is changing the world and what we eat. London: Ebury Press. ISBN 0-09-189780-7. OCLC 67383509.
  • Greenberg P (2018). The Omega Principle: Seafood and the Quest for a Long Life and a Healthier Planet. New York: Penguin Press. ISBN 9781594206344. OCLC 1007552654.
  • Stoll AL (2001). The Omega−3 Connection: how you can restore your body's natural balance and treat depression. Simon & Schuster. ISBN 0-684-87138-6. OCLC 670441405.

External links

  •   Media related to Omega-3 fatty acids at Wikimedia Commons

August 22, 2023
omega, fatty, acid, also, omega, acid, ethyl, esters, omega, fatty, acids, also, called, omega, oils, fatty, acids, fatty, acids, polyunsaturated, fatty, acids, pufas, characterized, presence, double, bond, three, atoms, away, from, terminal, methyl, group, th. See also Omega 3 acid ethyl esters Omega 3 fatty acids also called Omega 3 oils w 3 fatty acids or n 3 fatty acids 1 are polyunsaturated fatty acids PUFAs characterized by the presence of a double bond three atoms away from the terminal methyl group in their chemical structure 2 They are widely distributed in nature being important constituents of animal lipid metabolism and they play an important role in the human diet and in human physiology 2 3 The three types of omega 3 fatty acids involved in human physiology are a linolenic acid ALA eicosapentaenoic acid EPA and docosahexaenoic acid DHA ALA can be found in plants while DHA and EPA are found in algae and fish Marine algae and phytoplankton are primary sources of omega 3 fatty acids 4 DHA and EPA accumulate in fish that eat these algae 5 Common sources of plant oils containing ALA include walnuts edible seeds and flaxseeds as well as hempseed oil while sources of EPA and DHA include fish and fish oils 1 and algae oil Mammals are unable to synthesize the essential omega 3 fatty acid ALA and can only obtain it through diet However they can use ALA when available to form EPA and DHA by creating additional double bonds along its carbon chain desaturation and extending it elongation Namely ALA 18 carbons and 3 double bonds is used to make EPA 20 carbons and 5 double bonds which is then used to make DHA 22 carbons and 6 double bonds 1 2 The ability to make the longer chain omega 3 fatty acids from ALA may be impaired in aging 6 In foods exposed to air unsaturated fatty acids are vulnerable to oxidation and rancidity 2 7 There is no high quality evidence that dietary supplementation with omega 3 fatty acids reduces the risk of cancer or cardiovascular disease 8 9 10 Furthermore fish oil supplement studies have failed to support claims of preventing heart attacks or strokes or any vascular disease outcomes 11 12 13 Contents 1 History 2 Nomenclature 2 1 Example 3 Chemistry 3 1 List of omega 3 fatty acids 4 Forms 5 Biochemistry 5 1 Transporters 6 Mechanism of action 6 1 Interconversion 6 1 1 Conversion efficiency of ALA to EPA and DHA 6 1 2 Omega 6 to omega 3 ratio 7 Dietary sources 7 1 Dietary recommendations 7 2 Contamination 7 3 Rancidity 7 4 Fish 7 4 1 Fish oil 7 5 Krill 7 6 Plant sources 7 7 Eggs 7 8 Meat 7 9 Seal oil 7 10 Other sources 8 Health effects of omega 3 supplementation 8 1 Cancer 8 2 Cardiovascular disease 8 3 Chronic kidney disease 8 4 Stroke 8 5 Inflammation 8 6 Developmental disabilities 8 7 Mental health 8 8 Cognitive aging 8 9 Brain and visual functions 8 10 Atopic diseases 8 11 Phenylketonuria and omega 3 intake 8 12 Asthma 8 13 Diabetes 9 See also 10 References 11 Further reading 12 External linksHistory EditIn 1929 George and Mildred Burr discovered that fatty acids were critical to health If fatty acids were absent from the diet a life threatening deficiency syndrome ensued The Burrs coined the phrase essential fatty acids 14 Since then researchers have shown a growing interest in unsaturated essential fatty acids as they form the framework for the organism s cell membranes 15 Subsequently awareness of the health benefits of essential fatty acids has dramatically increased since the 1980s 16 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 17 This updated and modified their health risk advice letter of 2001 see below The Canadian Food Inspection Agency has recognized the importance of DHA omega 3 and permits the following claim for DHA DHA an omega 3 fatty acid supports the normal physical development of the brain eyes and nerves primarily in children under two years of age 18 Historically whole food diets contained sufficient amounts of omega 3 but because omega 3 is readily oxidized the trend toward shelf stable processed foods has led to a deficiency in omega 3 in manufactured foods 19 Nomenclature EditMain article Fatty acid Nomenclature Chemical structure of a linolenic acid ALA a fatty acid with a chain of 18 carbons with three double bonds on carbons numbered 9 12 and 15 The omega w end of the chain is at carbon 18 and the double bond closest to the omega carbon begins at carbon 15 18 3 Hence ALA is a w 3 fatty acid with w 18 The terms w 3 omega 3 fatty acid and n 3 fatty acid are derived from the nomenclature of organic chemistry 2 20 One way in which an unsaturated fatty acid is named is determined by the location in its carbon chain of the double bond which is closest to the methyl end of the molecule 20 In general terminology n or w represents the locant of the methyl end of the molecule while the number n x or w x refers to the locant of its nearest double bond Thus in omega 3 fatty acids in particular there is a double bond located at the carbon numbered 3 starting from the methyl end of the fatty acid chain This classification scheme is useful since most chemical changes occur at the carboxyl end of the molecule while the methyl group and its nearest double bond are unchanged in most chemical or enzymatic reactions In the expressions n x or w x the symbol is a minus sign rather than a hyphen or dash although it is never read as such Also the symbol n or w represents the locant of the methyl end counted from the carboxyl end of the fatty acid carbon chain For instance in an omega 3 fatty acid with 18 carbon atoms see illustration where the methyl end is at location 18 from the carboxyl end n or w represents the number 18 and the notation n 3 or w 3 represents the subtraction 18 3 15 where 15 is the locant of the double bond which is closest to the methyl end counted from the carboxyl end of the chain 20 Although n and w omega are synonymous the IUPAC recommends that n be used to identify the highest carbon number of a fatty acid 20 Nevertheless the more common name omega 3 fatty acid is used in both the lay media and scientific literature Example Edit For example a linolenic acid ALA illustration is an 18 carbon chain having three double bonds the first being located at the third carbon from the methyl end of the fatty acid chain Hence it is an omega 3 fatty acid Counting from the other end of the chain that is the carboxyl end the three double bonds are located at carbons 9 12 and 15 These three locants are typically indicated as D9c D12c D15c or cisD9 cisD12 cisD15 or cis cis cis D9 12 15 where c or cis means that the double bonds have a cis configuration a Linolenic acid is polyunsaturated containing more than one double bond and is also described by a lipid number 18 3 meaning that there are 18 carbon atoms and 3 double bonds 20 Chemistry Edit Chemical structure of eicosapentaenoic acid EPA Chemical structure of docosahexaenoic acid DHA An omega 3 fatty acid is a fatty acid with multiple double bonds where the first double bond is between the third and fourth carbon atoms from the end of the carbon atom chain Short chain omega 3 fatty acids have a chain of 18 carbon atoms or less while long chain omega 3 fatty acids have a chain of 20 or more Three omega 3 fatty acids are important in human physiology a linolenic acid 18 3 n 3 ALA eicosapentaenoic acid 20 5 n 3 EPA and docosahexaenoic acid 22 6 n 3 DHA 21 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 CH2 so that there are two single bonds between each pair of adjacent double bonds List of 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 number Chemical nameHexadecatrienoic acid HTA 16 3 n 3 all cis 7 10 13 hexadecatrienoic acida Linolenic acid ALA 18 3 n 3 all cis 9 12 15 octadecatrienoic acidStearidonic acid SDA 18 4 n 3 all cis 6 9 12 15 octadecatetraenoic acidEicosatrienoic acid ETE 20 3 n 3 all cis 11 14 17 eicosatrienoic acidEicosatetraenoic acid ETA 20 4 n 3 all cis 8 11 14 17 eicosatetraenoic acidEicosapentaenoic acid EPA 20 5 n 3 all cis 5 8 11 14 17 eicosapentaenoic acidHeneicosapentaenoic acid HPA 21 5 n 3 all cis 6 9 12 15 18 heneicosapentaenoic acidDocosapentaenoic acid DPA Clupanodonic acid 22 5 n 3 all cis 7 10 13 16 19 docosapentaenoic acidDocosahexaenoic acid DHA 22 6 n 3 all cis 4 7 10 13 16 19 docosahexaenoic acidTetracosapentaenoic acid 24 5 n 3 all cis 9 12 15 18 21 tetracosapentaenoic acidTetracosahexaenoic acid Nisinic acid 24 6 n 3 all cis 6 9 12 15 18 21 tetracosahexaenoic acidForms EditOmega 3 fatty acids occur naturally in two forms triglycerides and phospholipids In the triglycerides they together with other fatty acids are bonded to glycerol three fatty acids are attached to glycerol Phospholipid omega 3 is composed of two fatty acids attached to a phosphate group via glycerol The triglycerides can be converted to the free fatty acid or to methyl or ethyl esters and the individual esters of omega 3 fatty acids are available clarification needed Biochemistry EditTransporters Edit DHA in the form of lysophosphatidylcholine is transported into the brain by a membrane transport protein MFSD2A which is exclusively expressed in the endothelium of the blood brain barrier 22 23 Mechanism of action EditThe essential fatty acids were given their name when researchers found that they are essential to normal growth in young children and animals The omega 3 fatty acid DHA also known as docosahexaenoic acid is found in high abundance in the human brain 24 It is produced by a desaturation process but humans lack the desaturase enzyme which acts to insert double bonds at the w6 and w3 position 24 Therefore the w6 and w3 polyunsaturated fatty acids cannot be synthesized are appropriately called essential fatty acids and must be obtained from the diet 24 In 1964 it was discovered that enzymes found in sheep tissues convert omega 6 arachidonic acid into the inflammatory agent prostaglandin E2 25 which is involved in the immune response of traumatized and infected tissues 26 By 1979 eicosanoids were further identified including thromboxanes prostacyclins and leukotrienes 26 The eicosanoids typically have a short period of activity in the body starting with synthesis from fatty acids and ending with metabolism by enzymes If the rate of synthesis exceeds the rate of metabolism the excess eicosanoids may have deleterious effects 26 Researchers found that certain omega 3 fatty acids are also converted into eicosanoids and docosanoids 27 but at a slower rate If both omega 3 and omega 6 fatty acids are present they will compete to be transformed 26 so the ratio of long chain omega 3 omega 6 fatty acids directly affects the type of eicosanoids that are produced 26 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 28 29 The omega 3 conversion efficiency is greater in women than in men but less studied 30 Higher ALA and DHA values found in plasma phospholipids of women may be due to the higher activity of desaturases especially that of delta 6 desaturase 31 These conversions occur competitively with omega 6 fatty acids which are essential closely related chemical analogues that are derived from linoleic acid They both utilize the same desaturase and elongase proteins in order to synthesize inflammatory regulatory proteins 32 The products of both pathways are vital for growth making a balanced diet of omega 3 and omega 6 important to an individual s health 33 A balanced intake ratio of 1 1 was believed to be ideal in order for proteins to be able to synthesize both pathways sufficiently but this has been controversial as of recent research 34 The conversion of ALA to EPA and further to DHA in humans has been reported to be limited but varies with individuals 2 35 Women have higher ALA to DHA conversion efficiency than men which is presumed 36 to be due to the lower rate of use of dietary ALA for beta oxidation One preliminary study showed that EPA can be increased by lowering the amount of dietary linoleic acid and DHA can be increased by elevating intake of dietary ALA 37 Omega 6 to omega 3 ratio Edit Main article Essential fatty acid interactions Human diet has changed rapidly in recent centuries resulting in a reported increased diet of omega 6 in comparison to omega 3 38 The rapid evolution of human diet away from a 1 1 omega 3 and omega 6 ratio such as during the Neolithic Agricultural Revolution has presumably been too fast for humans to have adapted to biological profiles adept at balancing omega 3 and omega 6 ratios of 1 1 39 This is commonly believed to be the reason why modern diets are correlated with many inflammatory disorders 38 While omega 3 polyunsaturated fatty acids may be beneficial in preventing heart disease in humans the level of omega 6 polyunsaturated fatty acids and therefore the ratio does not matter 34 40 Both omega 6 and omega 3 fatty acids are essential 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 41 Metabolites of omega 6 are more inflammatory esp arachidonic acid than those of omega 3 However in terms of heart health omega 6 fatty acids are less harmful than they are presumed to be A meta analysis of six randomized trials found that replacing saturated fat with omega 6 fats reduced the risk of coronary events by 24 42 A healthy ratio of omega 6 to omega 3 is needed healthy ratios according to some authors range from 1 1 to 1 4 43 Other authors believe that a ratio of 4 1 4 times as much omega 6 as omega 3 is already healthy 44 45 Typical Western diets provide ratios of between 10 1 and 30 1 i e dramatically higher levels of omega 6 than omega 3 46 The ratios of omega 6 to omega 3 fatty acids in some common vegetable oils are canola 2 1 hemp 2 3 1 47 soybean 7 1 olive 3 13 1 sunflower no omega 3 flax 1 3 48 cottonseed almost no omega 3 peanut no omega 3 grapeseed oil almost no omega 3 and corn oil 46 1 49 Dietary sources EditGrams of omega 3 per 3oz 85g serving 50 Common name grams omega 3Herring sardines 1 3 2Mackerel Spanish Atlantic Pacific 1 1 1 7Salmon 1 1 1 9Halibut 0 60 1 12Tuna 0 21 1 1Swordfish 0 97Greenshell lipped mussels 0 95 51 Tilefish 0 9Tuna canned light 0 17 0 24Pollock 0 45Cod 0 15 0 24Catfish 0 22 0 3Flounder 0 48Grouper 0 23Mahi mahi 0 13Red snapper 0 29Shark 0 83King mackerel 0 36Hoki blue grenadier 0 41 51 Gemfish 0 40 51 Blue eye cod 0 31 51 Sydney rock oysters 0 30 51 Tuna canned 0 23 51 Snapper 0 22 51 Eggs large regular 0 109 51 Strawberry or Kiwifruit 0 10 0 20Broccoli 0 10 0 20Barramundi saltwater 0 100 51 Giant tiger prawn 0 100 51 Lean red meat 0 031 51 Turkey 0 030 51 Milk regular 0 00 51 Dietary recommendations Edit In the United States the Institute of Medicine publishes 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 a 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 Because the physiological potency of EPA and 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 52 The Institute of Medicine has not established a RDA or AI for EPA DHA or the combination so there is no Daily Value DVs are derived from RDAs no labeling of foods or supplements as providing a DV percentage of these fatty acids per serving and no labeling a food or supplement as an excellent source or High in citation needed As for safety there was insufficient evidence as of 2005 to set an upper tolerable limit for omega 3 fatty acids 52 although the FDA has advised that adults can safely consume up to a total of 3 grams per day of combined DHA and EPA with no more than 2 g from dietary supplements 1 The European Commission sponsored a working group to develop recommendations on dietary fat intake in pregnancy and lactation In 2008 the working group published consensus recommendations 53 including the following pregnant and lactating women should aim to achieve an average dietary intake of at least 200 mg DHA day women of childbearing age should aim to consume one to two portions of sea fish per week including oily fish intake of the DHA precursor a linolenic acid is far less effective with regard to DHA deposition in fetal brain than preformed DHA However the seafood supply to meet these recommendations is currently too low in most European countries and if met would be unsustainable 54 In the EU the EFSA publishes the Dietary Reference Values DRVs recommending Adequate Intake values for EPA DHA and DHA 55 Dietary Reference Values DRVs for EPA DHA and DHA Age group years EPA DHA mg day 1 DHA mg day 17 11 months2 1001 1002 3 2504 6 2507 10 25011 14 25015 17 250 18 250Pregnancy 250 100 2003Lactation 250 100 2003 1 AI Adequate Intake 2 i e the second half of the first year of life from the beginning of the 7th month to the 1st birthday 3 in addition to combined intakes of EPA and DHA of 250 mg dayThe American Heart Association AHA has made 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 two times per week and Treatment is reasonable for those having been diagnosed with coronary heart disease For the latter the AHA does not recommend a specific amount of EPA DHA although it notes that most trials were at or close to 1000 mg day The benefit appears to be on the order of a 9 decrease in relative risk 56 The European Food Safety Authority EFSA approved a claim EPA and DHA contributes to the normal function of the heart for products that contain at least 250 mg EPA DHA The report did not address the issue of people with pre existing heart disease The World Health Organization recommends regular fish consumption 1 2 servings per week equivalent to 200 to 500 mg day EPA DHA as protective against coronary heart disease and ischaemic stroke Contamination Edit Heavy metal poisoning from consuming fish oil supplements is highly unlikely because heavy metals mercury lead nickel arsenic and cadmium selectively bind with protein in the fish flesh rather than accumulate in the oil 57 58 However other contaminants PCBs furans dioxins and PBDEs might be found especially in less refined fish oil supplements 59 Throughout their history the Council for Responsible Nutrition and the World Health Organization have published acceptability standards regarding contaminants in fish oil The most stringent current standard is the International Fish Oils Standard 60 non primary source needed Fish oils that are molecularly distilled under vacuum typically make this highest grade levels of contaminants are stated in parts per billion per trillion citation needed 61 Rancidity Edit A 2022 study found that a number of products on the market used oxidised oils with the rancidity often masked by flavourings Another study in 2015 found that an average of 20 of products had excess oxidation Whether rancid fish oil is harmful remains unclear Some studies show that highly oxidised fish oil can have a negative impact on cholesterol levels Animal testing showed that high doses have toxic effects Furthermore rancid oil is likely to be less effective than fresh fish oil 62 63 Fish Edit The most widely available dietary source of EPA and DHA is oily fish such as salmon herring mackerel anchovies and sardines 1 Oils from these fishes have around seven times as much omega 3 as omega 6 Other oily fish such as tuna also contain n 3 in somewhat lesser amounts 1 64 Although fish are a dietary source of omega 3 fatty acids fish do not synthesize omega 3 fatty acids but rather obtain them via their food supply including algae or plankton 65 In order for farmed marine fish to have amounts of EPA and DHA comparable to those of wild caught fish their feed must be supplemented with EPA and DHA most commonly in the form of fish oil For this reason 81 of the global fish oil supply in 2009 was consumed by aquaculture 66 Fish oil Edit See also Fish oil and Cod liver oil Fish oil capsulesMarine and freshwater fish oil vary in content of arachidonic acid EPA and DHA 67 They also differ in their effects on organ lipids 67 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 68 69 Krill Edit Krill oil is a source of omega 3 fatty acids 70 The effect of krill oil at a lower dose of EPA DHA 62 8 was demonstrated to be similar to that of fish oil on blood lipid levels and markers of inflammation in healthy humans 71 While not an endangered species krill are a mainstay of the diets of many ocean based species including whales causing environmental and scientific concerns about their sustainability 72 73 74 Preliminary studies appear to indicate that the DHA and EPA omega 3 fatty acids found in krill oil may be more bio available than in fish oil 75 Additionally krill oil contains astaxanthin a marine source keto carotenoid antioxidant that may act synergistically with EPA and DHA 76 77 78 79 12 Plant sources Edit Chia is grown commercially for its seeds rich in ALA Flax seeds contain linseed oil which has high ALA contentTable 1 ALA content as the percentage of the seed oil 80 Common name Alternative name Linnaean name ALAkiwifruit fruit Chinese gooseberry Actinidia deliciosa 63 81 perilla shiso Perilla frutescens 61chia chia sage Salvia hispanica 58linseed flax Linum usitatissimum 53 38 59 82 lingonberry cowberry Vaccinium vitis idaea 49fig common fig Ficus carica 47 7 83 camelina gold of pleasure Camelina sativa 36purslane portulaca Portulaca oleracea 35black raspberry Rubus occidentalis 33hempseed Cannabis sativa 19canola rapeseed mostly Brassica napus 9 38 11Table 2 ALA content as the percentage of the whole food 38 84 Common name Linnaean name ALAlinseed Linum usitatissimum 18 1hempseed Cannabis sativa 8 7butternut Juglans cinerea 8 7Persian walnut Juglans regia 6 3pecan Carya illinoinensis 0 6hazelnut Corylus avellana 0 1Linseed or flaxseed 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 85 A portion of this is converted by the body to EPA and DHA though the actual converted percentage may differ between men and women 86 In 2013 Rothamsted Research in the UK reported they had developed a genetically modified form of the plant 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 87 88 Seaweed and Algae are unique plant sources of EPA and DHA Omega 3 fats that are typically found in fish This makes them particularly beneficial for vegans 1 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 89 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 90 The addition of flax and canola seeds both good sources of alpha linolenic acid to the diets of laying chickens increases the omega 3 content of the eggs predominantly DHA 91 However this enrichment could lead to an increment of lipid oxidation in the eggs if the seeds are used in higher doses without using an appropriate antioxidant 92 The addition of green algae or seaweed to the diets boosts the content of DHA and EPA 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 93 Meat Edit Omega 3 fatty acids are formed in the chloroplasts of green leaves and algae While seaweeds and algae are the sources of omega 3 fatty acids present in fish grass is the source of omega 3 fatty acids present in grass fed animals 94 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 95 The omega 6 omega 3 ratio of grass fed beef is about 2 1 making it a more useful source of omega 3 than grain fed beef which usually has a ratio of 4 1 96 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 minerals calcium magnesium and potassium 193 higher in total omega 3s 117 higher in CLA cis 9 trans 11 octadecenoic acid a conjugated linoleic acid which is a potential cancer fighter 90 higher in vaccenic acid which can be transformed into CLA lower in the saturated fats and has a healthier ratio of omega 6 to omega 3 fatty acids 1 65 vs 4 84 Protein and cholesterol content were equal 96 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 97 Kangaroo meat is also a source of omega 3 with fillet and steak containing 74 mg per 100 g of raw meat 98 Seal oil Edit Seal oil is a source of EPA DPA and DHA and is commonly used in Arctic regions According to Health Canada it helps to support the development of the brain eyes and nerves in children up to 12 years of age 99 Like all seal products it is not allowed to be imported into the European Union 100 A Canadian company FeelGood Natural Health pleaded guilty in 2023 to illegally selling seal oil capsules to American consumers The company sold over 900 bottles of the capsules worth over 10 000 Seal oil is made from the blubber of dead seals and is illegal to sell in the United States under the Marine Mammal Protection Act The global population of harp seals stands at around 7 million and they have been hunted in Canada for thousands of years FeelGood was sentenced to pay a fine of 20 000 and three years of probation 101 Other sources Edit Schizochytrium based omega 3 supplementsA trend in the early 21st century was to fortify food with omega 3 fatty acids 102 103 The microalgae Crypthecodinium cohnii and Schizochytrium are rich sources of DHA but not EPA and can be produced commercially in bioreactors for use as food additives 102 Oil from brown algae kelp is a source of EPA 104 The alga Nannochloropsis also has high levels of EPA 105 Health effects of omega 3 supplementation EditThe association between supplementation and a lower risk of all cause mortality is inconclusive 11 106 Cancer Edit There is insufficient evidence that supplementation with omega 3 fatty acids has an effect on different cancers 1 9 41 107 Omega 3 supplements do not improve body weight muscle maintenance or quality of life in cancer patients 108 Cardiovascular disease Edit Moderate and high quality evidence from a 2020 review showed that EPA and DHA such as that found in omega 3 polyunsaturated fatty acid supplements does not appear to improve mortality or cardiovascular health 8 There is weak evidence indicating that a linolenic acid may be associated with a small reduction in the risk of a cardiovascular event or the risk of arrhythmia 2 8 A 2018 meta analysis found no support that daily intake of one gram of omega 3 fatty acid in individuals with a history of coronary heart disease prevents fatal coronary heart disease nonfatal myocardial infarction or any other vascular event 11 However omega 3 fatty acid supplementation greater than one gram daily for at least a year may be protective against cardiac death sudden death and myocardial infarction in people who have a history of cardiovascular disease 109 No protective effect against the development of stroke or all cause mortality was seen in this population 109 Fish oil supplementation has not been shown to benefit revascularization or abnormal heart rhythms and has no effect on heart failure hospital admission rates 110 Furthermore fish oil supplement studies have failed to support claims of preventing heart attacks or strokes 12 In the EU a review by the European Medicines Agency of omega 3 fatty acid medicines containing a combination of an ethyl ester of eicosapentaenoic acid and docosahexaenoic acid at a dose of 1 g per day concluded that these medicines are not effective in secondary prevention of heart problems in patients who have had a myocardial infarction 111 Evidence suggests that omega 3 fatty acids modestly lower blood pressure systolic and diastolic in people with hypertension and in people with normal blood pressure 112 113 Omega 3 fatty acids can also reduce heart rate 114 an emerging risk factor Some evidence suggests that people with certain circulatory problems such as varicose veins may benefit from the consumption of EPA and DHA which may stimulate blood circulation and increase the breakdown of fibrin a protein involved in blood clotting and scar formation Omega 3 fatty acids reduce blood triglyceride levels but do not significantly change the level of LDL cholesterol or HDL cholesterol 115 116 The American Heart Association position 2011 is that borderline elevated triglycerides defined as 150 199 mg dL can be lowered by 0 5 1 0 grams of EPA and DHA per day high triglycerides 200 499 mg dL benefit from 1 2 g day and gt 500 mg dL be treated under a physician s supervision with 2 4 g day using a prescription product 117 In this population omega 3 fatty acid supplementation decreases the risk of heart disease by about 25 118 A 2019 review found that omega 3 fatty acid supplements make little or no difference to cardiovascular mortality and that patients with myocardial infarction yield no benefit in taking the supplements 119 A 2021 review found that omega 3 supplementation did not affect cardiovascular disease outcomes 10 A 2021 meta analysis showed that use of marine omega 3 supplementation was associated with an increased risk of atrial fibrillation with the risk appearing to increase for doses greater than one gram per day 120 Chronic kidney disease Edit In people with chronic kidney disease CKD who require hemodialysis there is a risk that vascular blockage due to clotting may prevent dialysis therapy from being possible Omega 3 fatty acids contribute to the production of eicosanoid molecules that reduce clotting However a Cochrane review in 2018 did not find clear evidence that omega 3 supplementation has any impact on the prevention of vascular blockage in people with CKD 121 There was also moderate certainty that supplementation did not prevent hospitalisation or death within a 12 month period 121 Stroke Edit A 2022 Cochrane review of controlled trials did not find clear evidence that marine derived omega 3 supplementation improves cognitive and physical recovery or social and emotional wellbeing following stroke diagnosis nor prevents stroke recurrence and mortality 13 In this review mood appeared to worsen slightly among those receiving 3g fish oil supplementation for 12 weeks psychometric scores changed by 1 41 0 07 to 2 75 points less than those receiving palm and soy oil 13 However this represented only a single small study and was not observed in a study lasting more than 3 months Overall the review was limited by the low number of high quality evidence available Inflammation Edit A 2013 systematic review found tentative evidence of benefit for lowering inflammation levels in healthy adults and in people with one or more biomarkers of metabolic syndrome 122 Consumption of omega 3 fatty acids from marine sources lowers blood markers of inflammation such as C reactive protein interleukin 6 and TNF alpha 123 124 125 For rheumatoid arthritis one systematic review found consistent but modest evidence for the effect of 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 126 The American College of Rheumatology has stated that there may be modest benefit from the 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 127 The National Center for Complementary and Integrative Health has concluded that supplements containing omega 3 fatty acids may help relieve rheumatoid arthritis symptoms but warns that such supplements may interact with drugs that affect blood clotting 128 Developmental disabilities Edit One meta analysis concluded that omega 3 fatty acid supplementation demonstrated a modest effect for improving ADHD symptoms 129 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 130 while a different review found insufficient evidence to draw any conclusion about the use of PUFAs for children with specific learning disorders 131 Another review concluded that the evidence is inconclusive for the use of omega 3 fatty acids in behavior and non neurodegenerative neuropsychiatric disorders such as ADHD and depression 132 A 2015 meta analysis of the effect of omega 3 supplementation during pregnancy did not demonstrate a decrease in the rate of preterm birth or improve outcomes in women with singleton pregnancies with no prior preterm births 133 A 2018 Cochrane systematic review with moderate to high quality of evidence suggested that omega 3 fatty acids may reduce risk of perinatal death risk of low body weight babies and possibly mildly increased LGA babies 134 A 2021 umbrella review with moderate to high quality of evidence suggested that omega 3 supplementation during pregnancy can exert favorable effects against pre eclampsia low birth weight pre term delivery and post partum depression and can improve anthropometric measures immune system and visual activity in infants and cardiometabolic risk factors in pregnant mothers 135 Mental health Edit Omega 3 supplementation has not been shown to significantly affect symptoms of anxiety major depressive disorder or schizophrenia 136 137 A 2021 Cochrane review concluded that there is not sufficient high certainty evidence to determine the effects of n 3PUFAs as a treatment for MDD 138 Omega 3 fatty acids have also been investigated as an add on for the treatment of depression associated with bipolar disorder although there is limited data available 139 Two reviews have suggested that omega 3 fatty acid supplementation significantly improves depressive symptoms in perinatal women 135 140 In contrast to dietary supplementation studies there is significant difficulty in interpreting the literature regarding dietary intake of omega 3 fatty acids e g from fish due to participant recall and systematic differences in diets 141 There is also controversy as to the efficacy of omega 3 with many meta analysis papers finding heterogeneity among results which can be explained mostly by publication bias 142 143 A significant correlation between shorter treatment trials was associated with increased omega 3 efficacy for treating depressed symptoms further implicating bias in publication 143 Cognitive aging Edit A 2016 Cochrane review found no convincing evidence for the use of omega 3 PUFA supplements in treatment of Alzheimer s disease or dementia 144 There is preliminary evidence of effect on mild cognitive problems but none supporting an effect in healthy people or those with dementia 145 146 A 2020 review suggested that omega 3 supplementation has no effect on global cognitive function but has a mild benefit in improving memory in non demented adults 147 A 2022 review found promising evidence for prevention of cognitive decline in people who regularly eat long chain omega 3 rich foods Conversely clinical trials with participants already diagnosed with Alzheimer s show no effect 148 Brain and visual functions Edit Brain function and vision rely on dietary intake of DHA to support a broad range of cell membrane properties particularly in grey matter which is rich in membranes 149 150 A major structural component of the mammalian brain DHA is the most abundant omega 3 fatty acid in the brain 151 152 Omega 3 PUFA supplementation has no effect on macular degeneration or development of visual loss 153 Atopic diseases Edit Results of studies investigating the role of LCPUFA supplementation and LCPUFA status in the prevention and therapy of atopic diseases allergic rhinoconjunctivitis atopic dermatitis and allergic asthma are controversial therefore as of 2013 update it could not be stated either that the nutritional intake of n 3 fatty acids has a clear preventive or therapeutic role or that the intake of n 6 fatty acids has a promoting role in the context of atopic diseases 154 Phenylketonuria and omega 3 intake Edit People with PKU often have low intake of omega 3 fatty acids because nutrients rich in omega 3 fatty acids are excluded from their diet due to high protein content 155 Asthma Edit As of 2015 there was no evidence that taking omega 3 supplements can prevent asthma attacks in children 156 Diabetes Edit A 2019 review found that omega 3 supplements have no effect on prevention and treatment of type 2 diabetes 157 158 See also Edit Biology portal Medicine portalEssential fatty acid interactions Essential nutrients Inflammation Olive oil regulation and adulteration Omega 6 fatty acid Omega 7 fatty acid Omega 9 fatty acid Ratio of fatty acids in different foods Reinforced lipidsReferences Edit a b c d e f g Omega 3 Fatty Acids Office of Dietary Supplements US National Institutes of Health 26 March 2021 Retrieved 10 June 2021 a b c d e f g Essential Fatty Acids Micronutrient Information Center Linus Pauling Institute Oregon State University 1 May 2019 Retrieved 10 June 2021 Scorletti E Byrne CD 2013 Omega 3 fatty acids hepatic lipid metabolism and nonalcoholic fatty liver disease Annual Review of Nutrition 33 1 231 248 doi 10 1146 annurev nutr 071812 161230 PMID 23862644 Jacobsen C Nielsen NS Horn AF Sorensen AD 31 July 2013 Food Enrichment with 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commentary on the article by Isaacs et al on page 308 Pediatric Research 63 3 229 231 doi 10 1203 pdr 0b013e318168c6d1 PMID 18287959 S2CID 6564743 Horrocks LA Yeo YK September 1999 Health benefits of docosahexaenoic acid DHA Pharmacological Research 40 3 211 225 doi 10 1006 phrs 1999 0495 PMID 10479465 Lawrenson JG Evans JR April 2015 Omega 3 fatty acids for preventing or slowing the progression of age related macular degeneration The Cochrane Database of Systematic Reviews 2015 4 CD010015 doi 10 1002 14651858 CD010015 pub3 PMC 7087473 PMID 25856365 Lohner S Decsi T Role of Long Chain Polyunsaturated Fatty Acids in the Prevention and Treatment of Atopic Diseases In Polyunsaturated Fatty Acids Sources Antioxidant Properties and Health Benefits edited by Angel Catala NOVA Publishers 2013 Chapter 11 pp 1 24 ISBN 978 1 62948 151 7 Lohner S Fekete K Decsi T July 2013 Lower n 3 long chain polyunsaturated fatty acid values in patients with phenylketonuria a systematic review and meta analysis Nutrition Research 33 7 513 20 doi 10 1016 j nutres 2013 05 003 PMID 23827125 Muley P Shah M Muley A 2015 Omega 3 Fatty Acids Supplementation in Children to Prevent Asthma Is It Worthy A Systematic Review and Meta Analysis Journal of Allergy 2015 312052 doi 10 1155 2015 312052 PMC 4556859 PMID 26357518 Brown TJ Brainard J Song F Wang X Abdelhamid A Hooper L 2019 Omega 3 omega 6 and total dietary polyunsaturated fat for prevention and treatment of type 2 diabetes mellitus systematic review and meta analysis of randomised controlled trials BMJ 366 l4697 doi 10 1136 bmj l4697 PMC 6699594 PMID 31434641 Boosting omega 3 fatty acid intake is unlikely to prevent type 2 diabetes NIHR Evidence Plain English summary 2019 11 12 doi 10 3310 signal 000833 S2CID 242640723 Further reading EditAllport S September 2006 The Queen of Fats Why Omega 3s Were Removed from the Western Diet and What We Can Do to Replace Them University of California Press ISBN 978 0 520 24282 1 OCLC 801139991 Chow CK 2001 Fatty Acids in Foods and Their Health Implications New York Routledge Publishing OCLC 25508943 Clover C 2004 The End of the Line How overfishing is changing the world and what we eat London Ebury Press ISBN 0 09 189780 7 OCLC 67383509 Greenberg P 2018 The Omega Principle Seafood and the Quest for a Long Life and a Healthier Planet New York Penguin Press ISBN 9781594206344 OCLC 1007552654 Stoll AL 2001 The Omega 3 Connection how you can restore your body s natural balance and treat depression Simon amp Schuster ISBN 0 684 87138 6 OCLC 670441405 External links Edit Media related to Omega 3 fatty acids at Wikimedia Commons Retrieved from https en wikipedia org w index php title Omega 3 fatty acid amp oldid 1171215878, wikipedia, wiki, book, books, library,

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