Essential Fatty Acids (EFAs)

Essential Fatty Acids (EFAs) are necessary fats that humans cannot synthesize, and must be obtained
through diet. EFAs are long-chain polyunsaturated fatty acids derived from linolenic, linoleic, and oleic acids. here are t!o families of EFAs" #mega-$ and #mega-%. #mega-& is necessary yet 'non-essential' because the body can manufacture a modest amount on its o!n, provided essential EFAs are present. he number follo!ing '#mega-' represents the position of the first double bond, counting from the terminal methyl group on the molecule. #mega-$ fatty acids are derived from (inolenic Acid, #mega-% from (inoleic Acid, and #mega-& from #leic Acid. EFAs support the cardiovascular, reproductive, immune, and nervous systems. he human body needs EFAs to manufacture and repair cell membranes, enabling the cells to obtain optimum nutrition and e)pel harmful !aste products. A primary function of EFAs is the production of prostaglandins, !hich regulate body functions such as heart rate, blood pressure, blood clotting, fertility, conception, and play a role in immune function by regulating inflammation and encouraging the body to fight infection. Essential Fatty Acids are also needed for proper gro!th in children, particularly for neural development and maturation of sensory systems, !ith male children having higher needs than females. Fetuses and breast-fed infants also re*uire an ade*uate supply of EFAs through the mother+s dietary inta,e. EFA deficiency is common in the -nited .tates, particularly #mega-$ deficiency. An ideal inta,e ratio of #mega-% to #mega-$ fatty acids is bet!een /"/ and 0"/, !ith most Americans only obtaining a ratio bet!een /1"/ and 23"/. he minimum healthy inta,e for both linolenic (#mega-$) and linoleic (#mega-%) acid via diet, per adult per day, is /.3 grams of each. #ne tablespoon of fla)seed oil can provide this amount, or larger amounts of other linolenic-rich foods. 4ecause high heat destroys linolenic acid, coo,ing in linolenic-rich oils or eating coo,ed linolenic-rich fish is unli,ely to provide a sufficient amount. EFA deficiency and #mega %5$ imbalance is lin,ed !ith serious health conditions, such as heart attac,s, cancer, insulin resistance, asthma, lupus, schizophrenia, depression, postpartum depression, accelerated aging, stro,e, obesity, diabetes, arthritis, A676, and Alzheimer+s 6isease, among others.

#mega-$ ((inolenic Acid)

Alpha (inolenic Acid (A(A) is the principal #mega-$ fatty acid, !hich a healthy human !ill convert into
eicosapentaenoic acid (E8A), and later into docosahe)aenoic acid (67A). E8A and the 9(A synthesized from linoleic (#mega-%) acid are later converted into hormone-li,e compounds ,no!n as eicosanoids, !hich aid in many bodily functions including vital organ function and intracellular activity. #mega-$s are used in the formation of cell !alls, ma,ing them supple and fle)ible, and improving circulation and o)ygen upta,e !ith proper red blood cell fle)ibility and function. #mega-$ deficiencies are lin,ed to decreased memory and mental abilities, tingling sensation of the nerves, poor vision, increased tendency to form blood clots, diminished immune function, increased triglycerides and 'bad' cholesterol ((6() levels, impaired membrane function, hypertension, irregular heart beat, learning disorders, menopausal discomfort, itchiness on the front of the lo!er leg(s), and gro!th retardation in infants, children, and pregnant !omen.

Found in foods:
Fla)seed oil (fla)seed oil has the
highest linolenic content of any food), fla)seeds, fla)seed meal, hempseed oil, hempseeds, !alnuts, pump,in seeds, 4razil nuts, sesame seeds, avocados, some dar, leafy green vegetables (,ale, spinach, purslane, mustard greens, collards, etc.), canola oil (cold-pressed and unrefined), soybean oil, !heat germ oil, salmon, mac,erel, sardines, anchovies, albacore tuna, and others. #ne tablespoon per day of fla)seed oil should provide the recommended daily adult portion of linolenic acid, although 'time-

released' effects of consuming nuts and other linolenic-rich foods is being studied, and considered more beneficial than a once-daily oil inta,e. Fla)seed oil used for dietary supplementation should be ,ept in the refrigerator or freezer, and purchased from a supplier !ho refrigerates the li*uid as !ell. :anola oil is often used as a cheaper alternative to the healthier virgin olive and grapeseed oils. Although :anola has at least some linolenic content, supermar,et varieties of canola oil are often refined and processed !ith chemicals and heat, !hich destroy much of its linolenic acid. :old-pressed, unrefined :anola oil is a healthier type of :anola (sometimes pricier than virgin olive oil), and found primarily in health food stores and specialty mar,ets. he !ord 'canola' is derived from ':anadian oil', as :anola !as developed in :anada from the rape plant. ;ape is a plant in the mustard family, and its rapeseed oil has at times been illegally blended !ith olive oil, particularly in Europe, to cheapen olive oil production costs. Although rapeseed oil is high in linolenic acid, it can ma,e humans seriously ill if enough is consumed, and olive oil cheapened !ith rapeseed oil has a history of severely sic,ening its consumers. (Every feel itchy after eating commercial brands of peanut butter< :hec, the label -- it probably contains rapeseed oil.) :anola !as developed to eliminate chemicals to)ic to humans in rapeseed oil, thus creating an ine)pensive oil !ith linolenic acid. -nli,e olive and fla)seed oil, both ,no!n to the ancients and used as man,ind evolved, :anola is a recent oil, and its long-term effects on humans are not yet ,no!n. -nripe fla)seeds contain a natural form of cyanide, and home gardeners should be cautious if trying to gro! fla). he seeds must be ripe before harvesting. =f attempting to gro! fla) at home, consult an e)perienced gro!er.

#mega-% ((inoleic Acid)

(inoleic Acid is the primary #mega-% fatty acid. A healthy human !ith
good nutrition !ill convert linoleic acid into gamma linolenic acid (9(A), !hich !ill later by synthesized, !ith E8A from the #mega-$ group, into eicosanoids. .ome #mega-%s improve diabetic neuropathy, rheumatoid arthritis, 8>., s,in disorders (e.g. psoriasis and eczema), and aid in cancer treatment. Although most Americans obtain an e)cess of linoleic acid, often it is not converted to 9(A because of metabolic problems caused by diets rich in sugar, alcohol, or trans fats from processed foods, as !ell as smo,ing, pollution, stress, aging, viral infections, and other illnesses such as diabetes. =t is best to eliminate these factors !hen possible, but some prefer to supplement !ith 9(A-rich foods such as borage oil, blac, currant seed oil, or evening primrose oil.

Found in foods:
Fla)seed oil, fla)seeds, fla)seed meal, hempseed oil, hempseeds,
grapeseed oil, pump,in seeds, pine nuts, pistachio nuts, sunflo!er seeds (ra!), olive oil, olives, borage oil, evening primrose oil, blac, currant seed oil, chestnut oil, chic,en, among many others. Avoid refined and hydrogenated versions of these foods. :orn, safflo!er, sunflo!er, soybean, and cottonseed oils are also sources of linoleic acid, but are refined and may be nutrient-deficient as sold in stores.

#mega-& (#leic Acid)

Essential but technically not an EFA, because the human body can manufacture a limited amount, provided
essential EFAs are present. >onounsaturated oleic acid lo!ers heart attac, ris, and arteriosclerosis, and aids in cancer prevention.

Found in foods:
#live oil (e)tra virgin or virgin), olives, avocados, almonds, peanuts, sesame oil, pecans, pistachio nuts,
cashe!s, hazelnuts, macadamia nuts, etc. #ne to t!o tablespoons of e)tra virgin or virgin olive oil per day should provide sufficient oleic acid for adults. 7o!ever, the 'time-released' effects of obtaining these nutrients from nuts and other !hole foods is thought to be more beneficial than consuming the entire daily amount via a single oil dose.

Food tips
7igh heat, light, and o)ygen destroy EFAs, so !hen consuming foods for their EFA content, try to avoid
coo,ed or heated forms. For e)ample, ra! nuts are a better source than roasted nuts. 6on+t use fla)seed oil for coo,ing, and never re-use any type of oil. ;eplace hydrogenated fats (li,e margarine), cholesterol-based fats (butter5dairy products), and polysaturated fats (common coo,ing oils) !ith healthy EFA-based fats !hen possible. For e)ample, instead of margarine or butter on your !arm (not hot) vegetables, use fla)seed and5or e)tra virgin olive oils !ith salt. ( his tastes similar to margarine, as margarine is ?ust hydrogenated oil !ith salt.) .prin,ling fla)seed meal on vegetables adds a slightly nutty taste. @hole fla)seeds are usually passed through the intestine, absorbing !ater only and not yielding much oil. Also, it+s best not to use huge amounts of fla)seed in its meal (ground seed) form, as it contains phytoestrogens. he oil is much lo!er in phytoestrogens. =n many recipes calling for vegetable shortening, replacing the shortening !ith half as much virgin olive oil, and a very small pinch of e)tra salt, often yields similar results. Adding fla)seed and5or virgin olive oil to salads instead of supermar,et salad oil is another healthy change. ;eplace oily snac, foods, li,e potato chips and corn chips, !ith nuts and seeds. E)tra virgin olive oil or grapeseed oil are best to use for coo,ing oil, as they !ithstand high heat !ell.

The human body can manufacture most of the fats it needs, including cholesterol, saturated fatty acids and unsaturated fatty acids. But there are two fatty acids which cannot be manufactured in the body, and which must be obtained from dietary sources: linoleic acid and alpha-linolenic acid. These are the essential fatty acids. Linoleic acid is an 18-carbon chain with 2 double-bonds, whereas alpha-linolenic acid is an 18-carbon chain with double-bonds. The position of double-bonds in a fatty acid is critical to function, and this is especially true of double-bonds close to the methyl end. !or long-chain fatty acids, the body"s en#ymes cannot add double-bonds near the methyl end.

Two distinct families of essential fatty acids e$ist in the human body: the omega% family and omega%& family. The omega3 family comes from alpha-linolenic acid, and the omega6 family comes from linoleic acid. 'ach family is the result of increasing chain length and of forming double-bonds from one of these two essential fatty acids. The two families compete for the same en#ymes for forming double bonds (desaturase en#ymes) and en#ymes for lengthening the carbon chain (elongase en#ymes). 'longase en#ymes always add carbon atoms (in pairs) to the delta end of the fatty acid.

Another important product of linoleic acid is arachidonic acid. Arachidonic acid is a 21carbon omegaA% fatty acid !ith 0 double-bonds. Arachidonic acid, in turn, gives rise to a

!hole group of 21-carbon, biologically-important substances ,no!n as the eicosanoids (eicosa- is 9ree, for '21'), including prostaglandins, thrombo)anes, lipo)ins and leu,otrienes B !hich affect immunity, inflammation and blood clotting (among other actions). 4ut omegaA$ fatty acids can also produce eicosanoids. Cote!orthy members of the omegaA$ family of fatty acids manufactured from alphalinolenic acid are EicosaPentaenoic Acid (EPA) and DocasaHexaenoic Acid (DHA). A pentaenoic acid has 3 double-bonds. A he)aenoic acid has % double-bonds. E8A is a 21carbon chain fatty acid, !hereas 67A is a 22-carbon chain fatty acid. (i,e arachidonic acid, E8A gives rise to its o!n class of eicosanoids. he E8A-generated eicosanoids are in the omegaA$ family, as distinct from the omegaA% eicosanoids derived from arachidonic acid.

IV. ESSENTIAL FATTY ACIDS IN THE DIET

he primary source of omegaA% fatty acids in the diet is ino eic acid from the oils of seeds and grains. .unflo!er, safflo!er and corn oil are particularly rich sources of ino eic acid, !hich is at the root of the omegaA% fatty-acid family. Evening primrose oil and borage oil are high not only in linoleic acid, but the omegaA% derivative gamma-linolenic acid (9(A). Avocado is /3-21D oil B mainly monosaturated, but also high in linoleic acid. (Avocado has the highest fat content and the highest fiber content B soluble as !ell as insoluble B of any fruit.) A !ha- ino enic acid, the primary dietary source of omegaA$ fatty acids in the diet, is fre*uently found in green leaves. he leaves and seeds of the perilla plant (!idely eaten in Eapan, Forea and =ndia) are the richest plant source of alpha-linolenic acid, although linseed oil is also a rich source. Fish oil contains very little alpha-linolenic acid, but is rich in the omegaA$ derivatives E8A and 67A. Fish are at the top of a food chain based on phytoplan,ton (algae) that manufacture large amounts of E8A and 67A. Conetheless, fish can be high in to)ic methylmercury. (For more information, see my essay =s >ercury in Fish a 7ealth 7azard<) =t has been estimated that thousands of years ago the diet of human hunter-gatherers consisted of appro)imately e*ual parts of omegaA$ and omegaA% essential fatty acids GH/3I. .ince the beginning of agriculture ten thousand years ago there has been a steady increase in omegaA% at the e)pense of omegaA$ fat in the human diet. his process accelerated about 31 years ago as cattle began to be fed increasingly on grains rather than grass. ;ecommendations by nutritionists to eat margarine rather than butter (polyunsaturated rather than saturated fats) increased the trend to!ard omegaA% and trans fat consumption. :urrently, the ratio of omegaA% to omegaA$ fatty acids in the American diet is JAtoA/ or more. here are good reasons to believe that this imbalanced essential fatty acid ratio has led to increased cancer, heart disease, allergies, diabetes and other afflictions. >uch of the reason for this lies in the membranes of our cells.

*igh fat diets are well-+nown to be associated with certain +inds of cancers, including breast cancer, in particular ,- 1.. /lthough butterfat stimulates breast cancer when compared with a fat-free diet, safflower oil margarine (linoleic acid, an omega%&) has been shown to induce breast cancer much more strongly ,-&.. Linoleic acid is the fat that most fre0uently is associated with cancer, whereas omega% fatty acids li+e 1*/ and perilla-oil suppress cancer ,- 2,- .. 2t has been theori#ed that linoleic acid causes cancer by chronic o3erproduction of the inflammatory arachidonic acid eicosanoids, which stimulate the proliferation of mutated cells ,-&.. 4mega% fatty acids reduce cancer ris+ by mar+edly inhibiting /cti3ator 5rotein 1 (AP1), a transcription factor which promotes cancerous proliferation and metastasis. 4mega%& fatty acids promote cancer by bloc+ing omega% acti3ity

The biological effects of the -3 and -6 fatty acids are mediated by their mutual interactions, see Essential fatty acid interactions for detail.

=n the body, essential fatty acids serve multiple functions. =n each of these, the balance bet!een dietary K-$ and K-% strongly affects function.

hey are modified to ma,e o the classic eicosanoids (affecting inflammation and many other cellular functions)
o o

the endocannabinoids (affecting mood, behavior and inflammation) the lipo)ins from K-% EFAs and resolvins from K-$ (in the presence of aspirin, do!nregulating inflammation.) the isofurans, neurofurans, isoprostanes, hepo)ilins, epo)yeicosatrienoic acids (EE s) and Ceuroprotectin 6

hey form lipid rafts (affecting cellular signaling)G$I hey act on 6CA (activating or inhibiting transcription factors such as CFL4, !hich is lin,ed to pro-inflammatory cyto,ine production

he essential fatty acids start !ith the short chain !o "#nsat#rated $att" acids (SC-P%FA)"

K-$ fatty acids" o M-(inolenic acid or A(A (/N"$) K-% fatty acids"
o

(inoleic acid or (A (/N"2)

hese t!o fatty acids cannot be synthesised by humans, as humans lac, the desaturase enzymes re*uired for their production. hey form the starting point for the creation of longer and more desaturated fatty acids, !hich are also referred to as on&-chain !o "#nsat#rated $att" acids (LC-P%FA)"

K-$ fatty acids" o eicosapentaenoic acid or E8A (21"3)

o

docosahe)aenoic acid or 67A (22"%)

K-% fatty acids"

o o o

gamma-linolenic acid or 9(A (/N"$) dihomo-gamma-linolenic acid or 69(A (21"$) arachidonic acid or AA (21"0)

K-& fatty acids are not essential in humans, because humans generally possess all the enzymes re*uired for their synthesis. E)ceptions do occur in older people or people !ith a

liver problem that do not completely produce a sufficient amount,Gcitation neededI and hence many supplement companies mar,et #mega $-%-& blends.