Arachidonic acid: Difference between revisions

| verifiedrevid = 457136995

| ImageFile_Ref = {{Chemboximage|correct|??}}

| ImageSize = 200

| ImageName = Structural formula of arachidonic acid

| IUPACName = (5''Z'',8''Z'',11''Z'',14''Z'')-5,8,11,14-Eicosatetraenoic acid

| SystematicName = (5''Z'',8''Z'',11''Z'',14''Z'')-Icosa-5,8,11,14-tetraenoic acid<ref>http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=231</ref>

| OtherNames = 5,8,11,14-all-''cis''-Eicosatetraenoic acid; all-''cis''-5,8,11,14-Eicosatetraenoic acid; Arachidonate

| Section1 = {{Chembox Identifiers

| InChI = 1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 444899

| PubChem_Ref = {{Pubchemcite|correct|PubChem}}

| ChemSpiderID = 392692

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII = 27YG812J1I

| UNII_Ref = {{fdacite|correct|FDA}}

| EINECS = 208-033-4

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = <!-- blanked - oldvalue: DB04557 -->

| KEGG = <!-- blanked - oldvalue: C00219 -->

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = Arachidonic+acid

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 15594

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = CE6675000

| Beilstein = 1713889

| 3DMet = B00061

| SMILES = CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O

| StdInChI = 1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YZXBAPSDXZZRGB-DOFZRALJSA-N

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| Section2 = {{Chembox Properties

| C = 20

| H = 32

| O = 2

| ExactMass = 304.240230268 g mol^-1

| Density = 0.922 g/cm³

| MeltingPtC = -49

| BoilingPtCL = 169

| BoilingPtCH = 171

| Boiling_notes = at 0.15 mmHg

| LogP = 6.994

| pKa = 4.752

| Section3 = {{Chembox Hazards

| RPhrases = {{R19}}

| NFPA-H = 1

| NFPA-F = 1

| NFPA-R = 0

| FlashPt = {{convert|113|C|F}}

'''Arachidonic acid''' (AA, sometimes ARA) is a [[polyunsaturated]] [[omega-6 fatty acid]] 20:4(ω-6).

It is the counterpart to the saturated [[arachidic acid]] found in [[peanut]] oil, (''L. arachis &ndash; peanut''.)<ref name=Dorland>{{cite web|

title = Dorland's Medical Dictionary &ndash; 'A'

| url= http://www.mercksource.com/pp/us/cns/cns_hl_dorlands.jspzQzpgzEzzSzppdocszSzuszSzcommonzSzdorlandszSzdorlandzSzdmd_a_56zPzhtm

| accessdate = 2007-01-12}}</ref>

[[File:AAnumbering.png|420px]]

In [[chemical structure]], arachidonic acid is a [[carboxylic acid]] with a 20-carbon chain and four ''[[cis]]''-[[double bonds]]; the first double bond is located at the sixth carbon from the omega end.

Some chemistry sources define 'arachidonic acid' to designate any of the [[eicosatetraenoic acid]]s. However, almost all writings in biology, medicine and nutrition limit the term to all-''cis''-5,8,11,14-eicosatetraenoic acid.

Arachidonic acid is a polyunsaturated fatty acid that is present in the [[phospholipid]]s (especially [[phosphatidylethanolamine]], [[phosphatidylcholine]] and [[phosphatidylinositide]]s) of [[cell membrane|membrane]]s of the body's [[cell (biology)|cell]]s, and is abundant in the [[brain]], [[muscles]], [[liver]].

In addition to being involved in [[cellular signaling]] as a lipid [[second messenger]] involved in the regulation of signaling enzymes, such as [[Phospholipase C|PLC]]-γ, PLC-δ and [[Protein kinase C|PKC]]-α, -β and -γ isoforms, arachidonic acid is a key inflammatory intermediate and can also act as a [[vasodilator]].<ref name=Dominiczak>{{cite book |last= Baynes |first= John W. |coauthors= Marek H. Dominiczak |title= Medical Biochemistry 2nd. Edition |publisher= [[Elsevier| Elsevier Mosby]] |year= 2005 |page= 555 |isbn= 0723433410}}</ref> (Note separate synthetic pathways, as described in section below)

==Essential fatty acid==

{{Main|Essential fatty acid#Essentiality}}

[[Image:Steaks.jpg|thumb|right|250px|Arachidonic acid in the human body usually comes from dietary animal sources&mdash;meat, eggs, dairy&mdash;or is synthesized from linoleic acid.]]

Arachidonic acid is not one of the [[essential fatty acid]]s. However it does become essential if there is a deficiency in [[linoleic acid]] or if there is an inability to convert linoleic acid to arachidonic acid which is required by most [[mammal]]s. Some mammals lack the ability to&mdash;or have a very limited capacity to&mdash;convert linoleic acid into arachidonic acid, making it an essential part of their diet. Since little or no arachidonic acid is found in common plants, such animals are obligate [[carnivore]]s; the cat is a common example.<ref name=carnivore>{{cite journal |last1=MacDonald |first1=ML |last2=Rogers |first2=QR |last3=Morris |first3=JG |title=Nutrition of the Domestic Cat, a Mammalian Carnivore |journal=Annual Review of Nutrition |volume=4 |pages=521–62 |year=1984 |pmid=6380542 |doi=10.1146/annurev.nu.04.070184.002513}}</ref><ref name=Sinclair>{{cite journal |last1=Rivers |first1=JP |last2=Sinclair |first2=AJ |last3=Craqford |first3=MA |title=Inability of the cat to desaturate essential fatty acids |doi=10.1038/258171a0 |journal=Nature |pmid=1186900 |year=1975 |volume=258 |issue=5531 |pages=171–3|bibcode = 1975Natur.258..171R }}</ref> A commercial source of arachidonic acid has been derived, however, from the fungus ''[[Mortierella alpina]]''.<ref>[http://www.martek.com/About/History.aspx History of Martek], Martek.com</ref>

==Synthesis and cascade==

[[Image:Eicosanoid synthesis.svg|thumb|320px|Eicosanoid synthesis.]]

Arachidonic acid is freed from a [[phospholipid]] molecule by the enzyme [[phospholipase A2]] (PLA₂), which cleaves off the [[fatty acid]], but can also be generated from [[diacylglycerol|DAG]] by [[diacylglycerol lipase]].<ref name=Dominiczak/>

Arachidonic acid generated for signaling purposes appears to be derived by the action of a phosphatidylcholine-specific cytosolic [[phospholipase A2]] (cPLA₂, 85 kDa), whereas inflammatory arachidonic acid is generated by the action of a low-molecular-weight secretory PLA₂ (sPLA₂, 14-18 kDa).<ref name=Dominiczak/>

Arachidonic acid is a precursor in the production of [[eicosanoid]]s:

* The enzymes [[cyclooxygenase]] and [[peroxidase]] lead to [[prostaglandin H2]], which in turn is used to produce the [[prostaglandin]]s, [[prostacyclin]], and [[thromboxane]]s.

* The enzyme [[5-lipoxygenase]] leads to [[5-HPETE]], which in turn is used to produce the [[leukotriene]]s.

* Arachidonic acid is also used in the biosynthesis of [[anandamide]].

* Some arachidonic acid is converted into [[hydroxyeicosatetraenoic acid]]s (HETEs) and [[epoxyeicosatrienoic acid]]s (EETs) by [[epoxygenase]].<ref name=boron108>{{cite book |author=Walter F., PhD. Boron |title=Medical Physiology: A Cellular And Molecular Approaoch |publisher=Elsevier/Saunders |location= |year=2003 |page=108 |isbn=1-4160-2328-3}}</ref>

The production of these derivatives and their action in the body are collectively known as the ''arachidonic acid cascade''; see [[essential fatty acid interactions]] for more details.

{{See|Phospholipase_A2#Regulation}}

*[[5-HT2 receptor]]s <ref name=boron103>{{cite book |author=Walter F., PhD. Boron |title=Medical Physiology: A Cellular And Molecular Approaoch |publisher=Elsevier/Saunders |location= |year=2003 |page=103 |isbn=1-4160-2328-3}}</ref>

*[[Metabotropic glutamate receptor 1|mGLUR1]]<ref name=boron103/>

*[[Basic fibroblast growth factor|bFGF]] receptor<ref name=boron103/>

*[[Interferon-alpha receptor|INF-α receptor]]<ref name=boron103/>

*[[Interferon-gamma receptor|INF-γ receptor]]<ref name=boron103/>

{{See|Phospholipase C#Activation}}

Alternatively, arachidonic acid may be cleaved from phospholipids by [[phospholipase C]] (PLC), yielding [[diacylglycerol]] (DAG), which subsequently is cleaved by [[Diacylglycerol lipase|DAG lipase]] to yield arachidonic acid.<ref name=boron103/>

*[[Adenosine A1 receptor|A1 receptor]]<ref name=boron104>{{cite book |author=Walter F., PhD. Boron |title=Medical Physiology: A Cellular And Molecular Approaoch |publisher=Elsevier/Saunders |location= |year=2003 |pages=104 |isbn=1-4160-2328-3}}</ref>

*[[Dopamine receptor D2|D2 receptor]]<ref name=boron104/>

*[[Alpha-2 adrenergic receptor|α-2 adrenergic receptor]]<ref name=boron104/>

*[[5-HT1 receptor]]<ref name=boron104/>

==Arachidonic acid in the body==

===Muscle growth===

Through its conversion to active components such as the prostaglandin PGF2alpha, arachidonic acid is necessary for the repair and growth of skeletal muscle tissue.<ref>{{cite journal |doi=10.1210/jc.86.10.5067 |last1=Trappe |first1=TA |last2=Fluckey |first2=JD |last3=White |first3=F |last4=Lambert |first4=CP |last5=Evans |first5=WJ |title=Skeletal muscle PGF(2)(alpha) and PGE(2) in response to eccentric resistance exercise: influence of ibuprofen acetaminophen. |journal=The Journal of clinical endocrinology and metabolism |volume=86 |pmid=11600586 |issue=10 |pages=5067–70 |year=2001}}</ref> This role makes ARA an important dietary component in support of the muscle anabolic process. One of the lead researchers of the Baylor study (see Bodybuilding section) on arachidonic acid, Mike Roberts MS, CSCS, has authored an article published under the title ''Arachidonic Acid, The New Mass Builder'' explaining the role of this nutrient in muscle anabolism, and its potential for the enhancement of muscle size and strength.<ref>http://www.bodybuilding.com/fun/llewellyn2.htm</ref> The paper explains that for optimal muscle growth a training stimulus must elicit localized inflammation and soreness. It explains that arachidonic acid (AA, 20:4n-6) is an essential Omega-6 (1-6) polyunsaturated fatty acid that is abundant in skeletal muscle membrane phospholipids (figure 2). It is also the body's principal building block for the production of prostaglandins, which are known to have various physiological roles including a close involvement in inflammation. Also, the prostaglandin isomer PGF2a has a potent ability to stimulate muscle growth. As such, arachidonic acid is a regulator of localized muscle inflammation, and may be a central nutrient controlling the intensity of the anabolic/tissue-rebuilding response to weight training.

Arachidonic acid is one of the most abundant fatty acids in the brain, and is present in similar quantities to DHA ([[docosahexaenoic acid]]). The two account for approximately 20% of its fatty acid content.<ref>{{cite journal |last1=Crawford |first1=MA |last2=Sinclair |first2=AJ |title=Nutritional influences in the evolution of mammalian brain. In: lipids, malnutrition & the developing brain |journal=Ciba Foundation symposium |pages=267–92 |year=1971 |pmid=4949878}}</ref> Like DHA, neurological health is reliant upon sufficient levels of arachidonic acid. Among other things, arachidonic acid helps to maintain hippocampal cell membrane fluidity.<ref>{{cite pmid|16790296}}</ref> It also helps protect the brain from oxidative stress by activating perioxisomal proliferator-activated receptor-y.<ref>{{cite journal |last1=Wang |first1=ZJ |last2=Liang |first2=CL |last3=Li |first3=GM |last4=Yu |first4=CY |last5=Yin |first5=M |title=Neuroprotective effects of arachidonic acid against oxidative stress on rat hippocampal slices |journal=Chemico-biological interactions |volume=163 |issue=3 |pages=207–17 |year=2006 |pmid=16982041 |doi=10.1016/j.cbi.2006.08.005}}</ref> ARA also activates syntaxin-3 (STX-3), a protein involved in the growth and repair of neurons.<ref>{{cite journal |last1=Darios |first1=F |last2=Davletov |first2=B |title=Omega-3 and omega-6 fatty acids stimulate cell membrane expansion by acting on syntaxin 3. |journal=Nature |volume=440 |issue=7085 |pages=813–7 |year=2006 |pmid=16598260 |doi=10.1038/nature04598 |bibcode=2006Natur.440..813D}}</ref>

Arachidonic acid is also involved in early neurological development. In one study funded by the U.S. National Institute of Child Health and Human Development, infants (18 months) given supplemental arachidonic acid for 17 weeks demonstrated significant improvements in intelligence, as measured by the Mental Development Index (MDI).<ref>Developmental Medicine and Child Neurology, March 2000{{Page needed|date=November 2010}}</ref> This effect is further enhanced by the simultaneous supplementation of ARA with DHA.

In adults, the disturbed metabolism of ARA may be associated with neurological disorders such as Alzheimer’s Disease and Bipolar Disorder.<ref>{{cite journal |last1=Rapoport |first1=SI |title=Arachidonic acid and the brain |journal=The Journal of nutrition |volume=138 |issue=12 |pages=2515–20 |year=2008 |pmid=19022981}}</ref> This may involve significant alterations in the conversion of arachidonic acid to other bioactive molecules (overexpression or disturbances in the ARA enzyme cascade). It is of note that the dietary arachidonic acid consumption is not associated with the onset of Alzheimer's disease, and studies suggest that the supplementation of arachidonic acid during the early stages of this disease may actually be effective in reducing symptoms and slowing the disease progress.<ref>{{cite journal |last1=Schaeffer |first1=EL |last2=Forlenza |first2=OV |last3=Gattaz |first3=WF |title=Phospholipase A2 activation as a therapeutic approach for cognitive enhancement in early-stage Alzheimer disease |journal=Psychopharmacology |volume=202 |issue=1–3 |pages=37–51 |year=2009 |pmid=18853146 |doi=10.1007/s00213-008-1351-0}}</ref> Additional studies on the supplementation of arachidonic acid with Alzheimer's are needed.

===Bodybuilding supplement===

Arachidonic acid is marketed as an anabolic bodybuilding supplement in a variety of products. The first clinical study concerning the use of arachidonic acid as a sport supplement was conducted at Baylor University and published in the ''Journal of the International Society of Sports Nutrition''.<ref>{{cite journal |last1=Roberts |first1=MD |last2=Iosia |first2=M |last3=Kerksick |first3=CM |last4=Taylor |first4=LW |last5=Campbell |first5=B |last6=Wilborn |first6=CD |last7=Harvey |first7=T |last8=Cooke |first8=M |last9=Rasmussen |first9=C |title=Effects of arachidonic acid supplementation on training adaptations in resistance-trained males |journal=Journal of the International Society of Sports Nutrition |volume=4 |pages=21 |year=2007 |pmid=18045476 |pmc=2217562 |doi=10.1186/1550-2783-4-21}}</ref>

The performance data results from the paper include the following statistically significant improvement, and statistically strong trends:

A significant group × time interaction for relative Wingate peak power was observed among groups (P = 0.02) with gains in peak power being significantly greater in the AA group (0.3 ± 1.2 W·kg-1) vs. PLA (0.2 ± 0.7 W·kg-1, Figure 1). Using repeated measures ANOVA with delta scores, AA experienced significantly greater increases in comparison to the PLA group at day 50 (P < 0.05). Statistical trends were seen in Wingate total work (AA: 1,292 ± 1,206 vs. PLA: 510 ± 1,249 J, P = 0.09, ηp 2 = 0.052), favoring the AA group.

With regard to inflammation, the paper reported a statistically significant reduction in resting IL-6 levels (a central regulator of inflammation):

IL-6 levels experienced a significant group × time interaction (P = 0.04) among groups with subsequent post-hoc analyses revealing that IL-6 was significantly lower at day 25 of the study. One way ANOVA of IL-6 delta values at day 25 revealed significantly greater increases in PLA when compared to AA group (AA: 0.8 ± 13.5 pg·ml-1 vs. PLA: 52.5 ± 1.6 pg·ml-1, P = 0.01; Figure 2)

Arachidonic acid was shown to improve peak muscle power, reduce resting IL-6 levels, and produce statistically strong trends of improvements in muscle endurance, average power, and bench press 1-rep maximum lift. This study provides preliminary evidence supporting the use of arachidonic acid in sports nutrition. Further research is needed.

==Dietary arachidonic acid and inflammation==

Under normal metabolic conditions, the increased consumption of arachidonic acid is unlikely to increase inflammation. ARA is metabolized to both pro-inflammatory and anti-inflammatory molecules.<ref name =Harris>{{cite journal |last1=Harris |first1=WS |last2=Mozaffarian |first2=D |last3=Rimm |first3=E |last4=Kris-Etherton |first4=P |last5=Rudel |first5=LL |last6=Appel |first6=LJ |last7=Engler |first7=MM |last8=Engler |first8=MB |last9=Sacks |first9=F |title=Omega-6 fatty acids and risk for cardiovascular disease: a science advisory from the American Heart Association Nutrition Subcommittee of the Council on Nutrition, Physical Activity, and Metabolism; Council on Cardiovascular Nursing; and Council on Epidemiology and Prevention |journal=Circulation |volume=119 |issue=6 |pages=902–7 |year=2009 |pmid=19171857 |doi=10.1161/CIRCULATIONAHA.108.191627}}</ref> Studies giving between 840&nbsp;mg and 2,000&nbsp;mg per day to healthy individuals for up to 50 days have shown no increases in inflammation or related metabolic activities.<ref name=Harris/><ref name=Nelson97>{{cite journal |doi=10.1007/s11745-997-0055-7 |last1=Nelson |first1=GJ |last2=Schmidt |first2=PC |last3=Bartolini |first3=G |last4=Kelley |first4=DS |last5=Kyle |first5=D |title=The effect of dietary arachidonic acid on platelet function, platelet fatty acid composition, and blood coagulation in humans |journal=Lipids |volume=32 |pmid=9113631 |issue=4 |pages=421–5 |year=1997}}</ref><ref name=Wilborn>Changes in whole blood and clinical safety markers over 50 days of concomitant arachidonic acid supplementation and resistance training. Wilborn, C, M Roberts, C Kerksick, M Iosia, L Taylor, B Campbell, T Harvey, R Wilson, M. Greenwood, D Willoughby and R Kreider. Proceedings of the International Society of Sports Nutrition (ISSN) Conference June 15–17, 2006. http://arachidonic.com/ARA-baylorsafety.pdf</ref><ref>{{cite journal |last1=Pantaleo |first1=P |last2=Marra |first2=F |last3=Vizzutti |first3=F |last4=Spadoni |first4=S |last5=Ciabattoni |first5=G |last6=Galli |first6=C |last7=La Villa |first7=G |last8=Gentilini |first8=P |last9=Laffi |first9=G |title=Effects of dietary supplementation with arachidonic acid on platelet and renal function in patients with cirrhosis |journal=Clinical science |volume=106 |issue=1 |pages=27–34 |year=2004 |pmid=12877651 |doi=10.1042/CS20030182}}</ref> Increased arachidonic acid levels are actually associated with reduced pro-inflammatory IL-6 and IL-1 levels, and increased anti-inflammatory tumor-necrosis factor-beta.<ref>{{cite journal |last1=Ferrucci |first1=L |last2=Cherubini |first2=A |last3=Bandinelli |first3=S |last4=Bartali |first4=B |last5=Corsi |first5=A |last6=Lauretani |first6=F |last7=Martin |first7=A |last8=Andres-Lacueva |first8=C |last9=Senin |first9=U |title=Relationship of plasma polyunsaturated fatty acids to circulating inflammatory markers |journal=The Journal of clinical endocrinology and metabolism |volume=91 |issue=2 |pages=439–46 |year=2006 |pmid=16234304 |doi=10.1210/jc.2005-1303}}</ref> This may result in a reduction in systemic inflammation.

Arachidonic acid does still play a central role in inflammation related to injury and many diseased states. How it is metabolized in the body dictates its inflammatory or anti-inflammatory activity. Individuals suffering from joint pains or active inflammatory disease may find that increased arachidonic acid consumption exacerbates symptoms, probably because it is being more readily converted to inflammatory compounds. Likewise, high arachidonic acid consumption is not advised for individuals with a history of inflammatory disease, or that are in compromised health. It is also of note that while ARA supplementation does not appear to have pro-inflammatory effects in healthy individuals, it may counter the anti-inflammatory effects of omega-3 EFA supplementation.<ref>{{cite journal |last1=Li |first1=B |last2=Birdwell |first2=C |last3=Whelan |first3=J |title=Antithetic relationship of dietary arachidonic acid and eicosapentaenoic acid on eicosanoid production in vivo |journal=Journal of lipid research |volume=35 |issue=10 |pages=1869–77 |year=1994 |pmid=7852864}}</ref>

==Health effects of arachidonic acid supplementation==

Arachidonic acid supplementation in daily dosages of 1,000-1,500&nbsp;mg for 50 days has been well tolerated during several clinical studies, with no significant side effects reported. All common markers of health including kidney and liver function,<ref name=Wilborn/> serum lipids,<ref>{{cite journal |last1=Nelson |doi=10.1007/s11745-997-0056-6 |first1=GJ |last2=Schmidt |first2=PC |last3=Bartolini |first3=G |last4=Kelley |first4=DS |last5=Phinney |first5=SD |last6=Kyle |first6=D |last7=Silbermann |first7=S |last8=Schaefer |first8=EJ |title=The effect of dietary arachidonic acid on plasma lipoprotein distributions, apoproteins, blood lipid levels, and tissue fatty acid composition in humans |journal=Lipids |volume=32 |pmid=9113632 |issue=4 |pages=427–33 |year=1997}}</ref> immunity,<ref>{{cite journal |doi=10.1007/s11745-998-0187-9 |last1=Kelley |first1=DS |last2=Taylor |first2=PC |last3=Nelson |first3=GJ |last4=MacKey |first4=BE |title=Arachidonic acid supplementation enhances synthesis of eicosanoids without suppressing immune functions in young healthy men |journal=Lipids |pmid=9507233 |volume=33 |issue=2 |pages=125–30 |year=1998}}</ref> and platelet aggregation<ref name=Nelson97/> appear to be unaffected with this level and duration of use. Furthermore, higher concentrations of ARA in muscle tissue may be correlated with improved insulin sensitivity.<ref>{{cite journal |last1=Borkman |first1=M |last2=Storlien |first2=LH |last3=Pan |first3=DA |last4=Jenkins |first4=AB |last5=Chisholm |first5=DJ |last6=Campbell |first6=LV |title=The relation between insulin sensitivity and the fatty-acid composition of skeletal-muscle phospholipids |journal=The New England journal of medicine |volume=328 |issue=4 |pages=238–44 |year=1993 |pmid=8418404 |doi=10.1056/NEJM199301283280404}}</ref> Arachidonic acid supplementation by healthy adults appears to offer no toxicity or significant safety risk.

A scientific advisory from the American Heart Association has favorably evaluated the health impact of dietary Omega-6 fats, including arachidonic acid.<ref>{{cite journal |last1=Harris |first1=WS |last2=Mozaffarian |first2=D |last3=Rimm |first3=E |last4=Kris-Etherton |first4=P |last5=Rudel |first5=LL |last6=Appel |first6=LJ |last7=Engler |first7=MM |last8=Engler |first8=MB |last9=Sacks |first9=F |title=Omega-6 Fatty Acids and Risk for Cardiovascular Disease: A Science Advisory From the American Heart Association Nutrition Subcommittee of the Council on Nutrition, Physical Activity, and Metabolism; Council on Cardiovascular Nursing; and Council on Epidemiology and Prevention |journal=Circulation |volume=119 |issue=6 |pages=902–7 |year=2009 |pmid=19171857 |doi=10.1161/CIRCULATIONAHA.108.191627}}</ref> The group does not recommend limiting this EFA. In fact, the paper recommends individuals follow a diet that consists of at least 5-10% of calories coming from omega-6 fats, including arachidonic acid. Dietary ARA is not a risk factor for heart disease, and may play a role in maintaining optimal metabolism and reduced heart disease risk. It is, therefore, recommended to maintain sufficient intake levels of both omega 3 and omega 6 essential fatty acids for optimal health.

Arachidonic acid is not carcinogenic, and studies show the dietary level is not associated with an increased risk of cancers.<ref>{{cite journal |last1=Schuurman |first1=AG |last2=Van Den Brandt |first2=PA |last3=Dorant |first3=E |last4=Brants |first4=HA |last5=Goldbohm |first5=RA |title=Association of energy and fat intake with prostate carcinoma risk: results from The Netherlands Cohort Study |journal=Cancer |volume=86 |issue=6 |pages=1019–27 |year=1999 |pmid=10491529 |doi=10.1002/(SICI)1097-0142(19990915)86:6<1019::AID-CNCR18>3.0.CO;2-H}}</ref><ref>{{cite journal |last1=Leitzmann |first1=MF |last2=Stampfer |first2=MJ |last3=Michaud |first3=DS |last4=Augustsson |first4=K |last5=Colditz |first5=GC |last6=Willett |first6=WC |last7=Giovannucci |first7=EL |title=Dietary intake of n-3 and n-6 fatty acids and the risk of prostate cancer |journal=The American journal of clinical nutrition |volume=80 |issue=1 |pages=204–16 |year=2004 |pmid=15213050}}</ref><ref>{{cite journal |last1=Astorg |first1=P |title=Dietary fatty acids and colorectal and prostate cancers: epidemiological studies |journal=Bulletin du cancer |volume=92 |issue=7 |pages=670–84 |year=2005 |pmid=16123006}}</ref><ref>{{cite journal |last1=Whelan |first1=J |last2=McEntee |first2=MF |title=Dietary (n-6) PUFA and intestinal tumorigenesis |journal=The Journal of nutrition |volume=134 |issue=12 Suppl |pages=3421S–3426S |year=2004 |pmid=15570048}}</ref> ARA remains integral to the inflammatory and cell growth process, however, which is disturbed in many types of disease including cancer. Therefore, the safety of arachidonic acid supplementation in patients suffering from cancer, inflammatory, or other diseased states is unknown, and supplementation is not recommended.

* [[Polyunsaturated fatty acid]]

* [[Aspirin]]—inhibits [[cyclooxygenase]] enzyme to prevent the conversion of arachidonic acid to other signal molecules

{{reflist|30em}}

* [http://www.acnp.org/g4/GN401000059/Default.htm Arachidonic Acid] at acnp.org

[[cs:Kyselina arachidonová]]

[[da:Arakidonsyre]]

[[de:Arachidonsäure]]

[[es:Ácido araquidónico]]

[[fa:اسید آراشیدونیک]]

[[fr:Acide arachidonique]]

[[it:Acido arachidonico]]

[[he:חומצה ארכידונית]]

[[lv:Arahidonskābe]]

[[nl:Arachidonzuur]]

[[ja:アラキドン酸]]

[[pl:Kwas arachidonowy]]

[[pt:Ácido araquidônico]]

[[ru:Арахидоновая кислота]]

[[sl:Arahidonska kislina]]

[[sr:Arahidonska kiselina]]

[[fi:Arakidonihappo]]

[[sv:Arakidonsyra]]

[[zh:花生四烯酸]]