NAV

Omega-6 fatty acids

Identification

Generic Name
Omega-6 fatty acids
DrugBank Accession Number
DB13168
Background

Omega-6 fatty acids are polyunsaturated fatty acids with a final carbon-carbon double bond in the n-6 position, that is, the sixth bond, counting from the methyl end. They are a family of fatty acid molecules that act as precursors to potent lipid mediator signalling molecules with either pro-inflammatory and anti-inflammatory effects. Cells involved in the inflammatory response are typically rich in the n-6 fatty acid arachidonic acid, as generally, eicosanoids derived from n-6 PUFA are pro-inflammatory. Arachidonic acid, which is a main precursor of eicosanoids, is an example of omega-6 (n-6) polyunsaturated fatty acids. Vegetable oil is a major dietary sources of omega-6 fatty acids.

Type
Small Molecule
Groups
Nutraceutical
Synonyms
  • n-6 fatty acids
  • Omega 6 acids
  • Omega 6 fatty acids
  • ω-6 fatty acids
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Pharmacology

Indication

There are no current pharmacotherapeutic products based on omega-6 fatty acids.

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Pharmacodynamics

Omega-6 fatty acids mediate pro-inflammatory effects in the cellular level and compete for the same rate-limiting enzymes with omega-3 fatty acids. Arachidonic acid is converted to inflammatory mediators such as omega-6 prostaglandins and leukotriene eicosanoids during the inflammatory cascade. AA-derived eicosanoids are proinflammatory but they have important homeostatic functions in regulating both the promotion and resolution of inflammation in the immune response. It is reported that high intake of n-6 PUFA, along with low intakes of n-3 PUFA, shifts the physiological state to one that is proinflammatory and prothrombotic with increases in vasospasm, vasoconstriction, and blood viscosity and the development of diseases associated with these conditions. Thus maintaining the balance between 2 polyunsaturated fatty acids is critical in inflammatory cascade regulation.

Mechanism of action

Linoleic acid is the simplest omega-6 fatty acid that can generate longer n-6 polyunsaturated fatty acids such as eicosanoids, endocannabinoids and lipoxins by the insertion of additional double bonds during consecutive elongation and desaturation mechanisms. It gives rise to arachidonic acid (AA) via γ-linolenic acid (GLA, 18:3n-6) and dihomo-γ-linolenic acid (DGLA, 20:3n-6) and the same set of enzymes can also convert AA to EPA and DHA. The initial rate limiting desaturation of LA to GLA is catalysed by the enzyme delta-6-desaturase (FADS2) and elongation of GLA to DGLA by delta-5-desaturase (FADS1) generates AA 1. AA is also converted to 2-series prostaglandins (PGD2, PGE2, PGF2, PGI2) andthromboxanes (TXA2, TXB2) by COX-2 activity and 4-series leukotrienes (LTA4, LTB4, LTC4, LTD4, LTE4) by 5-LOX activity. Resulting lipid signalling molecules have various pro-inflammatory effects on target tissues and cells; bronchostriction, fever, pain, increased production of inflammatory cytokines such as TNF-alpha and IL-6, platelet aggregation, vasoconstriction, vascular permeability, chemotaxis of leukocytes, and release of reactive oxygen species by granulocytes 1. Omega-6 fatty acids activate PPAR to the less extent than omega-3 fatty acids, but a study involving human keratinocytes showed induction of COX-2 expression resulting from PPAR-alpha activation. Omega-6 fatty acids are also reported to directly activate syntaxin-3, a plasma protein membrane that regulates vesicle transport and growth of neurites 7.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Most metabolism of polyunsaturated fatty acids occur in the liver but may occur in other tissues as well. Metabolism of omega-6 fatty acids leads to biosynthesis of eicosanoids, as mentioned above. Linoleic acid can be metabolized to other more unsaturated, long-chain members of the n-6 family by the insertion of additional double bonds during consecutive elongation and desaturation mechanisms. The initial rate limiting desaturation of LA to GLA is catalysed by the enzyme delta-6-desaturase (FADS2). Elongation then takes place to convert GLA to DGLA, by elongation of very long-chain fatty acids (ELOVL) 5, and finally a cycle of elongation and desaturation by delta-5-desaturase (FADS1) generates AA 1.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
116Z6MZN1M
CAS number
Not Available
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

References

General References
  1. Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C: Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426. doi: 10.1155/2012/539426. Epub 2012 Apr 5. [Article]
  2. Calder PC: Omega-3 fatty acids and inflammatory processes. Nutrients. 2010 Mar;2(3):355-74. doi: 10.3390/nu2030355. Epub 2010 Mar 18. [Article]
  3. Simopoulos AP: The importance of the ratio of omega-6/omega-3 essential fatty acids. Biomed Pharmacother. 2002 Oct;56(8):365-79. [Article]
  4. Simopoulos AP: Evolutionary aspects of diet, the omega-6/omega-3 ratio and genetic variation: nutritional implications for chronic diseases. Biomed Pharmacother. 2006 Nov;60(9):502-7. Epub 2006 Aug 28. [Article]
  5. Simopoulos AP: The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases. Exp Biol Med (Maywood). 2008 Jun;233(6):674-88. doi: 10.3181/0711-MR-311. Epub 2008 Apr 11. [Article]
  6. Chene G, Dubourdeau M, Balard P, Escoubet-Lozach L, Orfila C, Berry A, Bernad J, Aries MF, Charveron M, Pipy B: n-3 and n-6 polyunsaturated fatty acids induce the expression of COX-2 via PPARgamma activation in human keratinocyte HaCaT cells. Biochim Biophys Acta. 2007 May;1771(5):576-89. Epub 2007 Mar 16. [Article]
  7. Darios F, Davletov B: Omega-3 and omega-6 fatty acids stimulate cell membrane expansion by acting on syntaxin 3. Nature. 2006 Apr 6;440(7085):813-7. [Article]
PubChem Substance
347911438
RxNav
1495153
Wikipedia
Omega-6_fatty_acid

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
Not Available
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Enzymes

Details1. Fatty acid desaturase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Stearoyl-coa 9-desaturase activity
Specific Function
Component of a lipid metabolic pathway that catalyzes biosynthesis of highly unsaturated fatty acids (HUFA) from precursor essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) ...
Gene Name
FADS2
Uniprot ID
O95864
Uniprot Name
Fatty acid desaturase 2
Molecular Weight
52259.075 Da
References
  1. Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C: Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426. doi: 10.1155/2012/539426. Epub 2012 Apr 5. [Article]
Details2. Fatty acid desaturase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity
Specific Function
Isoform 2 does not exhibit any catalytic activity toward 20:3n-6, but it may enhance FADS2 activity (By similarity). Isoform 1 is a component of a lipid metabolic pathway that catalyzes biosynthesi...
Gene Name
FADS1
Uniprot ID
O60427
Uniprot Name
Fatty acid desaturase 1
Molecular Weight
51963.945 Da
References
  1. Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C: Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426. doi: 10.1155/2012/539426. Epub 2012 Apr 5. [Article]
Details3. Prostaglandin G/H synthase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C: Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426. doi: 10.1155/2012/539426. Epub 2012 Apr 5. [Article]
Details4. Arachidonate 5-lipoxygenase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Iron ion binding
Specific Function
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name
ALOX5
Uniprot ID
P09917
Uniprot Name
Arachidonate 5-lipoxygenase
Molecular Weight
77982.595 Da
References
  1. Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C: Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426. doi: 10.1155/2012/539426. Epub 2012 Apr 5. [Article]

Drug created at February 12, 2017 03:42 / Updated at June 12, 2020 16:53