Omega 3 6 9 explained
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Omega 3 6 9 explained

XBrain’s Omega 3-6-9

XBrain’s omega 3-6-9 contains flax seed oil, fish oil, and sunflower oil. It therefore provides your body with the correct balance of linoleic acid, alpha-linoleic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid (HDA), the essential fatty acids necessary for good cardio-vascular health, and a well functioning immune and central nervous systems. It also contains the mono-saturated omega-9 oleic acid, and vitamin E.

Essential fatty acids cannot be synthesised by the human body and must be obtained in the diet. They are polyunsaturated, they have more than one double carbon bond. The nomenclature of the fatty acids reflects the position of the bond in relation to the terminal (omega) carbon. In omega-3 fatty acids the first carbon double bond is three carbons away from the end of the chain, in omega-6 fatty acids, it is 6 carbons away from the end of the chain, and so on.

Omega-3 -6 and -9 fatty acids are essential for normal human physiology. They are the precursors of many longer bioactive chains such as the eicosanoids, which mediate the inflammatory response, molecules active in the central nervous system, and endocannabinoids, which affect mood and behaviour. Their products can also regulate gene expression, by activating or inhibiting transcription factors in the nucleus.

In theory there are only two essential fatty acid, the omega-3 alpha-linoleic acid (ALA), found in the oils of many seeds, and the omega-6 linoleic acid (LA), found in vegetable oils. However, although eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), both omega-3 fatty acids, can be synthesised from alpha-linoleic acid, the process is inefficient in mammals. The main dietary source of EPA and DHA are oily fish, and fish oil supplementation had been shown to have many benefits for human health.

The Right Balance of Omega-3 and Omega-6 Fatty Acids



The diagram shows the competing pathways in which eicosanoids are synthesised from omega-3 and omega-6 fatty acids.  It was created by David R. Throop.

Because omega-3 and omega-6 fatty acids are modified through the same biochemical pathways, by the same enzymes, it is important that they are consumed in the right balance. It is thought that hunter-gatherers ate a diet that had an approximately equal proportion of omega-3 and omega-6 amino acids, and our bodies evolved to use them in this ratio. However, in the modern diet, high in linoleic acid-rich vegetable oils, omega-6 fatty acids are over represented by a ratio of 10:1, and sometimes as high as 30:1. This seriously impedes the body’s ability to use the omega-3 fatty acids in the diet, and creates an imbalance in the pro- and anti-inflammatory pathways. 

For example, the omega-6 linoleic acid is a precursor to arachidonic acid, while the omega-3 alpha-linoleic acid (ALA) is used to synthesise the longer omega-3 EPA and DHA. Both  synthesis pathways require the enzyme Δ6-desaturase, which is rate limiting. When excessive linoleic acid is present, it inhibits the synthesis of EPA and DHA from ALA,  reducing the levels of the longer omega-3 fatty acids in the tissues even further. 

Both arachidonic acid, and EPA sit at the heads of parallel biochemical cascades, shown in the diagram above, that produce eicosanoids, signaling molecules important in inflammation. Inflammation is an important defense against pathogenic organisms, and initiates the healing response to injury. However chronic inflammation is associated with many of the so called ‘diseases of civilisation’, whose rates are on the rise in industrialized countries.  It is possible that the great excess of omega-6 fatty acids compared to omega-3 fatty acids, which upsets the balance between pro-inflammation and anti-inflammation pathways, is a major cause of this increase.

The human body is able to synthesis EPA and DHA, if sufficient ALA is available, and in the absence of excessive linoleic acid. However, since this synthesis is not very efficient EPA and HDA should also be consumed. The major dietary source of the longer omega-3 fatty acids are oily fish. The American Heart Association recommends that they are eaten twice a week. An alternative is to take supplements containing fish oil, which have the advantage that there is no risk of methylmercury contamination, which is an increasing risk when eating fish or shellfish. An omega 3-6-9 supplement which has the correct balance of all the beneficial fatty acids, takes away the risk of ingesting toxins.

The Health Benefits of Omega-3 Fatty Acids

There is now solid scientific evidence, from numerous large clinical trials, that omega-3 fatty acids can significantly decrease the risk of heart disease.  Since EPA and HDA can be synthesised from ALA, their levels in the body will increase, if the consumption of ALA, present in the oils of many seeds and nuts is increased, especially relative to the consumption of the omega-6 linoleic acid (LA). 

Consuming more ALA relative to LA will also decrease the levels of arachidonic acid derived eicosanoids, and restore the balance between the pro-inflammatory and anti-inflammatory pathways mediated by the two types of essential fatty acids.

Since the production of EPA and HDA from ALA is not very efficient, and as explained above it can be inhibited by high levels of omega-6 fatty acids, doctors recommend that the intake of the two longer chained omega-3 fatty acids be increased, either through eating oily fish, or through supplementation with fish oil. 

EPA and DHA can improve the health of the cardiovascular system through preventing arrhythmias, which carry the risk of sudden cardiac death. They also decrease the risk of clot formation (thrombosis) that results in myocardial infarction or strokes. EPA and HDA are also important for the health of arteries, since they inhibit the deposition of cholesterol and fat plaques on artery walls, which leads to atherosclerosis. EPA and HDA fish oil supplements were shown to lower serum triglyceride levels. High triglyceride levels are associated with heart disease and diabetes. 

The eicosanoids and other bio-active molecules derived from EPA and HDA are anti-inflammatory, and there is much interest in their potential in treating inflammation-associated diseases. The evidence is particularly strong that fish oil supplements can relieve the symptoms of rheumatoid arthritis, and decrease the amount of NSAID (non steroidal anti-inflammatory drugs) that have to be taken by people suffering from the condition.

DHA is highly represented in the phospholipids in the gray matter of the brain. Although its molecular actions and mechanisms are not well understood, animal studies have shown that a deficiency of DHA in the brain causes learning delay.  It is possible that omega-3 fatty acids may play a role in cognitive function, and the prevention of Alzheimer’s disease and other dementias.

Omega-3 essential fatty acids are also thought to play a part in regulating mood and behaviour.  Their potential as treatments for depression, bipolar depression and attention deficit disorder are now being investigated.

Taking fish oil also appeared to help children with dyspraxia, a movement disorder

Very high concentrations of DHA are present in the cell membranes of the cells of the retina.  It appears to be required for the development and normal function of the retina, and seems to be needed for the synthesis of the rhodopsin, a visual pigment.  There is some evidence that consuming more fish oil in the diet helps protect agains age-related macular degeneration.

The Health Benefits of the  Omega-6 Essential Fatty Acid, Linoleic Acid


Linoleic acid, the only omega 6 essential fatty acid, might inhibit the beneficial effects of omega-3 fatty acids, yet it is still essential for human physiology.  The body  uses linoleic acid to synthesise longer chains, such as dihomo-gamma-linoleic-acid (DGLA) and arachidonic acid (AA).  AA is at the head of a biochemical cascade that synthesises physiologically active molecules such as prostoglandins, and endocannabinoids.

Arachidonic acid is an important structural component of cell membranes.  It is found in particularly high concentrations in the phospholipids of the brain’s grey matter, suggesting that it plays an important role in the correct functioning of the central nervous system (CNS).  As with the inflammatory response, high levels of the omega-3 fatty acid, DHA are also found in the CNS, suggesting that they might have the opposite effects to AA and that the correct ratios of omega-3 and omega-6 PUFAs is essential for balanced function.

First messengers such as neurohormones, neuromodulators and neurotransmitters activate phospholipidase enzymes, which release arachidonic acid from the cell membranes of CNS neurones.  Free AA molecules affect the behaviour of the ion channels and protein kinases in the neurones. It is also a precursor of eicosanoids which module neuronal excitability.

Intake of linoleic acid, in the correct ratio to omega-3 fatty acids, is associated with a reduction in the risk of developing cardiovascular disease.  One study shows that it has a strong effect at reducing serum LDL (bad cholesterol) levels when substituted for saturated fatty acids in the diet.  Vegetables oils, like sunflower oil have a high proportion of linoleic acid.

Oleic Acid

Oleic acid is a monounsaturated gamma-9 fatty acid. It has one double carbon bond, found on the 9th carbon from the end of the chain. It is not essential since the body can synthesise it by dehydrogenating stearic acid, using the enzyme stearoyl-CoA 9- desaturase. Nonetheless inclusion of oleic acid in the diet is associated with many health benefits. It is generally thought that the beneficial effects of olive oil, for example as part of the Mediterranean diet derive from the high levels of olive oil, and hence oleic acid consumed. 

It is now thought that it is oleic acid which is responsible for the blood pressure reducing effects of olive oil.  The omega-9 fatty acid is incorporated into the membranes of endothelial cells, and when it is present at high levels, in individuals who consume sufficient quantities of it, it modifies their biophysical properties.  In turn this affects the docking of G proteins, signal transduction molecules which span the plasma membrane, and which control blood pressure and other physiological responses. This property seems to be very specific to oleic acid,

Oleic acid also appears to have a very beneficial effect on serum cholesterol levels.  It seems to lower the levels of low density lipoprotein (LDL, sometimes called ‘bad’ cholesterol), while possibly also increasing the levels of high density lipoprotein (‘good cholesterol’), although the effects on HDL are not as clear.

Diets rich in oleic acid also increase oleate levels in low-density lipoprotein (LDL).  It appears that oleate-rich LDL are remarkably resistant to oxidation.  Since LDL oxidation is a crucial first step in the development of arterial plaques, this is probably another mechanism in which oleic acid helps protect against atherosclerosis.

It also help control blood sugar levels. A study of subjects with type 2 diabetes showed that changing from a polyunsaturated fat to monounsaturated fat diet reduced insulin resistance. Oleic acid also restored the endothelium’s ability to relax blood vessels, decreasing the chances of developing atherosclerosis, which is much higher in diabetics than in the general population.

Oleic acid is one of the components of Lonrenzo’s oil, an experimental treatment for asymptomatic people with adrenoleukodystrophy (ADL), a disease caused by the accumulation of very long chain fatty acids (VLCFAs). It is thought that the mixture of fatty acids in the oil can competitively inhibit the enzyme necessary for VLCFA formation. A preliminary study concluded that the oil does not alter the course of the disease in patients showing symptoms, but might prevent the disease developing in asymptomatic carriers.

Oleic acid image by Ben Mills, the image is in the public domain.

Vitamin E

The image of the structure of alpha-tocopherol is by Calvero and is in the public domain.

Vitamin E is actually a name that covers a group of fat soluble anti-oxidants.  Vitamin E exists in eight chemical forms, alpha, beta, gamma, and delta tocopherol and alpha-, beta-, gamma-, delta- tocotrienol. Alpha-tocopherol is the form that is biologically active.

After the different chemical forms are absorbed in the intestine they are processed by the liver.  Alpha-tocopherol is secreted into the bloodstream, through the hepatic alpha-tocopherol transfer protein, while the other forms are metabolized and excreted. 

The main health benefits of vitamin E are thought to derive from its anti-oxidant properties. Normal metabolic reactions in the body result in the formation of free radicals, chemical species with a free electron. These are very unstable and react with oxygen to form reactive oxygen molecules (ROM), which are less unstable, but still will still rapidly react with other molecules, as the name suggests. Other causes of free radical formation is air pollution, cigarette smoke, UV radiation in sunlight, and many other environmental factors.

Since free radicals damage cells and DNA, they are associated with many of chronic diseases. DNA damage can lead to mutations which result in cancer. Cumulative damage to neurones over time is thought to contribute to cognitive decline in old age, and might play a role in dementias.

Alpha-tocopherol stops the production of free radicals when fats are oxidized. It inhibits the oxidation of low-density lipoprotein (LDL), which is the first step in atherosclerosis, the formation of hard plaques on artery walls. 

Vitamin E plays an important part in reducing the risk of heart disease, cancer, eye disorders, such as age-related macular degeneration and possibly dementia.  When added to essential fatty acid supplements it also protects them from oxidation so they do not lose their value.

Further Reading

Health Benefits of omega-3 essential fatty acids:

http://www.nlm.nih.gov/medlineplus/druginfo/natural/993.html

http://lpi.oregonstate.edu/infocenter/othernuts/omega3fa/

http://nccam.nih.gov/research/results/spotlight/072811.htm

Oleic Acid in Health and Disease:

http://www.eurekaselect.com/106172/article

Oleic Acid’s effect on cholesterol:

http://jn.nutrition.org/content/119/4/529.full.pdf

Oleic Acid and blood pressure:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2544536/

Oleic Acid and blood sugar levels:

http://qjmed.oxfordjournals.org/content/93/2/85.long

Vitamin E Facts:

http://ods.od.nih.gov/factsheets/VitaminE-HealthProfessional/

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