Fish Oils: Ethyl Ester versus Triglyceride forms

Low strength natural fish oils are in triglyceride (TG) form, as are most natural oils. To purify the oils by removing impurities and less desirable fatty acids and to concentrate the EPA and DHA fatty acid components, molecular distillation is used.  This process allows the oil to vaporize at low temperatures under pressure and is also known as vacuum distillation. The resulting vapor is collected and cooled, stratifying into distinct layers of fatty acids. This allows a purer esterified oil (called an ethyl ester form, or EE) with higher levels of EPA-DHA than crude fish oils and removal of triglycerides and cholesterol as well as other undesirable components. 

Some companies like to add triglycerides back in; this dilutes the fish oil concentrate by about 20% and the process also introduces mono- and di-glycerides, which don’t exist in natural fish oils to a significant degree but are thought responsible for higher absorption levels of this reconverted triglyceride form (rTG) oil over natural triglyceride and ethyl ester forms. If no triglycerides are added back, the body’s own store of triglycerides will be used to bond to the fatty acids after absorption, potentially lowering serum triglycerides more than an rTG oil. 

Absorption from our guts is always in the form of free fatty acids, so the oil’s original triglycerides are typically discarded during digestion and reattached later from body stores. This lowers the potential of the TG or rTG oils to lower triglycerides already in our bodies since they introduce additional triglycerides, which may be absorbed either into the body (adding more triglycerides into the liver) or into fiber or other materials that carry cholesterol out through the stool (potentially reducing the removal of cholesterol by competitive absorption). 

The prescription fish oils are in the ethyl ester form, not triglyceride form, because of the higher purity and higher strength of EE fish oils over TG or rTG forms resulting in better study outcomes on cardiovascular health measures. 

Krill oil is distinct because of its phospholipid matrix that greatly enhances omega-3 absorption more than the EE, TG, or rTG forms of fish oil.

Fish Oil: Excerpts from a magazine interview with me

The balance of fatty acids in the body can promote inflammatory or non-inflammatory states. Higher amounts of omega-3 fats in the diet have been shown to modulate inflammation and keep it within healthy ranges. The various cellular and tissue damage that can occur from chronic inflammatory states are certainly not healthful. This basic mechanism of action implies a wide-ranging and powerful effect of omega-3 fats to support wellness. Additionally, these fats are part of brain and nerve structures, so they help to maintain the health of those tissues, as well.

Omega-3 and omega-6 fats have been called “essential fatty acids” since the body can’t manufacture them from other fats, as it typically can for other types of fat. The optimal ratio of omega-6 to omega-3 fats is somewhere between 1:1 and 3:1. The common American diet has been estimated to be over 15:1, a marked deviation from a healthy norm.

The benefits of most other non-omega-3 fatty acids in fish oil are not well-defined in the scientific literature. Fish oil naturally contains a range of fats, including cholesterol, triglycerides, and stearic acid. The ones that are considered less desirable, cholesterol and triglycerides, are sometimes removed from fish oils to further concentrate the omega-3 portion and allow higher strengths in fewer capsules.

All natural oils contain various mixtures of fatty acids in varying amounts. Omega-9 fats are best known as being abundant in Olive Oil, and are considered non-inflammatory and especially healthy if substituted for most omega-6 fats that are pro-inflammatory. Some natural oils are fairly well balanced, such as flax and hemp seed oils, or walnut oil. Others, like fish oil, tend to be predominantly omega-3. Most vegetable oils are mostly omega-6 fats and their predominance in the modern diet has been blamed for some of our poor health.

Some consumers do know about various sources of fish oil, and some have advantages or disadvantages. For example salmon is a favored source of omega-3 fats, though salmon oil typically contains less than other common fish oils. Traditional fish sources may be better accepted by those who won’t or can’t eat shellfish. The fisheries in Norway and Peru are among the best managed traditional fisheries on earth.

Krill, a small crustacean shellfish, is a unique source of omega-3 fats since krill also naturally bonds the fatty acids to phospholipids, which are essential for cell membranes and which enhance the bioavailability of the oil. Krill oil also contains the powerful antioxidant pigment astaxanthin, which is responsible for the color of shrimp and salmon. Krill is considered the best managed fishery in the world, with trained observers on each boat monitoring the harvest. The krill harvest limit can be rapidly adjusted to support a healthy population, and the total world harvest (most of which goes into pet foods) is only a fraction of the allowable sustainable harvest level.

Essential fatty Acids (EFAs) interview, Natural Products Marketplace magazine, January, 2011

The awareness of EFAs, especially the Omega-3 fatty acids EPA and DHA, is large and growing larger. The accumulating mountain of evidence and the endorsement by popular health “gurus” assures continued growth in this important product category. As the benefits of specific fatty acids for regulation of various healthy body functions – such as inflammatory processes, hormonal health, and maintaining brain/nerve/cellular structures – becomes even more well known, more and more people recognize the potential for EFAs to positively affect their health.

While there are combination products that deliver Omega-3, Omega-6, and Omega-9 fatty acids together, the focus has been more on specific sources such as fish or flax, along with some more unusual ones. Of course, natural oil sources are not comprised of a single fatty acid. For example, natural fish oil can not only supply EPA and DHA but also originally supplies ALA, cholesterol, triglycerides, and other fatty acids; though many of these components can be removed during processing to provide purer and stronger materials that are richer in EPA and DHA to require far fewer capsules to reach desired levels of these two fractions. Flax oil is best known as a vegetarian source of the omega-3 fatty acid ALA (alpha-linolenic acid), but ALA levels are only about 55% of the total; flax oil also contains about 19% omega-9 as oleic acid, 14% omega-6 as linoleic acid, and 12% saturated fats. The conversion of ALA to EPA is a significant metabolic hurdle. Women do this conversion better than men; people who consume the most omega-6 in their diets have a more difficult time converting ALA to EPA. Typically between 5% and 15% of ALA converts to EPA and about 2% to 5% of ALA converts to DHA, making flax a much more dilute and less certain source of EPA-DHA.

Fish oil is subject to environmental concerns related to both sustainability and contaminants. Manufacturers audit their suppliers and set strict identity/safety specifications to assure the quality of products.

Most fish oils are molecularly distilled to remove contaminants, manufactured under strict quality assurance standards, and screened to be free of potentially harmful levels of contaminants and heavy metals, such as mercury, PCB’s, dioxins, and others.

Other types of EFAs include Flax seed oil, Evening Primrose Oil, Pumpkin seed oil, Black Currant seed oil, Wheat Germ oil, Castor Oil, and Virgin Coconut Oil.

Purity, potency, and freshness are always the challenges with EFAs.

The trend is toward more concentrated products of higher purity that allow people to get their EPA and DHA with smaller quantities of capsules or less volume of liquid. Liquids and smaller capsule sizes allow more children and seniors to enjoy the benefits of fish oils, while high strength capsules better hit the main demographic in between.

All fish oil supplements are typically hundreds of times safer than eating a serving of fish in relation to environmental factors; and typical esterified products have the added benefit of being free of cholesterol and triglycerides, which are undesirable food components for those with high cholesterol. By far, most of the studies proving the health benefits of supplemental fish oils have been with the esterified (ethyl ester) form, rather than the triglyceride form found in cold water fatty fish. There is very strong science supporting the use of this form.

Esterified fish oils also have been shown to sustain human serum levels better than the triglyceride form, over both a 24-hour period and a one-month period, which better supports a healthy heart rhythm. Notably, the most concentrated products are available only as esterified fatty acids. The ability of a consumer to get the 1-3 grams daily of EPA + DHA recommended by many health experts is enhanced by modern formulas that concentrate these essential fatty acids into fewer capsules and smaller serving sizes with fewer undesirable components, thus increasing customer compliance with a healthy nutritional protocol.

Both triglyceride and esterified ethyl ester fish oils are available in the marketplace, and both forms have their advocates. In the body, both forms must first be digested, stripping off the triglycerides or ethyl esters and leaving only free fatty acids that can be readily absorbed. These free fatty acids are then combined with triglycerides present in the liver before entering general circulation; so the circulating form will actually be the triglyceride form, no matter which form of fish oil one consumes. Both forms provide great value and important nutrients for the consumer; but the triglyceride form has no more proven value than the ethyl ester form, despite some excessive marketing claims.

Detoxification

Detoxification By Neil E. Levin, CCN, DANLA The EPA tracks about 650 toxic chemicals used in 23,600 facilities in the US. The agency reports that about half of the 4.24 billion pounds of these toxic chemicals are annually released into the air, ground or water. These include chemicals from the mining, smelting and power generation industries, paper production, electronic equipment manufacturing, plastics, pesticides, etc. While the highest release of chemicals is associated with mining and power production, other industries release problematic chemicals into the environment on a daily basis, all over our country. Certain groups are most at risk (e.g., children, pregnant and nursing women, the elderly). I would also add that people with multiple chemical exposures or even a single toxic level of exposure can develop a hyper-sensitivity to chemicals that can be debilitating. This condition is often called multiple chemical sensitivity. Of course, there is an increase in exposures as our exposure to so many chemicals uses up key nutrients and can overload the body’s ability to detoxify these toxic “insults” to the liver and other body systems. As our need for key nutrients and optimal detoxification processes grows during repeated, chronic exposures, our bodies may fail to keep pace and the levels of toxins can accumulate in our body. The results can be subtle (acne, headaches, persistent “colds”) or extreme (hair or tooth loss, chronic fatigue, pain). We see inflammatory-related conditions increasing, such as liver problems, cardiovascular issues, joint degradation and brain degeneration. While it is true that these conditions are associated with aging, it is also true that aging relates to the body’s inability to properly remove toxins and distribute nutrients to all of its tissues. Inflammatory chemicals can be either the original chemical or a biochemical metabolite that is produced in the body as a temporary step in neutralizing and removing the chemical. If inadequate nutrient stores do not allow the detoxification to complete - and often heroic levels of nutrients far above the RDI’s are required in these situations – then the body still will have a burden of toxic, inflammatory chemicals to contend with. The old adage is to reduce the exposure and increase the nutrients in order to allow the body to clear these toxins in its usual manner. Everything that lowers exposure, even removing shoes when entering a house or using appropriate filters for air ducts, may be helpful in reducing airborne toxins. But it is also important to reduce exposures through varied sources such as medications, non-organic food and the environment as best we can. Antioxidants, including sulfur-containing substances, are the key to detoxification. Methylation, sulfation and antioxidant reduction are some detoxification techniques used by the liver, especially. The liver utilizes these methods to render toxins inert enough to allow removal through the bile or the urine. Methylation can be enhanced by methyl donor nutrients, such as choline, TMG, DMG and SAMe. Sulfation is done with MSM, sulfur from plants (garlic, onions, broccoli, kale) or sulfur-containing proteins (methionine, cysteine, glutathione). Antioxidants include Vitamin C, alpha lipoic acid, etc. Any sources of these nutrients would be beneficial to aiding the body’s natural detoxification systems. One problem is that people often fear to use adequate, high levels of these nutrients, such as taking Vitamin C up to bowel tolerance levels. Some natural substances that enhance/support detoxification include Zinc, Selenium, Copper, Manganese, Sodium Alginate, Chlorella, Bladderwrack, MSM, Beet Root, Red Clover, Dandelion Root, Oregon Grape Root, and Milk Thistle Extract. Another new product is a broccoli seed concentrate called “sgs™”, which is backed by numerous clinical studies at Johns Hopkins regarding its ability to enhance natural detoxification. Adequate fiber is also important in moving the waste quickly through the colon to help remove toxins while avoiding exposure to toxins from the waste or from inappropriate microbes that fester in an unhealthy colon. Probiotics are important, especially bifidobacteria (Bifidus). Drinking adequate amounts of clean, filtered water is another must. Eating organic whenever possible is important, avoiding non-organic fruits and vegetables prone to heavy chemical exposure. Detoxification is a normal bodily function, so claiming that a dietary supplement can support this function would be a legitimate “structure-function statement” authorized by federal law if the clinical documentation is available. Neil E. Levin, CCN, DANLA is a nationally certified clinical nutritionist with a Diplomate in Advanced Nutritional Laboratory Assessment. He is a professional member of the International & American Associations of Clinical Nutritionists. Neil is the nutrition education manager and a product formulator for NOW Foods, a natural food and dietary supplement manufacturer in Bloomingdale, Illinois. Neil is a member of the Scientific Council of the national Clinical Nutrition Certification Board and serves on the board of directors of the Mid-American Health Organization (MAHO), the Midwest regional affiliate of the National Products Association (formerly NNFA). Neil is routinely interviewed for articles in trade magazines serving the natural products industry and has published articles in magazines and newspapers, contributed to scientific journals and has been a guest on numerous radio shows. He has been interviewed for television news reports many times over a 33-year career. You can read some of Neil’s recent articles at his non-commercial website: http://www.honestnutrition.com/

Omega-3 fats, depression and mood disorders

Studies do show the potential benefits, and also evidence the good tolerability, of omega-3 fats in mood disorders. While these nutrients may not be a "cure" or even a drug-like treatment, their protective effects in these patient groups has been fairly well established: "Biological marker studies indicate deficits in omega-3 fatty acids in people with depressive disorders, while several treatment studies indicate therapeutic benefits from omega-3 supplementation. A similar contribution of omega-3 fatty acids to coronary artery disease may explain the well-described links between coronary artery disease and depression." Parker G, et al. Omega-3 fatty acids and mood disorders. Am J Psychiatry. 2006 Jun;163(6):969-78. Review. Erratum in: Am J Psychiatry. 2006 Oct;163(10):1842. PMID: 16741195 "Five of six double-blind, placebo-controlled trials in schizophrenia, and four of six such trials in depression, have reported therapeutic benefit from omega-3 fatty acids in either the primary or secondary statistical analysis, particularly when EPA is added on to existing psychotropic medication. Individual clinical trials have suggested benefits of EPA treatment in borderline personality disorder and of combined omega-3 and omega-6 fatty acid treatment for attention-deficit hyperactivity disorder. The evidence to date supports the adjunctive use of omega-3 fatty acids in the management of treatment unresponsive depression and schizophrenia." Peet M, Stokes C. Omega-3 fatty acids in the treatment of psychiatric disorders. Drugs. 2005;65(8):1051-9. Review. PMID: 15907142 "The preponderance of epidemiologic and tissue compositional studies supports a protective effect of omega-3 EFA intake, particularly eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), in mood disorders. Meta-analyses of randomized controlled trials demonstrate a statistically significant benefit in unipolar and bipolar depression (p = .02). The results were highly heterogeneous, indicating that it is important to examine the characteristics of each individual study to note the differences in design and execution. There is less evidence of benefit in schizophrenia. EPA and DHA appear to have negligible risks and some potential benefit in major depressive disorder and bipolar disorder, but results remain inconclusive in most areas of interest in psychiatry...Health benefits of omega-3 EFA may be especially important in patients with psychiatric disorders, due to high prevalence rates of smoking and obesity and the metabolic side effects of some psychotropic medications." Freeman MP, et al. Omega-3 fatty acids: evidence basis for treatment and future research in psychiatry. J Clin Psychiatry. 2006 Dec;67(12):1954-67. Review. PMID: 17194275