Moravol, spol. s r.o.

Informations for specialists

What are Omega-3 and Omega-6 fatty acids?

Omega-3 (?3) and omega-6 (?6) fatty acids are unsaturated "Essential Fatty Acids" (EFAs) that need to be included in the diet because the human metabolism cannot create them from other fatty acids. Since these fatty acids are polyunsaturated, the terms n-3 PUFAs and n-6 PUFAs are applied to omega-3 and omega-6 fatty acids, respectively. These fatty acids use the Greek alphabet (?,ß,?,...,?) to identify the location of the double bonds. The "alpha" carbon is the carbon closest to the carboxyl group (carbon number 2), and the "omega" is the last carbon of the chain because omega is the last letter of the Greek alphabet. Linoleic acid is an omega-6 fatty acid because it has a double bond six carbons away from the "omega" carbon. Linoleic acid plays an important role in lowering cholesterol levels. Alpha-linolenic acid is an omega-3 fatty acid because it has a double bond three carbons away from the "omega" carbon. By subtracting the highest double-bond locant in the scientific name from the number of carbons in the fatty acid we can obtain its classification. For arachidonic acid, we subtract 14 from 20 to obtain 6; therefore, it is an omega-6 fatty acid. This type of terminology is sometimes applied to oleic acid which is an omega-9 fatty acid.

In these simplified structural formulas of unsaturated fatty acids, each angle represents a carbon atom. Notice that all the double bonds have the Cis configuration.

DHA (docosahexaenoic acid) and AA (arachidonic acid) are both crucial to the optimal development of the brain and eyes. The importance of DHA and AA in infant nutrition is well established, and both substances are routinely added to infant formulas. Excessive amounts of omega-6 polyunsaturated fatty acids and a very high omega-6/omega-3 ratio have been linked with pathogenesis of many diseases, including cardiovascular disease, cancer, and inflammatory and autoimmune diseases. The ratio of omega-6 to omega-3 in modern diets is approximately 15:1, whereas ratios of 2:1 to 4:1 have been associated with reduced mortality from cardiovascular disease, suppressed inflammation in patients with rheumatoid arthritis, and decreased risk of breast cancer.

Where can be Omega-3 and Omega-6 fatty acids found?

In general, these polyunsaturated fatty acids are present especially in many plant and fish oils and fats. The only difference is in quantity of particular fatty acid in whole composition of the oil. For examples, please, refer to the following table, where polyunsaturated fatty (linoleic and linolenic) acids are listed in the last two columns.

Fatty acid composition of some common edible fats and oils.

Percent by weight of total fatty acids.

* Not high-oleic variety.

Percentages may not add to 100% due to rounding and other constituents not listed.

Where percentages vary, average values are used.

The influence of these essential fatty acids on human health is evident and outright. There are many scientific papers and clinical studies confirming the essentiality of these substances in nutrition. These substances are the corner stone of complex metabolic pathways leading to the very active biological moderators such as prostaglandines, leucotrienes, tromboxanes, prostacyclines, etc. Moreover, the daily intake of the polyunstaurated fatty acids in appropriate ratio is necessary for sensitive balance of many other biochemical processes, e.g. level of the blood cholesterol, right transmission of nervous signals, etc.

Why are Milk thistle oil and Moldavian dragonhead oil important?

The importance of these oils inheres in the fatty acids composition and also in the presence of other important biological active substances.

Milk thistle oil does contain the high portion of linoleic acid (omega-6) in the triacylglyceryl part. On the other hand, the content of saturated fatty acid is lower in comparison with the other plant oils containing substantial amount of linoleic acid. This is the main reason why Milk thistle oil should play an important role in the nutrition.

On the other hand, Milk thistle oil exhibits also some excellent properties as the part of dermatological preparations. Beside the triacylglyceride part of oil, in virgin oil we can find a significant amount of (about 5% w/w) of mono- and diacylglycerols which increase the total oil polarity. This property is very important for the spreadability of the preparation made of Milk thistle oil. Thus, Milk thistle oil with the interfacial tension of 16 mN.m-1 on the oil/water phase interface belongs to very polar oils, such as e.g. avocado oil. The spreadability of Milk thistle oil is comparable with the esters of fatty acids with medium chain alcohols, e.g. decyl oleate. Polar oils in general have a much better ability to act as the carriers of biologically active substances. Their behavior in the skin is closer to sebum properties than the behavior of paraffinic oils. The unsaponifiable part of Milk thistle oil represents approximately 1% w/w of the oil. This fraction is rich on phytosterols which are proven to be anti-ageing and moisturizing agents. The phystosterol fraction consists mainly from beta-sitosterol and delta-7-stigmasterol; delta-5-avenasterol, stigmasterol and campesterol are present as the minor substances. The other sterols such as cholestan-3-ol, delta-7-avenasterol, cholesterol and 5,24-stigmastadienol are detected in traces only.

Moldavian dragonhead oil possesses one of the highest polyunsaturated fatty acids content. Due to specific biosynthetic pathway in Moldavian dragonhead plants, its oil is rich on alpha-linolenic acid (omega-3) which content exceeds 60% w/w in total fatty acids composition. With respect to the fatty acids composition it could be considered as nearly ideal fatty acids source in human nutrition.

As Milk thistle oil as Moldavian dragonhead oil can be successfully applied into the skin preparations. The oil provides the unique texture feeling – it is non-greasy, with high lubricity, being quickly absorbed into deep layers of the skin. The most important properties of Moldavian dragonhead oil are protecting and anti-ageing effects. This oil is recommended for use in treatment of atopic eczema, acne and psoriasis. The unsaponifiable part of Moldavian dragonhead oil consists of several phytosterols with beta-sitosterol as the major substance. Campestrol and delta-5-avenasterol are present as the minor substances and stigmasterol, 5,24-stigmastadienol and delta-7-stigmasterol are detected in traces only.

The characteristic fatty acid profiles of both Milk thistle and Moldavian dragonhead oil are introduced in following table.

Fatty acid composition of Milk thistle and Moldavian dragonhead oils.

Percent by weight of total fatty acids.

Percentages may not add to 100% due to rounding and other constituents not listed.

Where percentages vary, average values are used.

What is the refined oil?

The main aim and purpose of the oil refinement in general term is to avoid the undesired substances from the primarily obtained crude oil. Such procedure can be performed by many technologies. Some of them are often used in large production scale for the processing of huge amount of common plant oils some of them are very effective but quite expensive and are used for special oil refinement only. On the other hand, the oils with high content of polyunsaturated fatty acids requires another, more sensitive approach to their refinement to avoid any changes in positions and geometry of double bonds. This was also the main task for the technology development of oil refinement at Moravol, spol. s r.o.. For the time being, four main principles are applied in the oil refinement procedures:

1. Minimization of the exposition of oil to heat from first step (oil pressing) to final step (final refinement)
2. Avoiding the exposition of oil to air by application of the inert atmosphere at all processes including the storage of intermediates an final products
3. Avoiding all the procedures where water must be used
4. Utilization of selective procedures which are able to eliminate only undesired substances from oil.

Based on the above mentioned principles, the refined oils lose the colour and smell of primarily obtained oil, the water content is very low as well as the content of degradation products. Conversely, the amount of unsaponifiable matter and the amount of mono-, di- and triacylglycerols can be kept on defined level without changes in their chemical structures.

What are conjugated fatty acids?

Conjugated fatty acids are the isomers of polyunsaturated fatty acids. The principle of its carbon chain skeleton construction is that the double bonds are located in conjugated position, i.e. between two double bonds only one single bond is located and this arrangement is repeated regularly.

These substances occur in the natural fat in form of triglycerides in beef and diary products and are synthesized by bacteria in the rumen of the source animals. Since conjugated polyunsaturated fatty acids are of animal origin, their daily uptake decreases proportionally to changes in the human nutrition during last period. On the other hand, the importance of conjugated polyunsaturated fatty acids for right function of human organism has been confirmed by many independent scientific studies. The action of conjugated polyunsaturated fatty acids includes mainly:

1. Decrease of total body fat
2. Anticancer activity
3. Immune support
4. Cardiovascular health
5. Inhibition of tumor growing
6. Prevention of muscle wasting (anti-catabolic effects)

The exact mechanism by which conjugated polyunsaturated fatty acids may act is still not fully revealed. One of most probable possibility is that they may influence the eicosanoid synthesis. In testing of antioxidant activity were conjugated polyunsaturated fatty acids oxidized as rapidly as the corresponding non-conjugated fatty acids. It means that conjugated polyunsaturated fatty acids can be involved in the group of strong antioxidants.

The characteristic of conjugated fatty acids from Milk thistle and Moldavian dragonhead oils

After the special chemical processing of Milk thistle oil the conjugated linoleic acids mixture is obtained. The proportions among all of possible geometric and position isomers are strongly dependent on many factors during the reaction leading to rearrangement of double bonds in the molecule of starting linoleic acid. Consequently, at given constant reaction conditions the characteristic profile of conjugated fatty acids is achieved.

In the case of Milk thistle oil, theoretically 16 isomers of conjugated linoleic acids are possible. The process applied in Moravol, spol. s r.o. provide the two main isomers only: 9(Z),11(E)-octadeca-9,11-dienoic acid and 10(E),12(Z)-octadeca-10,12-dienoic acid, whereas the residual 14 conjugated linoleic acids are present in the final product in traces only. In this case very these two major isomers of conjugated linoleic acid possess the most verified beneficial properties. The conversion of linoleic acid to the conjugated derivatives is practically quantitative and less than several per cent of starting linoleic acid can be found in final product.

Unfortunately, free conjugated linoleic acids have two main inconvenient properties:

1. They decompose easily due to oxidation
2. They are of semi-solid state which is not easy to handle with

These disadvantages can be eliminated by several ways. One of them is the esterification of free conjugated fatty acids with suitable alcohol. In case of lower alcohols with number of carbon atoms up to four are the resulting esters slightly viscous liquids those are much more stable against the oxidation compare to free acids. Additionally, the biological action of conjugated fatty acids bound in esters remains near the same as in case of free fatty acids.

Similarly to linoleic acid from Milk thistle oil also alpha-linolenic acid from Moldavian dragon head oil can be converted into appropriate conjugated forms. The only difference is that the number of total possible isomers is much higher in comparison with the linoleic acid. Moreover, the detailed biological action and following importance of particular conjugated linolenic acid is not fully discovered yet. These facts led to the conclusion that the total content of conjugated linolenic acids in final product is quantified although all the particular substances are determined during the analytical procedure in Moravol, spol. s r.o.. Also in this case the residual content of unconverted alpha-linolenic acid in final product remains on level of several per cent of its starting amount. With respect to above mentioned reasons, the free conjugated linolenic acids are further transformed into its ethyl esters which are more stable and easier handling compare to free acids.