Petroselinic acid and its use in food

Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Food or edible as carrier for pharmaceutical

Reexamination Certificate

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C424S078050, C514S786000, C514S787000

Reexamination Certificate

active

06365175

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to edible compositions containing petroselinic acid for anti-inflammatory and/or anti-aging use. Petroselinic acid is a well known compound that eg is present in coriander oil in relatively high amounts. Its use in food products is also disclosed in literature. EP 777971 eg discloses that fat compositions can be obtained from fats that have high contents of asymmetric monounsaturated fatty acids, such as petroselinic acid, ie PSA (>79 wt %) and that have simultaneously low contents of trans acids (<5 wt %). The fat compositions obtained can be used as fat replacer with a number of benefits such as providing good textural properties to the food, while not raising the LDL-cholesterol levels in the blood serum. When considering example 5, in particular table 3 of this patent application one must conclude that good product performance is only obtained if the fat applied contains about 12 wt % PSA. Products based on fats without PSA perform badly (=control fat 1). Fats with only small amounts PSA are still grainy, while using a fat with a high content of PSA (=fat 4 with about 64 wt % PSA via the coriander oil) has a poor overall appearance. Food products that are indicated are margarines, dressings, confections, spreads, frozen desserts, ice cream, mayonnaise, mustards, cheese, dip sauces, bread, biscuit, dairy products, frying oils, CBE's, candy, meat, egg products, nut products, vegetable or fruit products, toppings, creams, puddings, cookies, pastries, pies, crackers, cakes, bread rolls and ingredients or premixes herefore. As PSA is the active ingredient that provides the health benefits to the food product there is a big need to be able to use fats with high levels of PSA but that perform well when applied in food products. Ie the appearance of the food products should be good as well.
Inflammation is a key problem in a number of disease states. Extensive scientific research has focused on identifying compounds that have anti-inflammatory activity. So far the main treaments are synthetic compounds in the pharmaceutical area or complex mixtures of compounds, synthetic or natural. It is known that fish oils can be used to some extent as an anti-inflammatory. However, fish oils have the disadvantage of being very unstable and of forming off tastes very easily. Therefore the use of products based on fish oils as anti-inflammatory compositions has not found wide commercial application within the public domain.
U.S. Pat. No. 4,918,063 (1990) discloses that some specific inflammatory diseases such as peptic ulcer disease or inflammatory bowel disease can be prevented or treated with mixtures of saturated or unsaturated phospholipids and saturated or unsaturated triglycerides and/or sterols. The activity of these mixtures is attributed to the fact that these mixtures have the ability to increase or maintain its hydrophobic character by treating the luminal surface of the gastrointestinal tract. It is expressly disclosed that the use of unsaturated phospholipids per se does not work. These compounds only can work in the presence of a triglyceride or sterol. This thus leads away from using unsaturated derivatives of fatty acids for the purposes mentioned in this document. No examples are given for the use of petroselinic acid or glycerides containing this. The only indication herefore can be found in a listing in table 1.
The teaching laid down in the above U.S. 063 is confirmed by U.S. Pat. No. 5,178,873, wherein a method for inhibiting phospholipase A2 activity is disclosed by using stearidionic acid or a C20:4 unsaturated fatty acid. In the Tables 2 and 3 it is demonstrated in a comparative example that petroselinic acid is not useful for this purpose.
Another well recognized consumer problem is formed by the aging of the skin. In recent years the demand for methods to improve the appearance of skin and, in particular, for reducing or preventing the visible signs of wrinkled, aged and/or photodamaged skin has grown enormously. It is known in the art that the levels of collagen, a dermal structural protein and decorin, a structuring proteoglycan in skin are significantly reduced with aged and/or photodamaged skin (Lavker et al J.Inv.Derm.1979 73:79-66, Bernstein et al Lab. Invest. 1995 72:662-669). The reduction in these proteins is associated with a decrease in the tensile strength of the skin causing wrinkles and laxity.
Extensive research has focused on identifying actives that have anti-aging activity. One of the main current actives is retinoic acid, giving wrinkle effacement and dermal repair through boosting for example by collagen synthesis (e.g. Griffiths et al. N. Eng. J. med. 1993 329:530-535). According to GB 2 181 349 another solution was found in the use of triglycerides derived from long chain polyunsaturated fatty acids in cosmetic or dermatological compositions. These compositions are thus not edible in general because they also will contain non edible components. Moreover the triglycerides derived from these polyunsaturated fatty acids are unstable in particular with respect to oxygen stability.
We studied whether we could find a natural component that could be used as anti-inflammatory agent without creating problems of side effects and not having the negative aspects from fish oils, and other known anti-inflammatory compositions.
We also studied whether we could find a natural component that could be used as anti-aging agent without creating problems of side effects and not having the negative aspects from the known anti-aging compositions.
We further studied whether we could find fat compositions that combine high PSA levels with a very good product performance.
The study on anti-inflammatory and antiaging activity resulted in our finding that petroselinic acid derivatives (ie free fatty acid, short alkyl ester, short being C1-C4, wax-esters, mono-di- or triglycerides) can be applied as firstly anti-inflammatory agents that act on the formation of metabolites from arachidonic acid (a recognised precursor of inflammatory mediators), or that can reduce the formation of intracellular adhesion molecules, and thus contribute to the inflammatory response. Or secondly can be applied as an anti-aging agent that act by boosting the levels of two structural proteins in the dermis of the skin, collagen and decorin. Moreover we found novel fat compositions that combine high PSA levels with good product performance.
BRIEF SUMMARY OF THE INVENTION
Therefore our invention concerns in the first instance the use of edible compositions containing petroselinic acid for the preparation of functional food compositions or food supplements, wherein the composition containing petroselinic acid is used as an anti-inflammatory component that inhibits the production of metabolites of arachidonic acid and/or reduces the formation of intracellular adhesion molecules.
Our invention further concerns the use of edible compositions containing petroselinic acid for the preparation of functional food compositions or food supplements, wherein the composition containing petroselinic acid is used as an anti-aging component that boosts decorin levels with a positive impact on skin conditions selected from the group consisting of wrinkling, sagging, photodamaged skin, dry skin, flaky skin and age spots.
Functional food compositions being defined as food compositions containing at least one component with a health benefit. Food supplements being defined as compositions that are not used as food per se, but that are used as supplement to the daily food intake, in general in the form of encapsulated essential food ingredients. These edible compositions containing petroselinic acid can be applied in many different forms, but we prefer to apply these compositions as a composition comprising 5-99.9 wt % of fat or fat blend.
The fats that can be used in the compositions containing the petroselinic acid derivative can be selected from the group consisting of: cocoa butter equivalents, palm oil or fractions thereof, palm kernel oil or fracti

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