Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2001-10-22
2003-08-19
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C435S134000, C554S227000, C514S558000, C514S547000
Reexamination Certificate
active
06608223
ABSTRACT:
FIELD OF INVENTION
The present invention relates to cholesterol lowering structured lipids containing omega 3 polyunsaturated fatty acids and a process thereof.
BACKGROUND AND PRIOR ART REFERENCES
Coconut oil is a kernel oil which is a natural source of medium chain fatty acids (MCFA) (53% of C8:0-C12:0). Its lauric acid content is very high (48%). The lauric fats provide high nutritional value because of their unique position in intercellular transport mechanisms; that is, either the portal or lymphatic systems can absorb them. They provide excellent nutrition for critically ill patients and do not cause any undue coronary difficulties despite their saturation. In fact, the lauric fats provide unexpected usefulness in protein catabolism, yielding positive nitrogen balance and enhanced protein formation. But coconut oil does not contain any omega 3 polyunsaturated fatty acids (PUFA). In addition to this, myristic and palmitic acids that contribute to around 33% of the total fatty acids of coconut oil have been shown to be hypercholesterolemic which is a risk factor for cardiovascular disease.
Medium chain fatty acids comprise fatty acids with 6 to 12 carbon chain lengths. MCFA offer numerous health benefits. They are easily absorbed, transported via the portal system and rapidly metabolized to yield quick energy and is not deposited in the body as fat. Medium chain triglycerides (MCT) have clinical applications in the treatment of fat malabsorption disorders, gall bladder disease, hyperlipidemia, obesity and deficiency of the carnitine system. But MCT alone cannot function as an ideal fat source for humans as they do not provide PUFA.
Omega 3 PUFA like eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have beneficial effects in controlling cardiovascular diseases, immune disorders, inflammation, renal disorders, allergies, diabetes and cancer. These fatty acids are also essential for the development of the brain and retina in humans. Eskimos in Greenland have lower serum cholesterol and triacylglycerol levels and lower incidence of cardiovascular disease owing to the relatively high intake of EPA from their diet. Studies with non-human primates and human new borns suggest that DHA is essential for the normal functioning of the retina and brain, particularly in premature infants. Other studies have shown that n-3 fatty acids can decrease the number and size of tumors and increase the time elapsed before the appearance of tumors.
Metabolically, EPA is an antagonist of the arachidonic acid cascade and competes with arachidonic acid as substrates for cyclooxygenase and lipoxygenase to produce eicosanoids. EPA is used for the synthesis of eicosanoids such as series-3 prostaglandins that ameliorate immunodysfunction. Arachidonic acid forms the series-2 prostaglandins that may impair the immune function. Diets containing high levels of n-6 fatty acids may increase the production of PGE2, decrease IL2 production, alter T cell response to IL2, inhibit macrophage collagenase synthesis, and enhance platelet aggregation. Feeding high levels of omega 3 PUFA will lead to substitution of some arachidonic acid by EPA and DHA. The PGE3 formed from EPA has less inflammatory effect than PGE2. IL 1 production is also lowered by omega 3 PUFA while IL 2 is increased. These changes in eicosanoid synthesis seen with omega 3 PUFA feeding are associated with an improved immunocompetence and a reduced inflammatory response to injury. Patients in need of elemental diets will benefit from having their immunocompetence improved.
Structured lipids are triacylglycerols containing mixtures of short-, medium-, and long-chain fatty acids attached to a glycerol backbone for specific functionality. Structured lipids are formed by the following methods
(a)
hydrolysis and esterification
(b)
interesterification
(c)
lipase-interesterification
(d)
traditional chemical methods
(e)
genetic manipulation.
They are particularly useful because of the way in which they are metabolized. Specific fatty acids can be attached to specific portions of the glycerol backbone to ensure that these fatty acids are absorbed in a specific manner in the digestive process. The process described here finds application in the synthesis of structured lipids designed to impart nutritional and physical benefits.
Cod liver oil is a natural source of EPA (13%) and DHA (8%). A physical blend of MCFA rich triacylglycerols and PUFA rich triacylglycerols does not improve the absorption or metabolism of the fatty acids since each of the individual triacylglycerol maintains its original absorption rates.
Omega 3 PUFA, especially EPA and DHA are generally not found in vegetable oils but can be an acceptable media for providing EPA and DHA from marine sources in the diet. Incorporation of EPA and DHA from fish oil into coconut oil would provide unique specialty oil, eliminate the need for physical mixtures and serve as a single rich source of both omega 3 PUFA and MCFA. One way to achieve this is through lipase-catalyzed reactions. In addition to providing benefits to the immune system, the structured lipid increases the absorption and transport of PUFA by putting both the marine oil and the medium chain triglyceride oil on the same glycerol backbone. Particularly, the structured lipid increases the absorption of eicosapentaenoic acid (EPA, C20:5 omega 3) and docosahexaenoic acid (DHA, C22:6 omega 3). The inclusion of medium and long chain fatty acids on the same glycerol backbone is thought to increase the water solubility of the fatty acids, increase the body's ability to digest the fatty acids, and increase the concentration of fat in the chylomicrons. Thus, the structured lipid aids in absorption, delivery and transport of the fatty acids.
Because of faster absorption, MCT's are useful as a calorie source in the treatment of hospitalized patients. Some hospitalized patients, particularly critically ill patients, have a high risk of infection and require total parenteral nutrition. These patients often have difficulty in obtaining the proper amount of nutrients and energy from the diet; a diet that both minimizes the risk of infection and provides quick nutrition would be of vast benefit to these patients. The changes in eicosanoid synthesis seen with omega 3 PUFA feeding are associated with an improved immunocompetence and a reduced inflammatory response to injury. Patients in need of elemental diets will benefit from having their immunocompetence improved by these structured lipids.
Reference may be made to the article by Lee, K. T and Akoh, C. C., (1996). J. Am. Oil Chem. Soc. 73, 611-615 where, structured lipids were synthesized by interesterification reaction between medium chain triglycerides and EPA ethyl esters. The drawback in this case, is the use of synthetic trilaurin, tricaprin and EPA ethyl esters were used. The effect of these structured lipids on the lipid profile of the body or other physiological effects were also not studied.
U.S. Pat. No. 4,871,768 discloses a synthetic triglyceride comprising a glycerol backbone having three fatty acids attached thereto, said fatty acids being selected from a first group consisting of omega-3 fatty acids, and a second group consisting of caprylic acid, capric acid and mixtures thereof. This patent also discloses a method for minimizing the effects of infection and minimizing the effects of subsequent infection by administering a diet containing 10 to 80% by weight of an oily fraction, said oily fraction being the aforementioned fatty acid. The major drawback in this case too is the use of synthetic trilaurin, tricaprin and EPA ethyl esters. In this case the process for the synthesis is not clear and the synthetic fatty acids used keeps the process at a disadvantage. The lipidemic effects of the product are also not stated.
Reference may also be made to the article by Akoh C. C. Jennings B. H and. Lillard. D. A, (1996) J. Am. Oil Chem. Soc. 72, 1059-1062 who also used EPA ethyl esters to modify evening primrose oil which is a rich source of &ggr;-linolenic acid. The process here
Lokesh Belur Ramaswamy
Rao Reena
Sambaiah Kari
Carr Deborah D.
Council of Scientific and Industrial Research
Merchant & Gould P.C.
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