WO2010019598A1

WO2010019598A1 - Diacylglycerol rich fats, oils and functional foods

Info

Publication number: WO2010019598A1
Application number: PCT/US2009/053442
Authority: WO
Inventors: Ganesh Kishore
Original assignee: Abunda, Inc.
Priority date: 2008-08-11
Filing date: 2009-08-11
Publication date: 2010-02-18
Also published as: KR20110049868A; MX2011001673A; BRPI0917949A2; CN102176834A; EP2323497A1; CA2733569A1

Abstract

Disclosed is a fat or oil useful for cooking applications which includes from 10 to 90 % DAG, and comprises at least 15% solids at room temperature; in particular embodiments, the fat or oil is derived from palm oil, palm kernel oil, coconut oil, sunflower oil, soybean oil, corn oil, rapeseed oil, grape seed oil, rice bran oil, sesame oil, and peanut oil, or any combination thereof, and exhibits health benefits including lowered serum LDL, raised serum HDL, lowered total serum cholesterol, reduced risk of metabolic syndrome, reduced risk of diabetes mellitus, enhanced fetal health, enhanced insulin sensitivity, reduced risk of hypertension, and enhanced resistance to obesity per unit of consumption. Food compositions and methods of health enhancement utilising the fats and oils of the invention are also disclosed.

Description

DIACYLGLYCEROL RICH FATS, OILS AND FUNCTIONAL FOODS

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] The present application claims priority to U.S. Prov. App. Ser. No. 61/087,926 (filed August 1 1 , 2008) and U.S. Prov. App. Ser. No. 61/087,991 (filed August 11 , 2008), each of which are incorporated herein by reference in their entirety.

STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR

DEVELOPMENT

[0002] Not Applicable.

INCORPORATION-BY-REFERENCE OF MATERIAL SUBMITTED ON A COMPACT

DISC

[0003] Not Applicable.

FIELD

[0004] The present teachings relate to compositions and methods for making and using health-promoting diacylglycerol-rich semi-solid fats and oils as functional foods, derived from palm and other tropical vegetable oils, which may be combined with sunflower, soy, corn, rapeseed and other temperate vegetable oils of high palmitic and/or high stearic acid content, for cooking use, as well as in food preparations, medicinal supplements, pharmaceuticals, cosmetics and other relevant applications. The semi-solid fats and oils can comprise both 1 ,2 and 1 ,3 diacylglycerol molecules, and can comprise fatty acids of chain lengths comprising between 8-22 carbons. The fatty acids can comprise saturated or partially saturated fatty acids. The semi-solid fats and oils can be derived from any source, and the diacylglycerol molecules can be obtained using any known methods.

INTRODUCTION

[0005] There is an urgent demand in many food sectors to find replacements for trans fats. Trans fats are industrially created by partially hydrogenating plant oils to create more saturated, higher melting point solid fats. Trans fatty acids ("TFAs") are produced when oils and fats containing unsaturated fatty acids are "hydrogenated" in the presence of a catalyst. Hydrogenation primarily increases the melting range of the unsaturated fats and thereby enables their incorporation into many solid fat formulations. When an unsaturated fat or oil is fully hydrogenated, all the unsaturated fatty acids are converted into their saturated analogues. Since unsaturation in most vegetable oils is largely 18-carbon fatty acids, namely oleic (18:1 , n-9), linoleic (18:2, n-6) and linolenic (18:3, n-3), full hydrogenation of such oils would result in a stearic acid (18:0), high melting block of fat. Partial hydrogenation, in the presence of catalysts, results in the formation of TFA. These are the geometrical isomers of unsaturated fatty acids containing at least one double bond in the trans configuration. This trans configuration imparts physical properties including reduced fluidity of the fat, thereby increasing its melting point. Thus, partial hydrogenation of liquid oils has been a tool of choice to enable their use in solid fat formulations These trans fats are used for applications such as deep frying and baking, while extending the shelf life of products of these processes. TFAs are widely distributed in foods containing traditional margarine, bakery and frying fats, vegetable shortenings, and vanaspati.

[0006] Since their introduction into the human diet and until the early 1990s, partially hydrogenated fats containing TFA were advocated as the preferred fatty acid base for solid fats, especially margarines. They were initially designed to replace butterfat, and with advancements in our knowledge about the adverse impacts of saturated fatty acids ("SFA") on cardiovascular disease ("CVD") risk, TFAs were prominently touted as a safe alternative However, health authorities worldwide, in particular the FDA, have recently recommended that consumption of trans fats be reduced to zero or to trace amounts due to their ability to increase coronary heart disease by raising levels of "bad" low-density lipoprotein (¹LDL") cholesterol and lowering "good" high-density lipoprotein ("HDL") cholesterol. A study of Mensink and Katan suggested that TFA increased total and LDL cholesterol and decreased the beneficial HDL cholesterol following the consumption of a high-TFA diet Repeatedly, studies have established that TFA diets could be worse than the SFA-rich diets they were designed to replace. A Nurses Health Study elucidated the effects of a TFA diet using epidemiological data from 85,095 women, establishing an association between TFA and the incidence of non-fatal myocardial infarction from coronary heart disease ("CHD"). A positive and significant association between TFA and CHD was apparent Foods that were major sources of TFA, including margarine and cookies, also revealed a positive correlation. Relative risk for CVD was increased by 27% as a result of TFA consumption. Other studies showed adverse effects of TFAs on serum markers of inflammation, including related enzymatic activity, and immune function. See Baer DJ, Judd JT, Clevidence BA, et al. Dietary fatty acids affect plasma markers of inflammation in healthy men fed controlled diets: a randomized crossover study, Am J CIm Nutr 2004;79:969-73; de Roos NM, Schouten EG, Scheek LM, et al Replacement of dietary saturated fat with trans fat reduces serum paraoxonase activity in healthy men and women, Metabolism 2002; 12: 1534-7; and Han SN, Leka LS, Lichtenstein AH, et al. Effect of hydrogenated and saturated, relative to polyunsaturated, fat on immune and inflammatory responses of adults with moderate hypercholesterolemia. J Lipid Res 2002;43:445-52 These studies established a clear association of TFA consumption with increased incidence and death from CVD It was estimated that almost 80,000 deaths in the US alone were associated with continued consumption of foods rich in TFA. Other recent studies have implicated TFA-rich diets with increased risk and incidence of diabetes. Other concerns include adverse effects of TFA on cardiac arrhythmia and underlying implications for the health of the developing fetus since TFA competes with essential fatty acids during fetal development.

[0007 ] Natural palm oil comes from the fruit of the oil palm tree, a tropical species that originated in West Africa, but now several varieties are grown in many parts of the world. Palm and other tropical oils have useful properties for applications in place of trans fats. In addition to being relatively inexpensive, palm oil is semi-solid at room temperature, making it an oil well-suited for baking and food production. However, there is a strong perception that its high saturated fat content (50% for palm oil, 80% for palm kernel oil) is undesirable at a time when health agencies in the US and Europe, in particular, are trying to educate consumers about the need to lower daily intake of saturated fats. Reformulated solid fats should not contain increased contents of SFA. A primary consideration in the food industry today is to count the sum of TFA and SFA as "cholesterol elevating." Thus, a need exists for reformulated solid fats with desirable cooking properties, but with greater health benefits.

SUMMARY

[0008] The present teachings include diacyglycerol ("DAG")-based semisolid fat and oil compositions. [0009] In accordance with an embodiment of this aspect, the DAG-based semi-solid fat and oil compositions can be derived from a plant selected from the group consisting of palm, palm kernel, coconut, other tropical plants, temperate plants and algae.

[0010] In accordance with a further embodiment, the DAG-based semisolid fat and oil compositions can be derived from non-plant sources.

[0011] In a further aspect of the embodiment, the non-plant source can be a fish.

[0012] The present teachings include methods for cooking and food preparation using the DAG-based semi-solid fat and oil compositions of the present disclosure.

[0013] In accordance with a further aspect, foods comprising the DAG- based semi-solid fat and oil compositions are provided.

[0014] In accordance with yet another aspect, cooking fats and oils comprising the DAG-based semi-solid fat and oil compositions are provided.

[0015] In accordance with yet another aspect, methods for managing metabolic syndrome and cardiovascular disorders and/or improving postprandial and fasting blood lipid levels are provided.

[0016] In accordance with an embodiment of the present disclosure, a semi-solid fat or oil comprising DAG derived from a tropical oil is provided.

[0017] In a further aspect of this embodiment, the oil is selected from the group consisting of palm oil, palm kernel oil, coconut oil and other oils, including but not limited to oils with high stearic acid content.

[0018] In a further embodiment, the fat or oil exhibits beneficial health effects when ingested by a mammal.

[0019] In an aspect of this embodiment, the beneficial health effects comprise amelioration of a disease state.

[0020] In a further aspect of this embodiment, the disease state is selected from the group consisting of hyperlipemia, hypercholesteremia, hyperglycemia, insulin resistance, postprandial lipemia, and other aspects of metabolic syndrome. [0021] In a further aspect of this embodiment, the beneficial health effects are selected from the group consisting of lowered serum LDL, raised serum HDL, lowered total serum cholesterol, reduced risk of metabolic syndrome, reduced risk of diabetes, enhanced fetal health, enhanced insulin sensitivity, reduced risk of hypertension, reduction of inflammatory biomarkers related to obesity and enhanced resistance to obesity.

[0022] In some aspects, an inflammatory biomarker related to obesity can be selected from the group consisting of cytokines, C-reactive protein (CRP), interleukin-6 (IL-6), monocyte chemoattractant proteιn-1 (MCP-1 ), tumor necrosis factor alpha (TNF-α), ιnterleukιn-18 (IL-18), ιnterleukιn-10 (IL-10), serum amyloid A (SAA), fibrinogen, intercellular adhesion molecule-1 (ICAM-1 ), lipoprotein-associated phospholipase-A2 (Lp-PLA2), myeloperoxidase, CD40 ligand, osteoprotegerin, P- selectin, and tumor necrosis factor receptor-ll.

[0023] In a further aspect of this embodiment, the beneficial health effects are selected from the group consisting of a reduction in weight of the mammal and a reduction in intracellular inflammatory markers.

[0024] In a further embodiment, a fat or oil as described above may be provided that additionally comprises medium-chain diglyceπdes.

[0025] In an embodiment of the present disclosure, a fat or oil useful for cooking applications comprising from 10 to 90 % DAG, comprising at least 15% solids at room temperature, is provided.

[0026] In an aspect of this embodiment, the fat or oil comprises from 20 to 70% DAG.

[0027] In a further aspect of this embodiment, the fat or oil comprises from 25 to 60% DAG.

[0028] In a further aspect of this embodiment, the fat or oil comprises from 30 to 50% DAG.

[0029] In a further aspect of this embodiment, the fat or oil comprises from 20% to 60% solids at room temperature.

[0030] In a further aspect of this embodiment, the fat or oil comprises from 22% to 50% solids at room temperature. [0031] In a further aspect of this embodiment, the DAG content is derived from a plant selected from the group consisting of palm, palm kernel, coconut, other tropical plants, non-tropical plants, vegetables and algae.

[0032] In a further aspect of this embodiment, the DAG content is derived from an oil selected from the group consisting of palm, palm kernel, coconut and high-stearate vegetable oil, or any combination thereof.

[0033] In a further aspect of this embodiment, the DAG content is derived from palm oil.

[0034] In accordance with a further embodiment, the DAG-based semisolid fat and oil compositions can be derived from non-plant sources.

[0035] In a further aspect of this embodiment, the saturated fat content of the DAG component has been increased from 5 % to 30 % over the parent stock from which the DAG component is derived.

[0036] In a further aspect of this embodiment, the saturated fat content of the DAG component has been increased from 15 % to 30% over the parent stock from which the DAG component is derived.

[0037] In a further aspect of this embodiment, the DAG component of the fat or oil comprises at least 25% 1 ,3-DAG.

[0038] In a further aspect of this embodiment, dietary consumption of the fat or oil, or foods cooked or prepared using said fat or oil, provides one or more of the health benefits selected from the group consisting of lowered serum LDL, raised serum HDL, lowered total serum cholesterol, reduced risk of metabolic syndrome, reduced risk of diabetes, enhanced fetal health, enhanced insulin sensitivity, reduced risk of hypertension, reduction of inflammatory biomarkers related to obesity, and enhanced resistance to obesity per unit of consumption.

[0039] In a further aspect of this embodiment, the fat or oil further comprises one or more of the additional ingredients selected from the group consisting of phytosterol, and phytostanol.

[0040] In a further aspect of this embodiment, the composition further comprises phytosterol.

[0041] In a further embodiment, a food composition is provided that comprises a fat or oil component of any of the above embodiments, wherein the food composition is formulated to comprise one of the foodstuffs selected from the group consisting of shortening, bakery fat, frying fat, cocoa-butter equivalent, cocoa-butter replacer, margarine, and vanaspati.

[0042] In a further aspect of this embodiment, the food composition is formulated to comprise shortening.

[0043] In a further embodiment, a food composition is provided that comprises a prepared food cooked or prepared using the food composition of any of the above embodiments, wherein the food composition is selected from the group consisting of cakes, breads, sweet dough, cream filling, ice cream, granola bars, pastry, non-dairy fats, coating fats, deep fat fries, shortening, coca-butter substitutes, specialty fats and bakery fats.

[0044] In a further aspect of this embodiment, the food composition exhibits one or more of the enhanced characteristics selected from the group consisting of enhanced shelf-stability, enhanced emulsion stability, reduced brittleness, enhanced spreadability, enhanced melt-in-the-mouth sensation, higher melting-point, reduced trans-fatty acid content per unit of solids consumed, reduced PUFA content per unit of solids consumed, reduced susceptibility to oxidation, enhanced texture, enhanced palatability, enhanced lubricity, and enhanced air trapping capacity. In particular, the food composition exhibits one or more of the enhanced characteristics selected from the group consisting of increased palatability, mouth feelings and sensory attributes of non-fat or reduced fat products.

[0045] In a further aspect of this embodiment, the food composition exhibits enhanced shelf-stability.

[0046] In an embodiment of the present disclosure, a method is provided for providing one or more of the health benefits selected from the group consisting of lowered serum LDL, raised serum HDL, lowered total serum cholesterol, reduced risk of metabolic syndrome, reduced risk of diabetes, enhanced fetal health, enhanced insulin sensitivity, reduced risk of hypertension, reduction of inflammatory biomarkers related to obesity and enhanced resistance to obesity per unit of consumption to a subject comprising administering to said subject a food composition in accordance with any of the embodiments above.

[0047] In a further aspect of this embodiment, the health benefit provided comprises reduction of inflammatory biomarkers related to obesity. [0048] In a further aspect, the oils having a high stearic acid content comprise 12% or more stearic acid by weight.

[0049] In a further aspect, the oils having a high stearic acid content are selected from the group consisting of sunflower oil, soybean oil, corn oil, rapeseed oil, grape seed oil, rice bran oil, sesame oil, shea butter, cocoa butter and peanut oil.

[0050] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises 40% - 99% 1 ,3-DAG.

[0051] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises 50% - 95% 1 ,3-DAG.

[0052] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises 60% - 90% 1 ,3-DAG.

[0053] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises at least 70% 1 ,3-DAG.

[0054] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises 40% - 99% 1 ,2-DAG.

[0055] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises 50% - 95% 1 ,2-DAG.

[0056] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises 60% - 90% 1 ,2-DAG.

[0057] In a further aspect of any of these embodiments, the DAG component of the fat or oil comprises at least 70% 1 ,2-DAG.

[0058] In a further embodiment, the DAG comprises SFAs of 8-22 carbons.

[0059] In a further aspect of this embodiment, the DAG comprises SFAs of 8-18 carbons.

[0060] In a further aspect of the embodiment, the SFAs can be derived from any source.

[0061] In a further aspect of this embodiment, the SFAs can be derived from plants selected from the group consisting of soy, sunflower, canola/OSR, shea butter and cocoa butter. [0062] In a further aspect of this embodiment, the SFAs can be derived from a source that has been modified to contain high SFA levels.

[0063] In an additional embodiment, the DAG comprises at least one unsaturated fatty acid at the 1 , 2, or 3 position.

[0064] In a further aspect of this embodiment, the at least one unsaturated fatty acid is selected from the group consisting of an 18:1 , 18:3, 18:4, 20:3, 20:4, 20:5, and 22:6.

[0065] In a further aspect of the embodiment, the at least one unsaturated fatty acid is selected from the group consisting of an omega 3 and an omega 6 fatty acid.

[0066] In a further aspect of any of these embodiments, the unsaturated fatty acids may be derived from any source. Fish, alga and plants are provided as non-limiting examples of a source of unsaturated fatty acids.

[0067] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 15% - 99% SFA.

[0068] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 50% - 99% SFA.

[0069] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 60% - 99% SFA.

[0070] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 70% - 99% SFA.

[0071] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 80% - 99% SFA.

[0072] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 60% - 99% SFA.

[0073] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 15% to 50% SFA.

[0074] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 20% to 50% SFA.

[0075] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 30% to 50% SFA. [0076] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises 40% to 50% SFA.

[0077] In a further aspect of any of these embodiments, the SFA component of the fat or oil comprises at least 15% SFA.

[0078] In a further aspect of these embodiments, the percentage of SFAs is the number of fatty acids which are SFAs divided by the total number of fatty acids, times 100.

[0079] In further aspects of the embodiments, there is provided a food composition which exhibits one or more of the enhanced characteristics selected from the group consisting of to increase palatability, mouth feelings and sensory attributes of non-fat or reduced fat products.

[0080] In further aspects of the embodiments, a semi-solid fat or oil comprising 10 to 90% DAG blended with MUFAs, PUFAs, medium-chain fatty acids and a combination of one or more thereof is provided.

[0081] In a further aspect of the embodiment, the oils and fats blended with the DAG-containing compositions are derived from a source selected from the group consisting of fish, algae, vegetables and any combination thereof.

[0082] In an additional aspect of the embodiment, the oils and fats blended with the DAG-containing compositions are derived from a source selected from the group consisting of palm, coconut, any tropical oils, sunflower, corn, soybean, rapeseed and canola oils.

[0083] In another aspect of the embodiment, the oils and fats blended with the DAG-containing compositions comprise one or more of 18:1 , 18:2, 18:3 (both omega 3 and omega 6), 18:4, 20:3, 20:4, 20:5 and 22:6 omega 3 fatty acids.

[0084] In one embodiment, the oil or fat blended with the DAG-containing compositions comprises gamma-linolenic acid.

[0085] In an additional embodiment, the oil or fat blended with the DAG- containing compositions comprises stearidonic acid.

[0086] These and other features, aspects and advantages of the present teachings will become better understood with reference to the following description, examples and appended claims. DRAWINGS

[0087] Those of skill in the art will understand that the drawings, described below, are for illustrative purposes only. The drawings are not intended to limit the scope of the present teachings in any way.

[0088] Figure 1 is a schematic of the metabolic pathway of DAG vs TAG.

[0089] Figure 2 is a diagram of the chemical structure of a representative 1 ,3 and 1 ,2 diacylglycerol.

[0090] Figure 3 is a graph showing the solid fat index of several compositions at various temperatures.

[0091] Figure 4 is a pictorial representation of a protocol testing beneficial health effects of DAG-containing compounds.

DETAILED DESCRIPTION

[0092] Applicant's DAG-rich oils and fats provide enhanced nutritional value because of their differential metabolism in the body. Additionally, their reduction of saturated fats provides superior health attributes versus saturated fat- containmg oil, e.g., reducing postprandial LDL and triglyceride ("TAG") levels, yet retains the important physical properties of solid fats needed to replace trans fats in foods and cooking fats and oils. These DAG-rich oils retain excellent physical properties for superior domestic and commercial cooking and frying oil, as well as for incorporation into other foodstuffs.

[0093] The DAG-rich fats and oils provided by the applicants provide an important source of energy, essential fatty acids and fat-soluble vitamins; while they impart an excellent flavor, texture, and palatability to food. Moreover, because of their structure and metabolic profile, they are beneficial for managing certain markers of metabolic syndromes such as postprandial hyperlipemia, insulin resistance, LDL and HDL blood levels. See Hidekatsu Yanai, Yoshiharu Tomono, Kumie Ito, Nobuyuki Furutani, Hiroshi Yoshida and Noπo Tada, Diacylglycerol oil for the metabolic syndrome, Nutritional Journal 2007, 6:43 Yanai et al have previously explained the differences between TAG and DAG metabolism. In contrast to TAGs, 1 ,3 and/or 1 ,2 DAG do not completely reassembled after they are digested and absorbed through the intestinal lumen. As illustrated in FIG. 1 , following absorption, the free fatty acids are transferred to the liver and used as a source of energy. [0094 ] Hence, applicant has discovered a fat and oil composition that: (1 ) has a beneficial effect on metabolic syndrome and/or CVD; (2) takes advantage of the superior physical properties of the semi-solid palm and other fat and oil to replace trans fat-containing shortenings and other semi solid fats; and (3) develops a new market segment by providing a palm oil-based composition that features a reduced saturated TAG content.

[0095] In addition, palm kernel oil and coconut oil, among other tropical oils, are rich sources of medium-chain triacylglycerides (MCTs). MCTs can be modified into medium-chain diacylglycerides (MCDs). MCDs s are diacylglycerides with a carbon chain length ranging from 6 to 12. Like other diacylglycerides, MCDs would be expected to be metabolized for energy needs rather than contribute to adiposity when consumed. Applicants' DAG-rich palm and palm kernel-derived oil and fat compositions can be engineered to contain high levels of MCDs. The known effects of medium-chain lipids in triglycerides, in addition to the reduction in LDL accompanying the use of DAGs, will provide health benefits associated with the consumption of the compositions disclosed herein.

[0096] Natural palm oil is approximately 50% SFA (7g in one tablespoon serving) and natural palm kernel oil is approximately 80% SFA (1 Og in one tablespoon serving), and have an approximate DAG content of 4 to 7.5%. Applicants' DAG-rich palm and palm kernel-derived oil and fat compositions have higher DAG content than the parent oil, containing approximately 70% 1 ,3-DAG and 30% 1 ,2- DAG (see FIG. 2 for chemical structures of 1 ,3-DAG and 1 ,2-DAG).

[0097 ] Applicant's DAG-rich palm oil compositions would also be expected to feature an improved shelf life and resistance to becoming stale. The reason for this is that incorporation of DAGs has been shown to improve emulsion stability, and can reduce the rate of formation of compounds that are associated with stale flavors. Incorporation of DAGs reduces water activity in starches and proteins, comprising the food matrix and, consequently, reduces processes leading to the formation of stale flavors. Accordingly, applications of the compositions disclosed herein include a wide variety of uses for which a healthier solid fat profile, improved shelf-life, and staling properties are sought. These include deep fat fries, shortening, and cocoa- butter substitutes in confectionary foods. Additionally, there are more expensive products for which applicant's DAG-rich palm-derived oil and fat compositions are a superior, healthier oil product, including, but not limited to, specialty fats used in confectionary, e.g., cocoa butter equivalent, cocoa butter substitutes, toffee fat, non- dairy fat (e g , for use in ice-cream), cream filling fat, bakery fats (e.g. for use in desserts such as cakes, cheesecakes, pies, pastries, breads, etc ) and general purpose coating fat. These uses are detailed below.

[0098] Deep-frying is an important food preparation and processing method nearly universally practiced. For deep-frying purposes, the oil or fat should have a low polyunsaturated fat ("PLJFA") profile, especially of linolenic acid, which tends to oxidize very rapidly. Commercial frying operations tend to use solid fats rather than liquid oils, primarily to minimize oxidation of the oils and to extend the shelf life of the fried products.

[0099] Shortenings, including bakery fats, are used extensively in the food industry. An important function of a shortening is its ability to incorporate and then hold air when beaten in a cake batter or creamed with sugar. The trapping of air facilitates the formation of a porous structure and increases the volume of the cream and the baked product. Shortenings also contribute to lubrication and give the dough the required final consistency. Such properties cannot be imparted by native liquid oils, which lack the appropriate solids content. Applicant's DAG-rich palm derived, or other DAG-πch, shortenings provide a healthy alternative due to its semisolid physical properties. Shortenings comprising DAG-πch palm oils preferably vary from 10-90%, more preferably 20-70%, still more preferably, 25-60%, and even more preferably from 30-40% DAG-rich palm oil. Applicant's DAG-πch palm oil compositions have 22-25% solids at room temperature, and stabilize the shortening and assist in good baking performance. Among the variety of trans-fat-free cake shortenings possible with DAG-rich palm-based products, are numerous specially designed shortenings for specific applications, such as layer and pound cakes, sweet dough, breads and cream fillers They are also excellent as pastry and bread fats

[0100 ] The above-described foodstuffs, and others containing such DAG- rich ingredients can also be utilized to prepare frozen foods, such as, for example, ice cream, frozen desserts, frozen yogurt and similar products.

[ 0101 ] Margarines are defined as liquid or plastic emulsions containing 80% or more fat, not more than 16% water, and generally fortified with vitamin A. There are several types of margarines, each formulated to fulfill a specific requirement. Applicant's DAG-rich palm-derived oil and fat compositions provide for a superior, healthier margarine than their natural counterparts or the TFA-πch margarines to be replaced They provide good physical properties necessary for quality margarines, including emulsion stability without undue oil separation, reduced brittleness, good spreadability, and a clean, smooth melt in the mouth capability.

[0102 ] Vegetable ghee, or vanaspati, is a major dietary fat source in many developing countries of the Middle East, Indian sub-continent, Afghanistan and South-East Asia. Differences in regional preferences of vanaspati are amplified by the texture of the product ranging from completely smooth to granular, depending on specific culinary practices. Vanaspati is traditionally produced with a range of fat blends, including a very high level of TFA containing hydrogenated fats. Applicant's DAG-rich palm-derived oil and fat compositions may be incorporated as a base ingredient (up to 100%), or as a blend with various soft oils.

[ 0103 ] Compositions disclosed herein can be used in many common household foodstuffs to improve shelf-life, flavor, consistency or beneficial health properties. As non-limiting examples, such a composition can be incorporated into peanut butter, cream cheese, yogurt and/or cookies.

[ 0104 ] "Tropical plants" are coconut, cocoa, shea and palm plants. "Tropical oils," as used herein, refers to oils derived from tropical plants "Temperate plants" are all plants not defined herein as tropical plants. "Oils from temperate plants" and "temperate plant oιl(s)" are oils from temperate plants. "Alga(e)" is construed in the broadest possible sense, to include both unicellular and multicellular photosynthetic organisms, including cyanobacteria.

[ 0105 ] Production of 1 ,3-DAG.

[ 0106] Without limiting as the variety of methods of production available, in the present invention, palm oil, palm kernel oil, coconut oil as well as combinations with other oils, including but not limited to sunflower, corn, soybean, etc, can be modified into diacylglycerides ("DAG") by the removal of one of the fatty acids on the glycerol backbone of the triglyceride parent oil or e.g. by the direct synthesis of diacylglyceral molecules Disclosed are compositions comprising diacylglyceride (DAG) based (semi) solid fats from tropical oils such as palm oil, palm kernel oil and coconut oil and potentially other oils such as sunflower, soybean and corn oil. [0107 ] Diacylglycerols can be synthesized by a variety of methods, including by enzymatic or non-enzymatic means; for example, DAG production can be achieved using lipases. See, e.g., Janni Brogaard Kristensen, Xuebing Xu and Huiling Mu, Diacylglycerol synthesis by enzymatic glycerolysis: Screening of commercially available lipases, J. Amer. Oil Chemists' Society, Vol. 82, No. 5, 2005, p. 329-334. For the production of DAG for an industrial scale, the reuse of the enzyme is advantageous and can be accomplished in a number of ways. Generally, an enzyme can be stabilized by immobilization

[ 0108 ] Both the yield of 1 ,3-DAG and the purity of DAG can be optimized by variations in experimental conditions, including reaction temperature, pressure, and amount of enzyme present. An increase in temperature or the amount of enzyme used can result in an increase in the 1 ,3-DAG production rate. Vacuum is important for attaining high yields of 1 ,3-DAG. Under conditions of a high vacuum (1 mm Hg) at 5O⁰C, 1.09 M 1 ,3-DAG can be produced from 1.29 M glycerol and 2.59 MFA in an 84% yield and in 90% purity (T. Watanabe, et al.). For the lipase- catalyzed synthesis of 1 ,3-DAG, the presence of n-hexane is preferred for the maintenance of lipase activity. In one embodiment of the present invention, the optimum yield (40%) of 1 ,3-DAG synthesis can be obtained when the reaction is carried out with n-hexane/octane (1 :1 , v/v) (H.F.Liao, et al.).

[ 0109 ] Biocatalysed synthesis of sn-1 ,3-dιacylglycerol oil from palm oil, palm kernel oil or potentially other tropical oils, or mixtures thereof, performed in two major steps, without isolation of the intermediates, can be carried out. Ethanolysis of palm oil, palm kernel oil, or potentially, other tropical oils, using immobilized non- regiospecific lipase from Candida antarctica (Novozym 435) can be carried out to obtain glycerol (GIy) and fatty acid ethyl esters (FAEE). In a second step the ethanolysis products can be re-esteπficated using different sn-1 ,3-regiospecιfic lipases, both immobilized and non-immobilized, in different reaction media, that is in the presence of solvents or in a solvent-free system, for different times, at different temperatures (12, 25 and 4O⁰C). The lipase from Rhizomucor miehei (Lipozyme IM) has been the most effective among the sn-1 ,3-specific lipases screened. (F. Blasi, et al). EXAMPLES

[0110] Aspects of the present teachings may be further understood in light of the following examples, which should not be construed as limiting the scope of the present teachings in any way.

[0111 ] In an embodiment, diacylglycerol(s), predominantly 1 ,3 diacylglycerol(s) and 1 ,2 diacylglycerol(s), are administered in combination with other liquid DAG oils and/or solid fats to create favorable metabolic and/or cardiovascular benefits and/or management of postprandial and fasting blood lipid levels.

[0112 ] In an embodiment, semi-solid diacylglycerol(s) DAG, predominantly 1 ,3 diacylglycerol(s) and 1 ,2 diacylglycerol(s), are administered in combination with other liquid DAG oils and/or fats with high stearic acid content, including but not limited to sunflower, corn, soybean, rapeseed, etc., and/or high palmitic content to create favorable metabolic and/or cardiovascular benefits and/or management of postprandial and fasting blood lipid levels.

[ 0113 ] In another embodiment, diacylglycerol(s) (DAG), predominantly 1 ,3- diacylglycerol(s), and phytosterol and/or phytostanol ester(s) combinations, or medium-chain triglycerides, are provided.

[ 0114 ] Another embodiment of the present invention, the composition of matter preferably comprises from 1 to 99 wt% diacylglycerol(s) and from 1 to 99 wt% phytosterol and/or phytostanol ester(s) dissolved or dispersed in edible oil and/or edible fat, and may further optionally comprise monoglycerides.

[ 0115 ] Another embodiment of the present invention provides compositions comprising combinations of diacylglycerol(s), predominantly 1 , 3- diacylglycerol(s), derived from palm oil and palm kernel oil and potentially other tropical oils, in combination with phytosterol and/or phytostanol ester(s) (PSE), dissolved or dispersed in edible oil and/or edible fat, in the manufacture of nutritional supplements and orally administrable pharmaceutical preparations or non-dispersed in an additional edible fat.

[0116] The phytosterol ester(s) in these compositions may be any fatty acid esters, for example but not limited to oleic and palmitic esters of stigmasterol, sitosterol, betasitosterol, brassicasterol, campesterol, 5-avenasterol and isomers and derivatives thereof. [0117 ] In one embodiment of the present invention, a composition comprises a molar ratio between dιacylglycerol(s) and phytosterol and/or phytostanol ester(s), from about 1 : 5 to about 5: 1 In a particular embodiment, the amount of diacylglycerol (s) in a composition is from 1 to 99 wt%, preferably from 7 to 48 wt%, and the amount of phytosterol and/or phytostanol ester(s) in a composition is from 1 to 99 wt%, preferably from 5 to 50 wt%

[ 0118 ] In another embodiment of the present invention, a composition consists of 15 wt% DAG, mainly 1 , 3-dιacylglycerol(s) and 25 wt% total PSE dissolved or dispersed in an edible oil. In a particular embodiment, a composition can consist of 15 wt% DAG, mainly 1 , 3-dιacylglycerol(s) and 25 wt% total phytosterol ester(s) (PSE) dissolved or dispersed in an edible oil.

[ 0119 ] In a pharmaceutical composition of the invention, the molar ratio between diacylglycerol(s) and phytosterol and/or phytostanol, ester(s) is preferably from about 1 5 to about 5:1. In one embodiment, the amount of diacylglycerol(s) in a combination is at least 1 wt%. Further, in the pharmaceutical composition, the amount of phytosterol and/or phytostanol ester(s) in a combination is preferably at least 1 wt%

[ 0120 ] In particular embodiments, the combination comprised in the pharmaceutical composition of the invention, consists of diacylglycerol(s) in an amount of from 1 to 99 wt%, preferably from 7 to 48 wt%, and the amount of phytosterol and/or phytostanol ester(s) in said combination is from 1 to 99 wt%, preferably from 5 to 50 wt%.

[ 0121 ] In other particular embodiments, the pharmaceutical composition of the invention consists substantially of 15 wt% DAG, mainly 1 , 3-dιacylglycerol(s) and 25 wt% total PSE dissolved or dispersed in olive oil.

[ 0122 ] The diacylglycerol(s) may be obtained by any conventional enzymatic or non-enzymatic procedure. They may be obtained by inter-esterification reaction between phytosterol (s) and triglyceride(s) present in the oil and/or fat. The phytosterol and/or phytostanol ester(s) may be obtained by any conventional enzymatic or non-enzymatic procedure.

[ 0123 ] In particular embodiments, the composition of matter according to the invention comprises 1 to 99 wt% diacyglycerols, from 1 to 99 wt% phytosterol and/or phytostanol esters and from 0 to 50 wt% monoglyceπdes and from 1 to 99 wt% triacyglycerol(s) and from 1 to 99 wt% medium-chain triglycerides. More particularly, the composition of matter according to the invention comprises from 3 to 50 wt% diacyglycerols, from 7 to 48 wt % phytosterol and/or phytostanol esters and from 2 to 90 wt% triacyglycerol(s)

EXAMPLE 1

[0124 ] Compositions of the present invention can be used in many common household products to improve shelf-life, flavor, consistency, mouth feel, other sensory attributes or beneficial health properties of low fat and fat-free foods. The following non-limiting examples demonstrate that a Palm DAG composition of the present invention, referred to herein as "Heartlite," can be incorporated into such food stuffs as peanut butter, cream cheese, yogurt, bakery products, granola bars and cookies as described herein

Instructions:

1. Place Peanut Butter in the bowl of a stand mixer fitted with a paddle.

2. Place Heartlite in a microwave safe bowl and melt until liquid.

3. Remove Heartlite from microwave and add to peanut butter.

4. Mix on low speed until peanut butter and Heartlite are completely incorporated.

5. Be sure to scrape the sides of the bowl periodically to be sure the mixture is uniform.

Instructions:

1. Remove lid and foil from cream cheese container.

2. Place cream cheese in microwave for 15 seconds to warm slightly.

3. Weigh cream cheese in bowl of a stand mixer fitted with a paddle.

4. Place measured Heartlite in a microwavable bowl and heat in microwave until liquid.

5. Stir Heartlite with a fork until it returns to its white color and begins to solidify.

6. While mixer is running on slow speed slowly add Heartlite to cream cheese.

7. Continue to mix until cream cheese mixture is uniform and Heartlite has cooled.

Instructions:

1. Soften butter until room temperature. Place butter in the bowl of a stand mixer fitted with a paddle.

2. Place Heartlite in a microwave safe bowl and melt until liquid.

3. Remove Heartlite from microwave and stir until it becomes the consistency of whipped frosting.

4. Add the Heartlite to the softened butter and mix on low speed until creamed.

Instructions:

1. Place the measured yogurt in a blender and blend on low speed just long enough to be sure yogurt is circulating well.

2. Place Heartlite in a microwavable dish and microwave until liquid.

3. Remove Heartlite from microwave and allow to come up to temperature slightly. Do not let the Heartlite solidify.

4. Stream melted Heartlite into blender while mixing on high speed.

5. After all of the Heartlite has been incorporated be sure to scrape the sides and lid of the blender. Return blender to high speed and mix another 45 seconds.

Chocolate Chip Cookie

Recipe adapted from The Bakers' Manual

Revised Third Edition

By: Joseph Amendola

Oven: Convection-Fan on Low-Preheated to 300⁰F Instructions:

1. Place the sugar, butter, molasses, and salt in a mixing bowl. Using a stand mixer fitted with a paddle, cream ingredients until light and fluffy.

2. Melt Heartlite in microwave until liquid. Remove from microwave and stir constantly until Heartlite becomes the consistency of softened butter.

3. Dissolve baking soda in water. Set aside.

4. Slowly stream the eggs, and water and baking soda into the creamed butter mixture. After liquid is incorporated stop machine and scrape bowl. Return to low speed and mix for 30 more seconds.

5. Sift flour and vannilin.

6. Stop mixer, add flour, chocolate chips, and vannilin. Mix on low just until combined.

7. Bake for 8-10 minutes rotating cookies after 4 minutes. Cake Recipe: Test of Recipe Including Buttermilk to Increase Richness

Recipe from The Professional Chef

Seventh Edition

Culinary Institute of America

Oven: Convection-Fan on Low-Preheated to 300⁰F Instructions

1. Place sugars, salt, and softenened butter in bowl of stand mixer fitted with a paddle.

2. Cream sugar mixture on medium speed until light and fluffy.

*3. Melt Heartlite in microwave until completely liquid. Remove from microwave and stir constantly until Heartlite becomes the texture of whipped frosting.

4. Add Heartlite to creamed butter/sugar mixture and continue mixing until Heartlite is incorporated and mixture is again light and fluffy.

6. While mixer is on low speed slowly add eggs, pear puree, and buttermilk. Scrape the bowl and mix again making sure the batter is uniform.

7. Sift vanillin, flour and baking soda.

8. Add sifted flour mixture to batter and stir just until combined.

9. Fill cupcake tins (lined with parchment liners) 2/3 full and bake at 300⁰F for 12-15 minutes or until done.

* Directions for samples including Heartlite only

Notes: Batter was portioned into cupcake tins lined with parchment liners and baked for 15 minutes. Cupcake tins were rotated half way through baking. Each sample was baked individually Carrot Muffin

Recipe adapted from The Professional Chef

Revised Seventh Edition

By Culinary Institute of America

Oven: Convection-Fan on Low-Preheated to 325°F Instructions:

1. Peel, core and quarter apples. Peel carrots.

2. Using a robocoup fitted with a shredder attachment, shred apples and carrots. Set aside.

3. Sift flours, cinnamon, cloves, and baking soda into a large mixing bowl. Add Rice Krispies to sifted ingredients.

4. Place sugar, salt, and oil in bowl of a stand mixer fitted with a paddle.

*5. Melt Heartlite in microwave until liquid. Constantly stir the Heartlite until the fat solidifies and becomes the consistency of whipped frosting.

6. Cream the Heartlite, sugar, oil and salt.

7. Slowly add egg and vanilla to creamed Heartlite. Be sure to scrape sides of the bowl as necessary.

8. Add shredded apples and carrots to egg mixture.

9. Stir in milk until incorporated.

10. Add sifted ingredients and stir just until incorporated.

1 1. Portion 2 oz of batter into muffin tins lined with paper liners and bake for 15 minutes or until done. Granola Bar

Recipe adapted from The Breakfast Book

By: Marion Cunningham

Oven: Convection-Fan on Low-Preheated to 300°F

Instructions:

1. Place shortening, sugars and salt in a bowl of a stand mixer fitted with a paddle and mix until smooth and blended.

*2. Melt Heartlite in microwave until liquid. Constantly stir the Heartlite until the fat solidifies and becomes the texture of whipped frosting.

3. Add Heartlite to shortening mixture and cream until uniformly mixed.

4. Sift flour and baking soda into a medium mixing bowl. Add oats and All-Bran. Be sure all ingredients are well incorporated.

5. Slightly beat eggs in a small mixing bowl.

6. Slowly add coffee and eggs to creamed butter mixture. Be sure to scrape the sides of the bowl until all ingredients are uniformly incorporated.

7. Add dry ingredients and stir until just incorporated.

8. Grease and flour 3 half hotel pans.

9. Press batter onto prepared pans.

10. Bake for 10 minutes, rotate pans, and return to oven for 10 more minutes or until done.

Granola Bar

Recipe adapted from The Breakfast Book

By: Marion Cunningham

Oven: Convection-Fan on Low-Preheated to 300^DF

Instructions:

3. Add Heartlite to shortening mixture and cream until uniformly mixed.

4. Sift flour, and baking soda into a medium mixing bowl. Add oats and All-Bran. Be sure all ingredients are well incorporated.

5. Slightly beat eggs in a small mixing bowl.

7. Add dry ingredients and stir until just incorporated.

8. Grease and flour 3 half hotel pans.

9. Press batter onto prepared pans.

EXAMPLE 2

[0125] The inventors determine whether a diet that includes 15 g/day of the palm or palm kernel DAG fat improves the lipid and lipoprotein profile in moderately hypercholesterolemic individuals when compared to the parent fat (palm or palm kernel) (FIG. 4).

[0126] Individuals (n=20) with moderately elevated or elevated (see below) LDL cholesterol and triglycerides are recruited for a controlled feeding study. The study is a randomized, 2-period, blinded cross-over design (see diagram below). During the entire study both groups eat a control background diet and all foods are provided for the feeding periods. During each treatment period of 4 weeks, the different fats will be incorporated into recipes (i.e. spreads, peanut butter, cream cheese) according to the diet group, Palm Oil (PO) or Palm Oil DAG (POD). Participants have blood drawn and weight and blood pressure (BP) checked at the beginning of the study and at the end of each diet period, on two consecutive days. If there is a break of more than 2 weeks before the start of the second diet period, an additional blood draw is done to establish a baseline. Samples are assayed for lipid profile with aliquots reserved for additional assays (inflammatory markers) if determined to be appropriate.

[0127 ] Participants are healthy men and women, 30-60 years of age, with moderately elevated LDL-C (120-175 mg/dL) or elevated LDL-C (> 175 img/dL) and with HDL-C of 30-50 mg/dL and triglycerides of 120-350 mg/dL. For this study, participants who, by Harris-Benedict equation, will require a total calorie level/day of 2100-3000 are selected. This will allow for one dose of the test fat at 15-20 g for all participants. Subjects are excluded if they are smokers, have diabetes, are pregnant or expecting to be pregnant, or lactating in the last 6 months. Those people who are taking cholesterol-lowering medications, including statins (although it is recognized that statins would not affect the outcome for a particular person) are excluded. Blood pressure lowering medications are acceptable if the person has controlled BP, <140/90 mmHg.

[0128] Diet Design: The background control diet is designed to meet current dietary recommendations - high in fruits and vegetables, whole grains, low- fat dairy, and lean meats. The macronutrient profile is: 25-32% total fat, 15-18% protein, -55% CHO, with 10g/1000 kcal fiber/day and dietary cholesterol < 300 mg/day. The test diets provide <10% of calories from saturated fat from all sources, including the test fats. The 15 g test fat dose is set for the 2100-2400 kcal level. For the 15 g PO or POD diet, 15 of the POD fat for 15 g of the parent fat is substituted. This approach controls for all other sources of fat so that the effects of DAG fat vs. the parent fat are tested specifically. Each day, with meals or as part of a snack, the participant has DAG or parent fat-containing products to eat - that serve as the "vehicle" to provide the fat "dose". Participants receive all of their food for each of the 2 four-week periods. Food is made or purchased and packed for participants by Diet Center Staff. Participants come to the Diet Center five times per week (Monday through Friday), eat one their meals of choice (under supervision), and take other meals/snacks that are packed for them to eat at a time and place of convenience. Meals for the weekend are packed out for consumption at home. Participants are instructed not to eat other foods. Dietary compliance checks will be done daily via questionnaire.

[0129 ] Primary endpoints are of the study are lipids and lipoprotein profile (TC, LDL-C, HDL-C, TG) (FIG. 4).

[ 0130 ] Data Analysis: Data is analyzed based on differences between the control, parent fat and the test fat. Standard methodology is employed to evaluate significant differences between the treatments for the endpoints and correlations between the various endpoints.

EXAMPLE 3

[ 0131 ] The Palm DAG and Palm Kernel DAG of the present invention were subject to compositional analysis.

[ 0132 ] General analytical methods for these analyses are as described in the American Oil Chemists' Society (AOCS) Methods, 4^th Edition (1990).

[0133 ] Appearance was assessed.

[ 0134 ] Moisture was assessed by a Karl-fisher test. A Karl-fisher test is a standard titration that quantifies trace amounts of moisture in a sample.

[ 0135 ] Free fatty acids were determined by the Ca 5a-40 method, as defined by the AOCS The peroxide value was determined by the Cd 8-53 method, also defined by the AOCS. [0136] Positional analysis of fatty acid compositions was determined by pancreatic hydrolysis with sn-1 ,3 specific lipases.

[ 0137 ] To analyze sn-2 monoacylglycerides (MAGs), sn-1 ,3 positional fatty acids were detached from the glycerol backbone by enzymatic reaction sn-1 , 3 specific lipases. A reaction mixture containing sn-2 MAGs and the free fatty acids (FFAs) from the sn-1 ,3 lipase reaction was separated by thin-layer chromatography (TLC). sn-2 MAGs were collected from the TLC plate and analyzed by gas chromatography (GC) according to AOCS protocols for fatty acid composition.

[ 0138 ] Glyceride composition was also analyzed. To separate TAGs, 1 ,3- diacylglycerides, 1 ,2-diacylglycerides, MAGs and FFAs, high pressure liquid chromatography (HPLC) was carried out with an evaporative light scattering detector (ELSD). The results from this analysis were recalculated to present each glyceride as a percentage of the complete composition, based on a standard curve.

[ 0139 ] An SFA content in sn-2 MAGs of 28.8% was obtained as previously described.

[ 0140 ] The analysis was performed on an Agilent 1 100 HPLC system. The column was an Alltima Silica 5u (250 mm x 4.6 mm, 5μL, by Alltech). The detector was an Alltech ELSD, and the analytical software was Chemstations.

Table 1 : Fatty acid composition of Palm DAG

^*fatty acids are expressed in area %

Table 2: Fatty acid composition of Palm Kernel DAG

EXAMPLE 4

[0141 ] The solid fat index of the Palm Kernel DAG, unmodified palm kernel oil and unmodified palm oil were determined across a range of temperatures using a method based on AOCS Cd 10-57 (with modifications). The method can be used with oils and fats with a solid fat index of 50 or less at 10 ⁰C. The method can be used with margarine oils, shortenings, hydrogenated base stocks and other fats.

[0142 ] The method used to determine solid fat index empirically determines the melting profile of a fat under the conditions of the test. Solid fat index is calculated from the specific volumes associated with combined liquid and solid phases at specified temperatures, utilizing a calculated fat expansion/dilation in ml/kg of sample. [0143 ] FIG. 3 shows in graphical form the data presented below in Tables 3-5. The y-axis shows the solid fat index of each of the three compositions. Temperature is plotted on the x-axis.

Table 3: Solid Fat Index of Palm Kernel DAG at various temperatures

Table 4: Solid Fat Index of Palm Kernel Oil at various temperatures

Table 5: Solid Fat Index of Palm Oil at various temperatures

[0144 ] The data above in Tables 3-5 and in Figure 3 show that the Palm Kernel DAG composition disclosed herein has a favorable solid fat index compared to the control fats.

[ 0145 ] The solid fat index of the Palm Kernel DAG makes the DAG composition more useful for incorporation into foodstuffs than alternative fats currently in use. The Palm Kernel DAG composition has a preferable solid fat index when compared to alternative fats. This solid fat index profile allows use of less of the DAG composition to achieve the same texture as alternative fats.

[ 0146] The Palm Kernel DAG compositions of the present disclosure have a flatter solid fat index profile than other fats presently used in cooking. This flatter solid fat index profile allows the use of the compositions of the present disclosure in a wider range of temperatures than other fats.

[ 0147 ] The high melting point of the DAG composition can be useful in the creation or storage of foodstuffs that contain fat. Traditional compositions of many fat-containing foodstuffs can melt or become off-textured when prepared or stored at higher temperatures. Such "higher" temperatures may be only slightly "higher" than standard room temperature of approximately 25 ⁰ C. Foodstuffs prepared with the DAG compositions of the present disclosure have an improved ability to be prepared at these "higher" temperatures as well as an enhanced shelf-life at such temperatures. [0148] The Palm Kernel DAG compositions of the present disclosure have a higher solid fat index at lower temperatures, and a lower solid fat index at higher temperatures. This combination of attributes allows use of the Palm Kernel DAG in shelf-stable foodstuffs, and simultaneously imparts a favorable melt-in-the-mouth texture when consumed. The low melting point (exemplified by a solid fat index of only slightly greater than O at only 40 ⁰C, Table 3) also allows more facile incorporation of the Palm Kernel DAG composition into foods, as it is easily fully melted.

EXAMPLE 5

[0149] Additional compositions of DAG-containing fats and oils are provided.

[0150] In one embodiment, DAG derived from palm oil is provided. The DAG can be 1 ,3-DAG or 1 ,2-DAG. The DAG can comprise from 15% to 99% SFAs. The DAG can comprise fatty acids selected from the group consisting of MUFAs, PUFAs, medium-chain fatty acids and a combination thereof.

[0151 ] In another embodiment, DAG derived from palm kernel oil is provided. The DAG can be 1 ,3-DAG or 1 ,2-DAG. The DAG can comprise from 15% to 99% SFAs. The DAG can comprise fatty acids selected from the group consisting of MUFAs, PUFAs, medium-chain fatty acids and a combination thereof.

[ 0152 ] In another embodiment, DAG derived from an oil from a tropical plant is provided. The DAG can be 1 ,3-DAG or 1 ,2-DAG. The DAG can comprise from 15% to 99% SFAs. The DAG can comprise fatty acids selected from the group consisting of MUFAs, PUFAs, medium-chain fatty acids and a combination thereof.

[0153] In a further embodiment, DAG derived from an oil derived from a temperate plant is provided. The DAG can be 1 ,3-DAG or 1 ,2-DAG. The DAG can comprise from 15% to 99% SFAs. The DAG can comprise fatty acids selected from the group consisting of MUFAs, PUFAs, medium-chain fatty acids and a combination thereof.

[0154 ] In an additional embodiment, DAG derived from an oil derived from an alga is provided. The DAG can be 1 ,3-DAG or 1 ,2-DAG. The DAG can comprise from 15% to 99% SFAs. The DAG can comprise fatty acids selected from the group consisting of MUFAs, PLJFAs, medium-chain fatty acids and a combination thereof.

[0155 ] Compositions of the present invention include 1 ,2-DAG and 1 ,3- DAG where at the 1 (3) and 2 positions, or at both the 1 ,2 and 1 ,3 positions can be SFAs of chain lengths between 8 - 18 carbon atoms. These SFAs can be derived from any source, for example but not limited to palm, coconut, any tropical oils, soy, sunflower and canola oils. Any of these oils can be modified to contain high SFA levels. In addition, the DAG compositions disclosed herein can comprise unsaturated fatty acids such as 18: 1 , 18:2, 18:3 (both omega 3 and omega 6), 18:4, 20:3, 20:4, 20:5 and 22:6 omega 3 fatty acids in the 1 (3) or 2 positions of the DAG. These unsaturated FAs can be derived from any available source including fish, algal, and vegetable oils.

[ 0156] DAG-containing compositions of the present invention can be blended with other oils and/or fats to achieve desirable final compositions. Non- limiting examples of other oils and fats which could be blended with DAG-containing compositions include MUFAs, PUFAs, medium-chain fatty acids and a combination thereof. Oils and fats that can be blended with the DAG-containing compositions can be derived from any available source including fish, algae, and vegetables. Specific non-limiting examples of sources of oils include palm, coconut, any tropical oils, sunflower, corn, soybean, rapeseed and canola oils

[ 0157 ] Specific non-limiting examples of fatty acids that can be included in DAG-containing blends include gamma-linolenic acid (γ-linolenic acid, "GLA") and stearidonic acid. These fatty acids may themselves provide health benefits.

[ 0158 ] GLA is an 18:3 (omega-6) essential fatty acid. It is primarily found in plant-derived oils GLA may be able to suppress tumor growth and metastasis The lithium salt of GLA, Li-GLA, is in phase Il clinical trials to determine whether it is useful in the treatment of HIV infections, since it has the ability to destroy HIV- infected T cells in vitro.

[ 0159 ] Eicosapentaenoic acid (EPA) supplementation has been shown to raise the omega-3 index and to lower risk for cardiac events Stearidonic acid (also called moroctic acid) is an 18:4 (omega-3) essential fatty acid, and has been suggested as a source of omega-3 fatty acid that can raise EPA and/or docosahexaenoic acid (DHA) levels. It is biosynthesized from alpha-linolenic acid by the enzyme delta-6-desaturase. Sources of stearidonic acid include the seed oils of hemp, blackcurrant and echium, and the cyanobacterium spirulma.

[0160 ] The detailed description set forth above is provided to aid those skilled in the art in practicing the present invention. However, the invention described and claimed herein is not to be limited in scope by the specific embodiments herein disclosed because these embodiments are intended as illustrations of several aspects of the invention. Any equivalent embodiments are intended to be within the scope of this invention. Indeed, various modifications of the invention in addition to those shown and described herein will become apparent to those skilled in the art from the foregoing description which do not depart from the spirit or scope of the present inventive discovery. Such modifications are also intended to fall within the scope of the appended claims.

REFERENCES CITED

[0161 ] All publications, patents, patent applications and other references cited in this application are incorporated herein by reference in their entirety for all purposes to the same extent as if each individual publication, patent, patent application or other reference was specifically and individually indicated to be incorporated by reference in its entirety for all purposes. Citation of a reference herein shall not be construed as an admission that such is prior art to the present invention.

Claims

CLAIMS WHAT IS CLAIMED IS

1. A semi-solid fat or oil comprising diacylglycerol ("DAG") derived from a tropical oil.

2. The fat or oil of claim 1 , wherein the oil is selected from the group consisting of palm oil, palm kernel oil, coconut oil and other oils, including but not limited to oils with high stearic acid content.

3. The fat or oil of one of claims 1 and 2, wherein the fat or oil exhibits beneficial health effects when ingested by a mammal.

4. The fat or oil of claim 3, wherein the beneficial health effects comprise amelioration of a disease state.

5. The fat or oil of claim 4, wherein the disease state is selected from the group consisting of hyperlipidemia, hypercholesteremia, hyperglycemia, insulin resistance, postprandial hpemia, and metabolic syndrome.

6. The fat or oil of claim 3, wherein the beneficial health effects are selected from the group consisting of a reduction in weight of the mammal and a reduction in at least one intracellular inflammatory biomarkers of obesity such as cytokines, C- reactive protein (CRP), interleukin-6 (IL-6), monocyte chemoattractant protein-1 (MCP-1 ), tumor necrosis factor alpha (TNF-α), ιnterleukιn-18 (IL-18), ιnterleukιn-10 (IL-10), serum amyloid A (SAA), fibrinogen, intercellular adhesion molecule-1 (ICAM- 1 ), lipoprotein-associated phospholipase-A2 (Lp-PLA2), myeloperoxidase, CD40 ligand, osteoprotegeπn, P-selectin, and tumor necrosis factor receptor-ll.

7. The fat or oil of one of claims 1 and 2, additionally comprising medium-chain diglycerides.

8. A fat or oil useful for cooking applications comprising from 10 to 90 % DAG, comprising at least 15% solids at room temperature..

9. The fat or oil of claim 8 wherein the fat or oil comprises from 20 to 70 % DAG.

10. The fat or oil of claim 8 wherein the fat or oil comprises from 25 to 60 % DAG.

1 1. The fat or oil of claim 8 wherein the fat or oil comprises from 30 to 50% DAG.

12. A fat or oil as set forth in any of claims 8 - 1 1 , wherein the fat or oil comprises from 20% to 60% solids at room temperature.

13. A fat or oil as set forth in claim 12 wherein the fat or oil comprises from 22% to 50% solids at room temperature.

14. A fat or oil as set forth in any of claims 8 - 13 wherein the DAG content is derived from an oil selected from the group consisting of palm, palm kernel, coconut, and high-stearate vegetable oil , or any combination thereof.

15. The fat or oil of claim 14 wherein the DAG content is derived from palm oil.

16. A fat or oil as set forth in any of claims 8 - 15 wherein the saturated fat content of the DAG component has been reduced from 5 % to 30 % over the parent stock from which the DAG component is derived.

17. The fat or oil of claim 16 wherein the saturated fat content of the DAG component has been reduced from 15 % to 30% over the parent stock from which the DAG component is derived.

18. The fat or oil as set forth in any of claims 8 - 17 wherein the DAG component of the fat or oil comprises at least 25% 1 ,3-DAG.

19. A fat or oil as set forth in any of claims 8 - 18 wherein dietary consumption of the fat or oil, or foods cooked or prepared using said fat or oil, provides one or more of the health benefits selected from the group consisting of lowered serum LDL, raised serum HDL, lowered total serum cholesterol, reduced risk of metabolic syndrome, reduced risk of diabetes, enhanced fetal health, enhanced insulin sensitivity, reduced risk of hypertension, reduction of inflammatory biomarkers related to obesity and enhanced resistance to obesity per unit of consumption.

20. The fat or oil of claim 19 wherein the inflammatory biomarker related to obesity comprises one or more of cytokines, C-reactive protein (CRP), interleukin-6 (IL-6), monocyte chemoattractant protein-1 (MCP-1 ), tumor necrosis factor alpha (TNF-α), interleukin-18 (IL-18), interleukin-10 (IL-10), serum amyloid A (SAA), fibrinogen, intercellular adhesion molecule-1 (ICAM-1 ), lipoprotein-associated phospholipase-A2 (Lp-PLA2), myeloperoxidase, CD40 ligand, osteoprotegerin, P-selectin, and tumor necrosis factor receptor-ll.

21. A fat or oil composition as set forth in any of claims 8 - 20, further comprising one or more of the additional ingredients selected from the group consisting of phytosterol and phytostanol .

22. The fat or oil composition of claim 21 wherein the composition further comprises phytosterol.

23. A food composition comprising a fat or oil component as set forth in any of claims 8 - 22, wherein the food composition is formulated to comprise one of the foodstuffs selected from the group consisting of shortening, bakery fat, frying fat, cocoa-butter equivalent, cocoa butter replacer, margarine, and vanaspati.

24. The food composition of claim 23 wherein the food composition is formulated to comprise shortening.

25. A food composition comprising a prepared food cooked or prepared using the food composition of any of claims 23 - 24, wherein the food composition is selected from the group consisting of cakes, breads, sweet dough, cream filling, cream cheese, pastry, non-dairy fats, and coating fats, deep fat fries, coca-butter fats, frozen foods, ice cream, frozen desserts, frozen yogurt, peanut butter, cream cheese, granola, bars, and cookies.

26. The food composition of claim 25 wherein the food composition comprises a cake.

27. A food composition as set forth in any of claims 23 - 26, wherein the food composition exhibits one or more of the enhanced characteristics selected from the group consisting of enhanced shelf-stability, enhanced emulsion stability, reduced brittleness, enhanced spreadability, enhanced melt-in-the-mouth sensation, higher melting-point, reduced trans fatty acid content per unit of solids consumed, reduced PUFA content per unit of solids consumed, reduced susceptibility to oxidation, enhanced texture, enhanced palatability, enhanced lubricity, and enhanced air trapping capacity.

28. The food composition of claim 27 wherein the food composition exhibits enhanced shelf stability

29. A method for providing one or more of the health benefits selected from the group consisting of lowered serum LDL, raised serum HDL, lowered total serum cholesterol, reduced risk of metabolic syndrome, reduced risk of diabetes, enhanced fetal health, enhanced insulin sensitivity, reduced risk of hypertension, reduction of inflammatory biomarkers related to obesity and enhanced resistance to obesity per unit of consumption to a subject comprising administering to said subject a food composition as set forth in any of claims 23 - 28.

30. The method of claim 29 wherein the inflammatory biomarker related to obesity comprises one or more of cytokines, C-reactive protein (CRP), interleukin-6 (IL-6), monocyte chemoattractant protein-1 (MCP-1 ), tumor necrosis factor alpha (TNF-α), interleukin-18 (IL-18), interleukin-10 (IL-10), serum amyloid A (SAA), fibrinogen, intercellular adhesion molecule-1 (ICAM-1 ), lipoprotein-associated phospholipase-A2 (Lp-PLA2), myeloperoxidase, CD40 ligand, osteoprotegerin, P-selectin, and tumor necrosis factor receptor-ll.

31. The fat or oil of claim 2, wherein the oils having a high stearic acid content comprise 12% or more stearic acid by weight.

32. The fat or oil of claim 2, wherein the oils having a high stearic acid content are selected from the group consisting of sunflower oil, soybean oil ,corn oil, rapeseed oil, grape seed oil, rice bran oil, sesame oil, and peanut oil.

33. The fat or oil as set forth in any of claims 8 - 17 wherein the DAG component of the fat or oil comprises 40% - 99% 1 ,3-DAG.

34. The fat or oil as set forth in any of claims 8 - 17 wherein the DAG component of the fat or oil comprises 50% - 95% 1 ,3-DAG.

35. The fat or oil as set forth in any of claims 8 - 17 wherein the DAG component of the fat or oil comprises 60% - 90% 1 ,3-DAG.

36. The fat or oil as set forth in any of claims 8 - 17 wherein the DAG component of the fat or oil comprises at least 70% 1 ,3-DAG.

37. A semi-solid fat or oil comprising 10 to 90% DAG blended with MUFAs, PUFAs, medium-chain fatty acids and a combination of one or more thereof.

38. A fat or oil as set forth in claim 37 wherein the oils and fats blended with the DAG-containing compositions are derived from a source selected from the group consisting of fish, algae, vegetables and any combination thereof.

39. A fat or oil as set forth in claim 38 wherein the oils and fats blended with the DAG-containing compositions are derived from a source selected from the group consisting of palm, coconut, any tropical oils, sunflower, corn, soybean, rapeseed and canola oils.

40. A fat or oil as set forth in claim 37 wherein the oils and fats blended with the DAG-containing compositions comprise one or more of 18 1 , 18:2, 18:3 (both omega 3 and omega 6), 18 4, 20:3, 20:4, 20:5 and 22:6 omega 3 fatty acids.

41. A fat or oil as set forth in claim 37 wherein an oil or fat blended with the DAG- containmg compositions comprises gamma-linolenic acid.

42. A fat or oil as set forth in claim 37 wherein an oil or fat blended with the DAG- containmg compositions comprises stearidonic acid.

43. A fat or oil as set forth in claim 37 wherein the DAG oil comprises 1 ,2-DAG and 1 ,3-DAG wherein at either of the 1 (3) and 2 positions, or at both the 1 ,2 and 1 ,3 positions, the DAG is further comprised of SFAs of chain lengths between 8 - 18 carbon atoms.

44. A fat or oil as set forth in claim 37 wherein the SFAs are derived from the group consisting of palm, coconut, any tropical oil, soy, sunflower and canola oils.

45. A fat or oil as set forth in claim 37 wherein the DAG compositions comprise one or more unsaturated fatty acids comprising 18:1 , 18:2, 18:3 (both omega 3 and omega 6), 18:4, 20:3, 20:4, 20:5 and 22:6 omega 3 fatty acids in the 1 (3) or 2 positions of the DAG.

46. A fat or oil as set forth in claim 37 wherein the DAG compositions comprise gamma-linolenic acid.

47. A fat or oil as set forth in claim 37 wherein the DAG compositions comprise stearidonic acid.

48. A food composition as set forth in any of claims 23 - 27, wherein the food composition exhibits one or more of the enhanced characteristics selected from the group consisting of to increase palatability, mouth feelings and sensory attributes of non-fat or reduced fat products.