Note: Descriptions are shown in the official language in which they were submitted.
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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 11, 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
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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
('LDL")
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
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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 Clin 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 semi-
solid fat and oil compositions.
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[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 semi-
solid 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 hyperlipidemia, hypercholesteremia,
hyperglycemia,
insulin resistance, postprandial lipemia, and other aspects of metabolic
syndrome.
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[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 protein-1 (MCP-1), tumor
necrosis
factor alpha (TNF-a), interleukin-18 (IL-18), interleukin-1 0 (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-II.
[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 diglycerides.
[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.
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[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 semi-
solid 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
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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.
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[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] Ina further embodiment, the DAG comprises SFAs of 8-22 carbons.
[0059] Ina 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.
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[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.
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[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.
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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.
[00891 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-
containing 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 Norio 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.
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[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 (10g 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
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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 ("PUFA") 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-rich, shortenings provide a healthy alternative due to
its semi-
solid physical properties. Shortenings comprising DAG-rich 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-rich 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
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requirement. Applicant's DAG-rich palm-derived oil and fat compositions
provide for
a superior, healthier margarine than their natural counterparts or the TFA-
rich
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 oil(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.
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[01071 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 50 C, 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-diacylglycerol ail 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 (Gly) and fatty acid ethyl esters (FAEE). In a second step the
ethanolysis products can be re-esterificated using different sn-1,3-
regiospecific
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 40 C). The lipase from Rhizomucor miehei (Lipozyme
IM)
has been the most effective among the sn-1,3-specific lipases screened. (F.
Blasi, et
al).
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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.
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[01171 In one embodiment of the present invention, a composition
comprises a molar ratio between diacylglycerol(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 I 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-diacylglycerol(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-diacylglycerol(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-
diacylglycerol(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 I to 99 wt%
phytosterol
and/or phytostanol esters and from 0 to 50 wt% monoglycerides and from 1 to 99
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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 11
[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.
Peanut Butter
Ingredients Amount
Peanut Butter 36 g
Heartlite 5 g
Total 41g
Yield 1 Serving
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.
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Cream Cheese
Ingredients Amount
Cream Cheese 31 g
Heartlite 7 g
Total 38g
Yield 1 Serving
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.
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Butter
Ingredients Amount
Butter 3 g
Heartlite 3 g
Total 6 g
Yield 1 Serving
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.
5. Be sure to scrape the sides of the bowl periodically to be sure the mixture
is
uniform.
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Yogurt
Ingredients Amount
Yogurt 170 g
Heartlite 7 g
Total 177 g
Yield 1 Serving
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.
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Chocolate Chip Cookie
Recipe adapted from The Bakers' Manual
Revised Third Edition
By: Joseph Amendola
Original Recipe A-0% B-0% C-75% D-100%
Heartlite Heartlite Heartlite Heartlite
Ingredient Baking Grams Grams Grams Grams Grams
Measurement
Unsalted 1lb 8oz 680.4 170.0 170.0 42.5 0.0
butter
Heartlite n/a n/a 0.0 0.0 127.6 170.0
Granulated 12oz 340.2 85.1 85.1 85.1 85.1
Sugar
Light 12oz 340.2 85.1 85.1 85.1 85.1
Brown
Sugar
Egg whites 8 oz 226.8 56.7 56.7 56.7 56.7
Butter n/a n/a 0 4 4 4
Extract
Molasses n/a n/a 0 16 16 16
Vanillin To taste 14.2 14 14 14 14
Water 1 oz 28.35 7.1 7.1 7.1 7.1
Baking .5oz 14.2 3.6 3.6 3.6 3.6
Soda
Salt .5oz 14.2 3.6 3.6 3.6 3.6
Pastry 21b 907.2 226.8 226.8 226.8 226.8
Flour
Pear 21b n/a 0 28.4 28.4 28.4
Puree
Chocolate 11b 453.6 113.4 113.4 113.4 113.4
Chips
Total 3019.4 765.4 813.8 813.9 813.8
Oven: Convection-Fan on Low-Preheated to 300 F
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.
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Cake Recipe: Test of Recipe Including Buttermilk to Increase Richness
Recipe from The Professional Chef
Seventh Edition
Culinary Institute of America
Original A-0% B-75% C-100%
Recipe Heartlite Heartlite Heartlite
Ingredient Baking Grams Grams Grams
Measurement
Heartlite 0 0.00 86.25 115.00
Cocoa 40 40 40 40
Powder
Baking Soda 1.5 1.5 1.5 1.5
Salt 1.7 1.7 1.7 1.7
Buttermilk 115 115 28.75 0.00
Sugar 200 200 200 200
Light Brown 115 115 115 115
Sugar
Vanillin 15 15 15 15
Egg whites 110 110 110 110
Buttermilk 226.8 226.8 226.8 226.8
Pear Puree n/a 56.7 56.7 56.7
Cake Flour 140 140 140 140
Total 965 1021.7 1021.7 1021.7
Oven: Convection-Fan on Low-Preheated to 300 F
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 300 F
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.
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Carrot Muffin
Recipe adapted from The Professional Chef
Revised Seventh Edition
By: Culinary Institute of America
Original Recipe A-0% B-75% C-100%
Heartlite Heartlite Heartlite
Ingredient Grams Grams Grams Grams
Cake Flour 317 79.3 79.3 79.3
Whole Wheat Flour 317 79.3 79.3 79.3
Heartlite n/a 0.00 55.1 73.5
Rice Krispies 33 8.3 8.3 8.3
Granulated Sugar 455 113.3 113.3 113.3
Baking Soda 24 6.0 6.0 6.0
Cinnamon, Ground 9 2.3 2.3 2.3
Salt 8 2.0 2.0 2.0
Cloves, Ground 1 0.3 0.3 Ø3
Apples, Grated 686 171.5 171.5 171.5
Carrots, Grated 117 29.3 29.3 29.3
Vegetable Oil 294 73.5 18.4 0.0
2% Milk 116 29.0 29.0 29.0
Pure Vanilla Extract 18 4.5 4.5 4.5
Egg Whites 153 38.3 38.3 38.3
Total 2548 636.9 636.9 636.9
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.
11. Portion 2 oz of batter into muffin tins lined with paper liners and bake
for 15
minutes or until done.
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Granola Bar
Recipe adapted from The Breakfast Book
By: Marion Cunningham
Original Recipe A-0% B-75% C-100%
Heartlite Heartlite Heartlite
Ingredient Grams Grams Grams Grams
Shortening 127.8 127.8 32.9 0.0
Light Brown Sugar 24.0 24.0 24.0 24.0
Granulated Sugar 68 68.0 68.0 68.0
Strong Coffee 56.7 56.7 56.7 56.7
Egg whites 60 60.0 60.0 60.0
Rolled Oats 205 205.0 205.0 205.0
AP Flour 130 130.0 130.0 130.0
Salt 6 6.0 6.0 6.0
Baking Soda 2.5 2.5 2.5 2.5
All-Bran Cereal 93.0 93.0 93.0 93.0
Heartlite n/a 0.0 95.9 127.8
Total 773.0 773.0 678.1 773.0
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.
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Granola Bar
Recipe adapted from The Breakfast Book
By: Marion Cunningham
Original Recipe A-0% B-75% C-100%
Heartlite Heartlite Heartlite
Ingredient Grams Grams Grams Grams
Shortening 127.8 127.8 32.9 0.0
Light Brown Sugar 24.0 24.0 24.0 24.0
Granulated Sugar 68 68.0 68.0 68.0
Strong Coffee 56.7 56.7 56.7 56.7
Egg whites 60 60.0 60.0 60.0
Rolled Oats 205 205.0 205.0 205.0
AP Flour 130 130.0 130.0 130.0
Salt 6 6.0 6.0 6.0
Baking Soda 2.5 2.5 2.5 2.5
All-Bran Cereal 93.0 93.0 93.0 93.0
Heartlite n/a 0.0 95.9 127.8
Total 773.0 773.0 678.1 773.0
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.
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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 and 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 mg/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,
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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, 4th 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.
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[0136] Positional analysis of fatty acid compositions was determined by
pancreatic hydrolysis with sn-1,3 specific lipases.
[01371 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 (H PLC) 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 1100 HPLC system. The
column was an Alltima Silica 5u (250 mm x 4.6 mm, 5pL, by Alltech). The
detector
was an Alltech ELSD, and the analytical software was Chemstations.
Table 1: Fatty acid composition of Palm DAG
Appearance a pale yellow solid
Moisture & Impurities 0.05%
Free Fatty Acid 0.15 mgKOH/g
Peroxide Value 0.2 meq/kg
Typical Fatty Acids Composition*
C14:0 1.3%
C16:0 46.0%
C16:1 0.5%
C18:0 4.3%
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C18:1 35.8%
C18:2 8.8%
C18:3 0.1%
Total USFA (unsaturated fatty acid) 54.2%
Total SFA (saturated fatty acid) 51.5%
Glycerides contents
Tri-acylglyceride (TAG) 10.8%
Di-acylglyceride (DAG) 88.9%
1,3 diglyceride 65.2%
1,2 diglyceride 23.7%
Mono-acylglyceride (MAG) 0.2%
Sn-2 Positional SFA 29.5% (total content included in TAG,
1,2-DAG and 2-MAG)
*fatty acids are expressed in area 0/1
Table 2: Fatty acid composition of Palm Kernel DAG
Appearance a pale yellow solid
Moisture & Impurities 0.05%
Free Fatty Acid 0.14 mgKOH/g
Peroxide Value 0.05 meq/kg
Typical Fatty Acids Composition* Fatty acids are expressed in area %
C8:0 1.1%
C10:0 1.9%
C12:0 47.0%
C14:0 18.3%
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C16:0 9.3%
C16:1 0.1%
C18:0 2.5%
C18:1 16.2%
C18:2 2.2%
Glycerides contents AOCS official method CD 11d-96
Tri-acylglyceride (TAG) 19.8%
Di-acylglyceride (DAG) 80.0%
1,3 diglyceride 57.6%
1,2 diglyceride 22.4%
Mono-acylglyceride (MAG) 0.1%
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 C. 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.
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[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
Temperature Solid Fat Index
C 33.7
21.1 C 24.5
26.7 C 18.6
33.3 C 2.9
40 C 0.4
Table 4: Solid Fat Index of Palm Kernel Oil at various temperatures
Temperature Solid Fat Index
10 C 49.5
21.1 C 34.0
26.7 C 13.0
33.3 C 0.5
40 C 0.4
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Table 5: Solid Fat Index of Palm Oil at various temperatures
Temperature Solid Fat Index
C 37.8
21.1 C 18.1
26.7 C 14.7
33.3 C 12.4
40 C 6.2
[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.
[01451 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 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.
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[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 0 at only 40 C, 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
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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.
[01551 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 (y-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 II 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.
[01591 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
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the enzyme delta-6-desaturase. Sources of stearidonic acid include the seed
oils of
hemp, blackcurrant and echium, and the cyanobacterium spirulina.
[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.
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