Note: Descriptions are shown in the official language in which they were submitted.
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NUTRITIONAL COMPOSITION COMPRISING CURCUMINOIDS
AND METHODS OF MANUFACTURE
TECHNICAL FIELD
The present disclosure relates to nutritional compositions, and methods of
making those compositions, comprising a combination of curcuminoids and a
polar
oil.
BACKGROUND
Curcuminoids have been studied over the years for a variety of medical and
nutritional applications. Many of these studies suggest curcuminoids may have
significant anti-oxidant and anti-inflammatory properties and may even inhibit
the
growth of certain types of cancers.
Curcuminoids such as curcumin, demethoxycurcumin (DSMC) and bis-
demethoxycurcumin (BMC) are polyphenols commonly found in Turmeric, a well
known and often used spice derived from rhizome of the herb Curcuma longa
Linn.
These curcuminoids give Turmeric its bright yellow color and are often added
in small
amounts to various nutritional or foods to add color.
There has been considerable effort over the years to formulate nutritional
products comprising curcuminoids at concentrations sufficiently high to
provide the
consumer with health benefits associated with these natural extracts. There
are,
however, several characteristics of curcuminoids that make their formulation
into
such products problematic. Curcuminoids generally have poor bioavailability
when
taken orally, and thus when formulated at higher concentrations to counter
their
inherent poor bioavailability to achieve the desired systemic delivery, the
products
often take on an intense yellow color. This is especially noticeable in
aqueous
emulsions and other liquid nutritional products.
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Moreover, the solubility profile of curcuminoids makes formulation into
nutritional products, especially nutritional products in the form of aqueous
emulsions
or liquids, much more difficult. Curcuminoids have poor solubility in aqueous
systems within the acidic to neutral pH range, a pH range that is common for
many
nutritional liquids or emulsions Curcuminoids are soluble in carriers such as
dimethyl sulfoxide, acetone and ethanol, but are poorly soluble in water as
well as
many types of edible lipids commonly used in the formulation of aqueous
nutritional
emulsions.
Accordingly, there is a need for aqueous and other nutritional compositions,
and methods for preparing these compositions, comprising curcuminoids in an
orally
acceptable vehicle that delivers the desired bioavailability and bioactivity
while
minimizing the impact of the curcuminoids on product color.
SUMMARY OF THE DISCLOSURE
One embodiment is directed to a composition comprising fat, protein, and
carbohydrate, including a combination of curcumin, demethoxycurcumin, and
bisdemethoxycurcumin, which combination is solubilized in a polar oil having
an HLB
value of from about 0.7 to about 14, wherein the weight ratio of the
bisdemethoxycurcumin to the curcumin is from about 1:1 to about 1:7 and the
weight
ratio of the bisdemethoxycurcumin to the demethoxycurcumin is from about 1:1
to
about 1:2.5.
Another embodiment is directed to a composition comprising fat, protein, and
carbohydrate in the form of an aqueous emulsion, wherein the aqueous emulsion
comprises a combination of curcumin, demethoxycurcumin, and
bisdemethoxycurcumin, which combination is solubilized in an oil phase having
at
least one polar oil with an HLB value of from about 0.7 to about 14, wherein
the
weight ratio of the bisdemethoxycurcumin to the curcumin is from about 1:1 to
about
1:7 and the weight ratio of the bisdemethoxycurcumin to the demethoxycurcumin
is
from about 1:1 to about 1:2.5.
Yet another embodiment is directed to a method of making a nutritional
composition comprising the steps of: (a) combining curcuminoids with a polar
oil
having an HLB of from about 0.7 to about 14, wherein said curcuminoids
comprise
curcumin, demethoxycurcumin, and bisdemethoxycurcumin; (b) heating the
combination of curcuminoids and polar oil to a temperature sufficient to
solubilize a
fraction of the curcuminoids in the polar oil; and (c) removing an
unsolubilized
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curcuminoid fraction from the heated combination to form a polar oil having an
HLB
of from about 0.7 to about 14 and comprising a weight ratio of solubilized
bisdemethoxycurcumin to solubilized curcumin of from about 1:1 to about 1:7
and a
weight ratio of bisdemethoxycurcumin to demethoxycurcumin of from about 1:1 to
about 1:2.5; and then (d) formulating the combination of the polar oil and the
solubilized curcuminoid fraction with fat, protein, and carbohydrate to form a
nutritional composition.
It has now been found that curcuminoids can be selectively solubilized in oils
having an HLB of from about 0.7 to about 14 (i.e., polar oils) so that the
resulting
distribution of solubilized curcuminoids in the oil is more bioactive and has
better
bioavailability than natural curcuminoid sources. Moreover, this new
distribution of
solubilized curcuminoids in polar oils has less impact on product color than
natural
curcuminoid distributions, i.e., increased bioactivity and or bioavailability
per unit
color. This new distribution is significantly different than that found in
natural
curcuminoid sources such as Turmeric which most typically contain a curcumin
to
demethoxycurcumin to bisdemethoxycurcumin weight ratio of approximately 10.7
to
2.6 to 1.
DETAILED DESCRIPTION OF THE INVENTION
The compositions and methods herein are directed to nutritional compositions
comprising a shifted distribution of curcuminoids that have been solubilized
in a polar
oil having a defined HLB value. These and other essential or optional elements
or
features of the various embodiments are described in detail hereinafter.
The term "nutritional composition" means the referenced material comprises
fat,
protein, and carbohydrate and is suitable for oral administration to a human.
The
nutritional composition may further comprise vitamins, minerals and other
ingredients
and represent a sole, primary, or supplemental source of nutrition.
All percentages, parts and ratios as used herein are by weight of the total
composition, unless otherwise specified. All such weights as they pertain to
listed
ingredients are based on the active level and, therefore, do not include
solvents or
by-products that may be included in commercially available materials, unless
otherwise specified.
All numerical ranges as used herein, whether or not expressly preceded by the
term "about", are intended and understood to be preceded by that term, unless
otherwise specified.
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The compositions and methods herein may also be free of any optional or other
ingredient or feature described herein, provided that the remaining formula
still
contains the requisite ingredients or features as described herein. In this
context, the
term "free" means the selected composition or method contains or is directed
to less
than a functional amount of the ingredient or feature, typically less than
0.1% by
weight, and also including zero percent by weight, of such ingredient or
feature.
Numerical ranges as used herein are intended to include every number and
subset of numbers contained within that range, whether specifically disclosed
or not.
Further, these numerical ranges should be construed as providing support for a
claim
directed to any number or subset of numbers in that range. For example, a
disclosure of from 1 to 10 should be construed as supporting a range of from 2
to 8,
from 3 to 7, from 5 to 6, from 1 to 9, from 3.6 to 4.6, from 3.5 to 9.9, and
so forth.
Any reference to singular characteristics or limitations of the present
disclosure shall include the corresponding plural characteristic or
limitation, and vice
versa, unless otherwise specified or clearly implied to the contrary by the
context in
which the reference is made.
Any combination of method or process steps as used herein may be
performed in any order, unless otherwise specifically or clearly implied to
the contrary
by the context in which the referenced combination is made.
The nutritional compositions and methods may comprise, consist of, or consist
essentially of the elements and features of the disclosure described herein,
as well
as any additional or optional ingredients, components, or features described
herein
or otherwise useful in a nutritional application.
Product Form
The nutritional compositions may be formulated and administered in any known
or otherwise suitable oral form. Any solid, liquid, or powder form, including
combinations or variations thereof, are suitable for use herein, provided such
forms
allow for safe and effective oral delivery to the individual of the essential
ingredients
as also defined herein.
The nutritional compositions are most suitably formulated as aqueous
emulsions, including water-in-oil emulsions, oil-in-water emulsions, or
complex (e.g.,
oil-in-water-in-oil emulsion) or other emulsion systems. As applied to the
nutritional
compositions herein, the nutritional emulsion embodiments are most typically
oil-in-
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water emulsions comprising an internal or discontinuous oil phase that
comprises the
curcuminoids and polar oil components as described herein.
The emulsion embodiments include conventional emulsions having a mean a
droplet diameter of greater than 0.8 microns, including greater than 1 micron,
and
also including from 1.2 microns to 5 microns.
Polar Oil
The nutritional compositions comprise a polar oil, which may represent all or
some of the total fat in the compositions. The polar oil is defined by a
selected HL B
value that ultimately favors, along with the optional selection of proper
processing
temperatures, the dissolution of a beneficial ratio of individual curcuminoids
as
described herein.
HLB values are a well known measure of the degree to which a material is
hydrophilic and or lipophilic, and may be determined by any one of a number of
methods well known in the chemical or formulation arts. HLB values are often
used
to characterize the relative extent to which a surfactant, emulsifier or
similar other
material would favor solubility in oil or water. Materials having a higher HLB
value
would tend to favor solubility in water while materials having a lower HLB
value would
tend favor solubility in oil.
It has been found that curcuminoids can be dissolved in certain oils, the
dissolution of which favors a more beneficial distribution or weight ratio of
curcuminoids during typical processing temperatures. More specifically, it has
been
found that these certain oils (referred to herein as "polar oils") are those
having HLB
values within the ranges as described herein. Oils having HLB values below
this
range do not solubilize enough of the curcuminoids while oils having HLB
values
above this range more easily result in curcuminoid distributions outside the
beneficial
ranges (for curcuminoid ratios) during normal processing temperatures as
defined
herein.
It should be noted, however, that many of these polar oils can still be
processed
at temperatures sufficiently high to drive the curcuminoid distribution past
the
desirable curcuminoid distribution range and toward 100% dissolution of all of
the
curcuminoids. It is therefore not enough that the composition merely contains
a
combination of the polar oil and curcuminoids. Instead, the combination must
also
include the desired curcuminoid ratio as defined herein, which is most readily
obtained by controlling and limiting processing temperatures during
dissolution of the
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curcuminoid extract in the polar oil. It should also be noted that the recited
curcuminoid distribution may be found in the nutritional composition or in an
oil phase
within of an emulsion embodiment hereof. For the latter, the nutritional
emulsion may
or may not contain an overall curcuminoid distribution within the ranges
recited
herein provided that it comprises an internal oil phase that does indeed
contain
selected curcuminoid distribution defined herein.
Polar oils suitable for use herein have an HLB value of from about 0.7 to
about
14, including from about 1 to about 8, and also including from about 3 to
about 7. It
is understood that the selection of these oils, as well as any other nutrient
described
herein, must also be suitable for oral administration to be applicable to the
present
compositions.
Non limiting examples of suitable polar oils include medium chain triglyceride
(MGT) oils. As used herein, the terms "medium chain triglyceride", "medium
chain
triglyceride oil" and "MCT oil" are used interchangeably and include
triacylglycerol
esters of C6-C12, more typically C6-10, fatty acids. The relative ratios of
the
different fatty esters can vary. The approximate ratios of these fatty acids
in
commercial MCT oils derived from coconut oil, for example, which are also
suitable
for use herein are 2(C6):55(C8):42(C10):1(C12).
Other non-limiting examples of polar oils suitable for use in the compositions
include C4-C18 fatty acids, C6-C18 monoglycerides, C8-C18 diglycerides, C4-C14
triglycerides, and mixtures or variations thereof. Another example of a
suitable polar
oil is Datem (diacetyl tartaric (acid) ester of monglyceride). It is
understood,
however, that all such oils must also have the requisite HLB value to be
effective for
use as a polar oil herein.
The amount of the polar oil used in the nutritional composition varies
depending
upon a number of factors, including the desired amount of curcuminoids to be
dissolved, the processing temperature employed during dissolution, and
chemical
nature of other ingredients in the composition. However, the polar oil most
typically
represents from about 0.1% to about 10%, including from about 0.3% to about
5%,
by weight of the composition.
The polar oil may represent all or some of the fat in the composition, but
will
most typically represent from about 10% to 100%, including from about 20% to
about
95%, and also including from about 50% to about 90%, by weight of the total
fat or in
the alternative by weight of the total fat in the oil phase of an oil-in-water
emulsion
embodiment.
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Curcuminoids
The nutritional compositions comprise a combination of curcumin,
demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC) that are solubilized
in selected ratios within the polar oil component, or an oil phase comprising
the polar
oil component, of the compositions.
The ratios of the individual curcuminoids in the nutritional compositions
herein
are different than the ratios found naturally in curcuminoid-containing plants
and
natural extracts. These new ratios designed to optimize their collective
biological
activity while minimizing their collective impact on the color of the
nutritional
composition. These new ratios include a weight ratio of bisdemethoxycurcumin
to
curcumin of more than about 1:8, including from about 1:1 to about 1:7, and
also
including from about 1:3 to about 1:7, and a weight ratio of
bisdemethoxycurcumin to
demethoxycurcumin of more than about 1:2.5, including from about 1:1 to about
1:2
including from about 1:1.5 to about 1:1.9.
The total curcuminoid concentration in the nutritional compositions may range
from at least about 0.001%, including from about 0.002% to about 1.0%,
including
from about 0.005% to about 0.8%, also including from 0.03% to about 0.3%, and
also
including from about 0.1% to about 0.25%, by weight of the nutritional
composition.
The term "total curcuminoid" as used herein means the amount or
concentration of the combination of curcumin, demethoxycurcumin, and
bisdemethoxycurcumin, excluding any other curcuminoids that may also be
formulated into the composition.
Although the nutritional compositions may further comprise different types of
curcuminoids, these compositions may also be free of such other types of
curcuminoids. These compositions may also be free of unsolubilized
curcuminoids,
including unsolubilized curcumin, demethoxycurcumin, and bisdemethoxycurcumin.
The total curcuminoid concentration in the nutritional composition most
suitably
represents from about 50% to 100%, including from about 80% to about 98%, by
weight of any and all curcuminoids in the compositions. In other words, it is
desirable
to have solubilized curcumin, solubilized demethoxycurcumin, and solubilized
bisdemethoxycurcumin as the only curcuminoids in the nutritional compositions.
The three individual curcuminoids in the nutritional compositions have varying
physical and biological activities, which activities are well known and
reported in the
literature. Curcumin, for example, has a higher natural distribution in
Turmeric than
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in the nutritional compositions of the present disclosure. Curcumin also has a
more
intense yellow color as compared to demethoxycurcumin and bisdemethoxycurcumin
as well as a lower metabolic recovery, inhibition of microtubule assembly, and
uptake
by colon cancer cells. bisdemethoxycurcumin by contrast provides higher
metabolic
recovery, inhibition of microtubule assembly, and uptake by colon cancer cells
than
either curcumin or demethoxycurcumin. Some of these know curcuminoids
properties are summarized below.
Property/Activity Curcumin DMC BDMC
Molecular Weight 368.4 338.4 308.4
Natural distribution in Turmeric, %w/w 75% 18% 7%
Color (molar absorptivity) 58,530 54,800 46,400
(428 nm) (424 nm) (416 nm)
Metabolic Recovery -50% -50% -75%
Inhibition of Microtubule Assembly 50% @ 40% @ 70% @
40pm 30pm 20pm
Uptake by Colon Cancer Cells, relative 1.00 1.30 2.24
to curcumin = 1.00
Neuroprotective Activity, approximate 1.00 0.50 0.00
The term "metabolic recovery" as used herein refers to the percentage of
ingested curcuminoid actually metabolized by the body. The term "inhibition of
microtubule assembly" as used herein refers to the ability to decrease the
rate of
cancer cell growth/procession by a curcuminoid. The term "cancer cell uptake"
as
used herein refers to the ability of the curcuminoid to enter into a cancer
cell. These
last two characteristics - inhibition of microtubule assembly and cancer cell
uptake -
are advantageous properties in that they may act to slow the progression of
cancer
cell growth.
In short, by optimizing the distribution or weight ratio of these individual
curcuminoids as described herein, their biologically activities can be
maximized while
decreasing the intensity of undesirable yellow color imparted to the
nutritional
product.
Macronutrients
The nutritional compositions comprise fat, protein, and carbohydrate
macronutrients. Any source of such nutrients that are known or otherwise
suitable
for use in an oral nutritional product is also suitable for use herein,
provided that such
nutrients are compatible with the selected ingredients in the composition and
provided that the fat component includes the polar oil as described herein.
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Although concentrations or amounts of each macronutrient in the compositions
may vary depending upon the nutritional needs of the intended user, such
concentrations or amounts most typically fall within one of the following
embodied
ranges A-F.
Macronutrient Embodiment A Embodiment B Embodiment C
Carbohydrate 10-70 20-60 40-60
% total calories
Protein 10-65 10-50 15-35
% total calories
Fat 5-40 10-30 15-25
% total calories
Embodiment D Embodiment E Embodiment F
Carbohydrate 1-40 4-30 10-20
wt/wt%
Protein 0.1-30 0.5-15 1-5
wt/wt%
Fat 0.5-30 1-15 2-10
wt/wt%
The nutritional compositions comprise a fat source, which includes the polar
oil
component as described herein. The polar oil may represent all or just some of
the
fat source. Non-limiting examples of suitable fats for use in addition to the
polar oils
include coconut oil, fractionated coconut oil, soy oil, corn oil, olive oil,
safflower oil,
high oleic safflower oil, sunflower oil, high oleic sunflower oil, palm and
palm kernel
oils, palm olein, canola oil, marine oils, cottonseed oils, and combinations
thereof.
The term "fat" as used herein includes both fats and oils, solid or liquid,
unless
otherwise specified.
The nutritional compositions also comprise a carbohydrate source. Non
limiting examples of suitable carbohydrates include hydrolyzed or modified
starch or
cornstarch, glucose polymers, corn syrup, corn syrup solids, rice-derived
carbohydrate, glucose, fructose, lactose, high fructose corn syrup,
indigestible
oligosaccharides (e.g., fructooligosaccharides), honey, sugar alcohols (e.g.,
maltitol,
erythritol, sorbitol), and combinations thereof.
The nutritional compositions also comprise a protein source. Non limiting
examples of suitable protein sources include hydrolyzed, partially hydrolyzed
or non-
hydrolyzed proteins or protein sources, and can be derived from any known or
otherwise suitable source such as milk (e.g., casein, whey), animal (e.g.,
meat, fish),
cereal (e.g., rice, corn), vegetable (e.g., soy), or combinations thereof. Non-
limiting
examples of such proteins include milk protein isolates, casein protein
isolates, milk
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protein concentrate, whole cows milk, partially or completely defatted milk,
soy
protein isolates, and so forth.
Optional Ingredients
The nutritional compositions may further comprise other optional components
that may modify the physical, chemical, aesthetic or processing
characteristics of the
products or serve as pharmaceutical or additional nutritional components when
used
in a targeted population. Many such optional ingredients are known or
otherwise
suitable for use in nutritional products and may also be used in the
compositions
herein, provided that such optional ingredients are safe and effective for
administration and are compatible with the essential and other selected
components
in the composition.
Non-limiting examples of such other optional ingredients include
preservatives,
anti-oxidants, buffers, pharmaceutical actives, sweeteners, colorants,
flavors, flavor
enhancers, thickening agents and stabilizers, emulsifying agents, lubricants,
and so
forth.
The nutritional compositions may further include one or more minerals, non-
limiting examples of which include phosphorus, sodium, chloride, magnesium,
manganese, iron, copper, zinc, iodine, calcium, potassium, chromium,
molybdenum,
selenium, and combinations thereof.
The nutritional compositions may also include one or more vitamins, non-
limiting examples of which include carotenoids (e.g., beta-carotene,
zeaxanthin,
lutein, lycopene), biotin, choline, inositol, folic acid, pantothenic acid,
choline, vitamin
A, thiamine (vitamin B1), riboflavin (vitamin B2), niacin (vitamin 83),
pyridoxine
(vitamin B6), cyanocobalamin (vitamin B12), ascorbic acid (vitamin C), vitamin
D,
vitamin E, vitamin K, and various salts, esters or other derivatives thereof,
and
combinations thereof.
Method of Manufacture
The nutritional compositions may be prepared in accordance with the methods
herein, or may be prepared by any known or otherwise suitable technique for
bringing together the individual components, ingredients, and/or features into
a
finished nutritional product.
The methods for preparing the compositions may comprise the following steps:
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(a) combining curcuminoids with a polar oil as defined herein, wherein the
curcuminoids comprise curcumin, demethoxycurcumin (DMC), and
bisdemethoxycurcumin (BDMC);
(b) heating the combination of curcuminoids and the polar oil to a temperature
sufficient to solubilize a fraction but not all of the curcuminoids in the
polar oil,
wherein the resulting heated combination includes solubilized and
unsolubilized curcuminoids;
(c) removing at least some, most typically from about 25% to 100% by,
including from about 75% to about 100%, and also including from 80% to
95%, by weight of the unsolubilized curcuminoid fraction from the combination
to form a solution comprising the polar oil and solubilized curcumin,
solubilized demethoxycurcumin, and solubilized bisdemethoxycurcumin,
within the weight ratios as defined herein; and
(d) introducing, adding, or otherwise formulating the solution comprising the
polar oil and the solubilized curcuminoids into a nutritional composition as
defined herein.
In accordance with step (a) of the method, the polar oil may be used alone or
in
combination with other oils. When used in combination with other oils,
however,
such combination must still be such that the combination during the method
ultimately solubilizes at least a fraction of the curcuminoids to within the
relative
curcuminoid weight ratios as defined herein.
Also in accordance with step (a) of the method, and prior to heating of step
(b),
the resulting combination of curcuminoids and polar oil may comprise from
about
0.25% to about 17%, including from about 0.4% to about 5%, also including from
about 1.5% to about 3.5%, by weight of the curcuminoids.
Also in accordance with step (a), the combination of curcuminoids may be in
the form of natural extracts from Turmeric or other natural curcuminoid
sources, and
thus may further comprise other curcuminoids other than curcumin,
demethoxycurcumin, and bisdemethoxycurcumin.
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In accordance with step (b) of the method, the combination of curcuminoids and
polar oil are heated to a temperature and for a period of time sufficient to
solubilize
the desired fraction but not all of the curcuminoids. It is understood,
however, that
the polar oil may be heated before, during, or after addition of the
curcuminoid
source, so long as the heat provided allows for dissolution of the fraction of
the
curcuminoids. Oil temperatures may range up to about 90 C, including from
about
20 C to about 75 C, also including from about 40 C to about 65 C. Oil
temperatures
of about 55 C are highly effective.
The distribution (i.e. relative weight ratios) of the individual solubilized
curcuminoids within the soluble fraction can be further modified by adjusting
the
temperature of the polar oil in step (b). In other words, because of the
different
solubility profiles of curcumin, demethoxycurcumin, and bisdemethoxycurcumin
in the
polar oil, the temperature in step (b) may be selected to modify and help
achieve the
desired ratio of the solubilized curcuminoids in the polar oil. Curcumin, for
example,
which is the major curcuminoid in the compositions, is not appreciably soluble
in
MCT oil at temperatures below 95 C, however, it is now predicted that complete
curcuminoid solubility will be achieved in the polar oil, especially when the
polar oil
comprises MCT oil, at about 163 C.
The highest efficiency (i.e., property or activity per unit color) for
desirable
properties of the nutritional composition, such as metabolic recovery,
inhibition of
microtubule protein assembly, and uptake by cancer cells, is achieved at about
55 C,
which allows for the greatest enrichment of bisdemethoxycurcumin in the
nutritional
composition. Accordingly, a balance is made between optimal solubility and
efficiency of the curcuminoids in the end nutritional composition to determine
the
temperature at which the combination of curcuminoids and polar oil are heated
in the
method herein.
In accordance with step (c) of the method, once the combination of
curcuminoids and polar oil are sufficiently heated and solubilized, the
unsolubilized
curcuminoid fraction from the combination is removed or otherwise separated
from
the polar oil composition. The unsolubilized fraction may be removed or
separated
from the polar oil composition using any known or otherwise suitable technique
for
removing unsolubilized solids from oil. For example, the unsolubilized
fraction can
be removed using centrifugation or filtration. More particularly, in one
embodiment,
the unsolubilized fraction may be removed using a thermostatted centrifuge,
which
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has temperature control capability in that it is capable of maintaining a
temperature of
from about 15 C to about 90 C.
The methods may further include formulating the solubilized curcuminoid
fraction into a nutritional composition comprising fat, protein, and
carbohydrate. This
may be achieved by any known or otherwise suitable method for adding a fat to
a
nutritional composition, including a nutritional aqueous emulsion. Once the
ingredients are combined, they are often transferred to a suitable device and
homogenized to form a stable oil-in-water emulsion
The above method may include any one or more of the other formulation or
other feature described herein for the nutritional compositions.
EXAMPLES
The following examples illustrate specific embodiments and or features of the
nutritional compositions and or methods.
Example 1
A suspension is prepared comprising 2.4% by weight of CURCUMIN C3
COMPLEX (Sabinsa Corporation, Payson, Utah) in NEOBEE 1053 (MCT oil
from Stepan Company, Northfield, Illinois). The suspension is heated to
temperatures of from 55 C to 165 C, during which the temperature is maintained
for
about two minutes at each of 55 C, 65 C, 75 C, 85 C, 95 C, and 165 C. An
aliquot
is taken from the suspension during each of the two minute temperature
plateaus
and centrifuged five minutes at 15,000 x g to thus remove undissolved solids
from
the suspension. The centrifuged aliquot, which is now a solution comprising
solubilized curcuminoids, is diluted in a 2:100 volume ratio with
dimethylsulfoxide and
tested for curcuminoid content using high pressure liquid chromatography
(HPLC).
The results are summarized below.
Temp. Soluble Soluble ¨S-oluble Soluble BDMC BDMC to
C curcuminoids, curcumin, DMC, BDMC, to curcumin
% of total as % of as % of as % of DMC wt ratio
curcurninoids total total total wt
____________________ curcumin DMC BDMC ratio
A 22 17.4 = 7.7 38.1 80.1 1 : 1.6
B 55 19.4% 9.5% 40.7% 84.6% - 1 :1.6 1 : 1.4
C 65 22.9% = 11.2%-- -49.7% 89.4% 1 : 1.8 1 : 1.6
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D 75 27.0% 14.0% 57.9%
94.9% 1:2M 1:1.9
E 85 32.3% 18.6% 65.8% 99.4% 1 : 2.2 1 :
2.3
F 95 38.6% 25.5% 70.8% 100.6% = 1 : 2.3 1 :
3.2
G 165 100% 100% 100%
100% 1:2.6 1:10.7
CC3 1:2.6 1:10.7
Powder2
1. Room temperature
2. CURCUMIN C3 COMPLEX Powder not combined with MCT oil
The above table illustrates the extent to which the curcuminoid ratios in
CURCUMIN C3 COMPLEX@ shift when combined with oil having an HLB value of
between 0.7 and 11 (e.g., MCT oil with HLB value of 1.4) as a function of oil
temperature. Aliquots F and G solubilized the curcuminoids to outside the
beneficial
ranges defined herein. Each of the resulting Aliquots A-E, however, fall
within the
requisite curcuminoid ratios, and thus provide increased bioactivity and
bioavailability
due to a solubility shift that favors an increase in the relative amount of
BDMC to
DMC and BDMC to curcumin. At the same time, each of the resulting solutions A-
E
also have a reduced color impact (i.e., increased bioactivity per unit color)
due to a
solubility shift that favors the less colorful BDMC. Optimal curcuminoid
ratios for
bioactivity, bioavailability and color impact occur at about 55C .
Example 2-5
Examples 2-5 illustrate nutritional compositions of the present disclosure
formulated as oil-in-water emulsions. The ingredients for each exemplified
composition are described in the following tables. All ingredient amounts are
listed
as kg per 1000 kg batch of product, unless otherwise specified.
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Example Example Example Example
Ingredient
2 3 4 5
Water QS QS QS QS
Com maltodextrin 118.18 118.18 118.18 118.18
Sodium caseinate 34.19 34.19 34.19 34.19
Milk protein isolate 31.37 31.37 3137 31.37
Sucrose 26.39 26.39 26.39 26.39
Corn syrup 16.93 16.93 16.93 16.93
Sardine oil 15.35 15.35 15.35 15.35
Fructooligosaccharide (FOS) 13.16 13.16 13.16 13.16
NEOBEE 10531 11.76 11.76 11.76 l 1.76
Calcium caseinate 9.337 9.337 9.337 9.337
Sodium citrate 3.378 3.378 3.378 3.378
Potassium citrate 3.372 3.372 3.372 3.372
Canola oil 3.265 3.265 3.265 3.265
Magnesium chloride 2.678 2.678 2.678 2.678
Micronized tri-calcium phosphate
2.183 2.183 2.183 2.183
MTCP
Soybean oil 1.932 1.932 1.932 1.932
Flavor 1.800 1.800 1.800 1.800
Curcuminoids (extracted at 22 C) 0.100
Curcuminoids (extracted at 55 C) 0.500
Curcuminoids (extracted at 65 C) 0.750
Curcuminoids (extracted at 75 C) 2.000
Lecithin 1.380 1.380 1.380 1.380
Magnesium phosphate dibasic 0.5860 0.5860 0.5860 0.5860
Choline chloride 0.5511 0.5511 0.5511 0.5511
Potassium hydroxide 45% solution 0.2862 0.2862 0.2862 0.2862
Ascorbic acid 0.2650 0.2650 0.2650 0.2650
Taurine 0.2646 0.2646 0.2646 0.2646
Water soluble premix 0.2510 0.2510 0.2510 0.2510
Potassium chloride 0.1596 0.1596 0.1596 0.1596
L-Carnitine 0.1500 0.1500 0.1500 0.1500
Trace/Ultra Trace Minerals 0.1317 0.1317 0.1317 0.1317
Vitamins D, E, K 0.0956 0.0956 0.0956 0.0956
Ascorbyl palmitate 0.064 0.064 0.064 0.064
Carrageenan 0.0611 0.0611 0.0611 0.0611
Vitamin A palmitate 0.0165 0.0165 0.0165 0.0165
Tocopherol-2 Antioxidant 0.011 0.011 0.011 0.011
Potassium iodide 0.0002 0.0002 0.0002 0.0002
1. MCT oil from Stepan Company, Northfield, Illinois
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PCT/US2010/027477
The curcuminoid blends for use in the illustrated examples comprise
solubilized
curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC), and are
free of undissolved curcuminoids.
The curcuminoid blends are prepared by first combining CURCUMIN C3
COMPLEX (Sabinsa Corporation, Payson, Utah) in powder form with a polar oil
(NEOBEE 1053). The initial combination comprises between 0.25% and 17% by
weight of the CURCUMIN C3 COMPLEX. The initial combination is then heated to
the desired temperature (22 C, 55 C, 65 C, or 75 C) to solubilize a fraction
of the
curcuminoids in the polar oil, wherein the resulting heated combination
includes
solubilized and unsolubilized curcuminoids. The undissolved curcuminoids or
solids
are then removed from the heated combination by centrifugation to form from
the
combination a solution comprising the polar oil and solubilized curcumin,
solubilized
demethoxycurcumin, and solubilized bisdemethoxycurcumin, wherein the weight
ratio
of the solubilized bisdemethoxycurcumin to solubilized demethoxycurcumin is
between 1:1 and 1:2.5 and the weight ratio of solubilized bisdemethoxycurcumin
to
curcumin is between 1:1 and 1:7. Each of the curcuminoid blends used in
Examples
2-5 have the BDMC to DMC and BDMC to curcumin ratios as those described for
the
corresponding Example 1 aliquots described in Example 1
Each of the nutritional emulsions described in Examples 2-5 may be prepared
in accordance with the methods described herein. Generally, once the
curcuminoid
blend is prepared (as above), it and the other ingredients may be formulated
into the
desired nutritional by forming at least three separate slurries (carbohydrate-
mineral
slurry, protein slurry, fat slurry including the above curcuminoid blends) as
appropriate for the different ingredients, and then blend the various slurries
together,
heat treat and homogenize the resulting blend, and then standardize. The
resulting
composition is then flavored, aseptically packaged into bottles or retort
sterilized
The resulting nutritional emulsions are oil-in-water emulsions having minimal
color impact from the curcuminoid blend.
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