U.S. patent application number 09/809192 was filed with the patent office on 2001-11-01 for oil composition.
This patent application is currently assigned to KAO CORPORATION. Invention is credited to Hosoya, Naoki, Koike, Shin, Yasumasu, Takeshi.
Application Number | 20010036502 09/809192 |
Document ID | / |
Family ID | 18595562 |
Filed Date | 2001-11-01 |
United States Patent
Application |
20010036502 |
Kind Code |
A1 |
Koike, Shin ; et
al. |
November 1, 2001 |
Oil composition
Abstract
Disclosed herein is an oil composition containing a diglyceride,
in which at least 55% by weight of the constitutive acyl groups are
unsaturated acyl groups, and 15 to 100% by weight thereof are
.omega.3 type unsaturated acyl groups having at least 20 carbon
atoms, in an amount of not less than 10% by weight, but less than
40% by weight, and a triglyceride, in which at least 70% by weight
of the constitutive acyl groups are unsaturated acyl groups, and 5
to 80% by weight thereof are a linoleyl group, in an amount of 40.1
to 89.8% by weight. The composition effectively develops the
physiological functions derived from .omega.3 type unsaturated
fatty acids, such as antiarteriosclerotic effect, and is excellent
in oxidation stability, flavor and the like. Foods and medicines
containing such an oil composition are provided.
Inventors: |
Koike, Shin; (Sumida-Ku,
JP) ; Hosoya, Naoki; (Sumida-Ku, JP) ;
Yasumasu, Takeshi; (Sumida-Ku, JP) |
Correspondence
Address: |
OBLON SPIVAK MCCLELLAND MAIER & NEUSTADT PC
FOURTH FLOOR
1755 JEFFERSON DAVIS HIGHWAY
ARLINGTON
VA
22202
US
|
Assignee: |
KAO CORPORATION
Chuo-ku
JP
|
Family ID: |
18595562 |
Appl. No.: |
09/809192 |
Filed: |
March 16, 2001 |
Current U.S.
Class: |
426/608 ;
426/541; 426/601; 426/610 |
Current CPC
Class: |
A61K 31/23 20130101;
C11C 3/06 20130101; A23D 9/007 20130101; A23V 2002/00 20130101;
A23L 33/12 20160801; A23V 2002/00 20130101; A61P 9/10 20180101;
C11C 3/10 20130101; A23D 9/00 20130101; A23V 2250/5118 20130101;
A23V 2250/54246 20130101; A23V 2250/156 20130101; A23V 2250/1868
20130101; A23V 2250/70 20130101 |
Class at
Publication: |
426/608 ;
426/601; 426/610; 426/541 |
International
Class: |
A23D 007/00 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 21, 2000 |
JP |
2000-078110 |
Claims
What is claimed is:
1. An oil composition comprising a diglyceride, in which at least
55% by weight of the constitutive acyl groups are unsaturated acyl
groups, and 15 to 100% by weight thereof are .omega.3 type
unsaturated acyl groups having at least 20 carbon atoms, in an
amount of not less than 10% by weight, but less than 40% by weight,
and a triglyceride, in which at least 70% by weight of the
constitutive acyl groups are unsaturated acyl groups, and 5 to 80%
by weight thereof are a linoleyl group, in an amount of 40.1 to
89.8% by weight.
2. The oil composition according to claim 1, wherein 10 to 85% by
weight of the constitutive acyl groups in the triglyceride are
monoenoic acyl groups.
3. The oil composition according to claim 1 or 2, which comprises
0.1 to 10% by weight of a monoglyceride.
4. The oil composition according to any one of claims 1 to 3, which
comprises 0.1 to 10% by weight of a glyceride polymer.
5. The oil composition according to any one of claims 1 to 4, which
comprises 0.01 to 5% by weight of an antioxidant.
6. A food comprising the oil composition according to any one of
claims 1 to 5.
7. A medicine comprising the oil composition according to any one
of claims 1 to 5 as an active ingredient.
Description
BACKGROUND OF THE INVENTION
[0001] 1. Field of the Invention
[0002] The present invention relates to an oil or fat (hereafter
referred to as "oil" merely) composition which effectively develops
physiological functions derived from .omega.3 type unsaturated
fatty acids, such as antiarteriosclerotic effect, and is excellent
in oxidation stability, flavor and the like, and foods and
medicines comprising such an oil composition.
[0003] 2. Description of the Background Art
[0004] In recent years, it has been clarified that diglycerides
have an obesity-preventing effect, an effect to prevent an increase
in weight, etc. (Japanese Patent Application Laid-Open Nos.
300828/1992, 300826/1992 and 300825/1992, etc.), and it is
attempted to incorporate these into various kinds of foods.
[0005] On the other hand, it has been known that .omega.3 type
unsaturated fatty acids such as docosahexaenoic acid (DHA) and
eicosapentaenoic acid (EPA) are mainly contained in the form of
triglyceride in fish oil and the like in plenty and have effective
physiological activities such as antiarteriosclerotic effect,
antitumor activity, immune activation, antiallergic activity,
improvement in brain function and improvement in visual
function.
[0006] As oils highly containing such diglycerides and .omega.3
type unsaturated fatty acids, there have been known, for example, a
natural oil that DHA among constitutive fatty acids of the oil is
contained in a proportion of at least 60%, and the total content of
diglycerides and monoglycerides is at least 80% of the oil
(Japanese Patent Application Laid-Open No. 60181/1996), and the
like. In addition, there has been known a high unsaturated fatty
acid-containing oil composition having a glyceride composition that
the total amount of monoglycerides and diglycerides is greater than
the amount of triglycerides, and enhanced in hydration property
(Japanese Patent Application Laid-Open No. 265795/1998).
[0007] However, the .omega.3 type unsaturated fatty acids are very
poor in oxidation stability. When a .omega.3 type unsaturated fatty
acid is oxidized, the oxidized unsaturated fatty acid involves a
problem that not only its physiological activity functions are
lost, but also the a living body is adversely affected when such an
unsaturated fatty acid is taken. In addition, a .omega.3 type
unsaturated fatty acid-containing oil has an unpleasant flavor
derived from its raw oil, and so a problem is offered when it is
used in food in particular. Further, .omega.3 type unsaturated
fatty acids involve a problem that when they are converted into
their corresponding diglycerides, the diglycerides do not become
liquid at the temperature of the living body, so that the
physiological activities of the .omega.3 type unsaturated fatty
acids are hard to be developed.
[0008] There is a demand for solution of a conflicting problem that
when a .omega.3 type unsaturated acyl content is lowered in order
to avoid these problems, the development of the physiological
activity functions, which is an object of incorporation, is
deteriorated.
SUMMARY OF THE INVENTION
[0009] It is therefore an object of the present invention to
provide an oil composition which is hard to be oxidized, is
excellent in flavor and liquid at the temperature of a living body
and has high physiological activities of .omega.3 type unsaturated
fatty acids, and foods and medicine comprising such an oil
composition.
[0010] The present inventors have attracted attention to the
compositions of acyl groups constituting a diglyceride and a
triglyceride and found that when c3 type unsaturated acyl groups as
acyl groups constituting a diglyceride and a linoleyl group
(cis,cis-9,12-octadecadienoyl group) as an acyl group constituting
a triglyceride are contained in specified amounts in an oil
composition comprising a diglyceride in a specified amount, the
above object can be achieved.
[0011] According to the present invention, there is thus provided
an oil composition comprising a diglyceride, in which at least 55%
by weight (hereafter indicated merely by "%") of the constitutive
acyl groups are unsaturated acyl groups, and 15 to 100% thereof are
.omega.3 type unsaturated acyl groups having at least 20 carbon
atoms, in an amount of not less than 10%, but less than 40%, and a
triglyceride, in which at least 70% of the constitutive acyl groups
are unsaturated acyl groups, and 5 to 80% thereof are a linoleyl
group, in an amount of 40.1 to 89.8%.
[0012] According to the present invention, there is also provided a
food comprising such an oil composition.
[0013] According to the present invention, there is further
provided a medicine comprising such an oil composition.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0014] In the present invention, the acyl groups constituting a
diglyceride include .omega.3 unsaturated acyl groups having at
least 20 carbon atoms, preferably 20 to 24 carbon atoms in a
proportion of 15 to 100%, preferably 20 to 90%, particularly
preferably 40 to 70% based on all the acyl groups in the
diglyceride. In order to effectively achieve the physiologically
active effect of .omega.3 type unsaturated fatty acids, it is
necessary to contain .omega.3 unsaturated acyl groups having at
least 20 carbon atoms in an amount of at least 15%. The term
".omega.3 type unsaturated fatty acid" as used herein means an acyl
group that a first unsaturated bond is located on the third carbon
atom from a .omega. position when the positions of unsaturated
bonds are specified from the .omega. position, and that has at
least 2 unsaturated bonds. As the .omega.3 type unsaturated acyl
groups having at least 20 carbon atoms, are particularly preferred
eicosapentaenoyl and docosahexaenoyl groups.
[0015] In the present invention, the number of carbon atoms in
remaining acyl groups constituting the diglyceride is preferably 8
to 24, particularly 16 to 22. In order to maintain the oil
composition according to the present invention in a liquid state at
the temperature of a living body, the unsaturated acyl groups must
be contained in a proportion of at least 55%, preferably at least
70%, particularly preferably at least 80% based on all the acyl
groups in the diglyceride.
[0016] The unsaturated acyl groups are preferably contained in a
proportion of at most 98% from the viewpoints of production cost
and effect.
[0017] The diglyceride can be obtained by an optional process such
as transesterification of any of various oils such as fish oil and
rapeseed oil containing .omega.3 type unsaturated acyl groups,
monoenoic acyl groups with glycerol and the like or esterification
of a fatty acid derived from such an oil with glycerol. The
reaction method thereof may be either a chemical reaction method
making use of an alkali catalyst or the like or a biochemical
reaction method making use of an enzyme such as lipase. The content
of such a diglyceride in the oil composition according to the
present invention must be not lower than 10%, but lower than 40%,
and is particularly preferably 15 to 35%. When the content is not
lower than 10%, but lower than 40%, the development of
physiological activities derived from the (93 type unsaturated
fatty acids is easily consistent with oxidation stability in
cooperation with a linoleyl group in the triglyceride.
[0018] In the present invention, the acyl groups constituting a
triglyceride include a linoleyl group in a proportion of 5 to 80%,
preferably 7 to 55%, more preferably 7 to 45%, particularly
preferably 10 to 30% based on all the acyl groups in the
triglyceride. In order to maintain the oil composition according to
the present invention in a liquid state at the temperature of a
living body and to avoid side effect by .omega.3 type unsaturated
fatty acids, the linoleyl group must be contained in a proportion
of at least 5% based on all the acyl groups in the triglyceride.
The linoleyl group may be preferably contained in a proportion of
at most 80% from the viewpoints of the physiologically active
effect of the .omega.3 type unsaturated fatty acids and oxidation
stability.
[0019] In the present invention, the number of carbon atoms in
remaining acyl groups constituting the triglyceride is preferably 8
to 24, particularly 16 to 22. In order to maintain the oil
composition according to the present invention in a liquid state at
the temperature of a living body, the unsaturated acyl groups must
be contained in a proportion of at least 70%, preferably at least
75%, more preferably at least 80, particularly preferably at least
90% based on all the acyl groups in the triglyceride. The
unsaturated acyl groups are preferably contained in a proportion of
at most 98% from the viewpoints of production cost and effect. The
.omega.3 type unsaturated acyl groups are preferably contained in a
proportion of at most 30%, more preferably at least 20% based on
all the acyl groups in the triglyceride from the viewpoint of
oxidation stability. The .omega.6 type unsaturated acyl groups such
as a .gamma.-linolenyl group (all cis-6,9,12-octadecatrienoyl
group) and an arachidonyl group (all cis-5,8,11,14-eicosatetraenoyl
group) are preferably contained in a proportion of at most 5%, more
preferably at least 2%, particularly preferably 0% based on all the
acyl groups in the triglyceride from the viewpoint of oxidation
stability. The triglyceride can be obtained from a vegetable oil
such as soybean oil, rapeseed oil, palm oil, rice oil or corn oil,
an animal oil such as beef tallow or fish oil, or a hardened oil,
fractionated oil or random transesterified oil thereof. The content
of the triglyceride in the oil composition according to the present
invention is preferably 40.1 to 89.8%, particularly 50 to 80% from
the viewpoint of masking of flavor derived from the raw oil.
[0020] The triglyceride preferably contains monoenoic acyl groups
in a proportion of 10 to 85%, more preferably 15 to 70%,
particularly preferably 25 to 60% based on all the acyl groups. The
monoenoic acyl group is an acyl group having a carbon-carbon double
bond and 8 to 24 carbon atoms, preferably 16 to 22 carbon atoms. As
examples of the monoenoic acyl groups, are particularly preferred
hexadecamonoenoyl, octadecamonoenoyl, eicosamonoenoyl and
docosamonoenoyl groups.
[0021] The content of a monoglyceride in the oil composition
according to the present invention is preferably 0.1 to 10%, more
preferably 0.1 to 5%, particularly preferably 0.1 to 2%, still more
preferably 0.1 to 1.5% from the viewpoint of improvement in the
flavor of the oil composition. The content of free fatty acids is
preferably at most 2%, more preferably at most 1%, particularly
preferably at most 0.5% from the viewpoint of improvement in the
flavor of the oil composition.
[0022] In the present invention, a glyceride polymer may preferably
be contained in order to improve the oxidation stability. The
glyceride polymer is obtained by intermolecular polymerization of a
glyceride such as a triglyceride, diglyceride or monoglyceride (for
example, "Kagaku to Seibutu (Chemistry and Organism), Vol. 21, page
179, 1983), and no particular limitation is imposed on the
polymerization degree of the glyceride, the positions of fatty acid
esters, the kinds of acyl groups constituting the fatty acid
esters, etc. The content of the glyceride polymer in the oil
composition is preferably 0.1 to 10%, more preferably 0.1 to 5%,
particularly preferably 0.2 to 2% from the viewpoints of
improvement in oxidation stability and flavor of the oil
composition. The amount of such a glyceride polymer can be
controlled by suitably controlling reaction temperature conditions
and the like upon synthesis of the glyceride polymer. The glyceride
polymer can be determined by an HPLC process in which a gel
permeation chromatographic column is connected.
[0023] The oil composition according to the present invention can
be prepared by mixing the above-described components and suitably
subjecting the resulting mixture to heating, stirring and/or the
like. Alternatively, the oil composition can be obtained by
transesterification of an oil containing .omega.3 type unsaturated
acyl groups, a linoleyl group, monoenoic acyl groups and the like,
such as fish oil or rapeseed oil, with glycerol, or the like. It
may also be prepared by fractionating triglycerides, diglycerides,
monoglycerides, glyceride polymers, free fatty acids and the like
from the resulting transesterification product, and then suitably
mixing these fractionation products with one another, and
optionally mixing an ordinary edible oil such as soybean oil,
rapeseed oil or perilla oil therewith. A preparation process by
transesterification of an oil containing .omega.3 type unsaturated
acyl groups, a linoleyl group, monoenoic acyl groups and the like
with an ordinary edible oil and glycerol, and a process, in which
an ordinary edible oil is mixed with a transesterification product
of an oil containing .omega.3 type unsaturated acyl groups, a
linoleyl group, monoenoic acyl groups and the like with glycerol
are more preferred.
[0024] An antioxidant may be added to the oil composition according
to the present invention. Any antioxidant may be added so far as it
is commonly used in foods and medicines. However, one of catechin,
tocopherol, vitamin C fatty acid esters and natural antioxidant
components, or a combination of two or more components thereof is
preferred, with catechin being particularly preferred. Examples of
the vitamin C fatty acid esters include the palmitate and stearate,
and examples of the natural antioxidant components include extracts
from herbs such as rosemary, and leaves and roots of peach. The
antioxidant is preferably added in a proportion of 0.01 to 5%,
particularly 0.05 to 1% to the oil composition according to the
present invention.
[0025] The oil composition thus obtained has excellent
physiological activities such as effects of facilitating combustion
of body fat, reducing blood sugar, consuming triglyceride in blood,
reducing insulin in blood, improving liver function, reducing blood
pressure, and reducing plasminogen activator inhibitor type 1
(PAI-1) in addition to antiarteriosclerotic effect, based on its
cell membrane fluidity-improving effect and the like, is good in
digestibility because it is liquid at the temperature of a living
body, can be stored over a long period of time because it is
excellent in oxidation stability, and moreover is excellent in
flavor. In particular, since the .omega.3 type unsaturated acyl
groups are present as acyl groups constituting a diglyceride, the
oil composition acts at a lower concentration than the case where
they are present as free fatty acids, and so it has good
fast-acting property, and is good in flavor and safe. Since the oil
composition according to the present invention has such excellent
properties, it can be utilized for foods and medicines.
[0026] With respect to the foods, the oil composition may be used
as oil-containing foods containing the oil composition as a part of
food. Examples of such oil-containing foods include healthy foods
that the specified functions are exhibited to promote health.
Specific examples thereof include capsule preparations, tablet
preparations, granule preparations, bakery foods such as bread and
cookie, dressings such as French dressing, mayonnaises, creams,
confectionery such as chocolates and potato chips, and drinks, in
which such an oil composition is incorporated. Such oil-containing
food can be produced by adding food materials commonly used
according to the kind of the oil-containing food in addition to the
oil composition in accordance with a method known per se in the
art. It is preferred that the amount of the oil composition
according to the present invention to be incorporated in food be
generally 0.1 to 100%, particularly 1 to 80% though it varies
according to the kind of the food. It may also be used as a food
material of oils for fried foods such as tempura and fries, or oils
for frizzled foods.
[0027] No particular limitation is imposed on the forms of the
medicines, and examples thereof include oral preparations, such as
solid preparations such as powder preparations, granule
preparations, capsule preparations, pill preparations and tablet
preparations; and liquid preparations such as aqueous preparations,
suspension preparations and emulsion preparations. Such an oral
preparation can be prepared by adding an excipient, a
disintegrator, a binder, a lubricant, a surfactant, an alcohol,
water, a water-soluble polymer, an edulcorant, a taste corrigent,
an acid corrigent and/or the like commonly used according to the
form of the oral preparation in addition to the oil composition in
accordance with a method known per se in the art. Examples of
medicines for oral administration include platelet aggregation
inhibitors, brain function improvers and visual function improvers.
It is preferred that the amount of the oil composition according to
the present invention to be incorporated in the oral preparation be
generally 0.1 to 100%, particularly 1 to 80% though it varies
according to the application and form of the medicine. With respect
to the dose of the oil composition as a medicament, it is
preferably administered in a dose of 0.1 to 50 g per day.
Meanwhile, the administration may be once per day, or may be
divided into several times per day.
EXAMPLE 1
[0028] Rapeseed oil (product of Nisshin Oil Mills Ltd.; 100 parts
by weight), a high DHA-containing oil ("DHA-45", product of MARUHA
CORP.; 100 parts by weight) and glycerol (product of Wako Pure
Chemical Industries, Ltd.; 8 parts by weight) were mixed with one
another, and an alkali catalyst (sodium methoxide, CH.sub.3ONa; 0.5
parts by weight) was mixed to the resultant mixture to conduct
transesterification at 100.degree. C. for 4 hours under reduced
pressure (0.133 kPa). The reaction product thus obtained was
fractionated by column chromatography on silica gel, and a
triglyceride (64.9 parts by weight), a diglyceride (34.8 parts by
weight), a monoglyceride (0.2 parts by weight) and a free fatty
acid (0.1 parts by weight) were mixed with the resultant
fractionation product to prepare Oil Composition 1.
EXAMPLE 2
[0029] Olive oil (product of Wako Pure Chemical Industries, Ltd.;
120 parts by weight), a high EPA-containing oil ("EPA28", product
of NIPPON SUISAN, INC.; 80 parts by weight) and glycerol (8 parts
by weight) were mixed with one another to conduct
transesterification and fractionation of respective components in a
similar manner to Example 1. A triglyceride (79.2 parts by weight),
a diglyceride (22.4 parts by weight), a monoglyceride (0.1 parts by
weight), a free fatty acid (0.1 parts by weight) and a glyceride
polymer (0.2 parts by weight) were then mixed with the resultant
fractionation product to prepare Oil Composition 2.
EXAMPLE 3
[0030] Purified fish oil (product of Kao Corporation; 200 parts by
weight) and glycerol (8 parts by weight) were mixed with each other
to conduct transesterification and fractionation of respective
components in a similar manner to Example 1. A diglyceride (10
parts by weight), a monoglyceride (0.1 parts by weight), a
glyceride polymer (0.2 parts by weight) and perilla oil (product of
OHTA OIL MILL CO., LTD.; 89.7 parts by weight) were then mixed with
the resultant fractionation product to prepare Oil Composition
3.
EXAMPLE 4
[0031] A high DHA-containing oil ("DHA-45", product of MARUHA
CORP.; 100 parts by weight) and glycerol (6 parts by weight) were
mixed with each other to conduct transesterification and
fractionation of respective components in a similar manner to
Example 1. A diglyceride (23.5 parts by weight), a monoglyceride
(0.2 parts by weight), a free fatty acid (0.1 parts by weight), a
glyceride polymer (0.1 parts by weight) and rapeseed oil (product
of Nisshin Oil Mills, Ltd.; 76.1 parts by weight) were then mixed
with the resultant fractionation product to prepare Oil Composition
4.
EXAMPLE 5
[0032] A high DHA-containing oil ("DD Oil Type 3G", product of
NIPPON SUISAN, INC.; 100 parts by weight) and glycerol (6 parts by
weight) were mixed with each other to conduct transesterification
and fractionation of respective components in a similar manner to
Example 1. A triglyceride (20.0 parts by weight), a diglyceride
(16.9 parts by weight), a monoglyceride (1.1 parts by weight), a
free fatty acid (0.1 parts by weight), a glyceride polymer (0.2
parts by weight) and soybean oil (product of Nisshin Oil Mills,
Ltd.; 61.7 parts by weight) were then mixed with the resultant
fractionation product to prepare Oil Composition 5.
EXAMPLE 6
[0033] A high DHA-containing oil ("DHA-45", product of MARUHA
CORP.; 100 parts by weight), glycerol (4 parts by weight) and
sodium methoxide (0.3 parts by weight) were mixed with one another
to conduct transesterification at 100.degree. C. for 4.5 hours
under reduced pressure (0.133 kPa). The resultant reaction product
was subjected to molecular distillation (210.degree. C.,
0.00266-0.00666 kPa) and then decolorized and deodorized. A
composition obtained in this stage contained 44.5% of triglyceride,
53.8% of diglyceride, 0.6% of monoglyceride, 0.1% of free fatty
acid and 1.0% of glyceride polymer. Fifty parts by weight of this
composition and 50 parts by weight of rapeseed oil (product of
Nisshin Oil Mills, Ltd.) were mixed with each other to prepare Oil
Composition 6. The thus-obtained Oil Composition 6 contained 71.8%
of triglyceride, 27.3% of diglyceride, 0.3% of monoglyceride, 0.1%
of free fatty acid and 0.5% of glyceride polymer.
EXAMPLE 7
[0034] A high DHA-containing oil ("DHA-45", product of MARUHA
CORP.; 100 parts by weight), soybean oil (product of Nisshin Oil
Mills, Ltd.; 100 parts by weight), glycerol (0.5 parts by weight)
and sodium methoxide (0.5 parts by weight) were mixed with one
another to conduct transesterification at 100.degree. C. for 4
hours under reduced pressure (0.133 kPa). The resultant reaction
product was subjected to molecular distillation (210.degree. C.,
0.00266-0.00666 kPa) and then decolorized and deodorized to prepare
Oil Composition 7. The thus-obtained Oil Composition 7 contained
78.2% of triglyceride, 20.1% of diglyceride, 0.3% of monoglyceride,
0.1% of free fatty acid and 1.3% of glyceride polymer.
COMPARATIVE EXAMPLES 1 AND 2
[0035] Soybean oil (product of Nisshin Oil Mills, Ltd.) and fish
oil (product of Kao Corporation) were provided as Oil Composition 8
(Comparative Example 1) and Oil Composition 9 (Comparative Example
2).
COMPARATIVE EXAMPLE 3
[0036] The transesterification and fractionation product of Example
3 was used and mixed with a triglyceride (71.7 parts by weight), a
diglyceride (27.8 parts by weight), a monoglyceride (0.1 parts by
weight) and a free fatty acid (0.4 parts by weight) to prepare Oil
Composition 10.
COMPARATIVE EXAMPLE 4
[0037] The transesterification and fractionation product of Example
3 was used and mixed with a triglyceride (36.4 parts by weight) and
a diglyceride (63.6 parts by weight) to prepare Oil Composition
11.
[0038] Principal fatty acid compositions of diglyceride and
triglyceride fractions derived from the respective oil compositions
obtained in Examples 1 to 7 and Comparative Examples 3 and 4 are
shown in Tables 1 and 2,
1TABLE 1 Principal fatty acid composition in diglyceride Comp.
Example Ex. 1 2 3 4 5 6 7 3 4 .omega.3 C18:3 5 0 11 0 0 0 4 0 0
C20:5 4 12 12 7 7 7 3 15 15 C22:6 23 6 7 44 22 46 23 8 8 Monoenoic
C16:1 2 4 8 3 4 3 2 9 9 C18:1 34 49 6 13 23 11 17 4 4 C20:1 2 0 4 1
3 1 1 5 5 C22:1 1 0 4 1 1 1 1 5 5 .omega.6 C18:2 11 7 4 2 4 2 27 2
2 Saturated C16:0 7 9 15 11 16 11 11 17 17 C18:0 2 2 4 3 4 3 3 4 4
Measured by gas chromatography after methylation.
[0039]
2TABLE 2 Principal fatty acid composition in triglyceride Comp.
Example Ex. 1 2 3 4 5 6 7 1 2 3 4 .omega.3 C18:3 5 0 63 10 6 7 4 10
0 0 0 C20:5 4 12 0 0 2 2 3 0 15 15 15 C22:6 23 6 0 0 6 14 23 0 8 8
8 Mono- C16:1 2 4 0 0 1 1 2 0 9 9 9 enoic C18:1 34 49 15 57 24 43
17 57 4 4 4 C20:1 2 0 0 2 1 2 1 2 5 5 5 C22:1 1 0 0 1 0 1 1 1 5 5 5
.omega.6 C18:2 11 7 14 21 40 15 27 21 2 2 2 Saturated C16:0 7 9 5 4
12 6 11 4 17 17 17 C18:0 2 2 4 2 4 2 3 2 4 4 4 Measured by gas
chromatography after methylation.
TEST EXAMPLE 1
[0040] Investigation of Cell Membrane Fluidity-Improving
Effect:
[0041] Wistar mail rats aged 10 weeks were divided into 7 groups,
and a feed (see Table 3) containing corn oil (10%) and one (4%) of
Oil Compositions 1 to 5 and 8 to 10 was given to its corresponding
group for 2 weeks. The microsomes were then taken out of the liver
of each rat to determine a total cholesterol quantity and a
phospholipid quantity, thereby finding a ratio of the total
cholesterol quantity to the phospholipid quantity. The results are
shown in Table 4. In the table, the numerical values indicate
relative values that a value in the case where a feed (control)
containing only corn oil (10%) was used is regarded as 100. The
smaller relative value indicates that the fluidity of a liver
microsome cell membrane was more improved ("Nippon Shokuhin Kagaku
Kogaku Kaishi", Vol. 43, page 1231, 1996).
3 TABLE 3 Control Oil Composition 1-5, 8-10 Casein 20 20 Corn oil
10 10 Oil composition 0 4 Mineral mixture 4 4 Vitamin mixture 1 1
Cellulose 4 4 Choline chloride 0.15 0.15 Starch 60.85 56.85
[0042]
4 TABLE 4 Oil composition Total cholesterol/phospholipid* 1 80 2 87
3 92 4 74 5 87 8 110 9 98 10 95 Control 100 *Indicated by relative
values that a value in the case where the feed (control) containing
only corn oil (10%) was used is regarded as 100.
[0043] Oil Compositions 1 to 5 according to the present invention
exhibited a cell membrane fluidity-improving effect superior to Oil
Compositions 8 to 10.
TEST EXAMPLE 2
[0044] Investigation of Improvement in Resistance to Oxidation:
[0045] Each (20 g) of deodorized Oil Compositions 1 to 5, 9 to 11
and 12 to 15 was placed in a 50-mL sample bottle, and the bottle
was left at rest in an opened state for 5 days in a thermostat
controlled at 40.degree. C. Thereafter, an absorbance at 532 nm was
measured in accordance with the thiobarbituric acid method
("Yukagaku", Vol. 24, page 481, 1975). The amount of
malondialdehyde (MDA) was determined by using
1,1,3,3-tetraethoxypropane to prepare a calibration curve. The
results are shown in Table 5.
5TABLE 5 (mg/kg) Oil composition Amount of MDA 1 8.7 2 4.5 3 7.2 4
8.9 5 6.4 9 13.2 10 14.1 11 18.5 12.sup.(1) 2.0 13.sup.(2) 4.6
14.sup.(3) 3.7 15.sup.(4) 4.1 .sup.(1)Oil Composition 12: Oil
Composition 2 98.0% Sankatol No 1* 2.0 (Taiyo Chemical) .sup.(2)Oil
Composition 13: Oil Composition 4 99.9% Teafuran 90S** 0.04 (Itoen)
Vitamin C palmitate 0.04 (Roche) Mix Vitamin E MDE-6000 0.02
(Yashiro) *Catechin content 10% **Catechin content 90% .sup.(3)Oil
Composition 14: Obtained by replacing Oil Composition 2 in Oil
Composition 12 by Oil Composition 6. .sup.(4)Oil Composition 15:
Obtained by replacing Oil Composition 4 in Oil Composition 13 by
Oil Composition 7.
[0046] Oil Compositions 1 to 5 and 12 to 15 according to the
present invention were superior in oxidation stability to Oil
Compositions 9 to 11.
TEST EXAMPLE 3
[0047] Each (20 g) of Oil Compositions 1 to 7, 9 and 10 was placed
in a 50-mL sample bottle, and the bottle was tightly stoppered and
left at rest at 5.degree. C. for 3 hours and then at 35.degree. C.
for 0.5 hours. Thereafter, the appearance of the oil composition
was visually observed to evaluate it in accordance with the
following standard.
6 TABLE 6 Oil composition Evaluation 1 .circleincircle. 2
.circleincircle. 3 .circleincircle. 4 .circleincircle. 5
.circleincircle. 6 .circleincircle. 7 .circleincircle. 9 .DELTA. 10
x .circleincircle.: No turbidity was observed; .smallcircle.:
Turbidity was scarcely observed; .DELTA.: Turbidity was slightly
observed; x: Turbidity was observed.
[0048] No turbidity was observed on all the oil composition
according to the present invention.
TEST EXAMPLE 4
[0049] Common salt (0.5 g) and pepper (0.1 g) were added to the
whole egg (100 g), the egg was sufficiently beaten up, a sample oil
composition (5 g) was placed on a frying pan (24 cm), and the
frying pan was put over a fire (city gas flow rate: 2.2 L/min).
After 30 seconds, the egg previously beaten was put into the frying
pan and heated for 20 seconds while scrambling with chopsticks to
cook scrambled egg. The scrambled egg was dished to
organoleptically evaluate it by 10 panelists in accordance with the
following standard.
[0050] Evaluation Standard:
[0051] 5: Very delicious;
[0052] 4: Delicious;
[0053] 3: It is a toss-up whether the dish was delicious or
not;
[0054] 2: Not very delicious;
[0055] 1: Not delicious.
[0056] The average values of evaluation scores are shown in Table
7.
7 TABLE 7 Oil composition Evaluation 1 3.8 2 4.3 3 4.0 4 3.8 5 4.1
10 1.7
[0057] The flavor of the scrambled egg cooked with each of the oil
compositions according to the present invention was evaluated as
delicious.
TEST EXAMPLE 5
[0058] Evaluation of French Dressing as to Flavor:
[0059] A wine vinegar (50 parts by weight) was mixed with common
salt (2.5 parts by weight), pepper (0.6 parts by weight) and
mustard (0.5 parts by weight). Oil Composition 1 or 6 (90 parts by
weight) was added to the resultant mixture while stirring by a
whipper. The resultant mixture was sufficiently stirred to prepare
a French dressing. The dressing was put on coleslaw to evaluate it
as to flavor by ten panelists in accordance with the
above-described evaluation standard. As a result, the average
values were 4.1 and 4.0, respectively, and the French dressings
were evaluated as delicious.
TEST EXAMPLE 6
[0060] Evaluation of Oral Syrup Preparation as to Flavor:
[0061] After sodium benzoate (0.06 parts by weight) and purified
sucrose (50 parts by weight) were added to heated purified water
(40 parts by weight) into a solution, hydroxypropyl cellulose (0.5
parts by weight) was added, and the mixture was stirred by a
homomixer into a solution, thereby preparing Liquid A. On the other
hand, sucrose fatty acid ester (0.2 parts by weight) was dispersed
in Oil Composition 5 or 7 (5 parts by weight) to prepare Liquid B.
Liquid B was added while stirring Liquid B by the homomixer, and
purified water (4.24 parts by weight) was added thereto, thereby
formulating an oral syrup preparation. The syrup preparations thus
obtained were evaluated at to flavor in the same manner as in Test
Example 4. The average values thereof were 4.4 and 4.5,
respectively, and the syrup preparations were evaluated as being
good in flavor.
[0062] As described above, the oil compositions according to the
present invention are hard to be oxidized because the content of
the co3 type unsaturated acyl group-containing diglyceride is
relatively low, is excellent in flavor and can effectively exhibit
the physiological activities of .omega.3 type unsaturated fatty
acids.
* * * * *