Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Food or edible as carrier for pharmaceutical
Reexamination Certificate
2000-02-09
2004-02-17
Webman, Edward J. (Department: 1621)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Food or edible as carrier for pharmaceutical
C426S601000, C426S603000, C514S549000
Reexamination Certificate
active
06692762
ABSTRACT:
The beneficial effects of conjugated long chain polyunsaturated fatty acids in food products for animals or humans have been recognised in the prior art.
EP 411.101 e.g, discloses, that compositions containing free conjugated linoleic acid (=CLA), such as 9.11-dienic and 10.12-dienic fatty acids or non-toxic salts thereof can be used to preserve products by inhibiting mould growth. According to this EP′101 the free acids are prepared by reacting linoleic acid with a protein, capable of effecting the transformation of linoleic acid to the desired acid forms at temperatures up to 85° C. The CLA obtained contains both the 9.11 and 10.12-octadecadienoic acids and active isomers therefrom. Because of cis/trans-isomerism above CLA's can contain 8 different isomers, i.e. cis
9
-cis
11
; cis
9
-trans
11
; trans
9
-cis
11
; trans
9
-trans
11
; cis
10
-cis
12
; cis
10
-trans
12
; trans
10
-cis
12
and trans
10
-trans
12
. From those isomers the cis
9
-trans
11
and trans
10
-cis
12
are the most abundant, while their concentrations are about equal. It is generally believed, that those two most abundant isomers are responsible for the beneficial effects of the compositions, containing CLA's.
According to EP 440.325 CLA's can be applied as “metal chelator” in natural foods. The CLA's contain 9.11 and 10.12-octadecadienoic acid, salts or other derivatives thereof. The free acids can be prepared by e.g. an enzymic treatment, using &Dgr;
12
cis &Dgr;
11
trans isomerase, of linoleic acid.
In U.S. Pat. No. 5,430,066 it is disclosed, that CLA's can be applied in foods for preventing weight loss, reduction in weight gain or anorexia in animals or humans. Also disclosed is, that these CLA's can alleviate the adverse catabolic effects of a product from the immune-system, in particular from interleukin-1.
From U.S. Pat. No. 5,428,072 it is known, that CLA's can be used for the increase of the efficiency of feed conversion to body weight in an animal.
Shantha c.s disclosed in J. of AOAC Intern 76 (3) 1993, p. 644-649 that CLA-isomers are potential anticarcinogens.
According to Fogerty c.s in Nutrition Reports Intern 38 (5), 1988, p. 937-944 cis
9
-trans
11
linoleic acid can be used in various foods or human milk.
U.S. Pat. No. 4,164,505 discloses a process, wherein unconjugated unsaturated fattty acids are isomerised into conjugated unsaturated fatty acids by a treatment with base. As a result of this process a kinetically controlled reaction-mixture will be obtained, wherein the double bonds are conjugated but distributed over the whole carbon chain of the polyunsaturated fatty acids. Therefore this process does not result in organic materials, wherein the two most abundant conjugated polyunsaturated fatty acid moieties L1 and L2 are present in a weight-ratio
L
1
L
2
=
2.3
-
99
,
as we aim for as a result of our process.
Above prior art methods and products do have a number of drawbacks. E.g. the methods for the preparation of the CLA's according to above prior art cannot be applied on a commercial scale, e.g. because the yields of the products are very limited. Moreover the products obtained always will have one specific ratio between the cis
9
-trans
11
/trans
10
-cis
12
isomers (in general about 1.0). Therefor compositions with an other ratio than 1.0 cannot be obtained. As the effectiveness of the two isomers for specific purposes are different it is highly desirable to have the opportunity to make CLA's, wherein the ratio
cis
9
-
trans
11
trans
10
-
cis
12
can be chosen freely, depending on the conditions applied during the process.
Therefore our invention concerns a new process for the preparation of CLA's, wherein the ratio
cis
9
-
trans
11
trans
10
-
cis
12
can be chosen freely. This new method can be applied for the preparation both of new CLA-compositions and known CLA-compositions.
So our inventions concerns a process for the preparation of materials, containing conjugated unsaturated fatty acid moieties, wherein a material, containing at least 5 wt % of conjugated polyunsaturated fatty acid moieties, comprising at least two different isomers L
1
and L
2
in a weight ratio L
1
:L
2
=X
A
, is subjected to an enzymic conversion, selected from one of the following conversions:
(i) free fatty acids with:
(a) mono- or polyalcohols, or
(b) mono, -di-triglycerides, or
(c) alkylesters, or
(d) phospholipids
(ii) mono, -di- or triglycerides with:
(a) water, or
(b) mono- or polyalcohols, or
(c) alkylesters, or
(d) phospholipids
(iii) phospholipids with:
(a) water, or
(b) alkylesters, or
(c) other phospholipids, or
(d) mono- or polyols
(iv) alkylesters, or wax-esters with:
(a) water, or
(b) mono- or polyols, or
(c) free fatty acids, or
(d) phospholipids,
wherein an enzyme is applied, that has the ability to discriminate between L
1
and L
2
, which conversion results in a mixture of at least two products (I) and (II), from which at least one product (I) or (II) contains L
1
and L
2
in a weight-ratio X
B
, X
B
being at least 1.1 X
A
, preferably at least 1.2 X
A
, most preferably at least 1.3 X
A
, and wherein L
1
and L
2
are different isomers of polyunsaturated fatty acids with at least two unsaturations and at least 18 carbon atoms.
Enzymes that can be applied for the enzymic conversion are e.g.
Geotrichum candidum
and
Candida rugosa
and phospholipases.
As indicated above many different types of reactants can be applied for the enzymic conversion. It was found, that very good results are obtained, when the conversion is performed on a mixture of free fatty acids, containing at least 5 wt %, preferably at least 10 wt %, most preferably at least 15 wt % of conjugated polyunsaturated fatty acids and a phospholipid or a mono, -di- or triglyceride;
Preferred starting materials, applicable in the process according to the invention have a weight ratio X
A
(ie L
1
:L
2
) of about 1.0.
According to another embodiment of the invention water or glycerol, mixed with a mono, -di- or triglyceride could be converted as well. In this instance the glyceride material is the reactant having at least 5 wt % conjugated polyunsaturated fatty acids in it.
Although above process can be applied on any starting material, wherein L
1
and L
2
can be chosen from all long chain polyunsaturated fatty acid moieties with at least two unsaturations and 18 or more carbon atoms, as long as the long chain polyunsaturated acids present are present in different cis/trans-isomeric forms, it is preferred that L
1
and L
2
are cis
9
trans
11
and trans
12
cis
12
-linoleic acid (or vice versa)
The process of the invention can be applied for the preparation of known compounds, however also novel compositions can be obtained by using this process. These novel compounds (compositions) have unexpected properties, because of the weight-ratio L
1
:L
2
that occurs in these compositions. Therefore our invention also concerns novel organic materials, which-materials contain at least 1 wt % of conjugated polyunsaturated fatty acid moieties with a chain length of at least 18 C-atoms, wherein the conjugated polyunsaturated fatty acid moieties at least comprise two isomers L
1
and L
2
in a weight-ratio:
L1
L2
=
2.3
-
99
,
preferably 4-20, most preferably 8-15 L
1
being the most abundant and L
2
being the second most abundant conjugated polyunsaturated fatty acid moiety in the material, while L
1
and L
2
are different isomers of polyunsaturated fatty acids with at least two unsaturations and at least 18 carbon atoms.
The organic materials, that can be obtained can be: either a mixture of free fatty acids, a mixture of wax-esters, a mixture of low alkylesters, a mixture of monoglycerides, or, diglycerides or triglycerides or mono, -di- and triglycerides, or a mixture of phospholipids, or a mixture of one or more components of said mixtures.
In the novel organic materials L
1
and L
2
can both be selected from cis
9
,trans
11
and trans
10
,cis
12
-linoleic acid.
In many instances the starting material for our process will be an animal-derived material, s
Cain Frederick William
McNeill Gerald Patrick
Moore Stephen Raymond
Zwemmer Olga Cornelia
Loders Croklaan B.V.
Morgan & Lewis & Bockius, LLP
Webman Edward J.
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