Compositions containing proanthocyanidin and a vitamin B6...

Details Compositions containing proanthocyanidin and a vitamin B6... Compositions containing proanthocyanidin and a vitamin B6...

2000-09-08

2004-02-03

Witz, Jean C. (Department: 1651)

Drug, bio-affecting and body treating compositions

Plant material or plant extract of undetermined constitution...

C424S777000, C514S474000, C514S400000

Reexamination Certificate

active

06685970

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to compositions containing proanthocyanidin, drinks, foods, cosmetics and medicaments containing these compositions and a method for stabilizing proanthocyanidin.
BACKGROUND ART
It is known that proanthocyanidin, which is a substance contained in a number of plants and having a strong antioxidant effect, is susceptible to oxidation and quickly undergoes oxidative polymerization in the presence of oxygen, thereby showing a color change.
Conventional techniques to stabilize proanthocyanidin mainly include addition of potassium pyrosulfite (e.g., to wine) and addition of ascorbic acid (e.g., to apple juice).
JP-A-6-336420 discloses cosmetics containing sodium hydrogensulfite, 1-hydroxyethane-1,1-disulfonic acid, diethylenetriamine pentaacetic acid or phytic acid to prevent the color change of proanthocyanidin with the passage of time (the term “JP-A” as used herein means an “unexamined published Japanese patent application”).
On the other hand, examples of methods for stabilizing polyphenol or preventing its color change or compositions for stabilizing polyphenol or preventing its color change are as follows: (1) a method for preventing the color change of polyphenol by adding a porphyrin zinc complex and an organic reducing agent to polyphenol as disclosed in JP-B-8-2819 (the term “JP-B” as used herein means an “examined Japanese patent publication”); (2) skin cosmetics containing a polyphenol compound together with a sucrose higher fatty acid ester disclosed in JP-A-5-112441; (3) skin cosmetics containing a polyphenol compound together with an alkyl glucoside disclosed in JP-A-5-163131; and (4) a method for preventing the color change of skin preparations for an external use which contain a polyphenol compound carrying at least 3 phenolic hydroxyl groups by adding a polyhydric alcohol or a sugar to the preparations disclosed in Japanese Patent No. 2,744,572.
SUMMARY OF THE INVENTION
An object of the invention is to provide proanthocyanidin-containing compositions having excellent proanthocyanidin stability, as well as drinks, foods, cosmetics and medicaments containing these compositions, and a method for stabilizing proanthocyanidin so as to prevent the color change, etc. caused by the oxidative polymerization, etc., thereof.
The invention provides compositions containing proanthocyanidin and a vitamin B
6
derivative or its salt, and drinks, foods, cosmetics and medicaments containing these compositions.
The invention further provides a method for stabilizing proanthocyanidin characterized by blending proanthocyanidin with a vitamin B
6
derivative or its salt.
The invention furthermore provides proanthocyanidin stabilizers containing a vitamin B
6
derivative or its salt.
DETAILED DESCRIPTION OF THE INVENTION
Particular examples of the vitamin B
6
derivative include pyridoxine, pyridoxal, pyridoxamine and phosphates thereof such as pyridoxal-5-phosphate. Pyridoxine, pyridoxal and pyridoxamine are compounds represented by the following general formula (I).
In the above formula, R
1
represents —CH
2
OH (pyridoxine), —CHO (pyridoxal), or —CH
2
NH
2
(pyridoxamine).
Examples of the salt of the vitamin B
6
derivative include inorganic acid salts (hydrochloride, sulfate, nitrate, phosphate and the like) and organic acid salts (maleate, fumarate, citrate, acetate and the like) of the vitamin B
6
derivative, preferably dietary, cosmetically or pharmaceutically acceptable salts. The vitamin B
6
derivative or its salt may exist in the form of a hydrate or a solvate in some cases.
The vitamin B
6
derivative or its salt can be synthesized by a known method described in, for example, Kagaku-Daijiten (ed. by Kagaku-Daijiten Henshu Iinkai, vol. 7, p. 406, Aug. 5, 1962). Alternatively, a commercially available product may be employed.
Examples of proanthocyanidin include compounds having two or more flavan-7-ol derivatives, which are represented by the following general formula (II), bonded together.
In the above formula, R
3
and R
4
are the same or different and each represents hydrogen, a hydroxyl group, a galloyloxy group or a glucopyranosyl group; and R
2
, R
5
, R
6
, R
7
, R
8
and R
9
are the same or different and each represents hydrogen or a hydroxyl group.
Preferable examples of the flavan-7-ol derivative represented by the general formula (II) include catechin, epicatechin, gallocatechin, epigallocatechin, afzelechin and epiaflezechin.
With respect to proanthocyanidin, a carbon atom of one flavan-7-ol derivative may be bonded to a carbon atom of another flavan-7-ol derivative through a single bond or an ether bond via an oxygen atom, etc. Any carbon or oxygen atom in formula (II) may participate in forming these bonds, although in the case of an ether bond, the bond is preferably formed via a hydroxyl group of the flavan-7-ol derivative. The flavan-7-ol derivatives which are bonded together to form proanthocyanidin may be either the same or different from each other.
The following general formulae (III-a), (III-b) and (III-c) show preferred examples of the bonding modes of these flavan-7-ol derivatives.
In the above formulae, R
3a
, R
4a
, R
3b
, R
4b
, R
3c
, R
4c
, R
3d
, R
4d
, R
3e
, R
4e
, R
3f
, and R
4f
, are the same or different and each represents hydrogen, a hydroxyl group, a galloyloxy group or a glucopyranosyloxy group; and R
5a
, R
6a
, R
7a
, R
8a
, R
9a
, R
2b
, R
5b
, R
7b
, R
8b
, R
9b
, R
5c
, R
6c
, R
7c
, R
8c
, R
9d
, R
2d
, R
5d
, R
6d
, R
7d
, R
8d
, R
9d
, R
5e
, R
6e
, R
7e
, R
8e
, R
9e
, R
2f
, R
5f
, R
7f
, R
8f
, and R
9f
are the same or different and each represents hydrogen or a hydroxyl group.
As the proanthocyanidin, it is preferable to use a compound having from 2 to 10, more preferably from 2 to 4, flavan-7-ol structural units as described above.
Examples of dimers of flavan-7-ol derivatives include epicatechin-catechin bonded compounds such as epicatechin-(4&bgr;→8)-catechin, epicatechin dimers such as epicatechin-(4&bgr;→6)-epicatechin and epicatechin-(&bgr;→8)-epicatechin (procyanidin B-2), and catechin-catechin dimers such as catechin-(4&agr;→8)-catechin. Examples of trimers of flavan-7-ol derivatives include epicatechin trimers such as epicatechin-(4&bgr;→8)-epicatechin-(4&bgr;→8)-epicatechin and epicatechin-(4&bgr;→8)-epicatechin-(4&bgr;→6)-epicatechin, catechin trimers such as catechin-(4&agr;→8)-catechin-(4&agr;→8)-catechin, and mixed epicatechin-catechin trimers such as epicatechin-(4&bgr;→8)-epicatechin-(4&bgr;→8)-catechin.
In addition, compounds wherein gallic acid or sugars (glucose, rhamnose and the like) are bonded to the above-described compounds also fall within the concept of the proanthocyanidin as used in the invention.
Proanthocyanidin has various isomers including optical isomers and all of these isomers and mixtures thereof may be utilized in the present invention.
Proanthocyanidin can be obtained by extraction (and optional purification) from various plants such as a grape, an apple, a barley, a persimmon, a coconut, a cacao, a pine, a blueberry, a strawberry, an adzuki bean and a peanut, which belong to the genera Vitis, Malus, Hordeum, Diospyros, Cocos, Theobroma, Pinus, Vaccinium, Fragaria, Phaseolus, Arachis, etc. It is also possible to obtain proanthocyanidin optionally by purifying from fermented products of these extracts, such as a wine, a cider, a beer and the like.
The extraction and purification from a plant may be carried out in the following manner, which is known in the art (Chemical & Pharmaceutical Bulletin, 38: 3218, 1990 and ibid., 40: 889-898, 1992; Acta Derm. Venereol. (Stockh.), 78, 428 (1998) or the like).
A plant material (a fruit, a seed, a leaf, a stem, a root, a rhizome, etc.) is harvested at an appropriate time and then optionally dried by, for example, usual air-drying to give a material to be extracted. The starting material is ground or cut into pieces and then extracted by a solvent. As the extraction solvent, hydrophilic or lipophilic solvents such as water, alcohols (etha

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