JP2004231749A - Sphingoglycolipid-containing composition and its preparation method - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To efficiently prepare a powdery sphingoglycolipid-containing composition free from defects such as stickiness or lump formation. <P>SOLUTION: The powdery sphingoglycolipid-containing composition is prepared by bringing a sphingoglycolipid-containing substance into contact with a cyclic oligosaccharide, such as β-cyclodextrin and/or γ-cyclodextrin, in the presence of a solvent having below-described properties (a) and (b) and water in a volume ratio of the solvent to water of (1/50)-3 and then drying the substance. The solvent used is other than water and has such properties that (a) the solvent and water are mutually soluble in each other and (b) the solvent is included by the cyclic oligosaccharide in the presence of water or in an anhydrous state. <P>COPYRIGHT: (C)2004,JPO&NCIPI

Description

[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a powdery glycosphingolipid-containing composition and a method for producing the same.
[0002]
[Prior art]
Among glycosphingolipids, monoglucosylceramide is widely present in plant tissue cell membranes and the like, and it is a known technique to obtain a composition containing glycosphingolipids from a plant tissue by extraction with an organic solvent. In recent years, such extracts containing monoglucosylceramide, especially those derived from plant tissues, have a moisturizing effect on the skin due to the effect of improving the hydration of the skin stratum corneum of mammals including humans, which is a feature of this compound. It is being used as a food material or cosmetic material.
[0003]
Glycosphingolipid-containing compositions extracted from plant tissues are added to foods or cosmetics by a known method that does not impair the skin moisturizing effect. Among them, when added to solid foods such as baked goods and tablets, and solid cosmetics such as foundations, a method of adding a powdered glycosphingolipid composition obtained by extraction in some way is most preferably used. It can be said that it is the means used.
[0004]
However, in order to extract glycosphingolipids from plant tissues, it is necessary to use an organic solvent (for example, see Patent Document 1). At this time, other lipid components are also extracted at the same time. Glycosphingolipid-containing compositions are usually high viscous liquids in the form of oil or semisolids in the form of wax, and have a problem that they are extremely difficult to be powdered. More specifically, when the glycosphingolipid-containing composition is applied to solid foods and solid cosmetics, the frequently used technique of pulverization using excipients is described in Examples in the preceding patents. Although it is found only to a certain extent (see, for example, Patent Document 2), only an example in which a large amount of an excipient of 9 to 10 times the mass is added to a glycosphingolipid-containing composition is shown, There is no prior example of powdering lipid-containing compositions with lower amounts of excipients.
[0005]
[Patent Document 1]
JP 2002-38183 A [Patent Document 2]
JP-A-11-113530
[Problems to be solved by the invention]
An object of the present invention is to obtain a useful glycosphingolipid-containing substance having a moisturizing effect as a powder free of stickiness and lump formation.
[0007]
[Means for Solving the Problems]
The present inventors have studied the excipients to be added when pulverizing the glycosphingolipid-containing substance in order to solve the above-mentioned problems. It has been found that powdering can efficiently produce powder having no problems such as stickiness and lump formation with the addition of as small an amount as possible, thereby completing the present invention.
[0008]
That is, the first of the present invention is to include a glycosphingolipid-containing composition characterized by being in powder form, comprising a cyclic oligosaccharide as an excipient, and preferably, the cyclic oligosaccharide is β-cyclodextrin and / or γ-cyclodextrin. The second aspect of the present invention is that sphingo is used in a state where a solvent other than water having the following properties (a) and (b) coexists at a volume ratio of 1/50 to 3 times with respect to water. The method for producing a glycosphingolipid-containing composition according to any one of claims 1 to 3, wherein the glycolipid-containing composition is brought into contact with a cyclic oligosaccharide and then dried.
(A) Mutual dissolution with water (b) Inclusion with the cyclic oligosaccharide to be used in the presence of water or in an anhydrous state
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, the present invention will be described in detail.
The glycosphingolipid in the present invention is contained in animal and plant tissues including microorganisms, and is obtained by a known method by solvent extraction (for example, see JP-A-2002-38183). As an extraction raw material, a plant tissue is preferable in consideration of the problem of pathogenic bacteria and viruses. Further, konjac potato is preferable in consideration of the content and the like, and specific examples include konjac potato, konjac fine powder, konjac coarse powder, konjac tobi powder and the like.
In the present invention, among the components of glycosphingolipids, those containing monoglucosylceramide in an amount of 0.1 to 90% by mass are preferable, and those containing 1.0 to 30% by mass are more preferably used.
[0010]
In the present invention, the excipient used for powdering the glycosphingolipid-containing substance needs to be a cyclic oligosaccharide, and a derivative thereof can also be used. Specifically, α-, β-, and γ-cyclodextrins and their methyl derivatives, hydroxypropyl derivatives, sulfobutyl ether derivatives, and other modified cyclodextrins and dextrins, which have a high degree of polymerization of more than 8 And cyclodextrins. Among them, β-cyclodextrin or γ-cyclodextrin, which are produced in large quantities worldwide and are inexpensive, or mixtures thereof are preferably used.
[0011]
The excipient in the powdery glycosphingolipid-containing composition of the present invention preferably contains 10 to 90% by mass, more preferably 30 to 80% by mass.
[0012]
The powdery glycosphingolipid-containing composition of the present invention is a powder having no stickiness or lump formation, and the particle size varies depending on the powdering apparatus used, but is generally about 5 mm or less. Further, the obtained powder can be further finely divided by an arbitrary pulverizer. Examples of such a crusher include a stone mill, a ball mill, a cutter mill and the like.
[0013]
The production method of the present invention is to provide a powdery glycosphingolipid-containing composition by bringing a glycosphingolipid-containing substance into contact with the above-mentioned cyclic oligosaccharide in the presence of water and a solvent other than water, followed by drying and powdering. It is a way to get things.
Solvents other than water used in the production method of the present invention are: (a) mutually soluble with water; and (b) inclusion in the cyclic oligosaccharide to be used in the coexistence with water or in an anhydrous state; It satisfies the property of Furthermore, in order to obtain a powder having a more uniform color tone faster and with a higher yield, it is preferable that the glycosphingolipid mixture be dissolved or dispersed uniformly, and that the boiling point is low and that it can be easily distilled off. Those that do not interact too strongly with the cyclic oligosaccharide (that is, those that have a small decrease in Gibbs energy upon inclusion) are preferred. Examples of such a solvent include, when the cyclic oligosaccharide is β-cyclodextrin or γ-cyclodextrin, or any mixture thereof, ethanol, n-butanol, isopropanol, and the like. When the powder obtained in (1) is used for oral use, among them, ethanol is most preferably used.
[0014]
The ratio of water to the solvent other than the above-mentioned water needs to be 1/50 or more and 3 times or less, and preferably 1/20 or more and 2 times or less, with respect to water. . If the solvent other than water is more than three times the volume of water, the resulting powder may be sticky and stick, and if the solvent is less than 1/50 with respect to water, There is a risk that progress will be slow, and neither can be adopted.
[0015]
It is desirable that the total amount of water and the solvent other than water be sufficient to sufficiently disperse the cyclic oligosaccharide used as an excipient. Time is unnecessarily extended. A preferable total amount of water and a solvent is 1 part by weight (mL) or more and 50 times or less (mL) or less, more preferably 1 time or more (mL) or more, with respect to 1 part by weight (g) of the cyclic oligosaccharide. It is less than double volume (mL).
[0016]
The amount of the excipient to be added is preferably 1/10 to 10 parts by weight, more preferably 1/2 to 5 parts by weight, based on 1 part by weight of the glycosphingolipid-containing substance. To do.
[0017]
It is preferable that the glycosphingolipid-containing substance, the cyclic oligosaccharide, the solvent and the water are well mixed in advance and then dried. At this time, the mixing order of the four types of substances may be any within a range in which the glycosphingolipid-containing substance is dissolved or uniformly dispersed, and as long as this condition is satisfied, the mixing is performed in any order. Even when the milky milky liquid or the original glycosphingolipid-containing substance is colored, a colored milky sol is obtained. When the whole becomes uniform, stop stirring and leave the emulsion sol as it is.
Within a few minutes after standing, the emulsion sol undergoes a sharp increase in viscosity, solidifies in a viscous to semi-solid state while keeping uniformity, and no sedimentation of excipients is observed. If drying is started in this state, a powdery glycosphingolipid-containing composition having no stickiness, surface adhesion or lump formation can be obtained.
[0018]
The method of powdering by drying is not particularly limited, and any known method can be used. Examples of such a method and apparatus include a spray drying method, mixing and stirring under reduced pressure, a drum dryer, a method using a thin film type drying apparatus such as a horizontal axis rotating type dryer, a method using a vibration drying apparatus, and the like. Can be Considering the melting point, decomposition temperature, and the like of the components contained in the glycosphingolipid-containing composition, among these, the glycosphingolipid-containing composition is less likely to be exposed to high temperatures, and the inside of the powdered container is in a reduced pressure state. More preferably, a method using a mixing and stirring device under reduced pressure, a thin film type drying device, a vibration drying device, or the like, which is a simple device, is more preferable.
[0019]
As a specific condition, when using a mixing and stirring device with a jacket capable of reducing the pressure inside, a uniform sol is charged, and the internal temperature of the drying device is preferably room temperature to 100 ° C, more preferably 30 ° C to 80 ° C. Drying and pulverization may be performed while stirring under reduced pressure under the following conditions. When a thin film type drying device such as a drum dryer is used, the temperature of the surface on which the material to be powdered forms a thin film, such as the drum surface of the drum dryer, is preferably 70 to 120 ° C., and more preferably 80 to 120 ° C. The temperature may be 110 ° C., and the substance to be powdered may be charged under reduced pressure.
[0020]
In addition, in the production method of the present invention, powdering can be performed while separately adding other powdering aids such as other excipients and surface lubricants. Examples of such powdering aids include polysaccharides such as dextrin, corn starch, and cellulose, and inorganic fine particles such as calcium carbonate, magnesium carbonate, silica, and alumina.
[0021]
The powder obtained as described above can be pulverized with a pulverizer or the like to further reduce the size. As such a crushing device and crushing method, known devices and methods such as a stone mill, a freeze crusher, a cutter mill, and a ball mill can be used.
[0022]
The powdery glycosphingolipid-containing composition finally obtained is a sticky, non-sticky, free-flowing powder, and even under a dry atmosphere, there is no formation of lumps due to long-term storage. is there.
[0023]
The powder of the glycosphingolipid-containing composition of the present invention can be blended in foods, pharmaceuticals and other preparations, cosmetics, and the like. Desirable forms for blending include baked goods such as cookies and biscuits, noodles such as bread, udon and pasta, chewable tablets, tablets and capsule preparations.
[0024]
【Example】
Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited thereto.
In addition, the following was used as a manufacturing apparatus (powdering apparatus).
(1) Vacuum mixing stirrer type: Super mixer SMV-20A type manufactured by Kawata Corporation (2) Drum dryer type: DD-1 type manufactured by Chuo Kakoki Co., Ltd.
The method for quantifying glycosphingolipids is as follows.
Glycosphingolipids were quantified by high performance liquid chromatography (HPLC). LC Module 1 manufactured by Waters was used, and Inertsil SIL100A manufactured by GL Sciences was used as a column. As a solvent, chloroform: methanol = 9: 1 (volume ratio) was used and measured at 25 ° C. at a flow rate of 1.0 mL / min. A light scattering detector (500 ELSD manufactured by ALLTECH) was used for detection.
[0026]
Example 1
1 kg of konjac flour powder was extracted with 2 L of ethanol for 2 hours to obtain 10.3 g of the extract after distilling off the solvent (glycosphingolipid content: 6.43% by weight). This extract was dissolved in 40 mL of ethanol to obtain a dark brown solution A. Separately, 20 g of β-cyclodextrin was mixed with 20 mL of water to obtain Paste B. The paste B was introduced into the solution A while stirring well, and the mixture was stirred well until the mixture became uniform, thereby obtaining a skin-colored sol C. After confirming that this flesh-colored sol C solidifies in a fresh cream form by standing for 5 minutes, it is vacuum-dried at 70 ° C. for 8 hours, and then pulverized by a pulverizer (household mill) to obtain a yellow uniform color. 30.1 g of a powder having an excellent color tone was obtained. The resulting powder was tack-free and a small amount was kneaded with polyethylene gloved hands, but did not lump.
[0027]
Example 2
1 kg of konjac flour powder was extracted with 2 L of ethanol for 2 hours to obtain 10.3 g of the extract after distilling off the solvent (glycosphingolipid content: 6.43% by weight). This extract was dissolved in 30 mL of ethanol, washed with 80 mL of water for 2 hours, added with 15 g of sodium chloride, heated and boiled, and the oil phase floating on the upper portion of the aqueous phase was recovered. The recovered oil phase was dissolved in 30 mL of ethanol, and after removing insoluble components, 6.6 g of ethanol-soluble components were recovered (glycosphingolipid content: 9.32% by weight). This was dissolved in 40 mL of ethanol to obtain a dark brown solution A. Separately, 20 g of β-cyclodextrin was mixed with 20 mL of water to obtain Paste B. The paste B was introduced into the solution A while stirring well, and the mixture was stirred well until the mixture became uniform, thereby obtaining a skin-colored sol C. After confirming that this flesh-colored sol C solidifies in a fresh cream form by standing for 5 minutes, it is vacuum-dried at 70 ° C. for 8 hours, and then pulverized by a pulverizer (household mill) to obtain a yellow uniform color. 30.1 g of a powder having an excellent color tone was obtained. The resulting powder was tack-free and a small amount was kneaded with polyethylene gloved hands, but did not lump.
[0028]
Example 3
1 kg of konjac flour powder was extracted with 2 L of ethanol for 2 hours to obtain 10.3 g of the extract after distilling off the solvent (glycosphingolipid content: 6.43% by weight). This extract was dissolved in 30 mL of ethanol, washed with 80 mL of water for 2 hours, added with 15 g of sodium chloride, heated and boiled, and the oil phase floating on the upper portion of the aqueous phase was recovered. The recovered oil phase was dissolved in 30 mL of ethanol, and after removing insoluble components, 6.6 g of ethanol-soluble components were recovered (glycosphingolipid content: 9.32% by weight). This was dissolved in 40 mL of ethanol to obtain a dark brown solution A. Separately, 20 g of γ-cyclodextrin was mixed with 20 mL of water to obtain Paste B. The paste B was introduced into the solution A while stirring well, and the mixture was stirred well until the mixture became uniform, thereby obtaining a skin-colored sol C. After confirming that this flesh-colored sol C solidifies in a fresh cream form by standing for 5 minutes, it is vacuum-dried at 70 ° C. for 8 hours, and then pulverized by a pulverizer (household mill) to obtain a yellow uniform color. 30.3 g of a powder having an excellent color tone was obtained. The resulting powder was tack-free and a small amount was kneaded with polyethylene gloved hands, but did not lump.
[0029]
Example 4
50 kg of konjac flying powder was extracted with 100 L of ethanol for 2 hours to obtain 496 g of an extract after distilling off the solvent (glycosphingolipid content: 6.63% by weight). This extract was dissolved in 2 L of ethanol to obtain a dark brown solution A. Separately, 1 kg of β-cyclodextrin was mixed with 1 L of water to obtain a paste B. The solution A was put into the body of a super mixer SMV-20A manufactured by Kawata Corporation, and the paste B was further introduced while stirring, and then stirred well until uniform to obtain a skin-colored sol C. After confirming that the skin color sol C solidifies in a fresh cream form by standing for 5 minutes, the mixture is stirred under reduced pressure at a jacket circulating water temperature of 70 ° C. for 8 hours, and finally, a uniform yellow skin color is obtained. 1449 g of powder having a good color were discharged. The resulting powder was tack-free and a small amount was kneaded with polyethylene gloved hands, but did not lump.
[0030]
Example 5
50 kg of konjac flying powder was extracted with 100 L of ethanol for 2 hours to obtain 496 g of an extract after distilling off the solvent (glycosphingolipid content: 6.63% by weight). This extract was dissolved in 2 L of ethanol to obtain a dark brown solution A. Separately, 1 kg of β-cyclodextrin was mixed with 1 L of water to obtain a paste B. The solution A was put into an empty tank, and the paste B was further introduced while stirring, and then stirred well until uniform, to obtain a skin-colored sol C. After confirming that this skin-colored sol C solidified in a fresh cream state by standing for 5 minutes, it was pulverized with a drum dryer DD-1 manufactured by Chuo Kakoki Co., Ltd. The internal pressure was reduced, the drum surface temperature was set to 95 ° C., the drum was set to 1 revolution / minute, and the sol C solidified in a creamy state was sequentially charged from the upper hopper, and powdered sequentially. First, 1481 g of powder having a uniform yellowish color tone was discharged. The resulting powder was tack-free and a small amount was kneaded with polyethylene gloved hands, but did not lump.
[0031]
Example 6
1 kg of defatted rice bran was extracted with 2 L of ethanol for 2 hours to obtain 14.2 g of an extract (e.g., glycosphingolipid content: 1.41% by weight) after distilling off the solvent. This extract was dissolved in 60 mL of ethanol to obtain a yellow-brown solution A. Separately, 40 g of β-cyclodextrin was mixed with 40 mL of water to obtain Paste B. The paste B was introduced into the solution A with stirring well, and the mixture was stirred well until the mixture became uniform, thereby obtaining a light yellow sol C. After confirming that the sol C was solidified in a fresh cream form by standing for 5 minutes, it was vacuum-dried at 70 ° C. for 8 hours, and then pulverized with a pulverizer (household mill) to obtain a pale yellow uniform 51.8 g of a powder having a color tone were obtained. The resulting powder was tack-free and a small amount was kneaded with polyethylene gloved hands, but did not lump.
[0032]
Comparative Example 1
1 kg of konjac flour powder was extracted with 2 L of ethanol for 2 hours to obtain 10.3 g of the extract after distilling off the solvent (glycosphingolipid content: 6.43% by weight). This extract was dissolved in 100 mL of ethanol to obtain a brown solution A. Separately, 20 g of β-cyclodextrin was mixed with 20 mL of water to obtain Paste B. The paste B was introduced into the solution A while stirring well, and the mixture was stirred well until the mixture became uniform, thereby obtaining a skin-colored sol C. As soon as the stirring was stopped, the flesh-colored sol C precipitated cyclodextrin and separated from the transparent supernatant, and the overall viscosity did not increase. The sol C was vacuum-dried at 70 ° C. for 8 hours, and then pulverized with a pulverizer (a household mill) to obtain 26.6 g of a substance having an ocher, slightly dark and light mottled color tone. On the side, some sticky, non-crushed material was found sticky and sticky. The obtained product was strongly sticky and a small amount was kneaded with a hand wearing polyethylene gloves. However, it became lumpy and could not be returned to the original powder state.
[0033]
Comparative Example 2
1 kg of konjac flour powder was extracted with 2 L of ethanol for 2 hours to obtain 10.3 g of the extract after distilling off the solvent (glycosphingolipid content: 6.43% by weight). This extract was dissolved in 40 mL of ethanol to obtain a brown solution A. Separately, 20 g of corn starch was mixed with 20 mL of water to obtain Paste B. The paste B was introduced into the solution A while stirring well, and the mixture was stirred well until the mixture became uniform, thereby obtaining a skin-colored sol C. As soon as the stirring was stopped, the flesh-colored sol C precipitated corn starch and separated from the clear supernatant, and the overall viscosity did not increase. The sol C was vacuum-dried at 70 ° C. for 8 hours, and then pulverized with a pulverizer (household mill) to obtain 27.2 g of a substance having an ocher, slightly dark and light mottled color tone. On the side, some sticky, non-crushed material was found sticky and sticky. The obtained product was strongly sticky and a small amount was kneaded with a hand wearing polyethylene gloves. However, it became lumpy and could not be returned to the original powder state.
[0034]
Comparative Example 3
1 kg of konjac flour powder was extracted with 2 L of ethanol for 2 hours to obtain 10.3 g of the extract after distilling off the solvent (glycosphingolipid content: 6.43% by weight). This extract was dissolved in 40 mL of tetrahydrofuran to obtain a brown solution A. Separately, 20 g of β-cyclodextrin was mixed with 20 mL of water to obtain Paste B. The paste B was introduced into the solution A while stirring well. However, even if the mixture was sufficiently mixed, the mixture did not become a uniform sol, and irregularly sized lumps of cyclodextrin were settled and the solution floated on the upper part. Was obtained. This sol C was vacuum-dried at 70 ° C. for 8 hours as it was, and then crushed by a crusher (household mill). Did not.
[0035]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to this invention, in powderization of a glycosphingolipid-containing composition, a sticky powder is obtained, which has no conventional problems such as strong stickiness, high adhesion of a surface, and easy formation of lumps. I can do it.

Claims (4)

A glycosphingolipid-containing composition comprising a cyclic oligosaccharide as an excipient and being in powder form. The glycosphingolipid-containing composition according to claim 1, wherein the cyclic oligosaccharide is β-cyclodextrin and / or γ-cyclodextrin. The composition according to claim 1 or 2, wherein the glycosphingolipid-containing composition is obtained by solvent extraction from at least one kind of raw material selected from the group consisting of konjac potato, konjac fine powder, konjac coarse powder and konjac tobi powder. The glycosphingolipid-containing composition according to the above. In a state in which a solvent other than water having the following properties (a) and (b) coexists at a volume ratio of 1/50 or more to water with respect to water, the glycosphingolipid-containing substance and the cyclic oligosaccharide are mixed. The method for producing a glycosphingolipid-containing composition according to any one of claims 1 to 3, wherein the composition is dried after contacting the sugar.
(A) Mutual dissolution with water (b) Inclusion with the cyclic oligosaccharide to be used in the presence of water or in an anhydrous state