Glyceroglycolipid composition, emulsifier, antibacterial agent, food / drink product, production method, and use

Abstract

One purpose of the present invention is to provide a novel, naturally-derived glyceroglycolipid composition.　One aspect of the present invention is a glyceroglycolipid composition comprising a glyceroglycolipid, wherein the glyceroglycolipid includes at least MGMG and DGMG, and the MGMG content is not less than 30 mol% with respect to a total of 100 mol% of the glyceroglycolipid. Furthermore, one aspect of the present invention is a glyceroglycolipid composition comprising digalactosylmonoacylglycerol (DGMG) in an amount of not less than 80 mass% with respect to 100 mass% of solid content.

Description

Glyceroglycolipid composition, emulsifier, antibacterial agent, food and beverage, production method, use

[0001] The present invention relates to a glyceroglycolipid composition, an emulsifier, an antibacterial agent, a food and beverage, a production method, and a use.

[0002] Emulsifiers having the function of uniformly dispersing water and oil play an important role in food processing, and are widely used for purposes such as improving the stability of food and modifying texture. Most of the emulsifiers currently on the market are chemically synthesized products, but with the growing health consciousness of consumers and the preference for natural food, the use of chemically synthesized products is being avoided, and interest in naturally derived emulsifiers is increasing.

[0003] As a naturally derived emulsifier, lecithin is widely known, and lecithin particularly derived from soybean is commonly used. However, soybean-derived lecithin may act as an allergen, and its use may be restricted for consumers with soybean allergy.

[0004] As naturally derived emulsifiers other than lecithin, it is known that some of the cell membrane components ubiquitously present in plants and algae exhibit an emulsifying effect. For example, Patent Document 1 discloses a polar lipid-rich extract obtained or obtainable from macroalgae, microalgae, photosynthetic bacteria, and / or the photosynthetic organ(s) and / or tissue(s) of plants, and combinations thereof.

[0005] Japanese Unexamined Patent Application Publication (Translation of PCT Application) No. 2023-546567

[0006] As described above, soybean-derived lecithin is commonly used as a naturally derived emulsifier, but soybean-derived lecithin may act as an allergen, and its use may be restricted for consumers with soybean allergy. Therefore, there is a demand for the development of emulsifiers using naturally derived components other than soybean.

[0007] In addition, although Patent Document 1 discloses the use of a naturally derived extract as an emulsifier, it is necessary to add a large amount of the extract to obtain an emulsifying effect, and the extract may not function as an emulsifier in food and beverage applications.

[0008] Therefore, one object of the present invention is to provide a novel composition (preferably a naturally derived composition) that can be used as an emulsifier. Another object of the present invention is to provide a novel composition (preferably a naturally derived composition) that can be used as an emulsifier having emulsifying performance suitable for food and beverage applications.

[0009] As a result of diligent research, the inventors discovered that a glycolipid-degrading enzyme-treated product obtained by enzymatically treating a glycolipid extract derived from plants (including algae) with a glyceroglycolipid-degrading enzyme has excellent emulsifying properties, leading to the present invention.

[0010] Therefore, one aspect of the present invention (Invention A) can be expressed as follows.

[0011] [1] A glycerolglycolipid composition comprising glycerolglycolipids, wherein the glycerolglycolipids comprise at least monogalactosylmonocylglycerol (MGMG) and digalactosylmonocylglycerol (DGMG), and the content of MGMG is 30 mol% or more with respect to 100 mol% of the total amount of glycerolglycolipids. [2] The glycerolglycolipid composition according to [1], wherein the glycerolglycolipid composition is a product of a glycolipid-degrading enzyme treatment of a plant-derived glycolipid extract. [3] The glycerolglycolipid composition according to [2], wherein the glycerolglycolipid-degrading enzyme for preparing the product of the glycolipid-degrading enzyme treatment is glycerolglycolipid lipase. [4] The glycerolglycolipid composition according to any one of [1] to [3], wherein the content of MGMG is the highest among the glycerolglycolipids contained in the glycerolglycolipid composition. [5] The glyceroglycolipid composition according to any one of [1] to [4], wherein the total content of glyceroglycolipids in the glyceroglycolipid composition is 10% by mass or more with respect to 100% by mass of solid content. [6] The glyceroglycolipid composition according to any one of [1] to [5], wherein the glyceroglycolipid further comprises, in addition to MGMG and DGMG, at least one selected from monogalactosyldiacylglycerol (MGDG), digalactosyldiacylglycerol (DGDG), sulfoquinovosylmonocylglycerol (SQMG) and sulfoquinovosyldiacylglycerol (SQDG), and the total content of MGMG, MGDG, DGMG, DGDG, SQMG and SQDG is 80 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. [7] The glyceroglycolipid composition according to any one of [1] to [6], wherein the DGMG content in the glyceroglycolipid composition is 1 mol% or more and 40 mol% or less based on 100 mol% of the total amount of the glyceroglycolipids. [8] The glyceroglycolipid composition according to any one of [1] to [7], wherein the DGMG content in the glyceroglycolipid composition is 10 mol% or more and 40 mol% or less based on 100 mol% of the total amount of the glyceroglycolipids.[9] The glyceroglycolipid composition according to any one of [1] to [8], wherein the glyceroglycolipid composition contains SQMG, and the content of SQMG in the glyceroglycolipid composition is 1 mol% or more and 30 mol% or less based on 100 mol% of the total amount of glyceroglycolipids.

[10] The glyceroglycolipid composition according to any one of [2] to [9], wherein the glycolipid extract contains glyceroglycolipids, and the content of MGDG in the glycolipid extract is 30 mol% or more based on 100 mol% of the total amount of glyceroglycolipids.

[11] The glyceroglycolipid composition according to

[10] , wherein the total content of MGDG and DGDG in the glycolipid extract is 50 mol% or more based on 100 mol% of the total amount of glyceroglycolipids.

[12] The glyceroglycolipid composition according to any one of

[10] to

[11] , wherein the constituent fatty acids of the glyceroglycolipid in the glycolipid extract include at least palmitic acid and linolenic acid, and the total content of palmitic acid and linolenic acid is 20 mol% or more with respect to 100 mol% of the total amount of constituent fatty acids.

[13] The glyceroglycolipid composition according to any one of [2] to

[12] , wherein the plant is tea leaves or spirulina.

[14] A method for producing a glyceroglycolipid composition, comprising the steps of preparing a glycolipid extract containing a glyceroglycolipid from a plant using an extraction solvent, and enzymatically treating the glycolipid extract with a glyceroglycolipid-degrading enzyme to obtain a glycolipid-degrading enzyme-treated product.

[15] The method according to

[14] , wherein the glyceroglycolipid-degrading enzyme is glyceroglycolipid lipase.

[16] The method according to any one of

[14] to

[15] , wherein the glyceroglycolipid comprises at least monogalactosyldiacylglycerol (MGDG) and digalactosyldiacylglycerol (DGDG), and the content of MGDG in the glycolipid extract is 30 mol% or more with respect to 100 mol% of the total amount of the glyceroglycolipid.

[17] The method according to

[16] , wherein the total content of MGDG and DGDG in the glycolipid extract is 50 mol% or more with respect to 100 mol% of the total amount of the glyceroglycolipid.

[18] The method according to any one of

[16] to

[17] , wherein the constituent fatty acids of the glycolipid in the glycolipid extract include at least palmitic acid and linolenic acid, and the total content of palmitic acid and linolenic acid is 20 mol% or more with respect to 100 mol% of the total amount of constituent fatty acids.

[19] The method according to any one of

[14] to

[18] , wherein the plant is tea leaves or spirulina.

[20] The method according to any one of

[14] to

[19] , wherein the glycolipid-degrading enzyme-treated product includes at least monogalactosylmonocylglycerol (MGMG) and digalactosylmonocylglycerol (DGMG), and the content of MGMG is 30 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids.

[21] An emulsifier comprising the glyceroglycolipid composition according to any one of [1] to

[13] .

[22] The emulsifier according to

[21] for use in food and beverages.

[23] Food and beverages comprising the emulsifier according to

[22] .

[24] The method according to any one of

[14] to

[20] , wherein the glyceroglycolipid composition is an emulsifier.

[25] Use of the glyceroglycolipid composition according to any one of [1] to

[13] as an emulsifier.

[26] Use according to

[25] , wherein the emulsifier is for food and beverages.

[27] A method for producing food and beverages, comprising the step of adding the glyceroglycolipid composition according to any one of [1] to

[13] to food and beverage ingredients.

[0012] Furthermore, one aspect of the present invention (Invention A) can be expressed as follows.

[0013] [1'] An emulsifier comprising a glycolipid-degrading enzyme-treated product of a plant-derived glycolipid extract, wherein the glycolipid-degrading enzyme-treated product contains glyceroglycolipids, the glyceroglycolipids contain at least MGMG, and the MGMG content is 30 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. [2'] The emulsifier according to [1'], wherein the glyceroglycolipid-degrading enzyme for preparing the glycolipid-degrading enzyme-treated product is glyceroglycolipid lipase. [3'] The emulsifier according to any one of [1'] to [2'], wherein the MGMG content is the highest among the glyceroglycolipids contained in the glycolipid-degrading enzyme-treated product. [4'] The emulsifier according to any one of [1'] to [3'], wherein the total glyceroglycolipid content in the glycolipid-degrading enzyme-treated product is 50% by mass or more with respect to 100% by mass of the solid content. [5'] The emulsifier according to any one of [1'] to [4'], wherein the glyceroglycolipid further comprises MGMG and at least one selected from MGDG, DGMG, DGDG, SQMG, and SQDG, and the total content of MGMG, MGDG, DGMG, DGDG, SQMG, and SQDG is 80 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. [6'] The emulsifier according to any one of [1'] to [5'], wherein the content of DGMG in the glycosphagnum-degrading enzyme-treated product is 1 mol% or more and 40 mol% or less with respect to 100 mol% of the total amount of glyceroglycolipids. [7'] The emulsifier according to any one of [1'] to [6'], wherein the content of SQMG in the glycosphagnum-degrading enzyme-treated product is 1 mol% or more and 30 mol% or less with respect to 100 mol% of the total amount of glyceroglycolipids. [8'] An emulsifier according to any one of [1'] to [7'], wherein the MGDG content in the glycolipid extract is 30 mol% or more based on 100 mol% of the total amount of glyceroglycolipids. [9'] An emulsifier according to any one of [1'] to [8'], wherein the total content of MGDG and DGDG in the glycolipid extract is 50 mol% or more based on 100 mol% of the total amount of glyceroglycolipids. [10'] An emulsifier according to any one of [1'] to [9'], wherein the constituent fatty acids of the glyceroglycolipids in the glycolipid extract include at least palmitic acid and linolenic acid, and the total content of palmitic acid and linolenic acid is 20 mol% or more based on 100 mol% of the total amount of constituent fatty acids.[11'] The emulsifier according to any one of [1'] to [10'], wherein the plant is tea leaves or spirulina. [12'] A method for producing the emulsifier according to any one of [1'] to [11'], comprising the steps of: preparing a glycolipid extract from a plant using an extraction solvent; and enzymatically treating the glycolipid extract with a glyceroglycolipid-degrading enzyme to obtain a glycolipid-degrading enzyme-treated product. [13'] The method according to [12'], wherein the glyceroglycolipid-degrading enzyme is glyceroglycolipid lipase. [14'] The method according to any one of [12'] to [13'], wherein the MGDG content in the glycolipid extract is 30 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. [15'] The method according to any one of [12'] to [14'], wherein the total content of MGDG and DGDG in the glycolipid extract is 50 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. [16'] The method according to any one of [12'] to [15'], wherein the constituent fatty acids of the glycolipid in the glycolipid extract include at least palmitic acid and linolenic acid, and the total content of palmitic acid and linolenic acid is 20 mol% or more with respect to 100 mol% of the total amount of constituent fatty acids. [17'] The method according to any one of [12'] to [16'], wherein the plant is tea leaves or spirulina. [18'] The emulsifier according to any one of [1'] to [11'] for addition to food and beverages.

[0014] On the other hand, the present inventors, after diligent research, have found that by enzymatically treating plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme, digalactosylmonocylglycerol (DGMG) can be produced, and that this DGMG possesses excellent emulsifying properties. Furthermore, they have found that DGMG not only has excellent emulsifying properties but also excellent antibacterial properties. In other words, the present invention provides a composition containing DGMG as an active ingredient that can be used as an emulsifier and / or antibacterial agent.

[0015] Therefore, one aspect of the present invention (Invention B) can be expressed as follows.

[0016]

[28] A glyceroglycolipid composition containing digalactosylmonoacylglycerol (DGMG) in an amount of 80% by mass or more based on 100% by mass of solid content.

[29] The glyceroglycolipid composition according to

[28] , wherein the DGMG is obtained by contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme.

[30] The glyceroglycolipid composition according to

[29] , wherein the glyceroglycolipid-degrading enzyme is a glyceroglycolipid lipase.

[31] The glyceroglycolipid composition according to any one of

[29] to

[30] , wherein the plant is a land plant or algae.

[32] The glyceroglycolipid composition according to any one of

[29] to

[31] , wherein the plant is a cereal.

[33] The glyceroglycolipid composition according to any one of

[29] to

[32] , wherein the plant is oats, wheat, barley, or rye.

[34] A method for producing a glycerolglycolipid composition, comprising the step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glycerolglycolipid-degrading enzyme to produce digalactosylmonoacylglycerol (DGMG).

[35] The method according to

[34] , wherein the glycerolglycolipid-degrading enzyme is a glycerolglycolipid lipase.

[36] The method according to any one of

[34] to

[35] , further comprising the step of extracting and / or purifying DGDG from the plant to obtain DGDG.

[37] The method according to any one of

[34] to

[36] , wherein the plant is a land plant or an algae.

[38] The method according to any one of

[34] to

[37] , wherein the plant is a cereal.

[39] The method according to any one of

[34] to

[38] , wherein the plant is oats, wheat, barley, or rye.

[40] The method according to any one of

[34] to

[39] , further comprising the step of purifying the obtained DGMG.

[41] An emulsifier comprising the glyceroglycolipid composition described in any of

[28] to

[33] .

[42] The emulsifier described in

[41] for addition to food and beverages.

[43] Food and beverages comprising the emulsifier described in

[42] .

[44] The method according to any of

[34] to

[40] , wherein the glyceroglycolipid composition is an emulsifier.

[45] An emulsifier comprising digalactosylmonocylglycerol (DGMG).

[46] An antimicrobial agent comprising digalactosylmonocylglycerol (DGMG).

[47] A method for producing the antimicrobial agent described in

[46] , comprising the step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme to produce digalactosylmonoacylglycerol (DGMG).

[48] The antimicrobial agent described in

[46] for use in food and beverages.

[49] Use as an emulsifier for a glyceroglycolipid composition described in any of

[28] to

[33] .

[50] The use described in

[49] , wherein the emulsifier is for food and beverages.

[51] Use as an antimicrobial agent for a glyceroglycolipid composition described in any of

[28] to

[33] .

[52] The use described in

[51] , wherein the antimicrobial agent is for food and beverages.

[53] A method for producing food and beverages, comprising the step of adding a glyceroglycolipid composition described in any of

[28] to

[33] to food and beverage ingredients.

[0017] Furthermore, one aspect of the present invention (Invention B) can be expressed as follows.

[0018] [1''] An emulsifier containing digalactosylmonoacylglycerol (DGMG). [2''] The emulsifier according to [1''], wherein DGMG is obtained by contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme. [3''] The emulsifier according to [2''], wherein the glyceroglycolipid-degrading enzyme is a glyceroglycolipid lipase. [4''] The emulsifier according to any one of [2''] to [3''], wherein the plant is a land plant or an algae. [5''] The emulsifier according to any one of [2''] to [4''], wherein the plant is a cereal. [6''] The emulsifier according to any one of [2''] to [5''], wherein the plant is oats, wheat, barley, or rye. [7''] A method for producing an emulsifier according to any one of [1''] to [6''], comprising the step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme to produce digalactosylmonoacylglycerol (DGMG). [8''] The method according to [7''], wherein the glyceroglycolipid-degrading enzyme is a glyceroglycolipid lipase. [9''] The method according to any one of [7''] to [8''], further comprising the step of extracting and / or purifying DGDG from a plant to obtain DGDG. [10''] The method according to any one of [7''] to [9''], wherein the plant is a land plant or an algae. [11''] The method according to any one of [7''] to [10''], wherein the plant is a cereal. [12''] The method according to any one of [7''] to [11''], wherein the plant is oats, wheat, barley, or rye. [13''] The method according to any one of [7''] to [12''], further comprising the step of purifying the obtained DGMG. [14''] An emulsifier according to any one of [1''] to [6''] for addition to food and beverages. [15''] An antimicrobial agent comprising digalactosyl monoacylglycerol (DGMG). [16''] A method for producing the antimicrobial agent according to [15''], comprising the step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme to produce digalactosylmonoacylglycerol (DGMG). [17''] The antimicrobial agent according to [15''] for addition to food and beverages.This specification includes the disclosures of Japanese Patent Application No. 2025-068645 and Japanese Patent Application No. 2025-068649, which form the basis of the priority claim of this application.

[0019] According to one aspect of the present invention, a novel composition (preferably a naturally derived composition) that can be used as an emulsifier can be provided. Furthermore, according to one aspect of the present invention, a novel composition (preferably a naturally derived composition) that can be used as an emulsifier having emulsifying properties suitable for food and beverage applications can be provided.

[0020] <<Invention A>> One aspect of the present invention is a glycerolglycolipid composition comprising a glycerolglycolipid, wherein the glycerolglycolipid comprises at least monogalactosylmonocylglycerol (MGMG) and digalactosylmonocylglycerol (DGMG), and the content of MGMG is 30 mol% or more with respect to 100 mol% of the total amount of the glycerolglycolipid.

[0021] The present invention provides a novel composition (preferably a naturally derived composition) that can be used as an emulsifier.

[0022] One aspect of the present invention is an emulsifier comprising a product of a glycosphagnetizing enzyme treatment of a plant-derived glycolipid extract, wherein the product of the glycosphagnetizing enzyme treatment contains glyceroglycolipids, and the glyceroglycolipids contain at least monogalactosylmonocylglycerol (MGMG), and the MGMG content is 30 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids.

[0023] The present invention provides a novel naturally derived emulsifier. In this specification, "naturally derived" means that the emulsifier contains components derived from a natural product or its extract, and is distinguished from those in which all components are produced entirely by chemical synthesis. Examples of natural products include plants (including algae).

[0024] Conventionally, soy-derived lecithin is commonly known as a naturally derived emulsifier. However, soy-derived lecithin can be an allergen, and its use may be limited for consumers with soy allergies. The glycerolglycolipid composition or emulsifier according to the present invention is plant-derived and can provide an emulsifier made from naturally derived ingredients that can replace soy lecithin. In one embodiment, the glycerolglycolipid composition contains as an active ingredient a product of a plant-derived glycolipid extract treated with a glycolipid-degrading enzyme. The enzymatic treatment improves water solubility and can provide excellent emulsifying performance. Therefore, the glycerolglycolipid composition according to the present invention can function sufficiently as an emulsifier in food and beverage applications.

[0025] (Glyceroglycolipid composition or emulsifier) ​​One aspect of the present invention is a glyceroglycolipid composition comprising a glyceroglycolipid, wherein the glyceroglycolipid comprises at least monogalactosylmonocylglycerol (MGMG) and digalactosylmonocylglycerol (DGMG), and the content of MGMG is 30 mol% or more with respect to 100 mol% of the total amount of the glyceroglycolipid.

[0026] The glycerolglycolipid composition according to the present invention has excellent emulsifying properties. Preferably, it is a product of a glycolipid-degrading enzyme treatment of a plant-derived glycolipid extract with a glycerolglycolipid-degrading enzyme. The emulsifier (also referred to as the emulsifier composition) according to the present invention contains the glycerolglycolipid composition according to the present invention as an active ingredient. Preferably, the glycerolglycolipid composition according to the present invention can be produced by enzymatic treatment (e.g., lipase treatment) of a plant-derived glycolipid extract with a glycerolglycolipid-degrading enzyme. Preferably, the glycerolglycolipid composition according to the present invention is a product of a glycolipid-degrading enzyme treatment of a plant-derived glycolipid extract. The glycerolglycolipid composition according to the present invention contains glycerolglycolipids containing MGMG, and the MGMG content in the glycerolglycolipid composition (e.g., the product treated with a glycolipid-degrading enzyme) is 30 mol% or more based on 100 mol% of the total amount of glycerolglycolipids.

[0027] Furthermore, one aspect of the present invention is an emulsifier comprising a product of a plant-derived glycolipid extract treated with a glyceroglycolipid-degrading enzyme, wherein the product of the glyceroglycolipid-degrading enzyme contains glyceroglycolipids, the glyceroglycolipids contain at least monogalactosylmonocylglycerol (MGMG), and the MGMG content is 30 mol% or more based on 100 mol% of the total amount of glyceroglycolipids.

[0028] The emulsifier according to the present invention is an emulsifier in which a product of a glycosphagnum-degrading enzyme treatment of a plant-derived glycolipid extract with a glyceroglycolipid-degrading enzyme is used as an active ingredient. The emulsifier according to the present invention can be produced by enzymatic treatment (e.g., lipase treatment) of a plant-derived glycolipid extract with a glyceroglycolipid-degrading enzyme. Furthermore, in the present invention, the product of the glycosphagnum-degrading enzyme treatment contains glyceroglycolipids including MGMG, and the MGMG content in the product of the glycosphagnum-degrading enzyme treatment is 30 mol% or more based on 100 mol% of the total amount of glyceroglycolipids.

[0029] In the glycerolglycolipid composition according to the present invention (e.g., a product treated with a glycolipid-degrading enzyme), the MGMG content is 30 mol% or more based on 100 mol% of the total amount of glycerolglycolipids. Preferably, the MGMG content is 35 mol% or more, preferably 40 mol% or more, and preferably 45 mol% or more, based on 100 mol% of the total amount of glycerolglycolipids. Furthermore, it is preferable that the MGMG content in the glycerolglycolipid composition be the highest among the glycolipids contained in the product treated with the glycolipid-degrading enzyme. Diacyl-type glycolipids such as MGDG and DGDG have two fatty acids, and tend to have strong hydrophobicity and low water solubility as a whole molecule, making dispersion in water difficult in some cases. On the other hand, MGMG and DGMG have only one fatty acid, so they are highly hydrophilic and have a high affinity for the aqueous phase. As a result, they can exhibit surface activity suitable for oil-in-water emulsification. Furthermore, while it is important for emulsifiers to form a stable film at the water-oil interface, diacyl glycolipids such as MGDG and DGDG have a large hydrophobic group relative to their hydrophilic group, making it difficult for them to efficiently orient at the interface and thus difficult to maintain a stable interface in oil-in-water emulsions. On the other hand, MGMG and DGMG have a large hydrophilic group relative to their hydrophobic group, allowing them to efficiently orient at the interface and thus maintain a stable interface in oil-in-water emulsions.

[0030] In the glyceroglycolipid composition according to the present invention (e.g., a product treated with a glycolipid-degrading enzyme), the MGMG content is not particularly limited, but is preferably 80 mol% or less, preferably 75 mol% or less, and preferably 70 mol% or less, based on 100 mol% of the total amount of glyceroglycolipids. In the glyceroglycolipid composition according to the present invention (e.g., a product treated with a glycolipid-degrading enzyme), the MGMG content is not particularly limited, but is preferably 30 mol% to 80 mol%, preferably 35 mol% to 75 mol%, preferably 40 mol% to 70 mol%, and preferably 45 mol% to 70 mol%, based on 100 mol% of the total amount of glyceroglycolipids.

[0031] In the present invention, the glycerolglycolipid may further include, in addition to MGMG, at least one selected from MGDG, DGMG, DGDG, SQMG, and SQDG. Alternatively, in the present invention, the glycerolglycolipid may further include, in addition to MGMG and DGMG, at least one selected from MGDG, DGDG, SQMG, and SQDG. The total content of MGMG, MGDG, DGMG, DGDG, SQMG, and SQDG is preferably 80 mol% or more, preferably 85 mol% or more, preferably 90 mol% or more, preferably 95 mol% or more, and preferably 99 mol% or more, based on 100 mol% of the glycerolglycolipid. The total content of MGMG, MGDG, DGMG, DGDG, SQMG, and SQDG is preferably 100 mol% or less, preferably 99.9 mol% or less, and preferably 99.5 mol% or less, based on 100 mol% of the glycerolglycolipid.

[0032] In the present invention, the total content of glyceroglycolipids contained in the glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is not particularly limited, but is, for example, 10% by mass or more, preferably 20% by mass or more, preferably 30% by mass or more, preferably 40% by mass or more, preferably 50% by mass or more, preferably 55% by mass or more, preferably 60% by mass or more, preferably 65% ​​by mass or more, preferably 70% by mass or more, preferably 75% by mass or more, preferably 80% by mass or more, preferably 85% by mass or more, preferably 90% by mass or more, and preferably 95% by mass or more. The total content of glyceroglycolipids contained in the glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is not particularly limited, but is, for example, 100% by mass, preferably 99% by mass or less, and preferably 98% by mass or less, based on 100% by mass of solid content. In this specification, "solids" means the solid residue remaining after the solvent has been removed by drying or heat treatment.

[0033] The glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) in the present invention may contain glyceroglycolipids other than MGMG, and may also contain glyceroglycolipids other than MGMG and DGMG. Examples of glyceroglycolipids other than MGMG are not particularly limited, but include digalactosyldiacylglycerol (DGDG), digalactosylmonocylglycerol (DGMG), or sulfoquinovosylmonocylglycerol (SQMG). DGDG is a diacyl type glyceroglycolipid, but it is converted to a monoacyl type glycolipid (DGMG) by enzymatic treatment, so its content decreases compared to before enzymatic treatment. On the other hand, DGMG and SQMG are monoacyl type glyceroglycolipids, and are produced from the corresponding diacyl type glyceroglycolipids (DGDG and SQDG) by enzymatic treatment, so their content increases compared to before enzymatic treatment.

[0034] The DGDG content in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 30 mol% or less, preferably 25 mol% or less, preferably 20 mol% or less, and preferably 15 mol% or less, based on 100 mol% of the total amount of glyceroglycolipids. The DGDG content is preferably, for example, 0.1 mol% or more, and preferably 1 mol% or more, based on 100 mol% of the total amount of glyceroglycolipids. The DGDG content in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 0.1 mol% to 30 mol%, preferably 1 mol% to 25 mol%, preferably 1 mol% to 20 mol%, and preferably 1 mol% to 15 mol%, based on 100 mol% of the total amount of glyceroglycolipids.

[0035] The DGMG content in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 1 mol% or more, preferably 3 mol% or more, preferably 5 mol% or more, and preferably 10 mol% or more, based on 100 mol% of the total amount of glyceroglycolipids. The DGMG content in a glyceroglycolipid composition is preferably 40 mol% or less, preferably 35 mol% or less, and preferably 30 mol% or less, based on 100 mol% of the total amount of glyceroglycolipids. The DGMG content is preferably 1 mol% or more and 40 mol% or less, and more preferably 10 mol% or more and 40 mol% or less, based on 100 mol% of the total amount of glyceroglycolipids. The DGMG content in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 1 mol% to 40 mol%, preferably 3 mol% to 35 mol%, preferably 5 mol% to 30 mol%, and preferably 10 mol% to 30 mol%, based on 100 mol% of the total amount of glyceroglycolipids.

[0036] The SQMG content in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 1 mol% or more, preferably 3 mol% or more, preferably 5 mol% or more, and preferably 10 mol% or more, based on 100 mol% of the total amount of glyceroglycolipids. The SQMG content in a glyceroglycolipid composition is preferably 30 mol% or less, preferably 25 mol% or less, and preferably 20 mol% or less, based on 100 mol% of the total amount of glyceroglycolipids. The SQMG content in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 1 mol% to 30 mol%, preferably 3 mol% to 25 mol%, preferably 5 mol% to 20 mol%, and preferably 10 mol% to 20 mol%, based on 100 mol% of the total amount of glyceroglycolipids.

[0037] The total content of MGMG, DGMG, and SQMG in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 60 mol% or more, 65 mol% or more, 70 mol% or more, preferably 75 mol% or more, preferably 80 mol% or more, and preferably 85 mol% or more, based on 100 mol% of the total amount of glyceroglycolipids. The total content of MGMG, DGMG, and SQMG in a glyceroglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is, for example, 100 mol%, preferably 99 mol% or less, preferably 98 mol% or less, preferably 97 mol% or less, preferably 96 mol% or less, and preferably 95 mol% or less, based on 100 mol% of the total amount of glyceroglycolipids.

[0038] The following describes the structures of MGMG, MGDG, DGDG, DGMG, SQDG, and SQMG.

[0039] Monogalactosylmonoacylglycerol (MGMG) is a type of glyceroglycolipid and consists of the following three main components: a central three-carbon glycerol skeleton, monoacyl (one fatty acid): ester bonded to the sn-1 or sn-2 position of the glycerol, and monogalactose (one galactose): glycosidic bonded to the sn-3 position of the glycerol.

[0040] MGMG is a glyceroglycolipid obtained by removing the fatty acid at the sn-1 or sn-2 position of monogalactosyldiacylglycerol (MGDG).

[0041] Monogalactosyldiacylglycerol (MGDG) is a type of glyceroglycolipid and consists of the following three main components: a central three-carbon glycerol backbone, diacyl (two fatty acids): ester bonds at the sn-1 and sn-2 positions of the glycerol, and monogalactose (one galactose): glycosidic bond at the sn-3 position of the glycerol.

[0042] Digalactosyldiacylglycerol (DGDG) is a type of glyceroglycolipid, which consists of the following three main components: a central three-carbon skeleton glycerol, diacyl (two fatty acids): ester-bonded to the sn-1 position and sn-2 position of glycerol, digalactose (two galactoses): glycosidically bonded to the sn-3 position of glycerol.

[0043] Digalactosylmonoacylglycerol (DGMG) is a type of glyceroglycolipid, which consists of the following three main components: a central three-carbon skeleton glycerol, monoacyl (one fatty acid): ester-bonded to the sn-1 position or sn-2 position of glycerol, digalactose (two galactoses): glycosidically bonded to the sn-3 position of glycerol.

[0044] DGMG is a glyceroglycolipid obtained by removing either the fatty acid at the sn-1 position or the sn-2 position of DGDG.

[0045] Sulfoquinovosyldiacylglycerol (SQDG) is a type of glyceroglycolipid, which consists of the following three main components: a central three-carbon skeleton glycerol, diacyl (two fatty acids): ester-bonded to the sn-1 position and sn-2 position of glycerol, sulfoquinovose: glycosidically bonded to the sn-3 position of glycerol.

[0046] Sulfoquinovosylmonoacylglycerol (SQMG) is a type of glyceroglycolipid, which consists of the following three main components: a central three-carbon skeleton glycerol, monoacyl (one fatty acid): ester-bonded to the sn-1 position or sn-2 position of glycerol, sulfoquinovose: glycosidically bonded to the sn-3 position of glycerol.

[0047] SQMG is a glyceroglycolipid obtained by removing the fatty acid at the sn-1 position or sn-2 position of SQDG.

[0048] The constituent fatty acids of glycolipids are not particularly limited, but are preferably saturated fatty acids or monounsaturated or polyunsaturated fatty acids having 14 to 22 carbon atoms. Examples of saturated fatty acids include myristic acid, palmitic acid, and stearic acid, while examples of unsaturated fatty acids include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, dihomogamma-linolenic acid, octadecatetraenoic acid, arachidonic acid, eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid. The types of constituent fatty acids at positions 1 and 2 of the glycerol backbone in each glycolipid are not particularly limited, and in diacylglycerol-type glycolipids, the two fatty acids may be the same or different.

[0049] Furthermore, each glycolipid may also be in salt form. Examples of such salts include sodium salts and potassium salts.

[0050] The glycerolglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) in the present invention may contain other components besides glycerolglycolipids. Examples of other components include glycolipids other than glycerolglycolipids or free fatty acids. Free fatty acids are not particularly limited, but examples include saturated fatty acids or monounsaturated or polyunsaturated fatty acids having 14 to 22 carbon atoms. Examples of saturated fatty acids include myristic acid, palmitic acid, and stearic acid, while examples of unsaturated fatty acids include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, dihomogamma-linolenic acid, octadecatetraenoic acid, arachidonic acid, eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid.

[0051] The free fatty acid content in the glycerolglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, preferably 5% by mass or less, preferably 3% by mass or less, and preferably 1% by mass or less, based on 100% by mass of solid content. Free fatty acids may be removed by purification or the like. The free fatty acid content in the glycerolglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) is preferably 0% by mass, preferably 0.01% by mass or more, and preferably 0.1% by mass or more, based on 100% by mass of solid content.

[0052] In the preparation of the glycerolglycolipid composition (e.g., a product treated with a glycolipid-degrading enzyme) in the present invention, the glycolipid extract used is preferably such that the MGDG content in the glycolipid extract is 30 mol% or more relative to 100 mol% of the total amount of glycerolglycolipids. A higher MGDG content in the glycolipid extract allows for a higher MGMG content, which is produced by the enzymatic treatment.

[0053] It is preferable that the total content of MGDG and DGDG in the glycolipid extract is 50 mol% or more relative to 100 mol% of the total amount of glyceroglycolipids.

[0054] The constituent fatty acids of the glycolipids in the glycolipid extract preferably include at least palmitic acid and linolenic acid, and the total content of palmitic acid and linolenic acid is preferably 20 mol% or more relative to 100 mol% of the total amount of constituent fatty acids. When the total content of palmitic acid and linolenic acid is above the above lower limit, it is preferable from the viewpoint of substrate recognition and reaction efficiency by glyceroglycolipid-degrading enzymes, particularly glyceroglycolipid lipase. The total content of palmitic acid and linolenic acid is preferably 30 mol% or more, preferably 40 mol% or more, preferably 50 mol% or more, preferably 60 mol% or more, and preferably 70 mol% or more, relative to 100 mol% of the total amount of constituent fatty acids. The total content of palmitic acid and linolenic acid is, for example, 100 mol% or less, preferably 95 mol% or less, and preferably 90 mol% or less, relative to 100 mol% of the total amount of constituent fatty acids. The total content of palmitic acid and linolenic acid is preferably 30 mol% to 100 mol%, 40 mol% to 95 mol%, 50 mol% to 90 mol%, 60 mol% to 90 mol%, and 70 mol% to 90 mol%, based on 100 mol% of the total amount of constituent fatty acids.

[0055] While there are no particular restrictions on the plants used as raw materials for glycolipid extracts, land plants or algae are preferred. Furthermore, the plants are preferably eukaryotes that perform photosynthesis. Glycolipids are abundant in the cell membranes (especially chloroplast membranes) of land plants and algae. From the viewpoint of having a high MGDG content, tea leaves or spirulina can be preferably used as raw materials in this invention. Tea leaves and spirulina are plants rich in MGDG and are therefore preferable as raw materials in this invention. Additionally, since glycolipids can be efficiently obtained from tea leaves and spirulina by general organic solvent extraction, they offer advantages in terms of the simplicity and cost of the extraction process. Furthermore, because tea leaves and spirulina perform photosynthesis, their thylakoid membranes are rich in glycolipids, making them suitable as raw materials for glycolipid extracts. The raw materials may be used individually or in combination of two or more.

[0056] The glycerolglycolipid composition according to the present invention may contain solvents such as water or other components in addition to glycerolglycolipids.

[0057] The emulsifier according to the present invention may contain, or may not contain, a solvent such as water or other components in addition to the glyceroglycolipid composition according to the present invention (e.g., a product treated with a glycolipid-degrading enzyme). In one embodiment, the emulsifier according to the present invention consists of the glyceroglycolipid composition according to the present invention. The content of the glyceroglycolipid composition in the emulsifier according to the present invention is not particularly limited.

[0058] Other components include, for example, emulsifiers other than glyceroglycolipid compositions. These other emulsifiers are not particularly limited, but include, for example, natural emulsifiers such as saponins, plant sterols, lecithin, or enzyme-treated lecithin. Other emulsifiers may also include synthetic emulsifiers such as glycerin fatty acid esters, glycerin acetate fatty acid esters, glycerin lactate fatty acid esters, glycerin succinate fatty acid esters, glycerin diacetyl tartrate fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, sucrose acetate isobutyrate esters, polyglycerin fatty acid esters, polyglycerin condensed ricinoleic acid esters, propylene glycol fatty acid esters, calcium stearoyl lactylate, sodium stearoyl lactylate, or polyoxyethylene sorbitan monoglyceride. However, from the perspective of increasing consumer health consciousness and a preference for natural foods, the emulsifier according to the present invention preferably does not contain synthetic emulsifiers. These may be used individually or in combination of two or more.

[0059] (Uses) The glyceroglycolipid composition according to the present invention is preferably used as an emulsifier. In one embodiment, the emulsifier according to the present invention comprises the glyceroglycolipid composition according to the present invention.

[0060] The glyceroglycolipid composition or emulsifier according to the present invention is not particularly limited, but is preferably used in food and beverage products. In this specification, "food and beverage products" refers to substances that are unlikely to pose a risk to human health and are ingested orally or through the gastrointestinal tract in normal social life, and is not limited to administrative classifications such as food, pharmaceuticals, or quasi-drugs. Therefore, "food and beverage products" in the present invention broadly includes general foods, health foods (functional foods and beverages), health functional foods (foods for specified health uses, nutrient functional foods), quasi-drugs, pharmaceuticals, etc., that are ingested orally.

[0061] Foods and beverages that may contain the glyceroglycolipid composition or emulsifier according to the present invention are not particularly limited, but specific examples include: beverages such as soft drinks, carbonated drinks, nutritional drinks, fruit drinks, and lactic acid drinks (including concentrated stocks and powders for adjusting these beverages); frozen desserts such as ice cream, ice sherbet, and shaved ice; noodles such as soba, udon, vermicelli, gyoza wrappers, shumai wrappers, Chinese noodles, and instant noodles; and candies, chewing gum, chocolate, tablets, and snacks. Examples include confectionery such as sweets, biscuits, jellies, jams, creams, and baked goods; processed seafood and livestock products such as fish cakes, ham, and sausages; dairy products such as processed milk and fermented milk; oils and processed oils such as salad oil, tempura oil, spreads, margarine, mayonnaise, shortening, whipped cream, and dressings; seasonings such as sauces and dips; soups, stews, salads, prepared foods, and pickles; and various other forms of health and nutritional supplements; as well as tablets, capsules, and drinks. When incorporating the glyceroglycolipid composition or emulsifier according to the present invention into these foods and beverages, commonly used auxiliary ingredients and additives can be used in combination.

[0062] In one embodiment, the present invention relates to the use of a glyceroglycolipid composition according to the present invention as an emulsifier. The emulsifier is preferably for use in food and beverages. This can improve the dispersibility of components in food and beverage ingredients, and can form or maintain a good dispersion state in food and beverages where emulsification is required.

[0063] In one embodiment, the present invention relates to a method for producing food and beverages, comprising the step of adding a glyceroglycolipid composition according to the present invention to food and beverage ingredients. The glyceroglycolipid composition is preferably added as an emulsifier. This improves the dispersibility of components in the food and beverage ingredients, and allows for the suitable production of food and beverages requiring emulsification.

[0064] (Method for producing a glycerolglycolipid composition or emulsifier) ​​In one embodiment, the present invention relates to a method for producing a glycerolglycolipid composition, comprising the steps of: preparing a glycolipid extract containing glycerolglycolipids from a plant using an extraction solvent; and enzymatically treating the glycolipid extract with a glycerolglycolipid-degrading enzyme to obtain a glycolipid-degrading enzyme-treated product.

[0065] In one embodiment, the manufacturing method according to the present invention is a method for manufacturing an emulsifier according to the present invention, comprising the steps of preparing a glycolipid extract from a plant using an extraction solvent, and subjecting the glycolipid extract to enzymatic treatment with a glyceroglycolipid-degrading enzyme to obtain a glycolipid-degrading enzyme-treated product.

[0066] In the present invention, the glycerollipid-degrading enzyme is an enzyme that has the property of degrading glycerollipids, and in addition to glycerollipid-degrading (glycerollipid lipase) activity, it may also have glycerophospholipid-degrading (phospholipase) activity and / or triacylglycerol-degrading (triacylglyceride lipase) activity.

[0067] Glycerol-glycolipid-degrading enzymes may be derived from plants or animals, bacterial strains, non-recombinant, or genetically modified, and are not particularly limited as long as they possess glycerol-glycolipid-degrading activity. Furthermore, glycerol-glycolipid-degrading enzymes may be fully purified, partially purified, or not purified at all, and are not particularly limited in terms of the degree of purification, however, from the viewpoint of reaction efficiency, purified enzymes are preferred.

[0068] The glycerolglycolipid-degrading enzyme is preferably a glycerolglycolipid lipase. A glycerolglycolipid lipase is an enzyme that catalyzes the hydrolysis of glycerolglycolipids, for example, by catalyzing the hydrolysis reaction from diacyl-type glycolipids to monoacyl-type glycolipids. This enzyme has the ability to produce monoacyl-type glycolipids or free fatty acids by hydrolyzing the fatty acid ester bond of glycerolglycolipids. For example, by acting on MGDG, MGMG can be produced. MGDG has two fatty acid molecules in the same molecule, but treatment with glycerolglycolipid lipase decomposes one fatty acid molecule, yielding MGMG with only one fatty acid molecule attached. As described above, MGMG has an excellent balance of polarity (hydrophilicity) and nonpolarity (lipophilicity) and high affinity for the aqueous phase, so it can exhibit surface activity suitable for oil-in-water emulsions. Furthermore, because it has one fatty acid and one galactose, its arrangement at the interface is more flexible, making it easier to form a stable emulsion film.

[0069] Glycerolglycolipid lipases are enzymes belonging to the lipase family, originating from specific microorganisms, plants, or animals, and their activity is regulated by conditions such as substrate type, pH, temperature, and the presence of cofactors.

[0070] The glyceroglycolipid lipase may be fully purified, partially purified, or not purified at all, and there are no particular restrictions on the degree of purification, but purified is preferred. The glyceroglycolipid lipase may be a commercially available product, or one obtained by known methods (for example, Japanese Patent Publication No. 2008-206515, Japanese Patent Publication No. 2007-528732, Japanese Patent Publication No. 2008-35867, Japanese Patent Publication No. 2009-527238). Examples of commercially available glyceroglycolipid lipases include Lipopan prime (manufactured by Novonesis).

[0071] The glycerolglycolipid composition according to the present invention can be produced by contacting a glycolipid extract prepared from a plant using an extraction solvent with a glycerolglycolipid-degrading enzyme and subjecting it to enzymatic treatment. Furthermore, the glycolipid-degrading enzyme-treated product, which is the active ingredient of the emulsifier according to the present invention, can be produced by contacting a glycolipid extract prepared from a plant using an extraction solvent with a glycerolglycolipid-degrading enzyme and subjecting it to enzymatic treatment.

[0072] The various conditions such as temperature, solvent, pH, time, and concentration in the step of contacting the glycolipid extract with glyceroglycolipid-degrading enzyme can be appropriately selected by those skilled in the art. For example, the temperature is, for instance, 20 to 50°C. Examples of solvents include water, alcohol (e.g., ethanol or butanol), or mixtures thereof. The pH is, for example, 4 to 10. The reaction can be stopped, for example, by increasing the temperature or by adding a reaction terminating agent such as hydrochloric acid. The reaction can be carried out as appropriate, for example, until the hydrolysis reaction is completed.

[0073] In the present invention, an enzyme-treated product obtained by enzymatic treatment of a glycolipid extract may be further subjected to purification and / or processing to prepare a glycolipid-degrading enzyme-treated product which is an active ingredient of the glyceroglycolipid composition or emulsifier according to the present invention. For example, free fatty acids and impurities may be removed by purification. Examples of processing treatments include drying, and more specifically, freeze-drying.

[0074] In this specification, "extraction" means the operation of obtaining a glycolipid extract (glycolipid fraction) from plant raw materials using an extraction solvent. The glycolipid extract preferably contains a large amount of MGDG, and the MGDG content in the glycolipid extract is preferably 30% by mass or more based on 100% by mass of the total amount of glycolipids. The extraction operation may be appropriately adjusted to include a large amount of MGDG.

[0075] In this specification, "purification" means the process of removing unwanted components and increasing the concentration of the desired component.

[0076] As mentioned above, there are no particular restrictions on the plants used as raw materials, but tea leaves or spirulina can be preferably used.

[0077] The extraction process is not particularly limited and can be carried out according to conventional methods. For example, the extraction process can be carried out by drying the plant material, then crushing it as is or using a crusher, and then subjecting it to extraction with an extraction solvent. Drying can be done in the sun or using a commonly used drying machine.

[0078] The raw materials may be used as is, or they may be washed with water before use. For example, plant residue after extracting water-soluble functional or nutrient components may be used.

[0079] As the extraction solvent, a polar solvent is preferred, such as water, a hydrophilic organic solvent (e.g., alcohol), or a mixture thereof. The extraction solvent may be used alone or in combination of two or more, or a non-polar solvent may be mixed in. Furthermore, the extraction solvent is preferably used at room temperature or below the boiling point of the solvent.

[0080] Water that can be used as an extraction solvent includes pure water, tap water, well water, mineral water, hot spring water, spring water, fresh water, etc., as well as water that has undergone various treatments. Treatments applied to water include, for example, purification, heating, sterilization, filtration, ion exchange, osmotic pressure adjustment, and buffering. Therefore, water that can be used as an extraction solvent also includes purified water, hot water, ion-exchanged water, physiological saline, phosphate buffer, phosphate-buffered physiological saline, etc.

[0081] Examples of hydrophilic organic solvents that can be used as extraction solvents include lower aliphatic alcohols having 1 to 5 carbon atoms, such as methanol, ethanol, propyl alcohol, and isopropyl alcohol; lower aliphatic ketones having acetone and methyl ethyl ketone; and polyhydric alcohols having 2 to 5 carbon atoms, such as 1,3-butylene glycol, propylene glycol, and glycerin. Ethanol is preferred as the alcohol due to its safety and the purity of the glycolipids. Examples of nonpolar solvents that can be used in combination as hydrophilic solvents include hexane and chloroform.

[0082] When using a mixture of two or more polar solvents as an extraction solvent, the mixing ratio can be adjusted as appropriate. For example, when using a mixture of water and a lower aliphatic alcohol as an extraction solvent, the mixing ratio of water to the lower aliphatic alcohol is preferably 9:1 to 1:9 (volume ratio), and more preferably 75:5 to 2:8 (volume ratio). When using a mixture of water and a lower aliphatic ketone, the mixing ratio of water to the lower aliphatic ketone is preferably 9:1 to 2:8 (volume ratio), and when using a mixture of water and a polyhydric alcohol, the mixing ratio of water to the polyhydric alcohol is preferably 5:5 to 1:9 (volume ratio).

[0083] In one embodiment, from the viewpoint of efficiently extracting glycolipids without extracting neutral lipids, 60-80% ethanol can be used as the extraction solvent.

[0084] The extraction process is not particularly limited as long as it allows the soluble components contained in the raw material to be eluted into the extraction solvent, and can be carried out according to conventional methods. For example, the raw material can be immersed in an extraction solvent in an amount 5 to 15 times (by mass ratio) that of the raw material, and the soluble components can be extracted at room temperature or under reflux heating. After extraction, the extract can be obtained by filtering to remove the extraction residue. From the obtained extract, components such as chlorophyll can be removed using activated carbon or the like as needed, and the solvent can be removed by distillation to obtain a paste-like concentrate. Further drying of this concentrate can yield a dried product.

[0085] In the present invention, the method for extracting glycolipid fractions from plant raw materials is not particularly limited. For example, a total lipid-containing fraction can be obtained from plant raw materials (preferably in powder form) by the Bridyyer method, and then neutral lipid fractions, glycolipid fractions, and phospholipid fractions can be obtained from the total lipid-containing fraction by column chromatography. The Bridyyer method is a method for efficiently separating and extracting lipids using a polar solvent (a mixture of methanol, chloroform, and water). Lipids dissolve in the chloroform layer (organic phase), and non-lipid components dissolve in the aqueous phase. By adjusting the amounts of water and chloroform, the organic phase containing lipids (lipid-soluble components) and the aqueous phase (non-lipid components) can be separated. As an example of a method using the Bridyyer method, first, plant raw materials (e.g., in powder form) are suspended in methanol and chloroform (e.g., 2:1, v / v), and if necessary, the raw materials are finely dispersed using sonication or a homogenizer to facilitate the elution of lipids. Next, a solvent such as water is added as needed to adjust the ratio of chloroform:methanol:water (for example, 1:1:0.9 (v / v / v)). This forms two phases (an organic layer and an aqueous layer). Next, the chloroform layer (organic layer) containing lipids and the aqueous phase (non-lipid components) are separated by centrifugation or decantation, and the lower organic layer (chloroform layer) containing lipids is recovered. Then, the chloroform is removed using a rotary evaporator or nitrogen gas, and the total lipid fraction is recovered. Next, different types of lipids (neutral lipids, glycolipids, and phospholipids) are separated from the extracted total lipid fraction by column chromatography. By holding components with different lipid affinities in the column (stationary phase) and sequentially washing them with a mixed solvent of chloroform / methanol / acetone, different lipids (three types of lipid fractions) can be separated. Typically, neutral lipids elute first, glycolipids elute next, and phospholipids elute last. For separation, solvent conditions include, for example, eluting neutral lipids with chloroform or chloroform / methanol (e.g., 9:1). Eluting glycolipids with, for example, acetone or acetone / methanol (e.g., 9:1 to 4:1). Eluting phospholipids with methanol. Neutral lipids include triglycerides (TG) and free fatty acids, while phospholipids are major components of cell membranes and are highly polar.

[0086] The solvent used for extraction is not particularly limited and may include, for example, water, ethyl acetate, acetone, chloroform, alcohol (e.g., methanol, ethanol, propanol, isopropanol), or a mixture thereof. An example of a mixed solvent is a mixture of methanol and chloroform. Based on the mixing ratio of various solvent combinations, the various components contained in the glycolipid fraction loaded onto the column can be eluted stepwise.

[0087] The obtained glycolipid fraction can be dried to remove the solvent, if necessary.

[0088] The glycolipid extract after drying may be dissolved in a suitable solvent. Examples of solvents include 30-60% ethanol. After dissolution, a glycolipid-degrading enzyme can be added, and the enzymatic reaction can be carried out under predetermined conditions to obtain a glycolipid-degrading enzyme-treated product. While the glycolipid-degrading enzyme is not particularly limited, glyceroglycolipid lipase can be used. The temperature of the enzymatic reaction can be, for example, room temperature.

[0089] The enzyme reaction conditions are not particularly limited once the reaction proceeds, but preferably, the conditions are such that the glycolipid substrate dissolves and the enzyme is not deactivated. The enzyme reaction is preferably carried out in 30-60% ethanol. The reaction temperature is not particularly limited, but considering the stability of the enzyme, it is desirable to keep it below 50°C. The enzyme reaction may be carried out after extraction and removal of the raw materials, or it may be carried out without removal.

[0090] The glycolipid-degrading enzyme-treated product obtained after the enzymatic reaction can be deactivated by appropriate treatment such as heat treatment. For example, heating at 65°C or higher for 10 minutes can effectively deactivate the enzyme's activity, but the deactivation conditions can be appropriately changed depending on the properties of the enzyme.

[0091] Furthermore, the processed material can be subjected to purification treatment, and can be purified using solvents as appropriate. For example, free fatty acids and fatty acid ethyl esters can be efficiently removed by adding an equal amount of a solvent such as n-hexane. Alternatively, free fatty acids and fatty acid ethyl esters can be removed using ion exchange resins or synthetic adsorbents.

[0092] Furthermore, the glycolipid-degrading enzyme-treated product may be solidified by drying. For example, by freeze-drying the treated product, a solid (e.g., powder) glycolipid-degrading enzyme-treated product can be obtained.

[0093] The resulting composition has high water solubility and excellent emulsifying properties, making it useful as an emulsifier, particularly in food and beverage applications.

[0094] <<Invention B>> One aspect of the present invention is a glyceroglycolipid composition containing digalactosylmonocylglycerol (DGMG) in an amount of 80% by mass or more based on 100% by mass of solid content.

[0095] The present invention provides a novel composition (preferably a naturally derived composition) that can be used as an emulsifier. The glyceroglycolipid composition according to the present invention contains a high content of DGMG and can therefore exhibit excellent emulsifying properties.

[0096] One aspect of the present invention is an emulsifier containing digalactosylmonoacylglycerol (DGMG).

[0097] The present invention provides a novel emulsifier derived from natural sources.

[0098] Conventionally, soy-derived lecithin has been commonly known as a naturally derived emulsifier. However, soy-derived lecithin can be an allergen, and its use may be restricted for consumers with soy allergies. The glyceroglycolipid composition (or emulsifier) ​​according to the present invention contains DGMG as an active ingredient and can provide an emulsifier made from naturally derived ingredients that can replace soy lecithin.

[0099] Furthermore, while DGDG, a type of glyceroglycolipid, has been conventionally known as a naturally derived substance exhibiting a certain degree of emulsifying ability, DGDG itself has low water solubility and does not function adequately as an emulsifier in food and beverage applications. On the other hand, DGMG, the active ingredient of the glyceroglycolipid composition (or emulsifier) ​​according to the present invention, has higher water solubility and superior emulsifying performance than DGDG. DGDG (diacyl type) has two fatty acid chains and is therefore relatively hydrophobic, while DGMG (monoacyl type) has only one fatty acid chain and is therefore more hydrophilic than DGDG. Considering the hydrophilic-hydrophobic balance, DGMG is more suitable for emulsion formation and is more likely to exhibit stable emulsifying action. In other words, DGMG has improved affinity with the aqueous phase, thus improving its performance as an oil-in-water type emulsifier. Therefore, DGMG can function adequately as an emulsifier in food and beverage applications.

[0100] Furthermore, DGMG, the active ingredient of the glyceroglycolipid composition (or emulsifier) ​​according to the present invention, also exhibits excellent antibacterial properties. Therefore, it functions as an emulsifier in food and beverage applications and also shows antibacterial activity that contributes to improving the shelf life of food and beverages. As a result, DGMG can be used not only as a food additive but also as an antibacterial agent.

[0101] (Glyceroglycolipid composition or emulsifier) ​​One aspect of the present invention is a glyceroglycolipid composition containing digalactosylmonoacylglycerol (DGMG) in an amount of 80% by mass or more based on 100% by mass of solid content. The glyceroglycolipid composition according to the present invention has excellent emulsifying properties.

[0102] One aspect of the present invention is an emulsifier containing digalactosylmonoacylglycerol (DGMG).

[0103] The emulsifier according to the present invention is an emulsifier containing DGMG as an active ingredient.

[0104] DGMG can be produced by enzymatic treatment (specifically, lipase treatment) of the naturally derived ingredient digalactosyldiacylglycerol (DGDG).

[0105] Digalactosyldiacylglycerol (DGDG) is a type of glyceroglycolipid and consists of the following three main components: a central three-carbon glycerol skeleton, diacyl (two fatty acids): ester bonds at the sn-1 and sn-2 positions of the glycerol, and digalactose (two galactoses): glycosidic bond at the sn-3 position of the glycerol.

[0106] Digalactosylmonocylglycerol (DGMG) is a type of glyceroglycolipid and consists of the following three main components: a central three-carbon glycerol skeleton; monoacyl (one fatty acid): esterified at the sn-1 or sn-2 position of the glycerol; digalactose (two galactoses): glycosidically linked at the sn-3 position of the glycerol.

[0107] DGMG is a glyceroglycolipid in which either the sn-1 or sn-2 fatty acid of DGDG has been removed.

[0108] The constituent fatty acids of glycolipids are not particularly limited, but are preferably saturated fatty acids or monounsaturated or polyunsaturated fatty acids having 14 to 22 carbon atoms. Examples of saturated fatty acids include myristic acid, palmitic acid, and stearic acid, while examples of unsaturated fatty acids include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, dihomogamma-linolenic acid, octadecatetraenoic acid, arachidonic acid, eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid. The types of constituent fatty acids at positions 1 and 2 of the glycerol backbone in each glycolipid are not particularly limited, and in diacylglycerol-type glycolipids, the two fatty acids may be the same or different. From the viewpoint of oxidative stability, unsaturated fatty acids with two or fewer double bonds are preferred.

[0109] In the glyceroglycolipid composition (or emulsifier) ​​according to the present invention, a high purity of DGMG is preferable from the viewpoint of emulsification. The DGMG content in the glyceroglycolipid composition according to the present invention is 80% by mass or more based on 100% by mass of solid content. High purity of DGMG reduces the presence of impurities that hinder emulsification. The DGMG content in the glyceroglycolipid composition (or emulsifier) ​​according to the present invention is not particularly limited, but is preferably 80% by mass or more, preferably 85% by mass or more, preferably 90% by mass or more, and preferably 95% by mass or more, based on 100% by mass of solid content in the glyceroglycolipid composition (or emulsifier). Furthermore, the DGMG content in the glyceroglycolipid composition (or emulsifier) ​​according to the present invention is preferably 80% by mass or more, preferably 85% by mass or more, preferably 90% by mass or more, and preferably 95% by mass or more, based on 100% by mass of the total amount of glycolipids (or glyceroglycolipids).

[0110] DGMG, the active ingredient in the glyceroglycolipid composition (or emulsifier) ​​according to the present invention, is highly water-soluble and possesses excellent emulsifying properties, making it useful as an emulsifier in food and beverage applications. Furthermore, DGMG, the active ingredient in the glyceroglycolipid composition (or emulsifier) ​​according to the present invention, also exhibits excellent antibacterial activity, thus functioning as an emulsifier in food and beverage applications while also demonstrating antibacterial activity that contributes to improving the shelf life of food and beverages. As a result, DGMG can be used not only as a food additive but also as an antibacterial agent.

[0111] The glyceroglycolipid composition (or emulsifier) ​​according to the present invention may contain solvents such as water or other components in addition to DGMG. Other components include, for example, emulsifiers other than DGMG. Other emulsifiers are not particularly limited, but include natural emulsifiers such as saponins, plant sterols, lecithin, or enzyme-treated lecithin. Other emulsifiers may also include synthetic emulsifiers such as glycerin fatty acid esters, glycerin acetate fatty acid esters, glycerin lactate fatty acid esters, glycerin succinate fatty acid esters, glycerin diacetyl tartrate fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, sucrose acetate isobutyrate esters, polyglycerin fatty acid esters, polyglycerin condensed ricinoleic acid esters, propylene glycol fatty acid esters, calcium stearoyl lactylate, sodium stearoyl lactylate, or polyoxyethylene sorbitan monoglyceride. However, from the viewpoint of increasing consumer health consciousness and a preference for natural foods, it is preferable that the emulsifier according to the present invention does not contain synthetic emulsifiers. These may be used individually or in combination of two or more types.

[0112] (Antibacterial agent) The glyceroglycolipid composition (or emulsifier) ​​according to the present invention contains DGMG as an active ingredient, and as shown in this embodiment, DGMG has been found to have superior antibacterial activity compared to other naturally derived emulsifiers. Therefore, one aspect of the present invention is an antibacterial agent containing digalactosylmonocylglycerol (DGMG).

[0113] (Uses) The glyceroglycolipid composition, emulsifier, or antibacterial agent according to the present invention are not particularly limited, but are preferably used in food and beverage products. In this specification, "food and beverage products" refers to substances that are unlikely to endanger human health and are ingested orally or through the gastrointestinal tract in normal social life, and is not limited to administrative classifications such as food, pharmaceuticals, or quasi-drugs. Therefore, "food and beverage products" in the present invention broadly includes general foods, health foods (functional foods and beverages), health functional foods (foods for specified health uses, nutritional functional foods), quasi-drugs, pharmaceuticals, etc., that are ingested orally.

[0114] The foods and beverages that may contain the glyceroglycolipid composition, emulsifier, or antibacterial agent according to the present invention are not particularly limited, but specific examples include: beverages such as soft drinks, carbonated drinks, nutritional drinks, fruit drinks, and lactic acid drinks (including concentrated stocks and powders for adjusting these beverages); frozen desserts such as ice cream, ice sherbet, and shaved ice; noodles such as soba, udon, vermicelli, gyoza wrappers, shumai wrappers, Chinese noodles, and instant noodles; candy, chewing gum, chocolate, tablets, and snacks. Examples include confectionery such as sweets, biscuits, jellies, jams, creams, and baked goods; processed seafood and livestock products such as fish cakes, ham, and sausages; dairy products such as processed milk and fermented milk; oils and processed foods such as salad oil, tempura oil, spreads, margarine, mayonnaise, shortening, whipped cream, and dressings; seasonings such as sauces and dips; soups, stews, salads, prepared foods, and pickles; and various other forms of health and nutritional supplements; as well as tablets, capsules, and drinks. When incorporating the glyceroglycolipid composition, emulsifier, or antibacterial agent according to the present invention into these foods and beverages, commonly used auxiliary ingredients and additives can be used in combination.

[0115] In one embodiment, the present invention relates to the use of the glyceroglycolipid composition according to the present invention as an emulsifier. The emulsifier is preferably for food and beverage use. This improves the dispersibility of components in food and beverage ingredients, and allows for the formation or maintenance of a good dispersion state in food and beverages where emulsification is required. In one embodiment, the present invention relates to the use of the glyceroglycolipid composition according to the present invention as an antibacterial agent. The antibacterial agent is preferably for food and beverage use. This allows for the suitable production of food and beverages that may have antibacterial properties. In one embodiment, the present invention relates to the use of the glyceroglycolipid composition according to the present invention as both an emulsifier and an antibacterial agent. The emulsifier and antibacterial agent are preferably for food and beverage use. This improves the dispersibility of components in food and beverage ingredients, and allows for the suitable production of food and beverages that may have antibacterial properties.

[0116] In one embodiment, the present invention relates to a method for producing food and beverages, comprising the step of adding a glyceroglycolipid composition according to the present invention to food and beverage ingredients. The glyceroglycolipid composition according to the present invention can be added as an emulsifier. This can improve the dispersibility of components in food and beverage ingredients, and allow for the suitable production of food and beverages requiring emulsification. Furthermore, the glyceroglycolipid composition according to the present invention can be added as an antibacterial agent. This can allow for the suitable production of food and beverages that may have antibacterial properties. Furthermore, the glyceroglycolipid composition according to the present invention can be added as both an emulsifier and an antibacterial agent. This can improve the dispersibility of components in food and beverage ingredients and allow for the suitable production of food and beverages that may have antibacterial properties.

[0117] (Method for producing glycerolglycolipid compositions, emulsifiers, or antibacterial agents) In one embodiment, the method for producing a glycerolglycolipid composition according to the present invention is a method for producing a glycerolglycolipid composition, comprising the step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glycerolglycolipid-degrading enzyme to produce digalactosylmonocylglycerol (DGMG).

[0118] In one embodiment, the manufacturing method according to the present invention is a method for manufacturing an emulsifier according to the present invention, comprising the step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme to produce digalactosylmonoacylglycerol (DGMG).

[0119] In one embodiment, the manufacturing method according to the present invention is a method for manufacturing an antimicrobial agent according to the present invention, comprising the step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme to produce digalactosylmonoacylglycerol (DGMG).

[0120] The manufacturing method according to the present invention includes a step of contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme (e.g., glyceroglycolipid lipase) to produce digalactosylmonoacylglycerol (DGMG).

[0121] DGDG is plant-derived. "Plant-derived" means that it is derived from plants or their extracts.

[0122] In the present invention, the glycerollipid-degrading enzyme is an enzyme that has the property of degrading glycerollipids, and in addition to glycerollipid-degrading (glycerollipid lipase) activity, it may also have glycerophospholipid-degrading (phospholipase) activity and / or triacylglycerol-degrading (triacylglyceride lipase) activity.

[0123] Glycerol-glycolipid-degrading enzymes may be derived from plants or animals, microorganisms, non-recombinant, or genetically modified, and are not particularly limited as long as they possess glycerol-glycolipid-degrading activity. Furthermore, glycerol-glycolipid-degrading enzymes may be fully purified, partially purified, or not purified at all, and are not particularly limited in terms of the degree of purification, however, from the viewpoint of reaction efficiency, purified enzymes are preferred.

[0124] The glycerolglycolipid-degrading enzyme is preferably a glycerolglycolipid lipase. A glycerolglycolipid lipase refers to an enzyme that catalyzes the hydrolysis of glycerolglycolipids, for example, by catalyzing the hydrolysis reaction from diacyl-type glycolipids to monoacyl-type glycolipids. This enzyme has the ability to produce monoacyl-type glycolipids or free fatty acids by hydrolyzing the fatty acid ester bonds of glycerolglycolipids. In particular, by acting on DGDG, it can produce digalactosylmonocylglycerol (DGMG).

[0125] Glycerolglycolipid lipases are enzymes belonging to the lipase family derived from specific microorganisms, plants, or animals, and their activity is regulated by conditions such as substrate type, pH, temperature, and the presence of cofactors. In this invention, efficient production is made possible by using a glycerolglycolipid lipase that has the property of hydrolyzing DGDG to produce DGMG.

[0126] The glyceroglycolipid lipase may be fully purified, partially purified, or not purified at all, and there are no particular restrictions on the degree of purification, but purified is preferred. The glyceroglycolipid lipase may be a commercially available product, or one obtained by known methods (for example, Japanese Patent Publication No. 2008-206515, Japanese Patent Publication No. 2007-528732, Japanese Patent Publication No. 2008-35867, Japanese Patent Publication No. 2009-527238). Examples of commercially available glyceroglycolipid lipases include Lipopan prime (manufactured by Novonesis).

[0127] Furthermore, the glycerolglycolipid-degrading enzyme used in the present invention preferably has high tolerance to alcohol and preferably exhibits high activity against glycerolglycolipids even in alcoholic solutions. It is also preferable that it can degrade plant (including algae) extracts without pH adjustment, so it is preferable that it is active in the weakly acidic to neutral range of pH 4 to pH 8. When the glycerolglycolipid-degrading activity at the optimal pH is taken as 100%, the glycerolglycolipid-degrading activity at pH 4 to 8 is 50% or more, preferably 60% or more, more preferably 70% or more, and when the glycerophospholipid-degrading activity at the optimal pH is taken as 100%, the glycerophospholipid-degrading activity at pH 4 to 8 is 50% or more, preferably 60% or more.

[0128] Furthermore, the lipid-degrading activity of the lipid-degrading enzyme used in this invention, such as that of glyceroglycolipids, can be measured by the following method. Specifically, 1.0 g of digalactosyldiacylglycerol (DGDG) is gradually added to 50 ml of a 4 wt% Triton X-100 aqueous solution (manufactured by Sigma-Aldrich Japan Co., Ltd.) that has been preheated to 37°C, and stirred until completely dissolved. A mixture of this substrate solution (210 μl) and 30 μl of 400 mM OPS (manufactured by Nacalai Tesque) pH 6.0 buffer is incubated at 37°C for 5 minutes, then 30 μl of the enzyme solution is added and uniformly dispersed, and then incubated at 37°C for 10 minutes. 30 μl of 1N hydrochloric acid is added to this reaction mixture to stop the enzymatic reaction, and then this solution is colorimetrically quantified using NEFA-HR (manufactured by Fujifilm Wako). One unit of enzyme is defined as the amount of enzyme that produces 1 μmol of free fatty acid per minute. If the equipment used for this method is unavailable, similar measurement equipment may be used. Furthermore, the measurement conditions can be appropriately modified depending on the enzyme used.

[0129] DGDG contains two fatty acid molecules within the same molecule, but treatment with glyceroglycolipid lipase breaks down one fatty acid molecule, yielding DGMG, which has only one fatty acid molecule attached. This change increases the hydrophilicity of DGMG compared to DGDG, improving its emulsifying power in water-rich environments. Furthermore, due to its high hydrophilicity, DGMG is easily soluble in water and can efficiently bind to the cell surface of bacteria that grow in water. Because of these characteristics, DGMG is expected to exert antibacterial activity.

[0130] The manufacturing method according to the present invention includes a step of contacting digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme (preferably a glyceroglycolipid lipase) to produce digalactosylmonocylglycerol (DGMG). The active ingredient, DGMG, can be produced by hydrolyzing digalactosyldiacylglycerol (DGDG).

[0131] The temperature, solvent, pH, time, and concentration in the process of contacting DGDG with glyceroglycolipid-degrading enzyme to produce DGMG can be appropriately selected by those skilled in the art. For example, the temperature is, for instance, 30 to 40°C. Examples of solvents include water, alcohol (e.g., ethanol or butanol), or mixtures thereof. The pH is, for example, 4 to 10. The reaction can be stopped, for example, by increasing the temperature or by adding a reaction terminating agent such as hydrochloric acid. The reaction can be carried out as appropriate, for example, until the reaction from DGDG to DGMG is complete.

[0132] The manufacturing method according to the present invention may further include the step of extracting and / or purifying DGDG from a plant to obtain DGDG.

[0133] One method for extracting DGDG is to obtain a DGDG-containing fraction from a plant-derived raw material containing DGDG using an extraction solvent. The DGDG-containing fraction may be, for example, a glycolipid fraction.

[0134] After extraction, purification may be performed as needed to remove impurities and unwanted components. Purification can improve the concentration / purity of the target component. For example, purification can improve the concentration of DGDG from the extracted glycolipid fraction. The DGDG content in the purified product after purification is preferably 80% by mass or more, preferably 85% by mass or more, preferably 90% by mass or more, and preferably 95% by mass or more, based on 100% by mass of the total amount of glycolipids (e.g., glyceroglycolipids).

[0135] In one embodiment of the present invention, DGMG can be obtained by contacting a DGDG-containing fraction extracted and / or purified from a raw material containing DGDG with a glyceroglycolipid-degrading enzyme (e.g., glyceroglycolipid lipase).

[0136] The raw material plant is not particularly limited as long as it contains DGDG, but preferably it is a land plant or algae. Furthermore, the plant is preferably a photosynthetic eukaryote. DGDG is abundant in the cell membranes (especially chloroplast membranes) of land plants and algae. As for land plants, grains are preferred from the viewpoint of having a high DGDG content, and preferred grains include oats, wheat, barley, and rye. As for algae, various types of algae such as green algae, red algae, brown algae, and diatoms are preferred, and from the viewpoint of having a high DGDG content, Chlorella, Spirulina, Euglena, Schizoides, Volvox, Euglena, Ulva, and Porphyra are preferred. The raw material may also be a plant-derived extract. The raw material may be used alone or in combination of two or more types.

[0137] As natural ingredients containing DGDG, plant extracts may be used, and it is preferable to use extracts from land plants or algae. As plant extracts, wheat oil is a preferred example, and wheat germ oil, barley oil, and oat oil are also preferred.

[0138] The method for extracting and purifying DGDG from plants is not particularly limited and can be carried out according to conventional methods. For example, the extraction process can be carried out by drying the plant material, then crushing it as is or using a crusher, and then subjecting it to extraction with an extraction solvent. Drying can be done in the sun or using a commonly used drying machine.

[0139] The raw materials may be used as is, or they may be washed with water before use. For example, plant residue after extracting water-soluble functional or nutrient components may be used.

[0140] As the extraction solvent, a polar solvent is preferred, such as water, hydrophilic organic solvents (e.g., alcohol), or a mixture thereof. Nonpolar solvents can also be used in combination for extraction. The extraction solvent may be used alone or in combination of two or more. Furthermore, the extraction solvent is preferably used at room temperature or below its boiling point.

[0141] Water that can be used as an extraction solvent includes pure water, tap water, well water, mineral water, hot spring water, spring water, fresh water, etc., as well as water that has undergone various treatments. Treatments applied to water include, for example, purification, heating, sterilization, filtration, ion exchange, osmotic pressure adjustment, and buffering. Therefore, water that can be used as an extraction solvent also includes purified water, hot water, ion-exchanged water, physiological saline, phosphate buffer, phosphate-buffered physiological saline, etc.

[0142] Examples of hydrophilic organic solvents that can be used as extraction solvents include lower aliphatic alcohols having 1 to 5 carbon atoms, such as methanol, ethanol, propyl alcohol, and isopropyl alcohol; lower aliphatic ketones having acetone and methyl ethyl ketone; and polyhydric alcohols having 2 to 5 carbon atoms, such as 1,3-butylene glycol, propylene glycol, and glycerin. Ethanol is preferred as the alcohol due to its safety and the purity of the glycolipids.

[0143] When using a mixture of two or more polar solvents as an extraction solvent, the mixing ratio can be adjusted as appropriate. For example, when using a mixture of water and a lower aliphatic alcohol as an extraction solvent, the mixing ratio of water to the lower aliphatic alcohol is preferably 9:1 to 1:9 (volume ratio), and more preferably 7:3 to 2:8 (volume ratio). When using a mixture of water and a lower aliphatic ketone, the mixing ratio of water to the lower aliphatic ketone is preferably 9:1 to 2:8 (volume ratio), and when using a mixture of water and a polyhydric alcohol, the mixing ratio of water to the polyhydric alcohol is preferably 5:5 to 1:9 (volume ratio).

[0144] In one embodiment, from the viewpoint of efficiently extracting glycolipids without extracting neutral lipids, 60-80% ethanol can be used as the extraction solvent.

[0145] The extraction process is not particularly limited as long as it allows the soluble components contained in the raw material to be eluted into the extraction solvent, and can be carried out according to conventional methods. For example, the raw material can be immersed in an extraction solvent in an amount 5 to 15 times (by mass ratio) that of the raw material, and the soluble components can be extracted at room temperature or under reflux heating. After extraction, the extract can be obtained by filtering to remove the extraction residue. From the obtained extract, components such as chlorophyll can be removed using activated carbon or the like as needed, and the solvent can be removed by distillation to obtain a paste-like concentrate. Further drying of this concentrate can yield a dried product.

[0146] The method for purifying DGDG from the extract, concentrate, or dried extract obtained as described above is not particularly limited and can be carried out by conventional methods. For example, the extract can be dissolved in a developing solvent and subjected to column chromatography using a porous material such as silica gel or alumina, or a porous resin such as styrene-divinylbenzene copolymer or polymethacrylate, to recover the fraction containing DGDG. In this case, the developing solvent can be appropriately selected according to the stationary phase used, but for example, when separating the extract by normal-phase chromatography using silica gel as the stationary phase, a developing solvent such as chloroform:methanol:water = 40:10:0.1 can be used. Furthermore, the fraction containing DGDG obtained by column chromatography may be purified using any organic compound purification method such as reverse-phase silica gel chromatography using ODS, recrystallization, liquid-liquid countercurrent extraction, or column chromatography using ion exchange resin. This purification method can also be applied to DGMG in the same way.

[0147] In the present invention, the method for extracting and / or purifying DGDG from plant raw materials is not particularly limited. For example, a total lipid-containing fraction can be obtained from plant raw materials (preferably in powder form) by the Bridyyer method, and then a neutral lipid fraction, a glycolipid fraction, and a phospholipid fraction can be obtained from the total lipid-containing fraction by column chromatography. The glycolipid fraction obtained thereby contains DGDG. The Bridyyer method is a method for efficiently separating and extracting lipids using a polar solvent (a mixture of methanol, chloroform, and water). Lipids dissolve in the chloroform layer (organic phase), and non-lipid components dissolve in the aqueous phase. By adjusting the amounts of water and chloroform, the organic phase containing lipids (lipid-soluble components) and the aqueous phase (non-lipid components) can be separated. As an example of a method using the Bridyyer method, first, plant raw materials (e.g., in powder form) are suspended in methanol and chloroform (e.g., 2:1, v / v), and if necessary, sonication or homogenization is used to finely disperse the raw materials and facilitate the elution of lipids. Next, a solvent such as water is added as needed to adjust the ratio of chloroform:methanol:water (for example, 1:1:0.9 (v / v / v)). This forms two phases (an organic layer and an aqueous layer). Next, the chloroform layer (organic layer) containing lipids and the aqueous phase (non-lipid components) are separated by centrifugation or decantation, and the lower organic layer (chloroform layer) containing lipids is recovered. Then, the chloroform is removed using a rotary evaporator or nitrogen gas, and the total lipid fraction is recovered. Next, different types of lipids (neutral lipids, glycolipids, and phospholipids) are separated from the extracted total lipid fraction by column chromatography. By holding components with different lipid affinities in the column (stationary phase) and sequentially washing them with a mixed solvent of chloroform / methanol / acetone, different lipids (three types of lipid fractions) can be separated. Typically, neutral lipids elute first, glycolipids elute next, and phospholipids elute last. For separation, solvent conditions include, for example, eluting neutral lipids with chloroform or chloroform / methanol (e.g., 9:1); eluting glycolipids with acetone or acetone / methanol (e.g., 9:1 to 4:1); and eluting phospholipids with methanol.Neutral lipids include triglycerides (TG) and free fatty acids, while phospholipids are major components of cell membranes and are highly polar.

[0148] Furthermore, DGDG may be purified from this glycolipid fraction. As described above, for example, the extract can be dissolved in a developing solvent and subjected to column chromatography using a porous material such as silica gel or alumina, or a porous resin such as styrene-divinylbenzene copolymer or polymethacrylate, to recover the fraction containing DGDG. In this case, the developing solvent can be appropriately selected according to the stationary phase used. Furthermore, the fraction containing DGDG obtained by column chromatography may be purified using any organic compound purification method such as reverse-phase silica gel chromatography using ODS, recrystallization, liquid-liquid countercurrent extraction, or column chromatography using ion exchange resin. This purification method can also be applied to DGMG.

[0149] The extract can be purified using, for example, a hydrophobic column and a polar solvent. Specifically, the obtained DGDG-containing extract is dissolved in a 50% to 75% ethanol solution and injected into a hydrophobic chromatography resin. Then, elution is performed stepwise using different water-ethanol mixture ratios. First, water-soluble substances that do not adsorb to the resin are eluted in the 50% to 75% ethanol solution, and then lipid-soluble substances such as glycolipids are eluted in the subsequent ethanol solution of 85% or higher (or an organic solvent such as acetone).

[0150] The solvents used for extraction and purification are not particularly limited and include, for example, water, ethyl acetate, acetone, chloroform, alcohols (e.g., methanol, ethanol, propanol, isopropanol), or mixtures thereof. An example of a mixture is a mixture of methanol and chloroform. Based on the mixing ratio of various solvent combinations, the various components contained in the glycolipid fraction loaded onto the column can be eluted stepwise.

[0151] In the present invention, it is preferable to increase the purity of DGDG subjected to hydrolysis treatment by extraction and / or purification steps. By increasing the purity of DGDG, the conversion efficiency to DGMG can be improved, and the purity of the resulting DGMG can also be increased, resulting in excellent emulsifying or antibacterial activity. The glyceroglycolipid composition (or emulsifier) ​​according to the present invention has a high purity of DGMG, which reduces the presence of impurities that hinder the emulsifying and / or antibacterial activity.

[0152] The obtained DGDG can be dried to remove the solvent if necessary.

[0153] The dried DGDG may be dissolved in a suitable solvent. Examples of solvents include 30-60% ethanol. After dissolution, DGMG can be obtained by adding a glyceroglycolipid-degrading enzyme and carrying out an enzymatic reaction under predetermined conditions. While the glyceroglycolipid-degrading enzyme is not particularly limited, glyceroglycolipid lipase can be used. The temperature of the enzymatic reaction can be, for example, room temperature to 40°C.

[0154] The enzyme reaction conditions are not particularly limited once the reaction proceeds, but preferably, the substrate DGDG is dissolved and the enzyme is not deactivated. The enzyme reaction is preferably carried out in 30-60% ethanol. The reaction temperature is not particularly limited, but considering the stability of the enzyme, it is desirable to keep it below 40°C. The enzyme reaction may be carried out after extraction and removal of the raw materials, or it may be carried out without removal.

[0155] The disappearance of DGDG and the generation of DGMG due to the enzymatic reaction can be confirmed, for example, by thin-layer chromatography or high-performance liquid chromatography. In thin-layer chromatography, after spotting the sample onto a silica gel plate, the sample is developed using a solvent mixture of chloroform, methanol, ammonia, acetic acid, acetone, water, etc., in appropriate proportions. The components are then identified by heating after spraying with reagents such as sulfuric acid, phosphomolybdenum reagent, and anthrone reagent to cause color development.

[0156] The reaction solution containing DGMG obtained after the enzymatic reaction can be deactivated by appropriate treatment such as heat treatment. For example, the enzyme's activity can be effectively deactivated by heating at 65°C or higher for 10 minutes.

[0157] Furthermore, the obtained DGMG can be purified as needed, using a solvent as appropriate. For example, free fatty acids and fatty acid ethyl esters can be efficiently removed by adding an equal amount of a solvent such as n-hexane.

[0158] Furthermore, the obtained DGMG may be solidified by drying. For example, the solvent can be removed by freeze-drying the DGMG-containing solution, thereby obtaining solid DGMG (e.g., in powder form).

[0159] The glyceroglycolipid composition (or emulsifier) ​​according to the present invention is useful as an emulsifier in food and beverage applications because its active ingredient, DGMG, has excellent water solubility and superior emulsifying performance. Furthermore, DGMG, the active ingredient of the glyceroglycolipid composition (or emulsifier) ​​according to the present invention, also has excellent antibacterial properties, thus functioning as an emulsifier in food and beverage applications while also exhibiting antibacterial activity that contributes to improving the shelf life of food and beverages. As a result, DGMG can be used not only as a food additive but also as an antibacterial agent.

[0160] The present invention will be described more specifically below based on examples. However, the present invention is not limited to these examples.

[0161] <<Example A>> <Preparation of glycolipid extract (glycolipid fraction)> Glycolipid extract (glycolipid fraction) was prepared from various raw materials. The raw materials used were tea leaves (green tea leaves), nannochloropsis, oat oil (seed extract), and spirulina (all in powder or pulverized form).

[0162] The total lipid fraction was extracted from various raw materials using the Bligh-Dyer method. The obtained total lipid fraction was adsorbed onto a silica gel stationary phase, and the neutral lipid fraction was eluted with chloroform / acetone (4:1, v / v), followed by the glycolipid fraction, which was then recovered.

[0163] <Preparation of Enzyme-Treated Products> The recovered glycolipid fraction (acetone fraction) was dried and then dissolved in 50% ethanol by volume. Glyceroglycolipid lipase was added to this solution, and the enzymatic reaction was carried out at room temperature to obtain enzymatic hydrolysates. The obtained enzymatic hydrolysates were heat-treated at 65°C for 10 minutes to inactivate the enzyme. Then, an equal amount of n-hexane was added to 50% ethanol by volume, and the free fatty acids and fatty acid ethyl esters were partitioned into the n-hexane layer and removed. The resulting lower layer of treated liquid was freeze-dried to prepare the enzyme-treated glycolipid products.

[0164] <Analysis of Lipid Classes> To evaluate the lipid classes of the glycolipid fractions, the glycolipid fractions were subjected to silica gel thin-layer chromatography (TLC) after acetone elution and subsequent lyophilization. Using chloroform / methanol / water (65:16:2, v / v) as the TLC developing solvent, the glycolipid fractions were fractionated into the following components: monogalactosyldiacylglycerol (MGDG) fraction; monogalactosylmonocylglycerol (MGMG) fraction; digalactosyldiacylglycerol (DGDG) fraction; digalactosylmonocylglycerol (DGMG) fraction; sulfoquinovosyldiacylglycerol (SQDG) fraction; sulfoquinovosylmonocylglycerol (SQDG) fraction.

[0165] Furthermore, the glycolipid fractions (enzyme-treated products) after enzyme treatment were similarly subjected to TLC analysis and fractionated into the following components: fatty acid-like low molecular weight fraction; monogalactosyldiacylglycerol (MGDG) fraction; monogalactosylmonocylglycerol (MGMG) fraction; digalactosyldiacylglycerol (DGDG) fraction; digalactosylmonocylglycerol (DGMG) fraction; sulfoquinovosyldiacylglycerol (SQDG) fraction; sulfoquinovosylmonocylglycerol (SQMG) fraction.

[0166] The quantitative analysis of each fraction and the analysis of its fatty acid composition were performed using fatty acid methyl esters (FAMEs) derived from each fraction. Specifically, nonadecanoic acid (C19:0) was added as an internal standard to each fraction, dissolved in acetylmethanol chloride solution, and heated at 100°C for 2 hours to perform acid hydrolysis and fatty acid methylation. Subsequently, the prepared FAMEs were quantified using gas chromatography-flame ionization detector (GC-FID) equipped with a CP-Sil 88 column for FAME analysis. As a result of the analysis, Table 1 shows the molar ratios of MGDG, DGDG, and SQDG in the glycolipid fractions derived from each raw material (before enzymatic treatment), and Table 2 shows the molar ratios of fatty acid-like low molecular weights, MGMG, DGDG, DGMG, and SQMG fractions in the enzymatically treated product (glycolipid fraction after enzymatic treatment).

[0167] Note that C14:0 represents myristic acid, C16:0 represents palmitic acid, C16:1 represents palmitoleic acid, C18:0 represents stearic acid, C18:1 represents oleic acid, C18:2 represents linoleic acid, C18:3(n-3) represents alpha-linolenic acid, C18:3(n-6) represents gamma-linolenic acid, C20:4 represents arachidonic acid, and C20:5 represents eicosapentaenoic acid.

[0168]

[0169]

[0170]

[0171] C16:0 (palmitic acid) and C18:3 (alpha-linolenic acid) together accounted for 78.8%.

[0172]

[0173] C16:0 (palmitic acid) and C18:3 (γ-linolenic acid) together accounted for 79.7%.

[0174]

[0175] The combined content of C16:0 (palmitic acid) and C18:3 (alpha-linolenic acid) was 7.3%.

[0176]

[0177] The combined percentage of C16:0 (palmitic acid) and C18:3 (alpha-linolenic acid) was 18.2%.

[0178] <Evaluation of Emulsifying Power> The sample before enzymatic hydrolysis (glycolipid extract) and the sample after enzymatic hydrolysis (enzyme-treated product) of the obtained glycolipid fraction were dissolved in water to a final concentration of 0.3% by mass. Next, canola oil was added to these solutions to a final concentration of 5% by mass, and homogenization was performed at 65°C for 5 minutes at 9,000 rpm. The treated samples were stored at 25°C for 1 day, and the emulsification state was observed visually and evaluated according to the following criteria: +++: Large clumps of oil droplets are floating; ++: Oil droplets are floating separated into several small clumps; +: Fine oil droplets are floating; -: No oil droplets are observed floating.

[0179]

[0180] <Evaluation Results> The results of this test showed that glycolipid-degrading enzyme-treated products with an MGMG content of 30% by mass or more exhibited superior emulsifying power.

[0181] <<Example B>> In this example, DGMG (digalactosylmonoacylglycerol) was produced, an emulsification test was performed, the critical micelle concentration was measured, and an antimicrobial test was conducted.

[0182] [Example] (Preparation of DGMG) Oat oil was dissolved in chloroform and methanol in a 1:1 ratio and purified by silica gel chromatography. The fraction containing DGDG was separated and freeze-dried to obtain DGDG.

[0183] The obtained DGDG was dissolved in 50% ethanol to a concentration of 2% (W / V), and glyceroglycolipid lipase (derived from Aspergillus japonicus) was used as the DGDG decomposition activity to achieve a concentration of 90–300 units / g per solid content. The reaction was carried out at room temperature for 1 to 7 days, and after confirming the disappearance of the DGDG peak, the enzyme was inactivated by heating at 65°C for 10 minutes. The liberated fatty acids and fatty acid ethyl were extracted and removed from the enzyme reaction solution by adding an equal to three times the amount of n-hexane, and the aqueous layer was dried to obtain DGMG (digalactosylmonoacylglycerol). The DGMG content in the obtained composition was 80% by mass or more relative to 100% by mass of the solid content. Specifically, the glycolipid composition was analyzed by high-performance liquid chromatography (HPLC). Specifically, a YMC-Pack C8 column (150 × 4.6 mm, S-5 μm, pore size 12 nm, manufactured by YMC) was used, and measurements were performed under conditions of column temperature 40°C and flow rate 0.8 mL / min. CAD was used for detection. The eluents used were acetone / tetrahydrofuran (9:1, v / v) as solvent A and water as solvent B, and the analysis was performed under gradient conditions. In the obtained chromatogram, the peak area corresponding to each glycolipid was calculated, and the composition ratio was determined based on the ratio of the peak area of ​​each component to the total peak area. As a result, in this example, the proportion of the peak area corresponding to DGMG was approximately 97% of the total peak area.

[0184] The decomposition of DGDG and the formation of DGMG were confirmed by thin-layer chromatography. After spotting the sample onto a silica gel plate, it was developed with chloroform:methanol:ammonia = 65:35:5, dried, and then sprayed with phosphomolybdenum reagent and heat-treated to develop the color. The enzymatic reaction was carried out until the DGDG spots disappeared.

[0185] (Emulsification Test) The obtained DGMG was dissolved in water to the specified concentration, canola oil was added to make a 5% (w / w) mixture, and homogenization was performed at 65°C for 5 minutes at 9,000 rpm. After storage at 25°C for 2-3 days, the emulsification was observed visually and evaluated according to the following criteria. The results are shown in Table 8. +++: Floats in clumps ++: Floats in several separated clumps +: Floats in small pieces -: None

[0186] As a reference example or comparative example, the same procedure and evaluation were carried out as in the emulsification test described above, except that untreated DGDG or a commercially available emulsifier was used instead of DGMG.

[0187]

[0188] S-1170 and P-1670 are sucrose fatty acid esters widely used in the food industry. DGMG showed excellent emulsifying performance comparable to these sucrose fatty acid esters. Furthermore, DGMG showed superior emulsifying performance compared to DGDG, SLP White (lecithin), and SLP White Lyso (lysolecithin).

[0189] (Measurement of Critical Micelle Concentration (CMC)) The surface tension and critical micelle concentration (CMC) of DGMG were measured using a surface tension meter K100 (KRUSS). The measurements were performed using desalinated water as the dosing solution and a 0.05% DGMG solution as the Vessel solution, and the temperature was maintained at 20°C. For each concentration, measurements were taken for 1 minute at each point, and the average of 10 measurements was calculated. The results are shown in Table 9.

[0190] As a reference or comparative example, the critical micelle concentration of commercially available emulsifiers was also measured in a similar manner, and the results are shown in Table 9.

[0191]

[0192] In Table 9, Poem DM-100 (diglycerin monomyristate), L-7D, L-1695, and P-1670 are commercially available synthetic surfactants. The results in Table 9 show that the critical micelle concentration (CMC) of DGMG is 10 mg / L, indicating emulsifying performance equivalent to or better than that of commercially available synthetic surfactants. Furthermore, DGMG showed superior emulsifying performance compared to SLP White Lyso (lysolecithin).

[0193] Furthermore, the surface tension of DGMG above the CMC is 34 mN / m, which is lower than that of SLP white lyso (36 mN / m), and is considered to have a certain advantage in terms of emulsification stability. This suggests that the emulsifier according to the present invention has sufficient emulsification performance compared to other naturally derived emulsifiers in food and beverage applications. The emulsifier according to the present invention is suitable for use in food and beverage applications.

[0194] (Antibacterial test) The obtained DGMG was dissolved in water, passed through a 0.45 μm filter, and added to sterile Triptycase soy broth (TSB medium) to a final concentration of 50 ppm. Bacillus subtilis subsp. Spizizenii NBRC3134, which had been cultured in advance on standard agar medium, was added to 10 2 The culture medium was added to achieve a cfu / well concentration, and cultured with shaking at 37°C in a 96-well plate with a volume of 150 μL. The turbidity of the culture medium was measured over time, and the time at which bacterial growth began and the OD660 value exceeded 0.05 was recorded. The results are shown in Table 10.

[0195] As a reference example or comparative example, the same treatment and evaluation were carried out as in the above antimicrobial test, except that a commercially available emulsifier was used instead of DGMG. DGDG was not used in the antimicrobial test because it did not dissolve in water.

[0196]

[0197] As shown in Table 10, the growth initiation time (OD660 > 0.05) of Bacillus subtilis subsp. Spizizenii NBRC3134 was delayed to 15.5 hours in the test group treated with DGMG, compared to the commercially available emulsifiers lysolecithin (10.0 hours) and P-1670: sucrose fatty acid ester (13.0 hours). This indicates that DGMG has a certain antibacterial effect and inhibits bacterial growth.

[0198] The antibacterial effect of DGMG was more pronounced compared to lysolecithin and sucrose fatty acid esters, and in particular, approximately two times the growth delay was observed compared to the untreated test group (8.0 hours). Therefore, DGMG is also useful as an antibacterial agent. In particular, in food and beverage applications, DGMG is expected to improve the shelf life of food and beverages through its antibacterial action, in addition to its function as a naturally derived emulsifier.

[0199] The results above clearly show that DGMG has the function of an emulsifier and also exhibits antibacterial activity that contributes to improving the shelf life of food and beverages. This suggests that DGMG can be used not only as a food additive but also as an antibacterial agent.

[0200] All references cited throughout this application are incorporated into this application by reference.

[0201] The upper and / or lower limits of the numerical ranges described herein can be arbitrarily combined to define a preferred range. For example, the upper and lower limits of the numerical ranges can be arbitrarily combined to define a preferred range, the upper limits of the numerical ranges can be arbitrarily combined to define a preferred range, and the lower limits of the numerical ranges can be arbitrarily combined to define a preferred range.

[0202] Those skilled in the art can use the above description to make the most of this disclosure. The claims and embodiments disclosed herein are merely descriptive and illustrative and should be construed as not limiting the scope of this disclosure in any way. With the help of this disclosure, modifications to the details of the embodiments described above can be made without departing from the basic principles of this disclosure. In other words, various modifications and improvements to the embodiments specifically disclosed above are within the scope of this disclosure.

[0203] Although this embodiment has been described in detail above, the specific configuration is not limited to this embodiment, and any design changes that do not depart from the gist of this disclosure are also included in this disclosure.

Claims

A glycerolglycolipid composition containing glycerolglycolipids, The glyceroglycolipid comprises at least monogalactosylmonocylglycerol (MGMG) and digalactosylmonocylglycerol (DGMG), A glyceroglycolipid composition in which the MGMG content is 30 mol% or more based on 100 mol% of the total amount of the glyceroglycolipids. 　 The glycerolglycolipid composition according to claim 1, wherein the glycerolglycolipid composition is a product of a glycosphagnum enzyme treatment of a plant-derived glycolipid extract. 　 The glycerolglycolipid composition according to claim 2, wherein the glyceroglycolipid-degrading enzyme for preparing the aforementioned glycolipid-degrading enzyme-treated product is a glyceroglycolipid lipase. The glycerolglycolipid composition according to claim 1, wherein the MGMG content is the highest among the glycerolglycolipids contained in the glycerolglycolipid composition. 　 The glycerolglycolipid composition according to claim 1, wherein the total content of glycerolglycolipids in the glycerolglycolipid composition is 10% by mass or more based on 100% by mass of solid content. 　 The glyceroglycolipid composition according to claim 1, wherein the glyceroglycolipid further comprises, in addition to MGMG and DGMG, at least one selected from monogalactosyldiacylglycerol (MGDG), digalactosyldiacylglycerol (DGDG), sulfoquinovosylmonocylglycerol (SQMG), and sulfoquinovosyldiacylglycerol (SQDG), and the total content of MGMG, MGDG, DGMG, DGDG, SQMG, and SQDG is 80 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. 　 The glycerolglycolipid composition according to claim 1, wherein the DGMG content in the glycerolglycolipid composition is 1 mol% or more and 40 mol% or less based on 100 mol% of the total amount of the glycerolglycolipids. 　 The glycerolglycolipid composition according to claim 1, wherein the DGMG content in the glycerolglycolipid composition is 10 mol% or more and 40 mol% or less based on 100 mol% of the total amount of the glycerolglycolipids. 　 The glycerolglycolipid composition according to claim 1, wherein the glycerolglycolipid composition contains SQMG, and the content of SQMG in the glycerolglycolipid composition is 1 mol% or more and 30 mol% or less based on 100 mol% of the total amount of glycerolglycolipids. 　 The glycerolglycolipid composition according to claim 2, wherein the glycolipid extract contains glyceroglycolipids, and the MGDG content in the glycolipid extract is 30 mol% or more based on 100 mol% of the total amount of glyceroglycolipids. 　 The glyceroglycolipid composition according to claim 10, wherein the total content of MGDG and DGDG in the glycolipid extract is 50 mol% or more based on 100 mol% of the total amount of the glyceroglycolipid. 　 The constituent fatty acids of the glyceroglycolipid in the glycolipid extract include at least palmitic acid and linolenic acid. The glyceroglycolipid composition according to claim 10, wherein the total content of palmitic acid and linolenic acid is 20 mol% or more based on 100 mol% of the total amount of constituent fatty acids. 　 The glyceroglycolipid composition according to claim 2, wherein the plant is tea leaves or spirulina. A step of preparing a glycolipid extract containing glyceroglycolipids from plants using an extraction solvent, and A process to obtain a glycosphatase-treated product by enzymatically treating a glycolipid extract with a glyceroglycolipid-degrading enzyme. A method for producing a glyceroglycolipid composition containing [a specific substance]. 　 The method according to claim 14, wherein the glycerolglycolipid-degrading enzyme is a glycerolglycolipid lipase. 　 The glyceroglycolipid comprises at least monogalactosyldiacylglycerol (MGDG) and digalactosyldiacylglycerol (DGDG), The method according to claim 14, wherein the content of MGDG in the glycolipid extract is 30 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. 　 The method according to claim 16, wherein the total content of MGDG and DGDG in the glycolipid extract is 50 mol% or more with respect to 100 mol% of the total amount of the glyceroglycolipids. 　 The constituent fatty acids of the glycolipid in the glycolipid extract include at least palmitic acid and linolenic acid. The method according to claim 16, wherein the total content of palmitic acid and linolenic acid is 20 mol% or more based on 100 mol% of the total amount of constituent fatty acids. 　 The method according to claim 14, wherein the plant is tea leaves or spirulina. 　 The method according to claim 14, wherein the glycolipid-degrading enzyme-treated product comprises at least monogalactosylmonocylglycerol (MGMG) and digalactosylmonocylglycerol (DGMG), and the content of MGMG is 30 mol% or more with respect to 100 mol% of the total amount of glyceroglycolipids. 　 An emulsifier comprising the glyceroglycolipid composition according to any one of claims 1 to 13. 　 An emulsifier according to claim 21, for use in food and beverages. 　 Food and beverages comprising the emulsifier described in claim 22. 　 The method according to any one of claims 14 to 20, wherein the glyceroglycolipid composition is an emulsifier. 　 Use as an emulsifier for the glyceroglycolipid composition according to any one of claims 1 to 13. 　 The use according to claim 25, wherein the emulsifier is for use in food and beverages. 　 A method for producing food and beverages, comprising the step of adding a glyceroglycolipid composition according to any one of claims 1 to 13 to food and beverage ingredients. A glyceroglycolipid composition containing digalactosylmonoacylglycerol (DGMG) in an amount of 80% by mass or more based on 100% by mass of solid content. 　 The glyceroglycolipid composition according to claim 28, wherein the DGMG is obtained by contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme. 　 The glycerolglycolipid composition according to claim 29, wherein the glycerolglycolipid-degrading enzyme is a glycerolglycolipid lipase. The glyceroglycolipid composition according to claim 29, wherein the plant is a land plant or an algae. 　 The glyceroglycolipid composition according to claim 29, wherein the plant is a type of cereal. 　 The glyceroglycolipid composition according to claim 29, wherein the plant is oats, wheat, barley, or rye. A process to produce digalactosyl monoacylglycerol (DGMG) by contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme. A method for producing a glyceroglycolipid composition containing [a specific substance]. 　 The method according to claim 34, wherein the glycerolglycolipid-degrading enzyme is a glycerolglycolipid lipase. 　 The method according to claim 34, further comprising the step of extracting and / or purifying DGDG from the aforementioned plant to obtain DGDG. 　 The method according to claim 34, wherein the plant is a land plant or an algae. 　 The method according to claim 34, wherein the plant is a type of cereal. 　 The method according to claim 34, wherein the plant is oats, wheat, barley, or rye. The method according to claim 34, further comprising the step of purifying the obtained DGMG. 　 An emulsifier comprising the glyceroglycolipid composition according to any one of claims 28 to 33. 　 An emulsifier according to claim 41 for use as an additive in food and beverages. 　 Food and beverages comprising the emulsifier described in claim 42. 　 The method according to any one of claims 34 to 40, wherein the glyceroglycolipid composition is an emulsifier. 　 An emulsifier containing digalactosylmonoacylglycerol (DGMG). An antibacterial agent containing digalactosylmonoacylglycerol (DGMG). 　 A method for producing the antimicrobial agent described in claim 46, A process to produce digalactosyl monoacylglycerol (DGMG) by contacting plant-derived digalactosyldiacylglycerol (DGDG) with a glyceroglycolipid-degrading enzyme. Methods that include... 　 The antimicrobial agent according to claim 46, for use as an additive in food and beverages. 　 Use as an emulsifier for the glyceroglycolipid composition according to any one of claims 28 to 33. 　 The use according to claim 49, wherein the emulsifier is for use in food and beverages. 　 Use of the glyceroglycolipid composition according to any one of claims 28 to 33 as an antimicrobial agent. 　 The use of the antibacterial agent according to claim 51, wherein the antibacterial agent is for use in food and beverages. 　 A method for producing food and beverages, comprising the step of adding a glyceroglycolipid composition according to any one of claims 28 to 33 to food and beverage ingredients.

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