CN115500394A

CN115500394A - Fatty acid ester composition containing LPLa triglyceride

Info

Publication number: CN115500394A
Application number: CN202211159791.3A
Authority: CN
Inventors: 张永久; 孙健; 石丹; 高鹏; 李媛媛; 潘健存; 蒋士龙; 石红丽
Original assignee: Heilongjiang Feihe Dairy Co Ltd
Current assignee: Heilongjiang Feihe Dairy Co Ltd
Priority date: 2022-09-22
Filing date: 2022-09-22
Publication date: 2022-12-23

Abstract

The present invention relates to a fatty acid ester composition comprising OPL triglyceride, OPO triglyceride, OOL triglyceride, OLL triglyceride and LPLa triglyceride, wherein the LPLa triglyceride content is 0.5-2 mass% based on the total mass of the triglycerides in the composition. The fatty acid ester composition has reasonable fatty acid proportion, has a grease structure very close to that of breast milk, can be fully digested and absorbed by human bodies, can provide nutrition to the maximum extent, and can be added into special dietary food such as reconstitutable food and the like and infant food such as infant milk powder and the like.

Description

Fatty acid ester composition containing LPLa triglyceride

Technical Field

The invention belongs to the field of food, and particularly relates to a fatty acid ester composition containing LPLa triglyceride, more particularly to a fat composition capable of being sufficiently digested and absorbed, and food containing or using the composition, especially an infant dairy product.

Background

The lipid is a substance necessary for the growth process of infants, can provide 40-50% of energy required for the rapid growth of infants, and is also an important component of the bodies of the infants. The lipid mass fraction in newborns is about 11%, and the lipid mass fraction will increase to around 25% in the following months. Because breast-feeding is always the first choice and gold standard for infant feeding, the research on breast-milk fat always belongs to the hot spot in the field of breast-milk research, when the breast milk is insufficient or the breast-feeding cannot be carried out due to some reasons, the infant formula food is an ideal choice, and in addition, the breast-milk fat component analogue is also prepared into a special diet which is easy to digest and absorb, so that the infant formula food is suitable for some people with weak gastrointestinal functions.

Breast milk has been shown to contain about 4.0% to 4.5% lipids, with about 98% Triglycerides (TG), about 1% phospholipids, and about 0.5% cholesterol and cholesterol esters. In recent years, the nutritional value and physiological function of a series of fatty acids in breast milk, such as oleic acid (O), palmitic acid (P), linoleic acid (L) and linolenic acid (Ln) (essential fatty acids), docosahexaenoic acid (DHA) and Arachidonic Acid (AA), have been studied intensively. The structure of human milk fat is characterized in that saturated fatty acids such as palmitic acid are mainly distributed at Sn-2 position of triglyceride, while unsaturated fatty acids such as oleic acid are mainly distributed at Sn-1,3 position of triglyceride, and due to this special fatty acid distribution, the most abundant triglyceride content in human milk fat is 1,3-dioleic acid-2-palmitic acid triglyceride (OPO), 1-oleic acid-2-palmitic acid-3-linoleic acid triglyceride (OPL), and the like. It is generally believed that triglycerides of this structure (especially the type and content of the 2-position structure) are closely related to fat digestion, absorption and metabolism in infants and young children. In addition, breast milk lipids contain medium-and long-carbon chain triglycerides (MLCT) in addition to OPO triglycerides and OPL triglycerides. At present, the fat sources in infant formula are mainly as follows: mixing vegetable blend oil, cow milk fat or structure oil OPO.

Although the lipid content of cow milk is similar to that of breast milk, the fatty acid compositions of cow milk and breast milk are greatly different, and in the components such as cow milk fat, palmitic acid is distributed on Sn-1 and Sn-3 of triglyceride, namely POP structure. After the POP structural ester enters a human body, free palmitic acid ester is formed under the hydrolysis action of pancreatic lipase, calcium soap is easily formed with calcium ions in food, calcium and energy loss is caused, the utilization degree is poor, constipation of infants is easily caused, and the health of the infants is not facilitated. In addition, the proportion of saturated fatty acids in cow milk is higher than that in cow milk, and the proportion of unsaturated fatty acids and free fatty acids in cow milk is higher than that in cow milk.

Although vegetable oils are mainly present in the form of triglycerides (the content of which can be 95% or more), the fatty acids at the Sn-2 position are mainly monounsaturated fatty acids (MUFAs) and polyunsaturated fatty acids (PUFAs), and are different from breast milk. The different structures of triglycerides affect digestion, absorption, and metabolism in infants and young children. The fatty acid type and position distribution of triglycerides determine the fatty acid absorption pattern, and the specificity of pancreatic lipase.

Currently, there have been some studies aimed at producing milk substitute fat or oil compositions that resemble milk components and fat structures as much as possible, such as:

citation 1 discloses a preparation method of a breast milk fatty structure ester substitute, which uses palm stearin as a raw material, improves the content of Sn-2-palmitic acid through random ester exchange reaction, and then uses Sn-1,3 specific lipase to catalyze palm stearin and mixed fatty acid which are subjected to random ester exchange reaction to prepare a structure ester similar to breast milk fat, namely the breast milk fatty structure ester substitute mainly comprising OPO.

Citation 2 indicates that there is a large difference in the content and ratio of OPL to OPO in chinese breast milk and other countries. In contrast, the proportion and the content of the OPO and OPL components in the grease composition are optimized according to the component characteristics of Chinese breast milk.

Citation 3 discloses a medium-long carbon chain triglyceride for breast milk-substituted lipids and a method for producing the same. The fish oil rich in OPL/OPO is used as a raw material, the MLCT is synthesized by lipase catalytic enzymatic transesterification, the MLCT and other oil are blended to obtain breast milk substitute fat, compared with breast milk fat, the similarity score of the constant MLCT and the trace MLCT is more than 80 minutes, and the problem of low similarity of the MLCT composition in the infant formula milk powder and the breast milk fat is solved.

Citation 4 discloses a breast milk-like fat composition, a preparation method and an application thereof, wherein in the fat composition, the content of OPO is 11.01-17.92%, the content of OPL is 11.10-20.45%, the content ratio of OPL/OPO is 0.92-1.71%, the content of MLCT is 19-38%, and the content of CN52 is 37.53-52% in percentage by weight.

It is seen that, although some prior arts have tried to prepare breast milk fat substitute fat with a similar composition to breast milk fat by various preparation methods, the research on the above is still insufficient, and the fat ratio has room for further improvement and further discussion.

Cited documents:

cited document 1: CN107751418A

Citation 2: CN112741163A

Cited document 3: CN112522330A

Cited document 4: CN114431306A

Disclosure of Invention

Problems to be solved by the invention

Currently, fat compositions that are similar in part to the composition of breast milk fat have been disclosed in the art. It should be noted, however, that although the main fat composition (including type and content) of breast milk can already be determined by existing instruments, it is still almost impossible to completely reproduce the fat composition of breast milk by means of manual reconstitution. Thus, when discussing the topic of "similarity" to breast milk fat, it is common to speak of, for example, some of the components in the fat composition being close to those in breast milk. The different levels of meanings are included, firstly, which fat components are selected to be close to the milk fat of the breast milk, secondly, how close the fat components are, and thirdly, the adjustment of which fat components can be conveniently and directly related to the effect of specific human body application.

In a specific study directed to the prior art, the inventors of the present application found that a part of the current research on the proximity to breast milk fat is focused on increasing the content of palmitic acid at the Sn-2 position. For example: citation 1 and citation 2 each focused on the optimization of the OPO component. Another part of the research has focused on bringing more fatty acid esters close to breast milk fat by means of a synthetic approach, for example, cited documents 3 and 4.

Furthermore, clinical feeding and experimental studies have shown that although infant formulas with unreasonable fatty acid compositions and fat sources of unreasonable structure provide energy, they can cause problems such as constipation, diarrhea, slow weight gain, etc. in infants, and also increase the incidence of infection.

Fatty acid mainly affects infants in two ways, namely, fatty acid components of cell membrane phospholipid are changed, so that the fluidity and integrity of the membrane are affected, and all organs of a body are disordered; secondly, the content of free fatty acid in the body is excessive, inflammation occurs, and the like, so that the health growth is not favorable.

The inventors of the present application believe that although the prior art described above makes the fatty acid ester composition more closely resemble breast milk fat by optimizing the content of palmitic acid in the Sn-2 position, or by optimizing a wider variety of triglycerides, it still does not achieve a complete approximation to the milk fat component of breast milk, and although in some cases the claimed approximation is improved, it is actually not a completely rational arrangement for absorption by the human body, especially for digestive absorption by infants. That is, although the current research emphasizes the close composition to that of breast milk fat, little attention is paid to how to improve the digestive absorption of the human body by properly arranging the composition of fatty acid esters.

Therefore, in view of the above-mentioned disadvantages of the prior art, the present invention is to provide a fatty acid ester composition having a reasonable fatty acid ratio and a fat composition close to that of breast milk, which has a significantly improved digestible effect on the human body, particularly on infants, and can provide sufficient nutrition to the maximum, and foods containing the same. That is, the present invention better balances the relationship between the proximity of the fatty acid ester composition to breast milk fat and the rationality of the fatty acid ester composition.

Means for solving the problems

Through long-term research by the inventor of the present invention, the following technical solutions can be found to solve the above technical problems:

[1] a fatty acid ester composition, wherein the fatty acid esters comprise OPL triglycerides, OPO triglycerides, OOL triglycerides, OLL triglycerides and LPLa triglycerides,

wherein the total amount of triglycerides in the composition,

the content of LPLa triglyceride is 0.5-2% by mass.

[2] The composition according to [1], wherein the content of OPL triglyceride is 15 to 22 mass% based on the total mass of triglyceride in the composition;

the content of OPO triglyceride is 12-18 wt%;

the content of OOL triglyceride is 7.5 to 10.5 mass%.

[3] The composition according to [1] or [2], wherein the content of LPLa triglyceride is 1 to 2 mass% based on the total mass of triglyceride in the composition.

[4] The composition according to [3], wherein the OLL triglyceride content is 5.5 mass% or more based on the total mass of triglycerides in the composition.

[5] The composition according to any one of [1] to [4], wherein the composition comprises vegetable oil, the vegetable oil comprises rapeseed oil and soybean oil, and optionally comprises one or more of sunflower seed oil, olive oil, sesame oil, corn oil, linseed oil and camellia seed oil.

[6] The composition according to [5], wherein the content of the vegetable oil is 13 to 35% by mass based on the total mass of the composition.

[7] The composition according to [5] or [6], wherein the rapeseed oil is contained in an amount of 1 to 10 mass% and the soybean oil is contained in an amount of 12 to 22 mass% based on the total mass of the composition.

[8] An digestible food product, wherein the food product comprises a composition according to any one of [1] to [7], optionally the composition is used in the form of an emulsion, a powder, an enhancer or a dietary supplement.

[9] The food according to [8], wherein the food comprises a liquid, solid or semi-solid type food such as a pasta, beverage, reconstitutable food, baked confectionery or functional nutritional supplement, and the beverage comprises a dairy type beverage.

[10] An infant milk product, wherein the milk product comprises the composition according to any one of [1] to [7].

ADVANTAGEOUS EFFECTS OF INVENTION

Through the implementation of the technical scheme, the invention has the following advantages and can obtain the following technical effects:

1) The invention considers the similarity of the fatty acid ester composition and the breast milk fat and also considers the reasonability of the configuration or the composition of the fatty acid ester aiming at the problem of digestion and absorption by human bodies;

2) The fatty acid ester composition provided by the invention is similar to breast milk fat in composition, and the grease with a specific structure and various vegetable oils play a role in a synergistic manner, so that a reasonable fatty acid ratio is achieved;

3) The fatty acid ester composition provided by the invention has the advantages that each component is in the safe dosage range, so that the fatty acid ester composition can be used for a long time and is suitable for various unspecified people;

4) The fatty acid ester composition provided by the invention can provide sufficient nutrition to the maximum extent, promote the growth of infants and meanwhile can be sufficiently digested and absorbed;

5) The fatty acid ester composition provided by the invention has clear components, is more beneficial to convenient and accurate compounding, and is also more beneficial to conveniently adding or preparing various foods, especially special diet, infant formula foods and the like.

Detailed Description

The present invention will be described in detail below. The technical features described below are explained based on typical embodiments and specific examples of the present invention, but the present invention is not limited to these embodiments and specific examples.

In the present specification, the meaning of "may" includes both the meaning of performing a certain process and the meaning of not performing a certain process.

As used herein, the term "optional" or "optional" is used to indicate that certain substances, components, performance steps, application conditions, and the like are used or not used.

In the present specification, the unit names used are all international standard unit names, and the "%" used means weight or mass% content, if not specifically stated.

In the present specification, reference to "some particular/preferred embodiments," "other particular/preferred embodiments," "embodiments," and the like, means that a particular element (e.g., feature, structure, property, and/or characteristic) described in connection with the embodiment is included in at least one embodiment described herein, and may or may not be present in other embodiments. In addition, it is to be understood that the described elements may be combined in any suitable manner in the various embodiments.

In the present specification, the numerical ranges indicated by "above" or "below" mean the numerical ranges including the numbers.

In the present specification, the numerical range represented by "a value a to B value" means a range including the endpoint value A, B.

In the present specification, the term "substantially" or "substantially" means that the standard deviation from the theoretical model or theoretical data is within 3%, preferably 2%, and more preferably 1%, and the deviation herein also includes systematic deviation.

As used herein, "room temperature" means an indoor ambient temperature of "20 ℃.

In this specification, the term "infant" is used to refer to a child aged 0 to 6 years.

In the present specification, "milk" is used to mean a liquid obtained from the mammary gland of a mammal during lactation. The term "milk" is to be interpreted broadly and covers both raw milk (i.e. liquid obtained directly from the mammary gland) and standardized milk products (like for example skim milk or whole milk), wherein the concentration of milk fat has been reduced relative to the original raw milk.

In the present specification, for convenience of expression with respect to fatty acid glycerides, the following characters are used to refer to different kinds of fatty acids:

ca: capric acid (C10: 0); la: lauric acid (C12: 0); m: myristic acid (C14: 0); p: palmitic acid (C16: 0); s: stearic acid (C18: 0); o: oleic acid (C18: 1); l: linoleic acid (C18: 2); ln: linolenic acid (C18: 3); ARA eicosatetraenoic acid (C20: 4); DHA is docosahexaenoic acid (C22: 6).

In the present specification, for a specific fatty acid ester, a side-by-side combination of the above characters is used to indicate the kind of fatty acid glyceride, wherein the letter or letter combination in the middle position indicates the fatty acid in the 2-position of glycerin. Specific examples thereof include:

OPO was used to denote 1,3-dioleoyl-2-palmitate; using OPL to represent: 1-oleic acid-2-palmitic acid-3-linoleic acid triglyceride.

In the present specification, the term "medium-chain fatty acid" as used for the chain length of fatty acid means fatty acid having a main chain length of 6 to 12 carbon atoms, and the term "medium-chain fatty acid" means fatty acid having a main chain length of more than 12 carbon atoms.

The Chinese terms corresponding to the following terms of the invention are as follows:

SFAs are saturated fatty acids; MUFAs: monounsaturated fatty acids; PUFAs: a polyunsaturated fatty acid; LCFAs: long chain fatty acids; MCFAs: medium chain fatty acids; and (3) MLCT: medium and long chain triglycerides.

The random transesterification referred to in the present specification means a reaction in which acyl groups are redistributed between or within triglyceride molecules of fats and oils, and finally a random distribution of fatty acids within the triglyceride mixture is achieved. The random transesterification reaction may be carried out in the presence of a chemical catalyst. Non-limiting examples of chemical catalysts include one or more of hydroxides, carbonates, bicarbonates, alkoxides of alkali or alkaline earth metals. The hydroxide of an alkali or alkaline earth metal may be selected from KOH, naOH, ca (OH) ₂ . The carbonate of an alkali metal may be selected from K ₂ CO ₃ 、Na ₂ CO ₃ . The alkali metal bicarbonate can be chosen from KHCO ₃ 、NaHCO ₃ . Alkali metal alkoxides such as sodium methoxide. The amount of the chemical catalyst to be added is not particularly limited, and may be, for example, 0.01 to 1% by weight, for example, 0.1% by weight, based on the total amount of the fats and oils added. The random transesterification reaction may also be carried out in the presence of a lipase.

In the present specification, the term "solution" is used to indicate a homogeneous system in which the solute is substantially or essentially dissolved under the conditions of the corresponding solvent, pH and concentration.

In the present specification, when a "main component" or a "main component" is referred to as a fatty acid ester, an oil or fat, a mixed structure ester, or the like, the content of the corresponding component is higher than the content of other components in the system.

The invention provides a fatty acid ester composition with optimized fatty acid triglyceride type, structure and content, and the optimization can lead the application of the fatty acid ester composition to obviously improve the human absorptivity relative to the prior breast milk-like milk fat, especially to the good absorbability for infants.

The technical scheme of the invention is mainly completed based on the following insights:

the content of palmitic acid in Sn-2 position is generally more concerned in the existing fatty acid ester composition of breast milk-like milk fat, which is mainly because the palmitic acid of fat in animal milk (such as cow milk) based raw materials is generally in 1 or 3 positions of glycerin, so that the content of the palmitic acid in Sn-2 position in the product fat can be increased by corresponding means, and the composition of the product fat can be closer to that of breast milk fat. In addition, by referring to a detection component table of breast milk fat components, fatty acid triglyceride obtained by various ester exchanges is mixed, so that the product oil and fat are closer to the breast milk fat in terms of components. Although attempts have been made to make the oil and fat composition of the product close to that of breast milk fat, since it is almost impossible to obtain an oil and fat product having the same composition as that of breast milk fat, and although 80% or more of the close-proximity oil and fat can be obtained as a whole, such oil and fat is not reasonable for human absorbability in actual use (even though no further studies have been made specifically for this purpose, it is generally considered that the effects of human use are close as long as the compositions are close to each other). Furthermore, on the basis of paying attention to the composition close to the milk fat of breast milk, the invention reasonably mixes the composition of the fatty glyceride in the fatty acid ester composition, so that the obtained oil product has the advantage of obviously improving the absorptivity of a human body in practical application.

< first aspect >

In a first aspect, the present invention provides a fatty acid ester composition comprising OPL triglyceride, OPO triglyceride, OOL triglyceride, OLL triglyceride and LPLa triglyceride, wherein the content of the triglyceride in the composition is adjusted to a reasonable range, thereby achieving the effect of improving the absorbability of the human body.

It has been surprisingly found that the fatty acid ester composition of the present invention, in which the LPLa triglyceride content is 0.5 to 2 mass%, preferably 1 to 2 mass%, more preferably 1.0 to 1.9 mass%, based on the total mass of triglycerides in the composition, can significantly improve the human absorbability of the fatty acid ester composition. Less than 0.5 mass% may also lead to improper disposition of other types of fatty acid esters, and more than 2 mass% may lead to deterioration of absorbability. The presence of LPLa triglycerides enriches the medium-and long-chain triglycerides of the fatty acid ester compositions of the present invention, which are capable of providing linoleic acid as an essential fatty acid, without causing fat accumulation on a rapid energy basis.

In some specific embodiments, the fatty acid ester composition of the present invention has an OPL triglyceride content of 15 to 22 mass%, preferably 16 to 21 mass%, more preferably 16.5 to 20 mass%, based on the total mass of triglycerides in the composition.

In some specific embodiments, the fatty acid ester composition of the present invention has an OPO triglyceride content of 12 to 18 mass%, preferably 14 to 18 mass%, more preferably 15 to 17.5 mass%, based on the total mass of triglycerides in the composition.

In some specific embodiments, the fatty acid ester composition of the present invention has an OOL triglyceride content of 7.5 to 10.5 mass%, preferably 8 to 10.5 mass%, more preferably 8.5 to 10.5 mass%, based on the total mass of triglycerides in the composition.

In some specific embodiments, the OLL triglyceride content in the fatty acid ester composition of the present invention is 5.5 mass% or more, preferably 6.5 mass% or more, more preferably 8.5 mass% or more, even more preferably 9 mass% or more, based on the total mass of triglycerides in the composition. The upper limit of the content of the OLL triglyceride is not particularly limited, and may be 15 mass%, preferably 12 mass%, and more preferably 10.5 mass% from the viewpoint of favorable absorption into the human body.

In addition, in some preferred embodiments of the present invention, the fatty acid ester composition of the present invention may further satisfy one or more of the following conditions from the viewpoint of further improving the absorbability to the human body:

the content of OPLa triglyceride is 3.5-5.3 mass%;

the total content of the LPCA triglyceride and the OPCa triglyceride is 1.2 to 2.5 mass%;

the total content of LPLn triglyceride and OPLn triglyceride is 1-2% by mass

M at the 2-position of the triglyceride accounts for more than 65% of the total M entering the triglyceride;

p at the 2-position of the triglyceride represents more than 78% of the total P entering the triglyceride;

ca and La at the 1 and 3 positions of triglycerides account for more than 70% of the total Ca and La entering the triglycerides;

o at the 1 and 3 positions of triglycerides represents more than 85% of the total O entering triglycerides;

l at the 1 and 3 positions of triglycerides represents more than 75% of the total L entering the triglycerides;

ln at the 1 and 3 positions of triglycerides represents more than 70% of the total Ln entering the triglycerides;

the La, M and P account for 4.0-5.8 mass%, 0.6-3.0 mass% and 17.8-22.5 mass% of the total composition respectively;

o, L, ln accounts for 30.1 to 39.9 mass%, 22.1 to 29.5 mass%, and 0.3 to 2.4 mass% of the total composition.

The components of the fatty acid ester composition of the present invention are closer to breast milk fat and at the same time can be fully digested and absorbed, while ensuring the respective triglyceride content in the fatty acid ester composition of the present invention. In this connection, the present invention does not specifically limit the sources of the various triglycerides.

In some embodiments, the triglycerides of the fatty acid ester compositions of the present invention can be derived from raw materials including, but not limited to, existing structured mixed esters, vegetable oils, and the like. For example, by mixing the OPL structure mixed ester, the OPO structure mixed ester, and the MLCT structure mixed ester having the limited compositions with vegetable oil, the content of triglyceride such as OPL, OPO, OOL, OLL, and LPLa can be adjusted finally, and the effect that the composition of the present invention can be sufficiently digested and absorbed by the human body while being close to the milk fat component of breast milk can be achieved.

(Structure Mixed ester)

The structural mixed ester includes OPO structural mixed ester, OPL structural mixed ester and MLCT structural mixed ester.

Since it is generally difficult to obtain a high-purity structural ester in a conventional manner (or to put it into practical industrial production because of its very poor economy), oil and fat products based on a structural ester of a certain structure are mainly mixed structural esters containing such structural esters.

The method for producing the mixed structure ester is not particularly limited in the present invention, and can be obtained by esterification of glycerin with fatty acid in the presence of a catalyst, or transesterification of conventional triglycerides derived from various sources with fatty acid in the presence of a (specific) catalyst (enzyme). And optionally, the products of the esterification reaction and the transesterification reaction can be post-treated by purification or the like to obtain the final structured mixed ester product.

Typical transesterification methods that may be exemplified are those in which a fully palmitoylated triglyceride (PPP) is used as a reaction raw material, and transesterification is carried out in the presence of a catalyst (e.g., a specific catalytic enzyme) to obtain a target mixed structure ester by adding other fatty acids such as oleic acid, linoleic acid, etc.

The mixed structure ester can be synthesized by the above method, or can be obtained directly from a commercially available product.

Mixed esters of MLCT structure

In the present invention, the "mixed ester with an MLCT structure" is a mixed ester with a structure containing a medium-long chain fatty acid triglyceride as a main component. "MLCT" refers to medium to Long carbon Chain Triglycerides (Middle to Long Chain Triglycerides) which are structural esters containing both medium Chain fatty acids, which refer to fatty acids containing 6 to 12 carbon atoms, and Long Chain fatty acids, which refer to fatty acids having greater than 12 carbon atoms, and Long Chain fatty acids on the glycerol backbone. The MLCT has the characteristics of medium-long chain fatty acid, and has the characteristics of supplementing essential fatty acid, quickly supplying energy and not causing fat accumulation.

The common MLCT in breast milk fat is mainly OPLa, LPLa, OPCa, OLaO, OLaL, OMLa, SLaL, and SLaO. The structure of the MLCT is similar to that of OPLa, namely the palmitic acid is positioned at the Sn-2 position, the oleic acid and the lauric acid are positioned at the Sn-1,3 position of the triglyceride, the absorption of the palmitic acid by infants can be enhanced, the loss of calcium in vivo can be reduced, and meanwhile, the medium-chain fatty acid positioned at the Sn-1,3 position can be rapidly digested and absorbed to provide energy for the infants. Thus, the term "mixed esters of MLCT structure" as used herein in reference to milk fat proximate to breast milk also includes one or more of the fatty acid triglycerides listed above.

In some embodiments of the invention, the content of OPLa triglyceride in the MLCT structure mixed ester is 20 to 25 mass%, more preferably 21 to 24 mass%.

In the MLCT-structured mixed ester, the content of OLaL triglyceride is preferably 15 to 20% by mass, and more preferably 16 to 18% by mass, from the viewpoint of facilitating absorption into the human body.

Further, in some other preferred embodiments, the MLCT structural mixed ester has a total ratio of Ca at 1-and 3-positions of more than 65%, preferably 70% or more, from the viewpoint of promoting absorption in human body. The total ratio herein also refers to the ratio of decanoic acid at positions 1 and 3 based on all decanoic acids bound to glycerol in the mixed ester of MLCT structure.

In the present invention, there is no particular limitation on the source of the mixed ester in the MLCT structure, and in some preferred embodiments, fish oil rich in OPL/OPO can be used as raw material, and MLCT with similar composition to breast milk fat can be synthesized by lipase-catalyzed enzymatic transesterification.

OPO structure mixed ester

In the present invention, the "OPO-structure mixed ester" is a structure mixed ester containing OPO triglyceride as a main component.

OPO triglyceride, i.e., 1,3-dioleic acid-2-palmitic acid triglyceride, is a structured fat. The molecular structure of breast milk lipid can be simulated by an enzymatic transesterification technology, so that the proportion of 2-position palmitic acid is close to the level of breast milk, and the 2-position palmitic acid is applied to infant formula food. The special two-position palmitic acid structure can be hydrolyzed into palmitic acid monoglyceride under the action of pancreatic lipase, can be combined with bile salt in vivo to form chylomicron which is easy to absorb by a human body, so that the absorption utilization rate of the fatty acid by the human body is improved, calcium soap is not easy to form during digestion, OPO accounts for the highest proportion in breast milk fat, and the palmitic acid monoglyceride can prevent constipation of infants, promote mineral absorption and provide sufficient energy for the infants.

In some specific embodiments of the present invention, the OPO structure mixed ester may include triglycerides of other structures such as OPL, OOL, OPP, OLO, OLL, and the like, in addition to OPO triglycerides. The type and amount of triglycerides for these other structures is mainly determined by the way the mixed ester of OPO structure is prepared.

In some specific embodiments, the content of OPO triglyceride in the OPO structure mixed ester of the present invention is 53% by mass or more, preferably 55% by mass or more, more preferably 58% by mass or more, and further preferably 60% by mass or more. The upper limit of the content of OPO triglyceride is not particularly limited, and may be 75 mass%, preferably 70 mass%, and more preferably 60 mass% from the viewpoint of economy or availability.

In some preferred embodiments, the OPO-structured mixed ester comprises, in addition to the aforementioned limited content of OPO triglyceride, 13 to 18 mass%, preferably 14 to 16 mass% of OPL; and/or, from 4 to 10 mass%, preferably from 5 to 8 mass%, of OOL.

In some other preferred embodiments of the invention, the percentage of P (palmitic acid) in the 2-position of the OPO structural mixed ester is greater than 65%, preferably greater than 70%, and more preferably greater than 75%, from the standpoint of close proximity to the milk fat composition of human milk. The ratio herein means the ratio of palmitic acid in the 2-position obtained based on all palmitic acid bonded to glycerin in the OPO structure mixed ester.

OPL structure mixed esters

In the present invention, the "OPL-structure mixed ester" is a structure mixed ester containing OPL triglyceride as a main component.

The OPL triglyceride, 1-oleic-2-palmitic-3-linoleic triglyceride, contains oleic acid and is also rich in linoleic acid. Linoleic acid is recognized as an essential fatty acid. Linoleic acid has been regarded as important for reducing blood cholesterol and preventing atherosclerosis. It has been found that cholesterol must be bound to linoleic acid before proper functioning and metabolism can occur in vivo. If the linoleic acid is lacked, cholesterol is combined with some saturated fatty acids, metabolic disorder occurs, the cholesterol is deposited on the blood vessel wall, atherosclerosis is gradually formed, and cardiovascular and cerebrovascular diseases are caused. In addition, linoleic acid has important effect on the development of infant brain and optic nerve, has obvious effect on improving infant intelligence and visual acuity, and simultaneously has the effects of reducing infant constipation and promoting the absorption of palmitic acid and mineral substances.

In some specific embodiments of the present invention, the OPL structure mixed ester may include triglycerides of other structures such as LPL, OPO, OOL, OPP, OLO, OLL, and the like, in addition to OPL triglycerides. The type and content of triglycerides for these other structures also depends mainly on the way the mixed esters of OPL structure are prepared.

In some specific embodiments, the content of OPL triglyceride in the OPL-structured mixed ester of the present invention is 40% by mass or more, preferably 45% by mass or more, more preferably 58% by mass or more, and still more preferably 60% by mass or more. The upper limit of the content of OPL triglyceride is not particularly limited, and may be 65 mass%, preferably 63 mass%, and more preferably 60 mass% from the viewpoint of economy or availability.

In some preferred embodiments, the OPL structured mixed ester comprises 5 to 15 mass%, preferably 8 to 12 mass% of LPL in addition to the above defined content of OPL triglyceride, the presence of an amount of LPL also contributing to an increased proportion of palmitic acid in the 2-position of the triglyceride.

In some other preferred embodiments of the invention, the proportion of P (palmitic acid) in the 2-position of the OPL structured mixed ester is greater than 80%, preferably greater than 85%, more preferably greater than 90%, from the standpoint of proximity to the composition of milk fat of breast milk. The ratio herein means the ratio of palmitic acid in the 2-position obtained based on all palmitic acid bonded to glycerin in the OPO structure mixed ester. In addition, optionally, the total ratio of L (linoleic acid) in the 1-and 3-positions in the OPL structure mixed ester is more than 80%, preferably more than 82%, more preferably more than 85%. The total ratio here also refers to the ratio of linoleic acid in the 1-and 3-positions obtained based on all linoleic acid bound to glycerol in the mixed ester of OPL structure.

(vegetable oil)

In some embodiments of the invention, the fatty acid ester compositions of the invention comprise vegetable oils. Wherein the vegetable oil comprises rapeseed oil and soybean oil, optionally comprises one or more of sunflower seed oil, olive oil, sesame oil, corn oil, linseed oil and camellia seed oil.

In some specific embodiments, the fatty acid ester composition of the present invention comprises 13% to 35%, preferably 15% to 33%, more preferably 20% to 33%, and even more preferably 23% to 33% of the vegetable oil, based on the total mass of the composition.

In some preferred embodiments, the rapeseed oil is present in an amount of 1 to 10 mass%, preferably 5 to 10 mass%, more preferably 7 to 10 mass%, based on the total mass of the fatty acid ester composition; the soybean oil content is 12 to 22% by mass, preferably 12 to 20% by mass, and more preferably 16 to 20% by mass. Further, optionally, the fatty acid ester composition of the present invention may further include sunflower oil in an amount of 5% by mass or less, preferably 1 to 4% by mass, more preferably 2 to 4% by mass, and olive oil in an amount of 2% by mass or less, preferably 0.5 to 2% by mass, more preferably 1 to 2% by mass.

By the configuration of the vegetable oil, the closeness degree of the fatty acid ester composition to breast milk can be further improved, and the configuration of various fatty acid triglycerides is more reasonable from the viewpoint of facilitating the absorption of a human body.

(fatty acid ester composition)

The fatty acid ester composition of the present invention comprises at least the above-described structural mixed ester and a vegetable oil. The form of the composition is not particularly limited, and the fatty acid composition of the present invention can be obtained by mixing in a mixing form that is usual in the art.

In some embodiments of the present invention, the content of the OPO-structured mixed ester in the fatty acid ester composition of the present invention is 18 to 30 mass%, more preferably 20 to 24 mass%, based on the total mass of the fatty acid ester composition, in consideration of the milk fat composition of human milk and the rational arrangement for easy absorption by human body, and in consideration of satisfying the content requirements of each triglyceride. The content of the OPL-structured mixed ester is 15 to 28% by mass, and more preferably 20 to 25% by mass. The content of the mixed ester having an MLCT structure is 14 to 24% by mass, and more preferably 14 to 20% by mass.

The other components that can be used in the composition of the present invention are not particularly limited, and other edible ingredients, food additives, solvent components, and the like that are generally used in the art may be used without impairing the effects of the present invention.

The fatty acid ester compositions of the present invention may be present in liquid form, or may be present in semi-solid or solid form.

Furthermore, experiments prove that the composition has excellent in-vitro digestion and hydrolysis efficiency, and the composition has the advantage of easy digestion. In addition, animal experiments show that the contents of fatty acid, calcium and magnesium in the excrement of rats which eat the composition show a remarkable reduction trend, which shows that the absorption efficiency of the fatty acid, the calcium and the magnesium is higher. Therefore, the product can be used as special diet and infant formula food.

< second aspect >

In a second aspect of the invention, there is provided a readily digestible human food product comprising or using a fatty acid ester composition as described in the first aspect of the invention. The form of the food is not particularly limited, and the fatty acid ester composition according to the present invention may be used in the form of emulsion, powder, fortifier or dietary supplement when preparing these foods.

With regard to the food products of the invention, in some preferred embodiments, it is a special dietary food product in liquid, semi-solid or solid form, particularly suitable for a specific (certain persons with impaired gastrointestinal function or infants). Examples thereof include: wheaten food, milk product, beverage, instant food, baked cake, functional nutritional supplement, instant food, etc.

The pasta may include a staple food produced or prepared from a flour-based raw material as a staple food, a minor cereal-based staple food, and the like, and specifically includes steamed bread-based, cake-based, noodle-based, and stuffing-based staple foods.

The beverage is not particularly limited, and may be a milky tea drink, milk, yogurt or other dairy beverage.

For reconstitutable foods, typically reconstitutable milk powder products may be used, such as children's milk powder, adult milk powder, middle aged and elderly milk powder, and the like.

For the baked confectionery, there may be baked cake or biscuit or the like based mainly on cream, egg and fermented powder.

In particular, the fatty acid ester composition provided by the invention is particularly suitable for being applied to infant milk products (formula milk powder), and has found that the reasonable configuration of the types and the proportion of the fatty acid esters can obtain better absorbability compared with the existing products.

These special dietary foods, which are not particularly limited, may be used as nutritional supplements or meal replacements, and such foods may include, in addition to the fatty acid ester composition of the present invention, one or more of the following components: protein, fat, essential carbohydrates, dietary fiber, supplemental elements, vitamins, plant or dietary components, and the like.

Wherein the protein is at least one selected from whey protein powder, soy protein isolate, whole milk powder, whole egg powder, lactoferrin, bovine colostrum, amino acid and protein peptide; the amino acid is at least one selected from L-lysine-L-glutamic acid, L-arginine, L-tryptophan, L-glutamine, taurine, L-valine, L-isoleucine and L-leucine; the protein peptide is selected from one or more of soybean oligopeptide, wheat protein peptide, silkworm pupa protein peptide, marine fish oligopeptide powder, cola peptide, amino peptide and egg albumin peptide.

The fat may include at least one of saturated fatty acid, polyunsaturated fatty acid, monounsaturated fatty acid, OPO structural ester, DHA, EPA, ARA, and phospholipid, and more specifically the fat includes safflower oil, walnut oil, peanut oil, soybean oil, argan, olive oil, tea oil, mayberry oil, olive oil, coconut oil, perilla oil, deep sea fish oil, cocoa butter, palm oil, beef tallow, butter, lard, medium chain triglycerides, and lecithin.

The carbohydrate includes starch or modified starch. The dietary fiber comprises one or more of inulin, konjac flour, galacto-oligosaccharide, fructo-oligosaccharide, isomalto-oligosaccharide, soybean polysaccharide, cyclodextrin, resistant dextrin and soybean fiber.

The supplementary elements are selected from metal ion salts of organic acids, such as one or more of calcium citrate, calcium lactate, calcium hydrogen phosphate, potassium gluconate, sodium citrate, ferrous gluconate, potassium iodide, zinc gluconate, sodium selenite, copper gluconate, chromium sulfate, manganese gluconate, and magnesium gluconate.

The vitamins are selected from one or more of vitamin A, beta-carotene, vitamin D3, vitamin E, vitamin K1, vitamin B2, vitamin B6, vitamin B12, vitamin C, pantothenic acid, folic acid, nicotinic acid, choline, inositol, and biotin.

The plant or dietary component comprises one or more of cereals, beans, potatoes, vegetables, bacteria and algae, nuts and seeds, fish and shrimp, livestock meat, and fruits.

Examples

Hereinafter, the present invention will be further specifically described by way of specific examples. The reagents, methods and apparatus employed in the present invention are those conventional in the art, unless otherwise specified.

< raw materials >

In the examples section that follows, the starting materials used are as follows, unless otherwise indicated.

Mixed ester of OPL structure (OPL 60%, LPL 10%, P at 2-position 89%, L at 3-position 88%);

mixed ester of OPO structure (OPO 55%, OPL 15%, OOL 5%, P at 2-position 84%);

MLCT structure mixed ester (OPLa of 22%, OLaL of 17%, ca of 91% in 3 position);

the sources of OPO and OPL are Yihaijiali grain and oil industry Co., ltd, and the source of MLCT is Bangjilode oil science Co., ltd.

Vegetable oils (rapeseed oil, soybean oil, sunflower seed oil, corn oil, olive oil, camellia seed oil, etc.) are commercially available.

The above raw materials were mixed according to the following examples and comparative examples to obtain respective fatty acid compositions.

Examples1：

Taking 28 parts of OPL structure mixed grease, 18 parts of OPO structure mixed grease, 14 parts of MLCT structure mixed grease, 8 parts of rapeseed oil, 20 parts of soybean oil, 3 parts of sunflower seed oil and 2 parts of olive oil by weight, and physically stirring and uniformly mixing. The composition is shown in Table 1.

Examples2：

Taking 27 parts of OPL structure mixed grease, 23 parts of OPO structure mixed grease, 17 parts of MLCT structure mixed grease, 10 parts of rapeseed oil, 13 parts of soybean oil, 5 parts of sunflower seed oil and 5 parts of corn oil by weight, and physically stirring and uniformly mixing. The composition is shown in Table 1.

Examples3：

Taking 24 parts of OPL structure mixed grease, 25 parts of OPO structure mixed grease, 17 parts of MLCT structure mixed grease, 8 parts of rapeseed oil, 16 parts of soybean oil, 4 parts of sunflower seed oil and 6 parts of camellia seed oil by weight, and physically stirring and uniformly mixing. The composition is shown in Table 1.

Comparative example1：

The mixed oil was obtained by mixing the above structured fat with vegetable oils (rapeseed oil, soybean oil, and sunflower oil), wherein the amount of rapeseed oil was 5 mass%, and the amount of soybean oil was 10 mass%. The composition is shown in Table 1.

Comparative example2：

By mixing the above structured fat and vegetable oils (rapeseed oil, soybean oil), a mixed fat was obtained, wherein the amount of rapeseed oil was 11 mass% and the amount of soybean oil was 19 mass%. The composition is shown in Table 1.

Control group:

is a commercially available common infant formula with high OPO content.

Sample a (example 1): concentrated whey protein powder and casein are used as protein sources, and the ratio of whey in breast milk is as follows: after the casein is 6:4, the fatty acid ester composition of example 1 (the addition amount is 27% of the formula energy supply ratio) and other ingredients are added, mixed uniformly, homogenized, sterilized, concentrated, and spray-dried to obtain sample a.

The main technological parameters are as follows: homogenizing at 20MPa; sterilizing (88-90 ℃ for 15 s); spray drying (the air inlet temperature is 160-180 ℃, and the air outlet temperature is 85-90 ℃).

Sample B (example 2): other raw materials and processes were consistent, and the source of the fatty acid ester composition was example 2.

Sample C (example 3): other raw materials and processes were consistent, and the source of the fatty acid ester composition was example 3.

Sample D (comparative example 1): other raw materials and processes were identical, and the source of the fatty acid ester composition was comparative example 1.

Sample E (comparative example 2): other raw materials and processes were identical, and the source of the fatty acid ester composition was comparative example 2.

Sample S1 (control): the other raw materials and processes were identical, and the source of the fatty acid ester composition was a control group.

Fat is extracted from commercial common infant formula milk powder (a control group) through pretreatment, and the content of triglyceride in the fat and the grease of the embodiment and the comparative example is detected by adopting ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS), and the result is shown in the following table 1.

TABLE 1

It can be seen that the OPO content in the above examples and comparative examples is close to that of commercial products, i.e., generally meeting the requirements of close human milk composition.

< in vitro simulation digestion hydrolysis Experimental example >

1. Materials and methods

1.1 Primary reagents

NaCl、HCl、KCl、CaCl ₂ NaOH, gastric lipase, pepsin, bile salts, and pancreatin were all from Sigma-Aldrich

1.2 Main instrumentation

Magnetic stirring (RH-A Basic magnetic stirrer manufactured by IKA corporation), and laser nanometer particle size analyzer (Nano-ZS 90 manufactured by Malvern corporation).

1.3 Experimental procedures

(1) Preparing gastric juice: 0.2g NaCl is weighed, 1.3mL HCl with concentration of 1mol/L is added, 80mL pure water is used for dissolving, 0.1mol/L HCl is added to adjust the pH value of the solution to 4.0, finally the pure water is added to 100mL, and the solution is marked as solution a. 5mg of gastric lipase and 0.5mg of pepsin are weighed and added into 5mL of solution a, and the mixture is magnetically stirred for 10min at room temperature to obtain simulated gastric fluid.

(2) Preparation of intestinal digestive juice: weighing 8.78g NaCl,0.37g KCl and 6.60g CaCl2, dissolving with pure water, adding 0.2mol/L NaOH to adjust the pH value of the solution to 6.5, and finally adopting pure water to fix the volume to 1L, wherein the solution is marked as solution b. Weighing 5mg of bile salt and 10mg of pancreatin, dissolving in 10mL of solution b, and magnetically stirring at 37 ℃ for 10min to obtain the simulated small intestine digestive juice.

(3) And (3) simulating digestion: weighing 1.35g of the prepared infant formula milk powder, adding 9mL of pure water, uniformly stirring to dissolve the infant formula milk powder without lumps, and then preserving the infant formula milk powder in a water bath at 37 ℃ for 10min; adjusting the pH value to 6.0, adding 2.5mL of simulated gastric juice, stirring and digesting at 37 ℃ for 0.5h, adjusting the pH value of digestive juice digested by the simulated gastric juice to 6.5 by using 0.2mol/L NaOH, adding 10mL of simulated intestinal juice, simulating digestion of small intestine for 2h, continuously dropwise adding 0.1mol/L NaOH solution in the simulated digestion process to keep the pH value of the system at 6.5, recording the amount of NaOH consumed at different times, and keeping the temperature at 37 ℃ in the whole process.

1.4 statistical analysis and calculation

Each sample was subjected to at least 3 simulated digestion tests, the release rate of free fatty acid during digestion and the change in particle size before and after digestion were determined, and the average value was taken.

Release rate of free fatty acids (%) = 100V C M/2M, where C is concentration of NaOH solution (0.1 mol/L), V is amount of NaOH solution consumed over time (mL), M is molar mass of fatty acid ester composition (g/mol), M is mass of added fatty acid ester composition (g);

the particle size is measured by a laser nanometer particle size analyzer at 25 ℃.

The experimental data are expressed in mean ± standard deviation (mean ± SD), each experiment is repeated at least three times independently, graph is drawn by GraphPad Prism 8.00, excel 2018 and R language, statistical analysis is performed on the experimental data by using SPSS 16.0 software, and single factor analysis of variance (Duncan's) is applied. P <0.05 represents significant difference.

1.5 results of the experiment

To evaluate the digestive absorption of infant formula with the addition of fatty acid ester compositions of different structures, the release rate of free fatty acids was determined for different digestion times, as shown in tables 2 and 3.

TABLE 2

TABLE 3

In the table above, compared with the control group and the comparative example, the examples have higher release rate of free fatty acid in stomach at different digestion time, which shows that the fatty acid ester composition of the examples of the present invention has reasonable proportion and is easier to digest and absorb.

The particle size of the free fatty acids was also determined for different digestion times as shown in table 4.

TABLE 4

In the above table, the particle size of the free fatty acid of each example is smaller at different digestion times in the small intestine than the control group and the comparative example, which shows that the fatty acid ester composition of the example of the present invention has a reasonable formulation and can be sufficiently digested and absorbed in the human body.

< animal experiments >

1. Materials and methods

1.1 Experimental materials

SD rats (animal breeding center of military medical science institute), male, body weight 300.0g + -5.0 g; .

1.2 Experimental procedures

(1) The rats were randomly divided into 5 groups of 10 rats each. The control group used common vegetable mixed oil (sunflower seed oil, coconut oil, linseed oil, rapeseed oil), the test group used the composition example and the comparative example, the oil feeding was fixed at 10 am (the oil sample was bathed to 37 ℃ before the test), the frequency was once in two days, and the feeding amount and time were 20% of the daily average energy intake and 6 weeks, respectively. During the experiment rats were fed normal diet and water, and the feed intake and body weight of the rats were recorded.

(2) Collecting rat feces for three consecutive days after feeding for 6 weeks, placing the rat feces in liquid nitrogen for preservation after a centrifugal tube, and carrying out fatty acid detection in a follow-up test. And (3) carrying out lipid extraction on the fecal sample according to requirements, carrying out fatty acid methyl esterification, and analyzing by adopting a gas phase method. And (3) measuring the content of calcium and magnesium ions in the excrement by adopting a mass spectrometry method.

In order to evaluate the absorption of fatty acids, calcium and magnesium during actual digestion, the contents of fatty acids, calcium and magnesium in rat feces fed with fatty acid ester compositions of different structures were measured, as shown in table 5.

TABLE 5

In the above table, the contents of fatty acid, calcium and magnesium in the feces of the rats fed with the fatty acid ester composition of the example are lower than those of the control group and the comparative example, which indicates that the fatty acid ester composition of the example of the present invention has a reasonable formulation and is more easily digested and absorbed.

Industrial applicability

The fatty acid ester composition of the present invention can be industrially produced and can be applied to foods.

Claims

1. A fatty acid ester composition, wherein said fatty acid esters comprise OPL triglyceride, OPO triglyceride, OOL triglyceride, OLL triglyceride and LPLa triglyceride,

wherein the total amount of triglycerides in the composition,

the content of LPLa triglyceride is 0.5-2% by mass.

2. The composition according to claim 1, wherein the triglyceride is present in the composition in a molar ratio based on the total mass of the triglyceride in the composition,

the content of OPL triglyceride is 15-22 wt%;

the content of OPO triglyceride is 12-18 wt%;

the content of OOL triglyceride is 7.5 to 10.5 mass%.

3. The composition according to claim 1 or 2, wherein the content of LPLa triglyceride is 1 to 2 mass% based on the total mass of triglyceride in the composition.

4. The composition of claim 3, wherein the OLL triglyceride content is 5.5 mass% or more based on the total mass of triglycerides in the composition.

5. The composition according to any one of claims 1 to 4, wherein the composition comprises vegetable oil, wherein the vegetable oil comprises rapeseed oil and soybean oil, optionally comprising one or more of sunflower oil, olive oil, sesame oil, corn oil, linseed oil, camellia oil.

6. The composition according to claim 5, wherein the vegetable oil is contained in an amount of 13 to 35 mass% based on the total mass of the composition.

7. The composition according to claim 5 or 6, wherein the rapeseed oil is present in an amount of 1 to 10 mass% and the soybean oil is present in an amount of 12 to 22 mass%, based on the total mass of the composition.

8. A digestible food product, wherein the food product comprises a composition according to any of claims 1 to 7, optionally wherein the composition is used in the form of an emulsion, a powder, an enhancer or a dietary supplement.

9. The food product according to claim 8, wherein the food product comprises a liquid, solid or semi-solid type food product, preferably the food product is a reconstitutable food product.

10. An infant milk product, characterized in that it comprises a composition according to any one of claims 1 to 7.