WO2020248710A1 - 一种油脂组合物及其制备方法 - Google Patents

一种油脂组合物及其制备方法 Download PDF

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WO2020248710A1
WO2020248710A1 PCT/CN2020/085237 CN2020085237W WO2020248710A1 WO 2020248710 A1 WO2020248710 A1 WO 2020248710A1 CN 2020085237 W CN2020085237 W CN 2020085237W WO 2020248710 A1 WO2020248710 A1 WO 2020248710A1
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acid
fatty acids
composition according
grease composition
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French (fr)
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王卫飞
廖森泰
邹宇晓
穆利霞
王思远
胡腾根
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广东省农业科学院蚕业与农产品加工研究所
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Publication of WO2020248710A1 publication Critical patent/WO2020248710A1/zh

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/232—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having three or more double bonds, e.g. etretinate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the invention relates to a fat composition, in particular to a fat composition rich in unsaturated fatty acids and medium and short-chain fatty acids.
  • Polyunsaturated fatty acids generally refer to fatty acids containing two or more double bonds.
  • PUFA Polyunsaturated fatty acids
  • a large number of studies have confirmed that polyunsaturated fatty acids are essential nutrients for the growth and development of human and animal bodies, and for maintaining normal metabolism and physiological activities.
  • intake of sufficient polyunsaturated fatty acids can also adjust and improve lipid metabolism in humans and animals, especially the functions of n-3 polyunsaturated fatty acids in lowering blood lipids and assisting in lowering blood sugar.
  • Some n-6 and n -9 Polyunsaturated fatty acids have weight loss function.
  • Common PUFAs with special physiological functions for the human body are mainly eicosapentaenoic acid (EPA, n-3), docosahexaenoic acid (DHA, n-3), eicosapentaenoic acid (DPA, n-3) -6), arachidonic acid (AA, n-6), stearidonic acid (SDA, n-3), ⁇ -linolenic acid (ALA, n-3), ⁇ -linolenic acid (GLA, n-3) -6), conjugated linolenic acid (CLNA, n-6), conjugated linoleic acid (CLA, n-9), etc.
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • DPA eicosapentaenoic acid
  • SDA stearidonic acid
  • ⁇ -linolenic acid ALA, n-3
  • Polyunsaturated fatty acids are mostly derived from plants, microorganisms or aquatic plankton. It is difficult for humans and animals to synthesize polyunsaturated fatty acids efficiently.
  • the polyunsaturated fatty acids needed to maintain normal physiological activities need to be ingested from food. Therefore, people generally extract and process oils rich in polyunsaturated fatty acids from natural animal and plant sources into functional foods or dietary supplements.
  • Such processed products generally take the form of natural polyunsaturated fatty acid glycerides, phospholipids or processed fatty acids and fatty acid ethyl esters.
  • low-purity (lower polyunsaturated fatty acid content) triglycerides and high-purity (lower polyunsaturated fatty acid content) fatty acid ethyl esters are the main product forms. . PUFAs in these product forms generally suffer from low absorption efficiency and low bioavailability when consumed.
  • fatty acid ethyl esters are not the natural form of human and higher animal intake of fats and oils, the digestion and absorption rate of fatty acid ethyl esters by digestive system enzymes is not high, and the absorption rate of PUFA in ethyl ester products is low.
  • people have done some research on improving the absorption and utilization of PUFA in products.
  • the absorption of PUFA can be improved by adding digestion and absorption aids and rationally designed molecular structures in the product.
  • Svein Olaf Hustvedt and others used the method of adding emulsifiers and antioxidants to increase the absorption rate of EPA and DHA in ethyl ester products to more than 4 times [A Novel Self-Micro-Emulsifying Delivery System Enhances Enrichment of Eicosapentaenoic Acid and Docosahexaenoic Acid after Single and Repeated Dosing in Healthy Adults in a Randomized Trial]. Research by Cui Jie et al.
  • n-3 long-chain PUFA in the form of glyceride (TG) is faster than that in the form of phospholipid (PL), but the PL form can maintain a high concentration of EPA and DHA in the blood for a long time:
  • TG glyceride
  • PL phospholipid
  • liposomes can significantly increase the content of serum n-3 long-chain PUFA and maintain a higher level for a long time [different molecular forms The digestion and absorption characteristics of n-3 series of long-chain polyunsaturated fatty acids and their influence on lipid metabolism]. Since the product is not the best molecular structure for the digestion and absorption of its active ingredients (PUFA) and its physiological functions, the efficiency of digestion and absorption is improved by adding emulsifiers or liposomes.
  • PUFA active ingredients
  • the physiological functions of PUFAs ingested through diet need to be digested and absorbed to be effective. Aiming at the problems of low PUFA digestion and absorption rate and low physiological availability in existing PUFA products, the present invention provides a higher digestion and absorption rate and Bioavailable grease composition.
  • a grease composition the general formula of the composition is:
  • the fatty acid acyl groups R1 and R3 at the sn-1(3) position of the triglyceride are polyunsaturated fatty acids with a carbon chain length of 18-22 carbon atoms, and the fatty acid acyl group R2 at the sn-2 position is a medium and short-chain fatty acid.
  • R2 is one or a mixture of two or more of acetic acid, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, and myristic acid.
  • R2 is one or a mixture of two or more of butyric acid, caprylic acid and lauric acid.
  • R1 and R3 are eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), eicosapentaenoic acid (DPA), arachidonic acid (AA), octadecane
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • DPA eicosapentaenoic acid
  • AA arachidonic acid
  • AA arachidonic acid
  • SDA enoic acid
  • ALA ⁇ -linolenic acid
  • GLA ⁇ -linolenic acid
  • CLNA conjugated linolenic acid
  • CLA conjugated linoleic acid
  • the mass ratio of n-3 PUFA in R1 and R3 is not less than 50%.
  • the mass ratio of n-3 PUFA in R1 and R3 is not less than 60%.
  • the mass ratio of butyric acid in R2 is not less than 30%; in R1 and R3, the mass ratio of EPA is not less than 15%.
  • the mass ratio of butyric acid in R2 is not less than 50%; in R1 and R3, the mass ratio of EPA is not less than 30%.
  • two or more polyunsaturated fatty acids are mixed with short- and medium-chain fatty acid glycerides in a molar ratio of 2.5:1, and 5% by mass of the immobilized fatty acid Lipozyme 40086 is added and placed at a constant temperature of 50-60°C.
  • the absolute pressure is below 200Pa
  • the reaction time is 8h-24h
  • the oil phase of the reactant is recovered and purified by molecular distillation to remove free fatty acids and other low-boiling components to obtain polyunsaturated fatty acids and short-chain fatty acids Grease composition.
  • the molecular distillation temperature is 180-190°C, and the working absolute pressure of the molecular still is below 1 Pa.
  • the polyunsaturated fatty acid may be a single component or a mixture of multiple PUFAs.
  • the molecular structure and fatty acid composition and position arrangement of the structural lipids rich in polyunsaturated fatty acids are designed, that is, the polyunsaturated fatty acids are bound to the sn-1(3) position of the glyceride, and the short and medium chain fatty acids are bound to The sn-2 position of glycerides and short- and medium-chain fatty acids have a synergistic effect on the ingestion and physiological function of PUFA, which improves the absorption and bioavailability of PUFA.
  • the structured fat rich in polyunsaturated fatty acids of the present invention is mainly triglyceride, which is a kind of fat with a special structure that is different from the existing commercially available polyunsaturated fatty acid ethyl ester or glyceride type products Acid ester.
  • the structural lipid of the polyunsaturated fatty acid in the present invention has better oxidation stability and soft smell, and can be used as a dietary supplement without changing people's dietary composition and eating habits. And has a more effective effect of lowering blood fat and losing weight.
  • the examples further illustrate the present invention. These examples are only used to illustrate the present invention and do not limit the scope of the present invention.
  • the present invention refers to "Study on Immobilized Lipase Talaromyces thermophilus Lipase (TTL) for Preparation of LML-type Structural Lipids" to prepare structural lipids with sn-1, 3 positions as PUFA, and sn-2 positions as medium and short-chain fatty acids.
  • the absolute pressure is below 200Pa, and the reaction time is 8h.
  • the oil phase of the reactant is recovered and purified by molecular distillation.
  • the molecular distillation temperature is 180-190°C, and the absolute pressure of the molecular distiller is below 1Pa.
  • Free fatty acids and other low boiling point components are removed to obtain polyunsaturated fatty acids and medium and short Fatty composition of chain fatty acid.
  • the total fatty acid composition of glycerides is shown in Table 1, and the product is recorded as composition 1.
  • the mixed fatty acid and tributyrin are mixed according to the molar ratio of 2.5:1, and 5% of the mass of the mixture is added to the immobilized lipase Lipozyme RM (product of Novozymes), and they are placed in a constant temperature stirred reactor at 50-60°C.
  • the absolute pressure of the reactor is below 200Pa, and the reaction time is 8h.
  • the oil phase of the reactant is recovered and purified by molecular distillation.
  • the molecular distillation temperature is 180-190°C, and the absolute pressure of the molecular distiller is below 1Pa. Free fatty acids and other low boiling point components are removed to obtain polyunsaturated fatty acids and medium and short Fatty composition of chain fatty acid.
  • the total fatty acid composition of glycerides is shown in Table 1, and the product is recorded as composition 2.
  • the mixed fatty acid and trihexanoic acid are mixed according to the molar ratio of 2.5:1, and the immobilized lipase Lipozyme RM (product of Novozymes) with 5% of the mass of the mixture is added, and they are placed in a constant temperature stirred reactor at 50-60°C.
  • the absolute pressure of the reactor is below 100Pa, and the reaction time is 12h.
  • the oil phase of the reactant is recovered and purified by molecular distillation.
  • the molecular distillation temperature is 180-190°C, and the absolute pressure of the molecular distiller is below 1Pa. Free fatty acids and other low boiling point components are removed to obtain polyunsaturated fatty acids and medium and short Fatty composition of chain fatty acid.
  • the total fatty acid composition of glycerides is shown in Table 1, and the product is recorded as composition 3.
  • the mixed fatty acid and tricaprylin are mixed according to the molar ratio of 2.5:1, and the immobilized lipase Lipozyme RM (product of Novozymes) with 5% of the mass of the mixture is added, and they are placed in a constant temperature stirred reactor at 50-60°C.
  • the absolute pressure is below 200Pa, and the reaction time is 24h.
  • the oil phase of the reactant is recovered and purified by molecular distillation.
  • the molecular distillation temperature is 190-200°C, and the absolute pressure of the molecular distiller is below 0.1Pa.
  • Free fatty acids and other low-boiling components are removed to obtain polyunsaturated fatty acids and medium. Oil and fat composition of short-chain fatty acids.
  • the total fatty acid composition of glycerides is shown in Table 1, and the product is recorded as composition 4.
  • the mixed fatty acid and glyceryl trilaurate were mixed in a molar ratio of 3.5:1, and 5% of the mass of the mixture was added to the immobilized lipase LipozymeRM (product of Novozymes), and they were placed in a constant temperature stirred reactor at 50-60°C.
  • the absolute pressure of the device is below 100Pa, and the reaction time is 24h. After the oil phase of the reactant is recovered, it is separated and purified by molecular distillation.
  • the molecular distillation temperature is 200-205°C, and the absolute pressure of the molecular distiller is below 0.01 Pa.
  • the fatty acid ethyl ester and other low-boiling components are removed to obtain polyunsaturated fatty acids and Grease composition of medium and short chain fatty acids.
  • the total fatty acid composition of glycerides is shown in Table 1, and the product is recorded as composition 5.
  • the mixed fatty acid and the glyceride are mixed according to the molar ratio of 3.5:1, and the immobilized lipase Novozyme 435 (product of Novozymes) with 5% of the mass of the mixture is added and placed in a constant temperature stirred reactor at 50-60°C.
  • the pressure is below 200Pa, and the reaction time is 8h.
  • the molecular distillation temperature is 180-190°C, and the absolute pressure of the molecular distiller is below 1Pa. Free fatty acids and other low boiling point components are removed to obtain polyunsaturated fatty acid glycerides.
  • the total fatty acid composition of glycerides is shown in Table 1, and this product is recorded as Comparative Composition 1.
  • Fatty acid composition analysis of oil and fat composition is based on "GB 5009.168-2016 National Food Safety Standard Determination of Fatty Acids in Foods", using the method "GB/T 21121-2007 Determination of Oxidation Stability of Animal and Vegetable Oils (Accelerated Oxidation Test)” at 90 degrees , Evaluate its oxidation stability, and obtain the OSI value; the results are shown in Table 1.
  • composition 1-5 and comparative composition 1-3 as the evaluation objects, the oil bioavailability inspection method published in the document "Preparation and Bioavailability and Safety Evaluation of 1,3-Diglyceride Microemulsion" was evaluated.
  • PUFA bioavailability of the composition The experimental animals were SD rats, which were purchased from SCXK (Guangdong) 2013-0034, Laboratory Animal Center of Southern Medical University. Maintenance feed, purchased from Guangdong Medical Laboratory Animal Center, license number: SCXK (Guangdong) 2013-0002.
  • the rats were fed with fat-free diets, and after one week of adaptation, they were randomly divided into 8 groups, each with 9 rats, including 4 female rats and 5 male rats. All animals eat and drink freely.
  • the PUFA glyceride composition was intragastrically administered at an added amount of 1.6 mg/g. After gavage for 2 hours, three rats were taken from each group for tail vein blood collection. The blood was collected and centrifuged, and the upper serum was taken and stored at -20°C for testing. The feces of each rat were collected on the last day of the experiment.
  • the PUFA glyceride composition experimental group provided by the present invention has significantly higher levels of polyunsaturated fatty acids in serum and digestion and absorption rate than the comparison composition group. This indicates that the PUFA in the PUFA glyceride composition provided by the present invention has a higher absorption rate and bioavailability.
  • the PUFA glyceride composition provided by the present invention has a more effective function of lowering blood fat and weight loss, and the PUFA in it has a higher absorption rate and bioavailability. .

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Abstract

一种油脂组合物及其制备方法，该组合物通式为Ⅰ，其中，甘油三酯的sn-1(3)位的脂肪酸酰基R1、R3为碳链长度为18～22个碳原子的多不饱和脂肪酸，sn-2位的脂肪酸酰基R2为中短链脂肪酸。该组合物提高了PUFA的吸收率和生物利用度。(I)

Description

一种油脂组合物及其制备方法 技术领域
本发明涉及一种油脂组合物，尤其是一种涉及富含不饱和脂肪酸和中短链脂肪酸的油脂组合物。
背景技术
多不饱和脂肪酸(PUFA)一般是指含有两个或两个以上双键的脂肪酸。大量的研究证实，多不饱和脂肪酸是人和动物体生长发育及维持正常新陈代谢和生理活动必需的营养元素。而且膳食中，摄入足量的多不饱和脂肪酸还可以调节改善人和动物体内脂质代谢，特别是n-3类多不饱和脂肪酸降血脂、辅助降血糖的功能，部分n-6和n-9多不饱和脂肪酸具有减肥功能。对人体具有特殊生理功能的常见PUFA主要有二十碳五烯酸(EPA,n-3)、二十二碳六烯酸(DHA,n-3)、二十碳五烯酸(DPA,n-6)、花生四烯酸(AA,n-6)、十八碳四烯酸(SDA,n-3)、α-亚麻酸(ALA,n-3)、γ-亚麻酸(GLA,n-6)、共轭亚麻酸(CLNA,n-6)、共轭亚油酸(CLA,n-9)等。
多不饱和脂肪酸多来源于植物、微生物或水生浮游生物，人和动物体内难以高效合成多不饱和脂肪酸，维持正常生理活动所需的多不饱和脂肪酸需要从食物中摄取。因此，人们一般将天然动植物来源的富含多不饱和脂肪酸的油脂提取加工后成为功能食品或膳食补充剂。这一类的加工产品，一般以多不饱和脂肪酸天然形态的甘油酯、磷脂或加工后的脂肪酸、脂肪酸乙酯的形式为主。其中，目前的富含多不饱和脂肪酸的产品中，以低纯度(多不饱和脂肪酸含量较低)的甘油 三酯和高纯度(多不饱和脂肪酸含量较低)的脂肪酸乙酯为主要产品形式。这些产品形式的PUFA在食用时普遍存在着吸收效率不高，生物利用度低的问题。
由于脂肪酸乙酯不是人和高等动物摄入油脂的天然形式，消化系统的酶系对脂肪酸乙酯的消化吸收率不高，乙酯型的产品中的PUFA吸收率较低。目前人们对提高产品中PUFA吸收率和利用度进行了部分研究，通过在产品中添加消化吸收助剂和设计合理的分子结构均可以提高PUFA的吸收率。Svein Olaf Hustvedt等采用添加乳化剂和抗氧化剂的方式，将乙酯型产品中的EPA和DHA的吸收率提高至4倍以上[A Novel Self-Micro-Emulsifying Delivery System Enhances Enrichment of Eicosapentaenoic Acid and Docosahexaenoic Acid after Single and Repeated Dosing in Healthy Adults in a Randomized Trial]。崔洁等研究发现甘油酯(TG)形式的n-3长链PUFA的消化吸收速度快于磷脂(PL)形式，但PL形式却可以使血液中EPA和DHA长时间维持在较高的浓度：脂质体和乳剂形式磷脂的消化吸收特性同样存在差异；相比于乳剂形式，脂质体可以更显著地增加血清n-3长链PUFA的含量且长时间保持在较高水平[不同分子形式n-3系列长链多不饱和脂肪酸的消化吸收特性及其对脂质代谢的影响]。产品由于不是其有效成分(PUFA)消化吸收和发挥生理功能的最佳分子结构形式，因此才通过添加乳化剂或脂质体的形式提高其消化吸收效率。
发明内容
经膳食摄取的PUFA，其生理功能需经过消化吸收才能有效发挥，针对现有PUFA产品中的PUFA消化吸收率低、生理利用度不高等问题，本发明提供一种具有更高的消化吸收率和生物利用度的油脂组合物。
本发明的目的通过以下技术方案实现：
一种油脂组合物，该组合物通式为：
Figure PCTCN2020085237-appb-000001
其中，甘油三酯的sn-1(3)位的脂肪酸酰基R1、R3为碳链长度为18～22个碳原子的多不饱和脂肪酸，sn-2位的脂肪酸酰基R2为中短链脂肪酸。
优选地，R2为乙酸、丁酸、己酸、辛酸、癸酸、月桂酸、豆蔻酸中的一种或两种以上的混合。
优选地，R2为丁酸、辛酸、月桂酸中的一种或两种以上的混合。
优选地，R1、R3为二十碳五烯酸(EPA)、二十二碳六烯酸(DHA)、二十碳五烯酸(DPA)、花生四烯酸(AA)、十八碳四烯酸(SDA)、α-亚麻酸(ALA)、γ-亚麻酸(GLA)、共轭亚麻酸(CLNA)、共轭亚油酸(CLA)中的一种或两种以上的混合。
优选地，R1和R3中，n-3PUFA的质量比例不低于50％。
优选地，R1和R3中，n-3PUFA的质量比例不低于60％。
优选地，R2中丁酸的质量比例不低于30％；R1和R3中，EPA的质量比例不低于15％。
优选地，R2中丁酸的质量比例不低于50％；R1和R3中，EPA的质量比例不低于30％。
上述油脂组合物的制备方法，将两种以上多不饱和脂肪酸与中短链脂肪酸甘油酯按照摩尔比2.5:1混合，加入混合物质量5％的固定化脂肪酸Lipozyme 40086，置于50-60℃恒温搅拌反应，绝对压力为200Pa以下，反应时间为8h～24h；反 应物油相回收后经分子蒸馏分离纯化，除去游离脂肪酸及其他低沸点组分，得到含有多不饱和脂肪酸及中短链脂肪酸的油脂组合物。
优选地，所述分子蒸馏温度为180-190℃，分子蒸馏器工作绝对压力为1Pa以下。
本研究发现，天然油脂原料中的PUFA一般与其他脂肪酸混合存在，特别是碳链长度为18～22个碳原子的饱和脂肪酸及单不饱和脂肪酸，这在一定程度上影响了PUFA的吸收率和生物利用度。
在本发明的油脂组合物中，多不饱和脂肪酸可以是单一成分，也可以是多种PUFA的混合。本发明通过对富含多不饱和脂肪酸结构脂的分子结构和脂肪酸组成及位置排布进行定向设计，即多不饱和脂肪酸结合在甘油酯的sn-1(3)位，中短链脂肪酸结合在甘油酯的sn-2位，以及中短链脂肪酸对PUFA在摄入和发挥生理功能中的协同作用，提高了PUFA的吸收率和生物利用度。本发明的富含多不饱和脂肪酸的结构脂，以甘油三酯为主，是一种与现有市售的多不饱和脂肪酸乙酯或甘油酯型的产品所不同的一种特殊结构的脂肪酸酯。本发明中多不饱和脂肪酸的结构脂氧化稳定性更好，气味柔和，可以作为一种膳食补充剂，不改变人们的膳食组成和饮食习惯。且具有更高效的降血脂、减肥功效。
具体实施方式
实施例对本发明做进一步说明，这些实施例仅用来说明本发明，并不限制本发明的范围。本发明参考《固定化脂肪酶Talaromycesthermophilus lipase(TTL)制备LML型结构脂的研究》制备sn-1,3位为PUFA，sn-2位为中短链脂肪酸的结构脂。
实施例1
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA多不饱和脂肪酸为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA20.25％、AA8.53％、SDA2.71％、ALA6.23％、GLA3.61％、CNLA 6.67％及CLA 9.46％，其他脂肪酸9.24％)。混合脂肪酸与三乙酸甘油酯按照摩尔比2.5:1混合，加入混合物质量5％的固定化脂肪酶LipozymeRM(诺维信公司产品)，一起置于50-60℃的恒温搅拌反应器中，反应器绝对压力为200Pa以下，反应时间为8h。反应物油相回收后经分子蒸馏分离纯化，分子蒸馏温度为180-190℃，分子蒸馏器工作绝对压力为1Pa以下，除去游离脂肪酸及其他低沸点组分，得到含有多不饱和脂肪酸及中短链脂肪酸的油脂组合物。甘油酯总脂肪酸组成见表1，该产品记为组合物1。
实施例2
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA多不饱和脂肪酸为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA 20.25％、AA 8.53％、SDA 2.71％、ALA 6.23％、GLA3.61％、CNLA 6.67％及CLA 9.46％，其他脂肪酸9.24％)。混合脂肪酸与三丁酸甘油酯按照摩尔比2.5:1混合，加入混合物质量5％的固定化脂肪酶LipozymeRM(诺维信公司产品)，一起置于50-60℃的恒温搅拌反应器中，反应器绝对压力为200Pa以下，反应时间为8h。反应物油相回收后经分子蒸馏分离纯化，分子蒸馏温度为180-190℃，分子蒸馏器工作绝对压力为1Pa以下，除去游离脂肪酸及其他低沸点组分，得到含有多不饱和脂肪酸及中短链脂肪酸的油脂组合物。甘油酯总脂肪酸组成见表1，该产品记为组合物2。
实施例3
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA多不饱和脂肪酸为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA 20.25％、AA 8.53％、SDA 2.71％、ALA 6.23％、GLA3.61％、CNLA 6.67％及CLA 9.46％，其他脂肪酸9.24％)。混合脂肪酸与三己酸甘油酯按照摩尔比2.5:1混合，加入混合物质量5％的固定化脂肪酶LipozymeRM(诺维信公司产品)，一起置于50-60℃的恒温搅拌反应器中，反应器绝对压力为100Pa以下，反应时间为12h。反应物油相回收后经分子蒸馏分离纯化，分子蒸馏温度为180-190℃，分子蒸馏器工作绝对压力为1Pa以下，除去游离脂肪酸及其他低沸点组分，得到含有多不饱和脂肪酸及中短链脂肪酸的油脂组合物。甘油酯总脂肪酸组成见表1，该产品记为组合物3。
实施例4
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA多不饱和脂肪酸为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA 20.25％、AA 8.53％、SDA 2.71％、ALA 6.23％、GLA3.61％、CNLA 6.67％及CLA 9.46％，其他脂肪酸9.24％)。混合脂肪酸与三辛酸甘油酯按照摩尔比2.5:1混合，加入混合物质量5％的固定化脂肪酶LipozymeRM(诺维信公司产品)，一起置于50-60℃的恒温搅拌反应器中，反应器绝对压力为200Pa以下，反应时间为24h。反应物油相回收后经分子蒸馏分离纯化，分子蒸馏温度为190-200℃，分子蒸馏器工作绝对压力为0.1Pa以下，除去游离脂肪酸及其他低沸点组分，得到含有多不饱和脂肪酸及中短链脂肪酸的油脂组合物。甘油酯总脂肪酸组成见表1，该产品记为组合物4。
实施例5
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA多不饱和脂肪酸的乙酯为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA 20.25％、AA 8.53％、SDA 2.71％、ALA 6.23％、GLA3.61％、CNLA 6.67％及CLA9.46％，其他脂肪酸9.24％)。混合脂肪酸与三月桂酸甘油酯按照摩尔比3.5:1混合，加入混合物质量5％的固定化脂肪酶LipozymeRM(诺维信公司产品)，一起置于50-60℃的恒温搅拌反应器中，反应器绝对压力为100Pa以下，反应时间为24h。反应物油相回收后经分子蒸馏分离纯化，分子蒸馏温度为200-205℃，分子蒸馏器工作绝对压力为0.01Pa以下，除去脂肪酸乙酯及其他低沸点组分，得到含有多不饱和脂肪酸及中短链脂肪酸的油脂组合物。甘油酯总脂肪酸组成见表1，该产品记为组合物5。
对比实施例1
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA多不饱和脂肪酸为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA 20.25％、AA 8.53％、SDA 2.71％、ALA 6.23％、GLA3.61％、CNLA 6.67％及CLA 9.46％，其他脂肪酸9.24％)。混合脂肪酸与甘油酯按照摩尔比3.5:1混合，加入混合物质量5％的固定化脂肪酶Novozyme 435(诺维信公司产品)，一起置于50-60℃的恒温搅拌反应器中，反应器绝对压力为200Pa以下，反应时间为8h。反应物油相回收后经分子蒸馏分离纯化，分子蒸馏温度为180-190℃，分子蒸馏器工作绝对压力为1Pa以下，除去游离脂肪酸及其他低沸点组分，得到多不饱和脂肪酸甘油酯。甘油酯总脂肪酸组成见表1，该产品记为对比组合物1。
对比实施例2
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA、 多不饱和脂肪酸为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA 20.25％、AA 8.53％、SDA 2.71％、ALA 6.23％、GLA3.61％、CNLA 6.67％及CLA 9.46％，其他脂肪酸9.24％)，得到游离脂肪酸型多不饱和脂肪酸产品。总脂肪酸组成见表1，该产品记为对比组合物2。
对比实施例3
以市售的高纯度EPA、DHA、DPA、AA、SDA、ALA、GLA、CNLA及CLA多不饱和脂肪酸的乙酯为原料，按一定比例混合(EPA 18.60％、DHA 14.67％、DPA 20.25％、AA 8.53％、SDA 2.71％、ALA 6.23％、GLA3.61％、CNLA 6.67％及CLA 9.46％，其他脂肪酸9.24％)，得到乙酯型多不饱和脂肪酸产品。总脂肪酸组成见表1，该产品记为对比组合物3。
油脂组合物脂肪酸组成分析按“GB 5009.168-2016食品安全国家标准食品中脂肪酸的测定”，利用《GB/T 21121-2007动植物油脂氧化稳定性的测定(加速氧化测试)》方法，在90度，评估其氧化稳定性，得OSI值；结果见表1。
表1实验用油脂脂肪酸组成表
Figure PCTCN2020085237-appb-000002
Figure PCTCN2020085237-appb-000003
以组合物1-5和对比组合物1-3为评估对象，按照文献《1，3-甘油二酯微乳液的制备及生物利用度和安全评价》中公布的油脂生物利用度检验方法评估该组合物的PUFA生物利用度。实验动物选SD大鼠，购于南方医科大学实验动物中心SCXK(粤)2013-0034。维持饲料，购于广东省医学实验动物中心，许可证号：SCXK(粤)2013-0002。将大鼠用不含脂肪的日粮饲养，适应一星期后随机分为8组，每组9只，其中雌鼠4只，雄鼠5只。所有的动物自由的进食和饮水。将PUFA甘油酯组合物以1.6mg/g的添加量进行灌胃。灌胃2h后每个组分别取三只大鼠进行尾静脉取血，把血液收集后于离心，取上层血清储存于-20℃待测。实验最后一天收集每只大鼠的粪便。受试物的消化率通过测定脂肪的消化量即在粪便中没有检测出来的脂肪的量来确定。脂肪消化率可以通过以下公式来计算：PUFA消化率＝24h摄入PUFA脂肪量-24h粪便排出PUFA脂肪量/24h摄入PUFA脂肪量，结果如表4和表5所示。
由表2和表3可以看出，给大鼠灌胃2h后，本发明提供的PUFA甘油酯组合物实验组大鼠的血清中多不饱和脂肪酸含量和消化吸收率在显著大于对比组合物组，这说明本发明提供的PUFA甘油酯组合物中的PUFA具有更高的吸收率和生物利用度。
表2灌胃2h后血清中PUFA浓度(ug/ml)
Figure PCTCN2020085237-appb-000004
表3 PUFA消化吸收率
Figure PCTCN2020085237-appb-000005
Figure PCTCN2020085237-appb-000006
综合以上动物实验表明，与现有的PUFA甘油酯产品相比，本发明提供的PUFA甘油酯组合物具有更高效的降血脂、减肥功能，而且其中的PUFA具有更高的吸收率和生物利用度。

Claims (10)

  1. 一种油脂组合物，其特征在于，该组合物通式为：
    Figure PCTCN2020085237-appb-100001
    其中，甘油三酯的sn-1(3)位的脂肪酸酰基R1、R3为碳链长度为18～22个碳原子的多不饱和脂肪酸，sn-2位的脂肪酸酰基R2为中短链脂肪酸。
  2. 根据权利要求1中所述的油脂组合物，其特征在于，R2为乙酸、丁酸、己酸、辛酸、癸酸、月桂酸、豆蔻酸中的一种或两种以上的混合。
  3. 根据权利要求2中所述的油脂组合物，其特征在于，R2为丁酸、辛酸、月桂酸中的一种或两种以上的混合。
  4. 根据权利要求1或2或3所述的油脂组合物，其特征在于，R1、R3为二十碳五烯酸(EPA)、二十二碳六烯酸(DHA)、二十碳五烯酸(DPA)、花生四烯酸(AA)、十八碳四烯酸(SDA)、α-亚麻酸(ALA)、γ-亚麻酸(GLA)、共轭亚麻酸(CLNA)、共轭亚油酸(CLA)中的一种或两种以上的混合。
  5. 根据权利要求4所述的油脂组合物，其特征在于，R1和R3中，n-3PUFA的质量比例不低于50％。
  6. 根据权利要求5所述的油脂组合物，其特征在于，R1和R3中，n-3PUFA的质量比例不低于60％。
  7. 根据权利要求4所述的油脂组合物，其特征在于，R2中丁酸的质量比例不低于30％；R1和R3中，EPA的质量比例不低于15％。
  8. 根据权利要求7所述的油脂组合物，其特征在于，R2中丁酸的质量比例不低于50％；R1和R3中，EPA的质量比例不低于30％。
  9. 权利要求1～8任意一项所述的油脂组合物的制备方法，其特征在于，将两种以上多不饱和脂肪酸与中短链脂肪酸甘油酯按照摩尔比2.5:1混合，加入混合物质量5％的固定化脂肪酶LipozymeRM，置于50-60℃恒温搅拌反应，绝对压力为200Pa以下，反应时间为8h～24h；反应物油相回收后经分子蒸馏分离纯化，除去游离脂肪酸及其他低沸点组分，得到含有多不饱和脂肪酸及中短链脂肪酸的油脂组合物。
  10. 根据权利要求9所述油脂组合物的制备方法，其特征在于，所述分子蒸馏温度为180-190℃，分子蒸馏器工作绝对压力为1Pa以下。
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