WO2020244315A1 - 一种富含多不饱和脂肪酸的甘油酯混合物及其制备方法和应用 - Google Patents

一种富含多不饱和脂肪酸的甘油酯混合物及其制备方法和应用 Download PDF

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WO2020244315A1
WO2020244315A1 PCT/CN2020/085236 CN2020085236W WO2020244315A1 WO 2020244315 A1 WO2020244315 A1 WO 2020244315A1 CN 2020085236 W CN2020085236 W CN 2020085236W WO 2020244315 A1 WO2020244315 A1 WO 2020244315A1
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mixture
content
acid
less
fatty acids
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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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    • 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
    • A61K31/232—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

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  • the present invention is a glyceride composition rich in unsaturated fatty acids, which has more efficient absorption rate, lower blood fat and weight loss effects.
  • Polyunsaturated fatty acids generally refer to straight-chain fatty acids containing two or more double bonds and a carbon chain length of 18-22 carbon atoms.
  • Common PUFAs with special physiological functions for the human body mainly include eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), eicosapentaenoic acid (DPA), arachidonic acid (AA), Stearyl acid (SDA), ⁇ -linolenic acid (ALA), ⁇ -linolenic acid (GLA), conjugated linolenic acid (CLNA), and conjugated linoleic acid (CLA).
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • DPA eicosapentaenoic acid
  • AA arachidonic acid
  • SDA Stearyl acid
  • ALA ⁇ -linolenic acid
  • GLA ⁇ -
  • the existing PUFA products have insignificant and unstable effects in reducing blood fat and weight loss.
  • the main reason is that the content of PUFA in various products is low, the absorption rate of PUFA is not high when eating, and the products often contain multiple forms of PUFA (such as Fatty acids, ethyl esters, monoglycerides, diglycerides, triglycerides, phospholipids, etc.).
  • PUFA such as Fatty acids, ethyl esters, monoglycerides, diglycerides, triglycerides, phospholipids, etc.
  • the presence of these non-polyunsaturated fatty acid components and the presence of a variety of PUFA forms has seriously affected the bioavailability of various PUFAs, and reduced the blood lipid reduction of related products.
  • the purpose of the present invention is to provide a polyunsaturated fatty acid oil composition with high PUFA absorption rate and high-efficiency blood lipid lowering and weight loss functions.
  • a mixture rich in polyunsaturated fatty acid glycerides comprising not less than 95% glycerides and not more than 5% by weight of free fatty acids; the content of diglycerides in the glycerides is 30-98% by weight , The monoglyceride content is 0.1-70wt%, and the triglyceride content is 0-5wt%.
  • the ratio of sn-1,3:sn-1,2 in the composition of the diglyceride is not less than 1:1, and the ratio of sn-1(3):sn-2 in the monoglyceride is not less than 1:1.
  • the ratio of sn-1,3:sn-1,2 in the composition of the diglyceride is not less than 1.5:1, and the ratio of sn-1(3):sn-2 in the monoglyceride is not less than 1.5:1.
  • the polyunsaturated fatty acid is eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), eicosapentaenoic acid (DPA), arachidonic acid (AA), ten One or more of octatetraenoic acid (SDA), ⁇ -linolenic acid (ALA), ⁇ -linolenic acid (GLA), conjugated linoleic acid (CLNA), and conjugated linoleic acid (CLA) mixing.
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • DPA eicosapentaenoic acid
  • AA arachidonic acid
  • SDA octatetraenoic acid
  • ALA ⁇ -linolenic acid
  • GLA ⁇ -linolenic acid
  • CLNA conjugated linoleic acid
  • CLA conjugated lin
  • the ALA content in the polyunsaturated fatty acid is not less than 3 wt%
  • the EPA content is not less than 10 wt%
  • the DHA content is not less than 10 wt%
  • the mass ratio of DHA:EPA is not more than 5:1.
  • the content of ALA is 10-80wt%, more preferably 15-50wt%; the content of EPA is 20-90wt%, more preferably 20-80wt%.
  • the content of glycidyl ester in the mixture is less than 5 ppm, and the content of 3-chloro-1,2 propanediol ester is less than 5 ppm.
  • a method for preparing a mixture rich in polyunsaturated fatty acid glycerides including the following steps: using partial glyceride lipase Lipase G50 to catalyze the reaction of polyunsaturated fatty acids with glycerin to synthesize a mixture containing diglycerides and monoglycerides, and the mixture After centrifugal separation, the upper oil phase is recovered, and a mixture mainly composed of glycerides is obtained after separation.
  • the addition amount of Lipase G50 is 1-5%, the addition amount of water is 0.5-0.9%, and the reaction time is 12-24 hours.
  • the polyunsaturated fatty acid may be a single component or a mixture of multiple PUFAs.
  • the invention uses the synergistic effect of PUFA diglyceride and monoglyceride in the intake and exerting of physiological functions by directional design and control of the structural form of polyunsaturated fatty acid glycerides, and improves the blood lipid-lowering effect of PUFA while making it Has a more significant weight loss effect.
  • the oil and fat composition of polyunsaturated fatty acids in the present invention can be used as a dietary supplement, without changing people's dietary composition and eating habits, and at the same time by improving lipid metabolism, achieving the effects of lowering blood fat and losing weight.
  • the polyunsaturated fatty acid oil composition of the present invention mainly exists in the form of monoglycerides and diglycerides, which is a different kind from the existing commercially available polyunsaturated fatty acid ethyl ester or glyceride type products Fatty acid ester with special structure.
  • the present invention has the following beneficial effects:
  • the composition is based on the function of lowering blood lipids, effectively reducing excess fat and cholesterol in the body, thereby achieving the effects of dredging blood vessels, lowering blood lipids, losing weight and lowering blood pressure; compared with the existing PUFA products, the composition can effectively improve the biology of PUFA Utilization can effectively improve the blood fat and weight loss effects of PUFA.
  • Figure 1 is a microscope photograph of HE stained sections of experimental animal liver.
  • PUFA composition is CLA 10.85%, ALA 5.41%, GLA 3.22%, CNLA 1.04%, AA 10.28%, EPA 30.15%, DPA 3.14%, DHA 31.17%).
  • the partial glyceride lipase Lipase G50 (from penicillium camembertii, purchased from Amano Enzyme Preparation Co., Ltd.) is used to catalyze the reaction of fatty acids with glycerol to synthesize a mixture containing diglycerides and monoglycerides.
  • the addition amount of lipase is 1% and the amount of water added Is 0.5%.
  • the mixture is centrifuged, the upper oil phase is recovered, and the fatty acid is removed by molecular distillation to obtain a product with glycerides as the main component.
  • the diglyceride content in the product is 51.5%
  • the monoglyceride content is 46.0%
  • the triglyceride content is 2.1%
  • the free fatty acid content is 0.4%.
  • the total fatty acid composition of glycerides is shown in Table 1, and the glyceride product is recorded as composition 1.
  • PUFA composition is CLA 3.24%, ALA 6.01%, GLA 1.65%, CNLA 37.55%, AA 1.31%, EPA 20.75%, DPA 2.42%, DHA 21.42%).
  • the partial glyceride lipase Lipase G50 catalyzes the reaction of fatty acids and glycerol to synthesize a mixture containing diglycerides and monoglycerides.
  • the addition amount of lipase is 1%, and the addition amount of water is 0.5%.
  • the mixture is centrifuged, the upper oil phase is recovered, and the fatty acid is removed by molecular distillation to obtain a product with glycerides as the main component.
  • the diglyceride content of the product is 54.3%
  • the monoglyceride content is 42.7%
  • the triglyceride content is 2.2%
  • the free fatty acid content is 0.7%.
  • the total fatty acid composition of glycerides is shown in Table 1, and the glyceride product is recorded as composition 2.
  • PUFA composition is CLA 3.58%, ALA 5.94%, GLA 1.58%, CNLA 37.16%, AA 1.27%, EPA 20.53%, DPA 2.37%, DHA 21.83%).
  • the partial glyceride lipase Lipase G50 catalyzes the reaction of fatty acids and glycerol to synthesize a mixture containing diglycerides and monoglycerides.
  • the addition amount of lipase is 1%, and the addition amount of water is 0.5%.
  • the mixture is centrifuged, the upper oil phase is recovered, and the fatty acid is removed by molecular distillation to obtain a product with glycerides as the main component.
  • the diglyceride content of the product is 88.3%
  • the monoglyceride content is 10.4%
  • the triglyceride content is 1.2%
  • the free fatty acid content is 0.1%.
  • the total fatty acid composition of glycerides is shown in Table 1, and the glyceride product is recorded as composition 3.
  • PUFA composition is CLA 10.42%, ALA 5.21%, GLA 3.45%, CNLA 1.14%, AA 10.26%, EPA 30.74%, DPA 3.17%, DHA 30.88%) to prepare high-purity triglycerides rich in PUFA.
  • PUFA composition is CLA 10.42%, ALA 5.21%, GLA 3.45%, CNLA 1.14%, AA 10.26%, EPA 30.74%, DPA 3.17%, DHA 30.88%) to prepare high-purity triglycerides rich in PUFA.
  • Lipase Novozym435 and Lipase SMG1 are used to catalyze the reaction of fatty acids and glycerin to synthesize a PUFA-containing glyceride mixture.
  • the mixture is centrifuged, the upper oil phase is recovered and the fatty acids are removed by molecular distillation to obtain triglycerides as the main component.
  • the product After molecular distillation, the diglyceride content of the product is 3.1%, the monoglyceride content is 1.3%, the triglyceride content is 95.4%, and the free fatty acid content is 0.2%.
  • the total fatty acid composition of the glyceride is shown in Table 1, and the glyceride product is recorded as Comparative Composition 1.
  • PUFA composition is CLA 10.85%, ALA 5.41%, GLA 3.22%, CNLA 1.04%, AA 10.28%, EPA 30.15%, DPA 3.14%, DHA 31.17%) to prepare high-purity triglycerides rich in PUFA.
  • PUFA composition is CLA 10.85%, ALA 5.41%, GLA 3.22%, CNLA 1.04%, AA 10.28%, EPA 30.15%, DPA 3.14%, DHA 31.17%) to prepare high-purity triglycerides rich in PUFA.
  • Lipase Novozym435 and Lipase SMG1 are used to catalyze the reaction of fatty acids and glycerin to synthesize a PUFA-containing glyceride mixture.
  • the mixture is centrifuged, the upper oil phase is recovered and the fatty acids are removed by molecular distillation to obtain triglycerides as the main component.
  • the product After molecular distillation, the diglyceride content of the product is 2.7%, the monoglyceride content is 1.0%, the triglyceride content is 96.2%, and the free fatty acid content is 0.1%.
  • the total fatty acid composition of glycerides is shown in Table 1, and the glyceride product is recorded as comparative composition 2.
  • composition 3-5 and the comparative oil composition 3-4 were used as evaluation phases to evaluate the blood lipid-lowering effect of the composition.
  • Approximately 200 g of 70 SPF rats were adapted to an environment with a humidity of 55% at 23°C for 7 days. During the adaptation period, they were all fed with basic feed and drinking water, and they were free to eat. After the adaptation period, 70 rats were randomly divided into 8 groups (blank control group, model control group, Examples 1-3 and Comparative Examples 1-2), each with 10 rats. Rat. The blank group was fed basic feed during the experiment, and the remaining groups were fed high-fat feed (78.8% basic feed, 1% cholesterol, 0.2% No. 3 bile salt, 10% egg yolk powder, 10% lard).
  • Rats were intragastrically administered daily, and the blank control group and the model control group were intragastrically administered with 2.5mmol/L Tween-80 solution (10mL/(kg ⁇ bw)), Example 1-3 and Comparative Example 1-3.
  • the stomach was dissolved with 2.5mmol/L Tween-80 solution of PUFA glyceride, the dose was 2mL/(kg ⁇ bw), and each group was 10 rats.
  • blood samples were collected from the rats. The collected blood was centrifuged immediately, and the upper serum was taken to determine its total cholesterol (TC), high-density lipoprotein cholesterol (HDL-C), and low-density lipoprotein cholesterol (LDL-C).
  • TC total cholesterol
  • HDL-C high-den
  • Example 1-3 Compared with the blank group, there are significant differences in serum total cholesterol content and low-density lipoprotein content in Examples 1-3 and Comparative Example 1-2, indicating that the PUFA glyceride composition prepared by gavage Example 1-3 can make Hyperlipidemia rats' blood lipids returned to normal levels. Compared with the comparative example 1-2, the total cholesterol, low-density lipoprotein content and the ratio of the low-density lipoprotein to the high-density lipoprotein content in the serum of the gavage rats of Example 1-3 are significantly different, indicating that Example 1-3 The effect of lowering blood fat is significantly better than that of Comparative Example 1-2. It shows that the PUFA glyceride composition of the present invention has the effect of inhibiting the increase of blood total cholesterol, blood lipid and LDL, and can increase the level of serum HDL. Moreover, its function is better than the corresponding control composition.
  • composition 1-3 and the comparative oil composition 1-2 were used as evaluation phases to evaluate the weight loss effect of the composition.
  • SPF male SD rats weighing 150 ⁇ 20g, maintenance feed, high-fat feed purchased from Guangdong Medical Experimental Animal Center.
  • the obese rats were randomly divided into 7 groups according to their body weight, namely, blank control group (normal group), model control group (high-fat induced obesity model group), Example 1-3 and Comparative Example 1-2 groups .
  • Rats were administered intragastrically according to the dose of administration daily for 6 weeks. During the administration period, except the blank control group was given maintenance feed, the other groups were given high-fat feed. After the test, the rats' physical signs were detected, and the results are shown in Table 3 and Figure 1.
  • the PUFA glyceride composition of the present invention significantly reduces body weight, fat index, and obesity index, and the reduction effect is better than that of the corresponding comparative composition.
  • Figure 1 shows that within a certain field of view, the number of fat cells in the PUFA glyceride composition (A) is significantly less than that of the model group (B), and is better than the corresponding comparative composition group (C).
  • the above results show that the PUFA glyceride composition provided by the present invention can reduce the accumulation of fat, and the weight loss effect is better than the PUFA triglyceride product of the existing comparative composition.
  • the composition 1-3 and the comparative oil and fat composition 1-2 were used as the evaluation phases to evaluate the PUFA absorption efficiency of the composition.
  • the experimental animals were SD rats. The rats were fed with non-fat maintenance feed diets, and after adaptation for one week, they were randomly divided into 5 groups (one group for each of Examples 1-3 and Comparative Example), with 10 rats in each group. All animals eat and drink freely.
  • the PUFA glyceride composition was intragastrically administered at a dose of 1.2 mg/g. After gavage for 2 hours, blood was collected from the tail vein to determine the content of PUFA in the blood. The test results are shown in Table 4 below.
  • the PUFA glyceride composition experimental group provided by the present invention has significantly higher serum polyunsaturated fatty acid content and digestion and absorption rate than the comparative composition group.
  • the PUFA in the PUFA glyceride composition provided by the invention has a higher absorption rate.

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Abstract

一种富含多不饱和脂肪酸的甘油酯混合物及其制备方法和应用，所述混合物包括不低于95％的甘油酯和不高于5wt％的游离脂肪酸；所述甘油酯中甘油二酯的含量为30-98wt％，单甘酯含量为0.1-70wt％，甘油三酯含量为0-5wt％。该组合物提高了多不饱和脂肪酸的吸收率，而且具有降低血脂、减肥效果，可在制备减肥降脂的药物或保健品中应用。

Description

一种富含多不饱和脂肪酸的甘油酯混合物及其制备方法和应用 技术领域
本发明是富含不饱和脂肪酸的甘油酯组合物具有更高效的吸收率、降低血脂和减肥效果。
背景技术
随着社会经济的快速发展，人们的生活水平的提高，生活节奏也在不断加快，人们的饮食结构发生了巨大的改变，高脂高糖的快餐膳食结构日益占据了绝大部分市场。这就导致世界上许多国家的人群脂质代谢异常，高血脂、肥胖症的发病率和死亡率也随之增加，严重影响了人类健康。开展具有减肥降脂功能的膳食补充剂的研究开发符合社会发展的趋势，具有良好的应用前景。目前，市场上针对肥胖、高血脂症状的膳食补充剂产品主要以左旋肉碱、不饱和脂肪酸等为主。
多不饱和脂肪酸(PUFA)一般是指含有两个或两个以上双键且碳链长度为18～22个碳原子的直链脂肪酸。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)、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)。大量的研究证实，PUFA因具有独特的生理功能，在功能性食品、医药、保健品领域有着越来越多的应用。
现有的PUFA制品降血脂、减肥效果不显著，不稳定，主要原因是各类产品中PUFA的含量较低，食用时PUFA的吸收率不高，而且产品中往往是多种PUFA存在形式(如脂肪酸、乙酯、甘油一酯、甘油二酯、甘油三酯、磷脂等)的混合。 这些非多不饱和脂肪酸成分以及多种PUFA存在形式的混合的存在，严重影响了各种PUFA的生物利用效率，降低了相关制品的降血脂。
发明内容
针对现有PUFA产品降血脂、减肥等保健效果不理想、不稳定的问题，本发明的目的是提供一种PUFA吸收率高、且具有高效降血脂、减肥功能的多不饱和脂肪酸油脂组合物。
一种富含多不饱和脂肪酸甘油酯的混合物，所述混合物包括不低于95％的甘油酯和不高于5wt％的游离脂肪酸；所述甘油酯中甘油二酯的含量为30-98wt％，单甘酯含量为0.1-70wt％，甘油三酯含量为0-5wt％。
优选地，甘油二酯的组成中sn-1,3:sn-1,2的比例不低于1:1，单甘油酯中sn-1(3):sn-2不低于1:1。
优选地，甘油二酯的组成中sn-1,3:sn-1,2的比例不低于1.5:1，单甘油酯中sn-1(3):sn-2不低于1.5:1。
优选地，所述多不饱和脂肪酸为二十碳五烯酸(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，所述多不饱和脂肪酸中ALA含量不低于3wt％，EPA含量不低于10wt％，DHA含量不低于10wt％，且DHA:EPA质量比例不高于5:1。
优选地，其中ALA的含量为10-80wt％，更优选15-50wt％；其中EPA的含量为20-90wt％，更优选20-80wt％。
优选地，混合物中缩水甘油酯的含量小于5ppm，3-氯-1,2丙二醇酯的含量 小于5ppm。
一种富含多不饱和脂肪酸甘油酯的混合物的制备方法，包括如下步骤：利用偏甘油酯脂肪酶Lipase G50催化多不饱和脂肪酸与甘油反应合成含有甘油二酯和单甘油酯的混合物，将混合物进行离心分离，回收上层油相后，经分离得到以甘油酯为主的混合物。
优选地，所述酯化反应中脂肪酶Lipase G50的添加量为1-5％，水分添加量为0.5-0.9％，反应时间为12-24h。
所述富含多不饱和脂肪酸甘油酯的混合物在制备减肥降脂的药物或保健品中的应用。
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。本发明通过对多不饱和脂肪酸甘油酯的结构形式进行定向设计和控制，利用PUFA甘油二酯和单甘油酯在摄入和发挥生理功能中的协同作用，提高PUFA的降血脂效果的同时使其具有更显著的减肥效果。本发明中多不饱和脂肪酸的油脂组合物可以作为一种膳食补充剂，在不改变人们的膳食组成、不改变人们的饮食习惯，的同时通过改善脂质代谢，达到降血脂、减肥的效果。本发明的多不饱和脂肪酸的油脂组合物存在形式以单甘油酯和甘油二酯为主，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。与乙酯或甘油三酯型多不饱和脂肪酸油脂经过人体消化吸收后多不饱和脂肪酸更多的存在于甘油酯的sn-2位相比，富含多不饱和脂肪酸的单甘油酯和甘油二酯经过人体消化吸收后，大量的sn-1(3)-单甘酯在人体小肠内再合成为甘油三酯时，大大的增加了多不饱和脂肪酸在sn-1(3)的存在，表现出了更为突出的功能性作用。
与现有技术相比，本发明具有以下有益效果：
该组合物以降血脂为功能基础，有效减少体内多余脂肪和胆固醇，从而达到疏通血管，降低血脂、减肥和降低血压的效果；该组合物相对于现有的PUFA类产品，可以有效提高PUFA的生物利用度，可以有效提高PUFA的降血脂及减肥效果。
附图说明
图1为实验动物肝脏HE染色切片显微镜拍照图片。
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。
实施例1
以市售鱼油脂肪酸、藻油脂肪酸、亚麻酸、共轭亚油酸为原料，按一定比例混合(PUFA组成为CLA 10.85％，ALA 5.41％，GLA 3.22％，CNLA 1.04％，AA 10.28％，EPA 30.15％，DPA 3.14％，DHA 31.17％)。利用偏甘油酯脂肪酶Lipase G50(来源于penicilliumcamembertii,购自日本天野酶制剂公司)催化脂肪酸与甘油反应合成含有甘油二酯和单甘油酯的混合物，脂肪酶的添加量为1％，水分添加量为0.5％。酯化反应12h后，将混合物进行离心分离，回收上层油相后并利用分子蒸馏分离除去其中的脂肪酸得到以甘油酯为主要成分的产物。分子蒸馏后产品中的甘油二酯含量为51.5％，单甘油酯含量为46.0％，甘油三酯含量为2.1％，游离脂肪酸含量为0.4％。甘油酯总脂肪酸组成见表1，该甘油酯产品记为组合物1。
实施例2
以市售鱼油脂肪酸、共轭亚油酸、亚麻酸、石榴籽油脂肪酸为原料，按一定比例混合(PUFA组成为CLA 3.24％，ALA 6.01％，GLA 1.65％，CNLA 37.55％，AA 1.31％，EPA 20.75％，DPA 2.42％，DHA 21.42％)。利用偏甘油酯脂肪酶Lipase G50催化脂肪酸与甘油反应合成含有甘油二酯和单甘油酯的混合物，脂肪酶的添加量为1％，水分添加量为0.5％。酯化反应12h后，将混合物进行离心分离，回收上层油相后并利用分子蒸馏分离除去其中的脂肪酸得到以甘油酯为主要成分的产物。分子蒸馏后产品中的甘油二酯含量为54.3％，单甘油酯含量为42.7％，甘油三酯含量为2.2％，游离脂肪酸含量为0.7％。甘油酯总脂肪酸组成见表1，该甘油酯产品记为组合物2。
实施例3
以市售鱼油脂肪酸、共轭亚油酸、亚麻酸、石榴籽油脂肪酸为原料，按一定比例混合(PUFA组成为CLA 3.58％，ALA 5.94％，GLA 1.58％，CNLA 37.16％，AA 1.27％，EPA 20.53％，DPA 2.37％，DHA 21.83％)。利用偏甘油酯脂肪酶Lipase G50催化脂肪酸与甘油反应合成含有甘油二酯和单甘油酯的混合物，脂肪酶的添加量为1％，水分添加量为0.5％。酯化反应12h后，将混合物进行离心分离，回收上层油相后并利用分子蒸馏分离除去其中的脂肪酸得到以甘油酯为主要成分的产物。分子蒸馏后产品中的甘油二酯含量为88.3％，单甘油酯含量为10.4％，甘油三酯含量为1.2％，游离脂肪酸含量为0.1％。甘油酯总脂肪酸组成见表1，该甘油酯产品记为组合物3。
对比实施例1
以市售鱼油脂肪酸、藻油脂肪酸、亚麻酸、共轭亚油酸为原料，按一定比例混合(PUFA组成为CLA 10.42％，ALA 5.21％，GLA 3.45％，CNLA 1.14％，AA 10.26％，EPA 30.74％，DPA 3.17％，DHA 30.88％)，制备富含PUFA的高纯度甘油三酯。利用脂肪酶Novozym435和Lipase SMG1联合催化处理脂肪酸与甘油反应合成含有PUFA的甘油酯混合物，将混合物进行离心分离，回收上层油相后并利用分子蒸馏分离除去其中的脂肪酸得到以甘油三酯为主要成分的产物。分子蒸馏后产品中的甘油二酯含量为3.1％，单甘油酯含量为1.3％，甘油三酯含量为95.4％，游离脂肪酸含量为0.2％。甘油酯总脂肪酸组成见表1，该甘油酯产品记为对比组合物1。
对比实施例2
以市售鱼油脂肪酸、共轭亚油酸、亚麻酸、石榴籽油脂肪酸为原料，按一定比例混合(PUFA组成为CLA 10.85％，ALA 5.41％，GLA 3.22％，CNLA 1.04％，AA 10.28％，EPA 30.15％，DPA 3.14％，DHA 31.17％)，制备富含PUFA的高纯度甘油三酯。利用脂肪酶Novozym435和Lipase SMG1联合催化处理脂肪酸与甘油反应合成含有PUFA的甘油酯混合物，将混合物进行离心分离，回收上层油相后并利用分子蒸馏分离除去其中的脂肪酸得到以甘油三酯为主要成分的产物。分子蒸馏后产品中的甘油二酯含量为2.7％，单甘油酯含量为1.0％，甘油三酯含量为96.2％，游离脂肪酸含量为0.1％。甘油酯总脂肪酸组成见表1，该甘油酯产品记为对比组合物2。
利用相关标准方法进行本发明的油脂组合物脂肪酸组成分析及降血脂、减肥、PUFA生物利用度评估。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”，结果见表1。
表1实验用油脂脂肪酸组成表
Figure PCTCN2020085236-appb-000001
Figure PCTCN2020085236-appb-000002
降血脂评价：
以组合物3-5和对比油脂组合物3-4为评估对相，评估该组合物的降血脂效果。将70只SPF级大鼠200g左右在23℃湿度为55％的环境下适应7天，适应期间全部喂养基础饲料和饮用水，自由取食。适应期后将70只大鼠随机分为8组(空白对照组、模型对照组、实施例1-3及对比例1-2)，每组10只，淘汰掉体重较平均值低以及病态的大鼠。其中空白组在实验期间喂养基础饲料，剩余组均喂养高脂饲料(78.8％基础饲料，1％胆固醇,0.2％3号胆盐，10％蛋黄粉，10％猪油)。每天对大鼠进行灌胃，其中空白对照组、模型对照组灌胃2.5mmol/L的吐温-80溶液(10mL/(kg·bw))、实施例1-3及对比例1-3灌胃用2.5mmol/L的吐温-80溶液溶解的PUFA甘油酯，剂量为2mL/(kg·bw)，每组10只大鼠。以78.8％的基础饲料，1％的胆固醇，10％的猪油，10％的蛋黄粉以及0.2％的胆盐3号为高脂饲料，连续饲养大鼠，使其血清胆固醇达到3.77士0.41mmol/L即建模成功。稳定喂养6周即42天后，采集大鼠血样。采集的血液立即离心，取上层血清测定其总胆固醇(TC)、高密度脂蛋白胆固醇(HDL-C)、低密度脂蛋白胆固醇(LDL-C)。
表2实验动物血液指标分析
  TG TC HDL LDL
空白组 1.22±0.83 2.45±1.24 1.41±0.28 0.72±0.18
模型组 1.96±0.75 3.81±1.35 1.35±0.48 2.10±0.33
组合物1 1.03±0.47 2.21±1.13 1.533±0.58 0.33±0.21
组合物2 1.12±0.61 2.19±1.02 1.514±0.75 0.41±0.19
组合物3 1.04±0.55 2.10±0.72 1.527±0.37 0.36±0.16
对比组合物1 1.38±0.73 2.43±1.32 1.415±0.83 0.73±0.08
对比组合物2 1.47±0.54 2.61±0.97 1.472±0.64 0.77±0.11
通过动物试验观察发现，由表2可以看出，与模型组相比，实施例1-3及对比例1-3灌胃蚕蛹油脂组大鼠的低密度脂蛋白含量、低密度脂蛋白与高密度脂蛋白含量之比降低明显，差异显著；与模型组相比，实施例1-3及对比例1-2PUFA甘油酯组大鼠血清中总胆固醇降低明显；说明富含PUFA的甘油酯可以显著降低高脂大鼠血清中的总胆固醇含量和低密度脂蛋白含量。与空白组相比，实施例1-3及对比实施例1-2中血清总胆固醇含量和低密度脂蛋白含量差异显著，说明通过灌胃实施例1-3制备的PUFA甘油酯组合物可以使高脂大鼠血脂恢复到正常水平。相比于对比例1-2，实施例1-3灌胃大鼠血清中总胆固醇、低密度脂蛋白含量及低密度脂蛋白与高密度脂蛋白含量之比差异显著，说明实施例1-3降血脂效果显著好于对比例1-2。说明本发明的PUFA甘油酯组合物具有抑制血液总胆固醇、血脂、LDL升高的作用，并且能够提高血清HDL的水平。而且，其功能优于相应的对照组合物。
减肥评价：
以组合物1-3和对比油脂组合物1-2为评估对相，评估该组合物的减肥效果。SPF级雄性SD大鼠，体重150±20g，维持饲料、高脂饲料，购于广东省医学实验动物中心。造模结束后，将肥胖大鼠按体重随机分成7组，即空白对照组(正常组)、模型对照组(高脂诱导肥胖模型组)、实施例1-3及对比实施例1-2组。 大鼠每日按给药剂量灌胃给药，连续给药6周。给药期间除空白对照组给予维持饲料，其余各组给予高脂饲料。试验结束后，检测大鼠体征指标，结果如表3及图1所示。由表3可以看出，本发明PUFA甘油酯组合物与对照组相比，体重、脂肪指数、肥胖指数均明显降低，而且降低效果优于相应的对比组合物。图1显示在一定视野范围内，脂肪细胞数PUFA甘油酯组合物(A)的明显少于模型组(B)，而且优于相应的对比组合物组(C)。以上结果表明，本发明提供的PUFA甘油酯组合物能够减少脂肪的堆积，而且减肥效果优于现有对比组合物的PUFA甘油三酯产品。
表3各组大鼠生长指标及脂类代谢测定值
  体重 脂肪指数 肥胖指数 肝指数
对照组 443.82±14.47 2.91±0.67 27.17±0.34 2.74±0.11
模型组 516±28.41 4.51±1.67 34.61±0.43 2.76±0.63
组合物1 406±22.35 2.31±0.65 22.73±0.32 2.56±0.55
组合物2 387±18.46 2.42±0.79 21.87±0.46 2.24±0.72
组合物3 394±24.63 2.23±0.18 21.44±0.39 2.45±0.54
对比组合物1 429±20.54 2.78±27 26.47±0.33 2.76±0.61
对比组合物2 431±26.87 2.86±41 25.93±0.45 2.69±0.48
吸收率评价：
以组合物1-3和对比油脂组合物1-2为评估对相，评估该组合物的PUFA的吸收效率。实验动物选SD大鼠。将大鼠用不含脂肪的维持饲料日粮饲养，适应一星期后随机分为5组(实施例1-3及对比实施例各一组)，每组10只。所有的动物自由的进食和饮水。将PUFA甘油酯组合物以1.2mg/g的剂量进行灌胃。灌胃2h后进行尾静脉取血，测定血液中PUFA含量。检测结果见下表4。
表4灌胃2h后血清脂质中PUFA含量(ug/ml)
Figure PCTCN2020085236-appb-000003
由表4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。

Claims (10)

  1. 一种富含多不饱和脂肪酸的甘油酯混合物，其特征在于，所述混合物包括不低于95％的甘油酯和不高于5wt％的游离脂肪酸；所述甘油酯中甘油二酯的含量为30-98wt％，单甘酯含量为0.1-70wt％，甘油三酯含量为0-5wt％。
  2. 根据权利要求1所述的混合物，其特征在于，甘油二酯的组成中sn-1,3:sn-1,2的比例不低于1:1，单甘油酯中sn-1(3):sn-2不低于1:1。
  3. 根据权利要求1所述的混合物，其特征在于，甘油二酯的组成中sn-1,3:sn-1,2的比例不低于1.5:1，单甘油酯中sn-1(3):sn-2不低于1.5:1。
  4. 根据权利要求1或2或3所述的混合物，其特征在于，所述多不饱和脂肪酸为二十碳五烯酸(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所述的混合物，其特征在于，所述多不饱和脂肪酸中ALA含量不低于3wt％，EPA含量不低于10wt％，DHA含量不低于10wt％，且DHA:EPA质量比例不高于5:1。
  6. 根据权利要求5所述的混合物，其特征在于，其中ALA的含量为10-80wt％，优选为15-50wt％；其中EPA的含量为20-90wt％，优选为20-80wt％。
  7. 根据权利要求1或2或3所述的混合物，其特征在于，混合物中缩水甘油酯的含量小于5ppm，3-氯-1,2丙二醇酯的含量小于5ppm。
  8. 一种富含多不饱和脂肪酸甘油酯的混合物的制备方法，其特征在于，包括如下步骤：利用偏甘油酯脂肪酶Lipase G50催化多不饱和脂肪酸与甘油反应合成含有甘油二酯和单甘油酯的混合物，将混合物进行离心分离，回收上层油相后，经分离得到以甘油酯为主的混 合物。
  9. 根据权利要求8所述的制备方法，其特征在于，所述酯化反应中脂肪酶Lipase G50的添加量为1-5％，水分添加量为0.5-0.9％，反应时间为12-24h。
  10. 权利要求1～7任意一项所述的混合物或权利要求8或9制得的混合物在制备减肥降脂的药物或保健品中的应用。
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