CN103242407A - Polyunsaturated fatty acyl group-containing phosphatidyl sterol and/or phosphatidyl stanol, and preparation method and application of same - Google Patents

Polyunsaturated fatty acyl group-containing phosphatidyl sterol and/or phosphatidyl stanol, and preparation method and application of same Download PDF

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Publication number
CN103242407A
CN103242407A CN2013101791424A CN201310179142A CN103242407A CN 103242407 A CN103242407 A CN 103242407A CN 2013101791424 A CN2013101791424 A CN 2013101791424A CN 201310179142 A CN201310179142 A CN 201310179142A CN 103242407 A CN103242407 A CN 103242407A
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phosphatidyl
sterol
acyl group
stanols
organic solvent
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张雅茹
王西岭
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Priority to PCT/CN2014/076313 priority patent/WO2014183550A1/en
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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
    • A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/60—Drinks from legumes, e.g. lupine drinks
    • A23L11/65—Soy drinks
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C11/00—Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/10—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins
    • A23C11/103—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins containing only proteins from pulses, oilseeds or nuts, e.g. nut milk
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P33/00—Preparation of steroids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6481—Phosphoglycerides

Abstract

The invention provides phosphatidyl sterol and/or phosphatidyl stanol rich in polyunsaturated fatty acyl group, and a preparation method of the same, and mainly solves the technical problems that the existing phytosterol is poor in solubility and low in bioavailability, toxic agents are used in the preparation method of ester of the existing phytosterol, the reaction conditions are rigorous, and industrial production cannot be realized, and the like. The structural formula of phosphatidyl sterol and/or phosphatidyl stanol is shown in the specification, wherein Sn-1, Sn-2 and Sn-3 respectively refer to position 1, position 2 and position 3 of glyceride group in phospholipid; R1 and R2 are one of the following groups: -C19H29, -C19H31, -C21H31 or -C21H33, and X is sterol or stanol. The polyunsaturated fatty acyl group-containing phosphatidyl sterol and/or phosphatidyl stanol can effectively lower the effect value of cholesterol and triglyceride content in blood plasma; and application field and range of the polyunsaturated fatty acyl group-containing phosphatidyl sterol and/or phosphatidyl stanol are also provided.

Description

The phosphatidyl sterol and/or phosphatidyl stanols and the preparation method and application that contain the polyunsaturated fat acyl group
Technical field
The present invention relates to prepare the phosphatidyl sterol that is rich in many insatiable hungers fatty acyl group and/or phosphatidyl stanols and preparation method thereof with enzymatic method; Verified that the phosphatidyl sterol that is rich in many insatiable hungers fatty acyl group and/or phosphatidyl stanols are worth as functional food or the medicine effect for reducing cholesterol in the blood plasma and content of triglyceride; And Application Areas and the scope of phosphatidyl sterol and/or the phosphatidyl stanols of many insatiable hungers fatty acyl group have been determined to be rich in.
Background technology
Cardiovascular disorder has become the healthy important disease of harm humans, these disease cause of disease complexity, but with abnormalities of sugar/lipid metabolism very close relationship is arranged.Numerous studies show that, low-density lipoprotein (LDL) cholesterol is directly related with the outbreak of cardiovascular disorder, and high-density lipoprotein (HDL) (HDL) cholesterol then has opposite relation with cardiovascular outbreak.And suffer from the people of associating hyperlipidemia even have the cardiopathic danger of higher outbreak.Plasma cholesterol and triglyceride content raise and are considered to cause and the sign of cardiovascular disorder usually.And reducing cholesterol content and triglyceride reducing content are considered to prevent the main policies of cardiovascular disorder.
Reducing plasma cholesterol content by the picked-up plant sterol is a kind of relatively valid approach.Plant sterol is the basic chemical ingredients of plant, and less is present in the vegetables oil (as Semen Maydis oil, soya-bean oil or other plant oil).In vegetables oil, they are to exist with free sterol, fatty acid ester and glucosides form.Plant sterol is similar to cholesterol on chemical structure, and the key distinction is the carbon skeleton of their molecular side chains.Occurring in nature, modal plant sterol comprise-Sitosterol, brassicasterol, campesterol, Stigmasterol.The saturated plant sterol that plant sterol is reduced generation is called as phytostanols, for example campestanol (campestanol) or sitostanol (sitostanol).
Structure and the cholesterol structure of plant sterol are similar, they can form limited competitive relation with cholesterol in small intestine, can substitute the part cholesterol and be absorbed, and plant sterol can not be utilized in human body itself, thereby can reach the content that reduces low density cholesterol in the blood plasma.But plant sterol is water insoluble, and solubleness is also very little in oil, thereby limits its application in food or medicine greatly.Many research work are all round the structural modification of plant sterol and launch, and more common work comprises with chemical process and/or enzymatic methods of conversion the hydroxyl on the plant sterol 3-position and free fatty acids prepared in reaction are obtained the phytosterol fatty acid ester.The solubleness of plant sterol fat acid esters in grease is than higher, can be more convenient apply to various foods, and to the not influence of the final taste of product, fragrance and physical properties.Except being applied to food ingredients, plant sterol ester can also be made into soft capsule preparation clinically for reducing cholesterol.
Phosphatide (Phospholipid) is the lipoid cpd of phosphorous acid group, and structure is phosphinylidyne two glycerol fatty acid esters.Phosphatide can be divided into glyceryl alcohol phosphatide and neural pure phosphatide two big classes by its molecular structure difference.Mainly comprise phosphatidylserine (Phosphatidylserine, PS), phosphatidylcholine (Yelkin TTS, Phosphatidylcholine, PC), phosphatidylethanolamine (kephalin, Phosphatidylethanolamine, PE), phosphatidylinositols (Phosphatidylinositol, PI) and phosphatidic acid (Phosphatidic acid, PA).Phosphatide is the important composition composition that constitutes cytolemma, and it is the basic substance of the activity of earning a bare living.Phosphatide has all multiactions such as the brain function of improvement, reducing cholesterol, anti-stress.
Different sources phosphatide, its lipid acid constitute obviously different.The phosphatide of plant origin, as soybean phospholipid, the fatty acyl group that is connected on its glyceryl 1 Sn-1 and 2 Sn-2 mostly is saturated fatty acyl group or inferior oleoyl, flax acyl group, does not contain how saturated polyenoid key fatty acyl group, as two dodecahexaene acyl groups (Docosahexaenoic Acid ,DHA), and the eicosa-pentaenoic acyl group (Eicosapntemacnioc Acid, EPA) etc.And the phosphatide of animal-origin; phosphatide as bathypelagic fish, krill source; be connected fatty acyl group on its glyceryl 1 Sn-1 and 2 Sn-2 and mostly be the polyunsaturated fat acyl group; this polyunsaturated fat acyl group mainly comes from polyunsaturated fatty acid; for example fatty acyl content such as DHA, EPA are higher in the phosphatide of animal-origin, and have important physiological function.A large amount of scientific researches in recent years show, polyunsaturated fatty acid, and for example Omega-3 polyunsaturated fatty acid DHA, EPA are proved to be the effect with triglyceride levels in the remarkable reduction blood plasma, and relevant with the metabolism of cholesterol.So-called polyunsaturated fatty acid, emphasis point of the present invention is emphasized arachidonic acid (AA), timnodonic acid (EPA), clupanodonic acid (DPA), docosahexenoic acid polyunsaturated fatty acid and their mixtures such as (DHA).
Up to the present, carried out following work, the plant sterol that will dissociate is converted into its esterified form, thus broadened application.
US5502045 discloses the application of sitostanol fatty acid ester aspect the minimizing cholesterol absorption, but uses poisonous organic solvent in preparation process, and the preparation condition harshness.
US2372990 disclose by use after the methylene dichloride enrichment-Sitosterol and fatty acid methyl ester generation transesterification reaction prepare the phytosterol fatty acid ester.Same, use noxious solvent and condition harshness in this preparation process.
US0068425 discloses a kind of manufacture method of phytosterol fatty acid ester, is catalyzer but use the bigger thionyl chloride of pollution in manufacturing processed, and the operational condition harshness, is difficult to suitability for industrialized production.
Publication number CN 1982326A discloses and has a kind ofly used rudimentary sodium alkoxide to be the preparation method of Preparation of Catalyst multiple unsaturated fatty acid phytosterin fat under high vacuum condition, but the operational condition harshness is difficult to suitability for industrialized production.
Plant sterol fat and/or phytostanols fat that EP98122412.4 discloses the polyunsaturated fatty acid with 18～22 carbon atoms and at least 3 carbon-to-carbon double bonds can effectively reduce plasma cholesterol and triglyceride level.This patent disclosure how unsaturated polyenoid key lipid acid, as DHA, EPA, be combined the effect that forms sterol ester and reduce cholesterol and content of triglyceride in the blood plasma with plant sterol.
Above-mentioned sterol ester structure is the directly fatty acid ester that combines of the hydroxyl dehydrating condensation of the carboxyl by lipid acid and sterol of lipid acid and sterol.
Publication number CN102365031 A discloses a kind of method of utilizing acyltransferase catalysis plant sterol/phytostanols and plant phosphatide to prepare the phosphatidyl plant sterol ester.But this patent disclosure be the phosphatide of plant sterol and plant origin through the phosphatidyl plant sterol ester that enzyme catalysis generates, in its phosphatide ester structure, do not contain polyunsaturated fatty acid, for example DHA, DPA, EPA etc.
The phosphatidyl choline that will contain many insatiable hungers fatty acyl group; for example glyceryl 1 Sn-1 and/or 2 Sn-2 go up and are many insatiable hungers fatty acyl group (arachidonic acid (AA) especially; timnodonic acid (EPA); clupanodonic acid (DPA); the acyl group that docosahexenoic acid polyunsaturated fatty acids such as (DHA) and their mixture are derived) phosphatidyl choline; under Phospholipase D catalysis; with plant sterol or phytostanols generation transesterification; generation contains phosphatidyl plant sterol or the phosphatidyl phytostanols of many insatiable hungers fatty acyl group; and utilize the phosphatidyl plant sterol or the phosphatidyl phytostanols that contain many insatiable hungers fatty acyl group to reduce cholesterol and triglyceride level in the blood plasma; at present also without any bibliographical information, it is the novel achievement of a very meaningful and using value.
Summary of the invention
The purpose of this invention is to provide a kind of phosphatidyl sterol that contains many insatiable hungers fatty acyl group and/or phosphatidyl stanols and its production and use, mainly solve existing plant sterol poorly soluble, bioavailability low with and the carboxylate preparation method in use toxic reagent, severe reaction conditions and can't suitability for industrialized production etc. technical problem.
Technical scheme of the present invention is: a kind of phosphatidyl sterol and/or phosphatidyl stanols that contains many insatiable hungers fatty acyl group, and structural formula is as follows:
Figure 854001DEST_PATH_IMAGE001
In the formula: Sn-1, Sn-2 and Sn-3 refer to 1,2 and 3 of glyceryl ester group in the phosphatide respectively; R 1And R 2Be long carbochain fatty acyl group, the Sn-1 position-R1 and Sn-2 position-R 2Common has-C 19H 29,-C 19H 31,-C 21H 31,-C 21H 33For example if R 1Or R 2For-C 19H 29, R then is described 1Or R 2From timnodonic acid (being EPA) ,-C 19H 29Coupled carbonyl group constitutes an eicosa-pentaenoic fatty acyl group, and being illustrated in Sn-1 or Sn-2 position is a pure ester that forms of Sn-1 or Sn-2 position that timnodonic acid is corresponding with glycerol molecule; If it is-C 19H 31, R then is described 2From eicosatetraenoic acid or arachidonic acid ,-C 19H 31Coupled carbonyl group constitutes an Eicosatetraenoic fatty acyl group, and being illustrated in Sn-1 or Sn-2 position is a pure ester that forms of Sn-1 or Sn-2 position that eicosatetraenoic acid is corresponding with glycerol molecule; If it is-C 21H 31, R then is described 2From docosahexenoic acid (being DHA) ,-C 21H 31Coupled carbonyl group constitutes two dodecahexaene fatty acyl groups, and being illustrated in Sn-1 or Sn-2 position is a pure ester that forms of Sn-1 or Sn-2 position that docosahexenoic acid is corresponding with glycerol molecule; If it is-C 21H 33, R then is described 2From clupanodonic acid (being DPA) ,-C 21H 33Coupled carbonyl group constitutes a docosapentaenoic fatty acyl group, and being illustrated in Sn-1 or Sn-2 position is a pure ester that forms of Sn-1 or Sn-2 position that clupanodonic acid is corresponding with glycerol molecule; The Sn-3 position-X is different linking group, if-X is sterol, then this phosphatide cpd is the phosphatidyl sterol ester, in this article, is called the phosphatidyl sterol according to custom; If-X is stanols, then this phosphatide cpd is the phosphatidyl stanol ester, in this article, is called the phosphatidyl stanols according to custom.
Sterol or stanols are selected from compound or the mixture of following structural formula:
Figure 585196DEST_PATH_IMAGE002
Sterol preferably-Sitosterol (being the Beta-Sitosterol) or Stigmasterol or its mixture, most preferably be-Sitosterol.Stanols preferably-sitostanol or stigmastanol or its mixture, most preferably be-sitostanol (Beta-sitostanol).
A kind of preparation method who contains phosphatidyl sterol and/or the phosphatidyl stanols of many insatiable hungers fatty acyl group; may further comprise the steps: the phosphatidyl choline that will contain many insatiable hungers fatty acyl group; for example glyceryl 1 Sn-1 and/or 2 Sn-2 go up and are many insatiable hungers fatty acyl group (arachidonic acid (AA) especially; timnodonic acid (EPA); clupanodonic acid (DPA); the acyl group that docosahexenoic acid polyunsaturated fatty acids such as (DHA) and their mixture are derived) phosphatidyl choline; then at water and organic solvent two-phase mixed system or contain in the organic solvent single_phase system of minor amount of water; under Phospholipase D catalysis; with plant sterol or phytostanols generation transesterification, generate the phosphatidyl plant sterol and/or the phosphatidyl phytostanols that contain many insatiable hungers fatty acyl group.
The phosphatidyl plant sterol that contains many insatiable hungers fatty acyl group that the present invention prepares or phosphatidyl phytostanols reduce that cholesterol and triglyceride level can effectively reduce cholesterol and content of triglyceride in the blood plasma in the blood plasma.
The invention further relates to and contain the phosphatidyl plant sterol that contains many insatiable hungers fatty acyl group that the present invention prepares or the nutrient supplement food composition of phosphatidyl phytostanols.This nutrient supplement food composition can replenish the form of transfer system for soft capsule, tablet, syrup or any other ordinary diet meal.
The invention further relates to and contain the phosphatidyl plant sterol that contains many insatiable hungers fatty acyl group that the present invention prepares or the functional food of phosphatidyl phytostanols.Such functional food can be selected from milk preparation, milk beverage, ice cream, baked goods, pan work, biscuit, bean product, cake and bread, energy bar, soy sauce, seasonings, oil ﹠ fat, oleomargarine, sauce, cereal, beverage and mixing drink, infant food (biscuit, puree, puree and cereal), bar shaped food, snack, chocolate.
The invention further relates to and contain the phosphatidyl sterol that contains many insatiable hungers fatty acyl group that the present invention prepares and/or the pharmaceutical composition of phosphatidyl stanols, its optional at least a medicine acceptable additive, thinner or excipient of also containing.Pharmaceutical composition of the present invention is optional also can to contain at least a forms of pharmacologically active agents.
Purpose of the present invention realizes by following measure:
One, preparation contains phosphatidyl sterol or the phosphatidyl stanols of many insatiable hungers fatty acyl group:
Step 1: preparation contains the phosphatidylcholine of many insatiable hungers fatty acyl group: include but not limited to the phosphatidylcholine of producing by following several disclosed methods that contains many insatiable hungers fatty acyl group, or the commodity of buying with following feature:
1, certain must lipid acid generates the phosphatidylcholine that contains necessary fatty acyl group with phosphatidylcholine in the soybean phospholipid to adopt lipase or phospholipase A catalysis;
2, the phosphatidylcholine that is rich in the polyunsaturated fat acyl group that from Living marine resources, extracts, so-called Living marine resources are including but not limited to following species: krill, the fish-egg of tuna, salmon or sardines, squid, the bathypelagic fish liver oil, etc.;
3, the phosphatidylcholine that is rich in the polyunsaturated fat acyl group that the microbial fermentation of genus mortierella prepares.
Step 2: preparation enzymic catalytic reaction system, described reaction system is the two-phase reaction system of water and organic solvent phase composite or the organic solvent homogeneous reaction system that contains micro-moisture.The phosphatidylcholine that is rich in many insatiable hungers fatty acyl group for preparing for step 1 of one of reaction substrate wherein, two of reaction substrate is plant sterol and/or phytostanols, plant sterol and/or phytostanols can be in-Sitosterol, brassicasterol, campesterol, Stigmasterol and the alkanol thereof one or more, and its source is in soybean oil, peanut oil, Semen Maydis oil, sesame oil, tea-seed oil, sunflower seed oil, rapeseed oil or the other plant oil one or more; The preferred plant sterol; More preferably derive from soybean oil, peanut oil, Semen Maydis oil, sesame oil, tea-seed oil, sunflower seed oil, plant sterol mixture in rapeseed oil or the other plant oil, this plant sterols mixture is-Sitosterol, Stigmasterol, campesterol, brassicasterol and-sitostanol, stigmastanol, campestanol, the mixture of vegetable seed stanols etc., this plant sterols mixture normally-Sitosterol, Stigmasterol, campesterol, sterols such as brassicasterol are main component, and-sitostanol, stigmastanol, campestanol, vegetable seed stanols etc. is submember.
Step 3 joins the reaction system of step 2 in the reactor, and temperature is 35 ~ 55 degrees centigrade, drops into to continue mechanical stirring behind the Phospholipase D and react.
Step 4, with step 3 gained reaction solution re-extract 2 ~ 3 times, after the layering of liquid liquid organic solvent subtracted each other force down that temperature concentrates and drying after be prepared into phosphatidyl sterol and/or the stanols that is rich in many insatiable hungers fatty acyl group;
The phosphatidyl sterol that contains many insatiable hungers fatty acyl group and/or phosphatidyl stanols that the described preparation of step 4 obtains, can contain tens molecular series, wherein the chemical structure of each molecular series has following identical and different: (1) is all to be connected a plant sterol or phytostanols on the Sn-3 at glyceryl 3; (2) on glyceryl 1 Sn-1 and 2 Sn-2, be connected a fatty acyl group separately, and on 1 Sn-1 and/or 2 Sn-2, connect the long-chain fat acyl group that contains many unsaturated link(age)s usually, there is the fatty acyl group that is higher than more than 5% to contain unsaturated double-bond more than 2 in the fatty acyl group that its implication connects for the Sn-2 position, or there is the fatty acyl group that is higher than more than 3% to contain the Omega-3 unsaturated double-bond in the fatty acyl group of its implication for the connection of Sn-2 position, or have the fatty acyl group that is higher than 5% or more to contain unsaturated double-bond more than 2 in the fatty acyl group that connects for the Sn-1 position of its implication, or there is the fatty acyl group that is higher than more than 3% to contain the Omega-3 unsaturated double-bond in the fatty acyl group of its implication for the connection of Sn-1 position; (3) the unsaturated double-bond fatty acyl group that contains contains 18 to 22 carbon atoms; and the number of two keys is generally three to six, and described unsaturated fatty acyl group lay special stress on derives from the acyl group of following many unsaturated fatty acids: arachidonic acid (AA), timnodonic acid (EPA), clupanodonic acid (DPA), docosahexenoic acid polyunsaturated fatty acid and their mixtures such as (DHA).These unsaturated fatty acyl groups are the phosphatidylcholines that are rich in unsaturated fatty acyl that derive from the step 1, can derive from the enzyme catalysis modified-reaction, also can derive from so-called Living marine resources in the step 1.
The described enzymic catalytic reaction system of step 2 is the two-phase hybrid reaction system of water and organic solvent phase composite or the organic solvent homogeneous reaction system that contains micro-moisture; its implementation process is: earlier the phosphatidylcholine that is rich in the polyunsaturated fat acyl group for preparing in the step 1; also has plant sterol or/and phytostanols; dissolve in C5-C9 alkane organic solvent; and then the pure and mild or short hydrocarbon ketone of adding short hydrocarbon; add the aqueous buffer solution that contains calcium salt again; thereby form the reaction system that water and organic solvent two-phase mix or the organic solvent homogeneous reaction system that contains micro-moisture; the proportion relation of each material is as follows in the described aqueous solution and the organic solvent two-phase hybrid reaction system: the percent weight in volume that phosphatidylcholine adds in every liter of mixed reaction solution is 0.5%～10%; the percent weight in volume that plant sterol and/or phytostanols add in every liter of reaction solution is 1%～30%; the percent weight in volume that calcium salt adds in every liter of reaction solution is 0.001%～10%; the concentration of buffering salt then is 0～2 mol in the buffered soln; the volume percent that C5-C9 alkane organic solvent occupies in mixed reaction solution is 5% ~ 95%; short hydrocarbon alcohol or short hydrocarbon ketone possessive volume per-cent in total mixed reaction solution is 1% ~ 80%, and the pH value of the aqueous solution and organic solvent two-phase hybrid reaction system is in 4.0 ~ 8.5.
Described C5-C8 alkane organic solvent is optional from following article: the mixed solvent that any solvent in pentane, hexane, hexanaphthene, heptane, octane, nonane, decane or their isomers or these solvents form with any mixed.
Described short hydrocarbon alcohol or short hydrocarbon ketone are optional from following article: the mixed solvent that any solvent in ethanol, propyl alcohol, butanols, amylalcohol, acetone, butanone or their isomers or these solvents form with any mixed.
Two, contain the phosphatidyl sterol of polyunsaturated fat acyl group and/or phosphatidyl stanols for the effect that reduces cholesterol and content of triglyceride in the blood plasma
Can confirm that by rat test the phosphatidyl sterol that contains the polyunsaturated fat acyl group that the present invention prepares and/or phosphatidyl stanols have the effect that reduces cholesterol and content of triglyceride in the blood plasma, the method for application and the result of acquisition are summarized as follows:
1, animal is handled
The purebred rat of male Wistar that to choose 30 weight in the pre-treatment in 2 weeks be 150 ± 20g provides high lipid food to raise (food composition sees Table 1).Then they are divided into immediately 5 experiment groups, every group of 6 rats.For making whole experimental foods have energy and the fat of same amount, use the 2%(w/w) following lipid replaces 2% lipid content (1% Oleum Cocois and 1% Semen Maydis oil) in control group (1 group) food:
1 group: 2% lipid content (1% Oleum Cocois and 1% Semen Maydis oil, w/w)
2 groups: 2% Sitosterol mixture/high oily Trisun Oil R 80 (1:1 ratio, w/w)
3 groups: 2% Sitosterol-DHA phosphatide ester, Sitosterol-DHA phosphatide ester also can be described as the phosphatidyl Sitosterol that contains the DHA acyl group;
4 groups: 2% Stigmasterol-EPA phosphatide ester, Stigmasterol-EPA phosphatide ester also can be described as the phosphatidyl Stigmasterol that contains the EPA acyl group;
5 groups: 2% plant sterol and stanols mixture-EPA/DHA phosphatide ester (1:1 ratio, w/w), sterol mixture-EPA/DHA phosphatide ester also can be described as phosphatidyl plant sterol and the phosphatidyl phytostanols that contains EPA and/or DHA acyl group.
The fatty acid compositional analysis of experimental foods the results are shown in Table 2.The raising condition is standard conditions: room temperature (24 ± 1 ℃), relative humidity (55 ± 10) %.Allow rat freely look for food and water, and they are kept bright/dark circulation in 12 hours.Replace food in the cage every day, discard leftover and measure intake.(0) week and processing 2 week backs (the 2nd week) are by paracentesis district blood sample (1ml) behind the socket of the eye when trial period begins.After 4 weeks, from the deadly rat of Vena cava blood drawing, blood sample is kept in the sample hose that contains EDTA.
2, lipid analysis
Resulting blood sample was prepared blood plasma immediately in centrifugal 20 minutes under 4 ℃, 1600g.Measure total cholesterol, triglyceride level and HDL-cholesterol level in the blood plasma by Biochemical Analyzer, and calculate non-HDL cholesterol level by minusing.It is to pass through gas chromatography determination that lipid acid in the food is formed.
3, statistical study
All data all are expressed as mean value ± SD, and analyze by individual event covariance (ANCOVA).All experiment is carried out under 5% level, and calculates 95% fiducial interval.
4, the result
In 4 all feeding periods, all rat upgrowth situations are similar.5 groups of average food rations of rat are 19g/ days/.Foodstuff processing does not have obviously variant to body weight and food consumption.
In all four experimental group (the 2nd, 3,4,5 groups) of handling with plant sterol, plasma cholesterol content reduces greatly, namely reduces by 44%～47%(with respect to comparative group) and reduce by 56%～67%(with respect to pre-treatment period (0 week)) (table 3).Almost do not influence HDL cholesterol level (table 4) by handling with plant sterol.Therefore non-HDL cholesterol (VLDL cholesterol+LDL cholesterol) is mainly handled by plant sterol and is reduced.
In the experimental group of handling with phosphatidyl sterol and/or the phosphatidyl stanols of polyunsaturated fat acyl group the (the 3rd; 4; 5 groups) in; content of triglyceride reduces greatly in the blood plasma; namely reduce by 36%～41%(with respect to comparative group) and reduce by 24%～38%(with respect to the processing phase (0 week)) (table 5), but plant sterol and vegetables oil combination (the 2nd group) does not significantly reduce content of triglyceride in the blood plasma.
The composition of table 1 rat high lipid food
Table 2, the lipid acid of test food is formed (fatty acid methyl ester mol%)
Figure 145939DEST_PATH_IMAGE004
Table 3 contains the phosphatidyl sterol of polyunsaturated fat acyl group and/or phosphatidyl stanols to the effect (mmol/L) of rat plasma total cholesterol
Figure 945267DEST_PATH_IMAGE005
A is with respect to changing with the percentage of handling;
B is when the 2nd week or the 4th week significantly different with comparative group (P＜0.05);
C is in the 2nd week or the 4th when week and the 2nd group significantly different (P＜0.05);
Table 4 contains the phosphatidyl sterol of polyunsaturated fat acyl group and/or phosphatidyl stanols to the effect (mmol/L) of rat lipoprotein
A is when the 2nd week or the 4th week significantly different with comparative group (P＜0.05);
B is in the 2nd week or the 4th when week and the 2nd group significantly different (P＜0.05);
Table 5 contains the phosphatidyl sterol of polyunsaturated fat acyl group and/or phosphatidyl stanols to the effect (mmol/L) of sweet three esters of rat plasma
A is with respect to changing with the percentage of handling;
B is when the 2nd week or the 4th week significantly different with comparative group (P＜0.05);
C is in the 2nd week or the 4th when week and the 2nd group significantly different (P＜0.05).
Three, contain the phosphatidyl sterol that contains the polyunsaturated fat acyl group that the present invention prepares and/or the nutrient supplement food composition of phosphatidyl stanols.
New constituent of the present invention can transmit in various products and utilize.Such product comprises foodstuff additive, functional food, pharmacy transfer system etc.
The phosphatidyl sterol that contains the polyunsaturated fat acyl group and/or phosphatidyl stanols that the present invention prepares can be processed to the nutrient supplement food composition, and can replenish the form of transfer system for soft capsule, tablet, syrup or any other ordinary diet meal.This nutrient supplement food composition purpose is intended to reduce people's plasma cholesterol and content of triglyceride.Nutrient supplement food composition of the present invention is preferably used with the amount that restrains every day 0.2～200.Preferred plant sterol has-Sitosterol, Stigmasterol, campesterol, brassicasterol or their any mixed thing.Preferred have-Sitosterol and Stigmasterol or its mixture.Most preferably-Sitosterol.Preferred phytostanols has-sitostanol and campestanol or its mixture.More preferably-sitostanol.The phosphatide of preferred polyunsaturated fat acyl group refers to contain arachidonic acid (AA), timnodonic acid (EPA), clupanodonic acid (DPA), docosahexenoic acid polyunsaturated fatty acid and the formed fatty acyl group phosphatide of their mixture such as (DHA).DHA and the EPA fatty acyl group phosphide of deriving most preferably.
Four, contain the phosphatidyl sterol that contains the polyunsaturated fat acyl group that the present invention prepares and/or the functional food of phosphatidyl stanols.
The sterol ester that the present invention prepares and/or plant stanol ester can be used as functional ingredient, add to be prepared in the bread and cheese to have the functional food that reduces human plasma cholesterol and content of triglyceride.Such functional food can be selected from milk preparation, milk beverage, ice cream, baked goods, pan work, biscuit, bean product, soymilk, cake and bread, energy bar, soy sauce, seasonings, oil ﹠ fat, oleomargarine, sauce, cereal, beverage and mixing drink, infant food (biscuit, puree, puree and cereal), bar shaped food, snack, chocolate, puffed food etc.
Such functional food preferably with every day 0.1～100 gram polyunsaturated fat acyl group the phosphatidyl sterol and/or the total amount of phosphatidyl stanols use.Preferred plant sterol has-Sitosterol, Stigmasterol, campesterol, brassicasterol or their mixture.Preferredly have-Sitosterol, Stigmasterol or its mixture.Most preferably-Sitosterol.Preferred phytostanols has-sitostanol, campestanol, vegetable seed stanols or their mixture.More preferably-sitostanol.Preferred polyunsaturated fat acyl phospholipids refers to contain arachidonic acid (AA), timnodonic acid (EPA), clupanodonic acid (DPA), docosahexenoic acid polyunsaturated fatty acid and the formed fatty acyl group phosphatide of their mixture such as (DHA).DHA and the EPA fatty acyl group phosphide of deriving most preferably.
Five, contain the phosphatidyl sterol of the polyunsaturated fat acyl group that the present invention prepares and/or the pharmaceutical composition of phosphatidyl stanols.
Preparation of drug combination is well-known in this area, in many documents and book of reference description is arranged, and for example participating in, Gennaro A. R. edits (1990) Remington ' s Pharmaceutical Science, Mack Publishing Company, Easton, Pennsylvania, as medicinal product, the pharmaceutical composition that the present invention prepares can be oral, intravenously or by other any routines or specially give the approach transmission.
Understand easily, the phosphatidyl sterol of the polyunsaturated fat acyl group that the present invention prepares and/or phosphatidyl stanols need not used with the pure state compound form.Can use the mixture of these esters.Can use the mixture of other aliphatic esters of these phosphatidyl sterols that contain the polyunsaturated fat acyl group and/or phosphatidyl stanols equally.The product that the present invention prepares can be the form of liquid oil, powder, particle, wax, paste, oiliness or water-based emulsion, and can make it be used for any other form of target purposes.
Compared with prior art; the present invention has following advantage: 1) the present invention utilizes the phosphatidylcholine that contains the polyunsaturated fat acyl group that public technology prepares; the plant sterol that for example derives from the phosphatidylcholine that contains the polyunsaturated fat acyl group of krill oil roe etc. and derive from soybean is reactant, the phosphatidyl plant sterol and the phosphatidyl phytostanols that utilize the Phospholipase D bioconversion method to prepare to be rich in the polyunsaturated fat acyl group.Products material is easy to get, reaction conditions gentleness, simple and practical.And such target compound is up to the present without any bibliographical information.2) the phosphatidyl sterol of the polyunsaturated fat acyl group for preparing of the present invention and/or phosphatidyl stanols can effectively reduce cholesterol and content of triglyceride in the blood plasma simultaneously.3) the phosphatidyl sterol of the polyunsaturated fat acyl group for preparing of the present invention and/or phosphatidyl phytostanols can obtain using widely in foodstuff additive, functional food, pharmacy transfer system.
Embodiment
For just good understanding content of the present invention, be described further below in conjunction with specific embodiment.Should be understood that following examples are only for explanation the present invention but not for limiting scope of the present invention.
A kind of preparation contains the method for phosphatidyl sterol and/or the phosphatidyl stanols of polyunsaturated fat acyl group, preparation process the following step:
Step 1, preparation contains the phosphatidylcholine of many insatiable hungers fatty acyl group: include but not limited to the several different methods of mentioning by " summary of the invention " part.Here only with from the phosphatidylcholine in krill oil or the tuna ovum; this polyunsaturated fat acyl phospholipids phatidylcholine raw material that is rich in; for the example explanation is made with extra care being rich in polyunsaturated fat acyl phospholipids phatidylcholine raw material; prepare the phosphatidylcholine that contains many insatiable hungers fatty acyl group with lipase or phosphide enzyme A1 or phospholipase A 2; principle is simple; any technician with biology or catalysis background; equal enzymic catalytic reactions routinely; be substrate with polyunsaturated fatty acid and the phosphatidylcholine Yelkin TTS of phosphatidyl choline (or contain); catalyze and synthesize, therefore repeat no more here.
Adopt solvent extraction to prepare phosphatidylcholine.Described solvent can be chosen wantonly in following article: the normal heptane of aliment security level or normal hexane, edible ethanol or acetone or their mixture.To be krill oil or tuna ovum mix the back with solvent in nitrogen environment, under 0 ~ 30 degree centigrade at reactor in described extraction, through mechanical stirring, reacted 0.5 ~ 15 hour, after the filtration solid lyophilize got phosphatidylcholine.The described phosphatidylcholine of obtaining is the phosphatide family of being rich in the polyunsaturated fat acyl group, tens phosphatidylcholine molecules series are contained in this phosphatidylcholine family, and wherein the chemical structure of each molecular series has following identical and different: (1) is all to be connected a choline on the Sn-3 at glyceryl 3; (2) on glyceryl 1 Sn-1 and 2 Sn-2, be connected a fatty acyl group separately, and on 1 Sn-1 and/or 2 Sn-2, can connect a long-chain fat acyl group that contains how unsaturated polyenoid key, describedly be rich in how unsaturated polyenoid key fatty acyl group, its implication is to have the fatty acyl group that is higher than 5% or more to contain unsaturated double-bond more than 2 in the fatty acyl group that connects of Sn-1 and/or Sn-2 position, or its implication is to have the fatty acyl group that is higher than more than 3% to contain the Omega-3 unsaturated double-bond in the fatty acyl group of Sn-1 and/or the connection of Sn-2 position; (3) the unsaturated double-bond fatty acyl group that contains contains 18 to 22 carbon atoms; and the number of two keys is generally four to six, and described unsaturated fatty acyl group lay special stress on derives from the acyl group of following many unsaturated fatty acids: arachidonic acid (AA), timnodonic acid (EPA), clupanodonic acid (DPA), docosahexenoic acid polyunsaturated fatty acid and their mixtures such as (DHA).
Step 2, the enzymic catalytic reaction system.Described reaction system is the two-phase reaction system of water and organic solvent phase composite; its implementation process is: earlier the phosphatidylcholine that is rich in the polyunsaturated fat acyl group for preparing in the step 1; also has plant sterol or/and phytostanols; dissolve in C5-C9 alkane organic solvent; and then the pure and mild or short hydrocarbon ketone of adding short hydrocarbon; add the aqueous buffer solution contain calcium salt again, thereby form the reaction system that water and organic solvent two-phase mix or the organic solvent homogeneous reaction system that contains micro-moisture.The proportion relation of each material is as follows in the described aqueous solution and the organic solvent hybrid reaction system: the percent weight in volume that phosphatidylcholine adds in every liter of mixed reaction solution is 0.5%～10%, the percent weight in volume that sterol and/or stanols add in every liter of reaction solution is 1%～30%, the percent weight in volume that calcium salt adds in every liter of reaction solution is 0.001%～10%, the concentration of buffering salt then is 0～2 mol in the buffered soln, the volume percent that C5-C9 alkane organic solvent occupies in mixed reaction solution is 5% ~ 95%, short hydrocarbon alcohol or short hydrocarbon ketone possessive volume per-cent in total mixed reaction solution is 1% ~ 80%, and the pH value of the aqueous solution and organic solvent two-phase hybrid reaction system is in 4.0 ~ 8.5.The described organic solvent homogeneous reaction system that contains micro-moisture; its implementation process is: the phosphatidylcholine that is rich in the polyunsaturated fat acyl group for preparing in the step 1; also has plant sterol or/and phytostanols; dissolve in through the C5-C9 of processed alkane organic solvent; can select to add or do not add the pure and mild or short hydrocarbon ketone through the short hydrocarbon of processed, add the Phospholipase D dry powder that contains calcium salt again.The proportion relation of each material is as follows in the described organic solvent single_phase system that contains minor amount of water: the percent weight in volume that phosphatidylcholine adds in every liter of mixed reaction solution is 0.5%～10%, the percent weight in volume that sterol and/or stanols add in every liter of reaction solution is 1%～30%, the percent weight in volume that calcium salt adds in every liter of reaction solution is 0.001%～10%, the volume percent that C5-C9 alkane organic solvent occupies in mixed reaction solution is 50% ~ 95%, short hydrocarbon alcohol or short hydrocarbon ketone possessive volume per-cent in total mixed reaction solution is 0% ~ 50%, the content of water is extremely low in this system, can't form aqueous phase layer with the organic phase layering.
Described C5-C8 alkane organic solvent is optional from following article: the mixed solvent that any solvent in pentane, hexane, hexanaphthene, heptane, octane, nonane, decane or their isomers or these solvents form with any mixed.The preferred normal heptane of this step and normal hexane or their isomers.
Described short hydrocarbon alcohol or short hydrocarbon ketone are optional from following article: the mixed solvent that any solvent in ethanol, propyl alcohol, butanols, amylalcohol, acetone, butanone or their isomers or these solvents form with any mixed.The preferred Virahol of this step or acetone.
In this step, plant sterol: commercial biological product can be from the plant sterol as extracting soybean oil, rapeseed oil, plam oil, the cottonseed wet goods vegetables oil, wherein-Sitosterol content is greater than 40%, Stigmasterol content is greater than 5%, campesterol is greater than 5%, with brassicasterol content 0～10%, total sterol content can reach 90%; Calcium salt: inorganic and organic calcium salt all can, what present embodiment adopted is calcium chloride and calcium sulfate, the concentration in water can be 0.01 gram and whenever rises to every liter of 100 gram; Damping fluid: be conventional water damping fluid, for example phosphoric acid brine buffer solution or acetic acid brine buffer solution are generally 0 to 2 mole of every liter of salt concn system.
Step 3 joins the reaction system of step 2 in the reactor, in nitrogen environment, temperature is 35 ~ 55 ℃, continues mechanical stirring after dropping into phosphatide plum D, and churning time is 1 ~ 24 hour.
In this step, Phospholipase D: being a kind of proteolytic enzyme, is the commercialization zymin that derives from microorganism and/or plant, as (the St. Louis of Sigma-Aldrich company, MO, the U.S.A.) Phospholipase D of Chu Shouing (phospholipase D), but this enzyme also purifying from the fermented liquid of microorganism.Phospholipase D can be the dry powder zymin, also can be liquid enzyme preparation.For the organic solvent homogeneous reaction system that contains minor amount of water, used Phospholipase D is the dry powder zymin that contains calcium salt.
Step 4 with step 3 gained reaction solution re-extract 1 ~ 3 time, after liquid-liquid layering, prepares phosphatidyl sterol and/or the stanols that is rich in the polyunsaturated fat acyl group with the lyophilize of organic phase concentrating under reduced pressure, finishes preparation.Identical in extraction solvent and extracting process and the step 1 in this step.
According to said method Zhi Bei the phosphatidyl plant sterol that contains how unsaturated polyenoid key fatty acyl group and/or stanol ester quality percentage composition can be higher than 5%, through after refining processing, the quality percentage composition reaches 5% to 95%.
Below the most preferred embodiment of the present invention in concrete the application is elaborated, these embodiment retrain scope of the present invention.
Embodiment 1: the phosphatidylcholine of polyunsaturated fat acyl group is rich in preparation.
Take by weighing 20 kilograms of Oils,glyceridic,cod-liver, it contains: EPA is that 18.6 ± 1.4%, DHA is 12.3 ± 2.1%; PC content is 46.0 ± 3.0%, 80 liters of acetone, and above-mentioned two kinds of raw materials are joined in 100 liters of reactors; in reactor, charge into nitrogen; continue mechanical stirring, after 2 hours, filter; the solid lyophilize is obtained being rich in about 13.1 ± 2.4 kilograms of the phosphatidylcholine of polyunsaturated fat acyl group; wherein: EPA is that 26.5 ± 2.1%, DHA is that 17.8 ± 2.2%, PC content is 67.3 ± 3.2%.
Embodiment 2: the phosphatidylcholine of polyunsaturated fat acyl group is rich in preparation.
Take by weighing 20 kilograms of krill oil, it contains: EPA is that 14.2 ± 2.8%, DHA is 8.8 ± 2.3%; PC content is 40.4 ± 3.6%, 60 liters of acetone, and above-mentioned two kinds of raw materials are joined in 100 liters of reactors; in reactor, charge into nitrogen; continue mechanical stirring, after 4 hours, filter; the solid lyophilize is obtained being rich in about 11.8 ± 2.2 kilograms of the phosphatidylcholine of polyunsaturated fat acyl group; wherein: EPA is that 19.1 ± 3.6%, DHA is that 12.2 ± 3.0%, PC content is 68.8 ± 4.2%.
Embodiment 3: the phosphatidylcholine of polyunsaturated fat acyl group is rich in preparation.
Take by weighing 20 kilograms of tuna ovum, it contains: EPA is that 10.6 ± 1.3%, DHA is 22.3 ± 1.9%; PC content is 44.0 ± 1.0%, 80 liters of acetone, and above-mentioned two kinds of raw materials are joined in 100 liters of reactors; in reactor, charge into nitrogen; continue mechanical stirring, after 2 hours, filter; the solid lyophilize is obtained being rich in about 14.1 ± 1.4 kilograms of the phosphatidylcholine of polyunsaturated fat acyl group; wherein: EPA is that 16.5 ± 2.3%, DHA is that 27.8 ± 2.5%, PC content is 54.3 ± 3.2%.
Embodiment 4: the phosphatidylcholine of polyunsaturated fat acyl group is rich in preparation.
Take by weighing 20 kilograms of soybean phospholipids (PC content 50% ± 5.0%); in reactor, be dissolved in the normal hexane; charge into nitrogen; the DHA and the EPA lipid acid (DHA/EPA is about 3/2) that add 20 kilograms of microbial sources; after fully stirring; it is an amount of to add commercial lipase; under 45 degrees centigrade; detection reaction product behind the reaction appropriate time reaches total phospholipids about 50%, then stopped reaction if contain the phosphatide of polyunsaturated fat acyl group; add 100 liters of acetone; continue mechanical stirring, after 3 hours, filter; the solid lyophilize is obtained being rich in about 17.8 ± 1.4 kilograms of the phosphatidylcholine of polyunsaturated fat acyl group; wherein: EPA is that 15.1 ± 0.4%, DHA is that 10.2 ± 0.3%, PC content is 56.5 ± 0.5%.
Embodiment 5: preparation contains the phosphatidyl sterol of polyunsaturated fat acyl group
In 1000 liters of reactors; add in 300 kilograms of normal heptanes; add 100 kilograms of Virahols; then 30 kilograms of mass percentage concentration 90% plant sterols (are derived from corn; wherein-Sitosterol 40.6%; Stigmasterol: 23.9%; campesterol: 24.9%; brassicasterol content 0.6%) 13.1 kilograms that prepare with embodiment 1 contain polyunsaturated fat acyl phospholipids phatidylcholine and add in the reactor; dissolve 0.05 kilogram of calcium chloride; the aqueous solution of 600 liters of pH5.6; under nitrogen protection; drop into 40,000 unit Phospholipase Ds; in 40 degrees centigrade; continue mechanical stirring; react and stopped in 8 hours stirring; finish reaction; standing demix is got organic phase, the normal heptane during according to reaction and the ratio of Virahol; press the relation with 1:1; re-extract residue mother liquor 1 to 2 time, the set organic extract liquid is evaporated to basic organic solvent-free under 40 degrees centigrade; add an amount of pure water; emulsification is filtered and is removed insolubles, adds 40 liters of acetone again; the filtered and recycled precipitation; precipitation is soaked for some time with 40 liters of acetone again, filtered and recycled and 12.5 ± 0.5 kilograms of throw outs of dry acquisition, and wherein the phosphatidyl sterol content is 40.4 ± 1.2%; in the throw out unsaturated fatty acid content after testing EPA be that 24.7 ± 1.8%, DHA is 16.4 ± 1.2%.
Embodiment 6: preparation contains the phosphatidyl sterol of polyunsaturated fat acyl group
In 1000 liters of reactors; add in 300 kilograms of normal heptanes; add 50 kilograms of Virahols; then 40 kilograms of mass percentage concentration 90% plant sterols (are derived from soybean; wherein-and Sitosterol: 44.2%; Stigmasterol: 26.3%; campesterol: 22.3%; brassicasterol content 1.7%) 11.8 kilograms that prepare with embodiment 2 contain polyunsaturated fat acyl phospholipids phatidylcholine and add in the reactor; dissolve 0.1 kilogram of calcium chloride; the aqueous solution of 300 liters of pH5.6; under nitrogen protection; drop into 50,000 unit Phospholipase Ds; in 48 degrees centigrade; continue mechanical stirring; react and stopped in 4 hours stirring; finish reaction; standing demix is got organic phase, the normal heptane during according to reaction and the ratio of Virahol; press the relation with 1:1; re-extract residue mother liquor 1 to 2 time, the set organic extract liquid is evaporated to basic organic solvent-free under 40 degrees centigrade; add an amount of pure water; emulsification is filtered and is removed insolubles, adds 50 liters of acetone again; the filtered and recycled precipitation; precipitation is soaked for some time with 50 liters of acetone again, filtered and recycled and 11.2 ± 0.6 kilograms of throw outs of dry acquisition, and wherein the phosphatidyl sterol content is 41.1 ± 1.2%; in the throw out unsaturated fatty acid content after testing EPA be 16.3 ± 1.47 %, DHA is 10.1 ± 1.5%.
Embodiment 7: preparation contains the phosphatidyl sterol of polyunsaturated fat acyl group
In 1000 liters of reactors; add in 300 kilograms of normal heptanes; add 50 kilograms of Virahols; then 40 kilograms of mass percentage concentration 90% plant sterols (are derived from soybean; wherein-and Sitosterol: 44.2%; Stigmasterol: 26.3%; campesterol: 22.3%; brassicasterol content 1.7%) 14.1 kilograms that prepare with embodiment 3 contain polyunsaturated fat acyl phospholipids phatidylcholine and add in the reactor; dissolve 0.1 kilogram of calcium chloride; the aqueous solution of 300 liters of pH5.6; under nitrogen protection; drop into 50,000 unit Phospholipase Ds; in 48 degrees centigrade; continue mechanical stirring; react and stopped in 4 hours stirring; finish reaction; standing demix is got organic phase, the normal heptane during according to reaction and the ratio of Virahol; press the relation with 1:1; re-extract residue mother liquor 1 to 2 time, the set organic extract liquid is evaporated to basic organic solvent-free under 40 degrees centigrade; add an amount of pure water; emulsification is filtered and is removed insolubles, adds 50 liters of ethanol again; the filtered and recycled precipitation; precipitation is used 50 liters of alcohol immersion for some time again, filtered and recycled and 12.3 ± 0.5 kilograms of throw outs of dry acquisition, and wherein the phosphatidyl sterol content is 40.1 ± 1.3%; in the throw out unsaturated fatty acid content after testing EPA be that 16.9 ± 1.6%%, DHA is 10.8 ± 1.3%.
Embodiment 8: preparation contains the phosphatidyl sterol of polyunsaturated fat acyl group
In 1000 liters of reactors; add in 300 kilograms of normal heptanes; add 50 kilograms of Virahols; then 60 kilograms of mass percentage concentration 90% plant sterols (are derived from sunflower seeds; wherein-Sitosterol 42.8%; Stigmasterol: 21.7%; campesterol: 24.1%; brassicasterol content 1.4%) with embodiment 4 in 10.0 kilograms of phosphatidylcholines obtaining add in the reactors; dissolve 0.5 kilogram of calcium chloride under nitrogen protection, drop into 50,000 unit Phospholipase Ds, in 40 degrees centigrade of scopes; continue mechanical stirring; react and stopped in 12 hours stirring, finish reaction, under 40 degrees centigrade, be evaporated to basic organic solvent-free; add 50 liters of ethanol; stir and soaked 12 hours, filtered and recycled and 14.2 ± 0.5 kilograms of throw outs of dry acquisition, wherein the phosphatidyl sterol content is 38.1 ± 1.5%; in the throw out unsaturated fatty acid content after testing EPA be that 14.6 ± 1.4%%, DHA is 9.2 ± 1.1%.
Embodiment 9: preparation contains the phosphatidyl sterol of polyunsaturated fat acyl group
In 1000 liters of reactors; add in 300 kilograms of normal heptanes; add 60 kilograms of Virahols; then 60 kilograms of mass percentage concentration 90% plant sterols (are derived from soybean; wherein-and Sitosterol: 44.2%; Stigmasterol: 26.3%; campesterol: 22.3%; brassicasterol content 1.7%) with embodiment 3 in 10.0 kilograms of phosphatidylcholines obtaining add in the reactors; dissolve 0.5 kilogram of calcium chloride under nitrogen protection, drop into 50,000 unit Phospholipase Ds, in 48 degrees centigrade; continue mechanical stirring; react and stopped in 4 hours stirring, finish reaction, under 40 degrees centigrade, be evaporated to basic organic solvent-free; add 50 liters of ethanol; stir and soaked 4 hours, filtered and recycled and 13.8 ± 0.5 kilograms of throw outs of dry acquisition, wherein the phosphatidyl sterol content is 38.4 ± 1.4%; in the throw out unsaturated fatty acid content after testing EPA be that 14.5 ± 1.1%%, DHA is 9.3 ± 1.0%.
Embodiment 10: preparation contains the phosphatidyl sterol of polyunsaturated fat acyl group
In 1000 liters of reactors; add in 300 kilograms of normal heptanes; add 75 kilograms of Virahols; then 50 kilograms of mass percentage concentration 90% plant sterols (are derived from peanut; wherein-Sitosterol 43.1%; Stigmasterol: 22.3%; campesterol: 24.1%; brassicasterol content 0.5%) 17.8 kilograms that prepare with embodiment 4 contain polyunsaturated fat acyl phospholipids phatidylcholine and add in the reactor; dissolve 0.3 kilogram of calcium chloride; the aqueous solution of 500 liters of pH5.6; under nitrogen protection; drop into 100,000 unit Phospholipase Ds; in 45 degrees centigrade; continue mechanical stirring; react and stopped in 6 hours stirring; finish reaction; standing demix is got organic phase, the normal heptane during according to reaction and the ratio of Virahol; press the relation with 1:1; re-extract residue mother liquor 2 times, the set organic extract liquid is evaporated to basic organic solvent-free under 40 degrees centigrade; add 50 liters of pure water; emulsification is filtered and is removed insolubles, adds 80 liters of acetone again; the filtered and recycled precipitation; precipitation is soaked for some time with 50 liters of acetone again, filtered and recycled and 16.7 ± 0.5 kilograms of throw outs of dry acquisition, and wherein the phosphatidyl sterol content is 48.1 ± 2.2%; in the throw out unsaturated fatty acid content after testing EPA be that 14.9 ± 1.5%%, DHA is 10.4 ± 1.3%.
Embodiment 11: preparation contains the phosphatidyl stanols of polyunsaturated fat acyl group
In 1000 liters of reactors; add in 300 kilograms of normal heptanes; add 60 kilograms of Virahols; then 60 kilograms of mass percentage concentration 50% phytostanolss (are derived from soybean; wherein-and sitostanol: 29.6%; stigmastanol: 11.3%; campestanol: 8.3%; vegetable seed stanols content 0.8%) with embodiment 3 in 10.0 kilograms of phosphatidylcholines obtaining add in the reactors; dissolve 0.5 kilogram of calcium chloride under nitrogen protection, drop into 50,000 unit Phospholipase Ds, in 50 degrees centigrade; continue mechanical stirring; react and stopped in 4 hours stirring, finish reaction, under 40 degrees centigrade, be evaporated to basic organic solvent-free; 30 liters of acetone; stir and soaked 4 hours, filtered and recycled and 14.8 ± 0.2 kilograms of throw outs of dry acquisition, wherein phosphatidyl stanols content is 38.6 ± 1.4%; in the throw out unsaturated fatty acid content after testing EPA be that 14.3 ± 1.1%%, DHA is 9.5 ± 1.2%.
The preparation of 12: two dodecahexaenes (DHA) of embodiment acyl phosphatidyl Sitosterol
In the 250ml reactor; under nitrogen protection; in 45 degrees centigrade; continue mechanical stirring; add the 200ml normal heptane; add 1g docosahexenoic acid phosphatidyl choline (PC purity: 90%, DHA content is 42.1%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 5g Sitosterol; with the 40ml Virahol; water damping fluid in the 200ml pH5.6 scope drops into 20,000 unit Phospholipase Ds, reacts to stop in 4 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 20 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.08 ± 0.09g docosahexenoic acid acyl phosphatidyl Stigmasterol ester, and wherein its DHA content is 39.8% through the GC detection, and phosphatidyl Sitosterol content is 45.6 ± 2.3%.
Embodiment 13: the preparation of eicosa-pentaenoic (EPA) acyl phosphatidyl Sitosterol
In the 250ml reactor; under nitrogen protection, in 40 degrees centigrade, continue mechanical stirring; add the 200ml normal heptane; add 1g timnodonic acid phosphatidyl choline (PC purity: 90%, DHA content is 42.1%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 3g Sitosterol; with the 60ml Virahol; the water damping fluid of 400ml pH6.0 drops into 20,000 unit Phospholipase Ds, reacts to stop in 8 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 20 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.01 ± 0.14g timnodonic acid acyl phosphatidyl Stigmasterol ester, and wherein its DHA content is 40.6% through the GC detection, and phosphatidyl Sitosterol content is 46.6 ± 2.0%.
The preparation of 14: two dodecahexaenes (DHA) of embodiment acyl phosphatidyl sitostanol
In the 250ml reactor; under nitrogen protection; in 47 degrees centigrade; continue mechanical stirring; add the 200ml normal heptane; add 1g docosahexenoic acid phosphatidyl choline (PC purity: 90%, DHA content is 42.1%); 5g sitostanol (purity is greater than 90%) dissolving adds 0.1g calcium chloride; with the 40ml Virahol; water damping fluid in the 200ml pH5.6 scope drops into 20,000 unit Phospholipase Ds, reacts to stop in 4 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 20 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.07 ± 0.22g docosahexenoic acid acyl phosphatidyl stigmastane alcohol ester, and wherein its DHA content is 39.5% through the GC detection, and phosphatidyl sitostanol content is 45.1 ± 2.0%.
Embodiment 15: the preparation of eicosa-pentaenoic (EPA) acyl phosphatidyl sitostanol
In the 250ml reactor; under nitrogen protection; in 40 degrees centigrade; continue mechanical stirring; add the 200ml normal heptane; add 1g timnodonic acid phosphatidyl choline (PC purity: 90%, DHA content is 42.1%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 3g sitostanol; with the 50ml Virahol; the water damping fluid of 400ml pH6.0 drops into 20,000 unit Phospholipase Ds, reacts to stop in 8 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 20 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.02 ± 0.12g timnodonic acid acyl phosphatidyl stigmastane alcohol ester, and wherein its DHA content is 39.7% through the GC detection, and phosphatidyl sitostanol content is 46.1 ± 1.5%.
Embodiment 16: the preparation of eicosa-pentaenoic (EPA) acyl phosphatidyl campesterol
In the 250ml reactor; under nitrogen protection; in 50 degrees centigrade; continue mechanical stirring; add the 200ml normal heptane; add 1g timnodonic acid phosphatidyl choline (PC purity: 90%, DHA content is 42.1%); (purity: dissolving 90%) adds 0.1g calcium chloride to the 10g campesterol; with the 30ml Virahol; the water damping fluid of 300ml pH6.5 drops into 20,000 unit Phospholipase Ds, reacts to stop in 6 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 20 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.05 ± 0.14g timnodonic acid acyl phosphatidyl campesterol ester, and wherein its DHA content is 41.3% through the GC detection, and phosphatidyl campesterol content is 48.1 ± 1.3%.
Embodiment 17: the preparation of eicosa-pentaenoic (EPA) acyl phosphatidyl campestanol
In the 250ml reactor; under nitrogen protection; in 45 degrees centigrade; continue mechanical stirring; add the 200ml normal heptane; add 1g timnodonic acid phosphatidyl choline (PC purity: 90%, DHA content is 42.1%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 10g campestanol; with the 70ml Virahol; the water damping fluid of 300ml pH6.5 drops into 20,000 unit Phospholipase Ds, reacts to stop in 5 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 30 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.09 ± 0.11g timnodonic acid acyl phosphatidyl campestanol ester, and wherein its DHA content is 40.5% through the GC detection, and phosphatidyl campestanol content is 46.6 ± 1.1%.
Embodiment 18: the preparation of docosapentaenoic (DPA) acyl phosphatidyl campestanol
In the 250ml reactor; under nitrogen protection; in 45 degrees centigrade; continue mechanical stirring; add the 200ml normal heptane; add 1g clupanodonic acid phosphatidyl choline (PC purity: 90%, DPA content is 40.8%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 10g campestanol; with the 70ml Virahol; the water damping fluid of 300ml pH6.5 drops into 20,000 unit Phospholipase Ds, reacts to stop in 5 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 30 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.15 ± 0.21g timnodonic acid acyl phosphatidyl campestanol ester, and wherein its DPA content is 40.3% through the GC detection, and phosphatidyl campestanol content is 44.9 ± 1.3%.
Embodiment 19: the preparation of arachidonic acid (AA) acyl phosphatidyl campestanol
In the 250ml reactor; under nitrogen protection; in 45 degrees centigrade; continue mechanical stirring; add the 200ml normal heptane; add 1g arachidonic acid (AA) phosphatidyl choline (PC purity: 90%, AA content is 44.5%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 10g campestanol; with the 70ml Virahol; the water damping fluid of 300ml pH6.5 drops into 20,000 unit Phospholipase Ds, reacts to stop in 5 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 30 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.05 ± 0.17g arachidonic acid acyl phosphatidyl campestanol ester, and wherein its AA content is 42.6% through the GC detection, and phosphatidyl campestanol content is 43.8 ± 1.1%.
Embodiment 20: the preparation of arachidonic acid (AA) acyl phosphatidyl Sitosterol
In the 250ml reactor; under nitrogen protection, in 40 degrees centigrade, continue mechanical stirring; add the 200ml normal heptane; add 1g arachidonic acid (AA) phosphatidyl choline (PC purity: 90%, AA content is 44.5%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 5g Sitosterol; with the 60ml Virahol; the water damping fluid of 400ml pH6.0 drops into 20,000 unit Phospholipase Ds, reacts to stop in 8 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 20 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.17 ± 0.14g arachidonic acid acyl phosphatidyl Stigmasterol ester, and wherein its AA content is 41.6% through the GC detection, and phosphatidyl Sitosterol content is 45.6 ± 2.0%.
Embodiment 21: the preparation of docosapentaenoic (DPA) acyl phosphatidyl Sitosterol
In the 250ml reactor; under nitrogen protection, in 40 degrees centigrade, continue mechanical stirring; add the 200ml normal heptane; add 1g clupanodonic acid phosphatidyl choline (PC purity: 90%, DPA content is 40.8%); (purity: dissolving 95%) adds 0.1g calcium chloride to the 6g Sitosterol; with the 60ml Virahol; the water damping fluid of 400ml pH6.0 drops into 20,000 unit Phospholipase Ds, reacts to stop in 8 hours stirring; finish reaction; standing demix is got organic phase, according to preceding method re-extract 2 times; the set organic extract liquid; at 20 degrees centigrade of following concentrating under reduced pressure, add emulsifying water and filter, water adds the 100ml acetone precipitation; 200ml acetone embathes precipitation; filtration drying obtains 1.01 ± 0.17g timnodonic acid acyl phosphatidyl Stigmasterol ester, and wherein its DPA content is 40.1% through the GC detection, and phosphatidyl Sitosterol content is 44.3 ± 2.0%.
Embodiment 22: a kind of edible blend oil that contains the phosphatidyl sterol of polyunsaturated fat acyl group
Take by weighing Semen Maydis oil 400g, soybean oil 250g, rapeseed oil 50g, Trisun Oil R 80 90g, Rice pollard oil 50g, peanut oil 50g, polyunsaturated fat acyl phospholipids acyl sterol 50 be to 500g, antioxidant TBHQ 0.05g, and stirring gets final product.
Embodiment 23: a kind of puffed food that contains the phosphatidyl sterol of polyunsaturated fat acyl group
Take by weighing and be rich in polyunsaturated fat acyl phospholipids acyl sterol 20-300g, salt 3g, starch 1000g; seasonings 70g; vitamin-E 0.5g is earlier with phosphatidyl sterol, salt; starch; vitamin-Es etc. are put together and are stirred evenly, put it into then in the expanded main frame expanded, typing; seasonings is put into flavoring machine, get final product after then expanded, stereotyped food being put into the flavoring machine seasoning.
Embodiment 24: a kind of liquid milk products that contains the phosphatidyl sterol of polyunsaturated fat acyl group
Take by weighing milk 992g, emulsifying agent 1g contains polyunsaturated fat acyl phospholipids acyl sterol ester 5-200g, vitamin e1 g, and Quicifal 1g, through batching, pasteurize or ultra high temperature sterilization (UHTS), sterile filling obtains milk preparation.
Embodiment 25: a kind of liquid soymilk product that contains the phosphatidyl sterol of polyunsaturated fat acyl group
Take by weighing the 1kg soybean and carry out water logging in 12 hours, grind after adding 7 times water, after bean dreg separation; after 100 ℃ of heating deodorizations; after the centrifugation, the gained liquid portion is cooled off, obtain soya-bean milk; the soya-bean milk water is modulated; make its soy bean solid content reach 10%, add therein and contain polyunsaturated fat acyl phospholipids acyl sterol ester 10-200g, vitamin-E 0.5g; Quicifal 0.5g, stirring with clarifixator gets final product.
Embodiment 26: a kind of jackfruit beverage that contains the phosphatidyl sterol of polyunsaturated fat acyl group
Take by weighing 500g water; add emulsifying agent 5g; vitamin-E 0.2g, Quicifal 0.3g is rich in how unsaturated polyenoid key fatty acyl group phosphatidyl sterol ester 10-200g; produce water external emulsion; add three potassium sorbate 1g, Xylitol 50g, jackfruit spices 1.5g; Lactobacterium acidophilum 0.2g, water supply 1000g and stir and get final product.
In this specification sheets, the present invention is described with reference to its certain embodiments.But, still can make various modifications and conversion obviously and not deviate from the spirit and scope of the present invention, the those of ordinary skill that this expertise is arranged, the technology that can teach according to this patent still, produce other embodiment within the scope of the invention, but every content that does not break away from technical solution of the present invention, all still belongs in the scope of technical solution of the present invention any simple modification, equivalent variations and modification that above embodiment does according to technical spirit of the present invention.

Claims (12)

1. phosphatidyl sterol and/or phosphatidyl stanols that contains many insatiable hungers fatty acyl group, structural formula is as follows:
Figure 35595DEST_PATH_IMAGE001
In the formula: Sn-1, Sn-2 and Sn-3 refer to 1,2 and 3 of glyceryl ester group in the phosphatide respectively; R 1And R 2A kind of in the following radicals :-C 19H 29,-C 19H 31,-C 21H 31Or-C 21H 33, X is a kind of in sterol or the stanols.
2. phosphatidyl sterol and/or the phosphatidyl stanols that contains many insatiable hungers fatty acyl group according to claim 1, it is characterized in that: sterol and/or stanols are selected from compound or the mixture of following structural formula:
Figure 15052DEST_PATH_IMAGE002
。
3. phosphatidyl sterol and/or the phosphatidyl stanols that contains many insatiable hungers fatty acyl group according to claim 2 is characterized in that: described sterol for-Sitosterol or Stigmasterol or its mixture.
4. phosphatidyl sterol and/or the phosphatidyl stanols that contains many insatiable hungers fatty acyl group according to claim 3 is characterized in that: described sterol is-Sitosterol.
5. phosphatidyl sterol and/or the phosphatidyl stanols that contains many insatiable hungers fatty acyl group according to claim 2 is characterized in that: described stanols for-sitostanol or stigmastanol or its mixture.
6. phosphatidyl sterol and/or the phosphatidyl stanols that contains many insatiable hungers fatty acyl group according to claim 5 is characterized in that: described stanols is-sitostanol.
7. one kind prepares the described method that contains phosphatidyl sterol and/or the phosphatidyl stanols of polyunsaturated fat acyl group of claim 1; it is characterized in that; may further comprise the steps: at first prepare the phosphatidylcholine that contains the polyunsaturated fat acyl group; then at water and organic solvent two-phase mixed system or contain in the organic solvent single_phase system of micro-moisture; add plant sterol or phytostanols or their mixture again, the phosphatidyl sterol and/or the phosphatidyl stanols that utilize the Phospholipase D biocatalysis to prepare into to contain the polyunsaturated fat acyl group.
8. preparation according to claim 7 contains the method for phosphatidyl sterol and/or the phosphatidyl stanols of polyunsaturated fat acyl group; it is characterized in that; water and organic solvent two-phase mixed system or contain the organic solvent single_phase system preparation of micro-moisture: the phosphatidylcholine that contains the polyunsaturated fat acyl group; also has plant sterol or/and phytostanols; dissolve in C5-C9 alkane organic solvent; and then the pure and mild or short hydrocarbon ketone of adding short hydrocarbon; add the aqueous buffer solution contain calcium salt again, thereby form water and organic solvent two-phase mixed system or contain the organic solvent single_phase system of micro-moisture.
9. preparation according to claim 8 contains the method for phosphatidyl sterol and/or the phosphatidyl stanols of polyunsaturated fat acyl group; it is characterized in that; the proportion relation of each material is as follows in described water and the organic solvent two-phase mixed system: the percent weight in volume that phosphatidylcholine adds in every liter of mixed reaction solution is 0.5%～10%; the percent weight in volume that plant sterol and/or phytostanols add in every liter of reaction solution is 1%～30%; the percent weight in volume that calcium salt adds in every liter of reaction solution is 0.001%～10%; the concentration of buffering salt then is 0～2 mol in the buffered soln; the volume percent that C5-C9 alkane organic solvent occupies in mixed reaction solution is 5% ~ 95%; short hydrocarbon alcohol or short hydrocarbon ketone possessive volume per-cent in total mixed reaction solution is 1% ~ 80%, and the pH value of the aqueous solution and organic solvent two-phase hybrid reaction system is in 4.0 ~ 8.5.
10. preparation according to claim 8 contains the method for phosphatidyl sterol and/or the phosphatidyl stanols of polyunsaturated fat acyl group, it is characterized in that described C5-C8 alkane organic solvent is optional from following compounds: the mixed solvent that any solvent in pentane, hexane, hexanaphthene, heptane, octane, nonane, decane or their isomers or these solvents form with any mixed; Described short hydrocarbon alcohol or short hydrocarbon ketone are optional from following compounds: the mixed solvent that any solvent in ethanol, propyl alcohol, butanols, amylalcohol, acetone, butanone or their isomers or these solvents form with any mixed.
11. preparation according to claim 10 contains the method for phosphatidyl sterol and/or the phosphatidyl stanols of polyunsaturated fat acyl group, it is characterized in that, described C5-C8 alkane organic solvent is normal heptane and normal hexane or their isomers; Described short hydrocarbon alcohol or short hydrocarbon ketone are propyl alcohol or acetone.
12. contain the phosphatidyl sterol of polyunsaturated fat acyl group and phosphatidyl stanols as the application in the functional food of additive cholesterol and content of triglyceride in reducing human plasma, culinary art material, the beverage.
CN2013101791424A 2013-05-15 2013-05-15 Polyunsaturated fatty acyl group-containing phosphatidyl sterol and/or phosphatidyl stanol, and preparation method and application of same Pending CN103242407A (en)

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CN105686003A (en) * 2016-01-20 2016-06-22 浙江养生堂实业发展有限公司 Composition with plant stanol ester and preparation method and application thereof
CN106665864A (en) * 2016-12-20 2017-05-17 北京双娃乳业有限公司 Fat reducing, sugar reducing and heart protecting middle-aged and aged soybean milk powder and preparation method thereof

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