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WO2007039040A1 - Composition alimentaire - Google Patents

Composition alimentaire Download PDF

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Publication number
WO2007039040A1
WO2007039040A1 PCT/EP2006/008846 EP2006008846W WO2007039040A1 WO 2007039040 A1 WO2007039040 A1 WO 2007039040A1 EP 2006008846 W EP2006008846 W EP 2006008846W WO 2007039040 A1 WO2007039040 A1 WO 2007039040A1
Authority
WO
WIPO (PCT)
Prior art keywords
hawthorn
sterols
extract
cholesterol
acid
Prior art date
Application number
PCT/EP2006/008846
Other languages
English (en)
Inventor
Yuguang Lin
Mario A Vermeer
Original Assignee
Unilever N.V.
Unilever Plc
Hindustan Unilever Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever N.V., Unilever Plc, Hindustan Unilever Limited filed Critical Unilever N.V.
Publication of WO2007039040A1 publication Critical patent/WO2007039040A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A23G9/42—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds containing plants or parts thereof, e.g. fruits, seeds, extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof containing fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A61K36/734—Crataegus (hawthorn)
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the invention relates to a composition, specifically to a functional food composition having one or more health effects in humans.
  • a health effect is related to a decreased risk of cardiovascular disorders.
  • Plant sterols and their analogues and derivatives enjoy a considerable scientific interest for their health promoting properties.
  • sterols and fatty esters thereof are known for their LDL cholesterol lowering properties, LDL cholesterol being an established risk factor for atherosclerotic vascular diseases.
  • the maximal cholesterol lowering effect of plant sterols/stanols is about 10-15%.
  • US 2002/0068095 discloses the combination of (a) one or more phytosterols or phytostanols with (b) (b) a composition capable of inhibiting cholesterol absorption and (c) (c) a composition capable of increasing cholesterol metabolism, wherein at least one of the compositions (b) and (c) is derived from plants.
  • compositions comprising a combination of sterols and a specific plant derived material, wherein the source, form and amount of said sterols and plant materials are such that improved effects can be obtained in lowering cholesterol levels.
  • the composition of the invention can suitably be used in a variety of products, especially food products as described herein.
  • the present invention provides food compositions comprising combinations of active ingredients to reduce the risk of cardiovascular diseases beyond what is obtainable by using only one of the active ingredients.
  • sterols are combined with active materials from hawthorn in compositions comprising these ingredients in specific weight ratios, this leads to unexpectedly good lowering of plasma lipid concentrations in mammals .
  • a food product comprising (a) one or more sterols selected from the group of fatty acid ester of ⁇ -sitosterol, ⁇ -sitostanol, campesterol, campestanol, stigmasterol, stigmastanol and mixtures thereof ; and (b) an extract from hawthorn (c) wherein the weight ratio of sterols to the total amount of oleanolic acid and ursolic acid is from 1 : 10 to 50 : 1 and wherein the amount of sterols is from 0.1 to 20 wt%.
  • KR 2004 027 829 discloses nanoliposome compositions suitable for treating skin diseases. These compositions comprise a combination of pentacyclic triterpenic acid (selected from ursolic acid, ursolic acid derivates and ursolic isomers) and sterols (selected from cholesterol, cholesterol acetate, cholesterol isostearate and cholesteryl macadamiate) . Dl does not disclose food products or the use of specific fatty acid esterified steols as described above.
  • US 2002/0068095 discloses a composition comprising one or more phytosterols or phytostanols .
  • D2 does not disclose the specific esterified sterols of the current invention.
  • D2 mentions several possible plants as a suitable ingredient for the composition, the specific combination of hawthorn extract and sterols in the ratios as currently claimed do not seem to be suggested or disclosed.
  • US 5,665,359 discloses the administration of the use of Shanzha fruit to obtain a hypocholesterolemic effect .
  • D3 does not seem to disclose the combined use of hawthorn extract and specific esterified sterols in specific ratios in accordance to the present invention.
  • the hawthorn extract is The hawthorn extract
  • hawthorn refers to the plan of Crateaegus species or its fruits. There are more than 250 species of hawthorn all over the world, consisting of small trees and scrubs.
  • hawthorn refers to the Crataegus Oxyacantha especially to the Chinese variant of hawthorn, Crataegus pinnatifada.
  • hawthorn extract refers to extracts of hawthorn or parts thereof, in particular extracts of the fruits of hawthorn.
  • hawthorn extract refers both to extracts of hawthorn still comprising one or more solvents or concentrated or dried or powdered versions thereof.
  • hawthorn in itself or hawthorn juice are less suitable, since in hawthorn or its juice the concentration of active ingredients is relatively low.
  • Preferred hawthorn extracts can be obtained by using organic solvents, for example dichloromethane (DCM) , ethylacetate, acetone, ethanol or heptane. Particularly preferred is the use of edible organic solvents. Particularly preferred is the use of ethanol .
  • the extract can for example be obtained by contacting dried hawthorn berries with the solvent e.g for a period of 1 to 24 at ambient temperature (Soxhlett extraction) . After extraction, the solvent may be partially or fully removed e.g to obtain a concentrated extract or a dried, e.g powdered or syrup hawthorn extract .
  • hawthorn comprises ursolic acid (UA) and oleanolic acid (OA) .
  • hawthorn extracts comprises bioflavonoids.
  • hawthorn examples include oligomeric procyanidins and flavans such as catechins and epicatechin, triterpene derivatives such as OA and UA and phenolics such as chlorogenic acid and caffeic acid.
  • oligomeric procyanidins and flavans such as catechins and epicatechin
  • triterpene derivatives such as OA and UA
  • phenolics such as chlorogenic acid and caffeic acid.
  • UA and OA are sufficiently soluble in organic solvents, especially ethanol and for this reason applicants believe that the presence of UA and OA in the extract can be seen as a marker for the presence of possible yet unidentified beneficial ingredients in the extract .
  • Dried hawthorn fruit typically comprises about 3 g/kg of UA and OA. Also typically the weight ratio of OA to UA in dried hawthorn fruit is about 1 : 6.
  • Compositions of the invention comprise sterols and a hawthorn extract. The amount and concentration of the extract should be chosen such that the weight ratio of sterols to the total of Oleanolic acid and Ursolic acid is from 1 : 10 to 50 : 1, more preferred from 5 : 1 to 30 : 1, most preferred from 10 : 1 to 20 : 1.
  • a preferred extract of Hawthorn comprises at least 10 wt% of materials extracted from hawthorn and up to 90 wt% of solvent.
  • the amount of materials from hawthorn is at least 25 wt%, more preferred 50 wt%, while the solvent level in the extract preferably is from 0 to 50 wt%, for example from 10 to 40 wt%.
  • hawthorn extracts which are substantially free from solvent most preferably are hawthorn extracts which after extraction have been dried to form a hawthorn extract in powder form.
  • the amount of extract to be used in the composition of the invention will depend on a number of factors. Depending on for example the amount of sterol in the composition and the amount of UA and OA in the extract, the amount of hawthorn extract in food compositions or of the invention may vary in a broad range provided the specific weight ratio of sterols to the total of UA and OA is obtained which is within the range as specified above. Generally however the amount of hawthorn extract will be from 0.01 to 20 wt% of the food composition, more general from 0.1 to 10 wt% such as for example 1 to 5 wt%.
  • the hawthorn extract comprises ethanol as the solvent
  • the amount of extract in the food composition is such that the level of ethanol in the food is less than 0.05 wt%, more preferred less than 0.03 wt% such as from 0.003 to 0.03 wt%. This lowering of the amount of ethanol without unduly affecting the beneficial properties of the extract may for example be achieved by using concentrated versions or powdered versions of the extract.
  • sterols refers to phytosterols, phytostanols, analogues, esters and derivatives thereof.
  • sterol esters also refers to fatty acid esters of phytosterols or phytostanols
  • the phytosterols, phytostanols and their analogues and derivatives may be selected from one or more of phytosterols, phytostanols, synthetic analogues of phytosterols and phytostanols and esterified derivatives of any of the foregoing, and mixtures of any of these.
  • the total amount of such substances in a food product of the inveniton is preferably from 0.01% to 20%, more preferably from 0.1% to 15%, still more preferably from 0.2% to 8%, and most preferably from 0.3% to 8% by weight of the food product composition.
  • the daily intake of such sterol-type component of the combination is from 0. Ig to 3g, more preferably from 1.5g to 2.5g, especially from 2g to 2.25g per day.
  • Sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 4 , 4 ' -dimethylsterols .
  • oils mainly exists as free sterols and sterol esters of fatty acids although sterol glucosides and acylated sterol glucosides are also present.
  • There are three major phytosterols namely beta-sitosterol , stigmasterol and campesterol .
  • the phytostanols are the respective 5 ⁇ - saturated derivatives of phytosterols such as sitostanol, campestanol and their derivatives . Synthetic analogues of any of the sterols or stanols (which include chemically modified natural components) may also be used.
  • the sterol is selected from the group comprising fatty acid ester of ⁇ -sitosterol , ⁇ -sitostanol , campesterol, campestanol, stigmasterol , stigmastanol and mixtures thereof.
  • the sterol materials recited above may optionally be provided in the form of one or more fatty acid esters thereof. Mixtures of esterified and non-esterified materials may also be used.
  • any of the sterols and their synthetic analogues used in the present invention are preferably esterified with a fatty acid.
  • they are esterified with one or more C2-22 fatty acids.
  • the term C2-22 fatty acid refers to any molecule comprising a C2-2 2 main chain and at least one acid group.
  • the C 2 - 22 main chain may contain 1-6 double bonds, be partially substituted or side chains may be present.
  • the C 2 - 2 2 fatty acids are linear molecules comprising one or two acid group (s) as end group (s) .
  • Most preferred are linear C 8 -2 2 fatty acids as occur in natural liquid oils.
  • Suitable examples of any such fatty acids are for example lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid and mixtures thereof.
  • a mixture of fatty acids may be used for esterification of the sterols.
  • the fatty acid mixture contains a high amount (>50%, preferably >70%, further preferred >80%) of unsaturates, being either monounsaturated fatty acids (MUFA) and/or polyunsaturated fatty acids (PUFA) .
  • MUFA monounsaturated fatty acids
  • PUFA polyunsaturated fatty acids
  • fatty acid mixtures of sunflower, safflower, rapeseed, linseed, olive oil, linola and/or soybean are used. These are typical sources of high PUFA and/or low SAFA.
  • Suitable esterification conditions are for example described in WO 92/19640.
  • the invention also relates to a food composition
  • a food composition comprising sterols and hawthorn extract wherein the weight ratio of sterols to the total of Oleanolic acid and Ursolic acid is from 1 : 10 to 50 : 1, more preferred from 5 : 1 to 30 : 1, most preferred from 10 : 1 to 20 : 1.
  • the food composition according to the invention may preferably be used as a physiologically functional food product.
  • the consumption of the food composition by a human subject is effective in causing in the human subject a reduction of level of total blood cholesterol and/or a reduction of level of LDL cholesterol .
  • the food products according to the invention may be of any food type. They may comprise common food ingredients in addition to the sterol and the hawthorn extract, such as flavour, sugar, fruits, minerals, vitamins, stabilisers, thickeners, etc. in appropriate amounts.
  • the food products are fruit juice products, dairy type products or frozen confectionery products. These preferred types of food products are described in some detail below and in the examples. These preferred food products may advantageously be used as part of a fat containing meal, or be used in conjuction with such a meal.
  • Examples of food products according to the invention are:
  • fruit juice products according to the invention are juices derived from citrus fruit like orange and grapefruit, tropical fruits, banana, peach, peer, strawberry or berry in which the sterols and the hawthorn extract extract are dissolved or suspended optionally in the presence of an appropriate emulsifier
  • the average serving size for the fruit juice products is 250 ml.
  • the amount of sterol in 250 ml juice will be from 0.2 to 2 grams.
  • dairy type products examples are milk, dairy spreads, cream cheese, milk type drinks and yoghurt, wherein the the sterols and hawthorn extract extract are dissolved or suspended optionally in the presence of an appropriate emulsifier.
  • flavour or other additives may be added, also optionally the product could be homogenized by a high speed mixer.
  • the average serving size for the dairy type product is 100 ml.
  • the amount of sterol in 100 ml dairy product will be from 0.2 to 2 grams.
  • An average serving size for a yoghurt type product could be from 50 to 250 g, generally from 80 to 200 g. Typically the amount of sterol in such a serving will be from 0.2 to 2 grams.
  • frozen confectionery product includes milk containing frozen confections such as icecream, frozen yoghurt, sherbet, sorbet, ice milk and frozen custard, water-ices, granitas and frozen fruit purees.
  • the level of solids in the frozen confection e.g. sugar, fat, flavouring etc
  • the level of solids in the frozen confection is more than 3 wt.%, more preferred from 10 to 70 wt.%, for example 40 to 70 wt.%.
  • Ice cream will typically comprise 0 to 20 wt . % of fat, 0.1 to 5 wt.%sterols, 0.1 to 5wt . % hawthorn extract, sweeteners, 0 to 10 wt. % of non-fat milk components and optional components such as emulsifiers, stabilisers, preservatives, flavouring ingredients, vitamins, minerals, etc, the balance being water.
  • ice cream will be aerated e.g.
  • Ice cream normally comprises calcium at a level of about 0.1 wt%.
  • the average serving size of a frozen confectionery product is 85g.
  • Granola bars consists of a binder syrup which binds the granola and fruit ingredients into a solid bar.
  • E.g. nuts, pieces of chocolate, or a low moisture yoghurt filling can be added as well.
  • the bar can be enrobed with a coating of e.g. chocolate or a low moisture yoghurt layer.
  • Granola bar example (weight per cent)
  • granola base oat flakes, wheat flakes, rice crispies
  • binder syrup corn syrup, sugar, salt, lecithine, vegetable oil
  • Moisture content of a nutrition bar is typically below 15%.
  • the food product may be an oil and water containing emulsion, for instance a spread or a margarine.
  • Oil and water emulsion is herein defined as an emulsion comprising oil and water and includes oil in water (0/W) emulsions and water in oil emulsions (W/0) and more complex emulsions for instance water- in-oil-in-water (W/O/W/O/W) emulsions.
  • Oil is herein defined as including fat .
  • the food product is a spread, frozen confection, a drink or a sauce.
  • a spread according to the invention comprises 30-90 wt . % vegetable oil.
  • a spread has a pH of 4.2-6.0.
  • Other food product according to the invention can be prepared by the skilled person based on common general knowledge, using the hawthorn extract the sterols as an ingredient in suitable amounts.
  • Examples of such food products are baked goods, dairy type foods, snacks, etc.
  • Figure 1 Plasma cholesterol -lowering effect of hawthorn extract, sterols (PSE) as well as recipe of these two ingredients.
  • FIG. 2 Liver free cholesterol (CH) and cholesterol ester concentrations of hamsters fed different diets as indicated. Data are presented as mean ⁇ SE. No statistical difference was observed among groups with regard to CH concentrations. * indicates P ⁇ 0.01 compared to control.
  • Example IA preparation of hawthorn extract in ethanol
  • Non-heated dried sliced hawthorn berries were obtained.
  • the hawthorn berries were milled in a cooled milling machine.
  • 425 grams of the powdered hawthorn berries were extracted by the Soxhlett method with 2X liters of ethanol. The extraction was executed for approximately 12 hours (40 minutes per Soxhlett cycle) .
  • the total ethanol extract was dried by using a RotaVap.
  • the yield of the extraction was 167 grams (39%) of hawthorn extract .
  • Example IB preparation of hawthorn extract in different solvents Extractions as in example IA with 5 different solvents at room temperature provided the following results: solvent OA UA OA UA
  • Heptane 1.2% 1. 7% 0.00% 0.00% ursolic acid and oleanolic acid were analysed by Ci 8 -HPLC or GC- TOF. Comparable results were obtained by both methods.
  • Ethanol is the extraction solvent providing the highest yield but with a low purity for oleanolic and ursolic acid.
  • DiChloroMethane and EthylAcetate provide higher purities but with a lower yield.
  • the impurities in the ethanol extract will be mainly sugars originating from the hawthorn fruit.
  • mice Male LVG Golden Syrian hamsters (aged 8 weeks, approximately 70-80 g of body weight at arrival) were acclimated to individual stainless steel cages and fed a basal semi purified diet (4) before initiation of the experimental diet treatment. These animals were randomly assigned to five diet groups (denoted A to E) based on their body weight. Each group consisted of 20 hamsters. Animals were housed individually in cages in a temperature-controlled environment under a 12 h light-dark cycle (lights on 18:00 h) . The experimental diets were semi purified diets modified from AIN-93 rodent diet. The four diets were:
  • the details of the nutrient composition of each diet are shown in Table 1.
  • the diets contained 30 energy % as fat (15.6 en% SAFA, 8,9 en% MUFA and 4,8 en% PUFA, resembling to a typical Western fat intake) .
  • PSE was ⁇ -sitosterol which had been esterified with fatty acids from sunflower oil to an esterification degree of >92%.
  • Animals were fed experimental diets for 4 weeks. Hamsters had free access to food and water.
  • hamsters were deprived for food overnight (approximately 16 hours) .
  • Blood samples were drawn into EDTA-wetted syringes by aorta puncture under halothane narcosis. The animals then were killed by decapitation, and liver samples were collected. Plasma was collected after centrifugation at 1500 x g at room temperature for 10 min.
  • Liver sample collection The bile in the gallbladder was collected through puncture, and then the gallbladder was excised. The complete liver was excised and weighed. About 1 g of liver was sampled and frozen at -20 0 C for hepatic lipid analysis .
  • Hepatic cholesterolmeasurement A 300-mg portion of liver was homogenised. Lipids in liver samples were extracted with dichloromethane (DCM) . TC and free cholesterol (FC) were determined as described above. The concentration of cholesterol esters (CE) was calculated as the difference between TC and FC.
  • DCM dichloromethane
  • FC free cholesterol
  • Plasma cholesterol lowering effect ( Figure 1) Hamsters administered hawthorn extract, PSE or hawthorn extract + PSE had significantly lower plasma non-HDL cholesterol (i.e. VLDL+LDL) concentration than the control group (P ⁇ 0.05). Only hawthorn extract + PSE diet lowered plasma total cholesterol compared to control diet (P ⁇ 0.05) . In addition, the combination of hawthorn extract and sterols has stronger plasma TAG lowering effect compared to control, hawthorn extract or sterol treatments individually. These data demonstrate that the combination of hawthorn extract and sterols has synergistic plasma cholesterol- and TAG-lowering effects.
  • Hepatic cholesterol lowering effect (Figure 2) : The hawthorn extract alone has no hepatic cholesterol lowering effect, while the combination of hawthorn extract and sterols has extra hepatic cholesterol (ester) lowering effect compared to sterol treatment alone. These data further indicate that the combination of these two ingredients has synergistic cholesterol lowering effect.

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Abstract

L'invention porte sur un produit alimentaire comprenant (a) un ou plusieurs stérols sélectionnés dans groupe constitué d'ester d'acide gras de de β-sitostérol, β-sitostanol, campestérol, campestanol, stigmastérol, stigmastanol et de leurs mélanges; et (b) d'un extrait d'aubépine, (c) dans lequel le rapport pondéral entre les stérols et la quantité totale d'acide oléanolique et d'acide ursolique est de 1: 10 et de 50: 1 et dans lequel la quantité de stérols est de 0.1 à 20 % en poids.
PCT/EP2006/008846 2005-09-30 2006-09-08 Composition alimentaire WO2007039040A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP05077229 2005-09-30
EP05077229.2 2005-09-30
EP06075657 2006-03-21
EP06075657.4 2006-03-21

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CN101475929B (zh) * 2009-01-19 2011-03-30 詹亚光 一种利用白桦悬浮培养生产齐墩果酸的方法
ITGE20110041A1 (it) * 2011-04-12 2012-10-13 Ct Di Sperimentazione Ed Assist Enza Agricola Metodo di ottenimento di acido carnosico e triterpeni, come composti puri o come fitocomplessi arricchiti, da piante della famiglia delle lamiaceae
WO2013117732A1 (fr) * 2012-02-10 2013-08-15 Nestec S.A. Aubépine et phytostérols et leurs effets sur les maladies cardiovasculaires
WO2014015462A1 (fr) * 2012-07-23 2014-01-30 Nestec S.A. Aubépine et phytostérols et leurs effets sur les troubles métaboliques
CN104105497A (zh) * 2012-02-10 2014-10-15 雀巢产品技术援助有限公司 山楂和植物甾醇及它们对心血管疾病的作用
US8865245B2 (en) 2008-12-19 2014-10-21 Conopco, Inc. Edible fat powders
US8927045B2 (en) 2005-02-17 2015-01-06 Sandra Petronella Barendse Process for the preparation of a spreadable dispersion
US8940355B2 (en) 2003-07-17 2015-01-27 Conopco, Inc. Process for the preparation of an edible dispersion comprising oil and structuring agent
CN104411319A (zh) * 2012-07-23 2015-03-11 雀巢产品技术援助有限公司 山楂和植物甾醇类及其对代谢性疾病的作用
US8993035B2 (en) 2010-12-17 2015-03-31 Conopco, Inc. Edible water in oil emulsion
EP2688427B1 (fr) 2011-03-25 2015-07-29 Raisio Nutrition Ltd. Boisson a effet reducteur du cholesterol sanguin
CN105473005A (zh) * 2013-08-14 2016-04-06 雀巢产品技术援助有限公司 包含山楂和植物甾醇的乳制品组合物
US9924730B2 (en) 2010-06-22 2018-03-27 Unilever Bcs Us, Inc. Edible fat powders
US10219523B2 (en) 2010-12-17 2019-03-05 Upfield Us Inc. Process of compacting a microporous fat powder and compacted fat powder so obtained

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