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WO2007039041A1 - Composition alimentaire - Google Patents

Composition alimentaire Download PDF

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Publication number
WO2007039041A1
WO2007039041A1 PCT/EP2006/008847 EP2006008847W WO2007039041A1 WO 2007039041 A1 WO2007039041 A1 WO 2007039041A1 EP 2006008847 W EP2006008847 W EP 2006008847W WO 2007039041 A1 WO2007039041 A1 WO 2007039041A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
sterols
food
ursolic
ursolic acid
Prior art date
Application number
PCT/EP2006/008847
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 WO2007039041A1 publication Critical patent/WO2007039041A1/fr

Links

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) a composition capable of inhibiting cholesterol absorption and (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 further heart health ingredients, wherein the form and amount of said sterols and further heart health ingredients 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.
  • the invention relates to a food product comprising one or more sterols, oleanoic acid and/or ursolic acid, and 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 sterol is selected from the group of fatty acid ester of ⁇ -sitosterol , ⁇ -sitostanol , campesterol, campestanol, stigmasterol , stigmastanol and mixtures thereof.
  • compositions of the invention are food products.
  • composition of the invention comprises both oleanoic acid and ursolic acid.
  • oleanolic acid or ursolic acid also encompasses the food grade or edible salts or derivatives of these components, wherein the heart health functionality is substantially the same as for oleanolic acid and/or ursolic acid.
  • 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. Also although 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.
  • compositions of the invention comprise sterols and oleanolic acid and/or ursolic acid.
  • the amounts should be chosen such that the weight ratio of sterols to the total amount of oleanolic acid and ursolic acid is from 1 : 10 to 50 : 1, more preferred from 5 : 1 to 50 : 1, most preferred from 10 : 1 to 30 : 1.
  • Ursolic acid and oleanolic acid are known for their health effects.
  • EPl, 161, 879 describes the use of oleanolic acid and ursolic acid, obtained from apple skins, in food products and food supplements.
  • Ursolic acid and oleanolic acid can be obtained by various methods, for example by synthesis or by extraction from various natural sources such as apples, pears, cranberries, cherries, prunes or hawthorn.
  • a preferred natural extract containing OA and/or UA 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 natural extracts containing ursolic acid and/or oleanolic acid to be used in the composition of the invention will depend on a number of factors.
  • the amount of sterol in the composition and the amount of UA and OA in the extract provided the specific weight ratio of sterols to the total of UA and OA is within the range as specified above.
  • the amount of natural extract containing ursolic acid and/or oleanolic acid will be from 0.01 to 20 wt% of the composition, more general from 0.1 to 10 wt% such as for example 1 to 5 wt%.
  • the total amount of UA and/or OA in a composition of the invention is generally from 3 to 6000 mg per kg, preferably from 30 to 1000 mg per kg, most preferred from 200 to 600 mg per kg .
  • the daily intake of total OA and/or UA is from lOmg to 800mg, more preferably from 50 to 400mg, especially from lOOmg to 200mg per day.
  • the weight ratio of UA to OA in compositions of the invention is 20 : 1 to 1 : 1, more prefered 15 : 1 to 2 : 1, and most preferred 10 : 1 to 3 : 1.
  • 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 product of the invention is preferably from 0.1% 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 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 they 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 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 C 2 - 22 fatty acids.
  • the term C 2 - 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 - 22 fatty acids are linear molecules comprising one or two acid group (s) as end group (s) .
  • Most preferred are linear C 8 - 22 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.
  • a naturally occurring fat or oil as a source of the fatty acid and to carry out the esterification via an interesterification reaction.
  • Use of a natural source nearly always results in a mixture of fatty acids.
  • 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.
  • a further object of the invention to provide a food composition having one or more health effects in humans, in particular such health effect is related to a decreased risk of cardiovascular disorders.
  • Another object is to provide such food composition having a acceptable taste, preferably a good taste.
  • Still a further object is to provide a food composition, that upon consumption 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 invention also relates to a food composition
  • a food composition comprising sterols and oleanolic acid and/or ursolic acid wherein the weight ratio of sterols to the total of oleanolic acid and ursolic acid is preferably from 5 : 1 to 50 : 1, more preferred from 10 : 1 to 30 : 1, most preferred from 25 : 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 oleanolic acid and/or ursolic acid, such as flavour, sugar, fruits, minerals, vitamins, stabilisers, thickeners, etc. in appropriate amounts.
  • the food products are fruit juice products, dairy type such as yogurt or milk products, frozen confectionery products, nutrition bars and food emulsions such as spreads. These preferred types of food products are described in some detail below. 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 ursolic acid and/or oleanolic acid 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 of dairy products according to the invention are milk, dairy spreads, cream cheese, milk type drinks and yoghurt, wherein the the sterols and ursolic acid and/or oleanolic acid 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. Typically 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.
  • level of solids in the frozen confection e.g. sugar, fat, flavouring etc
  • 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 5 wt% ursolic acid and/or oleanolic acid, 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. to an overrun of 20 to 400 %, more specific 40 to 200 % and frozen to a temperature of from -2 to -200 0 C, more specific -10 to -30 0 C. Ice cream normally comprises calcium at a level of about 0.1 wt%.
  • the average serving size of a frozen confectionery product is 85g.
  • Nutrition bars As example a composition of a granola bar is given.
  • 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
  • sterol and ursolic acid and/or oleanolic acid 0.1 to 5 wt% of sterol and ursolic acid and/or oleanolic acid.
  • 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 (O/W) emulsions and water in oil emulsions (W/O) 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 ursolic acid and/or oleanolic acid and the sterols as an ingredient in suitable amounts.
  • Examples of such food products are baked goods, dairy type foods, snacks, etc.
  • the experimental diets were semi -purified diets modified from AIN- 93 rodent diet.
  • the four diets were: A) Control diet B) OA/UA diet
  • OA and UA were isolated from hawthorn fruits.
  • 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.
  • TC total cholesterol
  • TAG triacylglycerol
  • VLDL d ⁇ 1.006 kg/L
  • LDL 1.006 ⁇ d ⁇ 1.055 kg/L
  • HDL 1.055 ⁇ d ⁇ 1.21 kg/L
  • TC and TAG concentrations in the fractions were determined using enzymatic assays .
  • VLDL and LDL fractions are low in hamsters, we combined the VLDL and LDL as non-HDL-C.
  • Data in parenthesis represent percentage difference compared to control group .

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Botany (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Medical Informatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

L'invention porte sur un produit alimentaire comprenant un ou plusieurs stérols, de l'acide oléanolique et/ou de l'acide ursolique, et 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 le stérol est sélectionné dans le groupe constitué d'ester d'acide gras de β-sitostérol, β-sitostanol, campestérol, campestanol, stigmastérol, stigmastanol et de leurs mélanges.
PCT/EP2006/008847 2005-09-30 2006-09-08 Composition alimentaire WO2007039041A1 (fr)

Applications Claiming Priority (4)

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

Publications (1)

Publication Number Publication Date
WO2007039041A1 true WO2007039041A1 (fr) 2007-04-12

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PCT/EP2006/008847 WO2007039041A1 (fr) 2005-09-30 2006-09-08 Composition alimentaire

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Families Citing this family (14)

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Publication number Priority date Publication date Assignee Title
RU2377781C2 (ru) 2003-07-17 2010-01-10 Юнилевер Н.В. Способ приготовления пищевой дисперсии, содержащей масло и структурирующий агент
EP1858341A1 (fr) 2005-02-17 2007-11-28 Unilever N.V. Procede de preparation d'une dispersion a tartiner comprenant du sterol
WO2010069746A1 (fr) 2008-12-19 2010-06-24 Unilever Nv Poudres grasses comestibles
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
EA024216B1 (ru) 2010-06-22 2016-08-31 Юнилевер Н.В. Порошкообразные пищевые жиры
PL2651234T3 (pl) 2010-12-17 2015-06-30 Unilever Bcs Europe Bv Sposób kompaktowania mikroporowatego tłuszczowego proszku oraz tak otrzymany skompaktowany tłuszczowy proszek
CA2820360C (fr) 2010-12-17 2018-10-30 Unilever Plc Emulsion d'eau dans l'huile comestible
FI123374B (fi) 2011-03-25 2013-03-15 Ravintoraisio Oy Uusi syötävä koostumus
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
WO2013117008A1 (fr) * 2012-02-10 2013-08-15 Nestec S.A. Composition renfermant de l'aubépine et des phytostérols
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
WO2014015462A1 (fr) * 2012-07-23 2014-01-30 Nestec S.A. Aubépine et phytostérols et leurs effets sur les troubles métaboliques
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
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

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EP1249180A2 (fr) * 2001-03-26 2002-10-16 Unilever N.V. Systèmes particulaires structurés

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EP1249180A2 (fr) * 2001-03-26 2002-10-16 Unilever N.V. Systèmes particulaires structurés

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Title
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