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WO2000061694A1 - Procede de fabrication d'ester de phytosterol ou du phytostanol liposoluble d'un acide gras insature - Google Patents

Procede de fabrication d'ester de phytosterol ou du phytostanol liposoluble d'un acide gras insature Download PDF

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Publication number
WO2000061694A1
WO2000061694A1 PCT/KR1999/000569 KR9900569W WO0061694A1 WO 2000061694 A1 WO2000061694 A1 WO 2000061694A1 KR 9900569 W KR9900569 W KR 9900569W WO 0061694 A1 WO0061694 A1 WO 0061694A1
Authority
WO
WIPO (PCT)
Prior art keywords
phytosterol
fatty acid
unsaturated fatty
phytostanol
oil
Prior art date
Application number
PCT/KR1999/000569
Other languages
English (en)
Inventor
Dae-Won Chung
Seung-Kwon Noh
Kab-Sig Kim
Original Assignee
Eugene Science, Inc.
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 Eugene Science, Inc. filed Critical Eugene Science, Inc.
Priority to AU57634/99A priority Critical patent/AU5763499A/en
Publication of WO2000061694A1 publication Critical patent/WO2000061694A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
    • 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 OR TREATMENT THEREOF
    • A23C15/00—Butter; Butter preparations; Making thereof
    • A23C15/12—Butter preparations
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/013—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or 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 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

Definitions

  • the present invention relates to a method for manufacturing fat-soluble phytosterol or phytostanol ester of unsaturated fatty acid for inhibiting the absorption of cholesterol and foodstuffs containing the same.
  • phytosterol which is a kind of plant sterol, lowers serum cholesterol level by reducing the absorption of cholesterol in the intestines through competition with LDL-cholesterol.
  • FDA approved phytosterol as a food additive not affecting the biosynthesis of cholesterol and not having any side- effects mentioned above.
  • Phytosterol means all the alcohol compounds with steroid moiety found in higher plant and covers stigmasterol, spinasterol, campesterol and sitosterol.
  • Sitosterol has ⁇ , ⁇ , ⁇ - type.
  • the cholesterol lowering effect of ⁇ -sitosterol 24-ethyl-
  • ⁇ -sitosterol is known to be the principal component of Zea mays L. which is used for treatment of gingivitis and alveolitis. However, it has a critical demerit preventing it from wide use, i.e., its insolubility against oil and water. This hydrophobic and lipophobic properties only allow them to be formulated as tablet or capsule, while making it difficult and inefficient as food ingredient.
  • ⁇ - sitostanol 24-ethyl-5 ⁇ -cholestane-3 ⁇ -ol
  • edible oil to generate ⁇ -sitostanol ester, which was proven to be effective in lowering serum cholesterol when used as an additive for the solid oil product such as margarine (see: WO 92/19640).
  • the product obtained in the above process is the mixture of ⁇ -sitostanol esters of saturated and unsaturated fatty acids, since edible oil such as rapeseed oil were used.
  • the composition of the products is dependent on the array of fatty acids present in the edible oil used in the reaction.
  • the profile of saturated and unsaturated fatty acids is important in cholesterol lowering effect because saturated fatty acids are known to depress LDL(low density lipoprotein) receptors and decrease clearance of LDL cholesterol from plasma ⁇ ___: Hayes, K. C. et al., Prostaglandins . Leukot Essen t Fa tty Acids . , 57 (4-5) : 411-418, 1997).
  • the hydrogenation of ⁇ -sitosterol is required to obtain ⁇ - sitostanol itself.
  • ⁇ -sitosteryl oleate can be obtained by the reaction of ⁇ -sitosterol and the activated forms of oleic acid, such as oleyl chloride (.ge_e_: Hartman, L. Chem . Rev. , 58:845-864, 1958) or oleic anhydride ⁇ __s: Mattson, F. H. et al., J. Lipid Res . , 5:374-377, 1964).
  • oleyl chloride .ge_e_: Hartman, L. Chem . Rev. , 58:845-864, 1958
  • oleic anhydride ⁇ __s Mattson, F. H. et al., J. Lipid Res . , 5:374-377, 1964.
  • these processes are not suitable for the production of food grades as well as for the commercial scale reaction since the activated forms are very unstable and toxic chemicals are necessary for the preparation of activated forms.
  • ⁇ -sitosteryl oleate Another possible process for preparing ⁇ -sitosteryl oleate is the modification of the transesterification reaction of ⁇ -sitostanol and edible oil, which was carried out at 90-120 ° C using strong basic catalyst, as described in WO 92/19640.
  • this process is also undesirable for the preparation of ⁇ -sitosteryl oleate because unsaturated fatty acids (e.g., oleic acid) are unstable and readily oxidized at high temperature.
  • the present inventors have made an effort to manufacture fat-soluble phytosterol or phytostanol derivatives which provide cholesterol lowering effect, while focusing on the role of phytosterol which inhibits the absorption of cholesterol in intestine.
  • phytosterol has a critical demerit of insolubility against oil and water. This hydrophobic and lipophobic properties make it difficult and inefficient to be applied for various formulation.
  • the inventors synthesized lipophilic derivatives under the mild reaction conditions by the esterification of phytosterol or phytostanol with unsaturated fatty acid.
  • the lipophilic derivatives of phytosterol or phytostanol are soluble in liquid oils such as corn oil and provide a cholesterol lowering effect.
  • a primary object of the present invention is, therefore, to provide a method for manufacturing fat- soluble phytosterol or phytostanol esters of unsaturated fatty acid under the mild reaction conditions.
  • the other object of the invention is to provide foodstuffs containing the fat-soluble phytosterol or phytostanol ester of unsaturated fatty acid.
  • the method for manufacturing fat-soluble phytosterol or phytostanol ester of unsaturated fatty acid of present invention comprises the steps of: esterification of phytosterol or phytostanol with unsaturated fatty acid by dissolving them in a nonpolar organic solvent with a basic catalyst and adding a carboxyl group activating agent dissolved in a nonpolar organic solvent; and, precipitation of the esterified product in methanol or a mixture of methanol and acetone, after filtering the esterified product and evaporating the nonpolar solvent under a reduced pressure.
  • the final product can be obtained in a wax form by solidifying at -2 ° C, discarding the remaining solvent, and drying the product under a reduced pressure.
  • toluene, methylene chloride, dichloroethane, tetrahydrofuran, benzene or diethylether is employed as the nonpolan organic solvent, and 4-dimethylaminopyridine, pyridine or triethylamine as the basic catalyst, 1,3- dicyclohexylcarbodiimide (DCC) , l-ethyl-3- [3' - dimethylaminopropyl] -carbodiimide, oxalyl chloride, carbonyl diimidazole, 2-chloropyridium, 2, 2' -dipyridyl disulfide or 2-imidazoyl disulfide, as the carboxyl group activating agent.
  • DCC 1,3- dicyclohexylcarbodiimide
  • l-ethyl-3- [3' - dimethylaminopropyl] -carbodiimide oxalyl chloride, carbonyl diimid
  • Used phytosterol is known as an alcohol compound with steroid moiety discovered in higher plant, which covers stigmasterol, spinasterol, campesterol and sitosterol, preferably sitosterol including ⁇ , ⁇ , ⁇ -type; phytostanol includes sitostanol, campestanol which is hardened form of that; and, unsaturated fatty acid to be used has between 4 and 22 carbon atoms, preferably from 12 to 20, more preferably from 16 to 18 and has degree of unsaturation of 1 to 3.
  • the present invention also provides foodstuffs containing the phytosterol or phytostanol ester of fatty acid which is soluble in liquid oil.
  • Step 1 Esterification of phytosterol or phytostanol with unsaturated fatty acid
  • ⁇ -sitosterol and oleic acid are dissolved in a nonpolar organic solvent in a molar ratio of 1:1 to 1:3, preferably 1:2.
  • a basic catalyst is subsequently added, and all particles are mixed completely under the refluxed temperature.
  • a carboxyl group activating agent dissolved in organic solvent is added in a drop-wise for 10 min to 90 min, preferably 30 min to 60 min, most preferably 40 min in a molar ratio of 1:1.1 to 1:3, preferably 1:1.2 to 1:1.5, most preferably 1:1.3, based on the total amount of ⁇ -sitosterol in the reaction mixture, and reacted under a refluxed temperature for 10 min to 5 hrs, preferably, 30 min to 3 hrs, most preferably lhr. Finally, completion of the reaction is confirmed by thin layer chromatography (TLC) .
  • TLC thin layer chromatography
  • toluene, methylenechloride, dichloroethane, tetrahydrofuran, benzene or diethylether is employed as the organic solvent;
  • DMAP pyridine or TEA is employed as the basic catalyst;
  • DCC l-ethyl-3- [3' -dimethyl aminopropyl] carbodiimide, oxalyl chloride, carbonyl diimidazole, 2-chloropyridium, 2, 2' -dipyridyl disulfide or 2-imidazoyl disulfide is employed as the carboxyl group activating agent, respectively.
  • Step 2 Preparation of ⁇ -sitosterol ester of unsaturated fatty acid
  • the reaction mixture is filtered and the solvent is evaporated from the filtrate under a reduced pressure, the residue is mixed with methanol or methanol/acetone mixture (8: 2, v/v) violently at the temperature of 30 to 50 ° C, preferably 35 to 45 ° C, most preferably 40°C, and precipitated by chilling at -5 to 6°C, for 30 min to 30 hrs, preferably 1 to 10 hrs, most preferably 2 to 5 hrs, finally to give ⁇ -sitosterol ester of unsaturated fatty acid, i.e., ⁇ -sitosteryl oleate.
  • methanol or methanol/acetone mixture (8: 2, v/v) violently at the temperature of 30 to 50 ° C, preferably 35 to 45 ° C, most preferably 40°C, and precipitated by chilling at -5 to 6°C, for 30 min to 30 hrs, preferably 1 to 10 hrs, most preferably 2 to 5 hrs, finally to give ⁇ -sitosterol
  • the fat-soluble ester compound of the present invention can be dissolved in oil, for example, corn oil and sesame oil, and has physical properties like commercially available oil in a sense of quality.
  • ⁇ -sitosterol and oleic acid are representative examples of phytosterol and unsaturated fatty acid, respectively. Therefore, the present invention can be applied to all kinds of phytosterols such as stigmasterol, spinasterol, campesterol and sitosterol, and all kinds of unsaturated fatty acids such as linoleic acid and linolenic acid having the degree of unsaturation of 1 to 3.
  • corn oil is a representative example of liquid oil
  • oils such as sesame oil, olive oil, cotton seed oil, soy bean oil, safflower oil, rape seed oil, sunflower oil, peanut oil and rice bran oil.
  • Example 1 Esterification of ⁇ -sitosterol and oleic acid
  • Example 2-2 Precipitation by methanol/acetone mixture
  • ⁇ -sitosterol which is a representative plant sterol and a well-known inhibitor of cholesterol absorption
  • 6 week-old SPF SD male rats were used. Rats were housed in a room equipped with a 12-hour light-dark cycle with free access to tap water and ration during acclimatization for 1 week. They are not given the ration from 9 AM to 4 PM and were administered lOmg of unlabeled cholesterol suspended in 0.5ml of corn oil and/or 0.025mg of 14 C-cholesterol in 0.08 ml of ethanol for 3 days.
  • mice can freely access the ration and water from 3 hrs after the treatment of cholesterol and then are not fed overnight before being sacrificed. They are anesthetized with diethylether and the blood is collected from the heart.
  • rats are divided into 6 different groups and effects of phytosterol derivative and ⁇ -sitosterol were investigated, as shown in Table 1 below. Then, 6 ml of blood were collected from the hearts of rats and centrifuged at 2000xg for 20 min. To quantify the 14 C-cholesterol in the blood, 1.5 ml of supernatant (plasma) was taken and 10 ml of cocktail solution was added. Using a liquid scintillation counter, radioactivity was counted for 2 min per each sample. All data were represented as mean ⁇ SD, and statistical analysis of data was carried out by the Student's t-test. Significance of the value was accepted, when P was ⁇ 0.05.
  • ⁇ -sitosterol reduces the cholesterol absorption by about 30% as shown in Table 2 and the fat- soluble derivative also significantly reduced the cholesterol absorption by about 30% which is almost equally effective as ⁇ -sitosterol.
  • Table 2 Effects of sitosterol, fat-soluble derivative on the exogenous cholesterol absorption.
  • the present invention provides a method for manufacturing fat-soluble phytosterol or phytostanol ester of unsaturated fatty acid for inhibiting the intake of cholesterol and foodstuffs containing the same.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Botany (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

La présente invention concerne un procédé de fabrication d'ester de phytostérol ou de phytostanol liposoluble d'un acide gras insaturé pour l'inhibition de l'absorption de cholestérol et des aliments en contenant. Le procédé de fabrication d'ester de phytostérol ou de phytostanol liposoluble d'un acide gras insaturé comprend les étapes suivantes: estérification du phytostérol ou du phytostanol à acide gras insaturé par leur dissolution dans un solvant organique non polaire; la précipitation du produit estérifié dans le méthanol ou un mélange de méthanol et d'acétone, éliminant le solvant résiduel; et séchage du produit sous pression détendue.
PCT/KR1999/000569 1999-04-13 1999-09-21 Procede de fabrication d'ester de phytosterol ou du phytostanol liposoluble d'un acide gras insature WO2000061694A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU57634/99A AU5763499A (en) 1999-04-13 1999-09-21 Method for manufacturing fat-soluble phytosterol or phytostanol ester of unsaturated fatty acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1019990012965A KR100278194B1 (ko) 1999-04-13 1999-04-13 콜레스테롤 저하효과를 갖는 지용성 피토스테롤 또는 피토스타놀의 불포화 지방산 에스테르 화합물의 제조방법
KR1999/12965 1999-04-13

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001032035A1 (fr) * 1999-11-05 2001-05-10 Raisio Benecol Oy Melanges de graisses comestibles
WO2001072136A1 (fr) * 2000-03-27 2001-10-04 The J.M. Smucker Company Compositions a base d'esters de sterols
KR20020081834A (ko) * 2001-04-20 2002-10-30 주식회사 유엘바이오텍 식물성 스테롤의 유도체를 이용한 혈중 콜레스테롤저하제의 제조방법 및 이에 의해 제조된 혈중 콜레스테롤저하제
US6677327B1 (en) 1999-11-24 2004-01-13 Archer-Daniels-Midland Company Phytosterol and phytostanol compositions
KR100440613B1 (ko) * 2001-04-20 2004-08-16 주식회사 유엘바이오텍 식물성스테롤과 생 플라보노이드의 결합체를 이용한 혈중콜레스테롤 저하제의 제조방법과 이에 의해 제조한 혈중콜레스테롤 저하제
US7368138B2 (en) 2002-03-21 2008-05-06 Archer-Daniels-Midland Company Extraction of phytosterols from corn fiber using green solvents
CN102321138A (zh) * 2011-06-01 2012-01-18 江南大学 一种脂肪酸植物甾醇酯的新型制备方法
WO2013001126A1 (fr) * 2011-06-29 2013-01-03 Consejo Superior De Investigaciones Científicas (Csic) Procédé d'acylation pour l'obtention de composés d'intérêt alimentaire et/ou pharmaceutique à l'aide de stérol estérases fongiques
WO2016142745A1 (fr) 2015-03-11 2016-09-15 Tubitak Tisanes riches en polyphénols enrichies en stérols/stanols, dispersibles dans l'eau, sous forme aqueuse ou pulvérulente, servant à réduire les niveaux de cholestérol total et ldl
CN106117297A (zh) * 2016-06-28 2016-11-16 西安国邦实业有限公司 一种植物甾醇及甾醇酯的制备方法
CN106146595A (zh) * 2016-06-28 2016-11-23 西安国邦实业有限公司 一种从植物油脱臭馏出物中提取甾烯醇的方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100396211B1 (ko) * 2000-10-31 2003-09-17 (주)유진사이언스 천연물로 구성된 수용성 식물성 스테롤 유도체 및 이의염과 이들의 제조방법

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5117016A (en) * 1991-05-13 1992-05-26 Eastman Kodak Company Method for obtaining a stigmasterol enriched product from deodorizer distillate
WO1992019640A1 (fr) * 1991-05-03 1992-11-12 Raision Margariini Oy Substance servant a abaisser un taux de cholesterol eleve dans un serum, et procede de preparation de cette substance
WO1999025362A1 (fr) * 1997-11-14 1999-05-27 Cognis Deutschland Gmbh Utilisation de melanges de principes actifs contenant du phytostenol pour la production d'agents hypocholesterinemiques
WO1999056558A1 (fr) * 1998-05-06 1999-11-11 Raisio Benecol Oy Compositions de phytosterol

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992019640A1 (fr) * 1991-05-03 1992-11-12 Raision Margariini Oy Substance servant a abaisser un taux de cholesterol eleve dans un serum, et procede de preparation de cette substance
US5117016A (en) * 1991-05-13 1992-05-26 Eastman Kodak Company Method for obtaining a stigmasterol enriched product from deodorizer distillate
WO1999025362A1 (fr) * 1997-11-14 1999-05-27 Cognis Deutschland Gmbh Utilisation de melanges de principes actifs contenant du phytostenol pour la production d'agents hypocholesterinemiques
WO1999056558A1 (fr) * 1998-05-06 1999-11-11 Raisio Benecol Oy Compositions de phytosterol

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6562395B2 (en) 1999-11-05 2003-05-13 Raisio Benecol Ltd. Edible fat blends
US6827964B2 (en) 1999-11-05 2004-12-07 Raisio Benecol Ltd. Edible fat blends
WO2001032035A1 (fr) * 1999-11-05 2001-05-10 Raisio Benecol Oy Melanges de graisses comestibles
US6677327B1 (en) 1999-11-24 2004-01-13 Archer-Daniels-Midland Company Phytosterol and phytostanol compositions
WO2001072136A1 (fr) * 2000-03-27 2001-10-04 The J.M. Smucker Company Compositions a base d'esters de sterols
KR20020081834A (ko) * 2001-04-20 2002-10-30 주식회사 유엘바이오텍 식물성 스테롤의 유도체를 이용한 혈중 콜레스테롤저하제의 제조방법 및 이에 의해 제조된 혈중 콜레스테롤저하제
KR100440613B1 (ko) * 2001-04-20 2004-08-16 주식회사 유엘바이오텍 식물성스테롤과 생 플라보노이드의 결합체를 이용한 혈중콜레스테롤 저하제의 제조방법과 이에 의해 제조한 혈중콜레스테롤 저하제
US8114447B2 (en) 2002-03-21 2012-02-14 Archer Daniels Midland Company Extraction of phytosterols from corn fiber using green solvents
US7368138B2 (en) 2002-03-21 2008-05-06 Archer-Daniels-Midland Company Extraction of phytosterols from corn fiber using green solvents
CN102321138A (zh) * 2011-06-01 2012-01-18 江南大学 一种脂肪酸植物甾醇酯的新型制备方法
WO2013001126A1 (fr) * 2011-06-29 2013-01-03 Consejo Superior De Investigaciones Científicas (Csic) Procédé d'acylation pour l'obtention de composés d'intérêt alimentaire et/ou pharmaceutique à l'aide de stérol estérases fongiques
ES2395582A1 (es) * 2011-06-29 2013-02-13 Consejo Superior De Investigaciones Científicas (Csic) Procedimiento de acilación para la obtención de compuestos de interés alimenticio y/o farmacéutico utilizando esterol esterasas fúngicas.
WO2016142745A1 (fr) 2015-03-11 2016-09-15 Tubitak Tisanes riches en polyphénols enrichies en stérols/stanols, dispersibles dans l'eau, sous forme aqueuse ou pulvérulente, servant à réduire les niveaux de cholestérol total et ldl
CN106117297A (zh) * 2016-06-28 2016-11-16 西安国邦实业有限公司 一种植物甾醇及甾醇酯的制备方法
CN106146595A (zh) * 2016-06-28 2016-11-23 西安国邦实业有限公司 一种从植物油脱臭馏出物中提取甾烯醇的方法
CN106146595B (zh) * 2016-06-28 2018-01-02 西安国邦实业有限公司 一种从植物油脱臭馏出物中提取甾烯醇的方法
CN106117297B (zh) * 2016-06-28 2019-02-26 西安国邦实业有限公司 一种植物甾醇及甾醇酯的制备方法

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AU5763499A (en) 2000-11-14
KR20000012176A (ko) 2000-03-06

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