WO2010128243A1 - Procédé de préparation d'extraits polyphénoliques à partir de feuilles d'épinards - Google Patents
Procédé de préparation d'extraits polyphénoliques à partir de feuilles d'épinards Download PDFInfo
- Publication number
- WO2010128243A1 WO2010128243A1 PCT/FR2010/050848 FR2010050848W WO2010128243A1 WO 2010128243 A1 WO2010128243 A1 WO 2010128243A1 FR 2010050848 W FR2010050848 W FR 2010050848W WO 2010128243 A1 WO2010128243 A1 WO 2010128243A1
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- WO
- WIPO (PCT)
- Prior art keywords
- liquid
- extract
- water
- crude
- oily phase
- Prior art date
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Classifications
-
- 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)
- A61K36/21—Amaranthaceae (Amaranth family), e.g. pigweed, rockwort or globe amaranth
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
Definitions
- the present invention relates to a new process for preparing concentrated and purified polyphenolic extracts from spinach leaves.
- Spinach (Spinacia oleracea) is an annual or biennial vegetable plant of the family Chenopodiaceae. This plant is commonly grown and consumed in the usual diet.
- spinach In traditional use, spinach is considered, among other things, as a strengthening, revitalizing, muscle toning, including heart muscles. Its richness in carotenes, vitamins (especially C, E), minerals and trace elements (especially magnesium, iron, calcium, potassium) make it an excellent indication against general fatigue and depressive states.
- the object of the present invention is therefore to provide a process for the preparation of concentrated spinach extracts rich in polyphenols.
- the present invention also aims to provide spinach extracts having a high content of polyphenols, said extracts are therefore intended for applications for improving the performance of striated muscles in humans or animals.
- the present invention relates to a process for the preparation of a concentrated extract of spinach, in liquid or dry form, with a polyphenol titer greater than or equal to 50%, comprising a step of purifying a crude extract of spinach in the form of liquid, by a liquid-liquid extraction technique with a food oil.
- the edible oil is selected from the group consisting of olive oil, sunflower, grape seed, fish, and mixtures thereof.
- the method according to the present invention comprises the following steps:
- said crude liquid extract with added edible oil is subjected to a concentration step under vacuum and with stirring, in order to obtain a supernatant oily phase comprising the chlorophyll and carotenoid pigments and an aqueous phase comprising the water-soluble compounds (carbohydrates, proteins, phenolic compounds). simple or complex );
- the step of extracting the crude liquid extract of the invention with edible oil makes it possible to obtain a refined extract having a high titre in active principle (s).
- said crude extract is subjected to a purification step.
- This purification step is carried out by combining two steps. The first step is to eliminate the chlorophyll-type dye compounds, while obtaining a product that can be valorized as a high-quality dietary green dye, the pigments having been preserved from the oxidative degradation phenomena generally occurring during concentration. , by this way.
- the crude extract in liquid form is supplemented with an ordinary food oil, such as olive oil, sunflower, grape seed, fish, or any other food oil of identical characteristic, in proportions ranging from 1 / 1 to 1/1000 depending on the desired chlorophyll concentration.
- the crude liquid extract added with oil is then in particular concentrated under vacuum and with stirring, with a material of evapo-concentrator type, or vacuum ball. This step will further reduce the volume of product, as well as the elimination of alcohol in the case of extraction by hydro-alcoholic mixture.
- the product obtained is in the form of a biphasic mixture, the oily phase supernatant containing the chlorophyll and carotenoid pigments preserved from oxidative phenomena, the aqueous phase comprising all the water-soluble compounds such as carbohydrates, proteins and simple or complex phenolic compounds.
- the separation of the mixture can be improved by adding a sufficient proportion of water.
- the above-mentioned oily phase is then recovered and is preferably subjected to one or more washing steps with water, and if necessary, dried to obtain a coloring powder.
- the aforementioned washing step of the oily phase with water makes it possible to increase the recovery of water-soluble compounds which may be emulsified with the oily phase.
- This oily phase can be directly valued as a natural green food dye, even biological, starting from spinach from organic farming.
- This oily phase can also be spray-dried, using suitable drying supports such as caseinates, maltodextrins, lecithins, in order to obtain a water-dispersible coloring powder.
- the collected aqueous phase as defined above, containing especially polyphenols, can be dried directly or undergo a second refining.
- the aqueous phase obtained at the end of the extraction step with the edible oil is recovered and then dried in order to obtain a concentrated extract in dry form.
- the aqueous phase obtained at the end of the extraction step with the edible oil is recovered and then subjected to a purification step to obtain a purified concentrated extract.
- This additional purification step can be carried out by passage over adsorbent resins and with elution with an alcohol-type solvent, or by liquid-liquid extraction, using a solvent immiscible with water such as ethyl acetate, butanol or any other solvent having an affinity with the phenolic compounds.
- the chromatography resins used can be, for example, ion exchange type (anion or cation), or adsorption / desorption type, for example of the divinylbenzene / styrene copolymer, polystyrenic or polymethacrylic type, marketed in particular by the Rohm & Haas brands or Mitsubishi Chemical.
- the method of the invention may comprise additional steps of obtaining extracts more concentrated in active principles.
- the purified extract obtained at the end of the purification by chromatography or by liquid-liquid extraction with ethyl acetate or butanol can then be concentrated either by evaporation under vacuum or by membrane nanofiltration, in order to obtain a concentrate containing between 15 and 70% of solids.
- this purified concentrate can then be dried using equipment such as atomizer dryer, lyophilizer or vacuum dryer.
- the present invention therefore also relates to the preparation of a purified concentrated extract in dry form, said dry form being obtained by drying a purified concentrated extract in liquid form.
- the drying steps performed to obtain dry forms are carried out by atomization.
- the present invention also relates to a process as defined above, characterized in that the spinach crude extract in liquid form is obtained by a process comprising an extraction step by placing spinach in fresh form or frozen with a solvent selected from the group consisting of water, ethanol and mixtures thereof.
- the spinach used in the process of the invention comes from the whole plant, in fresh or dry form.
- the crude extract of spinach according to the invention is obtained by placing the plant, in its fresh or frozen form, with a solvent, such as water, ethanol or a mixture of water and ethanol in proportions ranging from 100/0 to 0/100, for an extraction step, in separating the plant and the solvent to obtain a crude extract in liquid form.
- a solvent such as water, ethanol or a mixture of water and ethanol in proportions ranging from 100/0 to 0/100
- the crude extract in liquid form is dried, for example by removal of water in a stream of hot air, by nebulization, by evaporation, by sublimation, by dehydration, by adsorption on support.
- the present invention also relates to a process for preparing a coloring product, comprising the following steps:
- said crude liquid extract supplemented with edible oil, is subjected to a concentration step under vacuum and with stirring, in order to obtain a supernatant oily phase comprising the chlorophyll and carotenoid pigments and an aqueous phase comprising the water-soluble compounds,
- the oily phase is recovered for subjecting it to one or more washing steps with water in order to obtain a liquid dye product, and, if necessary, the washed oily phase is dried in order to obtain a coloring powder.
- This method therefore makes it possible to obtain a dye product in liquid form or in dry form.
- the present invention therefore also relates to a dye product, in liquid or dry form, obtainable by the process as defined above.
- Said dye product in liquid form can thus be used as a green food dye.
- the present invention also relates to a concentrated extract of spinach, obtainable according to the preparation process as defined above.
- the concentrated extracts of the invention are characterized in that they have a total polyphenol titer greater than or equal to 50%.
- the present invention also relates to a concentrated extract of spinach, in liquid or dry form, with a total polyphenol titer greater than or equal to 50%, preferably ranging from 60% to 100%, and preferably from 90% to 100%.
- the polyphenols are determined by spectrophotometry and HPLC (for example according to the method described below).
- the extracts of the invention comprise mainly polyphenolic compounds, and preferably at least
- polyphenolic compounds there are essentially compounds of the family of flavonoids and in particular of the chemical class of flavonols.
- the four major polyphenolic representatives used in the spinach extracts of the invention are the following: patulinin, spinacetin, jacéidine and spinatoside (in simple or glucosylated form). More exactly, the spinach extracts of the invention comprise the following compounds: patuletin-3-glucosyl- (1-6) -apiosyl (1-2) -glucoside, patuletin-3-glucosyl- (1-6) - glucoside, spinacetin-3-glucosyl- (1 -6) -apiosyl (1-2) -glucoside, spinacetin-3-glucosyl- (1-6) -glucoside, spinacetin-3-feruloylglucosyl- (1-6) -glucoside , spinatoside, jacéidine-4'-glucuronide,
- Phenolic acids are also present in the extracts of the invention, in particular o-coumaric acid, ferulic acid, p-coumaric acid and glucuronic acid.
- the ecdysteroids commonly called phytoecdysteroids are also present in the extracts of the invention.
- the present invention also relates to a pharmaceutical composition comprising a spinach extract as defined above, in combination with a pharmaceutically acceptable vehicle.
- the present invention also relates to a dietary supplement comprising a spinach extract as defined above, in combination with an acceptable vehicle.
- the spinach extracts of the invention are intended for various applications, in particular for improving the performance of striated muscles in humans or animals.
- the consumption of said extract makes it possible to reduce the compounds resulting from the oxidative muscle metabolism and the derived metabolites altering the muscle performance and increasing the recovery time.
- the present invention also relates to the use of said extract in preparations in different galenical forms, for the purpose of administration to humans or animals, whether in a medicinal form, or a food supplement, or dietary product.
- the application of said preparations concerns all human or animal populations, for which the contribution to the improvement of muscle performance and the increase of the recovery capacity is of interest, such as experienced sportsmen, occasional sportsmen requiring assistance. for after-exercise recovery, older adults who have difficulty recovering from physical activity and race or older animals.
- the present invention relates to spinach extracts as defined above for their use for improving muscle performance.
- the present invention also relates to spinach extracts as defined above for their use for the treatment and prevention of musculoskeletal disorders.
- the present invention also relates to spinach extracts as defined above for their use for the treatment and prevention of muscle disorders consecutive to the effort. LEGEND OF THE FIGURE
- FIG. 1 represents the UV chromatogram at 280 nm of a purified spinach extract obtained according to the method of the invention (purified extract No. 1 - see examples).
- the method used for the determination of total polyphenols is as follows.
- the chromatographic system used is Agilent Technologie 1,100 series.
- the different polyphenols are separated using a Kromasil C18 column, 250 mm x 4.6 mm - 5 ⁇ m, provided with a pre-column of the same nature.
- Millipore Ultra-Pure water acetonitrile is used as the solvent.
- gallic acid is used as analytical standards.
- solvent A HPLC acidified water pH 2.5 with orthophosphoric acid
- 100 mg of extract to be analyzed are weighed into a 50 ml volumetric flask and dissolved for 10 minutes by ultrasound with the solubilizing solvent and then made to volume.
- the polyphenol content is calculated according to the following formula: A _ E xm ⁇ x V
- a E peak area of the polyphenol X of the analyzed solution
- a ⁇ peak area of the polyphenol X of the control solution
- m E mass of the test sample of the analyzed solution (in mg)
- m ⁇ mass of the test sample of the corresponding control polyphenol X (in mg)
- V ⁇ volume in which the polyphenol X was solubilized (in ml)
- V E volume in which the analyzed extract was solubilized (in ml_)
- d dilution factor if necessary
- the water may be supplemented with enzymes such as cellulases and hemicellulases, or any other enzyme for liquefying fruits or vegetables.
- enzymes such as cellulases and hemicellulases, or any other enzyme for liquefying fruits or vegetables.
- the charged solvent water
- the charged solvent water
- the filtered charged solvent is added with olive oil, at a rate of 1 kg of oil, per kg of dry matter in the liquid.
- the charged solvent-oil mixture is then concentrated by evaporation under vacuum in a falling-film evaporator.
- the heating temperature is maintained at a temperature below 60 ° C.
- the concentration operation is conducted until reduction by 20 of the total volume.
- the concentrated oil / aqueous phase mixture is then washed with softened water at 10 ° C. at the rate of 1 volume of water per volume of initial mixture.
- This phase of liquid-liquid extraction with a food oil makes it possible to eliminate from the residual aqueous phase all of the lipophilic components, in particular the pigments, while preserving the entirety of the polyphenolic components of interest.
- the oily phase is separated and filtered, and is a lipid solution of chlorophyll and carotenoid pigments. This can be used directly in food coloring preparations.
- the aqueous concentrate constitutes a liquid refined extract (refined extract No. 1), which can be converted to powder by removal of the solvent, for example by drying under vacuum.
- the charged solvent (ethanol) is separated from the solid material in suspension and filtered.
- the filtered solvent is added with grape seed oil, at a rate of 1 L of oil per kg of dry matter.
- a natural antioxidant vitamin E type can be added to the mixture.
- the mixture is then dealcoholized by distillation and concentration under high vacuum.
- the resulting concentrate is separated in two by collecting the oily phase containing the chlorophyll and carotenoid pigments.
- the aqueous phase is collected separately.
- This phase of liquid-liquid extraction using a food oil, carried out during a concentration operation, makes it possible to eliminate from the residual aqueous phase all of the lipophilic components in particular the pigments, while preserving the entirety of the polyphenolic components of interest.
- the oily phase concentrated in pigments can be used directly after filtration as a green food coloring. It can also be dried on a support composed of maltodextrins, caseins and soy lecithins, in order to obtain a green and water-dispersible coloring powder.
- the aqueous concentrate constitutes a liquid refined extract (refined extract No. 2), which can be converted into crude powder extract by removal of the solvent, for example by drying under vacuum or atomization.
- the charged solvent (ethanol) is separated from the solid material in suspension and then filtered.
- the filtered solvent is added with grape seed oil, at a rate of 1 L of oil per kg of dry matter.
- a natural antioxidant vitamin E type can be added to the mixture.
- the mixture is then dealcoholized by distillation and concentration under high vacuum.
- the resulting concentrate is separated in two by collecting the oily phase containing the chlorophyll and carotenoid pigments.
- the aqueous phase is collected separately.
- This phase of liquid-liquid extraction with the aid of a food oil, carried out during a concentration operation, makes it possible to eliminate from the residual aqueous phase all of the lipophilic components, in particular the pigments, while preserving all the polyphenolic components of interest.
- the oily phase concentrated in pigments can be used directly after filtration as a green food coloring. It can also be dried on a support composed of maltodextrins, caseins, and soy lecithins, in order to obtain a green and water-dispersible coloring powder.
- the aqueous concentrate constitutes a liquid refined extract (refined extract No. 2), which can be converted into crude powder extract by removal of the solvent, for example by drying under vacuum or atomization.
- the refined extract No. 2 is subjected to a purification step by chromatography on divinylstyrenebenzene type resin (XAD 16 from Rohm & Haas), allowing an adsorption / desorption process suitable for polyphenols.
- the adsorbed compounds are desorbed from the resin by washing it with a 60% vol hydro-alcoholic solution at 35 ° C.
- the eluate thus obtained is then the purified extract, which can also be stored in liquid or dry form.
- this extract comprises the following compounds: ferulic acid (peak No. 1); patuletin-3-glucosyl- (1 -6) -apiosyl (1-2) glucoside (peak No. 2); patuletin-3-glucosyl- (1-6) -glucoside (peak No. 3); spinacetin-3-glucosyl- (1-6) -apiosyl (1-2) -glucoside (peak No. 4); spinacetin-3-glucosyl- (1 -6) -glucoside (peak No. 5); spinacetin-3-feruloylglucosyl- (1-6) -glucoside (peak # 6); spinatoside (peak no. 8); jaceidin-4'-glucuronide (peak # 9);
- the refined extract No. 3 is subjected to a purification step by liquid-liquid extraction with ethyl acetate.
- the ethyl acetate collected contains the polyphenol fraction of interest, which then constitutes the purified extract, which can also be stored in liquid or dry form.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
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- Engineering & Computer Science (AREA)
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Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/318,887 US8664185B2 (en) | 2009-05-04 | 2010-05-04 | Method for preparing polyphenol extracts from spinach leaves |
RU2011149200/15A RU2519640C2 (ru) | 2009-05-04 | 2010-05-04 | Способ приготовления полифенольных экстрактов из листьев шпината |
CN201080027391.6A CN102510754B (zh) | 2009-05-04 | 2010-05-04 | 从菠菜叶制备多酚提取物的方法 |
AU2010244324A AU2010244324A1 (en) | 2009-05-04 | 2010-05-04 | Method for preparing polyphenol extracts from spinach leaves |
CA2761143A CA2761143A1 (fr) | 2009-05-04 | 2010-05-04 | Procede de preparation d'extraits polyphenoliques a partir de feuilles d'epinards |
SG2011089703A SG176668A1 (en) | 2009-05-04 | 2010-05-04 | Method for preparing polyphenol extracts from spinach leaves |
MX2011011720A MX2011011720A (es) | 2009-05-04 | 2010-05-04 | Procedimiento de preparacion de extractos polifenolicos a partir de hojas de espinaca. |
HK12112178.5A HK1171374A1 (en) | 2009-05-04 | 2012-11-27 | Method for preparing polyphenol extracts from spinach leaves |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0952947A FR2944970B1 (fr) | 2009-05-04 | 2009-05-04 | Procede de preparation d'extraits polyphenoliques a partir de feuilles d'epinards |
FR0952947 | 2009-05-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010128243A1 true WO2010128243A1 (fr) | 2010-11-11 |
Family
ID=41162710
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2010/050848 WO2010128243A1 (fr) | 2009-05-04 | 2010-05-04 | Procédé de préparation d'extraits polyphénoliques à partir de feuilles d'épinards |
Country Status (11)
Country | Link |
---|---|
US (1) | US8664185B2 (fr) |
CN (1) | CN102510754B (fr) |
AU (1) | AU2010244324A1 (fr) |
CA (1) | CA2761143A1 (fr) |
CL (1) | CL2011002780A1 (fr) |
FR (1) | FR2944970B1 (fr) |
HK (1) | HK1171374A1 (fr) |
MX (1) | MX2011011720A (fr) |
RU (1) | RU2519640C2 (fr) |
SG (1) | SG176668A1 (fr) |
WO (1) | WO2010128243A1 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2627450C1 (ru) * | 2015-09-11 | 2017-08-08 | Федеральное государственное бюджетное учреждение науки Институт биологии Коми научного центра Уральского отделения Российской академии наук | Экстракт из листьев шпината и способ его получения |
EP3231294A1 (fr) * | 2016-04-11 | 2017-10-18 | Symrise AG | Composition et production d'extrait d'épinard avec du beta-ecdyson |
CN111039841B (zh) * | 2018-10-12 | 2022-09-02 | 江苏省农业科学院 | 一种从绿叶蔬菜中同时提取类胡萝卜素与多酚的方法 |
CN112998181A (zh) * | 2021-03-18 | 2021-06-22 | 中国科学院近代物理研究所 | 高活性甜高粱多酚及其制备方法与应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080138393A1 (en) * | 2006-12-11 | 2008-06-12 | Access To Business Group International Llc | Water soluble extract of spinach for prevention and repair of DNA damage |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1761089A1 (ru) * | 1990-08-24 | 1992-09-15 | Одесский технологический институт пищевой промышленности им.М.В.Ломоносова | Способ сушки листьев шпината |
CN1067916A (zh) * | 1991-06-25 | 1993-01-13 | 中国科学院西北高原生物研究所 | 沙棘属植物全果油的提取方法 |
FR2780859B1 (fr) * | 1998-07-13 | 2000-09-22 | Xeda International | Procede de traitement des fruits et legumes |
US20060201056A1 (en) * | 2000-04-14 | 2006-09-14 | Oryxe Energy International, Inc. | Biodiesel fuel additive |
-
2009
- 2009-05-04 FR FR0952947A patent/FR2944970B1/fr not_active Expired - Fee Related
-
2010
- 2010-05-04 WO PCT/FR2010/050848 patent/WO2010128243A1/fr active Application Filing
- 2010-05-04 MX MX2011011720A patent/MX2011011720A/es active IP Right Grant
- 2010-05-04 RU RU2011149200/15A patent/RU2519640C2/ru not_active IP Right Cessation
- 2010-05-04 SG SG2011089703A patent/SG176668A1/en unknown
- 2010-05-04 AU AU2010244324A patent/AU2010244324A1/en not_active Abandoned
- 2010-05-04 CN CN201080027391.6A patent/CN102510754B/zh not_active Expired - Fee Related
- 2010-05-04 US US13/318,887 patent/US8664185B2/en not_active Expired - Fee Related
- 2010-05-04 CA CA2761143A patent/CA2761143A1/fr not_active Abandoned
-
2011
- 2011-11-04 CL CL2011002780A patent/CL2011002780A1/es unknown
-
2012
- 2012-11-27 HK HK12112178.5A patent/HK1171374A1/xx not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080138393A1 (en) * | 2006-12-11 | 2008-06-12 | Access To Business Group International Llc | Water soluble extract of spinach for prevention and repair of DNA damage |
Non-Patent Citations (3)
Title |
---|
BERGQUIST SARA A M ET AL: "Flavonoids in baby spinach (Spinacia oleracea L.): Changes during plant growth and storage", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 53, no. 24, November 2005 (2005-11-01), pages 9459 - 9464, XP002551117, ISSN: 0021-8561 * |
FERRERES F ET AL: "Acylated flavonol glycosides from spinach leaves (spinacia oleracea)", PHYTOCHEMISTRY, PERGAMON PRESS, GB, vol. 45, no. 8, 1 August 1997 (1997-08-01), pages 1701 - 1705, XP004293339, ISSN: 0031-9422 * |
LOMNITSKI L ET AL: "COMPOSITION, EFFICACY, AND SAFETY OF SPINACH EXTRACTS", NUTRITION AND CANCER, LONDON, GB, vol. 46, no. 2, 1 January 2003 (2003-01-01), pages 222 - 231, XP009041973, ISSN: 0163-5581 * |
Also Published As
Publication number | Publication date |
---|---|
FR2944970B1 (fr) | 2012-11-30 |
CL2011002780A1 (es) | 2012-04-09 |
CA2761143A1 (fr) | 2010-11-11 |
SG176668A1 (en) | 2012-01-30 |
FR2944970A1 (fr) | 2010-11-05 |
AU2010244324A1 (en) | 2011-12-15 |
US20120196818A1 (en) | 2012-08-02 |
HK1171374A1 (en) | 2013-03-28 |
MX2011011720A (es) | 2012-06-01 |
US8664185B2 (en) | 2014-03-04 |
RU2519640C2 (ru) | 2014-06-20 |
CN102510754B (zh) | 2015-01-21 |
CN102510754A (zh) | 2012-06-20 |
RU2011149200A (ru) | 2013-06-10 |
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