WO2008108817A1 - Complément nutritionnel avec de l'oleuropéine - Google Patents

Complément nutritionnel avec de l'oleuropéine Download PDF

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Publication number
WO2008108817A1
WO2008108817A1 PCT/US2007/020953 US2007020953W WO2008108817A1 WO 2008108817 A1 WO2008108817 A1 WO 2008108817A1 US 2007020953 W US2007020953 W US 2007020953W WO 2008108817 A1 WO2008108817 A1 WO 2008108817A1
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WIPO (PCT)
Prior art keywords
acid
oleuropein
juice
nutritional supplement
olive leaf
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PCT/US2007/020953
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English (en)
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Richard Hall
James Kwon
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Ameriden International, Inc.
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Application filed by Ameriden International, Inc. filed Critical Ameriden International, Inc.
Publication of WO2008108817A1 publication Critical patent/WO2008108817A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A23L2/04—Extraction of juices
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/28—Myrtaceae [Myrtle family], e.g. teatree or clove
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/40—Liliopsida [monocotyledons]
    • A01N65/44—Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass
    • 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
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/38—Other non-alcoholic beverages
    • 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)
    • A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates, in general, to a nutritional supplement and, more particularly, to a nutritional supplement preferably comprised of a processed olive leaf extract in which oleuropein is captured within cyclodextrin with the aid of glycerin ester, thereby greatly suppressing the bitterness of oleuropein.
  • Oleuropein is a naturally occurring compound commonly found in the leaves, fruit, bark and roots of olive trees.
  • the leaves of an olive tree are richer in oleuropein than the fruit and/or bark of the tree.
  • Oleuropein can also be obtained from other plants belonging to the family Oleaceae; for example, ash and privet trees.
  • oleuropein is known to have a resistant activity against a wide spectrum of bacteria, viruses, and fungi, producing various therapeutic effects, such as alleviation of hypertension, antioxidation, control of glucose levels in blood, etc.
  • oleuropein hydrolyzes to d-elenolic acid and 1-elenolic acid that has powerful antimicrobial effects.
  • the d-elenolic acid acts as a strong antimicrobial.
  • oleuropein has the ability to interfere with critical amino acid processes that are essential for virus replication, thus inhibiting the spread of such viruses.
  • oleuropein can also directly stimulate the formation of immune system cells through a process called phagocytosis in order to combat various types of microbes. Therefore, oleuropein acts as a potent natural antibiotic against viruses and bacteria.
  • oleuropein has been the source of great interest concerning coronary dilation (the expansion/contraction ability of the arteries). Tests have shown that the injection of oleuropein in animals has improved blood circulation by up to 50%. In addition to the coronary artery dilating effect, oleuropein has been found to display other cardiovascular health-enhancing effects, such as inducing a long-lasting effect of lowering elevated blood pressure (as proven using animals when arrhythmia was induced through the injection of chlorides or calcium compounds). More specifically, a study, conducted by the Pharmacology University of Granada, Spain, disclosed that oleuropeoside, an ingredient isolated from oleuropein, dilates the blood vessels. That is, oleuropeoside acts to relax and smoothen contracted blood vessels to improve blood circulation and thus to decrease blood pressure.
  • Oleuropein is also believed to directly promote insulin release in the human body and maximize the use of blood sugar. At least one study has found that oleuropein may play a pivotal role in glycemic control. The recordings of this lab disclosed that when 16 mg of oleuropeoside was administered to animals when diabetes had been induced by alloxan injection, blood sugar levels were significantly reduced in these injected animals. Oleuropein was observed to have a proposed mechanism of action, of potentiation, of glucose-induced insulin release, and an increase in peripheral blood glucose uptake.
  • Pickling the extract with salt and acetic acid may break down oleuropein decreasing its nutritional value. Fermenting the extract is a complicated process and is of limited use in producing beverage and processed foods. The thermal method of heating oleuropein to reduce the bitterness also reduces the preventive and therapeutic effects oleuropein has on maladies.
  • the oleuropein used in this nutritional supplement will be in the form of an extract from olive leaves having a high concentration thereof; however, it is understood that the oleuropein to be included may be obtained from other sources as well.
  • the invention is directed toward a processed olive leaf extract, including oleuropein, cyclodextrin and glycerin ester as its essential ingredients.
  • the processed olive leaf extract contains oleuropein in an amount from 0.5 to 1,000 mg, cyclodextrin in an amount from 0.5 to 100 mg, and glycerin ester in an amount from 2 to 1 ,500 mg.
  • the processed olive leave extract is preferably embodied in the form of a powdered or candied nutritional supplement that further includes additional ingredients selected from a group consisting of xylitol, an acid, calcium, a sweetener, and/or any combination thereof.
  • the processed olive leaf extract is embodied in the form of a powdered or candied nutritional supplement that further includes a sweetener
  • the sweetener is preferably selected from the group consisting of, but not limited to, xylitol, rebaudiosides , erythritol, saccharin, sucralose cyclamate, sugar alcohol, aspartame, fructooligosaccharides, fructose, hydrogenated starch hydrolysates, isomalt, lactitol, maltitiol, mannitol, sorbitol, sugar, sugar cane extract, fruit juice, succanat, honey, rice juice, Yinnie juice, licorice extract, D-tagatose, tagatose, glucose, corn juice, Japanese maple juice, agave fruit juice, and/or any combinations thereof.
  • FIG.l represents a graphical depiction of alpha, beta and gamma cyclodextrin molecules utilized in a preferred embodiment of the present invention
  • FIG. 2 represents a graphical representation of how the cavity of a cyclodextrin molecule can be utilized to capture an oleuropein molecule
  • FIG. 3 is a graphical representation of how alpha, beta and gamma cyclodextrin molecules reduce the bitterness of oleuropein. DESCRIPTION OF THE PREFERRED EMBODIMENTS
  • Oleuropein has the following structural composition:
  • O-CeH -i 1 05 is O- ⁇ - D -g Euco py ranose
  • oleuropein molecules obtained from olive leaf extract are captured within dextrin molecules to alleviate the bitter taste thereof. While the oleuropein molecules come from olive leaf extract in a preferred embodiment, it is understood that the invention may also use oleuropein obtained from any suitable source, such as oleuropein derived from the olive fruit, bark of an olive tree, or from any other plant source containing suitable oleuropein.
  • Dextrin is a generic term for all intermediate products, consisting of monosaccharides, formed during the hydrolysis of starch into sugars. Generally, most monosaccharides form cyclic structures, that predominate in aqueous solution, by forming hemiacetals or hemiketals (depending on whether they are aldoses or ketoses) between an alcohol (-OH) and the carbonyl group (-CHO) of the same sugar molecule.
  • cyclodextrin is an intermediate monosaccharide cyclic structure form of dextrin and used as a capturer of oleuropein.
  • Cyclodextrins (sometimes called cycloamyloses) make up a family of cyclic oligosaccharides, composed of five or more ⁇ -D-glucopyranoside units linked together. More specifically, typical cyclodextrins contain a number of glucose monomers ranging from six to eight units in a ring, creating a cone shape. Cyclodextrins are produced from starch by means of enzymatic conversion. Over the last few years, they have found a wide range of applications in food, pharmaceutical and chemical industries as well as agriculture and environmental engineering.
  • cyclodextrins typically contain a number of glucose monomers - ranging from six to eight units - which are formed in a ring. Among these are included: alpha-cyclodextrin ( ⁇ -cyclodextrin) for a six sugar ring molecule, beta- cyclodextrin ( ⁇ -cyclodextrin) for a seven sugar ring molecule, and gamma-cyclodextrin ( ⁇ -cyclodextrin) for an eight sugar ring molecule. Cyclodextrins are able to form host- guest complexes with hydrophobic molecules given the unique nature imparted by their structure.
  • each cyclodextrin contains one or more water molecules that are produced as a result of the linkage between glucose monomers. These water molecules are easily displaced. Accordingly, when heated, cyclodextrins have a molecular formation that thereby forms a "cavity" suitable for capturing and bonding with the oleuropein molecule resident in an olive leaf extract or other sources.
  • cyclodextrins when heated, cyclodextrins form a hydrophobic cavity therein that allow cyclodextrins to form inclusion complexes with a variety of substrate molecules, that is, non-polar suitably-sized aliphatic and aromatic compounds, such as aroma compounds and lipophilic drugs.
  • cyclodextrin is heated to form this cavity and then combined with oleuropein in order to surround the oleuropein and mask or reduce its bitter taste.
  • alpha ( ⁇ ), beta ( ⁇ ) and gamma ( ⁇ ) cyclodextrin molecular formations are illustrated with detailed dimensions given thereto.
  • these cyclodextrins are represented by a doughnut-shaped (truncated cone) molecule having a central cavity. Because ⁇ -, ⁇ -, and ⁇ -cyclodextrin can form cavities of different sizes when heated, it is desirable to use a cyclodextrin that is capable of forming a cavity corresponding to the size of the oleuropein molecule to be captured therein. More specifically, it is desirable to use a cyclodextrin that when heated will form a large enough cavity to accommodate an oleuropein molecule (molecular size: 5.92 ⁇ 0.49* 10-6 cm/s, P ⁇ 0.001).
  • beta- cyclodextrin ( ⁇ -cyclodextrin) is the most desirable because when heated it will form a cavity suitable for accommodating an oleuropein molecule therein without leaving too much unused space.
  • the combination is desirable when developing a nutritional supplement that is to be orally administered. More specifically, the combination of ⁇ -cyclodextrin and oleuropein allows for formation of a cohesive compound wherein the oleuropein can remain captured within the cavity of the ⁇ -cyclodextrin until the combination passes over the gustatory buds, so that the bitter taste normally associated with oleuropein is reduced and/or masked.
  • FIG. 3 is a graphical representation of how alpha, beta and gamma cyclodextrin molecules reduce the bitterness of oleuropein.
  • ⁇ -cyclodextrin having a cavity suitably sized to accommodate oleuropein, can suppress the bitterness of oleuropein to the greatest extent. Therefore, the present invention features capturing oleuropein molecules within the cavities of cyclodextrins in order to reduce and/or mask the bitterness of oleuropein for easy ingestion.
  • cyclodextrins cannot completely surround them and envelope them. More specifically, as can be seen from the illustration shown in FIG.
  • oleuropein while contained within the cyclodextrin, remains at least partially exposed. Accordingly, it is desirable to further combine an additional agent for forming one complete and cyclical encapsulation of the oleuropein molecule. Therefore, there is a need for an additional, intermediary ingredient that can ensure the longevity of the bonding and joining of oleuropein molecules with cyclodextrin molecules and can complete the encapsulation of the oleuropein molecule so that it is not exposed, thereby more completely reducing and/or masking the bitter taste.
  • oleuropein is stably fixed to and contained within cyclodextrin by preferably using an additional ingredient such as glycerin.
  • Glycerin is a neutral, sweet-tasting, colorless liquid that freezes to a gummy paste and that has a high boiling point. Glycerin can be dissolved into water or alcohol, but not oils. On the other hand, many things will dissolve into glycerin easier than they do into water or alcohol. So glycerin is a good solvent. Glycerin is also highly “hygroscopic" which means that it absorbs water from the air. Glycerin has the following chemical formula.
  • Glycerin is joined with fatty acids by dehydration synthesis to form glycerin ester, represented by the following chemical formula.
  • glycerin ester is amphiphilic, having both a hydrophilic moiety and a lipophilic moiety. Because of its non-ionic surface active agent qualities glycerin ester is a preferred form of glycerin used to complete the encapsulation process. Because of the inhibitory activity of oleuropein against a broad spectrum of microbes, the present invention finds application in the medicinal and food industries, including, but not limited to, natural antibiotics and mouthwashes. It is further desirable to use the combination of oleuropein, cyclodextrin and glycerin ester in order to form a food product and/or nutritional supplement.
  • the above referenced combination can preferably be further implemented into an ingestible, consumable food product or nutritional supplement designed to inhibit harmful microbes in the mouth as well as in the body to provide the benefits enunciated hereinabove.
  • oleuropein, cyclodextrin and glycerin ester are further combined into a consumable nutritional supplement in the form of an ingestible food product that can be eaten/consumed.
  • this food product is formed as a crystallized candy-like or a powdered substance that can be consumed directly or mixed with a fluid product such as juice or water.
  • this food product may include, but not be limited to, the form of a gum, gel, a hard candy, a soft candy, or a liquid.
  • the oleuropein used in forming this product is preferably in the form of an olive leaf extract (that may include other minerals and nutrients derived from an olive leaf), although other forms and sources of oleuropein are intended to be included herewith.
  • Oleuropein 0.5 - 1,000
  • Milling Mill glycerin ester to a very fine powder and heat to 30°- 40° Celsius, 86°- 104° Fahrenheit and store. Mill olive leaf extract to a fine powder and mix together with the stored glycerin ester.
  • lactic acid esters of monoglyceride citric acid esters of monoglyceride, succinic acid esters of monoglyceride, diacetyltartaric acid esters of monoglyceride, polyglycerol esters of fatty acids, polyglycerol polyricinoleate, propylene glycol esters of fatty acids, sucrose esters of fatty acids, lecithin, or enzyme-treated lecithin may be used in place of the glycerin ester as an alternative thereto.
  • Blending/Sifting Combine heated glycerin with the milled olive leaf extract. Since the ratio between the glycerin ester and the olive leaf extract varies with the oleuropein content of the olive leaf extract, in the present invention, an olive leaf extract with a preferred oleuropein content of 20-25% by weight is used, with a weight ratio of 3:7 olive leaf extract to glycerin ester is preferred.
  • the combined mixture (the glycerin ester and olive leaf extract) is then blended - preferably using a commercial machine for 1 hour and 45 minutes - and then passed through a sieve until the mixture is homogeneous.
  • cyclodextrin preferably beta-cyclodextrin
  • Add cyclodextrin preferably beta-cyclodextrin
  • Heat the mixture to 40°-60° Celsius, 104°- 140° Fahrenheit for 2 hours and then allow the mixture to cool down to 20°Celsius/68° Fahrenheit. Then, pass the mixture through a narrow sieve until the total mixture is homogeneous and store.
  • Cyclodextrin which is used to mask or reduce the bitterness, may be exemplified by cellulosine, ⁇ -, ⁇ -, and ⁇ - cyclodextrin, ⁇ -hydroxypropyl cyclodextrin, and/or trapposal (trade name) cyclodextrin.
  • phosphoric acid boric acid, sodium dodecyl sulfate (SDS), octane, butan-1-ol, chromic acid, tetradecyltrimethylammonium bromide (TTAB), ethanesulfonic acid (MES), formic acid, imidazole, Methanol (MeOH), acetone (ACN), sodium acetate, acetic acid, or ammonium acetate may be used instead of cyclodextrin.
  • SDS sodium dodecyl sulfate
  • TTAB tetradecyltrimethylammonium bromide
  • MES ethanesulfonic acid
  • formic acid imidazole
  • Methanol Methanol
  • ACN acetone
  • sodium acetate acetic acid
  • ammonium acetate may be used instead of cyclodextrin.
  • Cyclodextrins are able to form host-guest complexes with hydrophobic molecules given the unique nature imparted by their structure. As a result these molecules have found a number of applications in a wide range of fields. In the food industry cyclodextrins are employed for the preparation of cholesterol free products. Other food applications further include the ability to stabilize volatile or unstable compounds and reduction of unwanted tastes. The ability of cyclodextrins to form complexes with hydrophobic molecules has led to their usage in supramolecular chemistryfg.h) and is part of this process.
  • Cyclodextrins can be represented as toroids and because of this arrangement cyclodextrins can host inclusion compounds/complexes that greatly modify the physical and chemical properties of the guest molecule, mostly in terms of water solubility. This is one reason why cyclodextrins have attracted much interest in many fields, especially pharmaceutical application.
  • the present embodiment presents a further development of potentiation in that when mixed with glycerin esters, encapsulates the potentially exposed end of the cyclodextrin thus disallowing the host complex to be realized at gustation.
  • the processed enclosure is referred to as cyclo-encapsulation.
  • xylitol used in this process has to be prepared prior to mixing with the primary homogeneous mixture by liquefying and adding natural or synthetic colors. Dry the prepared xylitol and coloring to less than 5% moisture. Add the mixture of the prepared xylitol as a sweetener to the stored primary homogeneous mixture, blend thoroughly and pass through a sieve several times.
  • a substitute sweetener may be selected and used from this set of sweeteners including, but not limited to, xylitol, rebaudiosides, erythritol, saccharin, sucralose cyclamate, sugar alcohol, aspartame, fructooligosaccharides, fructose, hydrogenated starch hydrolysates, isomalt, lactitol, maltitiol, mannitol, sorbitol, sugar, sugar cane extract, fruit juice, succanat, honey, rice juice, Yinnie juice, licorice extract, D-tagatose, tagatose, glucose, corn juice, Japanese maple juice, and agave fruit juice.
  • sweeteners including, but not limited to, xylitol, rebaudiosides, erythritol, saccharin, sucralose cyclamate, sugar alcohol, aspartame, fructooligosaccharides, fructose, hydrogenated starch hydrolysates,
  • citric acid (synthesized or naturally obtained from fruit, peanuts, vegetables or animals) may be used in place of the sweetener.
  • the following sour taste substitutes may include, but not be limited to, citric acid, tartaric acid, malic acid, lactic acid, acetic acid, and/or succinic acid, monoprotic acid, diprotic acid, triprotic acid, and polyprotic acid.
  • citric acid synthesized or naturally obtained from fruit, peanuts, vegetables or animals This citric acid may be in the form of monohydrate or anhydrate, liquid, powder or lyophilized.
  • the preceding method of manufacture should take place in a moisture controlled facility that has the ability to restrict moisture to less than 5%, store materials at less than 1%, and maintain a 20° Celsius (68° Fahrenheit) temperature. Moreover, the method of manufacture provided should follow Over The Counter (OTC) and or Certified Good Manufacturing Practice (cGMP) requirements intended for commercial distribution currently in the United States, Australia, Asia and Europe.
  • OTC Over The Counter
  • cGMP Certified Good Manufacturing Practice
  • the present invention provides a processed olive leaf extract that has oleuropein molecules captured within cyclodextrin, thus being greatly reduced in bitterness.
  • the processed olive leaf extract of the present invention is easy to consume. The reduced and/or masked bitterness allows the oleuropein to find various applications.

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Abstract

Complément nutritionnel dans lequel des molécules d'oleuropéine sont capturées dans la cyclodextrine à l'aide d'ester de glycérine.
PCT/US2007/020953 2007-03-06 2007-09-28 Complément nutritionnel avec de l'oleuropéine WO2008108817A1 (fr)

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KR1020070021940A KR100878549B1 (ko) 2007-03-06 2007-03-06 가공된 올리브 잎 추출물
KR10-2007-0021940 2007-03-06

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
JP2016132657A (ja) * 2015-01-22 2016-07-25 国立研究開発法人産業技術総合研究所 活動量の低下及び／又は不安の改善用組成物
ES2813774A1 (es) * 2019-09-20 2021-03-24 Univ Sevilla Procedimiento para la extraccion en hoja de olivo de oleuropeina en una fraccion fenolica, composicion alimentaria funcional y uso
FR3119767A1 (fr) * 2021-02-18 2022-08-19 Nmc Lab Composition pour renforcer le système immunitaire
US11446013B2 (en) 2016-07-01 2022-09-20 Swan Cytologics, Inc. Method and apparatus for extracting and delivery of entities

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US20070020340A1 (en) * 2005-07-25 2007-01-25 David Rubin Fish oil products for reducing cholesterol, low density lipoprotein, and hypertension

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US571415A (en) * 1896-11-17 William h
US20030086986A1 (en) * 1998-08-06 2003-05-08 Bruijn Chris De Ophthalmic, pharmaceutical and other healthcare preparations with naturally occurring plant compounds, extracts and derivatives

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US20070020340A1 (en) * 2005-07-25 2007-01-25 David Rubin Fish oil products for reducing cholesterol, low density lipoprotein, and hypertension

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016132657A (ja) * 2015-01-22 2016-07-25 国立研究開発法人産業技術総合研究所 活動量の低下及び／又は不安の改善用組成物
US11446013B2 (en) 2016-07-01 2022-09-20 Swan Cytologics, Inc. Method and apparatus for extracting and delivery of entities
ES2813774A1 (es) * 2019-09-20 2021-03-24 Univ Sevilla Procedimiento para la extraccion en hoja de olivo de oleuropeina en una fraccion fenolica, composicion alimentaria funcional y uso
WO2021053259A1 (fr) * 2019-09-20 2021-03-25 Universidad De Sevilla Procédé pour extraire, à partir d'une feuille d'olivier, de l'oleuropéine dans une fraction phénolique, composition alimentaire et son utilisation
FR3119767A1 (fr) * 2021-02-18 2022-08-19 Nmc Lab Composition pour renforcer le système immunitaire
WO2022175470A1 (fr) * 2021-02-18 2022-08-25 Nmc Lab Composition pour renforcer le systeme immunitaire

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