[go: up one dir, main page]

US20060116510A1 - Isoflavone concentrates, as well as methods for their production - Google Patents

Isoflavone concentrates, as well as methods for their production Download PDF

Info

Publication number
US20060116510A1
US20060116510A1 US11/329,173 US32917306A US2006116510A1 US 20060116510 A1 US20060116510 A1 US 20060116510A1 US 32917306 A US32917306 A US 32917306A US 2006116510 A1 US2006116510 A1 US 2006116510A1
Authority
US
United States
Prior art keywords
concentrate
approximately
weight
isoflavone
polysorbate
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
US11/329,173
Inventor
Dariush Behnam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aquanova AG
Original Assignee
Aquanova AG
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 Aquanova AG filed Critical Aquanova AG
Priority to US11/329,173 priority Critical patent/US20060116510A1/en
Publication of US20060116510A1 publication Critical patent/US20060116510A1/en
Assigned to AQUANOVA AG reassignment AQUANOVA AG CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: AQUANOVA GERMAN SOLUBILISATE TECHNOLOGIES (AGT) GMBH
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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]
    • 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]
    • A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
    • 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]
    • A01N65/20—Fabaceae or Leguminosae [Pea or Legume family], e.g. pea, lentil, soybean, clover, acacia, honey locust, derris or millettia
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • 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)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A61K36/286—Carthamus (distaff thistle)
    • 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)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • 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)
    • A61K36/55—Linaceae (Flax family), e.g. Linum
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/30—Oestrogens
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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 isoflavone concentrates, as well as to a method for their production.
  • Hormones are chemical compounds that are synthesized in special organs or cells, and are then transported to a different location in order to coordinate growth, development, and physiological-metabolical performances at a very low concentration.
  • Plants contain compounds that have no hormonal character for the same, which produce hormone-similar effects in the mammal, however.
  • the one known best are the so-called isoflavones from legumes.
  • soy contains genistein, isogenistein, and formononetine.
  • These agents have estrogen effects, and therefore have a very positive influence on post-menopausal symptoms, such as problems with blood circulation, type II diabetes, and osteoporosis, inevitably without any side effects. In this way, they indirectly influence the mortality rate.
  • General ageing phenomena, such as of the skin are also part of this circle of protective qualities. For decades the average isoflavone absorption in Asia has been between 20 and 100 mg/day; it is much less than that in Western countries.
  • Isoflavones of the type genistein are contained in soy, and in many other plants.
  • Nutrition based on soy which is common mainly in Asia, is attributed to the fact that much less carcinomas (breast, prostate, skin) occur there, and that post-menopausal symptoms in women occur rarely.
  • Isoflavones are so-called phytoestrogens, and bind to the estradiol receptor. With animal tests and skin models, it was found that these isoflavones increase the intracellular, enzymatic, antioxydative potential. This is in part due to its effect.
  • the invention is therefore based on the task of increasing the bio-availability and resorption of the mentioned agents on one hand, and of easing the incorporation of these agents into the end products in the food, cosmetics, and pharmaceutical industries on the other hand.
  • the invention provides an isoflavone concentrate that contains a polysorbate, as well as one or more of the agents genistein, daidcein, glycitein, and/or their glycosides.
  • the concentrate according to the invention is soluble in water as a clear solution. When this solution is administered, the isoflavones of the type genistein are slightly resorbed in the gastrointestinal tract. It is therefore possible to add a dosage of the concentrate according to the invention to alcohol-free beverage with the result that the general isoflavone absorption of the organism is quasi casually and simultaneously increased with the consumption of beverages.
  • Isoflavones of the type genisetin in the form of a water soluble concentrate can be used in the classical food industry, and advantageously in the cosmetics or skin care industries.
  • the water solubility ensures a substantially higher absorption of the isoflavones through the skin.
  • Agents of a purely vegetable origin are preferred. It is recommended for an agent concentrate containing isoflavone, to generally use a powder processed soybean extract, which contains 400 g of a mixture of genistin, daidcin, and glycitin, as well as their aglycons per kilogram.
  • the quantity ratio of genistin, daidcin, and glycitin would then be about 1.3:1.0:0.3.
  • polysorbate 80 is used for the production of the concentrate according to the invention.
  • polysorbate 20, polysorbate 40, polysorbate 60, and polysorbate 65 are also suitable, which are obtained from sorbitol as the partial ester of lauric, palmitic, or stearic acid.
  • the object of the invention therefore also includes liqueurs, various foods, and also skin care products, cosmetics, and such products that contain an isoflavone concentrate of polysorbate, and one or more of the agents genistein, daidcein, glycitein, and/or their glycosides.
  • a beverage for instance, contains approximately 0.5 g to approximately 3 g of isoflavone concentrate per liter.
  • This water-free concentrate can be packaged undiluted into gelatin and/or gelatin-free capsules as antioxidants, or dietary supplements.
  • soybean extract powder For the production of a water-soluble concentrate containing isoflavones, for instance, 100 g of soybean extract powder is used as the base product, which is distributed by Archer-Daniels-Midland Company, USA under the brand name NOVASOY.
  • This soybean extract contains at least 40 wt-% of genistin, daidcin, and glycitin, and their aglycons at a quantity ratio of 1.3:1.0:0.3.
  • 100 g of the said extract therefore contain 20.0 g of genistin, 15.4 g of daidcin, and 4.6 g of glycitin, a total of 40.0 g of isoflavones.
  • this concentrate contains approximately 66 g of isoflavone.
  • this beverage then contains about 100 mg of the said isoflavone so that one liter of a finished beverage processed in this way sufficiently covers the daily requirement of isoflavone.
  • soy extracts of other sources can also be used, which are distinguished by their substantial lack of sugar.
  • K.-W. Pfannenschmidt GmbH Hamburg, supplies a soybean extract that has a total isoflavone content of at least 40%. This approximately 40% is comprised of 7.58% of genistin, 25.43% of genistein, 5.48% of daidcin, and 1.67% of daidcein. Approximately the same results are achieved, if this soybean extract is processes as described in connection with NOVASOY.
  • the extraction of the watery isoflavone concentrate according to the invention provides that the named compounds are trickled into water that has been heated to approximately 60° C., and the mixture is stirred at the said temperature during a predetermined time period of about ten minutes. Polysorbate is then added to the mixture, and the temperature is increased to about 100° C. The stirring process is continued at this temperature until-the mixture has turned clear and transparent. Alternatively, polysorbate can first be added to the compounds, and then the water can be added.
  • 100 g of the mentioned soybean extract NOVASOY is evenly stirred into 400 g of distilled water that has previously been heated to approximately 60° C. the mixture (total quantity 500 g) is consistently stirred using a magnetic stirrer while maintaining the temperature of about 60° C. for about ten minutes. While continuing the stirring process, 500 g of polysorbate 80 is added, and the temperature is increased to approximately 100° C.
  • the water quantity to be added according to the following example 3 can be compensated, or reduced partially by adding triglycerides, or a light vegetable oil (such as safflower oil).
  • the weight ratio of NOVASOY to polysorbate 80 should be selected at about 1:6 in this case, while it is about 1:5 in the previous examples.
  • 100 g of the mentioned soybean extract NOVASOY is evenly stirred into 230 g of distilled water that has been heated to about 60° C.
  • the mixture (total quantity 330 g) is consistently stirred with a magnetic stirrer while maintaining the temperature at about 60° C. for approximately five minutes. While the stirring process is continued, and the temperature is maintained, about 70 g of vegetable oil (safflower oil) is added, and stirred for approximately five minutes. Subsequently, 600 g of polysorbate 80 is added to the mixture (400 g), and the temperature is increased to approximately 100° C. The stirring process is continued at this temperature until the mixture (total quantity 1 kg) has turned transparent, or results in a clear, brownish solution dissolved in water. This clear mixture contains the incorporated 40 g of isoflavone.
  • safflower oil sunflower oil, linseed oil, soy oil, or olive oil can also be used. All of these oils distinguish themselves by a high content of triglycerides, such as ⁇ -linolenic acid, ⁇ -linolenic acid, linoleic acid, or oleic acid.
  • triglyceride-rich oils preferably of vegetable origin, may be used instead of safflower oil.
  • the stability of the concentrate according to the invention in its clarity and water solubility is given also if gastric acid is added to the concentrate according to the invention, or to a preparation produced from it (i.e. a beverage). This is true also if the concentrate is heated, for instance, to about 100° C. The concentrate also distinguishes itself by an excellent stability.
  • Micells are present in the isoflavone concentrates according to the invention, the interiors of which contain isoflavones, which are surrounded by polysorbate molecules.
  • the median radius of the micells is below 20 nm.
  • the 4% isoflavone concentrate resulting in example 2 is diluted in water at a ratio of 1:200, and the 0.02% isoflavone concentrate dilution achieved in this way is submitted to the field/flow fractionation with downstreamed DAWN-EOS detector according to Wyatt technology. The result is reflected in the attached diagram, according to which curve 1 states an R.M.S. radius of the sample of about 16 nm.
  • Curve 2 is a reference curve.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Mycology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Birds (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Diabetes (AREA)
  • Nutrition Science (AREA)
  • Endocrinology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Dermatology (AREA)

Abstract

Isoflavone concentrates are described, which contain at least about ten to about twenty weight parts of polysorbate to one weight part of isoflavone containing a genistein, and/or daidcein, and/or glycitein. Further, a method for the production of an isoflavone concentrate is described.

Description

  • The invention relates to isoflavone concentrates, as well as to a method for their production.
  • Hormones are chemical compounds that are synthesized in special organs or cells, and are then transported to a different location in order to coordinate growth, development, and physiological-metabolical performances at a very low concentration.
  • Plants contain compounds that have no hormonal character for the same, which produce hormone-similar effects in the mammal, however. The one known best are the so-called isoflavones from legumes. For instance, soy contains genistein, isogenistein, and formononetine. These agents have estrogen effects, and therefore have a very positive influence on post-menopausal symptoms, such as problems with blood circulation, type II diabetes, and osteoporosis, fortunately without any side effects. In this way, they indirectly influence the mortality rate. General ageing phenomena, such as of the skin, are also part of this circle of protective qualities. For decades the average isoflavone absorption in Asia has been between 20 and 100 mg/day; it is much less than that in Western countries.
  • Isoflavones of the type genistein are contained in soy, and in many other plants. Nutrition based on soy, which is common mainly in Asia, is attributed to the fact that much less carcinomas (breast, prostate, skin) occur there, and that post-menopausal symptoms in women occur rarely. Isoflavones are so-called phytoestrogens, and bind to the estradiol receptor. With animal tests and skin models, it was found that these isoflavones increase the intracellular, enzymatic, antioxydative potential. This is in part due to its effect.
  • The invention is therefore based on the task of increasing the bio-availability and resorption of the mentioned agents on one hand, and of easing the incorporation of these agents into the end products in the food, cosmetics, and pharmaceutical industries on the other hand.
  • For this purpose, the invention provides an isoflavone concentrate that contains a polysorbate, as well as one or more of the agents genistein, daidcein, glycitein, and/or their glycosides. The concentrate according to the invention is soluble in water as a clear solution. When this solution is administered, the isoflavones of the type genistein are slightly resorbed in the gastrointestinal tract. It is therefore possible to add a dosage of the concentrate according to the invention to alcohol-free beverage with the result that the general isoflavone absorption of the organism is quasi casually and simultaneously increased with the consumption of beverages. Isoflavones of the type genisetin in the form of a water soluble concentrate can be used in the classical food industry, and advantageously in the cosmetics or skin care industries. The water solubility ensures a substantially higher absorption of the isoflavones through the skin.
  • Agents of a purely vegetable origin are preferred. It is recommended for an agent concentrate containing isoflavone, to generally use a powder processed soybean extract, which contains 400 g of a mixture of genistin, daidcin, and glycitin, as well as their aglycons per kilogram. Advantageously, the quantity ratio of genistin, daidcin, and glycitin would then be about 1.3:1.0:0.3.
  • Preferably, polysorbate 80 is used for the production of the concentrate according to the invention. For the use according to the purpose of the invention, polysorbate 20, polysorbate 40, polysorbate 60, and polysorbate 65 are also suitable, which are obtained from sorbitol as the partial ester of lauric, palmitic, or stearic acid.
  • In addition to non-alcoholic beverages, the object of the invention therefore also includes liqueurs, various foods, and also skin care products, cosmetics, and such products that contain an isoflavone concentrate of polysorbate, and one or more of the agents genistein, daidcein, glycitein, and/or their glycosides. Purposefully, a beverage, for instance, contains approximately 0.5 g to approximately 3 g of isoflavone concentrate per liter. This water-free concentrate can be packaged undiluted into gelatin and/or gelatin-free capsules as antioxidants, or dietary supplements.
  • For the production of a water-soluble concentrate containing isoflavones, for instance, 100 g of soybean extract powder is used as the base product, which is distributed by Archer-Daniels-Midland Company, USA under the brand name NOVASOY. This soybean extract contains at least 40 wt-% of genistin, daidcin, and glycitin, and their aglycons at a quantity ratio of 1.3:1.0:0.3. 100 g of the said extract therefore contain 20.0 g of genistin, 15.4 g of daidcin, and 4.6 g of glycitin, a total of 40.0 g of isoflavones.
  • For example, the said powdered soy extract with the brand name NOVASOY, distributed by Archer-Daniels-Midland Company, Decatur, Ill., USA, serves for the production of a water-free isoflavone concentrate containing isoflavones, which mainly contains the glycosides of genistein, daidcein, and glycitein.
    • EXAMPLE 1
  • Approximately 166 g of this soy extract powder is trickled into approximately 834 g of polysorbate that has been heated to approximately 75° Celsius, and the mixture (1.0 kg) is consistently stirred for about half an hour at this temperature. A deep brown, clear concentrate without sediment is the result. If about 1-2 ml of this concentrate is added to ten times the amount of distilled water, a clear solution is obtained after completion of the mixing process.
  • 1.0 kg of this concentrate contains approximately 66 g of isoflavone. By adding 1.5 g of the concentrate to 1.0 liters of a finished beverage, this beverage then contains about 100 mg of the said isoflavone so that one liter of a finished beverage processed in this way sufficiently covers the daily requirement of isoflavone.
  • Instead of NOVASOY, soy extracts of other sources can also be used, which are distinguished by their substantial lack of sugar. For instance, K.-W. Pfannenschmidt GmbH, Hamburg, supplies a soybean extract that has a total isoflavone content of at least 40%. This approximately 40% is comprised of 7.58% of genistin, 25.43% of genistein, 5.48% of daidcin, and 1.67% of daidcein. Approximately the same results are achieved, if this soybean extract is processes as described in connection with NOVASOY.
  • The preceding describes the production of a water-free agent concentrate. However, it is also possible to achieve a watery agent concentrate according to the following examples:
  • The extraction of the watery isoflavone concentrate according to the invention provides that the named compounds are trickled into water that has been heated to approximately 60° C., and the mixture is stirred at the said temperature during a predetermined time period of about ten minutes. Polysorbate is then added to the mixture, and the temperature is increased to about 100° C. The stirring process is continued at this temperature until-the mixture has turned clear and transparent. Alternatively, polysorbate can first be added to the compounds, and then the water can be added.
    • EXAMPLE 2
  • For example 100 g of the mentioned soybean extract NOVASOY is evenly stirred into 400 g of distilled water that has previously been heated to approximately 60° C. the mixture (total quantity 500 g) is consistently stirred using a magnetic stirrer while maintaining the temperature of about 60° C. for about ten minutes. While continuing the stirring process, 500 g of polysorbate 80 is added, and the temperature is increased to approximately 100° C.
  • The stirring process is continued at this temperature until the mixture (total quantity 1 kg) has turned clear and transparent. This clear mixture contains the incorporated 40 g of isoflavone.
  • If a water-soluble isoflavone concentrate is desired to contain less water specifically to the end product, the water quantity to be added according to the following example 3 can be compensated, or reduced partially by adding triglycerides, or a light vegetable oil (such as safflower oil). The weight ratio of NOVASOY to polysorbate 80 should be selected at about 1:6 in this case, while it is about 1:5 in the previous examples.
    • Example 3
  • 100 g of the mentioned soybean extract NOVASOY is evenly stirred into 230 g of distilled water that has been heated to about 60° C. The mixture (total quantity 330 g) is consistently stirred with a magnetic stirrer while maintaining the temperature at about 60° C. for approximately five minutes. While the stirring process is continued, and the temperature is maintained, about 70 g of vegetable oil (safflower oil) is added, and stirred for approximately five minutes. Subsequently, 600 g of polysorbate 80 is added to the mixture (400 g), and the temperature is increased to approximately 100° C. The stirring process is continued at this temperature until the mixture (total quantity 1 kg) has turned transparent, or results in a clear, brownish solution dissolved in water. This clear mixture contains the incorporated 40 g of isoflavone.
  • 2.5 g of this clear, stable watery concentrate contain 100 mg of isoflavone. This quantity, for instance, can be incorporated into one liter of a finished beverage, which thereby covers twice the daily requirement of an amount of 50 mg of isoflavone.
  • Instead of safflower oil, sunflower oil, linseed oil, soy oil, or olive oil can also be used. All of these oils distinguish themselves by a high content of triglycerides, such as α-linolenic acid, γ-linolenic acid, linoleic acid, or oleic acid. For example, safflower oil contains up to 83% of linoleic acid, and up to 24% of oleic acid; linseed oil contains up to 71% of linolenic acid, up to 31% of linoleic acid, and up to 23% of oleic acid. Therefore, one or more triglyceride-rich oils, preferably of vegetable origin, may be used instead of safflower oil.
  • In order to accelerate and optimize the mixing process and the solubility, it is recommended to heat the isoflavone concentrates according to examples 1 to 3 to approximately 70° C. before the mixing process, and the water, in which the concentrate is to be dissolved, to approximately 40° C., also before the mixing process.
  • The stability of the concentrate according to the invention in its clarity and water solubility is given also if gastric acid is added to the concentrate according to the invention, or to a preparation produced from it (i.e. a beverage). This is true also if the concentrate is heated, for instance, to about 100° C. The concentrate also distinguishes itself by an excellent stability.
  • Micells are present in the isoflavone concentrates according to the invention, the interiors of which contain isoflavones, which are surrounded by polysorbate molecules. The median radius of the micells is below 20 nm. As a verification, the 4% isoflavone concentrate resulting in example 2 is diluted in water at a ratio of 1:200, and the 0.02% isoflavone concentrate dilution achieved in this way is submitted to the field/flow fractionation with downstreamed DAWN-EOS detector according to Wyatt technology. The result is reflected in the attached diagram, according to which curve 1 states an R.M.S. radius of the sample of about 16 nm. Curve 2 is a reference curve.
    Figure US20060116510A1-20060601-P00001

Claims (12)

1-16. (canceled)
17. An isoflavonoid concentrate containing a polysorbate and a mixture comprising genistein, daidzen, glyceiten, and their glycosides.
18. The isoflavonoid concentrate of claim 17, wherein said concentrate contains approximately 83.4% by weight of polysorbate 80 and approximately 6.64% by weight of said mixture.
19. The isoflavonoid concentrate of claim 17, wherein said concentrate contains approximately 50% by weight of polysorbate 80, approximately 40% by weight of water and approximately 4% by weight of said mixture.
20. The isoflavonoid concentrate of claim 17, wherein said concentrate contains approximately 60% by weight of polysorbate 80, approximately 23% by weight of water, approximately 7% by weight of triglyceride containing plant oil, and approximately 4% by weight of said mixture.
21. The isoflavonoid concentrate of claim 17, wherein said polysorbate is polysorbate 80.
22. A finished drink comprising approximately 15% by weight or 25% by weight of the concentrate of claim 17.
23. A finished drink comprising approximately 15% by weight or 25% by weight of the concentrate of claim 18.
24. A finished drink comprising approximately 15% by weight or 25% by weight of the concentrate of claim 19.
25. A finished drink comprising approximately 15% by weight or 25% by weight of the concentrate of claim 20.
26. A finished drink comprising approximately 15% by weight or 25% by weight of the concentrate of claim 21.
27. Use of the isoflavonoid concentrate of claim 17 in cosmetics, nutritional supplements, or body care products.
US11/329,173 2002-06-29 2006-01-11 Isoflavone concentrates, as well as methods for their production Abandoned US20060116510A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/329,173 US20060116510A1 (en) 2002-06-29 2006-01-11 Isoflavone concentrates, as well as methods for their production

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/450,539 US7208594B2 (en) 2002-06-29 2002-06-29 Isoflavone concentrates as well as methods for their production
PCT/EP2002/007194 WO2004002469A1 (en) 2002-06-29 2002-06-29 Isoflavone concentrate and method for production thereof
US11/329,173 US20060116510A1 (en) 2002-06-29 2006-01-11 Isoflavone concentrates, as well as methods for their production

Related Parent Applications (3)

Application Number Title Priority Date Filing Date
US10/469,541 Division US7155097B2 (en) 2001-03-09 2002-03-09 Fabrication of microstructured fibres
US10/450,539 Division US7208594B2 (en) 2002-06-29 2002-06-29 Isoflavone concentrates as well as methods for their production
PCT/EP2002/007194 Division WO2004002469A1 (en) 2002-06-29 2002-06-29 Isoflavone concentrate and method for production thereof

Publications (1)

Publication Number Publication Date
US20060116510A1 true US20060116510A1 (en) 2006-06-01

Family

ID=29797108

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/450,539 Expired - Fee Related US7208594B2 (en) 2002-06-29 2002-06-29 Isoflavone concentrates as well as methods for their production
US11/329,173 Abandoned US20060116510A1 (en) 2002-06-29 2006-01-11 Isoflavone concentrates, as well as methods for their production

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US10/450,539 Expired - Fee Related US7208594B2 (en) 2002-06-29 2002-06-29 Isoflavone concentrates as well as methods for their production

Country Status (12)

Country Link
US (2) US7208594B2 (en)
EP (1) EP1450786B1 (en)
JP (1) JP2005531616A (en)
AT (1) ATE312605T1 (en)
AU (1) AU2002328824A1 (en)
CA (1) CA2448513A1 (en)
DE (1) DE50205310D1 (en)
DK (1) DK1450786T3 (en)
ES (1) ES2254725T3 (en)
IL (2) IL158569A0 (en)
MX (1) MXPA04002145A (en)
WO (1) WO2004002469A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8551530B2 (en) 2010-11-15 2013-10-08 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US9084726B2 (en) 2013-11-26 2015-07-21 Humanetics Corporation Suspension compositions of physiologically active phenolic compounds and methods of making and using the same

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005320281A (en) * 2004-05-10 2005-11-17 Shiratori Pharmaceutical Co Ltd Promotor of insulin secretion and food and drink
EP1904042A2 (en) * 2005-07-08 2008-04-02 Aquanova Ag Solubilsation products of an active ingredient extract
CN101330902A (en) * 2005-12-13 2008-12-24 宝洁公司 Personal care compositions comprising PPAR GAMMA antagonists
US20100120904A1 (en) * 2007-04-02 2010-05-13 Kevin Prudence Novel use of genistein
AU2010308571B2 (en) 2009-10-22 2016-10-13 Tpc-Api Llc Methods of making and using compositions comprising flavonoids
US8637569B2 (en) 2009-10-22 2014-01-28 Api Genesis, Llc Methods of increasing solubility of poorly soluble compounds and methods of making and using formulations of such compounds

Citations (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172128A (en) * 1975-03-26 1979-10-23 Erhard Thiele Process of degrading and regenerating bone and tooth material and products
US4563350A (en) * 1984-10-24 1986-01-07 Collagen Corporation Inductive collagen based bone repair preparations
US5563046A (en) * 1993-08-02 1996-10-08 Celtrix Pharmaceuticals, Inc. Fusion polypeptides and proteins
US5608035A (en) * 1994-02-02 1997-03-04 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5635597A (en) * 1994-05-27 1997-06-03 Affymax Technologies, N.V. Peptides that bind IL-2 receptors
US5643873A (en) * 1992-05-06 1997-07-01 Affymax Technologies N.V. Peptides and compounds that bind selectins including endothelial leukocyte adhesion molecule 1
US5648458A (en) * 1992-05-06 1997-07-15 Affymax Technologies N.V. Peptides and compounds that bind to ELAM-1
US5654276A (en) * 1995-06-07 1997-08-05 Affymax Technologies N.V. Peptides and compounds that bind to the IL-5 receptor
US5668110A (en) * 1995-06-07 1997-09-16 Affymax Technologies N.V. Peptides and compounds that bind to the IL-5 receptor
US5674977A (en) * 1993-02-05 1997-10-07 The Ontario Cancer Institute Branched synthetic peptide conjugate
US5679637A (en) * 1989-04-27 1997-10-21 The Salk Institute For Biological Studies Fibroblast growth factor conjugates
US5679673A (en) * 1992-09-24 1997-10-21 The United States Of America, Represented By The Department Of Health And Human Services Aralkyl bridged diazabicycloalkane derivatives for CNS disorders
US5684136A (en) * 1992-05-18 1997-11-04 Genentech, Inc. Chimeric hepatocyte growth factor (HGF) ligand variants
US5728802A (en) * 1992-05-06 1998-03-17 Affymax Technologies N.V. Peptides and compounds that bind selectins including endothelium leukocyte adhesion molecule 1 (ELAM-1)
US5759515A (en) * 1989-08-09 1998-06-02 Rhomed Incorporated Polyvalent peptide pharmaceutical applications
US5770704A (en) * 1992-05-18 1998-06-23 Genentech, Inc. Receptor activation with inactive hepatocyte growth factor ligands
US5773569A (en) * 1993-11-19 1998-06-30 Affymax Technologies N.V. Compounds and peptides that bind to the erythropoietin receptor
US5786331A (en) * 1994-02-02 1998-07-28 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5789182A (en) * 1990-12-20 1998-08-04 The Children's Medical Center Corporation System for assaying binding to a heparin-binding growth factor receptor
US5824702A (en) * 1996-06-07 1998-10-20 Mount Sinai School Of Medicine Of The City University Of New York Genistein as a preventive against ultraviolet induced skin photodamage and cancer
US5830851A (en) * 1993-11-19 1998-11-03 Affymax Technologies N.V. Methods of administering peptides that bind to the erythropoietin receptor
US5861476A (en) * 1994-02-02 1999-01-19 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5866113A (en) * 1996-05-31 1999-02-02 Medtronic, Inc. Medical device with biomolecule-coated surface graft matrix
US5869451A (en) * 1995-06-07 1999-02-09 Glaxo Group Limited Peptides and compounds that bind to a receptor
US5880096A (en) * 1994-02-02 1999-03-09 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5902799A (en) * 1989-04-23 1999-05-11 The Trustees Of The University Of Pennsylvania Methods of modulating tissue growth and regeneration
US5932462A (en) * 1995-01-10 1999-08-03 Shearwater Polymers, Inc. Multiarmed, monofunctional, polymer for coupling to molecules and surfaces
US5952474A (en) * 1992-08-28 1999-09-14 The Public Health Research Institute Of The City Of New York, Inc. Fusion glycoproteins
US5955588A (en) * 1997-12-22 1999-09-21 Innerdyne, Inc. Non-thrombogenic coating composition and methods for using same
US5965532A (en) * 1996-06-28 1999-10-12 Trustees Of Tufts College Multivalent compounds for crosslinking receptors and uses thereof
US5989866A (en) * 1996-10-16 1999-11-23 Zymogenetics, Inc. FGF homologs
US5994104A (en) * 1996-11-08 1999-11-30 Royal Free Hospital School Of Medicine Interleukin-12 fusion protein
US6001364A (en) * 1993-05-05 1999-12-14 Gryphon Sciences Hetero-polyoxime compounds and their preparation by parallel assembly
US6011002A (en) * 1994-04-08 2000-01-04 The United States Of America As Represented By The Department Of Health And Human Services Circularly permuted ligands and circularly permuted chimeric molecules
US6030812A (en) * 1992-11-24 2000-02-29 G. D. Searle & Company Fusion proteins comprising multiply mutated interleukin-3 (IL-3) polypeptides and second growth factors
US6051648A (en) * 1995-12-18 2000-04-18 Cohesion Technologies, Inc. Crosslinked polymer compositions and methods for their use
US6096343A (en) * 1997-10-27 2000-08-01 Gerhard Gergely Instant calcium/soybean granules, their use and process for their preparation
US6121236A (en) * 1998-03-24 2000-09-19 The Children's Medical Center Corporation Multivalent ligands which modulate angiogenesis
US6168784B1 (en) * 1997-09-03 2001-01-02 Gryphon Sciences N-terminal modifications of RANTES and methods of use
US6174530B1 (en) * 1993-05-05 2001-01-16 Gryphon Sciences Homogeneous polyoxime compositions and their preparation by parallel assembly
US6174721B1 (en) * 1994-08-05 2001-01-16 Chiron Corporation Chimeric proteins
US6214795B1 (en) * 1996-11-12 2001-04-10 Praecis Pharmaceuticals, Inc. Peptide compounds useful for modulating FGF receptor activity
US6251864B1 (en) * 1995-06-07 2001-06-26 Glaxo Group Limited Peptides and compounds that bind to a receptor
US6261565B1 (en) * 1996-03-13 2001-07-17 Archer Daniels Midland Company Method of preparing and using isoflavones
US6284503B1 (en) * 1993-08-20 2001-09-04 University Of Utah Research Foundation Composition and method for regulating the adhesion of cells and biomolecules to hydrophobic surfaces
US6294359B1 (en) * 1985-09-12 2001-09-25 Scios Inc. Human basic fibroblast growth factor analog
US6300377B1 (en) * 2001-02-22 2001-10-09 Raj K. Chopra Coenzyme Q products exhibiting high dissolution qualities
US6323323B1 (en) * 1988-01-22 2001-11-27 Zymogenetics, Inc. Ligand-binding, dimerized polypeptide fusions
US6326468B1 (en) * 1997-06-13 2001-12-04 Gryphon Sciences Solid phase native chemical ligation of unprotected or n-terminal cysteine protected peptides in aqueous solution
US6342591B1 (en) * 1998-09-22 2002-01-29 Biosurface Engineering Technologies, Inc. Amphipathic coating for modulating cellular adhesion composition and methods
US6350731B1 (en) * 1993-10-22 2002-02-26 Trigen Limited Platelet-derived growth factor analogues
US6377349B1 (en) * 1998-03-30 2002-04-23 Carl Zeiss Jena Gmbh Arrangement for spectral interferometric optical tomography and surface profile measurement
US6451543B1 (en) * 1998-08-31 2002-09-17 Gryphon Sciences Lipid matrix-assisted chemical ligation and synthesis of membrane polypeptides
US6495718B1 (en) * 1999-05-26 2002-12-17 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Method for suppressing sorbate- and/or sorbic acid-induced discoloration
US20030224996A1 (en) * 1988-04-08 2003-12-04 Stryker Corporation Osteogenic devices

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2010894A1 (en) 1989-02-28 1990-08-31 Isamu Horikoshi Method of forming a suspension and composition formed by said method
US6251420B1 (en) 1998-01-28 2001-06-26 Dusan Miljkovic Isoflavanoid formulations for oral administration
DE10104847B4 (en) 2000-06-09 2006-12-21 Aquanova German Solubilisate Technologies (Agt) Gmbh Tocopherol concentrate and process for its preparation
DE10103454A1 (en) 2000-12-29 2002-08-01 Aquanova Getraenketechnologie Flavonoid concentrate useful in foods, body care products and cosmetics comprises a polysorbate and isoflavones and/or quercetin
US20040081670A1 (en) 2001-02-11 2004-04-29 Dariush Behnam Method for producing an active ingredient concentrate, and an active ingredient concentrate

Patent Citations (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172128A (en) * 1975-03-26 1979-10-23 Erhard Thiele Process of degrading and regenerating bone and tooth material and products
US4563350A (en) * 1984-10-24 1986-01-07 Collagen Corporation Inductive collagen based bone repair preparations
US6294359B1 (en) * 1985-09-12 2001-09-25 Scios Inc. Human basic fibroblast growth factor analog
US6323323B1 (en) * 1988-01-22 2001-11-27 Zymogenetics, Inc. Ligand-binding, dimerized polypeptide fusions
US20030224996A1 (en) * 1988-04-08 2003-12-04 Stryker Corporation Osteogenic devices
US5902799A (en) * 1989-04-23 1999-05-11 The Trustees Of The University Of Pennsylvania Methods of modulating tissue growth and regeneration
US5679637A (en) * 1989-04-27 1997-10-21 The Salk Institute For Biological Studies Fibroblast growth factor conjugates
US5759515A (en) * 1989-08-09 1998-06-02 Rhomed Incorporated Polyvalent peptide pharmaceutical applications
US5789182A (en) * 1990-12-20 1998-08-04 The Children's Medical Center Corporation System for assaying binding to a heparin-binding growth factor receptor
US5648458A (en) * 1992-05-06 1997-07-15 Affymax Technologies N.V. Peptides and compounds that bind to ELAM-1
US5786322A (en) * 1992-05-06 1998-07-28 Affymax Technologies N.V. Peptides and compounds that bind selectins including endothelium leukocyte adhesion molecule 1
US5728802A (en) * 1992-05-06 1998-03-17 Affymax Technologies N.V. Peptides and compounds that bind selectins including endothelium leukocyte adhesion molecule 1 (ELAM-1)
US5643873A (en) * 1992-05-06 1997-07-01 Affymax Technologies N.V. Peptides and compounds that bind selectins including endothelial leukocyte adhesion molecule 1
US5770704A (en) * 1992-05-18 1998-06-23 Genentech, Inc. Receptor activation with inactive hepatocyte growth factor ligands
US5684136A (en) * 1992-05-18 1997-11-04 Genentech, Inc. Chimeric hepatocyte growth factor (HGF) ligand variants
US5952474A (en) * 1992-08-28 1999-09-14 The Public Health Research Institute Of The City Of New York, Inc. Fusion glycoproteins
US5679673A (en) * 1992-09-24 1997-10-21 The United States Of America, Represented By The Department Of Health And Human Services Aralkyl bridged diazabicycloalkane derivatives for CNS disorders
US6030812A (en) * 1992-11-24 2000-02-29 G. D. Searle & Company Fusion proteins comprising multiply mutated interleukin-3 (IL-3) polypeptides and second growth factors
US5674977A (en) * 1993-02-05 1997-10-07 The Ontario Cancer Institute Branched synthetic peptide conjugate
US6001364A (en) * 1993-05-05 1999-12-14 Gryphon Sciences Hetero-polyoxime compounds and their preparation by parallel assembly
US6217873B1 (en) * 1993-05-05 2001-04-17 Gryphon Sciences Polyoxime compounds and their preparation
US6174530B1 (en) * 1993-05-05 2001-01-16 Gryphon Sciences Homogeneous polyoxime compositions and their preparation by parallel assembly
US5563046A (en) * 1993-08-02 1996-10-08 Celtrix Pharmaceuticals, Inc. Fusion polypeptides and proteins
US6284503B1 (en) * 1993-08-20 2001-09-04 University Of Utah Research Foundation Composition and method for regulating the adhesion of cells and biomolecules to hydrophobic surfaces
US6350731B1 (en) * 1993-10-22 2002-02-26 Trigen Limited Platelet-derived growth factor analogues
US5773569A (en) * 1993-11-19 1998-06-30 Affymax Technologies N.V. Compounds and peptides that bind to the erythropoietin receptor
US5830851A (en) * 1993-11-19 1998-11-03 Affymax Technologies N.V. Methods of administering peptides that bind to the erythropoietin receptor
US5880096A (en) * 1994-02-02 1999-03-09 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5786331A (en) * 1994-02-02 1998-07-28 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5608035A (en) * 1994-02-02 1997-03-04 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5861476A (en) * 1994-02-02 1999-01-19 Affymax Technologies N.V. Peptides and compounds that bind to the IL-1 receptor
US5767234A (en) * 1994-02-02 1998-06-16 Affymax Technologies, N.V. Peptides and compounds that bind to the IL-1 receptor
US6011002A (en) * 1994-04-08 2000-01-04 The United States Of America As Represented By The Department Of Health And Human Services Circularly permuted ligands and circularly permuted chimeric molecules
US5635597A (en) * 1994-05-27 1997-06-03 Affymax Technologies, N.V. Peptides that bind IL-2 receptors
US6174721B1 (en) * 1994-08-05 2001-01-16 Chiron Corporation Chimeric proteins
US5932462A (en) * 1995-01-10 1999-08-03 Shearwater Polymers, Inc. Multiarmed, monofunctional, polymer for coupling to molecules and surfaces
US5668110A (en) * 1995-06-07 1997-09-16 Affymax Technologies N.V. Peptides and compounds that bind to the IL-5 receptor
US6251864B1 (en) * 1995-06-07 2001-06-26 Glaxo Group Limited Peptides and compounds that bind to a receptor
US5654276A (en) * 1995-06-07 1997-08-05 Affymax Technologies N.V. Peptides and compounds that bind to the IL-5 receptor
US5869451A (en) * 1995-06-07 1999-02-09 Glaxo Group Limited Peptides and compounds that bind to a receptor
US6051648A (en) * 1995-12-18 2000-04-18 Cohesion Technologies, Inc. Crosslinked polymer compositions and methods for their use
US6261565B1 (en) * 1996-03-13 2001-07-17 Archer Daniels Midland Company Method of preparing and using isoflavones
US5866113A (en) * 1996-05-31 1999-02-02 Medtronic, Inc. Medical device with biomolecule-coated surface graft matrix
US5824702A (en) * 1996-06-07 1998-10-20 Mount Sinai School Of Medicine Of The City University Of New York Genistein as a preventive against ultraviolet induced skin photodamage and cancer
US5965532A (en) * 1996-06-28 1999-10-12 Trustees Of Tufts College Multivalent compounds for crosslinking receptors and uses thereof
US5989866A (en) * 1996-10-16 1999-11-23 Zymogenetics, Inc. FGF homologs
US5994104A (en) * 1996-11-08 1999-11-30 Royal Free Hospital School Of Medicine Interleukin-12 fusion protein
US6214795B1 (en) * 1996-11-12 2001-04-10 Praecis Pharmaceuticals, Inc. Peptide compounds useful for modulating FGF receptor activity
US6326468B1 (en) * 1997-06-13 2001-12-04 Gryphon Sciences Solid phase native chemical ligation of unprotected or n-terminal cysteine protected peptides in aqueous solution
US6168784B1 (en) * 1997-09-03 2001-01-02 Gryphon Sciences N-terminal modifications of RANTES and methods of use
US6096343A (en) * 1997-10-27 2000-08-01 Gerhard Gergely Instant calcium/soybean granules, their use and process for their preparation
US5955588A (en) * 1997-12-22 1999-09-21 Innerdyne, Inc. Non-thrombogenic coating composition and methods for using same
US6235716B1 (en) * 1998-03-24 2001-05-22 Children's Medical Center Corporation Multivalent ligands which modulate angiogenesis
US6121236A (en) * 1998-03-24 2000-09-19 The Children's Medical Center Corporation Multivalent ligands which modulate angiogenesis
US6377349B1 (en) * 1998-03-30 2002-04-23 Carl Zeiss Jena Gmbh Arrangement for spectral interferometric optical tomography and surface profile measurement
US6451543B1 (en) * 1998-08-31 2002-09-17 Gryphon Sciences Lipid matrix-assisted chemical ligation and synthesis of membrane polypeptides
US6342591B1 (en) * 1998-09-22 2002-01-29 Biosurface Engineering Technologies, Inc. Amphipathic coating for modulating cellular adhesion composition and methods
US6495718B1 (en) * 1999-05-26 2002-12-17 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Method for suppressing sorbate- and/or sorbic acid-induced discoloration
US6300377B1 (en) * 2001-02-22 2001-10-09 Raj K. Chopra Coenzyme Q products exhibiting high dissolution qualities

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8551530B2 (en) 2010-11-15 2013-10-08 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US8900635B2 (en) 2010-11-15 2014-12-02 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US9308167B2 (en) 2010-11-15 2016-04-12 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US9636322B2 (en) 2010-11-15 2017-05-02 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US9724325B2 (en) 2010-11-15 2017-08-08 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US10039739B2 (en) 2010-11-15 2018-08-07 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US10729674B2 (en) 2010-11-15 2020-08-04 Humanetics Corporation Nanoparticle isoflavone compositions and methods of making and using the same
US9084726B2 (en) 2013-11-26 2015-07-21 Humanetics Corporation Suspension compositions of physiologically active phenolic compounds and methods of making and using the same
US9387171B2 (en) 2013-11-26 2016-07-12 Humanetics Corporation Suspension compositions of physiologically active phenolic compounds and methods of making and using the same
US9782384B2 (en) 2013-11-26 2017-10-10 Humanetics Corporation Suspension compositions of physiologically active phenolic compounds and methods of making and using the same
US9937148B2 (en) 2013-11-26 2018-04-10 Humanetics Corporation Suspension compositions of physiologically active phenolic compounds and methods of making and using the same
US10314812B2 (en) 2013-11-26 2019-06-11 Humanetics Corporation Suspension compositions of physiologically active phenolic compounds and methods of making and using the same

Also Published As

Publication number Publication date
EP1450786A1 (en) 2004-09-01
IL158569A (en) 2008-12-29
JP2005531616A (en) 2005-10-20
DK1450786T3 (en) 2006-04-18
IL158569A0 (en) 2004-05-12
ES2254725T3 (en) 2006-06-16
EP1450786B1 (en) 2005-12-14
US20040220116A1 (en) 2004-11-04
WO2004002469A1 (en) 2004-01-08
MXPA04002145A (en) 2005-03-07
HK1071512A1 (en) 2005-07-22
ATE312605T1 (en) 2005-12-15
US7208594B2 (en) 2007-04-24
DE50205310D1 (en) 2006-01-19
AU2002328824A1 (en) 2004-01-19
CA2448513A1 (en) 2003-12-29

Similar Documents

Publication Publication Date Title
CN105228470B (en) Vitamin E water-soluble derivative preparation and composition containing the same
Stanisavljević et al. Antioxidant and antiproliferative activity of chokeberry juice phenolics during in vitro simulated digestion in the presence of food matrix
Wollgast et al. Polyphenols in chocolate: is there a contribution to human health?
Fraga et al. Basic biochemical mechanisms behind the health benefits of polyphenols
FI83150B (en) FOERFARANDE FOER FRAMSTAELLNING AV EN FETTKOMPOSITION OCH EN FOEDOPRODUKT, SOM AER LAEMPLIG FOER SMAOBARN.
Montoro et al. Structure–antioxidant activity relationships of flavonoids isolated from different plant species
O'Keefe et al. Soybean nutrition
Tew et al. A diet high in wheat fiber decreases the bioavailability of soybean isoflavones in a single meal fed to women
JP4668553B2 (en) Epigallocatechin dimer and trimer having lipase inhibitory activity and / or antioxidant activity
EP0914111A2 (en) Method for the prevention and treatment of cachexia and anorexia
MXPA06013676A (en) Nutritional formulations.
Benmeziane et al. Composition, bioactive potential and food applications of watermelon (Citrullus lanatus) seeds–a review
US20060116510A1 (en) Isoflavone concentrates, as well as methods for their production
TWI278285B (en) Water-soluble bean-based extracts
US6251420B1 (en) Isoflavanoid formulations for oral administration
CN105072925A (en) A composition for enhancing newborn infant cognitive, brain and/or cns development and method of using same
US5932221A (en) Genistin-enriched fraction from soy meal
JP6762782B2 (en) An acidic composition with excellent stability of the folic acid contained
JP2003153650A (en) Edible oil and fat, and food product using the same
Antoine et al. Impact of pulses, starches and meat on vitamin D and K postprandial responses in mice
HK1071512B (en) Isoflavone concentrate and method for production thereof
US20130302448A1 (en) Phytin aqueous solution and use of said solution for the preparation of a liquid nutritional supplement or a cosmetic composition
Al‐Maqtari et al. Comparative analysis of the nutritional, physicochemical, and bioactive characteristics of Artemisia abyssinica and Artemisia arborescens for the evaluation of their potential as ingredients in functional foods
CN119014530B (en) Nutrient delivery system and preparation method thereof
Mahmood et al. The modest hormonal effects of soy isoflavones: What do we really know? A narrative review

Legal Events

Date Code Title Description
AS Assignment

Owner name: AQUANOVA AG, GERMANY

Free format text: CHANGE OF NAME;ASSIGNOR:AQUANOVA GERMAN SOLUBILISATE TECHNOLOGIES (AGT) GMBH;REEL/FRAME:019353/0674

Effective date: 20061026

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION