CA2249501C - Method of preparing and using isoflavones - Google Patents
Method of preparing and using isoflavones Download PDFInfo
- Publication number
- CA2249501C CA2249501C CA002249501A CA2249501A CA2249501C CA 2249501 C CA2249501 C CA 2249501C CA 002249501 A CA002249501 A CA 002249501A CA 2249501 A CA2249501 A CA 2249501A CA 2249501 C CA2249501 C CA 2249501C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- group
- weight
- acid
- isoflavones
- 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.)
- Expired - Lifetime
Links
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- 235000008696 isoflavones Nutrition 0.000 title claims abstract description 54
- 150000002515 isoflavone derivatives Chemical class 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims description 7
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Abstract
A composition is prepared by extracting phytochemicals from plant matter. This composition is enriched preferably in isoflavones, lignans, saponins, catechins and phenolic acids. Soy is the preferred source of these chemicals; however, other plants may also be used, such as red clover, kudzu, flax, and cocoa. The composition is a dietary supplement for treatment of various cancers, pre- and post-menstrual syndromes, and various other disorders.
Description
ethod of Preparing And Us~onavones This invention relates to compositions extracted from vegetable matter and more particularly to phytochemicals, including saponogenins and saponins, catechins, lignans, phenolie acids, cateehins and isoflavones, and especially those extracted from a family of plants including soy, flax, tea, and cocoa 'and methods of using these compositions as nutritional supplements or food additives.
BACKGROUND
Plant materials are known to contain a number of classes of organic low molecular weight compounds which exert: bioactivity in various animals. Historically, these compounds have been considered to be somewhat non-nutritive; however, recent scientific evidence now suggests these compounds may play an important role in the maintenance of health, in ehemoprevention, and in the mitigation of certain conditions or diseases associated with the circulation of sex hormones, including sleep disorders and vaginal dryness.
Edible plants normally contained in the diet, or materials used as herbal remedies/dietary supplements, may contain collections of structurally related compounds.
These related substances are often unique in their amounts and distribution when compared among various plant sources. The most notable groups of compounds exhibiting bioactivity are knovm as flavonoids, isoflavones, saponins, lignans, alkaloids, catechins and phenolic acids.
Epidemiology studies relating diet to disease suggest that dietary components may predispose populations to reduced risk of certain diseases. Far eastern populations consuming soy have reduced rates of breast, prostate and colon cancers and coronary heart disease, while populations in 1~inland have reduced rates of prostate cancer.
Researchers are just now studying the specific compounds in the diet to understand the basis for the epidemiological observations.
Among the various plants consumed in the diet, several are rich sources of phytochemzcals. Soy products contain high amounts of isoflavones and saponins, Unrefned diet grains include plants such as wheat, psyllium, rice, flax and oats that contain lignans. Cocoa contains catechins and phenolic acids. Certain non-dietary plants are also sources of the same chemical molecules, such as lignans and isoflavones in kudzu root or red Clovers. Isoflavones and lignans act as weak estrvgenie substances. Tea plants are also a rich source of phytochemicals, including catechins and phenolic acids.
Isvflavones can be used alone to treat or prevent breast cancer, prostate cancer, skin cancer, and colon cancer or as mechanism inhibitors. Xsotlavvnes alone may also reduce or prevent various symptoms related to the onset and duration of menopause, including hot flashes and osteoporosis. Isoflavones alone may also be effective in certain cardiovascular applications, including heart disease, reducing cholesterol-lipid levels, modulating angiogenesis, and other vascular effects. Moreover, isoflavones alone have been implicated in reducing headaches, dementia, inflammation, and alcohol abuse, as vvetl as inc~munomodulation.
Lignans alone have ~ been implicated in preventing or treating breast cancer, prostate cancer and colon cancer as well as reducing hot flashes, preventing osteoporosis
BACKGROUND
Plant materials are known to contain a number of classes of organic low molecular weight compounds which exert: bioactivity in various animals. Historically, these compounds have been considered to be somewhat non-nutritive; however, recent scientific evidence now suggests these compounds may play an important role in the maintenance of health, in ehemoprevention, and in the mitigation of certain conditions or diseases associated with the circulation of sex hormones, including sleep disorders and vaginal dryness.
Edible plants normally contained in the diet, or materials used as herbal remedies/dietary supplements, may contain collections of structurally related compounds.
These related substances are often unique in their amounts and distribution when compared among various plant sources. The most notable groups of compounds exhibiting bioactivity are knovm as flavonoids, isoflavones, saponins, lignans, alkaloids, catechins and phenolic acids.
Epidemiology studies relating diet to disease suggest that dietary components may predispose populations to reduced risk of certain diseases. Far eastern populations consuming soy have reduced rates of breast, prostate and colon cancers and coronary heart disease, while populations in 1~inland have reduced rates of prostate cancer.
Researchers are just now studying the specific compounds in the diet to understand the basis for the epidemiological observations.
Among the various plants consumed in the diet, several are rich sources of phytochemzcals. Soy products contain high amounts of isoflavones and saponins, Unrefned diet grains include plants such as wheat, psyllium, rice, flax and oats that contain lignans. Cocoa contains catechins and phenolic acids. Certain non-dietary plants are also sources of the same chemical molecules, such as lignans and isoflavones in kudzu root or red Clovers. Isoflavones and lignans act as weak estrvgenie substances. Tea plants are also a rich source of phytochemicals, including catechins and phenolic acids.
Isvflavones can be used alone to treat or prevent breast cancer, prostate cancer, skin cancer, and colon cancer or as mechanism inhibitors. Xsotlavvnes alone may also reduce or prevent various symptoms related to the onset and duration of menopause, including hot flashes and osteoporosis. Isoflavones alone may also be effective in certain cardiovascular applications, including heart disease, reducing cholesterol-lipid levels, modulating angiogenesis, and other vascular effects. Moreover, isoflavones alone have been implicated in reducing headaches, dementia, inflammation, and alcohol abuse, as vvetl as inc~munomodulation.
Lignans alone have ~ been implicated in preventing or treating breast cancer, prostate cancer and colon cancer as well as reducing hot flashes, preventing osteoporosis
2 and showing antiviral potential. Lignans also have antimitotic and fungicidal activity. A
plant lignar~ the catecholic nordihydro-guaiaretic acid, was a potent antioxidant once used by the food industry.
Saponins alone have been implicated in preventing or treating Skin cancer, colon cancer, reducing serum cholesterol, and in inmnunomodutation and antiviral activity.
Saponins also exhibit antioxidant effects and act as free radical scavengers.
Phenolic acids have shown antioxidant activity.
People who eat a high soy diet show reduction of many of these above-discussed symptoms. This suggests that ingesting a combination of these phytochemicals in a ratio such as that found in soy may result in an additive or synergistic effect.
However, a high soy diet has some undesirable effects, including flatulence, undesirable taste, and hesitancy among Western consumers to change their lifestyle to iztcorporate soy in their diets, even for such benefits.
Isoflavones, which are heterocyclic phenols, are understood to include the soy compounds genistin, daidzin and glycitein, as well as biochanin A, equol, formononetin, and o-desmethylangolensin and natural derivatives thereof. These compounds and their aglycone or de-methylated aglycone forms, such as genistein and daidzein, are believed to have similar activities once they are ingested. They are sometimes referred to as phyto-estrogens.
Lignans are defined to be compounds possessing a 2,3-dibenzylbutane structure.
They include matairesinol, secoisotariciresinol, lariciresinol, isolariciresinol, nordihydroguaiaretic acid, pinoresinol, olivil, other compounds which may be precursors of entcrvlactone and enterodiol and modifications thereof, including diglucosides.
plant lignar~ the catecholic nordihydro-guaiaretic acid, was a potent antioxidant once used by the food industry.
Saponins alone have been implicated in preventing or treating Skin cancer, colon cancer, reducing serum cholesterol, and in inmnunomodutation and antiviral activity.
Saponins also exhibit antioxidant effects and act as free radical scavengers.
Phenolic acids have shown antioxidant activity.
People who eat a high soy diet show reduction of many of these above-discussed symptoms. This suggests that ingesting a combination of these phytochemicals in a ratio such as that found in soy may result in an additive or synergistic effect.
However, a high soy diet has some undesirable effects, including flatulence, undesirable taste, and hesitancy among Western consumers to change their lifestyle to iztcorporate soy in their diets, even for such benefits.
Isoflavones, which are heterocyclic phenols, are understood to include the soy compounds genistin, daidzin and glycitein, as well as biochanin A, equol, formononetin, and o-desmethylangolensin and natural derivatives thereof. These compounds and their aglycone or de-methylated aglycone forms, such as genistein and daidzein, are believed to have similar activities once they are ingested. They are sometimes referred to as phyto-estrogens.
Lignans are defined to be compounds possessing a 2,3-dibenzylbutane structure.
They include matairesinol, secoisotariciresinol, lariciresinol, isolariciresinol, nordihydroguaiaretic acid, pinoresinol, olivil, other compounds which may be precursors of entcrvlactone and enterodiol and modifications thereof, including diglucosides.
3 Phenolic acids include p-hydrbbenzoic acid, protocatechuic acid, and vanillic acid.
Other phenolic acids are chlorogenic acid, caffeic acid, ferulic acid, gallic acid, sinapic acid, syringic acid, coumaric acid, cinnamic acid, gentisic acid, salicylic acid, hydroxy benzoic acid and hydroxy phenyl acetic acids and derivatives. This list of phenolic acids should be understood to include the various isomers and derivatives found in the natural vegetable source.
Catechins, or flavan-3-ols, include epigallocatechin, catechin, epicatechin and gallocatechin.
Saponogenins are C-27 sterols in which the side chain has undergone metabolic changes to produce a spiroketal. Saponogenins occur naturally as saponins, which are 3-O-glycosides of the parent steroid or triterpenes. Digitonin from l.7igitalis is a saponin.
Saponins include glucosides of sapvgenin such as triterpenoids or steroids and saccharides such as glucose, arabinose, galactose or glucuronic acid. Typical examples of leguminous saponins are glycyrrhizin (glycyrrhetinic acid + glucuronic acid) contained in Glycyrrhiza glabra, soysaponin contained in soybean and alfalfasaponin contained in Medicago saliva.
Saponins also include chemical entities identified as triterpene phenols such as tomatine, soyasapogenols A, B, C, D, E and F, ginsengoside fraction 3 and 4, medicagenic acid, hederagenin, glycyrrhizin digitonin, quillaja saponin, lucernic acid and zahnic acid. The natural modifications of these compounds found in the vegetable source are also included in this identification.
A need exists for an improved composition consisting substantially of isoflavones, lignans, saponogenins, saponins, and/or phenolic acids which will produce improved results over any o~ these taken alone. Furthermore, a need exists for a composition in
Other phenolic acids are chlorogenic acid, caffeic acid, ferulic acid, gallic acid, sinapic acid, syringic acid, coumaric acid, cinnamic acid, gentisic acid, salicylic acid, hydroxy benzoic acid and hydroxy phenyl acetic acids and derivatives. This list of phenolic acids should be understood to include the various isomers and derivatives found in the natural vegetable source.
Catechins, or flavan-3-ols, include epigallocatechin, catechin, epicatechin and gallocatechin.
Saponogenins are C-27 sterols in which the side chain has undergone metabolic changes to produce a spiroketal. Saponogenins occur naturally as saponins, which are 3-O-glycosides of the parent steroid or triterpenes. Digitonin from l.7igitalis is a saponin.
Saponins include glucosides of sapvgenin such as triterpenoids or steroids and saccharides such as glucose, arabinose, galactose or glucuronic acid. Typical examples of leguminous saponins are glycyrrhizin (glycyrrhetinic acid + glucuronic acid) contained in Glycyrrhiza glabra, soysaponin contained in soybean and alfalfasaponin contained in Medicago saliva.
Saponins also include chemical entities identified as triterpene phenols such as tomatine, soyasapogenols A, B, C, D, E and F, ginsengoside fraction 3 and 4, medicagenic acid, hederagenin, glycyrrhizin digitonin, quillaja saponin, lucernic acid and zahnic acid. The natural modifications of these compounds found in the vegetable source are also included in this identification.
A need exists for an improved composition consisting substantially of isoflavones, lignans, saponogenins, saponins, and/or phenolic acids which will produce improved results over any o~ these taken alone. Furthermore, a need exists for a composition in
4 which the beneficial phytochemicals are enriched as compared to their original source.
This permits individuals to conveniently consume such phytochemieals as a nutritional supplement or as a food additive, Summary of the Invention An object of this ~ invention is to provide a convenient way for individuals to consume isoflavones, lignans, saponins, catechins and/or phenolic acids, either as a nutritional supplement or as an ingredient in a snore traditional type of food.
An other object of this invention is to provide an optimised extract composition of phytochemicals which is in sufficient concentration to be delivered in an easy to consume dosasge such as a pill, tablet, ea,psule, liquid or ingredient in a food.
Yet another object of this invention is to prepare the phytvchemical extract to be delivered as a topical application in a cream or lotion. In this form, the isoflavones, lignans, saponins, catechins and/or phenolic acids are dispersed and suspended in a suitable liquid or gel matrix to render a stable cream or lotion as the delivery vehicle.
A further object of this invention is to provide an extract concentrate which is closely similar in chemical composition to the chemical entities found in the natural plant source.
In keeping with this aspect of the invention, the isoflavoncs, lignans, saponins, caxechins and/or phenolic acids are extracted from a suitable vegetable source to render a composition which is substantially more concentrated than the original material and by more than 5 times in one or more of the desired bioactive components.
This extract may be used alone or combined with one or more other plant extracts to produce the optimized composition. Further, this extract composition may be formulated with one or more other dietary nutrients, such as vitamins, minerals, amino acids, etc., to provide a nutritional supplement further optimized for a desired health effect. All these ingredients may be combined with necessary binders, excipients, preservatives, colors and the like known to those in the industry in order to produce a suitable tablet, capsule, pill, liquid, cream, powder or food ingredient.
These phytochemicals may be packaged and provided in final form by means known to the supplements and food ingredient industries. The materials are intended to provide health and well-being benefits.
Accordingly, the present invention also seeks to provide a composition made by the process comprising the steps of:
a. extracting a defatted material from a group of vegetable matter consisting of protein, meal, whey, molasses, solubles and germs in a solution including an alcoholic solvent to produce a slurry;
b. filtering the slurry of step (a) to produce an alcoholic fraction c. evaporating said alcoholic fraction of step (b) to produce an aqueous fraction;
d. ultrafiltering said aqueous fraction of step (c)~
e. feeding a permeate of step (d) through a resin column; and f. collecting an effluent from said column after said wash.
In a further aspect, the present invention provided a A composition from a plant matter in which the composition is enriched in at least a first phytochemical and a second phytochemical selected from the group consisting of isoflavones, lignans, saponins, catechins and phenolic acids, said second phytochemical being a member of the group which is different from said first phytochemical.
Detailed Description of the Invention The improved composition is obtained by fractionating a plant source high in isoflavones, lignans and other phytochemicals such as defatted soybean flakes, soy molasses, soy whey, red clover, alfalfa, flax, cocoa, tea, or kudzu root. These may be fractionated alone or in combination with these other plants known to be high in the various isoflavones, lignans, saponins, catechines and phenolic acids. The fractionation results in substantially removing water, carbohydrates, proteins, and lipids from the source material. The fractionation method may be preferably that disclosed in co-pending U.S. Patent No. 5,702,752 or U.S. Patent No. 4,428,8?6, or an extraction using ethyl acetate or n-butanol may be used. U. S . Patent No . 5, 702, 752 is assigned to the assignee of this invention.
Other extraction processes, which may be used alone or in combination, include differential solubility, distillation, solvent extraction, adsorptive means, differential molecular filtration and precipitation.
6a The preferred composition is an improvement over known commercial materials regarding the amount of phytochemicals per gram of substance and the amounts of different phytochemieals present which affect physiologic function.
These natural substances have been consumed in food sources for long periods of time and more closely relate to the substances consumed which provide the basis far the epidemiological evidence for health benefits. Additional benefits may be derived fram improved physical properties relative to phytochemieals chemically modified from their original food source form. , The resulting composition is expected to comprise in a preferred form: between
This permits individuals to conveniently consume such phytochemieals as a nutritional supplement or as a food additive, Summary of the Invention An object of this ~ invention is to provide a convenient way for individuals to consume isoflavones, lignans, saponins, catechins and/or phenolic acids, either as a nutritional supplement or as an ingredient in a snore traditional type of food.
An other object of this invention is to provide an optimised extract composition of phytochemicals which is in sufficient concentration to be delivered in an easy to consume dosasge such as a pill, tablet, ea,psule, liquid or ingredient in a food.
Yet another object of this invention is to prepare the phytvchemical extract to be delivered as a topical application in a cream or lotion. In this form, the isoflavones, lignans, saponins, catechins and/or phenolic acids are dispersed and suspended in a suitable liquid or gel matrix to render a stable cream or lotion as the delivery vehicle.
A further object of this invention is to provide an extract concentrate which is closely similar in chemical composition to the chemical entities found in the natural plant source.
In keeping with this aspect of the invention, the isoflavoncs, lignans, saponins, caxechins and/or phenolic acids are extracted from a suitable vegetable source to render a composition which is substantially more concentrated than the original material and by more than 5 times in one or more of the desired bioactive components.
This extract may be used alone or combined with one or more other plant extracts to produce the optimized composition. Further, this extract composition may be formulated with one or more other dietary nutrients, such as vitamins, minerals, amino acids, etc., to provide a nutritional supplement further optimized for a desired health effect. All these ingredients may be combined with necessary binders, excipients, preservatives, colors and the like known to those in the industry in order to produce a suitable tablet, capsule, pill, liquid, cream, powder or food ingredient.
These phytochemicals may be packaged and provided in final form by means known to the supplements and food ingredient industries. The materials are intended to provide health and well-being benefits.
Accordingly, the present invention also seeks to provide a composition made by the process comprising the steps of:
a. extracting a defatted material from a group of vegetable matter consisting of protein, meal, whey, molasses, solubles and germs in a solution including an alcoholic solvent to produce a slurry;
b. filtering the slurry of step (a) to produce an alcoholic fraction c. evaporating said alcoholic fraction of step (b) to produce an aqueous fraction;
d. ultrafiltering said aqueous fraction of step (c)~
e. feeding a permeate of step (d) through a resin column; and f. collecting an effluent from said column after said wash.
In a further aspect, the present invention provided a A composition from a plant matter in which the composition is enriched in at least a first phytochemical and a second phytochemical selected from the group consisting of isoflavones, lignans, saponins, catechins and phenolic acids, said second phytochemical being a member of the group which is different from said first phytochemical.
Detailed Description of the Invention The improved composition is obtained by fractionating a plant source high in isoflavones, lignans and other phytochemicals such as defatted soybean flakes, soy molasses, soy whey, red clover, alfalfa, flax, cocoa, tea, or kudzu root. These may be fractionated alone or in combination with these other plants known to be high in the various isoflavones, lignans, saponins, catechines and phenolic acids. The fractionation results in substantially removing water, carbohydrates, proteins, and lipids from the source material. The fractionation method may be preferably that disclosed in co-pending U.S. Patent No. 5,702,752 or U.S. Patent No. 4,428,8?6, or an extraction using ethyl acetate or n-butanol may be used. U. S . Patent No . 5, 702, 752 is assigned to the assignee of this invention.
Other extraction processes, which may be used alone or in combination, include differential solubility, distillation, solvent extraction, adsorptive means, differential molecular filtration and precipitation.
6a The preferred composition is an improvement over known commercial materials regarding the amount of phytochemicals per gram of substance and the amounts of different phytochemieals present which affect physiologic function.
These natural substances have been consumed in food sources for long periods of time and more closely relate to the substances consumed which provide the basis far the epidemiological evidence for health benefits. Additional benefits may be derived fram improved physical properties relative to phytochemieals chemically modified from their original food source form. , The resulting composition is expected to comprise in a preferred form: between
5% and 95% isoflavones, between 0% and 70% lignans, and between 2% and 70%
saponins and sapogenins. In a more preferred form, the composition will be extracted from soy. In another preferred form, the composition will contain a ratio of (saponins plus saponogenins) to isoflavones from 1;100 to 100:1, with the isoflavanes consisting predominantly of naturally occurring derivatives of genistein and/or its precursor biochanin A and daidaein and/or its precursor formononetin, with a ratio of the genistein derivatives to daidzein derivatives from 100:1 to 1:100. Preferably, the isoflavones are predominantly glycosylated derivatives.
The composition's ratios may be readily varied by changing the plant source or by combining several plant sources for extraction. Thus, as further study shows which phytochemical combinations are more efficacious for certain health effects, the particular composition will also vary.
It is known that isoflavones, lignans, and saponins can be used advantageously to treat or prevcnt various cancers, including breast cancer, prostate cancer, skin cancer, and colon cancer.
It is believed that the improved composition will provide increased benefits in the form of chemopreventivn. Recent experiments appear to confirm this belief.
An initial series of animal studies was made to investigate the effects of dietary soy products on the growth of s.c. (SUBCUTANEOUS) implanted LNCaP in male SC1D
mice. A high isvflavone-containing say protein isolate (SPI) (2.0 mg isoflavones/g SPI) is provided by Protein Technology International (St. Louis, MO). A soy phytochemicals extract, soy phytochcmicals concentrate (SPC) which contains 28.5% total say isoflavones and a diverse amount of other soy phytochemicals, is provided by Archer Daniels Midland Company (Decatur, ITS). These materials were used to prepare six experimental diets.
Table 1 shows ingredients of the diets.
Eight-week-old male SC117 mice were s.c, injected on the right flank with 2 x LNCaP cells from hosts, randomized into six groups (n=10) and assigned to one of the experimental diets. Food intake, body weight, and tumor volume were measured.
At the termination of the experiment, blood samples were collected and serum separated for PSA
analysis. An aliquot of tumor tissues was Formalin-fixed, paraffin-embedded, and cut into 4 p.m sections for in situ histocheznical detection of apvptotic cells, and immunohistochemical analyses of angiogenesis and proliferation. Another aliquot was prepared for cell lysates for western blot to determine the expression of apoptosis-related gene products_ Table 2 summaries the effects of treatment on food intake, body weight, isoflavone intake and tumor volume. Soy products did not significantly alter food intake or body weight. Compared to casein-fed controls, tumor volumes from mice treated with SPI
(2O%), SPC (1.0%), and SPI and SI'C (1.0%) were reduced by 12%, 28% (P<0.04), or 40% (P<0.005), respectively. Factorial analysis indicated that there was no significant effect of protein source on tumor growth. Linear regression analysis indicated that tumor volumes were inversely correlated to total dietary isoflavones (Tumor volume (cm3) ~ _ .0008 + 2.121 x Isoflavones (tng), Rz = 0.76, p<0,03).
Table 3 shows the effects of SPC at 1.0% of the diet on apoptosis, proliferation, and angivgenesis of tumors from a pilot study. it indicates that dietary supplementation of soy phytochemicals inhibits the growth of LNCaP tumor in vivo by enhancing apoptvsis and inhibiting proliferation of tumor cells. Its inhibitory effect on tumor angiogenesis is not significant which may be due to small sample size (n--Z).
Results from in vitro study showed that genistein and soy phytochennical concentrate inhibited secretion of PSA by b.NCaP cells into media. PSA
concentrations were reduced 68% and 74% by 25 and 50 uM of genistein treatment respectively, and 31% and 42% by 25 and 50 ~M of soy phytvchemical concentrate treatment respectively.
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n Table 2. )final body weight, total food intake, total i5oflavonc intake, and tumor volume Treatment Body weightPood intake Total isoflavoneTumor volume rams cm3 /m Casein 22.40.5' _ 0.0010.00 2.320.312 46.63.1 SPI 23.I10.7 46.2.8 17.006.37 2.0610.32 Casein/LSPC 21.410.7 41.2.4 14.03.14 1.880.35 SPI/LSPC 22.610.6 50.14.7 29.36-2_76 1.66~0.29*
Casein/HSPC 22.20.7 44.86.1 76.3810.40 1.640.22*
SPI/fISPC 22.00.6 47.5i1:7 92.533.22 1.3910.30**
' Values are means ~ SE. ~ There are no significant differences of food intake or body weight among treatment groups.
Compared with control group, SP:ILLSPC, caseiri/I-iSPC, and SPI/HSPC had significantly smaller tumor volumes (*:p<0.04; **;p<0.005).
Table 3. Effects of treatment on apoptotic index (AI, % TUNEL), proliferation index (1'1i, PCNA Staining) and angiogenesis (microvessel density) Treatment AI % TUNEL PI %PCNA Mcrovessel Densi ~
Control (n=2) 6.07+0.88 60.11.1 12.S~.B
CaseinlHSPC 10.7510.54 51.7-1.3 9.710.7 (n=2) P value <0.02 <0.01 >0.05 Values are means tSlr.
Xn summary, preliminary results indicate that soy products inhibit the s.c.
growth of ~.NCaP
tumor in SCm mica, possibly via induction of apoptosis, and inhibition of angiogenesis and proliferation.
Isoflavones or lignans can alleviate menopausal-related Symptoms such as hot flashes arid osteoporosis as well as alleviate symptoms associated with menstruation. This is further believed to be due to their estrogenic activity. It is believed that the improved composition described here will aheviate these symptoms even more effectively.
Also, isoflavones positively affect various cardiovascular-related conditions, including heart disease, cholesterol (saponins also positively affect cholesterol), angiogenesis and other vascular effects.
It is believed that the improved composition will produce results for these cardiovascular conditions at least as beneficial as those hitherto known and at a reduced cost.
As explained earlier, isoflavones, lignans, and saponins are known to individually positively affect various neurological and immunological symptoms. It is believed that the improved composition will result in alleviating neurological and immunological symptoms at least as well as those compounds hitherto known and at a reduced cost. Moreover, it would be expected that some synergism would arise out of the combination described herein.
The improved . composition may be administered orally, parenterally, for instance, subeutaneously, intravenously, intramuscularly, intraperitoneally, by intranasal instillation or by application of an aerosol spray to mucous membranes, or to the skin by an ointment or a cream.
Administering the improved composition may be done with any suitable carrier, in solid or liquid dosage form such as tablets, capsules, powders, soft gels, solutions, suspensions, emulsions, ointments, or creams. The improved composition may also be administered as a food supplement or as a food ingredient.
The amount of the improved composition administered will vary depending on the person, the mode of administration, and the desired result. An effective amount is expected to be 10 mg to 2000 mg/per dose.
)Example 2 'Tablet Manufacture The composition provided far in this patent may be used to prepare tablets or other dosage forms. An example of a capsule preparation is provided in Example Z, The higher the concentration of the active component, the easier it is to form a tablet or emulsion. This leads to an added ability to incorporate ether dietary nutrients. An example would be to prepare a phytochemical tablet which incorporates calcium and vitamin E as a supplement to maintain bone health andlor reduce post menopausal symptoms such as hot flashes. In an example of this embodiment, a 600 me dry compression tablet was prepared containing a total of 125 mg of isvflavones concentrate (50 mg isoflavone compound). Included in the tablet formulation was a source of calcium and magnesium.
Dry compression tablets were produced by first blending the following ingredients: 4 kg of the improved composition (39.83% isoflavones), 1.91 kg sorbitol, 0.095 kg magnesium stearate, and 13.11 kg dicalcium phosphate in a 1Z0 quart capacity Hobart mixer. This blend of ingredients was then dry compressed at 1 ton pressure with a Stokes BB2 simple press into tablets having a total weight of 600 mg containing 125.53 mg of the in~zpraved composition and therefore 50 mg of total isoflavones.
Alternatively, a phytochemical concentrate may be provided in a single dosage form, a skin cream or as a food ingredient added to conventional food in amounts from 10 mg to 2000 mg/per dose, the purpose of which is to exert a positive effect on health and well being.
These benefits include.
cancer prevention, estrogen and sex hormone related maladies, inhibition of the pituitary-thyroid-gonadotrophic axis, alcohol dependency reduction, modulation of the cardiovascular, immune and nervous systems, antiviral effects and analgesic effects.
Example 3 Two-piece gelatin capsules were produced by filling the receiving end of the empty size "0"
capsules with 0.106 g of the improved composition (44,35% isoflavones) and closed with the capping end, providing a capsule containing 47.2 mg of total isoflavones.
Example 4 A comparison between various sources of phytochemical preparations is given in Table 4, It is readily seen that the phytochemical components of the composition of the "lsoflavone Concentrate" of this invention is substantially higher than the corresponding amounts in the natural vegetable materials.
Notably, the amount of glycone isoflavones and saponins are over 100 times more concentrated compared to the food source and over twenty times more concentrated compared to the germ o~ the plant which naturally concentrates these phytochemicals. Comparison of the "Isoflavvne Concentrate"
of this invention to other concentrates shows that the isoflavone fraction predominates in these latter products, reducing the amount of other healthful phytochemieals. Additionally, the extraction methods of these other products employ techniques which modify the components, particularly the isvflavones, so that they are not identical to the substances found in the natural vegetable material (U.5. Pat. No.
5,637,562).
One version of the improved composition was compared to other previously described compositions. The results are shown in Table 4.
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Separate solutions (0.02% in, distilled water) were made for genistein, genistin, daidzein, daidzin, and isoflavone concentrate in volumetric flasks. Samples were then placed in a 37°C water bath for 17 hours, followed by rapid filtration through a 0.2 micron syringe-type filter to remove particulates. Filtered samples were then analyzed for isoflavone concentration by HPLC. Results are tabulated as shown in 'f able 5.
Table 5. Differential Solubility of lsotlavone Glycosides vs. Aglycones lsoflavone Genistein Genistin Daidzein Daidzin (ppm) sarn 1e (ppm) (ppm) (ppm) Genistein 7.42 Genistin 33.89 Daidzein 3 .64 Daidzin 48.51 Isoflavone 0.492 30.075 0.672 37.69 Coaceatrate ~'he glycoside forms, genistin and daidzin, are at least 4.57 and 13.32 fold higher in concentration at 37°C than their corresponding aglycone forms, respectively.
'The modifications made to the isoflavones are to remove the carbohydrate attached to the isoflavvne moiety. This modification renders the isoflavone less soluble in water. Maintenance of the natural modification, glycosylation, enhances solubility. This fact is shown in the comparative solubility chart of Table 5. This chart shows that the genistin isoflavone is 4.6 times higher and the daidziz~ isvflavone is 13.3 times higher than the corresponding non-glycosylated form. Higher solubility caa lead to better bioavailability to intestinal organisms. The glycosylation does not inhibit absorption in the gut because the intestinal microflora convert the glycone form to the aglycone form before absorption occurs.
Example 6 Extraction of Lignans from Flax Lignans can be readily extracted from flax using this following method.
978 g of defatted flax meal (F1) was extracted with 2000 g of 85% ethanol at 40 ° C for 10 minutes, forming a slurry. The resulting slurry was filtered and extraction was repeated twice with a total of 6000 g of ethanol.
The ethanolic fraction was then evaporated undo vacuum at 70 ° C, resulting in an aqueous fraction of 1186 g. The anueous fraction was combined with 1000 g of water and mixed.
The mixed sample was then ultra-filtered through a 5000 molecular weight cutoff membrane, resulting in a 767 g permeate fraction and a retentate fraction of 1283 g.
The retentate fraction was freeze-dried, resulting in a 27.84 g sample (F2).
The 767 g permeate fraction at 50 ° C was fed to a 3 5 ml bed volume, XAD-4 resin column at a rate of 10 ml/tnin. The column efrluent was collected and dried, resulting in a 14.8 g sample (F3). XAD-4 is a trademark far an absorbent resin, available from Rohm &
Haas.
The column was then eluted with four bed volumes (140 ml) of 70% ethanol at 50 ° C. The eluent sample was evaporated under vacuum at 70 ° C
and dried, resulting in a 1.79 g sample (F4). The four fractions were then analyzed for their lignan content, measured as the concentration by weight of secoisolariciresinol. As Table 6 shows, this extraction method enriches lignan concentration.
Table 6 LICrNAN CONCENTRATIONS AS SECOISOLARICIRESINOL
SECO. CONC. (mg/g) 2.3 t.9 4.8 13.4 PHENOLIC AC.IA
While the present invention has been disclosed in terms o~ the preferred embodiment in order to facilitate a better understanding of the invention, it should be appreciated that the invention can be embodied in various ways without depaitinD from the principles of the invention. Therefore, the invention should be understood to include all possible embodiments, modifications, and equivalents to the described embodiment which do not depart form the principles of the inventions as set out in the appended claims.
saponins and sapogenins. In a more preferred form, the composition will be extracted from soy. In another preferred form, the composition will contain a ratio of (saponins plus saponogenins) to isoflavones from 1;100 to 100:1, with the isoflavanes consisting predominantly of naturally occurring derivatives of genistein and/or its precursor biochanin A and daidaein and/or its precursor formononetin, with a ratio of the genistein derivatives to daidzein derivatives from 100:1 to 1:100. Preferably, the isoflavones are predominantly glycosylated derivatives.
The composition's ratios may be readily varied by changing the plant source or by combining several plant sources for extraction. Thus, as further study shows which phytochemical combinations are more efficacious for certain health effects, the particular composition will also vary.
It is known that isoflavones, lignans, and saponins can be used advantageously to treat or prevcnt various cancers, including breast cancer, prostate cancer, skin cancer, and colon cancer.
It is believed that the improved composition will provide increased benefits in the form of chemopreventivn. Recent experiments appear to confirm this belief.
An initial series of animal studies was made to investigate the effects of dietary soy products on the growth of s.c. (SUBCUTANEOUS) implanted LNCaP in male SC1D
mice. A high isvflavone-containing say protein isolate (SPI) (2.0 mg isoflavones/g SPI) is provided by Protein Technology International (St. Louis, MO). A soy phytochemicals extract, soy phytochcmicals concentrate (SPC) which contains 28.5% total say isoflavones and a diverse amount of other soy phytochemicals, is provided by Archer Daniels Midland Company (Decatur, ITS). These materials were used to prepare six experimental diets.
Table 1 shows ingredients of the diets.
Eight-week-old male SC117 mice were s.c, injected on the right flank with 2 x LNCaP cells from hosts, randomized into six groups (n=10) and assigned to one of the experimental diets. Food intake, body weight, and tumor volume were measured.
At the termination of the experiment, blood samples were collected and serum separated for PSA
analysis. An aliquot of tumor tissues was Formalin-fixed, paraffin-embedded, and cut into 4 p.m sections for in situ histocheznical detection of apvptotic cells, and immunohistochemical analyses of angiogenesis and proliferation. Another aliquot was prepared for cell lysates for western blot to determine the expression of apoptosis-related gene products_ Table 2 summaries the effects of treatment on food intake, body weight, isoflavone intake and tumor volume. Soy products did not significantly alter food intake or body weight. Compared to casein-fed controls, tumor volumes from mice treated with SPI
(2O%), SPC (1.0%), and SPI and SI'C (1.0%) were reduced by 12%, 28% (P<0.04), or 40% (P<0.005), respectively. Factorial analysis indicated that there was no significant effect of protein source on tumor growth. Linear regression analysis indicated that tumor volumes were inversely correlated to total dietary isoflavones (Tumor volume (cm3) ~ _ .0008 + 2.121 x Isoflavones (tng), Rz = 0.76, p<0,03).
Table 3 shows the effects of SPC at 1.0% of the diet on apoptosis, proliferation, and angivgenesis of tumors from a pilot study. it indicates that dietary supplementation of soy phytochemicals inhibits the growth of LNCaP tumor in vivo by enhancing apoptvsis and inhibiting proliferation of tumor cells. Its inhibitory effect on tumor angiogenesis is not significant which may be due to small sample size (n--Z).
Results from in vitro study showed that genistein and soy phytochennical concentrate inhibited secretion of PSA by b.NCaP cells into media. PSA
concentrations were reduced 68% and 74% by 25 and 50 uM of genistein treatment respectively, and 31% and 42% by 25 and 50 ~M of soy phytvchemical concentrate treatment respectively.
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n Table 2. )final body weight, total food intake, total i5oflavonc intake, and tumor volume Treatment Body weightPood intake Total isoflavoneTumor volume rams cm3 /m Casein 22.40.5' _ 0.0010.00 2.320.312 46.63.1 SPI 23.I10.7 46.2.8 17.006.37 2.0610.32 Casein/LSPC 21.410.7 41.2.4 14.03.14 1.880.35 SPI/LSPC 22.610.6 50.14.7 29.36-2_76 1.66~0.29*
Casein/HSPC 22.20.7 44.86.1 76.3810.40 1.640.22*
SPI/fISPC 22.00.6 47.5i1:7 92.533.22 1.3910.30**
' Values are means ~ SE. ~ There are no significant differences of food intake or body weight among treatment groups.
Compared with control group, SP:ILLSPC, caseiri/I-iSPC, and SPI/HSPC had significantly smaller tumor volumes (*:p<0.04; **;p<0.005).
Table 3. Effects of treatment on apoptotic index (AI, % TUNEL), proliferation index (1'1i, PCNA Staining) and angiogenesis (microvessel density) Treatment AI % TUNEL PI %PCNA Mcrovessel Densi ~
Control (n=2) 6.07+0.88 60.11.1 12.S~.B
CaseinlHSPC 10.7510.54 51.7-1.3 9.710.7 (n=2) P value <0.02 <0.01 >0.05 Values are means tSlr.
Xn summary, preliminary results indicate that soy products inhibit the s.c.
growth of ~.NCaP
tumor in SCm mica, possibly via induction of apoptosis, and inhibition of angiogenesis and proliferation.
Isoflavones or lignans can alleviate menopausal-related Symptoms such as hot flashes arid osteoporosis as well as alleviate symptoms associated with menstruation. This is further believed to be due to their estrogenic activity. It is believed that the improved composition described here will aheviate these symptoms even more effectively.
Also, isoflavones positively affect various cardiovascular-related conditions, including heart disease, cholesterol (saponins also positively affect cholesterol), angiogenesis and other vascular effects.
It is believed that the improved composition will produce results for these cardiovascular conditions at least as beneficial as those hitherto known and at a reduced cost.
As explained earlier, isoflavones, lignans, and saponins are known to individually positively affect various neurological and immunological symptoms. It is believed that the improved composition will result in alleviating neurological and immunological symptoms at least as well as those compounds hitherto known and at a reduced cost. Moreover, it would be expected that some synergism would arise out of the combination described herein.
The improved . composition may be administered orally, parenterally, for instance, subeutaneously, intravenously, intramuscularly, intraperitoneally, by intranasal instillation or by application of an aerosol spray to mucous membranes, or to the skin by an ointment or a cream.
Administering the improved composition may be done with any suitable carrier, in solid or liquid dosage form such as tablets, capsules, powders, soft gels, solutions, suspensions, emulsions, ointments, or creams. The improved composition may also be administered as a food supplement or as a food ingredient.
The amount of the improved composition administered will vary depending on the person, the mode of administration, and the desired result. An effective amount is expected to be 10 mg to 2000 mg/per dose.
)Example 2 'Tablet Manufacture The composition provided far in this patent may be used to prepare tablets or other dosage forms. An example of a capsule preparation is provided in Example Z, The higher the concentration of the active component, the easier it is to form a tablet or emulsion. This leads to an added ability to incorporate ether dietary nutrients. An example would be to prepare a phytochemical tablet which incorporates calcium and vitamin E as a supplement to maintain bone health andlor reduce post menopausal symptoms such as hot flashes. In an example of this embodiment, a 600 me dry compression tablet was prepared containing a total of 125 mg of isvflavones concentrate (50 mg isoflavone compound). Included in the tablet formulation was a source of calcium and magnesium.
Dry compression tablets were produced by first blending the following ingredients: 4 kg of the improved composition (39.83% isoflavones), 1.91 kg sorbitol, 0.095 kg magnesium stearate, and 13.11 kg dicalcium phosphate in a 1Z0 quart capacity Hobart mixer. This blend of ingredients was then dry compressed at 1 ton pressure with a Stokes BB2 simple press into tablets having a total weight of 600 mg containing 125.53 mg of the in~zpraved composition and therefore 50 mg of total isoflavones.
Alternatively, a phytochemical concentrate may be provided in a single dosage form, a skin cream or as a food ingredient added to conventional food in amounts from 10 mg to 2000 mg/per dose, the purpose of which is to exert a positive effect on health and well being.
These benefits include.
cancer prevention, estrogen and sex hormone related maladies, inhibition of the pituitary-thyroid-gonadotrophic axis, alcohol dependency reduction, modulation of the cardiovascular, immune and nervous systems, antiviral effects and analgesic effects.
Example 3 Two-piece gelatin capsules were produced by filling the receiving end of the empty size "0"
capsules with 0.106 g of the improved composition (44,35% isoflavones) and closed with the capping end, providing a capsule containing 47.2 mg of total isoflavones.
Example 4 A comparison between various sources of phytochemical preparations is given in Table 4, It is readily seen that the phytochemical components of the composition of the "lsoflavone Concentrate" of this invention is substantially higher than the corresponding amounts in the natural vegetable materials.
Notably, the amount of glycone isoflavones and saponins are over 100 times more concentrated compared to the food source and over twenty times more concentrated compared to the germ o~ the plant which naturally concentrates these phytochemicals. Comparison of the "Isoflavvne Concentrate"
of this invention to other concentrates shows that the isoflavone fraction predominates in these latter products, reducing the amount of other healthful phytochemieals. Additionally, the extraction methods of these other products employ techniques which modify the components, particularly the isvflavones, so that they are not identical to the substances found in the natural vegetable material (U.5. Pat. No.
5,637,562).
One version of the improved composition was compared to other previously described compositions. The results are shown in Table 4.
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a 'v a w m a Example 5 The improved composition, containing the glycoside forms of isvflavones, has as one aspect an improved solubility at body temperature over the previously described compositions containing the aglycoside forms.
Separate solutions (0.02% in, distilled water) were made for genistein, genistin, daidzein, daidzin, and isoflavone concentrate in volumetric flasks. Samples were then placed in a 37°C water bath for 17 hours, followed by rapid filtration through a 0.2 micron syringe-type filter to remove particulates. Filtered samples were then analyzed for isoflavone concentration by HPLC. Results are tabulated as shown in 'f able 5.
Table 5. Differential Solubility of lsotlavone Glycosides vs. Aglycones lsoflavone Genistein Genistin Daidzein Daidzin (ppm) sarn 1e (ppm) (ppm) (ppm) Genistein 7.42 Genistin 33.89 Daidzein 3 .64 Daidzin 48.51 Isoflavone 0.492 30.075 0.672 37.69 Coaceatrate ~'he glycoside forms, genistin and daidzin, are at least 4.57 and 13.32 fold higher in concentration at 37°C than their corresponding aglycone forms, respectively.
'The modifications made to the isoflavones are to remove the carbohydrate attached to the isoflavvne moiety. This modification renders the isoflavone less soluble in water. Maintenance of the natural modification, glycosylation, enhances solubility. This fact is shown in the comparative solubility chart of Table 5. This chart shows that the genistin isoflavone is 4.6 times higher and the daidziz~ isvflavone is 13.3 times higher than the corresponding non-glycosylated form. Higher solubility caa lead to better bioavailability to intestinal organisms. The glycosylation does not inhibit absorption in the gut because the intestinal microflora convert the glycone form to the aglycone form before absorption occurs.
Example 6 Extraction of Lignans from Flax Lignans can be readily extracted from flax using this following method.
978 g of defatted flax meal (F1) was extracted with 2000 g of 85% ethanol at 40 ° C for 10 minutes, forming a slurry. The resulting slurry was filtered and extraction was repeated twice with a total of 6000 g of ethanol.
The ethanolic fraction was then evaporated undo vacuum at 70 ° C, resulting in an aqueous fraction of 1186 g. The anueous fraction was combined with 1000 g of water and mixed.
The mixed sample was then ultra-filtered through a 5000 molecular weight cutoff membrane, resulting in a 767 g permeate fraction and a retentate fraction of 1283 g.
The retentate fraction was freeze-dried, resulting in a 27.84 g sample (F2).
The 767 g permeate fraction at 50 ° C was fed to a 3 5 ml bed volume, XAD-4 resin column at a rate of 10 ml/tnin. The column efrluent was collected and dried, resulting in a 14.8 g sample (F3). XAD-4 is a trademark far an absorbent resin, available from Rohm &
Haas.
The column was then eluted with four bed volumes (140 ml) of 70% ethanol at 50 ° C. The eluent sample was evaporated under vacuum at 70 ° C
and dried, resulting in a 1.79 g sample (F4). The four fractions were then analyzed for their lignan content, measured as the concentration by weight of secoisolariciresinol. As Table 6 shows, this extraction method enriches lignan concentration.
Table 6 LICrNAN CONCENTRATIONS AS SECOISOLARICIRESINOL
SECO. CONC. (mg/g) 2.3 t.9 4.8 13.4 PHENOLIC AC.IA
While the present invention has been disclosed in terms o~ the preferred embodiment in order to facilitate a better understanding of the invention, it should be appreciated that the invention can be embodied in various ways without depaitinD from the principles of the invention. Therefore, the invention should be understood to include all possible embodiments, modifications, and equivalents to the described embodiment which do not depart form the principles of the inventions as set out in the appended claims.
Claims (54)
1. A composition from a plant matter in which the composition is enriched in at least a first phytochemical and a second phytochemical selected from the group consisting of isoflavones, lignans, saponins, catechins and phenolic acids, said second phytochemical being a member of the group which is different from said first phytochemical.
2. The composition of claim 1 which essentially consists of at least 70% by weight phytochemicals selected from the group comprising isoflavones, lignans, saponins, catechins and phenolic acids.
3. The composition of claim 1 in which at least one of the selected phytochemicals comprises at least 10% by weight of the composition.
4. The composition of claim 1 which essentially consists of at least 80% by weight phytochemicals selected from the group comprising isoflavones, lignans, saponins, catechins and phenolic acids.
5. The composition of claim 1 which essentially consists of at least 90% by weight phytochemicals selected from the group comprising isoflavones, lignans, saponins, catechins and phenolic acids.
6. The composition of claim 1 in which the ratio by weight of isoflavones to lignans is selected from the range of about 1000:1 to about 1:50.
7. The composition of claim 1 in which the ratio by weight of isoflavones to saponins is selected from the range of about 1:10 to about 10:1.
8. The composition of claim 1 in which the ratio by weight of isoflavones to phenolic acids is selected from the range of about 100 to 1 to about 1 to 100.
9. The composition of claim 1 in which the ratio by weight of lignans to saponins is selected from the range of out 100 to 1 to about 1 to 100.
10. The composition of claim 1 in which the ratio by weight of lignans to phenolic acids is selected from the range of about 100 to 1 to about 1 to 100.
11. The composition of claim 1 in which the ratio by weight of saponins to phenolic acids is selected from the range of about 100 to 1 to about 1 to 100.
12. The composition of claim 1 in which the ratio of catechins to phenolic acid is selected from a range by weight of about 100 to 1 to about 1 to 100.
13. The composition of claim 1 in which the isoflavones are present in an amount from approximately 5%
to approximately 90% by weight.
to approximately 90% by weight.
14. The composition of claim 1 in which the lignans are present in an amount from about 1% to about 70% by weight.
15. The composition of claim 1 in which the saponins are present in an amount from about 5% to about 70% by weight.
16. The composition of claim 1 in which the phenolic acids are present in an amount from about to 1% about 70%
by weight.
by weight.
17. The composition of claim 1 in which the isoflavones are selected from the group consisting essentially of genistein, daidzein, glycitein, biochanin A, formononetin, and natural modifications thereof.
18. The composition of claim 1 in which the lignans are selected from the group of compounds possessing a 2,3-dibenzylbutane structure and consisting essentially of matairesinol, secoisolariciresinol, lariciresinol, isolariciresinol, nordihydroguaiaretic acid, pinoresinol, olivil, and precursors of enterolactone and enterodiol and natural modifications thereof.
19. The composition of claim 1 in which the saponins are selected from the group consisting essentially of tomatine, soyasapogenols A, B, C, D, E and F, soyasaponin, alfalfasaponin, ginsenoside fraction 3 and 4, medicagenic acid, hederagenin, glycyrrhizin, digitonin, quillaja saponin, lucernic acid, zahnic acid, and natural modifications of these compounds.
20. The composition of claim 1 in which the phenolic acids are selected from the group consisting essentially of chlorogenic acid, caffeic acid, ferulic acid, gallic acid, sinapic acid, syringic acid, vanillic acid, coumeric acid, cinnamic acid, genistic acid, salicylic acid, hydroxy benzoic acid and hydroxy phenyl acetic acids and derivatives thereof.
21. The composition of claim 1 in which catechins are selected from the group consisting essentially of catechin, epicatechin, gallocatechin, and epigallocatechin.
22. The composition of claim 1 in which the plant matter is selected from one or more of the group consisting essentially of soy, red clover, kudzu, flax, alfalfa, tea, and cocoa.
23. The composition of claim 1 in which the plant matter is soy.
24. The composition of claim 23, in which the soy is selected from the group consisting of soybean, soy foods, soy molasses, soy whey, soy protein, and soy flour.
25. A product for oral delivery comprising a composition extracted from plant matter which is enriched in at least a first phytochemical and a second phytochemical selected from the group consisting of isoflavones, lignans, saponins, catechins and phenolic acids, said second phytochemical being a member of the group which is different from said first phytochemical.
26. The product of claim 25 wherein the form of the product is selected from the group consisting of tablets, capsules, pills, concentrates, powders, liquids, and added food ingredients.
27. The product of claim 26 comprising tablets comprising a. the plant matter composition; and b. a filler selected from the group consisting of sorbitol, lactose, cellulose and dicalcium phosphate.
28. The product of claim 27 additionally comprising a dietary supplemental. nutrient selected from the group consisting of vitamins and minerals.
29. The oral delivery product of claim 27 wherein the product comprises between about 15% and about 25% by weight of the composition and between about 65% and about 85% by weight of the filler.
30. The product of claim 28 wherein the product comprises a. between about 15% and about 25% by weight of the composition;
b. between about 60% and about 84% by weight of the filler; and c. between about 1% and about 25% by weight of the dietary supplemental nutrient.
b. between about 60% and about 84% by weight of the filler; and c. between about 1% and about 25% by weight of the dietary supplemental nutrient.
31. The oral delivery product of claim 26 comprising capsules including a. a predetermined dosage of the plant matter composition; and b. a gelatin capsule.
32. The oral delivery product of claim 26 wherein the plant matter composition is extracted from plants selected from the group consisting of soy, red clover, kudzu, flax, alfalfa, tea, and cocoa.
33. The oral delivery product of claim 25 wherein the product comprises between about 10 milligrams and about 2000 milligrams of the plant matter composition.
34. The composition of claim 1 in which the selected phytochemicals are substantially in a native form.
35. The composition of claim 1 in which the isoflavones are substantially in a glycosylated form.
36. The composition of claim 1 which is in a form suitable for administering as a food supplement.
37. The composition of claim 1 which is in a form suitable for administering as a dietary supplement.
38. The composition of claim 1 in which the plant matter is tea.
39. The composition of claim 1 in which the plant matter is cocoa.
40. The composition of claim 1 in which the plant matter is flax.
41. The composition of claim 40 which consists of at least about 1% by weight lignans.
42. The composition of claim 40 which consists of at least about 50% by weight lignans.
43. A composition made by the process comprising the steps of:
a. extracting a defatted material from a group of vegetable matter consisting of protein, meal, whey, molasses, solubles and germs in a solution including an alcoholic solvent to produce a slurry;
b. filtering the slurry of step (a) to produce an alcoholic fraction;
c. evaporating said alcoholic fraction of step (b) to produce an aqueous fraction;
d, ultrafiltering said aqueous fraction of step (c);
e. feeding a permeate of step (d) through a resin column; and f. collecting an effluent from said column after said wash.
a. extracting a defatted material from a group of vegetable matter consisting of protein, meal, whey, molasses, solubles and germs in a solution including an alcoholic solvent to produce a slurry;
b. filtering the slurry of step (a) to produce an alcoholic fraction;
c. evaporating said alcoholic fraction of step (b) to produce an aqueous fraction;
d, ultrafiltering said aqueous fraction of step (c);
e. feeding a permeate of step (d) through a resin column; and f. collecting an effluent from said column after said wash.
44. The composition of claim 43 and the further step of preparing said effluent of step (f) into a form which is suitable for administering orally, said form being taken from a group consisting of a concentrate, dried powder, capsule, pellet, and pill.
45. The composition of claim 41 wherein said dried powder is a bulk volume of material for further manufacture to provide individual dose sizes for said oral administration.
46. The composition of claim 43 wherein said vegetable matter is selected from a group consisting of soy, red clover, kudzu, flax, alfalfa, tea, and cocoa.
47. The composition of claim 43 wherein said vegetable matter is soy.
48. The composition of claim 43 wherein step (c) includes a step of diluting said aqueous fraction.
49. The composition of claim 43 and the added step of fractionating said effluent to select at least one of the group consisting essentially of isoflavones, lignans, saponins, catechins, and phenolic acid.
50. The composition of claim 43 and the added step of fractionating said effluent to select isoflavones.
51. The composition of claim 43 wherein the solution of step (a) is about 70% ethanol and the extraction is carried out at about 40°C.
52. The composition of claim 43 where the evaporation of step (c) is carried out under vacuum at about 70°C.
53. The composition of claim 2 in a form suitable for administering as a medication to treat an illness selected from a group consisting of breast cancer, colon cancer, bladder cancer, prostrate cancer, urinary cancer, migraine headaches, dementia, alcohol dependency, reduction of bloodstream cholesterol, coronary heart disease, modulation of blood lipid profile, hot flashes, osteoporosis, sleep disorders, vaginal dryness, and premenstrual syndrome.
54. The product of claim 28 wherein the dietary supplemental nutrient is selected from the group consisting of dicalcium phosphate, magnesium stearate, calcium citrate, and calcium malate.
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US6054997P | 1997-10-02 | 1997-10-02 | |
US60/060,549 | 1997-10-02 | ||
US09/162,038 US6261565B1 (en) | 1996-03-13 | 1998-09-28 | Method of preparing and using isoflavones |
US09/162,038 | 1998-09-28 |
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US (9) | US6261565B1 (en) |
EP (2) | EP0906761B1 (en) |
JP (1) | JPH11221048A (en) |
KR (2) | KR19990066785A (en) |
AT (2) | ATE270894T1 (en) |
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Families Citing this family (186)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69333624T2 (en) * | 1992-05-19 | 2005-09-15 | Novogen Research Pty. Ltd., North Ryde | USE OF ISOFLAVON PHYTO-ESTROGEN EXTRACTS OF SOY OR CLOVER |
US5554645A (en) | 1994-10-03 | 1996-09-10 | Mars, Incorporated | Antineoplastic cocoa extracts and methods for making and using the same |
US6391310B1 (en) * | 1996-03-13 | 2002-05-21 | Archer Daniels Midland Company | Method of preparing and using isoflavones for the treatment of neurological symptoms |
US6261565B1 (en) * | 1996-03-13 | 2001-07-17 | Archer Daniels Midland Company | Method of preparing and using isoflavones |
US5821361A (en) * | 1996-06-11 | 1998-10-13 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
AUPO203996A0 (en) * | 1996-08-30 | 1996-09-26 | Novogen Research Pty Ltd | Therapeutic uses |
US6558713B2 (en) | 1996-09-06 | 2003-05-06 | Mars, Incorporated | Health of a mammal by administering a composition containing at least one cocoa polyphenol ingredient |
US7968140B2 (en) | 1997-09-08 | 2011-06-28 | Mars, Incorporated | Chocolates and chocolate liquor having an enhanced polyphenol content |
US6998418B1 (en) | 1996-11-05 | 2006-02-14 | Gp Medical, Inc. | Acellular biological material chemically treated with genipin |
US6146668A (en) | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
NZ527735A (en) * | 1997-05-01 | 2005-10-28 | Novogen Inc | Treatment or prevention of menopausal symptoms and osteoporosis |
US20030153541A1 (en) * | 1997-10-31 | 2003-08-14 | Robert Dudley | Novel anticholesterol compositions and method for using same |
US6696484B2 (en) | 1997-10-31 | 2004-02-24 | University Of Chicago Office Of Technology And Intellectual Property | Method and compositions for regulation of 5-alpha reductase activity |
EP1027045A4 (en) * | 1997-10-31 | 2004-12-08 | Arch Dev Corp | Methods and compositions for regulation of 5-alpha reductase activity |
AUPP260798A0 (en) | 1998-03-26 | 1998-04-23 | Novogen Research Pty Ltd | Treatment of medical related conditions with isoflavone containing extracts of clover |
CA2333556A1 (en) * | 1998-05-27 | 1999-12-02 | Sherwood L. Gorbach | Isoflavonoids for treatment and prevention of migraine headaches |
WO1999066915A2 (en) * | 1998-06-23 | 1999-12-29 | Southern Illinois University At Carbondale | Therapeutic applications of estrogenic carboxylic acids |
JP2000095792A (en) * | 1998-09-21 | 2000-04-04 | Showa Sangyo Co Ltd | Acquisition of isoflavone composition comprising genistin |
DE60021873T2 (en) * | 1999-04-13 | 2006-05-24 | Scigenic Co., Ltd. | PREPARATION FOR THE PROPHYLAXIS OR TREATMENT OF DEMENTIA DISEASE CONTAINS A HYDROXYZYLIC ACID DERIVATIVE OR AN EXTRACT OF A PLANT OF THE GENUS ANGELICA CONTAINING THIS ACID. |
US6592910B1 (en) * | 1999-04-20 | 2003-07-15 | Board Of Trustees, Southern Illinois University | Methods of treating clinical diseases with isoflavones |
US20040072765A1 (en) * | 1999-04-28 | 2004-04-15 | Novogen Research Pty Ltd. | Cardiovascular and bone treatment using isoflavones |
AUPQ008399A0 (en) * | 1999-04-28 | 1999-05-27 | Novogen Research Pty Ltd | Cariovascular applications |
AU4550100A (en) * | 1999-05-05 | 2000-11-21 | Herzog, Leslie J. | Food product |
AU4118700A (en) * | 1999-05-05 | 2000-11-21 | Herzog, Leslie J. | Food product |
CA2375633C (en) * | 1999-06-01 | 2014-03-18 | Ocean Spray Cranberries, Inc. | Cranberry seed oil extract and compositions containing components thereof |
FR2794616B1 (en) * | 1999-06-11 | 2001-09-07 | Tekory S A R L | NATURAL FOOD SUPPLEMENT FOR DECREASING THE RATE OF PLASMA CHOLESTEROL AND PROCESS FOR PREPARING THE SAME |
US20090233999A1 (en) * | 1999-09-06 | 2009-09-17 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
AUPQ266199A0 (en) * | 1999-09-06 | 1999-09-30 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
ATE388718T1 (en) | 1999-09-30 | 2008-03-15 | Factors R & D Technologies Ltd | ECHINACEA COMPOSITION AND METHOD FOR PREPARATION |
US7182972B2 (en) | 1999-12-17 | 2007-02-27 | Quercegen Pharma, Llc | Water-soluble bean-based extracts |
AU2005220186B2 (en) * | 1999-12-17 | 2008-08-28 | Lan Bo Chen | Water soluble bean-based extracts |
EP1239743B1 (en) * | 1999-12-17 | 2009-09-16 | Mitsunori Ono | Water-soluble bean-based extracts |
AUPQ520300A0 (en) * | 2000-01-21 | 2000-02-17 | Novogen Research Pty Ltd | Food product and process |
CA2405348A1 (en) * | 2000-04-13 | 2001-11-01 | Ocean Spray Cranberries, Inc. | Novel compositions derived from cranberry and grapefruit and therapeutic uses therefor |
WO2001085183A2 (en) * | 2000-05-08 | 2001-11-15 | N.V. Nutricia | Preparation for the prevention and treatment of ocular disorders |
KR100432234B1 (en) * | 2000-05-12 | 2004-05-20 | 솔레 엘엘씨 | Process for separating and recovering protein and isoflavones from a plant material |
US6627232B1 (en) | 2000-06-09 | 2003-09-30 | Mars Incorporated | Method for extracting cocoa procyanidins |
US6989161B2 (en) | 2000-06-12 | 2006-01-24 | Access Business Group International Llc | Phytonutrient nutritional supplement |
JP2002051732A (en) * | 2000-06-12 | 2002-02-19 | Access Business Group Llc | Composition and method for correcting deficiency disease of vegetable chemical substance by diet |
US7438936B2 (en) | 2000-06-12 | 2008-10-21 | Access Business Group International Llc | Dietary supplement and related method |
US7939115B2 (en) | 2000-06-12 | 2011-05-10 | Access Business Group International Llc | Dietary supplement and related method |
US7416749B2 (en) | 2000-06-12 | 2008-08-26 | Access Business Group International Llc | Dietary supplement and related method |
JP3548102B2 (en) * | 2000-08-07 | 2004-07-28 | 花王株式会社 | Antihypertensive agent |
FR2812873B1 (en) | 2000-08-11 | 2003-08-01 | Barry Callebaut France | PROCESS FOR PRODUCING POLYPHENOLS FROM COCOA BEANS |
CA2358321A1 (en) * | 2000-09-29 | 2002-03-29 | Kraft Foods Holdings, Inc. | Method and composition which inhibits the oxidation of omega-3- and omega-6 polyunsaturated lipids |
JP4858889B2 (en) * | 2000-10-20 | 2012-01-18 | 有限会社大長企画 | Nutrient, digestive |
AU2001235969A1 (en) * | 2000-10-23 | 2002-05-06 | Council Of Scientific And Industrial Research | Pharmaceutical composition comprising wikstromol and/or matairesinol, its use as hepatoprotectant and process for their isolation from cedrus deodara |
US20040219281A1 (en) * | 2000-11-21 | 2004-11-04 | Cargill, Incorporated | Modified oilseed material |
US7429399B2 (en) * | 2001-06-18 | 2008-09-30 | Solae, Llc | Modified oilseed material |
US6632459B2 (en) | 2000-12-11 | 2003-10-14 | Nutricia N.V. | Chlorogenic acid and an analog thereof for immune system stimulation |
FR2818096B1 (en) * | 2000-12-14 | 2004-05-07 | Daniel Chajuss | PHYTOCHEMICAL COMPOSITION OF SOYBEANS |
JP4880816B2 (en) * | 2000-12-15 | 2012-02-22 | 株式会社ヤクルト本社 | Skin anti-aging agent |
US20020114795A1 (en) | 2000-12-22 | 2002-08-22 | Thorne Kevin J. | Composition and process for bone growth and repair |
US20030190381A1 (en) * | 2001-02-02 | 2003-10-09 | Bland Jeffrey S. | Medical composition for balancing bodily processes |
US20040220118A1 (en) * | 2001-02-02 | 2004-11-04 | Bland Jeffrey S. | Medical composition for balancing bodily processes |
US20060034954A1 (en) * | 2001-02-02 | 2006-02-16 | Bland Jeffrey S | Medical composition for balancing bodily processes |
US20070059378A1 (en) * | 2001-02-02 | 2007-03-15 | Metagenics, Inc. | Medical composition for balancing bodily processes |
AUPR363301A0 (en) | 2001-03-08 | 2001-04-05 | Novogen Research Pty Ltd | Dimeric isoflavones |
US20050119301A1 (en) * | 2001-03-16 | 2005-06-02 | Alan Husband | Treatment of restenosis |
US6767565B2 (en) * | 2001-03-22 | 2004-07-27 | Archer Daniels Midland Company | Process for obtaining lignan |
ES2271261T3 (en) * | 2001-04-04 | 2007-04-16 | Unilever N.V. | USE OF LINKS IN FOOD. |
ATE541569T1 (en) * | 2001-07-24 | 2012-02-15 | Cargill Inc | METHOD FOR ISOLATION OF PHENOLIC COMPOUNDS |
US6489514B1 (en) * | 2001-07-27 | 2002-12-03 | Council Of Scientific And Industrial Research | (-)-Secoisolariciresinol as an antioxidant obtained from a new natural source namely stereospermum personatum |
US6592911B2 (en) * | 2001-07-27 | 2003-07-15 | Council Of Scientific And Industrial Research | (−)-Olivil as antioxidant which is obtained from a new natural source namely Stereospermum personatum |
US7338971B2 (en) * | 2001-08-30 | 2008-03-04 | El-Naggar Mawaheb M | Treatment of inflammatory, cancer, and thrombosis disorders |
US6586018B1 (en) * | 2001-08-31 | 2003-07-01 | Sabina Fasano | Herbal composition |
KR100460103B1 (en) * | 2001-10-18 | 2004-12-04 | 롯데제과주식회사 | Drug with inhibitor effects on digestive system carcinogenesis containing cacao bean and husk fraction extract |
US7008666B2 (en) | 2001-11-26 | 2006-03-07 | Hormos Nutraceutical Oy Ltd. | Method of inhibiting overactivity of phagocytes or lymphocytes in an individual |
AU2002222501A1 (en) * | 2001-12-05 | 2003-06-17 | Council Of Scientific And Industrial Research | A novel herbal chemical composition for the treatment of cancer |
JP2012149096A (en) * | 2001-12-18 | 2012-08-09 | Daicho Kikaku:Kk | Anti-inflammatory preparation |
JP5384777B2 (en) * | 2001-12-18 | 2014-01-08 | 有限会社大長企画 | Strong muscle agent, anti-inflammatory agent |
US20030144216A1 (en) * | 2002-01-25 | 2003-07-31 | Mikko Unkila | Method for prevention of diseases in coeliac patients |
AU2003201621A1 (en) * | 2002-02-05 | 2003-09-02 | Hormos Nutraceutical Oy Ltd | Lignan derivatives |
ATE361746T1 (en) * | 2002-03-06 | 2007-06-15 | Medical Res And Education Trus | BOTANICAL EXTRACT WITH ANTI-CANCER ACTIVITY CONTAINING ISOLIQUIRITIGENIN |
EP1808172A3 (en) * | 2002-03-06 | 2010-05-26 | Activephyto Technologies Limited | Botanical extract compositions and methods of use |
WO2003075686A1 (en) * | 2002-03-11 | 2003-09-18 | Suntory Limited | Process for producing sdg and foods and drinks containing the same |
US7514107B2 (en) * | 2002-03-21 | 2009-04-07 | Mars, Incorporated | Treatment of diseases involving defective gap junctional communication |
US7048960B2 (en) * | 2002-03-22 | 2006-05-23 | Glenn Roy Pizzey | High lignan flaxseed product and product by process |
WO2003082888A1 (en) * | 2002-03-26 | 2003-10-09 | Wiley Organics, Inc. | Process for isolating genisting from mixtures of soy isoflavones |
KR100946822B1 (en) | 2002-05-01 | 2010-03-09 | 가부시끼가이샤 하야시바라 세이부쓰 가가꾸 겐꾸조 | Calcium-containing tissue strengthening agents and use thereof |
EP1503632A1 (en) * | 2002-05-02 | 2005-02-09 | Volker Kuellmer | Coated, agglomerated phytochemicals |
KR100479405B1 (en) * | 2002-05-24 | 2005-03-30 | 주식회사 싸이제닉 | Cinnamic acid dimers, their preparation and the use thereof for treating neurodegenerative disease |
US7214394B2 (en) * | 2002-05-31 | 2007-05-08 | Archer-Daniels-Midland Company | Policosanol compositions, extraction from novel sources, and uses thereof |
BR0311866A (en) * | 2002-06-11 | 2005-03-15 | Panagin Pharmaceuticals Inc | Saponin or sapogenin compositions for cancer therapy |
CA2448513A1 (en) * | 2002-06-29 | 2003-12-29 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Isoflavone concentrates, as well as methods for their production |
US20040009872A1 (en) * | 2002-07-15 | 2004-01-15 | Gordon Cohen | Method using solvents for improved microporous polymeric adsorbents |
AU2003252655A1 (en) * | 2002-07-18 | 2004-02-09 | Takara Bio Inc. | Remedy |
EP2526940A3 (en) | 2002-07-24 | 2014-07-30 | Children's Hospital Medical Center | Compositions containing enantiomeric equol, and methods for their making |
JP4290119B2 (en) * | 2002-07-24 | 2009-07-01 | 株式会社紅豆杉 | Antihyperglycemic agent, hepatoprotectant, anticancer agent, including red cedar derived lignans |
WO2004012697A1 (en) * | 2002-07-25 | 2004-02-12 | L'oréal | Cosmetic use of lignans |
AU2003258529A1 (en) * | 2002-07-25 | 2004-02-16 | L'oreal | Use of lignans for prevening or treating the sings of ageing of the skin |
FR2842732B1 (en) * | 2002-07-25 | 2005-06-24 | Oreal | COSMETIC USE OF LIGNANS |
FR2842731B1 (en) * | 2002-07-25 | 2005-12-30 | Oreal | USE OF LIGNANS TO PREVENT OR TREAT THE SIGNS OF SKIN AGING |
WO2004014886A1 (en) * | 2002-08-07 | 2004-02-19 | University Of Mississippi | Antigiardial agents and use thereof |
US20040131749A1 (en) * | 2002-08-29 | 2004-07-08 | Archer-Daniels-Midland Company | Phytochemicals from edible bean process streams |
FI114917B (en) * | 2002-08-29 | 2005-01-31 | Hormos Nutraceutical Oy Ltd | Lignaanikomplekseja |
US20060251750A1 (en) * | 2002-09-30 | 2006-11-09 | Tabor Aaron T | Soy formulations and their use in skin care |
KR20040038481A (en) * | 2002-11-01 | 2004-05-08 | 주식회사 렉스진바이오텍 | Health aid food containing isoflavone-containing extract from natural plant |
US20040097432A1 (en) * | 2002-11-04 | 2004-05-20 | Access Business Group International Llc. | Method of reducing cholesterol |
JP2004171733A (en) * | 2002-11-06 | 2004-06-17 | Alps Electric Co Ltd | Magnetic head, magnetic tape device including the same and method for producing the magnetic head |
WO2004043945A1 (en) * | 2002-11-12 | 2004-05-27 | Wiley Organics, Inc. | Method for purifying and separating soy isoflavones |
US20040254357A1 (en) * | 2002-12-19 | 2004-12-16 | Zaloga Gary P. | Fatty acid phenolic conjugates |
ITMI20022723A1 (en) * | 2002-12-20 | 2004-06-21 | Marfarma S R L Ora Marfarma Holding Spa | COMPOSITIONS FOR THE TREATMENT OF POST-MENOPAUSE SYNDROME. |
JP4442422B2 (en) * | 2002-12-24 | 2010-03-31 | 不二製油株式会社 | High-concentration and high-solubility isoflavone-containing composition and process for producing the same |
DE10300187B4 (en) * | 2003-01-08 | 2007-03-29 | Cognis Ip Management Gmbh | Chewing gum composition with herbal ingredients |
EP1471070A1 (en) * | 2003-04-22 | 2004-10-27 | Royal Schouten Group N.V. | Method for recovering a secondary plant metabolite |
NZ526098A (en) * | 2003-05-23 | 2005-10-28 | Enzo Nutraceuticals Ltd | Use of a plant extract containing flavonoids rich in proanthocyanidins for the prevention or treatment of migraine |
US7025998B2 (en) | 2003-05-30 | 2006-04-11 | Rotta Research Laboratorium S.P.A. | Phytoestrogens and probiotic for women's health |
US7718813B2 (en) | 2003-08-15 | 2010-05-18 | Nature Pure Labs Sw, Inc. | Hydrolysis and purification of active plant compounds suitable for topical application |
KR100751071B1 (en) * | 2003-10-10 | 2007-08-21 | 에스케이케미칼주식회사 | Triterpene compounds which are effective on improvement of brain function |
US20050202139A1 (en) * | 2003-11-05 | 2005-09-15 | Corbin David R. | Recovery of isoflavones from aqueous mixtures using zeolites or molecular sieves |
US7618671B2 (en) * | 2003-11-05 | 2009-11-17 | E.I. Du Pont De Nemours And Company | Recovery of isoflavones and removal of oligosaccharides from aqueous mixtures using zeolites |
US20050118290A1 (en) * | 2003-12-02 | 2005-06-02 | University Of Singapore | Compositions and method for treatment of steroid/nuclear receptor-mediated diseases |
JPWO2005063233A1 (en) * | 2003-12-26 | 2007-07-19 | 農工大ティー・エル・オー株式会社 | Composition for preventing and treating liver cancer |
US7557154B2 (en) * | 2004-12-23 | 2009-07-07 | Sabic Innovative Plastics Ip B.V. | Polymer compositions, method of manufacture, and articles formed therefrom |
CN1842327B (en) * | 2004-02-03 | 2011-05-11 | 株式会社红豆杉 | Therapeutic/preventive agent for osteoporosis containing as component isotaxiresinol derived from taxus yunnanensis |
US20050214367A1 (en) * | 2004-03-22 | 2005-09-29 | Volker Kuellmer | Processes for making coated phytochemicals and tocopherols and products formed therefrom |
US20050220978A1 (en) * | 2004-03-31 | 2005-10-06 | Cargill, Incorporated | Dispersible protein composition |
US8663679B2 (en) | 2004-04-29 | 2014-03-04 | Abbott Laboratories | Compositions for improving breast health in women |
US8377484B1 (en) | 2004-05-06 | 2013-02-19 | Maria V. Tsiper | Tumor encapsulation for prevention and treatment of metastatic cancer disease |
CN1305869C (en) * | 2004-05-21 | 2007-03-21 | 薛存宽 | Tech. for preparing isoflavone of red clover from red clover |
GB2414393B (en) * | 2004-05-24 | 2008-06-11 | Natraceutical Sa | Process for producing cocoa polyphenol concentrate |
BRPI0511227A (en) | 2004-06-04 | 2007-11-27 | Horizon Science Pty Ltd | molasses extract, sugar sludge extract, broth and / or foam extract collected from the clarification tank, extract of fibrous / residual sugarcane stalks from the sugar beet or sugarcane field, bagasse extract and extract of sugar beet pulp having characteristics reducing ig or burning rate; method for the extraction of non-nutrient phytochemicals which have reducing properties of ig or the rate of burning of sugar processing waste stream and other products in process and sugarcane milling sludge; method for decreasing the ig of a food product; sucrose product containing low ig; method for obtaining food products having a lower ig or lower burn rate; method to improve health; method for decreasing the ig of a sucrose-containing product; low ig product; purified phytochemical extracted from sugar cane or sugar beet; low ig sweetener and sweetener |
US20050288405A1 (en) * | 2004-06-29 | 2005-12-29 | General Electric Company | Copolymers containing diimide moieties and blends thereof |
US20060004151A1 (en) * | 2004-06-30 | 2006-01-05 | General Electric Company | Copolymers containing indan moieties and blends thereof |
US20060009506A1 (en) * | 2004-07-09 | 2006-01-12 | Odyssey Thera, Inc. | Drugs for the treatment of neoplastic disorders |
US7435431B2 (en) * | 2004-07-28 | 2008-10-14 | Abbott Laboratories | Method for controlling body weight in estrogen-insufficient women |
US7601370B2 (en) * | 2004-07-28 | 2009-10-13 | Abbott Laboratories | Method for controlling body weight in estrogen-insufficient women |
CN101005849A (en) * | 2004-07-28 | 2007-07-25 | 艾博特公司 | Nutritional compositions and methods for treating or preventing osteoporosis |
US20060045927A1 (en) * | 2004-08-25 | 2006-03-02 | Dajian Yang | Herbal formulations for modulating blood lipids |
EP1640001A1 (en) * | 2004-09-24 | 2006-03-29 | New Pharma Investments Holding | Composition against cardiovascular diseases |
US20060088617A1 (en) * | 2004-10-23 | 2006-04-27 | Mccurry James M | Chocolate composition and method for benefiting the cardiovascular system |
US20150005360A1 (en) | 2004-10-25 | 2015-01-01 | Nse Products, Inc. | Phytoestrogen compositions and associated methods |
DE102004060314A1 (en) * | 2004-12-08 | 2006-08-31 | Beiersdorf Ag | Active ingredient combinations of one or more isoflavonoids and carnitine and / or one or more acyl-carnitines |
BRPI0519851A2 (en) * | 2005-01-10 | 2017-05-30 | Hormos Medical Ltd | use of a lignan to manufacture a composition to prevent or alleviate symptoms related to estrogen deficiency |
US7595078B2 (en) * | 2005-03-15 | 2009-09-29 | Glanbia Nutritionals Ireland Limited | Methods of increasing flaxseed hull recovery and resultant flax products |
WO2006101268A1 (en) * | 2005-03-25 | 2006-09-28 | Seiren Co., Ltd. | Use of sericin for improvement in feeling of denture upon use |
US20060234948A1 (en) * | 2005-04-04 | 2006-10-19 | Empie Mark W | Lignan-containing compositions |
US7563464B1 (en) * | 2005-04-22 | 2009-07-21 | Bruce Eric Hudkins | Treatment of mucosal membranes utilizing phytoestrogen |
EP2450084B1 (en) | 2005-06-03 | 2014-02-19 | Horizon Science Pty Ltd | Substances having body mass redistribution properties |
WO2006134609A2 (en) * | 2005-06-16 | 2006-12-21 | Mmi Corporation | Novel anticancer agent, methods for obtaining the same and pharmaceutical compositions thereof |
JP2006347978A (en) * | 2005-06-17 | 2006-12-28 | Nippon Flour Mills Co Ltd | Anti-obesity agent, and food and pet food containing the same |
US7276257B2 (en) * | 2005-07-22 | 2007-10-02 | The Hong Kong University Of Science And Technology | Schisandrin B preparation |
MXPA05008573A (en) * | 2005-08-12 | 2007-02-12 | Leopoldo Espinosa Abdala | Isoflavones composition for treating menopause physiological symptoms and disorders. |
US7491414B2 (en) * | 2005-10-12 | 2009-02-17 | Gaia Herbs, Inc. | Anti-inflammatory substances extracted from Echinacea |
KR100715631B1 (en) * | 2005-12-29 | 2007-05-09 | 대한민국 | Production method of isoflavone enforced eggs |
CA2659272C (en) | 2006-07-28 | 2015-06-16 | Bioriginal Food & Science Corporation | Fat containing composition |
US20090263349A1 (en) * | 2006-08-03 | 2009-10-22 | Michael John Story | Methods and compositions for inhibiting angiogenesis |
JP2008044872A (en) * | 2006-08-11 | 2008-02-28 | Nippon Supplement Kk | Health food containing isolariciresinol, blood cholesterol-reducing agent and body fat-reducing agent |
CN101553582A (en) | 2006-09-19 | 2009-10-07 | 视界科技有限公司 | Extracts derived from sugar cane and a process for their manufacture |
US7718616B2 (en) | 2006-12-21 | 2010-05-18 | Zimmer Orthobiologics, Inc. | Bone growth particles and osteoinductive composition thereof |
KR100789169B1 (en) * | 2007-01-25 | 2008-01-16 | 네이쳐스메디신 주식회사 | Method for processing food containing flaxseed |
KR100844376B1 (en) * | 2007-02-07 | 2008-07-07 | 한국화학연구원 | Composition for preventing or treating osteoporosis comprising an extract of myristica fragrans or active compounds isolated therefrom |
JP5414192B2 (en) * | 2007-03-29 | 2014-02-12 | 江崎グリコ株式会社 | Circadian rhythm adjustment composition |
TW200841826A (en) * | 2007-04-20 | 2008-11-01 | Bion Tech Inc | Composition comprising five kinds of process fruit/vegetable |
US9114114B2 (en) | 2007-06-21 | 2015-08-25 | Mars, Inc. | Edible products having a high cocoa polyphenol content and improved flavor and the milled cocoa extracts used therein |
US8221803B1 (en) | 2007-06-25 | 2012-07-17 | OncoNatural Solutions, Inc. | Composition for prostate health |
US8053004B2 (en) * | 2007-10-08 | 2011-11-08 | Starmaker Products, Llc | Ointment for topical treatment of hot flashes and method of use |
US20090176871A1 (en) * | 2008-01-07 | 2009-07-09 | Schoenwetter Phillip E | Treatments for Domestic Animals Having Sex Hormone Deficiencies Using Soy Germ Isoflavones |
GB0801119D0 (en) | 2008-01-22 | 2008-02-27 | Barry Callebaut Ag | Composition |
EP2133080A1 (en) * | 2008-06-13 | 2009-12-16 | Haelan Schweiz GmbH | Compounds containing equol |
WO2010075418A2 (en) * | 2008-12-23 | 2010-07-01 | The Administrators Of The Tulane Educational Fund | Glyceollins suppress androgen-responsive prostate cancer |
EP2370072B1 (en) * | 2008-12-26 | 2017-06-28 | Natural Endotech Co., Ltd. | Phytoestrogenic compositions for preventing or treating symptoms associated with menopause |
AU2010241716B2 (en) | 2009-04-28 | 2013-07-04 | Wm. Wrigley Jr. Company | Oral compositions for skin benefits |
CN102802652B (en) | 2009-05-26 | 2014-09-10 | 株式会社爱茉莉太平洋 | Composition containing a bean extract for improving blood circulation and increasing vascular health |
CN103313733A (en) | 2010-11-15 | 2013-09-18 | 捷迈整形外科生物材料有限公司 | Bone void fillers |
IT1405432B1 (en) * | 2010-12-16 | 2014-01-10 | Funcional Food Res S R L | FUNCTIONAL FOOD PREPARATION AND RELATIVE USE. |
KR101266889B1 (en) * | 2011-01-13 | 2013-05-24 | 주식회사 보타메디 | Functional food compositions having the recovery effect of blood composition and function |
KR101229878B1 (en) * | 2011-02-07 | 2013-02-18 | 대한민국 | Composition for the treatment of alcoholism comprising a rice or its extracts |
CA2860448C (en) | 2011-02-08 | 2019-09-10 | Horizon Science Pty Ltd | Molasses extract enriched in polyphenols and uses thereof |
KR101428512B1 (en) * | 2012-03-09 | 2014-08-12 | 연세대학교 산학협력단 | A pharmaceutical composition for treating and preventing bonedisease containing methyl vanillate |
US20160038555A1 (en) * | 2011-03-31 | 2016-02-11 | Kang Yell Choi | Composition Containing Extracts of the Fruit of Hovenia Dulcis THUNB as an Active Ingredient for Preventing and Treating Bone Diseases |
US9433583B2 (en) | 2011-04-22 | 2016-09-06 | Frank J. Farrell | Colon vitamin |
JP6239622B2 (en) | 2012-08-28 | 2017-11-29 | ザ プロダクト メーカーズ (オーストラリア) プロプライエタリー リミテッド | Extraction method |
RU2510268C1 (en) * | 2012-11-14 | 2014-03-27 | ОБЩЕСТВО С ОГРАНИЧЕННОЙ ОТВЕТСТВЕННОСТЬЮ "Медресурс" | Agent for treating oestrogen-dependent cancer |
MX370090B (en) | 2013-02-01 | 2019-10-25 | Centro De Investig En Alimentacion Y Desarrollo A C | Method and system for the integral treatment of wastewater from the maize industry. |
EP3035949B1 (en) | 2013-08-16 | 2023-10-04 | Poly Gain Pte Ltd | Sugar cane derived extracts and uses |
ES2914673T3 (en) * | 2014-06-02 | 2022-06-15 | Thomas Nadackal Thomas | Water enriched with phytochemicals |
WO2017191886A1 (en) * | 2016-05-04 | 2017-11-09 | Phyto Corporation | Functionally reinforced desalted nutritional compositions from halophytes and preparation method thereof |
CN106478763A (en) * | 2016-09-27 | 2017-03-08 | 中国药科大学 | New estrogenic associated receptor alpha inhibitor and its medical usage |
TWI612899B (en) * | 2017-04-27 | 2018-02-01 | 行政院農業委員會農業藥物毒物試驗所 | Camellia seed extract and biopesticides with the same |
JP7346394B2 (en) | 2017-10-06 | 2023-09-19 | カーギル インコーポレイテッド | sense-altering compounds |
CA3135185A1 (en) | 2019-04-06 | 2020-10-15 | Cargill, Incorporated | Sensory modifiers |
US20220248707A1 (en) * | 2019-07-16 | 2022-08-11 | Advanced Female Technologies Llc | Chewing gum compositions for the treatment of menopausal symptoms |
CN112546058A (en) * | 2019-09-10 | 2021-03-26 | 百岳特生物技术(上海)有限公司 | Use of compounds that promote cholesterol metabolism |
RU2747147C1 (en) * | 2020-06-22 | 2021-04-28 | Федеральное государственное бюджетное учреждение "Национальный медицинский исследовательский центр онкологии имени Н.Н. Блохина" Министерства здравоохранения Российской Федерации (ФГБУ "НМИЦ онкологии им. Н.Н. Блохина" Минздрава России) | Pharmaceutical composition exhibiting cytotoxicity towards human colon carcinoma cells |
Family Cites Families (83)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB831306A (en) | 1955-01-13 | 1960-03-30 | British Soya Products Ltd | Improvements in processes for the production of baker's dough |
BE616786A (en) | 1961-04-26 | 1962-08-16 | Spofa Vereinigte Pharma Werke | Process for preparing a substance effective against inflammation |
US3391001A (en) | 1965-02-26 | 1968-07-02 | Griffith Laboratories | Production of flavorful protein hydrolysate |
US3870805A (en) | 1970-11-04 | 1975-03-11 | Staley Mfg Co A E | Process for preparing texturized protein compositions and the resulting product |
US3780182A (en) | 1971-01-18 | 1973-12-18 | Kraftco Corp | Method for imparting cheese-like flavor to proteinaceous materials |
GB1446965A (en) | 1974-02-14 | 1976-08-18 | Agricultural Vegetable Prod | Preparation of food products |
JPS5129280A (en) | 1974-08-12 | 1976-03-12 | Kikkoman Shoyu Co Ltd | Daizuno kakoshorihoho |
GB1575004A (en) * | 1976-03-23 | 1980-09-17 | Iverni Della Beffa Spa | Pharmacologically active polyphenolic substances |
US4264509A (en) | 1977-06-08 | 1981-04-28 | Z-L Limited Partnership | Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same |
US4157984A (en) * | 1977-06-08 | 1979-06-12 | Z-L Limited | Antioxidants, antioxidant compositions and methods of preparing and using same |
DE2900304C3 (en) | 1979-01-05 | 1981-11-05 | Dr. H.Schmittmann Gmbh, 5620 Velbert | Saponin extract product and process for its manufacture |
US4232122A (en) * | 1979-01-17 | 1980-11-04 | Z-L Limited Partnership | Antioxidants, antioxidant compositions and methods of preparing and using same |
US4366082A (en) | 1979-04-11 | 1982-12-28 | Z-L Limited Partnership | Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same |
US4390559A (en) | 1979-04-11 | 1983-06-28 | Z-L Limited Partnership | Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same |
US4366248A (en) | 1979-04-11 | 1982-12-28 | Z-L Limited Partnership | Fermentation method of preparing antioxidants |
DE3040246C2 (en) | 1979-10-29 | 1985-01-10 | Osaka Chemical Laboratory Co., Ltd., Osaka | Soy Saponins A ↓ 1 ↓ and A? 2? and their use |
JPS5933232A (en) | 1982-08-19 | 1984-02-23 | Tokiwa Kanpou Seiyaku:Kk | Separation of saponin and flavone from leguminous plant |
JPS5985265A (en) | 1982-11-04 | 1984-05-17 | Naganoken Kooridoufu Kogyo Kyodo Kumiai | Preparation of nutrient enriched food raw material |
US4557927A (en) | 1983-03-10 | 1985-12-10 | Kabushiki Kaisha Hoyashibara | Food products and process for producing same |
JPS6130593A (en) | 1984-07-20 | 1986-02-12 | Pelican:Kk | Method of extracting saponin component from soybeam hypocotyl |
JPS61100524A (en) | 1984-10-19 | 1986-05-19 | Junichi Iwamura | Method of separating saponin and flavone |
JPS6210018A (en) | 1985-07-04 | 1987-01-19 | Oruto Bioka Kenkyusho:Kk | Composition for suppressing obesity |
JPS62155082A (en) | 1985-12-27 | 1987-07-10 | Karupisu Shokuhin Kogyo Kk | Production of bifidus bacterium proliferation substance |
US4883788A (en) | 1986-06-06 | 1989-11-28 | Hauser-Kuhrts, Inc. | Method and composition for reducing serum cholesterol |
US4808574A (en) * | 1986-12-03 | 1989-02-28 | Nauchno-Issledovatelsky Institut Sadovodstva | Composition inhibiting pathological addiction to alcohol |
US4889921A (en) | 1987-04-29 | 1989-12-26 | The University Of Toronto Innovations Foundation | Production of rapeseed protein materials |
JPH01175942A (en) | 1987-12-28 | 1989-07-12 | Sanyo Kokusaku Pulp Co Ltd | Antiviral composition for pharmaceutical use |
JPH01312965A (en) | 1988-06-13 | 1989-12-18 | Toshiko Miyazaki | Soybean-containing toasted green tea |
IT1219732B (en) | 1988-06-28 | 1990-05-24 | Tecnofarmaci Spa | PROCYANIDOLIC OLIGOMERIC FRACTIONS, THEIR PREPARATION PROCEDURE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
JPH02188598A (en) | 1989-01-17 | 1990-07-24 | Nippon Mektron Ltd | Production of soyasaponin i |
JPH02261365A (en) | 1989-03-28 | 1990-10-24 | N I Inst Sadovodstva Vinogradars I Vinoderia | Soft drink for sthenia |
ATE96908T1 (en) | 1989-06-22 | 1993-11-15 | Univ Catholique Louvain | METHOD AND DEVICE FOR THE PREPARATION OF SAMPLES FOR THE CHEMICAL ANALYSIS OF LIQUIDS BY INFRARED SPECTROMETRY OF DRY EXTRACTS. |
GB2233450B (en) | 1989-06-24 | 1993-06-30 | Univ Wales Medicine | Detecting or quantifing multiple analytes with luminescent reagents |
CH679584A5 (en) * | 1989-11-10 | 1992-03-13 | Nestle Sa | |
JPH04152845A (en) | 1990-10-15 | 1992-05-26 | Shigekazu Ishimura | Coffee blended with soybean |
US5204369A (en) * | 1991-07-01 | 1993-04-20 | The Endowment For Research In Human Biology | Method for the inhibition of aldh-i useful in the treatment of alcohol dependence or alcohol abuse |
JPH05170756A (en) * | 1991-12-20 | 1993-07-09 | Kikkoman Corp | Production of isoflavone compound |
DE69333624T2 (en) | 1992-05-19 | 2005-09-15 | Novogen Research Pty. Ltd., North Ryde | USE OF ISOFLAVON PHYTO-ESTROGEN EXTRACTS OF SOY OR CLOVER |
CN1080864A (en) * | 1993-06-28 | 1994-01-19 | 沈阳药学院 | A kind of alcohol-decomposing powder and preparation method thereof |
CN1080863A (en) * | 1993-06-28 | 1994-01-19 | 沈阳药学院 | A kind of health medicine compositions of relieving the effect of alcohol |
DE4325532A1 (en) | 1993-07-29 | 1995-02-02 | Schwabe Willmar | Preparations of Crataegus species, medicinal products and their use for the prevention of sudden cardiac death and reperfusion-related cardiovascular damage |
BR9407822A (en) | 1993-10-12 | 1997-05-06 | Protein Tech Int | Process for the production of a vegetable protein whey enriched with isoflavone agglucone whey enriched with isoflavone agglucone whey protein enriched with isoflavone agglucone and a process for the recovery in a 50% monkeys curdled milk protein of an isoflavone from a vegetable protein material |
US5320949A (en) * | 1993-10-12 | 1994-06-14 | Protein Technologies International, Inc. | Process for producing aglucone isoflavone enriched vegetable protein fiber |
DE69429673T3 (en) * | 1993-10-12 | 2007-08-23 | Archer Daniels Midland Co., Decatur | An AGLUKON ISOFLAVON ENRICHED PLANT PROTEIN CONCENTRATE AND A METHOD OF MANUFACTURING THEREOF |
BR9407792A (en) * | 1993-10-12 | 1997-03-18 | Protein Tech Int | Process for producing an aglucone isoflavone-enriched extract from a vegetable protein material agglucone isoflavone-enriched protein isolate agglucone isoflavone enriched with vegetable protein isolate and process for recovering at least 50% of an isoflavone from a material of vegetable protein |
JPH07147903A (en) | 1993-11-29 | 1995-06-13 | Yamamoto Housuien:Kk | Food containing tea leaf |
CA2128293C (en) * | 1993-12-06 | 2002-09-03 | Masayuki Tanabe | Fruit polyphenols and medicinal compositions containing them |
IT1265312B1 (en) * | 1993-12-21 | 1996-10-31 | Indena Spa | FORMULATIONS CONTAINING CAROTENOIDS AND PRO-CAROTENOIDS ASSOCIATED WITH POLYPHENOLS IN THE PREVENTION OF DAMAGES FROM ABNORMAL PRODUCTION OF |
US5506211A (en) | 1994-05-09 | 1996-04-09 | The Uab Research Foundation | Genistein for use in inhibiting osteroclasts |
US5424331A (en) * | 1994-06-10 | 1995-06-13 | Bio-Virus Research Incorporated | Pharmaceutical compositions and dietary soybean food products for the prevention of osteoporosis |
JPH0873369A (en) | 1994-09-01 | 1996-03-19 | Fuairudo:Kk | Tea for health |
US5554645A (en) | 1994-10-03 | 1996-09-10 | Mars, Incorporated | Antineoplastic cocoa extracts and methods for making and using the same |
US5569459A (en) * | 1995-02-15 | 1996-10-29 | Bio-Virus Research Incorporated | Pharmaceutical compositions for the management of premenstrual syndrome and alleviation of menopausal disorders |
US5679806A (en) * | 1995-02-24 | 1997-10-21 | Hauser, Inc. | Process for the isolation and purification of isoflavones |
US5486631A (en) | 1995-06-14 | 1996-01-23 | Siltech Inc. | Silicone polymers for the modification of zinc oxide |
US5554519A (en) | 1995-08-07 | 1996-09-10 | Fermalogic, Inc. | Process of preparing genistein |
IL115110A (en) | 1995-08-30 | 1997-08-14 | Chajuss Daniel | Soy molasses |
US5547671A (en) * | 1995-09-20 | 1996-08-20 | Duthinh; Phu | Anti-intoxication composition |
US5968516A (en) * | 1995-10-03 | 1999-10-19 | Liu; Yaguang | Soybean drug and new method of extracting soybean saponins |
US5837256A (en) * | 1995-12-21 | 1998-11-17 | Clark; William F. | Method for treatment of Lupus nephritis |
WO1997032593A2 (en) | 1996-03-08 | 1997-09-12 | Energiser Plc | Composition containing iso-flavonoids and lignans |
US6261565B1 (en) | 1996-03-13 | 2001-07-17 | Archer Daniels Midland Company | Method of preparing and using isoflavones |
US6171638B1 (en) | 1996-03-13 | 2001-01-09 | Archer Daniels Midland Company | Production of isoflavone enriched fractions from soy protein extracts |
US6033714A (en) | 1996-03-13 | 2000-03-07 | Archer Daniels Midland Company | Process for production of isoflavone fractions from soy |
US6391310B1 (en) | 1996-03-13 | 2002-05-21 | Archer Daniels Midland Company | Method of preparing and using isoflavones for the treatment of neurological symptoms |
US5702752A (en) * | 1996-03-13 | 1997-12-30 | Archer Daniels Midland Company | Production of isoflavone enriched fractions from soy protein extracts |
US6045819A (en) * | 1996-04-10 | 2000-04-04 | Nichimo Co., Ltd. | Substance containing health-promoting component and process for the production thereof |
AU3887597A (en) | 1996-07-18 | 1998-02-10 | Nutricor, Inc. | Nutritious food preparations and methods for making them |
JP3424476B2 (en) | 1996-11-05 | 2003-07-07 | 不二製油株式会社 | Drinking material |
JP3883018B2 (en) * | 1997-02-06 | 2007-02-21 | キッコーマン株式会社 | Method for producing isoflavone compound |
EP0922395A4 (en) * | 1997-04-01 | 1999-12-22 | Nichimo Kk | Product comprising health-promotive ingredient and process for producing the same |
JPH10312965A (en) | 1997-05-13 | 1998-11-24 | Mitsubishi Heavy Ind Ltd | Plasma chemical deposition system |
JP3998293B2 (en) | 1997-06-18 | 2007-10-24 | 株式会社ヤクルト本社 | Helicobacter pylori inhibitor |
CN1089245C (en) * | 1997-07-30 | 2002-08-21 | 因迪纳有限公司 | Soya extract, process for its prepn. and pharmaceutical compsn. |
US5855892A (en) * | 1997-09-19 | 1999-01-05 | Potter; Susan M. | Method for decreasing LDL-cholesterol concentration and increasing HDL-cholesterol concentration in the blood to reduce the risk of atherosclerosis and vascular disease |
US5952374A (en) * | 1997-09-29 | 1999-09-14 | Protein Technologies International, Inc. | Method for inhibiting the development of Alzheimer's disease and related dementias- and for preserving cognitive function |
US5904924A (en) * | 1997-11-04 | 1999-05-18 | Oncologics, Inc. | Green nutritional powder composition |
EP1051171A1 (en) * | 1998-01-28 | 2000-11-15 | Dusan Miljkovic | Isoflavanoid formulations for oral administration |
AU3899199A (en) * | 1998-05-12 | 1999-11-29 | Endowment for Research in Human Biology, Inc., The | Methods and assays useful in the treatment of alcohol dependence or alcohol abuse |
CN1184895C (en) * | 1998-07-16 | 2005-01-19 | 阿龙·塔博尔 | Soy formulations and their use for promoting health |
JP2000095792A (en) * | 1998-09-21 | 2000-04-04 | Showa Sangyo Co Ltd | Acquisition of isoflavone composition comprising genistin |
US6592910B1 (en) * | 1999-04-20 | 2003-07-15 | Board Of Trustees, Southern Illinois University | Methods of treating clinical diseases with isoflavones |
US6319308B1 (en) | 2000-12-21 | 2001-11-20 | Mccomas Edward | Coating compositions containing nickel and boron and particles |
-
1998
- 1998-09-28 US US09/162,038 patent/US6261565B1/en not_active Expired - Lifetime
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- 1998-10-02 PT PT98308060T patent/PT906761E/en unknown
- 1998-10-02 AT AT98308060T patent/ATE270894T1/en active
- 1998-10-02 ES ES98308060T patent/ES2224337T3/en not_active Expired - Lifetime
- 1998-10-02 EP EP98308060A patent/EP0906761B1/en not_active Expired - Lifetime
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- 1998-10-02 DK DK98308060T patent/DK0906761T3/en active
- 1998-10-02 KR KR1019980041946A patent/KR19990066785A/en not_active Application Discontinuation
- 1998-10-02 JP JP10296187A patent/JPH11221048A/en active Pending
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- 1999-04-27 HK HK99101886A patent/HK1016879A1/en not_active IP Right Cessation
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- 2002-05-01 US US10/136,103 patent/US20020168433A1/en not_active Abandoned
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