JPH04283518A - Agent for alleviating periodontosis - Google Patents
Agent for alleviating periodontosisInfo
- Publication number
- JPH04283518A JPH04283518A JP3070389A JP7038991A JPH04283518A JP H04283518 A JPH04283518 A JP H04283518A JP 3070389 A JP3070389 A JP 3070389A JP 7038991 A JP7038991 A JP 7038991A JP H04283518 A JPH04283518 A JP H04283518A
- Authority
- JP
- Japan
- Prior art keywords
- periodontosis
- alleviating
- agent
- genistein
- growth
- 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.)
- Pending
Links
- 208000010266 Aggressive Periodontitis Diseases 0.000 title abstract 5
- 201000006727 periodontosis Diseases 0.000 title abstract 5
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 claims description 10
- 235000006539 genistein Nutrition 0.000 claims description 10
- 229940045109 genistein Drugs 0.000 claims description 10
- 241000894006 Bacteria Species 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- ZCOLJUOHXJRHDI-FZHKGVQDSA-N Genistein 7-O-glucoside Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)c1cc(O)c2C(=O)C(c3ccc(O)cc3)=COc2c1 ZCOLJUOHXJRHDI-FZHKGVQDSA-N 0.000 abstract 1
- CJPNHKPXZYYCME-UHFFFAOYSA-N Genistin Natural products OCC1OC(Oc2ccc(O)c3OC(=CC(=O)c23)c4ccc(O)cc4)C(O)C(O)C1O CJPNHKPXZYYCME-UHFFFAOYSA-N 0.000 abstract 1
- YCUNGEJJOMKCGZ-UHFFFAOYSA-N Pallidiflorin Natural products C1=CC(OC)=CC=C1C1=COC2=CC=CC(O)=C2C1=O YCUNGEJJOMKCGZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000605862 Porphyromonas gingivalis Species 0.000 abstract 1
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 8
- 241000606125 Bacteroides Species 0.000 description 6
- 229930182470 glycoside Natural products 0.000 description 6
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 6
- 235000008696 isoflavones Nutrition 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 235000007240 daidzein Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000028169 periodontal disease Diseases 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- -1 isoflavone glycosides Chemical class 0.000 description 3
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 2
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000004195 gingiva Anatomy 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 2
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 241000190888 Capnocytophaga gingivalis Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000002587 anti-hemolytic effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 230000002554 disease preventive effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002515 isoflavone derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000013322 soy milk Nutrition 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、抗歯周症剤に関するも
のである。TECHNICAL FIELD The present invention relates to an antiperiodontal agent.
【０００２】0002
【従来の技術及び課題】う蝕（むし歯）や歯周症（歯槽
膿漏等）には多くの人が悩まされており、その内歯周症
は気道、腸管などの常在細菌であるバクテロイデス・ジ
ンジバリス（Ｂａｃｔｅｒｏｉｄｅｓ ｇｉｎｇｉｖａ
ｌｉｓ）を主とする嫌気性細菌により惹起されるとみな
されている。[Prior Art and Problems] Many people suffer from caries (cavities) and periodontal disease (alveolar pyorrhea, etc.), and periodontal disease is caused by Bacteroides, which is a resident bacteria in the respiratory tract and intestinal tract.・Bacteroides gingiva
It is considered to be caused by anaerobic bacteria, mainly lis.
【０００３】従って歯周症の予防にはＢａｃｔｅｒｏｉ
ｄｅｓ ｇｉｎｇｉｖａｌｉｓの口腔内での増殖を抑え
ること（抗菌）が最も重要であり、かつ効果的である。
この為には抗菌あるいは殺菌作用のある薬剤を投与し該
菌を駆逐する方法がある。[0003] Therefore, for the prevention of periodontal disease, Bacteroi
Suppressing the growth of C. des gingivalis in the oral cavity (antibacterial) is most important and effective. For this purpose, there is a method of administering drugs with antibacterial or bactericidal effects to exterminate the bacteria.
【０００４】しかしながら薬剤の投与は副作用の危険が
指摘されており、安全性の高い歯周症予防剤の開発が望
まれているところである。また、大豆中のサポニン及び
イソフラボンを代表とする配糖体及びその非糖区分（ア
グリコン）は各種生理作用、例えば、抗酸化、抗溶血作
用あるいは抗カビ作用等を有することが知られているが
、これらの生理作用は配糖体あるいはアグリコンに共通
するものであり、例えばゲニステイン及びダイゼインは
共にカビの増殖を阻害することが報告されている。[0004] However, it has been pointed out that there is a risk of side effects when administering drugs, and there is a desire to develop highly safe periodontal disease preventive agents. In addition, glycosides and their non-sugar components (aglycones), typified by saponins and isoflavones, in soybeans are known to have various physiological effects, such as antioxidative, antihemolytic, and antifungal effects. These physiological actions are common to glycosides or aglycones; for example, it has been reported that both genistein and daidzein inhibit the growth of fungi.
【０００５】[0005]
【課題を解決するための手段】本発明者等は大豆から得
られるイソフラボン配糖体あるいはアグリコンの入手容
易性、安全性に着目し、検討を進めたところ、アグリコ
ンの中でもゲニステインのみがＢａｃｔｅｒｏｉｄｅｓ
ｇｉｎｇｉｖａｌｉｓの増殖抑制に効果があり、ダイ
ゼインにはその効果がほとんど見られないという知見を
得た。前述の如く大豆中のアグリコンあるいはその配糖
体の生理作用の多くは共通するものであるが、Ｂａｃｔ
ｅｒｏｉｄｅｓ ｇｉｎｇｉｖａｌｉｓの増殖抑制効果
はゲニステインのみにしか見ることができない特異的な
ものであり、この様な知見は本発明者等によって初めて
明らかにされたものである。[Means for Solving the Problems] The present inventors focused on the availability and safety of isoflavone glycosides or aglycones obtained from soybeans, and as a result of their investigation, they found that among the aglycones, only genistein is Bacteroides.
It was found that daidzein is effective in inhibiting the proliferation of C. gingivalis, while daidzein has almost no effect. As mentioned above, many of the physiological effects of aglycones or their glycosides in soybeans are common, but Bact.
The growth-inhibiting effect of eroides gingivalis is specific and can only be seen with genistein, and this finding was first revealed by the present inventors.
【０００６】本発明はこの様な知見に基づいて完成され
たものであり、以下に本発明を具体的に説明する。ゲニ
ステインは植物体、例えば大豆から抽出して得られるも
のであり、具体的には特開昭６２−１２６１８６号に開
示された方法、あるいはこの方法で得られたイソフラボ
ン配糖体を、酵素ないし酸で加水分解したアグリコンを
樹脂に吸着させたのちゲニステインを選択的に溶出させ
たり、アグリコン混合物を乾燥させた後エーテル抽出す
ることによって得ることができる。また本発明者等が先
に特許出願した特願昭６３−８３１３５号に開示した方
法によっても得ることができる。The present invention has been completed based on such knowledge, and will be specifically explained below. Genistein is obtained by extracting it from plants such as soybeans. Specifically, it is obtained by the method disclosed in JP-A No. 62-126186, or isoflavone glycosides obtained by this method are extracted with enzymes or acids. It can be obtained by adsorbing the hydrolyzed aglycone on a resin and then selectively eluting genistein, or by drying the aglycone mixture and then extracting it with ether. It can also be obtained by the method disclosed in Japanese Patent Application No. 63-83135, which was previously filed by the present inventors.
【０００７】更には、脱皮大豆をｐＨ ８〜１１、５０
〜６０℃の温水に浸漬し、イソフラボン配糖体を抽出し
、これを酵素ないし酸で加水分解した分解物あるいは豆
乳を限外濾過膜により濾過して得られるイソフラボン含
有区分や、分離大豆蛋白製造過程で得られる非蛋白区分
中のイソフラボン含有区分を、酸ないし酵素で加水分解
した分解物をそのままあるいは濃縮したものでも良い。
この様にして得られるゲニステインはそのままの形で口
腔内に適用してもよく、あるいは他の口腔剤、例えば歯
磨剤、うがい剤、チューインガム、トローチ等に混合し
ても良い。
以下に実験例を示す。[0007] Furthermore, the pH of dehulled soybeans is 8 to 11, 50.
The isoflavone-containing fraction obtained by soaking in warm water of ~60℃ to extract isoflavone glycosides and hydrolyzing this with enzymes or acids, or by filtering soymilk through an ultrafiltration membrane, and the production of isolated soybean protein. The isoflavone-containing fraction in the non-protein fraction obtained in the process may be hydrolyzed with acid or enzyme, and the decomposition product may be used as it is or as a concentrated product. The genistein thus obtained may be applied to the oral cavity as it is, or may be mixed into other oral preparations, such as dentifrices, gargles, chewing gums, and troches. An experimental example is shown below.
【０００８】[0008]
【実験例】Ｂａｃｔｅｒｏｉｄｅｓ ｇｉｎｇｉｖａｌ
ｉｓの増殖抑制効果について以下の実験を行なった。日
水製薬株式会社のＧＡＭブイヨンの半流動培地（５．９
％）に第１表に示す濃度でゲニステイン及びダイゼイン
を添加したのち１２０℃、１５分間の殺菌処理をし、こ
の培地１０ｍｌにＢａｃｔｅｒｏｉｄｅｓ ｇｉｎｇｉ
ｖａｌｉｓ３８１を３白金耳添加し、３７℃で４８〜７
８時間培養したところ、表１に示す結果を得た。尚、表
中−は生育が認められなかったものを示し、＋は生育が
認められたものを示す。＋が多いほど生育の旺盛なこと
を表わしている。[Experiment example] Bacteroides gingival
The following experiment was conducted regarding the growth-inhibiting effect of is. Nissui Pharmaceutical Co., Ltd. GAM broth semi-solid medium (5.9
%) was added with genistein and daidzein at the concentrations shown in Table 1, sterilized at 120°C for 15 minutes, and Bacteroides gingi was added to 10 ml of this medium.
Add 3 platinum loops of valis381 and heat at 37℃ for 48~7
After culturing for 8 hours, the results shown in Table 1 were obtained. In the table, - indicates that no growth was observed, and + indicates that growth was observed. The more +, the more vigorous the growth.
【０００９】[0009]
【発明の効果】表１に示す結果から明らかなように、ゲ
ニステインはＢａｃｔｅｒｏｉｄｅｓ ｇｉｎｇｉｖａ
ｌｉｓの増殖を抑制する特異な効果を有する。それ故、
ゲニステインは抗歯周症剤の有効成分として利用できる
ものである。[Effects of the Invention] As is clear from the results shown in Table 1, genistein is produced by Bacteroides gingiva.
It has a unique effect of suppressing the proliferation of lis. Therefore,
Genistein can be used as an active ingredient in anti-periodontal agents.
Claims (1)
。[Claim 1] An anti-periodontal agent containing genistein as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3070389A JPH04283518A (en) | 1991-03-12 | 1991-03-12 | Agent for alleviating periodontosis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3070389A JPH04283518A (en) | 1991-03-12 | 1991-03-12 | Agent for alleviating periodontosis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04283518A true JPH04283518A (en) | 1992-10-08 |
Family
ID=13430042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3070389A Pending JPH04283518A (en) | 1991-03-12 | 1991-03-12 | Agent for alleviating periodontosis |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04283518A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0795553A1 (en) * | 1996-03-13 | 1997-09-17 | Archer-Daniels-Midland Company | Production of isoflavone enriched fractions from soy protein extracts |
| EP0812837A1 (en) * | 1996-06-11 | 1997-12-17 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| WO1999044440A1 (en) * | 1998-03-04 | 1999-09-10 | Sunstar Inc. | Food compositions for preventing periodontosis or preventing the progression of periodontosis and method for preventing or treating periodontosis |
| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6132795A (en) * | 1998-03-15 | 2000-10-17 | Protein Technologies International, Inc. | Vegetable protein composition containing an isoflavone depleted vegetable protein material with an isoflavone containing material |
| JP2002121146A (en) * | 2000-10-13 | 2002-04-23 | Sunstar Inc | Preparation for preventing periodontal disease |
| EP1021177A4 (en) * | 1997-02-04 | 2002-05-15 | John V Kosbab | Compositions and methods for prevention and treatment of vascular degenerative diseases |
| US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
| WO2003075943A3 (en) * | 2002-03-06 | 2004-04-22 | Sophie Chen Ph D | Botanical extract compositions with anti-cancer or phytoestrogenic activity comprising wogonin, isoliquiritigenin and/or coumestrol |
| US7285297B1 (en) | 1999-04-23 | 2007-10-23 | Archer-Daniels-Midland Company | Method of reducing low density liproprotein cholesterol concentration |
| WO2008155890A1 (en) * | 2007-06-21 | 2008-12-24 | J-Oil Mills, Inc. | Method for producing glycoside aglycone |
| EP1669080A4 (en) * | 2003-09-19 | 2009-04-22 | Sunstar Inc | Method of inhibiting alveolar resorption and peridental membrane loss and composition for internal use to be used therein |
| US7897144B2 (en) | 2001-02-28 | 2011-03-01 | Johnson & Johnson Comsumer Companies, Inc. | Compositions containing legume products |
| WO2012043743A1 (en) * | 2010-09-30 | 2012-04-05 | 国立大学法人広島大学 | Anti-bacterial composition and use thereof |
Citations (4)
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|---|---|---|---|---|
| JPS59187746A (en) * | 1983-04-11 | 1984-10-24 | Hayashibara Biochem Lab Inc | Beverage and its preparation |
| JPS61275224A (en) * | 1985-05-29 | 1986-12-05 | Sunstar Inc | Collagenase-inhibiting agent |
| JPS62286926A (en) * | 1986-06-05 | 1987-12-12 | Sunstar Inc | Collagenase inhibitor |
| JPH01258669A (en) * | 1988-04-06 | 1989-10-16 | Kikkoman Corp | Production of isoflavon compound |
-
1991
- 1991-03-12 JP JP3070389A patent/JPH04283518A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59187746A (en) * | 1983-04-11 | 1984-10-24 | Hayashibara Biochem Lab Inc | Beverage and its preparation |
| JPS61275224A (en) * | 1985-05-29 | 1986-12-05 | Sunstar Inc | Collagenase-inhibiting agent |
| JPS62286926A (en) * | 1986-06-05 | 1987-12-12 | Sunstar Inc | Collagenase inhibitor |
| JPH01258669A (en) * | 1988-04-06 | 1989-10-16 | Kikkoman Corp | Production of isoflavon compound |
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0795553A1 (en) * | 1996-03-13 | 1997-09-17 | Archer-Daniels-Midland Company | Production of isoflavone enriched fractions from soy protein extracts |
| US6664382B2 (en) | 1996-06-11 | 2003-12-16 | Solae, Llc | Recovery of isoflavones from soy molasses |
| EP0812837A1 (en) * | 1996-06-11 | 1997-12-17 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| EP1659119A1 (en) * | 1996-06-11 | 2006-05-24 | Archer-Daniels-Midland Company | Recovery of isoflavones from soy molasses |
| US5990291A (en) * | 1996-06-11 | 1999-11-23 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6706292B2 (en) | 1996-06-11 | 2004-03-16 | Solae, Llc | Recovery of isoflavones from soy molasses |
| EP1659118A1 (en) * | 1996-06-11 | 2006-05-24 | Archer-Daniels-Midland Company | Recovery of isoflavones from soy molasses |
| US6323018B1 (en) | 1996-06-11 | 2001-11-27 | Protein Technologies Int'l Lnc. | Recovery of isoflavones from soy molasses |
| US5919921A (en) * | 1996-06-11 | 1999-07-06 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6680381B1 (en) | 1996-06-11 | 2004-01-20 | Solae, Llc | Recovery of isoflavones from soy molasses |
| US6495141B2 (en) | 1996-06-11 | 2002-12-17 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| EP1021177A4 (en) * | 1997-02-04 | 2002-05-15 | John V Kosbab | Compositions and methods for prevention and treatment of vascular degenerative diseases |
| WO1999044440A1 (en) * | 1998-03-04 | 1999-09-10 | Sunstar Inc. | Food compositions for preventing periodontosis or preventing the progression of periodontosis and method for preventing or treating periodontosis |
| US6132795A (en) * | 1998-03-15 | 2000-10-17 | Protein Technologies International, Inc. | Vegetable protein composition containing an isoflavone depleted vegetable protein material with an isoflavone containing material |
| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
| US6572876B2 (en) | 1999-04-23 | 2003-06-03 | Solae, Llc | Administering a composition containing plant sterol, soy protein and isoflavone for reducing LDL-cholesterol |
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