CN1210407C - 富含配基异黄酮的植物蛋白提取物和蛋白物质,高染料木黄酮和黄豆苷原含量的物质的制备方法 - Google Patents
富含配基异黄酮的植物蛋白提取物和蛋白物质,高染料木黄酮和黄豆苷原含量的物质的制备方法 Download PDFInfo
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
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-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J3/00—Working-up of proteins for foodstuffs
- A23J3/14—Vegetable proteins
- A23J3/16—Vegetable proteins from soybean
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
- A23L11/05—Mashed or comminuted pulses or legumes; Products made therefrom
- A23L11/07—Soya beans, e.g. oil-extracted soya bean flakes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
- A23L11/30—Removing undesirable substances, e.g. bitter substances
- A23L11/33—Removing undesirable substances, e.g. bitter substances using enzymes; Enzymatic transformation of pulses or legumes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
- A23L11/30—Removing undesirable substances, e.g. bitter substances
- A23L11/34—Removing undesirable substances, e.g. bitter substances using chemical treatment, adsorption or absorption
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Botany (AREA)
- Agronomy & Crop Science (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
样品 | 染料 | 6”- | 6”- | 染料 | 黄豆 | 6”- | 6”- | 黄豆 | 大豆 | 6”- | 黄豆 |
木苷 | OMal | OAc | 木黄 | 苷 | OMal | OAc | 苷原 | 异黄 | OMal | 黄素 | |
染料 | 染料 | 酮 | 黄豆 | 黄豆 | 酮 | 大豆 | |||||
木苷 | 木苷 | 苷 | 苷 | 异黄 | |||||||
酮 |
样品 | 染料 | 6”-OMal | 6”-OAc | 染料木黄 | 黄豆苷 | 6”-OMal | 6”-OAc | 黄豆苷原 | 大豆异黄 | 6”-OM | 黄豆黄素 |
木苷 | 染料木苷 | 染料木苷 | 酮 | 黄豆苷 | 黄豆苷 | 酮 | al大豆异黄酮 |
样品 | 染料 | 6”- | 6”- | 染料 | 黄豆 | 6”- | 6”- | 黄豆 | 大豆 | 6”- | 黄豆 |
木苷 | OMal | OAc | 木黄 | 苷 | OMal | OAc | 苷原 | 异黄 | OMal | 黄素 | |
染料木苷 | 染料木苷 | 酮 | 黄豆苷 | 黄豆苷 | 酮 | 大豆异黄酮 |
Claims (44)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/709,026 US5726034A (en) | 1996-09-06 | 1996-09-06 | Aglucone isoflavone enriched vegetable protein extract and protein material, and high genistein and daidzein content materials and process for producing the same |
US709026 | 1996-09-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1183475A CN1183475A (zh) | 1998-06-03 |
CN1210407C true CN1210407C (zh) | 2005-07-13 |
Family
ID=24848181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB971205868A Expired - Fee Related CN1210407C (zh) | 1996-09-06 | 1997-09-05 | 富含配基异黄酮的植物蛋白提取物和蛋白物质,高染料木黄酮和黄豆苷原含量的物质的制备方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US5726034A (zh) |
EP (1) | EP0827698B2 (zh) |
JP (1) | JPH1099089A (zh) |
KR (1) | KR100412116B1 (zh) |
CN (1) | CN1210407C (zh) |
AT (1) | ATE192284T1 (zh) |
AU (1) | AU718810B2 (zh) |
BR (1) | BR9704589A (zh) |
CA (1) | CA2214665C (zh) |
DE (1) | DE69701842T3 (zh) |
DK (1) | DK0827698T4 (zh) |
ES (1) | ES2147660T5 (zh) |
PT (1) | PT827698E (zh) |
RU (1) | RU2152434C1 (zh) |
TW (1) | TW574225B (zh) |
Families Citing this family (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE40792E1 (en) * | 1992-05-19 | 2009-06-23 | Novogen Research Pty Ltd | Health supplements containing phyto-oestrogens, analogues or metabolites thereof |
US6140469A (en) * | 1993-10-12 | 2000-10-31 | Protein Technologies International, Inc. | Protein isolate having an increased level of isoflavone compounds and process for producing the same |
US5827682A (en) * | 1995-06-07 | 1998-10-27 | Protein Technologies International, Inc. | Two-step conversion of vegetable protein isoflavone conjugates to aglucones |
US5821361A (en) | 1996-06-11 | 1998-10-13 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
US6579561B2 (en) | 1996-08-09 | 2003-06-17 | Protein Technologies International, Inc. | Aglucone isoflavone enriched vegetable flour and vegetable grit and process for making the same from a vegetable material containing isoflavone |
US6521282B1 (en) | 1996-08-09 | 2003-02-18 | Protein Technologies International, Inc. | Aglucone isoflavone enriched vegetable flour and grit |
AUPO203996A0 (en) * | 1996-08-30 | 1996-09-26 | Novogen Research Pty Ltd | Therapeutic uses |
JP3883018B2 (ja) * | 1997-02-06 | 2007-02-21 | キッコーマン株式会社 | イソフラボン化合物の製造方法 |
US6146668A (en) | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
WO1998050026A1 (en) * | 1997-05-01 | 1998-11-12 | Novogen Inc | Treatment or prevention of menopausal symptoms and osteoporosis |
US5834605A (en) * | 1997-07-07 | 1998-11-10 | Liu; Yaguang | Safe pharmaceutical composition for treating and preventing alcohol abuse and increasing immune function |
US6369200B2 (en) | 1997-10-15 | 2002-04-09 | Central Soya Company, Inc. | Soy isoflavone concentrate process and product |
US6228993B1 (en) | 1998-10-12 | 2001-05-08 | Central Soya Company, Inc. | Soy isoflavone concentrate process and product |
US6320028B1 (en) | 1997-10-15 | 2001-11-20 | Central Soya Company, Inc. | Soy isoflavone concentrate process and product |
KR100413025B1 (ko) * | 1997-10-20 | 2004-04-29 | 솔레 엘엘씨 | 아글루콘이소플라본강화식물성단백질유장,유장단백질재료,아글루콘이소플라본재료,제니스테인함량이높은재료및디아드제인함량이높은재료및식물성단백질유장으로부터이들을제조하는방법 |
AUPP112497A0 (en) * | 1997-12-24 | 1998-01-22 | Novogen Research Pty Ltd | Compositions and method for protecting skin from UV induced immunosupression and skin damage |
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 |
AUPP260798A0 (en) * | 1998-03-26 | 1998-04-23 | Novogen Research Pty Ltd | Treatment of medical related conditions with isoflavone containing extracts of clover |
US5994508A (en) * | 1998-04-13 | 1999-11-30 | Protein Technologies International, Inc. | Isoflavone rich protein isolate and process for producing |
US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
US6013771A (en) * | 1998-06-09 | 2000-01-11 | Protein Technologies International, Inc. | Isoflavone rich protein isolate and process for producing |
US6150399A (en) | 1998-06-30 | 2000-11-21 | Abbott Laboratories | Soy-based nutritional products |
JP4070177B2 (ja) | 1998-09-30 | 2008-04-02 | 天野エンザイム株式会社 | 新規な酵素組成物、その製造法及び用途 |
US6703051B1 (en) | 1998-10-13 | 2004-03-09 | Solae, Llc | Process for separating and recovering protein and isoflavones from a plant material |
DE69908809D1 (de) | 1998-11-25 | 2003-07-17 | Nutri Pharma Asa Oslo | Verwendung einer zusammensetzung enthaltend sojaprotein, diätfasern und phytoestrogen zur vorbeugung und/oder behandlung von lungenerkrankungen |
AU767245B2 (en) | 1998-11-25 | 2003-11-06 | Nutri Pharma Asa | Composition comprising soy protein, dietary fibres and a phytoestrogen compound and use thereof in the prevention and/or treatment of cardiovascular diseases |
BR9915896A (pt) * | 1998-12-02 | 2001-08-21 | Cognis Corp | Processos para recuperar valores de isoflavona a partir de um material de planta e a partir de uma biomassa |
US7285297B1 (en) | 1999-04-23 | 2007-10-23 | Archer-Daniels-Midland Company | Method of reducing low density liproprotein cholesterol concentration |
US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
AUPQ266199A0 (en) * | 1999-09-06 | 1999-09-30 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
US20090233999A1 (en) * | 1999-09-06 | 2009-09-17 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
KR20010007901A (ko) * | 1999-10-20 | 2001-02-05 | 서주원 | 귀리 유래의 베타-글루코시다제 및 그를 이용한제니스테인 또는 다이드제인의 제조 방법 |
AU769173B2 (en) * | 1999-12-15 | 2004-01-15 | Amino Up Co., Ltd. | Novel substance originating in basidiomycete culture, process for producing the same and use thereof |
JP4413464B2 (ja) * | 1999-12-17 | 2010-02-10 | 光則 小野 | 水溶性の豆ベース抽出物 |
AUPQ504300A0 (en) | 2000-01-11 | 2000-02-03 | Biorex Health Limited | Extraction of flavonoids |
BR0107486A (pt) * | 2000-01-11 | 2002-10-08 | Biorex Health Ltd | Método de extração de uma aglicona flavonóide a partir de material inicial contendo uma glicosida flavonóide e/ou conjugado dela proveniente |
AUPQ520300A0 (en) * | 2000-01-21 | 2000-02-17 | Novogen Research Pty Ltd | Food product and process |
AU4463101A (en) * | 2000-03-29 | 2001-10-08 | Amano Enzyme Inc | Process for producing aglycon by using diglycosidase and flavor-improved food containing the aglycon and converting agent to be used in the process |
JP2001302689A (ja) * | 2000-04-19 | 2001-10-31 | Protein Technol Internatl Inc | 植物材料からタンパクおよびイソフラボン類を分離回収する方法 |
EP1174144A1 (en) * | 2000-07-20 | 2002-01-23 | Linnea S.A. | Dry extract rich in isoflavones and process of preparation |
AUPR363301A0 (en) * | 2001-03-08 | 2001-04-05 | Novogen Research Pty Ltd | Dimeric isoflavones |
AU2002344683B2 (en) * | 2001-06-29 | 2007-08-23 | Maabarot Project Launching And Management Ltd | "Flavonoid concentrates" |
AUPR602201A0 (en) * | 2001-06-29 | 2001-07-26 | Biorex Health Limited | Flavonoid concentrates |
WO2004009035A2 (en) | 2002-07-24 | 2004-01-29 | Children's Hospital Medical Center | Compositions and products containing enantiomeric equol, and methods for their making |
US8668914B2 (en) * | 2002-07-24 | 2014-03-11 | Brigham Young University | Use of equol for treating skin diseases |
US20050249865A1 (en) * | 2002-08-05 | 2005-11-10 | Xinqi Liu | Process for producing soy protein |
AU2005239984B2 (en) * | 2002-10-29 | 2010-06-03 | Brigham Young University | Use of equol for treating skin diseases |
EP1569636B1 (en) | 2002-10-29 | 2017-12-13 | Colorado State University Research Foundation | Use of equol for treating androgen mediated diseases |
US8580846B2 (en) | 2002-10-29 | 2013-11-12 | Brigham Young University | Use of equol for ameliorating or preventing neuropsychiatric and neurodegenerative diseases or disorders |
KR100449887B1 (ko) * | 2003-10-31 | 2004-09-22 | 주식회사 렉스진바이오텍 | 이소플라본을 함유하는 괴각 추출물의 제조방법 |
EP2947592B1 (en) | 2007-09-24 | 2021-10-27 | Apple Inc. | Embedded authentication systems in an electronic device |
US8600120B2 (en) | 2008-01-03 | 2013-12-03 | Apple Inc. | Personal computing device control using face detection and recognition |
US20090176871A1 (en) * | 2008-01-07 | 2009-07-09 | Schoenwetter Phillip E | Treatments for Domestic Animals Having Sex Hormone Deficiencies Using Soy Germ Isoflavones |
US9002322B2 (en) | 2011-09-29 | 2015-04-07 | Apple Inc. | Authentication with secondary approver |
US8769624B2 (en) | 2011-09-29 | 2014-07-01 | Apple Inc. | Access control utilizing indirect authentication |
US9898642B2 (en) | 2013-09-09 | 2018-02-20 | Apple Inc. | Device, method, and graphical user interface for manipulating user interfaces based on fingerprint sensor inputs |
US10043185B2 (en) | 2014-05-29 | 2018-08-07 | Apple Inc. | User interface for payments |
DK179186B1 (en) | 2016-05-19 | 2018-01-15 | Apple Inc | REMOTE AUTHORIZATION TO CONTINUE WITH AN ACTION |
DK179471B1 (en) | 2016-09-23 | 2018-11-26 | Apple Inc. | IMAGE DATA FOR ENHANCED USER INTERACTIONS |
EP4156129A1 (en) | 2017-09-09 | 2023-03-29 | Apple Inc. | Implementation of biometric enrollment |
KR102185854B1 (ko) | 2017-09-09 | 2020-12-02 | 애플 인크. | 생체측정 인증의 구현 |
US11170085B2 (en) | 2018-06-03 | 2021-11-09 | Apple Inc. | Implementation of biometric authentication |
US11100349B2 (en) | 2018-09-28 | 2021-08-24 | Apple Inc. | Audio assisted enrollment |
US10860096B2 (en) | 2018-09-28 | 2020-12-08 | Apple Inc. | Device control using gaze information |
CN112154728B (zh) * | 2020-08-20 | 2022-04-22 | 扬州大学 | 一种富含大豆异黄酮的大豆粉末及其制作方法与应用 |
EP4264460A1 (en) | 2021-01-25 | 2023-10-25 | Apple Inc. | Implementation of biometric authentication |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0714927B2 (ja) * | 1988-04-06 | 1995-02-22 | キッコーマン株式会社 | イソフラボン化合物の製造法 |
US5351384A (en) * | 1993-08-06 | 1994-10-04 | Chrysler Corporation | Method of installing instrument panel assemblies in automotive vehicle bodies |
JP3777390B2 (ja) * | 1993-10-12 | 2006-05-24 | アーチャー ダニエルズ ミッドランド カンパニー | アグルコンイソフラボン濃縮植物タンパク質抽出物及び単離物並びにその製造方法 |
CA2173999C (en) * | 1993-10-12 | 2008-09-09 | Jerome L. Shen | An aglucone isoflavone enriched vegetable protein whey, whey protein, and process for producing |
US5320949A (en) * | 1993-10-12 | 1994-06-14 | Protein Technologies International, Inc. | Process for producing aglucone isoflavone enriched vegetable protein fiber |
DE69429673T3 (de) * | 1993-10-12 | 2007-08-23 | Archer Daniels Midland Co., Decatur | Ein aglukon isoflavon angereichertes pflanzenproteinkonzentrat und ein verfahren zu dessen herstellung |
US5885632A (en) * | 1993-12-14 | 1999-03-23 | Nichimo Co., Ltd. | Process for preparing a product from a pulse crop as a starting material and a food containing the product prepared from a pulse crop as a starting material |
US5554519A (en) * | 1995-08-07 | 1996-09-10 | Fermalogic, Inc. | Process of preparing genistein |
-
1996
- 1996-09-06 US US08/709,026 patent/US5726034A/en not_active Expired - Fee Related
-
1997
- 1997-08-25 TW TW86112184A patent/TW574225B/zh not_active IP Right Cessation
- 1997-09-01 AU AU36755/97A patent/AU718810B2/en not_active Ceased
- 1997-09-02 BR BR9704589A patent/BR9704589A/pt active Search and Examination
- 1997-09-03 CA CA002214665A patent/CA2214665C/en not_active Expired - Fee Related
- 1997-09-05 EP EP97306893A patent/EP0827698B2/en not_active Expired - Lifetime
- 1997-09-05 PT PT97306893T patent/PT827698E/pt unknown
- 1997-09-05 CN CNB971205868A patent/CN1210407C/zh not_active Expired - Fee Related
- 1997-09-05 DE DE69701842T patent/DE69701842T3/de not_active Expired - Fee Related
- 1997-09-05 DK DK97306893T patent/DK0827698T4/da active
- 1997-09-05 RU RU97115235/13A patent/RU2152434C1/ru not_active IP Right Cessation
- 1997-09-05 AT AT97306893T patent/ATE192284T1/de active
- 1997-09-05 ES ES97306893T patent/ES2147660T5/es not_active Expired - Lifetime
- 1997-09-05 KR KR1019970045912A patent/KR100412116B1/ko not_active IP Right Cessation
- 1997-09-08 JP JP9243184A patent/JPH1099089A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
KR19980024361A (ko) | 1998-07-06 |
MX9706806A (es) | 1998-03-31 |
BR9704589A (pt) | 1998-09-15 |
PT827698E (pt) | 2000-10-31 |
CN1183475A (zh) | 1998-06-03 |
US5726034A (en) | 1998-03-10 |
JPH1099089A (ja) | 1998-04-21 |
DK0827698T4 (da) | 2008-08-18 |
KR100412116B1 (ko) | 2004-04-08 |
CA2214665A1 (en) | 1998-03-06 |
CA2214665C (en) | 2005-04-12 |
DE69701842D1 (de) | 2000-06-08 |
ES2147660T3 (es) | 2000-09-16 |
EP0827698B2 (en) | 2008-04-09 |
EP0827698B1 (en) | 2000-05-03 |
AU718810B2 (en) | 2000-04-20 |
DK0827698T3 (da) | 2000-08-28 |
TW574225B (en) | 2004-02-01 |
DE69701842T2 (de) | 2000-11-09 |
RU2152434C1 (ru) | 2000-07-10 |
EP0827698A3 (en) | 1998-04-08 |
AU3675597A (en) | 1998-03-12 |
ATE192284T1 (de) | 2000-05-15 |
EP0827698A2 (en) | 1998-03-11 |
ES2147660T5 (es) | 2008-10-16 |
DE69701842T3 (de) | 2008-10-23 |
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