WO2010023162A1 - Process for extraction of glucosinolate s from broccoli seeds - Google Patents
Process for extraction of glucosinolate s from broccoli seeds Download PDFInfo
- Publication number
- WO2010023162A1 WO2010023162A1 PCT/EP2009/060824 EP2009060824W WO2010023162A1 WO 2010023162 A1 WO2010023162 A1 WO 2010023162A1 EP 2009060824 W EP2009060824 W EP 2009060824W WO 2010023162 A1 WO2010023162 A1 WO 2010023162A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- glucosinolate
- process according
- extract
- seeds
- plant parts
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/31—Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/728—Hyaluronic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/04—Processes using organic exchangers
- B01J39/05—Processes using organic exchangers in the strongly acidic form
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/04—Processes using organic exchangers
- B01J41/07—Processes using organic exchangers in the weakly basic form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
Definitions
- This invention relates to a process for extracting glucosinolates from broccoli seeds, sprouts, or florets which comprises a step of adsorbing a broccoli seed extract on a basic resin, followed by elution of the adsorbed glucosinolates and collecting the glucosinolate-rich eluate.
- Broccoli seeds have a high amount of glucosinolates, including glucoraphanin, glucoiberin, glucoerucin. While the glucosinolates are not biologically active, cleavage by the enzyme myrosinase (present in many plant cells and in the gut microflora) results in the formation of active isothiocyanates. These isothiocyanates, including sulforaphane, have been shown to have numerous health-promoting properties, and in some experiments have even been shown to exert various anti-cancer effects.
- a new process for the production of a glucosinolate-containing extract comprises the steps of a) extracting glucosinolate-containing plant parts or seeds, or an extract of glucosinolate- containing plant parts or seeds with an extraction medium that comprises a lower alcohol or ketone or an aqueous mixture of a lower alcohol or ketone to obtain a alcoholic or ketonic extract; b) optionally completely or partially evaporating the extraction medium of step a); c) optionally contacting the extract of step a) or step b) with a cation exchange resin; d) adsorbing the extract from step a), step b), or step c) onto a basic resin; and e) optionally eluting the resulting glucosinolate-containing extract.
- Suitable solvents for step b) through e) include water, C 1-4 alcohols, C3-4 ketones, and mixtures thereof.
- the cation exchange resin is preferably in its acidic form, and more preferably a strong acidic ion exchanger is used.
- an additional step may be performed on the glucosinolate-containing extract obtained from step e).
- the volatiles of the glucosinolate- containing extract are evaporated.
- the result of this step is a solid extract containing glucosinolates, which includes glucoraphanin, glucerucin, and glucoiberin.
- the solid extract made by this process also forms another aspect of this invention.
- the starting materials for this invention may be any glucosinolate-containing plant material, or any glucosinolate-containing extract.
- the plant material is from the Brassicaceae family, such as broccoli, mustard, rapeseed, cauliflower, kohlrabi, cabbage, bok choy, turnip, radish, wasabi, horse radish and brussel sprouts.
- the plant parts may be the sprouts or seeds, as it is known that sprouts and seeds often contain higher amounts of glucosinolates than mature plant leaves, but florets or heads may also be used. If desired, the plant parts may be first subjected to a pre-treatment step of washing, or de-fatting (for seeds).
- the plant is a broccoli plant, and seeds are extracted.
- the original starting material for the process may be either a broccoli seed extract or the broccoli seeds themselves.
- plant parts optionally washed and/or defatted and/or otherwise treated, then they are subjected to an extraction step.
- an aqueous medium or a lower alcohol or ketone wherein a lower alcohol or ketone is a Cl to C4 alcohol or ketone or mixtures thereof.
- This may be performed in the presence of charcoal or other similar material such as celite. See, for example Toribio et al., supra.
- the extract obtained can then be used in the next step. If desired, the extract can be subjected to further purification steps such as ultrafiltration. Also the extract may be optionally concentrated by a complete or partial evaporation of the solvent.
- the extract of plant parts (either as obtained above, or, optionally, a commercially available extract) is then extracted with an extraction medium which comprises a lower alcohol or lower ketone.
- a lower alcohol or lower ketone means that the alcohol is a C1-C4 alcohol or the ketone is a C3-C4 ketone, or mixtures thereof; and is preferably an alcohol or ketone which is approved for use in food manufacturing, such as ethanol or acetone, although using technical ethanol may also be used.
- the alcohol or ketone are preferably ethanol or acetone, and may be in an aqueous solution such as at least about 40% alcohol or ketone; in a preferred embodiment, the lower alcohol or lower ketone is at least about 70% in an aqueous solution, and in a more preferred embodiment it is from about 70% to about 95%. In this step, temperature is not particularly critical.
- the extract may be filtered or decanted to separate the solubles from the insolubles.
- the extract may be evaporated to remove the volatiles, followed by dissolving in an appropriate solvent such as water, lower alcohols, ketones, or a mixture thereof for the next step.
- an appropriate solvent such as water, lower alcohols, ketones, or a mixture thereof for the next step.
- the alcoholic or ketonic extract in the appropriate solvent or solvent mixture is subjected to a cationic ion-exchange column, preferably a strong acidic resin, in its acidic form such as DOWEX® 5OW or AMBERLYST® 15 (both available from Sigma Aldrich). It is also preferred, in keeping with the intended use of the final product as a nutraceutical or - A -
- the resin is chosen as to meet regulatory requirements for food production.
- the basic resin may be either a strongly or weakly basic resin, preferably a weakly basic resin. Examples of suitable resins include
- AMBERLITE® IRA-67, and LEWATIT® VPOC 1065 both available from Sigma Aldrich.
- the resin be suitable from a regulatory view for this purpose.
- temperature is not particularly critical; ambient temperature is preferred.
- the ion-exchange column so-prepared is then eluted with a base such as ammonia, diluted potassium hydroxide, sodium hydroxide, sodium carbonate, sodium hydrogen carbonate or the like, in water, lower alcohol (C1-C4) or acetone or in mixtures thereof.
- a base such as ammonia, diluted potassium hydroxide, sodium hydroxide, sodium carbonate, sodium hydrogen carbonate or the like, in water, lower alcohol (C1-C4) or acetone or in mixtures thereof.
- the preferred base is ammonia in water, lower alcohol (C1-C4) or mixtures of the solvents.
- the resulting eluate contains glucosinolates in a more purified form than the original starting material. While actual amounts of major products may vary from lot-to-lot, depending on the content of the starting plant material; a typical final extract will contain the following major glucosinolates: glucoraphanin, glucoerucin, and glucoiberin. This product forms yet another embodiment of this invention.
- the final extract may be evaporated, freeze-dried or spray-dried using conventional means so that it is a solid extract.
- These processed solid extracts also form an aspect of this invention.
- the extract after ion exchange treatment and elution with ammonia contains the ammonium salt of glucoraphanin as a major product.
- the ammonium salt is changed into an ammonium-free extract suitable for further processing.
- the extract which is acidic is made more basic. This can be done by adding any conventional source of base, such as alkali- or earth alkali hydroxides, such as magnesium hydroxide, calcium hydroxide, sodium hydroxide, potassium hydroxide.
- the base is suitable for use in food, such as sodium hydroxide.
- Enough base is added so that the pH rises to above 7.0, more preferably to about pH 7 to pH 12, and even more preferably to pH 9 to 11.
- a base such as sodium hydroxide
- a basic environment such as from pH 9 to 11
- ammonium ions to sodium ions.
- the volatiles can then be separated from the resulting sodium glucosinolate by conventional means, such as by use of reduced pressure (i.e. removed using a partial vacuum), resulting an-ammonium free extract.
- Example 3 4.Og of the residue of Example 1 was suspended in 40 ml of an ethanohwater (82%: 18%) mixture and heated to reflux for approximately 30 min. The resulting suspension was filtered and the mother liquid was evaporated under reduced pressure (30 mbar) at 60 0 C. An extract was obtained (2.2 g) with a purity of glucoraphanin of 16%.
- Example 3
- Example 7 Washing the loaded basic ion exchanger from Example 5 with 5% aqueous ammonium hydroxide solution in water yielded after evaporation, 385.3 mg glucoraphanin (purity 25%).
- Example 7 Washing the loaded basic ion exchanger from Example 5 with 5% aqueous ammonium hydroxide solution in water yielded after evaporation, 385.3 mg glucoraphanin (purity 25%).
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Mycology (AREA)
- Alternative & Traditional Medicine (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Analytical Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009801339941A CN102137678B (en) | 2008-08-27 | 2009-08-21 | Process for extraction of glucosinolates from broccoli seeds |
JP2011524334A JP5789902B2 (en) | 2008-08-27 | 2009-08-21 | Method for extracting glucosinolate from broccoli seeds |
US13/058,458 US8303998B2 (en) | 2008-08-27 | 2009-08-21 | Process for extraction of glucosinolates from broccoli seeds |
EP09782076.5A EP2315596B1 (en) | 2008-08-27 | 2009-08-21 | Process for extraction of glucosinolates from plants |
US13/645,160 US8491944B2 (en) | 2008-08-27 | 2012-10-04 | Process for extraction of glucosinolates from broccoli seeds |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08163089 | 2008-08-27 | ||
EP08163089.9 | 2008-08-27 | ||
EP08171823.1 | 2008-12-16 | ||
EP08171823 | 2008-12-16 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/058,458 A-371-Of-International US8303998B2 (en) | 2008-08-27 | 2009-08-21 | Process for extraction of glucosinolates from broccoli seeds |
US13/645,160 Continuation US8491944B2 (en) | 2008-08-27 | 2012-10-04 | Process for extraction of glucosinolates from broccoli seeds |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010023162A1 true WO2010023162A1 (en) | 2010-03-04 |
Family
ID=41077100
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/060824 WO2010023162A1 (en) | 2008-08-27 | 2009-08-21 | Process for extraction of glucosinolate s from broccoli seeds |
Country Status (6)
Country | Link |
---|---|
US (2) | US8303998B2 (en) |
EP (1) | EP2315596B1 (en) |
JP (1) | JP5789902B2 (en) |
KR (1) | KR101638205B1 (en) |
CN (1) | CN102137678B (en) |
WO (1) | WO2010023162A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102295667A (en) * | 2011-06-28 | 2011-12-28 | 浙江省农业科学院 | Method for extracting glucoraphanin compound from broccoli and cauliflower |
KR20120054946A (en) * | 2010-11-22 | 2012-05-31 | 건국대학교 산학협력단 | Glucosinolate compound from broccoli and composition having antioxidant and antimicrobial activity comprising the same |
FR2977161A1 (en) * | 2011-07-01 | 2013-01-04 | Sojasun Technologies | COMPOSITIONS FOR THE TREATMENT OR PREVENTION OF PROSTATE CANCER BASED ON BROCOLI SEED EXTRACT. |
WO2015013808A1 (en) | 2013-08-02 | 2015-02-05 | Mpt Mustard Products & Technologies Inc. | Biopesticide compositions comprising water soluble polyols |
CN104803900A (en) * | 2015-04-29 | 2015-07-29 | 重庆大学 | Method for continuously preparing raphanin |
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CN102911216A (en) * | 2011-08-02 | 2013-02-06 | 苏州宝泽堂医药科技有限公司 | Method for separating and preparing cleome gynandra glycoside from capparis spinosa |
CN102898341A (en) * | 2012-10-26 | 2013-01-30 | 贵州大学 | Extracting and purifying method of high-purity sulforaphane |
CN103709211B (en) * | 2013-12-13 | 2016-08-31 | 大兴安岭嘉迪欧营养原料有限公司 | A kind of method preparing glucorphanin from Brassica oleracea L. var. botrytis L. |
CN104131047A (en) * | 2014-01-14 | 2014-11-05 | 南京农业大学 | High-efficiency enrichment technology for isothiocyanate in brassica bud seedlings |
KR101706649B1 (en) * | 2014-10-29 | 2017-02-14 | 한국식품연구원 | Composition for inhibiting toxicity of bisphenol A comprising glucosinolate |
CN105713053B (en) * | 2016-03-26 | 2018-09-21 | 北京化工大学 | A kind of glucosinolate extraction separation method |
CN108690103B (en) * | 2018-04-03 | 2022-02-25 | 山东中医药大学 | Method for preparing high-purity glucoraphanin extract by taking radish seeds as raw materials |
CN116474079A (en) * | 2019-05-08 | 2023-07-25 | 深圳福山生物科技有限公司 | Composition containing glucoraphanin and application thereof |
Citations (1)
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WO2004089065A1 (en) * | 2003-04-14 | 2004-10-21 | Bejo Zaden B.V. | Brassica plants with high levels of anticarcinogenic glucosinolates |
Family Cites Families (2)
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JP2006206509A (en) * | 2005-01-28 | 2006-08-10 | Towa Corporation 株式会社 | Method for producing maca extract |
US7371419B1 (en) * | 2006-12-29 | 2008-05-13 | Kraft Foods Holdings, Inc. | Method of enriching glucoraphanin in radish seed preparations |
-
2009
- 2009-08-21 KR KR1020117004307A patent/KR101638205B1/en active IP Right Grant
- 2009-08-21 CN CN2009801339941A patent/CN102137678B/en not_active Expired - Fee Related
- 2009-08-21 EP EP09782076.5A patent/EP2315596B1/en not_active Not-in-force
- 2009-08-21 JP JP2011524334A patent/JP5789902B2/en not_active Expired - Fee Related
- 2009-08-21 US US13/058,458 patent/US8303998B2/en active Active
- 2009-08-21 WO PCT/EP2009/060824 patent/WO2010023162A1/en active Application Filing
-
2012
- 2012-10-04 US US13/645,160 patent/US8491944B2/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2004089065A1 (en) * | 2003-04-14 | 2004-10-21 | Bejo Zaden B.V. | Brassica plants with high levels of anticarcinogenic glucosinolates |
Non-Patent Citations (10)
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CHEN S ET AL: "In vivo synthesis and purification of radioactive p- hydroxybenzylglucosinolate in Sinapis alba L.", PHYTOCHEMICAL ANALYSIS 200005 GB, vol. 11, no. 3, May 2000 (2000-05-01), pages 174 - 178, XP002552043, ISSN: 0958-0344 * |
ELFAKIR C ET AL: "Comparison of a styrene-divinylbenzene copolymeric anion exchanger and a polymethacrylate copolymeric anion exchanger for glucosinolate separation", JOURNAL OF LIQUID CHROMATOGRAPHY AND RELATED TECHNOLOGIES 1997 US, vol. 20, no. 6, 1997, pages 907 - 921, XP008114041, ISSN: 1082-6076 * |
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PRESTERA T ET AL: "Comprehensive chromatographic and spectroscopic methods for the separation and identification of intact glucosinolates", ANALYTICAL BIOCHEMISTRY 19960801 US, vol. 239, no. 2, 1 August 1996 (1996-08-01), pages 168 - 179, XP002552044, ISSN: 0003-2697 * |
ROCHFORT S ET AL: "The isolation and purification of glucoraphanin from broccoli seeds by solid phase extraction and preparative high performance liquid chromatography", JOURNAL OF CHROMATOGRAPHY, ELSEVIER SCIENCE PUBLISHERS B.V. AMSTERDAM, NL, vol. 1120, no. 1-2, 7 July 2006 (2006-07-07), pages 205 - 210, XP024967225, ISSN: 0021-9673, [retrieved on 20060707] * |
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TRENERRY V C ET AL: "The determination of glucoraphanin in broccoli seeds and florets by solid phase extraction and micellar electrokinetic capillary chromatography", FOOD CHEMISTRY, ELSEVIER SCIENCE PUBLISHERS LTD, GB, vol. 98, no. 1, 1 January 2006 (2006-01-01), pages 179 - 187, XP025129879, ISSN: 0308-8146, [retrieved on 20060101] * |
TROYER J K ET AL: "Analysis of glucosinolates from broccoli and other cruciferous vegetables by hydrophilic interaction liquid chromatography", JOURNAL OF CHROMATOGRAPHY, ELSEVIER SCIENCE PUBLISHERS B.V. AMSTERDAM, NL, vol. 919, no. 2, 15 June 2001 (2001-06-15), pages 299 - 304, XP004248013, ISSN: 0021-9673 * |
WEST L ET AL: "Single column approach for the liquid chromatographic separation of polar and non-polar glucosinolates from broccoli sprouts and seeds", JOURNAL OF CHROMATOGRAPHY, ELSEVIER SCIENCE PUBLISHERS B.V. AMSTERDAM, NL, vol. 966, no. 1-2, 9 August 2002 (2002-08-09), pages 227 - 232, XP004372036, ISSN: 0021-9673 * |
Cited By (12)
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KR20120054946A (en) * | 2010-11-22 | 2012-05-31 | 건국대학교 산학협력단 | Glucosinolate compound from broccoli and composition having antioxidant and antimicrobial activity comprising the same |
KR101630782B1 (en) | 2010-11-22 | 2016-06-15 | 건국대학교 산학협력단 | Glucosinolate Compound from Broccoli and Composition Having Antioxidant and Antimicrobial Activity Comprising the Same |
CN102295667A (en) * | 2011-06-28 | 2011-12-28 | 浙江省农业科学院 | Method for extracting glucoraphanin compound from broccoli and cauliflower |
CN102295667B (en) * | 2011-06-28 | 2014-07-30 | 浙江省农业科学院 | Method for extracting glucoraphanin compound from broccoli and cauliflower |
FR2977161A1 (en) * | 2011-07-01 | 2013-01-04 | Sojasun Technologies | COMPOSITIONS FOR THE TREATMENT OR PREVENTION OF PROSTATE CANCER BASED ON BROCOLI SEED EXTRACT. |
WO2013004436A1 (en) * | 2011-07-01 | 2013-01-10 | Sojasun Technologies | Compositions containing broccoli seeds for treating or preventing prostate cancer |
US9433654B2 (en) | 2011-07-01 | 2016-09-06 | Sojasun Technologies | Compositions containing broccoli seeds for treatment or preventing prostate cancer |
WO2015013808A1 (en) | 2013-08-02 | 2015-02-05 | Mpt Mustard Products & Technologies Inc. | Biopesticide compositions comprising water soluble polyols |
US9258999B2 (en) | 2013-08-02 | 2016-02-16 | Mpt Mustard Products & Technologies, Inc. | Biopesticide compositions comprising water soluble polyols |
US9833000B2 (en) | 2013-08-02 | 2017-12-05 | Mpt Mustard Products & Technologies, Inc. | Biopesticide compositions comprising water soluble polyols |
US10398145B2 (en) | 2013-08-02 | 2019-09-03 | Mpt Mustard Products & Technologies Inc. | Kits comprising biopesticide compositions comprising myrosinase, glucosinolates and water soluble polyols |
CN104803900A (en) * | 2015-04-29 | 2015-07-29 | 重庆大学 | Method for continuously preparing raphanin |
Also Published As
Publication number | Publication date |
---|---|
CN102137678B (en) | 2013-07-03 |
US8303998B2 (en) | 2012-11-06 |
JP2012500822A (en) | 2012-01-12 |
US20130030162A1 (en) | 2013-01-31 |
KR20110068986A (en) | 2011-06-22 |
EP2315596A1 (en) | 2011-05-04 |
CN102137678A (en) | 2011-07-27 |
JP5789902B2 (en) | 2015-10-07 |
KR101638205B1 (en) | 2016-07-08 |
US8491944B2 (en) | 2013-07-23 |
EP2315596B1 (en) | 2018-12-19 |
US20110135766A1 (en) | 2011-06-09 |
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