US20100124598A1 - Chemoprotectants From Crucifer Seeds And Sprouts - Google Patents
Chemoprotectants From Crucifer Seeds And Sprouts Download PDFInfo
- Publication number
- US20100124598A1 US20100124598A1 US12/687,490 US68749010A US2010124598A1 US 20100124598 A1 US20100124598 A1 US 20100124598A1 US 68749010 A US68749010 A US 68749010A US 2010124598 A1 US2010124598 A1 US 2010124598A1
- Authority
- US
- United States
- Prior art keywords
- extract
- sprouts
- chemoprotectant precursor
- kale
- chemoprotectant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Images
Classifications
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
Definitions
- the present invention relates to chemoprotective compounds and method for producing chemoprotective compounds which may be incorporated into a variety of food products. More specifically, an extraction method is provided that is effective for providing an extract having a high ratio of chemoprotective compounds to less desirable compounds while providing a high yield of chemoprotective compounds. Enhanced yields and ratios of chemoprotective compounds are provided by an aqueous extraction method used in combination with adsorbents.
- Cimmalian vegetables contain phytochemical precursors to potent chemoprotectants especially glucoraphanin and its associated conversion product sulforaphane, that when delivered to mammalian cells trigger carcinogen detoxification mechanisms.
- glucoraphanin through its bioactive conversion product sulforphane has recently been shown effective in destroying the organism responsible for causing the majority of stomach ulcers and may provide novel approaches for reducing the risk of developing cardiovascular and ocular diseases.
- Efforts are being undertaken to gain approval for making label claims on food products either naturally high in these agents or for foods containing added crucifer chemoprotectants. Products containing chemoprotectant additives, although without claims, are already on the market.
- Cruciferous vegetables also contain other compounds, such as indole glucosinolates, which are problematic for maintaining good health. Not only are these compounds weak inducers of the carcinogen detoxification system, but also they can induce systems which may bioactivate certain pro-carcinogens.
- the breakdown products of indole glucosinolates formed in the stomach during digestion may act in a similar manner to dioxin, a very potent toxin. Therefore, it is advantageous to produce glucoraphanin-containing preparations containing as little residual indole glucosinolates, or other adverse compounds, as possible.
- the present invention is directed to chemoprotectant precursor compositions provided from crucifer seeds and sprouts and methods for their preparation.
- Treatment of aqueous extracts from crucifer seeds or sprouts with adsorbents substantially increases the ratio of certain highly chemoprotectant precursor compounds (alkyl glucosinolates such as glucoraphanin, a.k.a. sulforaphane glucosinolate) to undesirable compounds such as indole glucosinolates (for example 4-hydroxyglucobrassicin).
- alkyl glucosinolates such as glucoraphanin, a.k.a. sulforaphane glucosinolate
- undesirable compounds such as indole glucosinolates (for example 4-hydroxyglucobrassicin).
- the method provides an extract which has a ratio of glucoraphanin to 4-hydroxyglucobrassicin of about 70 or greater.
- a method for extracting chemoprotectants precursors from crucifer seeds or sprouts includes forming an aqueous extract of crucifer seeds or sprouts.
- the aqueous extract is contacted with an adsorbent.
- the aqueous extract is separated from the adsorbent to provide a chemoprotectant enhanced extract.
- the method is effective for providing a chemoprotectant enhanced extract having a ratio of a number of alkyl glucosinolates, especially glucoraphanin to indole glucosinolates, specifically 4-hydroxyglucobrassicin of about 30 to about 1000 or greater, preferably about 100 to about 1000.
- Crucifer vegetables have been identified as a good source of chemoprotectant precursor phytochemicals.
- Crucifer seeds and sprouts have been found to be an especially good source of chemoprotectant precursors.
- Crucifer seeds or sprouts which are especially useful include broccoli, kale, collard, curly kale, marrowstem kale, thousand head kale, Chinese kale, cauliflower, Portuguese kale, Brussels sprouts, kohlrabi, Jersey kale, savoy cabbage, collards, borecole, radish, and the like as well as mixtures thereof.
- crucifier seeds or seeds and sprouts of broccoli are utilized.
- crucifer seeds When crucifer seeds are used as a starting material, they may be used directly or may be processed prior to aqueous extraction.
- crucifer seeds may be defatted prior to forming an aqueous extract using known defatting procedures. For example, West, L. et al., J Agric. Food Chem. 2004, 52, 916-926, which is incorporated herein by reference.
- crucifer seeds may be ground, pulverized or blended prior to addition of aqueous extract or simultaneously with the addition of an aqueous extract.
- Extraction of seed or sprouts may be conducted with water or water containing an organic solvent, such as ethyl alcohol.
- an aqueous extract of crucifer seeds or sprouts is formed by contacting crucifer seeds or sprouts with water having a temperature of 60 to 110° C. for at least 5 minutes.
- the aqueous extract of seeds or sprouts is contacted with an adsorbent.
- the aqueous extract may be separated from cellular materials and be free of seed and sprout cellular materials.
- the aqueous extract with cellular materials may be contacted directly with adsorbents.
- Adsorbents which may be utilized include activated carbon, silica, chemically-modified silica, bleaching clay and the like as well as and mixtures thereof.
- the adsorbent is activated carbon.
- about 1 to about 20 weight percent adsorbent is mixed with the aqueous extract.
- about 8 to about 12 weight percent adsorbent is mixed with the aqueous extract.
- the aqueous extract of seeds or sprouts is added to a column containing adsorbent materials.
- column processing is effective for providing an extract having a ratio of alkyl glucosinolates, especially glucoraphanin to indole glucosinolates, specifically 4-hydroxyglucobrassicin, of about 30 to about 1000 or greater, preferably about 100 to about 1000.
- food products include the chemoprotectant or chemoprotectant precursor enhanced extract.
- the extract may be incorporated directly into food products or dried, cooled, frozen or freeze-dried and then incorporated into the food products.
- Food product into which the extract may be incorporated include food supplements, drinks, shakes, baked goods, teas, soups, cereals, pills, tablets, salads, sandwiches, granolas, salad dressings, sauces, coffee, cheeses, yogurts, energy bars and the like as well as mixtures thereof.
- the food product may contain an amount of extract effective for providing the food product with 0.003 weight percent to 0.05 weight percent glucoraphanin.
- FIG. 1 provides a general description of methods for extracting chemoprotectant compounds from crucifer seeds or sprouts.
- crucifer seeds and/or sprouts may be processed in a number of different ways.
- An aqueous extract of the seeds or sprouts may be formed and then mixed with adsorbents or applied to an adsorbent-containing column.
- the seeds or sprouts may be mixed directly with an aqueous extract and adsorbents. Seeds or sprouts may extracted with blending, homogenizing or pulverizing using known methods.
- chemoprotectants and “chemoprotective compounds” refers to agents of plant origin that are effective for reducing the susceptibility of mammals to the toxic and neoplastic effects of carcinogens.
- Chemoprotectant “precursors” refer to agents which give rise to chemoprotectants by enzymatic and/or chemical means. Talalay, P. et al, J. Nutr 2001, 131 (11 Suppl), 30275-30335. Examples of such chemoprotectant precursors include alkyl glucosinolates, such as glucoraphanin.
- aqueous extract means extracts prepared with 100% water or up to 25% addition of an organic solvent, such as ethyl alcohol.
- chemoprotectant precursor enhanced extract may be ultrafiltered through >500 MWCO (molecular weight cut-off) filters.
- Crucifer seed and sprouts are useful starting materials.
- the ratio of glucoraphanin to indole glucosinolates is naturally higher in seeds (average of ⁇ 4, with a range of 0.4 to 11) than vegetative tissue. Seeds and sprouts are preferred as a starting material since they have higher amounts of glucoraphanin as compared to mature plants. Seed and sprouts are easier to process and less expensive than mature plants.
- Sprouts suitable as sources of cancer chemoprotectants are generally cruciferous sprouts (family Brassicaceae).
- the sprouts are Brassica oleracea ssp. selected from the group of varieties consisting of acephala (kale, collard, wild cabbage, curly kale), medullosa (marrowstem kale) ramose (thousand head kale), alboglabra (Chinese kale), botrytis (cauliflower, sprouting broccoli), costata (Portuguese kale), gemmifera (Brussels sprouts), gogylodes (kohlrabi), italica (broccoli), palmifolia (Jersey kale), sabauda (savoy cabbage), sabellica (collards), and selensia (borecole), among others.
- Sprouts may be prepared in commercial sprouters, providing water (misting 6 times/day) and light (10 hours/day) over a 5-day period.
- Particularly useful broccoli cultivars to be used in the claimed method are Saga, DeCicco, Everest, Emerald City, Packman, Corvet, Dandy, Early, Emperor, Mariner, Green Comet, Green Valiant, Arcadia, Calabrese Caravel, Chancellor, Citation, Cruiser, Early Purple Sprouting Red Arrow, Eureka, Excelsior, Galleon, Ginga, Goliath, Green Duke, Greenblet, Italian Sprouting, Late Purple Sprouting, Late Winter Sprouting, White Star, Legend, Leprechaun, Marathon, Mariner, Minaret (Romanesco), Paragon, Patriot, Premium Crop, Rapine (Spring Raab), Rosalind, Salade (Fall Raab), Samurai, Shogun, Sprinter, Sultan, Taiko, Trixie, San Miguel, Arcadia, Gypsy, Everest, Patron, Southern Comet, Green Comet, Destiny, Climax and Pirate.
- many other broccoli cultivars are suitable.
- adsorbents refer to compounds that are effective for preferentially adsorbing indole glucosinolates over alkyl glucosinolates.
- Useful adsorbents include activated carbon, including Norit A and Darco 12-20 mesh granular.
- Additonal adsorbents demonstrating some effectiveness include silica, chemically-modified silica (so called C-18 loaded), and bleaching clay (used routinely in vegetable oil processing).
- Adsorbents found ineffective included alumina (neutral, acidic and basic) and Fuller's earth (montmorillonite).
- Chemoprotectant precursor enhanced extracts of crucifers seeds may be incorporated into a variety of foodstuffs.
- the extract may be dried, cooled, frozen or freeze-dried using known methods.
- extracts may be further processed, for example with membrane-processing or dialysis to remove high molecular weight compounds such as proteins and polysaccharides.
- a 30 ml sample of aqueous extract from 1 g of pulverized defatted broccoli seed (var. Gypsy) was treated with 100 mg of activated carbon (Darco G-60) 12-20 mesh by boiling for 1 min. in 30 ml of water followed by filtration to remove spent adsorbent and provide an aqueous extract.
- the initial ratio of glucoraphanin/4-hydroxglucobrassicin of ⁇ 11 in the initial seed was increased to ⁇ 70 in the treated matter. Loss of glucoraphanin was ⁇ 4% as determined by high performance liquid chromatography (HPLC), West, L. et al., J. Chromatogr. A 2002, 966, 227-232.
- a 30 ml sample of aqueous extract from 1 g of pulverized defatted broccoli seed (var Gypsy) was passed down a column containing 1000 mg of graphitized carbon black.
- the initial ratio of glucoraphanin/4-hydroxyglucobrassicin of ⁇ 11 in the initial seed was increased to >1000.
- Loss of glucoraphanin was ⁇ 13% as determined by HPLC.
- a 100 mg portion of activated carbon (Darco G-60) was admixed with 1 g of pulverized defatted broccoli seed (var. Gypsy) and extracted in boiling water followed by centrifugation to remove particulates.
- the initial ratio of glucoraphanin/4-hydroxyglucobrassicin of ⁇ 11 was increased to ⁇ 30. Loss of glucoraphanin was ⁇ 2% as determined by HPLC.
- a 200 g. portion of pulverized and defatted (hexane extractable lipids) broccoli seed (var. Premium Crop) was added to 2 L of boiling water. After 5 min. at boiling water temperature, the mixture was filtered to remove residual plant material and the aqueous extract was treated with 20 g. of activated carbon (Darco G-60) by boiling for ⁇ 1 min. followed by centrifugation and filtration to remove spent adsorbent. The clarified extract was ultrafiltered using a 3000 MWCO membrane all the while retaining the ultrafiltrate. After drying, the light tan in color powder was analyzed by HPLC and found to contain over 30% glucoraphanin by weight and a glucoraphanin/4-hydroxyglucobrassicin ratio of greater than 1000.
- activated carbon Darco G-60
- a 500 g. sample of ⁇ 5 day old whole fresh broccoli sprouts (sprouted from var. Premium Crop) were added to 2 L of boiling water. After 10 min. at boiling water temperature, the mixture was transferred to a blender operating at high speed to disrupt the plant tissue for the purpose of further releasing glucoraphanin. After filtration to remove the residual plant material, the aqueous extract was treated with 20 g. of activated carbon (Darco G-60) by boiling for ⁇ 1 min. followed by centrifugation and filtration to remove spent adsorbent. The clarified extract was ultrafiltered using a 3000 MWCO membrane all the while retaining the ultrafiltrate. After drying, the white in color powder was analyzed by HPLC and found to contain over 10% glucoraphanin by weight and a glucoraphanin/4-hydroxyglucobrassicin ratio of greater than 1000.
- activated carbon Darco G-60
Abstract
The present invention is directed to chemoprotectant precursor compositions provided from crucifer seeds and sprouts and methods for their preparation. Treatment of aqueous extracts from crucifer seeds or sprouts with adsorbents substantially increases the ratio of certain highly chemoprotectant precursor compounds (alkyl glucosinolates such as glucoraphanin, a.k.a. sulforaphane glucosinolate) to undesirable compounds such as indole glucosinolates (for example 4-hydroxyglucobrassicin). The method provides an extract which has a ratio of glucoraphanin to 4-hydroxyglucobrassicin of about 70 or greater. The resulting extract has improved color and odor and may be dried or used directly as an additive in a variety of foodstuffs.
Description
- The present invention relates to chemoprotective compounds and method for producing chemoprotective compounds which may be incorporated into a variety of food products. More specifically, an extraction method is provided that is effective for providing an extract having a high ratio of chemoprotective compounds to less desirable compounds while providing a high yield of chemoprotective compounds. Enhanced yields and ratios of chemoprotective compounds are provided by an aqueous extraction method used in combination with adsorbents.
- It is generally agreed that diet plays a large role in controlling the risk of developing cancers and that increased consumption of fruits and vegetables may reduce cancer incidences in humans. The presence of certain minor chemical components in plants may provide a major protection mechanism when delivered to mammalian cells.
- Cruciferious vegetables contain phytochemical precursors to potent chemoprotectants especially glucoraphanin and its associated conversion product sulforaphane, that when delivered to mammalian cells trigger carcinogen detoxification mechanisms. In addition to reducing the risk of getting certain cancers, glucoraphanin through its bioactive conversion product sulforphane has recently been shown effective in destroying the organism responsible for causing the majority of stomach ulcers and may provide novel approaches for reducing the risk of developing cardiovascular and ocular diseases. Efforts are being undertaken to gain approval for making label claims on food products either naturally high in these agents or for foods containing added crucifer chemoprotectants. Products containing chemoprotectant additives, although without claims, are already on the market.
- Cruciferous vegetables also contain other compounds, such as indole glucosinolates, which are problematic for maintaining good health. Not only are these compounds weak inducers of the carcinogen detoxification system, but also they can induce systems which may bioactivate certain pro-carcinogens. In addition, the breakdown products of indole glucosinolates formed in the stomach during digestion may act in a similar manner to dioxin, a very potent toxin. Therefore, it is advantageous to produce glucoraphanin-containing preparations containing as little residual indole glucosinolates, or other adverse compounds, as possible.
- Several patents describe the development of highly chemoprotecant crucifer germplasm with a significantly improved ratio of glucoraphanin to indole glucosinolates (increasing the ratio from about 0.2 to ˜30). See, e.g., U.S. Pat. Nos. 6,521,818, 6,242,018, 6,177,122, 5,968,567, 5,968,505 and 5,725,895; however, developing the germplasm from laboratory to field trials to market will require considerable time, upwards of up to 5 years, and with no guarantee of success. Hence, there is a need to provide alternative methods for producing high yields of glucoraphanin with a high ratio of glucoraphanin to indole glucosinolates.
- The present invention is directed to chemoprotectant precursor compositions provided from crucifer seeds and sprouts and methods for their preparation. Treatment of aqueous extracts from crucifer seeds or sprouts with adsorbents substantially increases the ratio of certain highly chemoprotectant precursor compounds (alkyl glucosinolates such as glucoraphanin, a.k.a. sulforaphane glucosinolate) to undesirable compounds such as indole glucosinolates (for example 4-hydroxyglucobrassicin). The method provides an extract which has a ratio of glucoraphanin to 4-hydroxyglucobrassicin of about 70 or greater. The resulting extract has improved color and odor and may be dried or used directly as an additive in a variety of foodstuffs.
- A method is provided for extracting chemoprotectants precursors from crucifer seeds or sprouts. Generally, the method includes forming an aqueous extract of crucifer seeds or sprouts. The aqueous extract is contacted with an adsorbent. The aqueous extract is separated from the adsorbent to provide a chemoprotectant enhanced extract. The method is effective for providing a chemoprotectant enhanced extract having a ratio of a number of alkyl glucosinolates, especially glucoraphanin to indole glucosinolates, specifically 4-hydroxyglucobrassicin of about 30 to about 1000 or greater, preferably about 100 to about 1000.
- Crucifer vegetables have been identified as a good source of chemoprotectant precursor phytochemicals. Crucifer seeds and sprouts have been found to be an especially good source of chemoprotectant precursors. Crucifer seeds or sprouts which are especially useful include broccoli, kale, collard, curly kale, marrowstem kale, thousand head kale, Chinese kale, cauliflower, Portuguese kale, Brussels sprouts, kohlrabi, Jersey kale, savoy cabbage, collards, borecole, radish, and the like as well as mixtures thereof. In a very important aspect, crucifier seeds or seeds and sprouts of broccoli are utilized.
- When crucifer seeds are used as a starting material, they may be used directly or may be processed prior to aqueous extraction. In one aspect, crucifer seeds may be defatted prior to forming an aqueous extract using known defatting procedures. For example, West, L. et al., J Agric. Food Chem. 2004, 52, 916-926, which is incorporated herein by reference. In another aspect, crucifer seeds may be ground, pulverized or blended prior to addition of aqueous extract or simultaneously with the addition of an aqueous extract.
- Extraction of seed or sprouts may be conducted with water or water containing an organic solvent, such as ethyl alcohol. In another alternative aspect, an aqueous extract of crucifer seeds or sprouts is formed by contacting crucifer seeds or sprouts with water having a temperature of 60 to 110° C. for at least 5 minutes.
- The aqueous extract of seeds or sprouts is contacted with an adsorbent. The aqueous extract may be separated from cellular materials and be free of seed and sprout cellular materials. Alternatively, the aqueous extract with cellular materials may be contacted directly with adsorbents. Adsorbents which may be utilized include activated carbon, silica, chemically-modified silica, bleaching clay and the like as well as and mixtures thereof. In a very important aspect, the adsorbent is activated carbon. Generally, about 1 to about 20 weight percent adsorbent is mixed with the aqueous extract. In a very important aspect, about 8 to about 12 weight percent adsorbent is mixed with the aqueous extract.
- In another aspect, the aqueous extract of seeds or sprouts is added to a column containing adsorbent materials. In this aspect, column processing is effective for providing an extract having a ratio of alkyl glucosinolates, especially glucoraphanin to indole glucosinolates, specifically 4-hydroxyglucobrassicin, of about 30 to about 1000 or greater, preferably about 100 to about 1000.
- In another aspect, food products are provided that include the chemoprotectant or chemoprotectant precursor enhanced extract. The extract may be incorporated directly into food products or dried, cooled, frozen or freeze-dried and then incorporated into the food products. Food product into which the extract may be incorporated include food supplements, drinks, shakes, baked goods, teas, soups, cereals, pills, tablets, salads, sandwiches, granolas, salad dressings, sauces, coffee, cheeses, yogurts, energy bars and the like as well as mixtures thereof. In this aspect, the food product may contain an amount of extract effective for providing the food product with 0.003 weight percent to 0.05 weight percent glucoraphanin.
-
FIG. 1 provides a general description of methods for extracting chemoprotectant compounds from crucifer seeds or sprouts. - As shown in
FIG. 1 , crucifer seeds and/or sprouts may be processed in a number of different ways. An aqueous extract of the seeds or sprouts may be formed and then mixed with adsorbents or applied to an adsorbent-containing column. Alternatively, the seeds or sprouts may be mixed directly with an aqueous extract and adsorbents. Seeds or sprouts may extracted with blending, homogenizing or pulverizing using known methods. - As used herein “chemoprotectants” and “chemoprotective compounds” refers to agents of plant origin that are effective for reducing the susceptibility of mammals to the toxic and neoplastic effects of carcinogens. Chemoprotectant “precursors” refer to agents which give rise to chemoprotectants by enzymatic and/or chemical means. Talalay, P. et al, J. Nutr 2001, 131 (11 Suppl), 30275-30335. Examples of such chemoprotectant precursors include alkyl glucosinolates, such as glucoraphanin.
- As used herein “aqueous extract” means extracts prepared with 100% water or up to 25% addition of an organic solvent, such as ethyl alcohol.
- Other methods which may be used to selectively concentrate chemoprotectants and chemoprotectant precursors include: preparative liquid chromatography, membrane ultrafiltration, selective precipitation, preparative electrophoresis and preparative counter current distribution techniques. Troyer, J. et al., J. Chromatogr. A 2001, 919, 299-304; West, L. et al. J. Chromatogr. A 2002, 966, 227-232; Fahey, J. et al. J. Chromatogr. A 2003, 966, 85-93; and Iori, R., Patent Application B098A 000425 1998. In another alternative, to further purify extracts based on molecular weight, chemoprotectant precursor enhanced extract may be ultrafiltered through >500 MWCO (molecular weight cut-off) filters.
- Crucifer seed and sprouts are useful starting materials. The ratio of glucoraphanin to indole glucosinolates is naturally higher in seeds (average of ˜4, with a range of 0.4 to 11) than vegetative tissue. Seeds and sprouts are preferred as a starting material since they have higher amounts of glucoraphanin as compared to mature plants. Seed and sprouts are easier to process and less expensive than mature plants.
- Sprouts suitable as sources of cancer chemoprotectants are generally cruciferous sprouts (family Brassicaceae). Preferably the sprouts are Brassica oleracea ssp. selected from the group of varieties consisting of acephala (kale, collard, wild cabbage, curly kale), medullosa (marrowstem kale) ramose (thousand head kale), alboglabra (Chinese kale), botrytis (cauliflower, sprouting broccoli), costata (Portuguese kale), gemmifera (Brussels sprouts), gogylodes (kohlrabi), italica (broccoli), palmifolia (Jersey kale), sabauda (savoy cabbage), sabellica (collards), and selensia (borecole), among others. Numerous methods for the cultivation of sprouts are known, as exemplified by U.S. Pat. Nos. 3,733,745, 3,643,376, 3,945,148, 4,130,964, 4,292,769 and 4,086,725 which are all incorporated herein by reference. Sprouts may be prepared in commercial sprouters, providing water (misting 6 times/day) and light (10 hours/day) over a 5-day period.
- Particularly useful broccoli cultivars to be used in the claimed method are Saga, DeCicco, Everest, Emerald City, Packman, Corvet, Dandy, Early, Emperor, Mariner, Green Comet, Green Valiant, Arcadia, Calabrese Caravel, Chancellor, Citation, Cruiser, Early Purple Sprouting Red Arrow, Eureka, Excelsior, Galleon, Ginga, Goliath, Green Duke, Greenblet, Italian Sprouting, Late Purple Sprouting, Late Winter Sprouting, White Star, Legend, Leprechaun, Marathon, Mariner, Minaret (Romanesco), Paragon, Patriot, Premium Crop, Rapine (Spring Raab), Rosalind, Salade (Fall Raab), Samurai, Shogun, Sprinter, Sultan, Taiko, Trixie, San Miguel, Arcadia, Gypsy, Everest, Patron, Southern Comet, Green Comet, Destiny, Climax and Pirate. However, many other broccoli cultivars are suitable.
- Crucifers seed or sprouts or aqueous extracts of crucifer seed or sprouts may be mixed directly with adsorbents in batch mode, semi-continuous mode or continuous mode (e.g. using an adsorbent column). As used herein, adsorbents refer to compounds that are effective for preferentially adsorbing indole glucosinolates over alkyl glucosinolates. Useful adsorbents include activated carbon, including Norit A and Darco 12-20 mesh granular. Additonal adsorbents demonstrating some effectiveness include silica, chemically-modified silica (so called C-18 loaded), and bleaching clay (used routinely in vegetable oil processing). Adsorbents found ineffective included alumina (neutral, acidic and basic) and Fuller's earth (montmorillonite).
- Chemoprotectant precursor enhanced extracts of crucifers seeds may be incorporated into a variety of foodstuffs. The extract may be dried, cooled, frozen or freeze-dried using known methods. Alternatively, extracts may be further processed, for example with membrane-processing or dialysis to remove high molecular weight compounds such as proteins and polysaccharides.
- A 30 ml sample of aqueous extract from 1 g of pulverized defatted broccoli seed (var. Gypsy) was treated with 100 mg of activated carbon (Darco G-60) 12-20 mesh by boiling for 1 min. in 30 ml of water followed by filtration to remove spent adsorbent and provide an aqueous extract. The initial ratio of glucoraphanin/4-hydroxglucobrassicin of ˜11 in the initial seed was increased to ˜70 in the treated matter. Loss of glucoraphanin was ˜4% as determined by high performance liquid chromatography (HPLC), West, L. et al., J. Chromatogr. A 2002, 966, 227-232.
- A 30 ml sample of aqueous extract from 1 g of pulverized defatted broccoli seed (var Gypsy) was passed down a column containing 1000 mg of graphitized carbon black. The initial ratio of glucoraphanin/4-hydroxyglucobrassicin of ˜11 in the initial seed was increased to >1000. Loss of glucoraphanin was ˜13% as determined by HPLC.
- A 100 mg portion of activated carbon (Darco G-60) was admixed with 1 g of pulverized defatted broccoli seed (var. Gypsy) and extracted in boiling water followed by centrifugation to remove particulates. The initial ratio of glucoraphanin/4-hydroxyglucobrassicin of ˜11 was increased to ˜30. Loss of glucoraphanin was ˜2% as determined by HPLC.
- A 200 g. portion of pulverized and defatted (hexane extractable lipids) broccoli seed (var. Premium Crop) was added to 2 L of boiling water. After 5 min. at boiling water temperature, the mixture was filtered to remove residual plant material and the aqueous extract was treated with 20 g. of activated carbon (Darco G-60) by boiling for ˜1 min. followed by centrifugation and filtration to remove spent adsorbent. The clarified extract was ultrafiltered using a 3000 MWCO membrane all the while retaining the ultrafiltrate. After drying, the light tan in color powder was analyzed by HPLC and found to contain over 30% glucoraphanin by weight and a glucoraphanin/4-hydroxyglucobrassicin ratio of greater than 1000.
- A 500 g. sample of ˜5 day old whole fresh broccoli sprouts (sprouted from var. Premium Crop) were added to 2 L of boiling water. After 10 min. at boiling water temperature, the mixture was transferred to a blender operating at high speed to disrupt the plant tissue for the purpose of further releasing glucoraphanin. After filtration to remove the residual plant material, the aqueous extract was treated with 20 g. of activated carbon (Darco G-60) by boiling for ˜1 min. followed by centrifugation and filtration to remove spent adsorbent. The clarified extract was ultrafiltered using a 3000 MWCO membrane all the while retaining the ultrafiltrate. After drying, the white in color powder was analyzed by HPLC and found to contain over 10% glucoraphanin by weight and a glucoraphanin/4-hydroxyglucobrassicin ratio of greater than 1000.
Claims (19)
1-14. (canceled)
15. A chemoprotectant precursor enhanced extract containing crucifer seeds or sprouts formed by a process comprising:
forming an aqueous extract of crucifer seeds or sprouts;
contacting the aqueous extract with an adsorbent; and
separating the adsorbent from the aqueous extract to provide the chemoprotectant precursor enhanced extract,
the method effective for providing a number ratio of alkyl glucosinolates to indole glucosinolates of at least about 30 in the chemoprotectant precursor enhanced extract.
16. The method of claim 15 , wherein the alkyl glucosinolates are glucoraphanin.
17. The method of claim 15 , wherein the indole glucosinolates are 4-hydroxyglucobrassicin.
18. The method of claim 15 , wherein the ratio of a number of alkyl glucosinolates to indole glucosinolates is about 30 to about 1000.
19. The method of claim 15 , wherein the ratio of a number of alkyl glucosinolates to indole glucosinolates is about 1000 or greater.
20. The chemoprotectant precursor enhanced extract of claim 15 , wherein the crucifer seeds or sprouts are selected from the group consisting of broccoli, kale, collard, curly kale, marrowstem kale, thousand head kale, Chinese kale, cauliflower, Portuguese kale, Brussels sprouts, kohlrabi, Jersey kale, savoy cabbage, collards, borecole, radish and mixtures thereof.
21. The chemoprotectant precursor enhanced extract of claim 20 , wherein the crucifer seeds or sprouts are broccoli.
22. The chemoprotectant precursor enhanced extract of claim 20 , wherein the crucifer seeds are defatted prior to forming an aqueous extract.
23. The chemoprotectant precursor enhanced extract of claim 15 , wherein the aqueous extract of crucifer seeds or sprouts is formed by contacting crucifer seeds or sprouts with water having a temperature of about 60° to about 110° C. for at least about 5 minutes.
24. The chemoprotectant precursor enhanced extract of claim 15 , wherein the adsorbent is selected from the group consisting of activated carbon, silica, chemically-modified silica, bleaching clay, and mixtures thereof.
25. The chemoprotectant precursor enhanced extract of claim 24 , wherein the adsorbent is activated carbon.
26. The chemoprotectant precursor enhanced extract of claim 15 , wherein about 1 to about 20 weight percent adsorbent is mixed with the aqueous extract.
27. The chemoprotectant precursor enhanced extract of claim 25 , wherein about 8 to about 12 weight percent adsorbent is mixed with the aqueous extract.
28. The chemoprotectant precursor enhanced extract of claim 15 , wherein the aqueous extract is added to a column containing adsorbent.
29. The chemoprotectant precursor enhanced extract of claim 15 , wherein the aqueous extract is dried, cooled, frozen or freeze-dried.
30. The chemoprotectant precursor enhanced extract of claim 15 , wherein the aqueous extract is ultrafiltered through at least a 500 MWCO membranes.
31. A food product comprising an effective amount of the extract of claim 1.
32. The food product of claim 31 , wherein the food product is selected from the group consisting of food supplements, drinks, shakes, baked goods, teas, soups, cereals, pills, tablets, salads, sandwiches, granolas, salad dressings, sauces, coffee, cheeses, yogurts, energy bars and mixtures thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/687,490 US20100124598A1 (en) | 2005-08-09 | 2010-01-14 | Chemoprotectants From Crucifer Seeds And Sprouts |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/199,752 US7744937B2 (en) | 2005-08-09 | 2005-08-09 | Chemoprotectants from crucifer seeds and sprouts |
US12/687,490 US20100124598A1 (en) | 2005-08-09 | 2010-01-14 | Chemoprotectants From Crucifer Seeds And Sprouts |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/199,752 Division US7744937B2 (en) | 2005-08-09 | 2005-08-09 | Chemoprotectants from crucifer seeds and sprouts |
Publications (1)
Publication Number | Publication Date |
---|---|
US20100124598A1 true US20100124598A1 (en) | 2010-05-20 |
Family
ID=37523538
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/199,752 Expired - Fee Related US7744937B2 (en) | 2005-08-09 | 2005-08-09 | Chemoprotectants from crucifer seeds and sprouts |
US12/687,490 Abandoned US20100124598A1 (en) | 2005-08-09 | 2010-01-14 | Chemoprotectants From Crucifer Seeds And Sprouts |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/199,752 Expired - Fee Related US7744937B2 (en) | 2005-08-09 | 2005-08-09 | Chemoprotectants from crucifer seeds and sprouts |
Country Status (12)
Country | Link |
---|---|
US (2) | US7744937B2 (en) |
EP (1) | EP1752052B1 (en) |
CN (1) | CN1935003A (en) |
AR (1) | AR054902A1 (en) |
AU (1) | AU2006203321B2 (en) |
BR (1) | BRPI0603903A (en) |
CA (1) | CA2554969A1 (en) |
NO (1) | NO20063553L (en) |
NZ (1) | NZ548951A (en) |
PL (1) | PL1752052T3 (en) |
RU (1) | RU2378002C2 (en) |
UA (1) | UA92140C2 (en) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105198782A (en) * | 2015-10-23 | 2015-12-30 | 河南科技学院 | Method for extracting, separating and purifying sulforaphene in radish seeds |
CN105713053A (en) * | 2016-03-26 | 2016-06-29 | 北京化工大学 | Extraction and separation method of glucosinolate |
US9585860B2 (en) | 2011-01-12 | 2017-03-07 | The William M. Yavbrough Foundation | Method for treating eczema |
US9636320B2 (en) | 2012-07-26 | 2017-05-02 | The William M. Yarbrough Foundation | Method for treating skin cancer |
US9771322B2 (en) | 2011-01-03 | 2017-09-26 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US9839621B2 (en) | 2012-07-26 | 2017-12-12 | The William M. Yarbrough Foundation | Method for treating bladder cancer |
US9949943B2 (en) | 2012-07-26 | 2018-04-24 | The William M. Yarbrough Foundation | Method for treating neurodegenerative diseases |
US9962361B2 (en) | 2011-01-03 | 2018-05-08 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US10080734B2 (en) | 2012-07-26 | 2018-09-25 | The William M. Yarbrough Foundation | Method for treating autism and other neurodevelopmental disorders |
US10273205B2 (en) | 2011-01-03 | 2019-04-30 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating isothiocyanate functional surfactants and associated methods for treating biofilms |
US10308599B2 (en) | 2011-01-03 | 2019-06-04 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US10335387B2 (en) | 2012-07-26 | 2019-07-02 | The William M. Yarbrough Foundation | Method for treating infectious diseases with isothiocyanate functional compounds |
US10434081B2 (en) | 2012-07-26 | 2019-10-08 | The William M. Yarbrough Foundation | Inhibitors of macrophage migration inhibitory factor |
US10434082B2 (en) | 2012-07-26 | 2019-10-08 | The William M. Yarbrough Foundation | Isothiocyanate functional compounds augmented with secondary antineoplastic medicaments and associated methods for treating neoplasms |
US10441561B2 (en) | 2012-07-26 | 2019-10-15 | The William M. Yanbrough Foundation | Method for treating benign prostatic hyperplasia (BPH), prostatitis, and prostate cancer |
US10532039B2 (en) | 2011-02-08 | 2020-01-14 | The William M. Yarbrough Foundation | Method for treating psoriasis |
US10640464B2 (en) | 2011-01-03 | 2020-05-05 | The William M. Yarbrough Foundation | Use of isothiocyanate functional surfactants as Nrf2 inducers to treat epidermolysis bullosa simplex and related diseases |
US10647668B2 (en) | 2011-01-03 | 2020-05-12 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US11279674B2 (en) | 2011-01-03 | 2022-03-22 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US11407713B2 (en) | 2011-01-03 | 2022-08-09 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7744937B2 (en) | 2005-08-09 | 2010-06-29 | Kraft Foods Global Brands Llc | Chemoprotectants from crucifer seeds and sprouts |
US7371419B1 (en) * | 2006-12-29 | 2008-05-13 | Kraft Foods Holdings, Inc. | Method of enriching glucoraphanin in radish seed preparations |
US20080311192A1 (en) * | 2007-06-12 | 2008-12-18 | Kraft Foods Holdings, Inc. | Enteric-Coated Glucosinolates And Beta-Thioglucosidases |
US20080311276A1 (en) * | 2007-06-12 | 2008-12-18 | Kraft Foods Holdings, Inc. | Production of Glucosinolates from Agricultural By-Products & Waste |
IT1394763B1 (en) * | 2009-06-19 | 2012-07-13 | Bios Line S P A | METHOD OF PREPARATION OF PURIFIED EXTRACT FROM CABBAGE LACINIATO NERO TOSCANO AND COMPOSITIONS OF THE SAME |
CN102399247B (en) * | 2010-09-19 | 2013-10-02 | 上海中医药大学 | Method for separating potassium myronate compounds from indigowoad root |
WO2012116018A1 (en) | 2011-02-22 | 2012-08-30 | Caudill Seed Company, Inc. | Spray dried myrosinase and use to produce isothiocyanates |
FR2977161B1 (en) * | 2011-07-01 | 2013-07-19 | Sojasun Technologies | COMPOSITIONS FOR THE TREATMENT OR PREVENTION OF PROSTATE CANCER BASED ON BROCOLI SEED EXTRACT. |
CN104803900B (en) * | 2015-04-29 | 2016-08-24 | 重庆大学 | A kind of method preparing sulforaphen continuously |
CN104800270B (en) * | 2015-05-20 | 2018-07-31 | 皖南医学院 | A kind of preparation method of broccoli sprout extract capsule |
CN107710962A (en) * | 2017-11-16 | 2018-02-23 | 蚌埠市徽吉星农业科技农民专业合作社 | A kind of sponge gourd method for treating seeds |
CN108702891A (en) * | 2018-04-11 | 2018-10-26 | 上海大学 | Application of the carbon monoxide in handling vegetable seeds |
TWI693072B (en) * | 2018-12-14 | 2020-05-11 | 大漢酵素生物科技股份有限公司 | Anti-cancer fermented liquid with glucosinolate compound and usage thereof |
CN113180097A (en) * | 2021-04-27 | 2021-07-30 | 成都市三禾田生物技术有限公司 | Production method of lyophilized broccoli sprout powder |
Citations (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4083836A (en) * | 1974-05-17 | 1978-04-11 | Alfa-Laval Ab | Production of rapeseed protein concentrate for human consumption |
US5043178A (en) * | 1988-02-09 | 1991-08-27 | Kraft General Foods, Inc. | Method for the extraction of roasted and ground coffee |
US5077071A (en) * | 1989-09-06 | 1991-12-31 | Epe Incorporated | Oil extrusion process |
US5686108A (en) * | 1995-09-27 | 1997-11-11 | Amway Corporation | Brassica vegetable supplement and process for manufacture |
US5725895A (en) * | 1995-09-15 | 1998-03-10 | Johns Hopkins School Of Medicine | Method of preparing a food product from cruciferous seeds |
US6086936A (en) * | 1995-12-14 | 2000-07-11 | Kal Kan Foods, Inc. | High temperature/ultra-high pressure sterilization of foods |
US6117460A (en) * | 1996-12-16 | 2000-09-12 | Kortschack; Fritz | Method of producing stable meat products and sausages, produced in the presence of microorganisms |
US6242018B1 (en) * | 1997-04-11 | 2001-06-05 | Johns Hopkins School Of Medicine | Cancer Chemoprotective food products |
US20020015722A1 (en) * | 1999-05-05 | 2002-02-07 | Herzog Leslie John | Food product |
US6348220B1 (en) * | 1999-04-09 | 2002-02-19 | Rutgers, The State University Of New Jersey | Phenethylisothiocyanate nutraceutical compositions and methods |
US6361812B1 (en) * | 1999-11-18 | 2002-03-26 | The Procter & Gamble Co. | Products comprising an isothiocyanate preservative system and methods of their use |
US20020090405A1 (en) * | 2000-09-15 | 2002-07-11 | Najla Guthrie | Components of canola for the treatment of cancer |
US6436450B1 (en) * | 2000-12-08 | 2002-08-20 | Access Business Group International Llc | Brassica vegetable composition and method for manufacture of same |
US20020147155A1 (en) * | 2001-04-06 | 2002-10-10 | Foster Warren G. | Prevention and treatment of endometriosis with aryl hydrocarbon receptor binding ligands |
US20020151505A1 (en) * | 2000-08-21 | 2002-10-17 | Fahey Jed W. | Treatment of helicobacter with isothiocyanates |
US6521818B1 (en) * | 1998-07-01 | 2003-02-18 | John Hopkins School Of Medicine | Development of novel highly chemoprotectant crucifer germplasm |
US20030091518A1 (en) * | 1999-12-20 | 2003-05-15 | Gilles Pauly | Cosmetic and/or pharmaceutical preparations |
US20030235634A1 (en) * | 2002-06-21 | 2003-12-25 | Access Business Group International Llc. | Extraction of non-polar isothiocyanates from plants and dietary supplements containing same |
US20040001817A1 (en) * | 2002-05-14 | 2004-01-01 | Giampapa Vincent C. | Anti-aging nutritional supplement |
US20040052879A1 (en) * | 2000-05-30 | 2004-03-18 | Giampietro Ravagnan | Method for the extraction of pharmaceutically active products from spermatophyte plants, products thus obtained and their use in the medical field, in particular as substances with anti-tumoral activity |
US20040133936A1 (en) * | 2000-08-17 | 2004-07-08 | John Rossiter | Enzyme |
US6812248B2 (en) * | 2000-07-05 | 2004-11-02 | John Hopkins University School Of Medicine | Prevention and treatment of degenerative diseases by glutathione and phase II detoxification enzymes |
US20050031768A1 (en) * | 2003-08-07 | 2005-02-10 | Shiro Sakai | Fractionation of allyl isothiocyanate, p-hydroxybenzyl-isothiocyanate, protein and fiber from mustard |
US20050042347A1 (en) * | 2002-01-28 | 2005-02-24 | Bathurst Christopher Francis | Composition |
US20050055744A1 (en) * | 2001-07-05 | 2005-03-10 | Carlos Quiros | Nucleic acids encoding glucosinolate biosynthesis enzymes and methods of their use |
US20050123560A1 (en) * | 2003-12-04 | 2005-06-09 | Sinnott Robert A. | High purity and water dispersible extract and formulations of larrea tridentata leaf resin, and methods of making and using the same |
US20060003073A1 (en) * | 2004-05-07 | 2006-01-05 | Etzel Mark R | Methods and compositions involving whey protein isolates |
US20060020046A1 (en) * | 2002-02-15 | 2006-01-26 | Dms Ip Assets B.V. | Compositions comprising lycopene for the treatment and prevention of angiogenesis associated pathologies |
US20060127996A1 (en) * | 2004-12-14 | 2006-06-15 | Johns Hopkins University | Method of extraction of isothiocyanates into oil from glucosinolate-containing plants and method of producing products with oil containing isothiocyanates extracted from glucosinolate-containing plants |
US20070033675A1 (en) * | 2003-04-14 | 2007-02-08 | Piet Barten | Brassica plants with high levels of anticarcinogenic glucosinolates |
US20070031581A1 (en) * | 2005-08-09 | 2007-02-08 | Kraft Foods Holdings, Inc. | Chemoprotectants from crucifer seeds and sprouts |
US20070190209A1 (en) * | 2006-02-10 | 2007-08-16 | Mannatech, Inc. | All natural multivitamin and multimineral dietary supplement formulations for enhanced absorption and biological utilization |
US20080107792A1 (en) * | 2003-07-31 | 2008-05-08 | Martine Elisa Verhoeyen | Use of Plants with Increased Levels of Flavonol Glycosides in Reducing Hypertension |
US7371419B1 (en) * | 2006-12-29 | 2008-05-13 | Kraft Foods Holdings, Inc. | Method of enriching glucoraphanin in radish seed preparations |
US7407986B2 (en) * | 2001-12-18 | 2008-08-05 | Brassica Foundation For Chemoprotection Research, Inc. | Prevention and treatment of oxidative stress disorders by glutathione and phase II detoxification enzymes |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3945148A (en) | 1975-03-10 | 1976-03-23 | George Clem Oyama | Method and apparatus for growing bean sprouts |
US4130964A (en) | 1975-12-01 | 1978-12-26 | Caballero Edward A | Apparatus and method for growing legume sprouts |
US4086725A (en) | 1976-06-25 | 1978-05-02 | Tsiang Kwang Li | Method and apparatus for growing plant sprouts |
CH622346A5 (en) | 1977-09-29 | 1981-03-31 | Kistler Instrumente Ag | |
EP0006654B1 (en) | 1978-06-26 | 1982-03-31 | Unilever N.V. | A process for producing a detoxified rapeseed protein concentrate |
CA2172244A1 (en) | 1993-09-24 | 1995-03-30 | Johannes Petrus Paulus Maria Smelt | Shelf stable product |
DE69430619D1 (en) | 1994-02-17 | 2002-06-20 | Nestle Sa | Production of low-salt and / or low-phosphate sausages |
DE19649952A1 (en) | 1996-12-03 | 1998-06-04 | Uhde Hochdrucktechnik Gmbh | Process for the preservation of solid, liquid or pasty perishable products |
GB9717104D0 (en) | 1997-08-12 | 1997-10-15 | Innes John Centre Innov Ltd | Food products |
FR2769837B1 (en) | 1997-10-17 | 2000-02-25 | Bio Sphere 99 Lab | COMPOSITION FOR DIETETICS OR COSMETICS BASED ON PLANT EXTRACTS |
US20030161917A1 (en) | 1998-01-20 | 2003-08-28 | Ernest A. Voisin | Process of elimination of bacteria in shellfish of shucking shellfish and an apparatus therefor |
FR2786096B1 (en) | 1998-11-20 | 2002-10-18 | Jean Pascal Conduzorgues | COMPOSITION FOR THE PREVENTION AND TOPICAL TREATMENT OF CELLULITE |
IT1317034B1 (en) | 2000-05-30 | 2003-05-26 | Istituto Di Medicina Speriment | METHOD OF EXTRACTION OF PHARMACEUTICAL ACTIVITY PRODUCTS FROM PLANTS SPERMATOPHYTES, PRODUCTS SO OBTAINED AND THEIR USE IN MEDICINE, IN |
FI116878B (en) | 2003-02-21 | 2006-03-31 | Maa Ja Elintarviketalouden Tut | Control of the enzymatic degradation of glucosinolates by the lactic acid bacterium |
JP2005206495A (en) | 2004-01-21 | 2005-08-04 | Univ Nihon | Health food for preventing cancer and medicinal composition |
WO2006012213A2 (en) | 2004-06-25 | 2006-02-02 | Tea Guard Llc | Composition and method for delivery of phytochemicals |
WO2006102236A1 (en) | 2005-03-18 | 2006-09-28 | Caudill Seed Inc. | Cancer chemoprotective compositions and natural oils and methods for making same |
DE102005033616A1 (en) | 2005-07-19 | 2007-01-25 | Biopro Ag Biological Products | Production of Brassica extracts with high anti-cancer sulforaphane content involves degradation of plant material in presence of myrosinase enzyme and glucosinolate |
-
2005
- 2005-08-09 US US11/199,752 patent/US7744937B2/en not_active Expired - Fee Related
-
2006
- 2006-07-31 PL PL06118220T patent/PL1752052T3/en unknown
- 2006-07-31 EP EP06118220A patent/EP1752052B1/en not_active Not-in-force
- 2006-08-01 CA CA002554969A patent/CA2554969A1/en not_active Abandoned
- 2006-08-03 AU AU2006203321A patent/AU2006203321B2/en not_active Ceased
- 2006-08-04 NO NO20063553A patent/NO20063553L/en not_active Application Discontinuation
- 2006-08-04 NZ NZ548951A patent/NZ548951A/en not_active IP Right Cessation
- 2006-08-08 BR BRPI0603903-0A patent/BRPI0603903A/en not_active IP Right Cessation
- 2006-08-08 RU RU2006128829/15A patent/RU2378002C2/en not_active IP Right Cessation
- 2006-08-08 CN CNA2006101513170A patent/CN1935003A/en active Pending
- 2006-08-08 AR ARP060103460A patent/AR054902A1/en unknown
- 2006-08-08 UA UAA200608875A patent/UA92140C2/en unknown
-
2010
- 2010-01-14 US US12/687,490 patent/US20100124598A1/en not_active Abandoned
Patent Citations (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4083836A (en) * | 1974-05-17 | 1978-04-11 | Alfa-Laval Ab | Production of rapeseed protein concentrate for human consumption |
US5043178A (en) * | 1988-02-09 | 1991-08-27 | Kraft General Foods, Inc. | Method for the extraction of roasted and ground coffee |
US5077071A (en) * | 1989-09-06 | 1991-12-31 | Epe Incorporated | Oil extrusion process |
US5725895B1 (en) * | 1995-09-15 | 2000-10-10 | Hopkins J School Of Medicine | Method of preparing food product from cruciferous seeds |
US5725895A (en) * | 1995-09-15 | 1998-03-10 | Johns Hopkins School Of Medicine | Method of preparing a food product from cruciferous seeds |
US5968567A (en) * | 1995-09-15 | 1999-10-19 | John Hopkins School Of Medicine | Method of preparing a food product from cruciferous sprouts |
US5968505A (en) * | 1995-09-15 | 1999-10-19 | Johns Hopkins School Of Medicine | Cancer chemoprotective food products |
US6177122B1 (en) * | 1995-09-15 | 2001-01-23 | Johns Hopkins School Of Medicine | Cancer chemoprotective food products |
US5686108A (en) * | 1995-09-27 | 1997-11-11 | Amway Corporation | Brassica vegetable supplement and process for manufacture |
US5882646A (en) * | 1995-09-27 | 1999-03-16 | Amway Corporation | Brassica vegetable supplement and process for manufacture |
US6086936A (en) * | 1995-12-14 | 2000-07-11 | Kal Kan Foods, Inc. | High temperature/ultra-high pressure sterilization of foods |
US6117460A (en) * | 1996-12-16 | 2000-09-12 | Kortschack; Fritz | Method of producing stable meat products and sausages, produced in the presence of microorganisms |
US6242018B1 (en) * | 1997-04-11 | 2001-06-05 | Johns Hopkins School Of Medicine | Cancer Chemoprotective food products |
US7303770B2 (en) * | 1997-04-11 | 2007-12-04 | Johns Hopkins School Of Medicine | Cancer chemoprotective food products |
US6521818B1 (en) * | 1998-07-01 | 2003-02-18 | John Hopkins School Of Medicine | Development of novel highly chemoprotectant crucifer germplasm |
US6348220B1 (en) * | 1999-04-09 | 2002-02-19 | Rutgers, The State University Of New Jersey | Phenethylisothiocyanate nutraceutical compositions and methods |
US20020015722A1 (en) * | 1999-05-05 | 2002-02-07 | Herzog Leslie John | Food product |
US6361812B1 (en) * | 1999-11-18 | 2002-03-26 | The Procter & Gamble Co. | Products comprising an isothiocyanate preservative system and methods of their use |
US20030091518A1 (en) * | 1999-12-20 | 2003-05-15 | Gilles Pauly | Cosmetic and/or pharmaceutical preparations |
US20040052879A1 (en) * | 2000-05-30 | 2004-03-18 | Giampietro Ravagnan | Method for the extraction of pharmaceutically active products from spermatophyte plants, products thus obtained and their use in the medical field, in particular as substances with anti-tumoral activity |
US6812248B2 (en) * | 2000-07-05 | 2004-11-02 | John Hopkins University School Of Medicine | Prevention and treatment of degenerative diseases by glutathione and phase II detoxification enzymes |
US20040133936A1 (en) * | 2000-08-17 | 2004-07-08 | John Rossiter | Enzyme |
US7402569B2 (en) * | 2000-08-21 | 2008-07-22 | Brassica Foundation For Chemoprotection Research, Inc. | Treatment of Helicobacter with isothiocyanates |
US6737441B2 (en) * | 2000-08-21 | 2004-05-18 | Jed W. Fahey | Treatment of helicobacter with isothiocyanates |
US20020151505A1 (en) * | 2000-08-21 | 2002-10-17 | Fahey Jed W. | Treatment of helicobacter with isothiocyanates |
US20020090405A1 (en) * | 2000-09-15 | 2002-07-11 | Najla Guthrie | Components of canola for the treatment of cancer |
US6436450B1 (en) * | 2000-12-08 | 2002-08-20 | Access Business Group International Llc | Brassica vegetable composition and method for manufacture of same |
US20020147155A1 (en) * | 2001-04-06 | 2002-10-10 | Foster Warren G. | Prevention and treatment of endometriosis with aryl hydrocarbon receptor binding ligands |
US20050055744A1 (en) * | 2001-07-05 | 2005-03-10 | Carlos Quiros | Nucleic acids encoding glucosinolate biosynthesis enzymes and methods of their use |
US7407986B2 (en) * | 2001-12-18 | 2008-08-05 | Brassica Foundation For Chemoprotection Research, Inc. | Prevention and treatment of oxidative stress disorders by glutathione and phase II detoxification enzymes |
US20050042347A1 (en) * | 2002-01-28 | 2005-02-24 | Bathurst Christopher Francis | Composition |
US20060020046A1 (en) * | 2002-02-15 | 2006-01-26 | Dms Ip Assets B.V. | Compositions comprising lycopene for the treatment and prevention of angiogenesis associated pathologies |
US20040001817A1 (en) * | 2002-05-14 | 2004-01-01 | Giampapa Vincent C. | Anti-aging nutritional supplement |
US20030235634A1 (en) * | 2002-06-21 | 2003-12-25 | Access Business Group International Llc. | Extraction of non-polar isothiocyanates from plants and dietary supplements containing same |
US6824796B2 (en) * | 2002-06-21 | 2004-11-30 | Access Business Group International Llc | Extraction of non-polar isothiocyanates from plants |
US20070033675A1 (en) * | 2003-04-14 | 2007-02-08 | Piet Barten | Brassica plants with high levels of anticarcinogenic glucosinolates |
US20080107792A1 (en) * | 2003-07-31 | 2008-05-08 | Martine Elisa Verhoeyen | Use of Plants with Increased Levels of Flavonol Glycosides in Reducing Hypertension |
US20050031768A1 (en) * | 2003-08-07 | 2005-02-10 | Shiro Sakai | Fractionation of allyl isothiocyanate, p-hydroxybenzyl-isothiocyanate, protein and fiber from mustard |
US20050123560A1 (en) * | 2003-12-04 | 2005-06-09 | Sinnott Robert A. | High purity and water dispersible extract and formulations of larrea tridentata leaf resin, and methods of making and using the same |
US20060003073A1 (en) * | 2004-05-07 | 2006-01-05 | Etzel Mark R | Methods and compositions involving whey protein isolates |
US20060127996A1 (en) * | 2004-12-14 | 2006-06-15 | Johns Hopkins University | Method of extraction of isothiocyanates into oil from glucosinolate-containing plants and method of producing products with oil containing isothiocyanates extracted from glucosinolate-containing plants |
US20070031581A1 (en) * | 2005-08-09 | 2007-02-08 | Kraft Foods Holdings, Inc. | Chemoprotectants from crucifer seeds and sprouts |
US20070190209A1 (en) * | 2006-02-10 | 2007-08-16 | Mannatech, Inc. | All natural multivitamin and multimineral dietary supplement formulations for enhanced absorption and biological utilization |
US7371419B1 (en) * | 2006-12-29 | 2008-05-13 | Kraft Foods Holdings, Inc. | Method of enriching glucoraphanin in radish seed preparations |
Cited By (54)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10363236B2 (en) | 2011-01-03 | 2019-07-30 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US10273205B2 (en) | 2011-01-03 | 2019-04-30 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating isothiocyanate functional surfactants and associated methods for treating biofilms |
US11654129B2 (en) | 2011-01-03 | 2023-05-23 | The William M Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US11407713B2 (en) | 2011-01-03 | 2022-08-09 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US11339125B2 (en) | 2011-01-03 | 2022-05-24 | The William M. Yarbrough Foundation | Use of isothiocyanate functional surfactants as NRF2 inducers to treat epidermolysis bullosa simplex and related diseases |
US11306057B2 (en) | 2011-01-03 | 2022-04-19 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating isothiocyanate functional surfactants and associated methods for treating biofilms |
US10888540B2 (en) | 2011-01-03 | 2021-01-12 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US10654799B2 (en) | 2011-01-03 | 2020-05-19 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating isothiocyanate functional surfactants and associated methods for treating biofilms |
US9771322B2 (en) | 2011-01-03 | 2017-09-26 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US9828337B2 (en) | 2011-01-03 | 2017-11-28 | The William M. Yarbrough Foundation | Lysine derivative having an isothiocyanate functional group and associated method of use |
US10647668B2 (en) | 2011-01-03 | 2020-05-12 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US10640464B2 (en) | 2011-01-03 | 2020-05-05 | The William M. Yarbrough Foundation | Use of isothiocyanate functional surfactants as Nrf2 inducers to treat epidermolysis bullosa simplex and related diseases |
US9932306B2 (en) | 2011-01-03 | 2018-04-03 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US9951005B2 (en) | 2011-01-03 | 2018-04-24 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant formulation and associated method of use |
US9951004B2 (en) | 2011-01-03 | 2018-04-24 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US9951003B2 (en) | 2011-01-03 | 2018-04-24 | The William M. Yarbrough Foundation | Isothiocyanate functional compound and associated method of use |
US11279674B2 (en) | 2011-01-03 | 2022-03-22 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US9962361B2 (en) | 2011-01-03 | 2018-05-08 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US10308599B2 (en) | 2011-01-03 | 2019-06-04 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
US10308600B2 (en) | 2011-01-03 | 2019-06-04 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
US10287246B2 (en) | 2011-01-03 | 2019-05-14 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating isothiocyanate functional surfactants and associated methods for treating biofilms |
US9585860B2 (en) | 2011-01-12 | 2017-03-07 | The William M. Yavbrough Foundation | Method for treating eczema |
US10111851B2 (en) | 2011-01-12 | 2018-10-30 | The William M. Yarbrough Foundation | Method for treating eczema |
US9649290B2 (en) | 2011-01-12 | 2017-05-16 | The William M. Yarbrough Foundation | Method for treating eczema |
US9655874B2 (en) | 2011-01-12 | 2017-05-23 | The William M. Yarbrough Foundation | Method for treating eczema |
US9687463B2 (en) | 2011-01-12 | 2017-06-27 | The William M. Yarbrough Foundation | Method for treating eczema |
US10532039B2 (en) | 2011-02-08 | 2020-01-14 | The William M. Yarbrough Foundation | Method for treating psoriasis |
US11517552B2 (en) | 2011-02-08 | 2022-12-06 | The William M. Yarbrough Foundation | Method for treating psoriasis |
US10765656B2 (en) | 2012-07-26 | 2020-09-08 | The William M. Yarbrough Foundation | Isothiocyanate functional compounds augmented with secondary antineoplastic medicaments and associated methods for treating neoplasms |
US10869854B2 (en) | 2012-07-26 | 2020-12-22 | The William M. Yarbrough Foundation | Method for treating skin cancer |
US10441561B2 (en) | 2012-07-26 | 2019-10-15 | The William M. Yanbrough Foundation | Method for treating benign prostatic hyperplasia (BPH), prostatitis, and prostate cancer |
US10471039B2 (en) | 2012-07-26 | 2019-11-12 | The William M. Yarbrough Foundation | Method for treating skin cancer |
US9949943B2 (en) | 2012-07-26 | 2018-04-24 | The William M. Yarbrough Foundation | Method for treating neurodegenerative diseases |
US10583108B2 (en) | 2012-07-26 | 2020-03-10 | The William M. Yarbrough Foundation | Inhibitors of macrophage migration inhibitory factor |
US10583107B2 (en) | 2012-07-26 | 2020-03-10 | The William M. Yarbrough Foundation | Method for treating benign prostatic hyperplasia (BPH), prostatitis, and prostate cancer |
US9931314B2 (en) | 2012-07-26 | 2018-04-03 | The William M. Yarbrough Foundation | Method for treating skin cancer |
US9839621B2 (en) | 2012-07-26 | 2017-12-12 | The William M. Yarbrough Foundation | Method for treating bladder cancer |
US11517553B2 (en) | 2012-07-26 | 2022-12-06 | The William M. Yarbrough Foundation | Isothiocyanate functional compounds augmented with secondary antineoplastic medicaments and associated methods for treating neoplasms |
US10111852B2 (en) | 2012-07-26 | 2018-10-30 | The William M. Yarbrough Foundation | Method for treating bladder cancer |
US10864187B2 (en) | 2012-07-26 | 2020-12-15 | The William M. Yarbrough Foundation | Method for treating infectious diseases with isothiocyanate functional compounds |
US10869855B2 (en) | 2012-07-26 | 2020-12-22 | The William M. Yarbrough Foundation | Method for treating benign prostatic hyperplasia (BPH), prostatitis, and prostate cancer |
US10434082B2 (en) | 2012-07-26 | 2019-10-08 | The William M. Yarbrough Foundation | Isothiocyanate functional compounds augmented with secondary antineoplastic medicaments and associated methods for treating neoplasms |
US10874630B2 (en) | 2012-07-26 | 2020-12-29 | The William M. Yarbrough Foundation | Inhibitors of macrophage migration inhibitory factor |
US10335387B2 (en) | 2012-07-26 | 2019-07-02 | The William M. Yarbrough Foundation | Method for treating infectious diseases with isothiocyanate functional compounds |
US10434081B2 (en) | 2012-07-26 | 2019-10-08 | The William M. Yarbrough Foundation | Inhibitors of macrophage migration inhibitory factor |
US11648230B2 (en) | 2012-07-26 | 2023-05-16 | The William M Yarbrough Foundation | Method for treating rheumatoid arthritis |
US9642827B2 (en) | 2012-07-26 | 2017-05-09 | The William M. Yarbrough Foundation | Method for treating skin cancer |
US9636320B2 (en) | 2012-07-26 | 2017-05-02 | The William M. Yarbrough Foundation | Method for treating skin cancer |
US10080734B2 (en) | 2012-07-26 | 2018-09-25 | The William M. Yarbrough Foundation | Method for treating autism and other neurodevelopmental disorders |
US11633376B2 (en) | 2012-07-26 | 2023-04-25 | The William M. Yarbrough Foundation | Method for treating metastatic prostate cancer |
US11633375B2 (en) | 2012-07-26 | 2023-04-25 | The William M. Yarbrough Foundation | Method for treating infectious diseases with isothiocyanate functional compounds |
CN105198782A (en) * | 2015-10-23 | 2015-12-30 | 河南科技学院 | Method for extracting, separating and purifying sulforaphene in radish seeds |
CN105713053B (en) * | 2016-03-26 | 2018-09-21 | 北京化工大学 | A kind of glucosinolate extraction separation method |
CN105713053A (en) * | 2016-03-26 | 2016-06-29 | 北京化工大学 | Extraction and separation method of glucosinolate |
Also Published As
Publication number | Publication date |
---|---|
BRPI0603903A (en) | 2007-03-27 |
US7744937B2 (en) | 2010-06-29 |
CA2554969A1 (en) | 2007-02-09 |
RU2006128829A (en) | 2008-02-20 |
RU2378002C2 (en) | 2010-01-10 |
EP1752052A3 (en) | 2007-08-29 |
PL1752052T3 (en) | 2013-02-28 |
UA92140C2 (en) | 2010-10-11 |
EP1752052B1 (en) | 2012-09-12 |
NZ548951A (en) | 2009-01-31 |
AU2006203321A1 (en) | 2007-03-01 |
US20070031581A1 (en) | 2007-02-08 |
CN1935003A (en) | 2007-03-28 |
AU2006203321B2 (en) | 2011-11-17 |
EP1752052A2 (en) | 2007-02-14 |
AR054902A1 (en) | 2007-07-25 |
NO20063553L (en) | 2007-02-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7744937B2 (en) | Chemoprotectants from crucifer seeds and sprouts | |
EP2014670B1 (en) | Production of Glucosinolates from Agricultural By-Products and Waste | |
Sikora et al. | The sources of natural antioxidants | |
AU710443B2 (en) | Cancer chemoprotective food products | |
Kuti et al. | Proximate composition and mineral content of two edible species of Cnidoscolus (tree spinach) | |
ES2704639T3 (en) | Stable and bioavailable compositions of lycopene isomers for skin and hair | |
CN101397314B (en) | Method of enriching glucoraphanin in radish seed preparations | |
Coppin | A study of the nutritional and medicinal values of Moringa oleifera leaves from sub-Saharan Africa: Ghana, Rwanda, Senegal and Zambia | |
Benhassaini et al. | The chemical composition of fruits of Pistacia atlantica desf. subsp. atlantica from Algeria | |
US20060020030A1 (en) | Enhanced purity trans-lutein-ester compositions and methods of making same | |
Polmann et al. | Non-conventional nuts: An overview of reported composition and bioactivity and new approaches for its consumption and valorization of co-products | |
US6770585B2 (en) | Momordica cochinchinensis (Spreng.) β-carotene and method | |
MXPA06009031A (en) | Chemoprotectants from crucifer seeds and sprouts | |
KR20110072772A (en) | Fractionation of kimchi and preparation method thereof | |
Khalil et al. | Chemical and technological studies on some medicinal plants | |
Haleem | Evaluation and application of some phytochemicals in pomegranate seed residues and guava seeds | |
JP2000300210A (en) | Carcinogenesis-suppressing extract for food | |
Chaichatoenaudomrung | Phytochemical profile and Bioactivities of Echinocactus grusonii extract |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |