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)
• • 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
  • 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
  • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
• • 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)
  • A61K36/35—Caprifoliaceae (Honeysuckle family)
• • 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)
  • A61K36/45—Ericaceae or Vacciniaceae (Heath or Blueberry family), e.g. blueberry, cranberry or bilberry
• • 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)
  • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
• • 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)
  • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
  • A61K36/736—Prunus, e.g. plum, cherry, peach, apricot or almond

Definitions

• the present invention relates to a method of preparation of edible berry derived compositions, particularly cherry, and to a method of use of the compositions derived from the berries as phytoceutical/nutraceutcal dietary supplements or as an additive to foods.
• the present invention provides a natural berry composition, particularly cherry, containing a mixture of anthocyanins, bioflavonoids and phenolics for use as dietary supplements or as a food additive.
• plant -derived compounds may also impart important positive pharmacological or "nutraceutical" traits to foods by way of their abilities to serve as cellular antioxidants by maintaining low levels of reactive oxygen intermediates, as anti- inflammatory agents by inhibiting prostaglandin synthesis, or as inhibitors of enzymes involved in cell proliferation. These activities may be important in ameliorating chronic diseases including cancer, arthritis, and cardiovascular disease (Kinsella et al . , Food Tech. 85- 89 (1993) .
• the dietary supplement/food industry and nutraceutical companies has the opportunity to employ compounds which can not only enhance food stability as effectively as synthetic antioxidants, but can also offer significant health benefits to the consumer.
• Cyanidin-3- glucosylrutinoside was also found in six out of the seven sour cherry varieties (Harborne, J. B., et al . , Phytochemistry 3:453-463 (1964)).
• Dekazos (Dekazos, E.D., J. Food Sci. 35:237-241 (1970)) reported anthocyanin pigments in MONTMORENCY cherry as peonidin- 3-rutinoside, peonidin and cyanidin along with cyanidin- 3-sophoroside, cyanidin-3-rutinoside and cyanidin-3- glucoside.
• cyanidin-3-glucosylrutinoside as well as cyanidin-3-glucoside, cyanidin-3-sophoroside and cyanidin-3-rutinoside were identified as main pigments in sour cherries.
• Chandra et al Choandra, A., et al . , J. Agric. Food Chem. 40:967- 969 (1992)
• cyanidin-3-sophoroside and cyanidin-3 -glucoside were the major and minor anthocyanins, respectively, in Michigan grown MONTMORENCY cherry.
• U.S. Patent No. 5,503,867 to Pleva describes the use of whole ground cherries and oat bran in ground meat .
• the amount of cherries used was 10 to 15% by weight and the oat bran is believed to be added to compensate for the juice in the cherries.
• the cherries definitely contribute a flavor to the meat and the palatability of the product is not universally accepted.
• the present invention relates to a method for producing a mixture comprising anthocyanins, bioflavonoids and phenolics from an edible berry as a composition which comprises:
• the present invention relates to a method for producing anthocyanins, bioflavonoids and phenolics from an edible berry as a composition which comprises :
• the present invention relates to a consumable composition which comprises in admixture:
• (b) a food grade carrier wherein the weight ratio of (a) to (b) is between about 0.1 to 100 and 100 to 0.1.
• the present invention relates to a method for feeding a mammal which comprises: feeding the mammal a consumable composition which comprises in admixture: (a) dried mixture of isolated anthocyanins, bioflavonoids and phenolics removed from an edible berry; and (b) a food grade carrier wherein the weight ratio of (a) to (b) is between about 0.1 to 100 and 100 to 0.1. It is preferred that the composition contain at least in part dried pulp of the berry.
• anthocyanins means the compounds that impart color in cherries .
• bioflavonoids means the isoflavonoids and flavonoid compounds contained in cherries .
• phenolics refers to compounds with a phenyl group and having one or more hydroxyl groups from cherries .
• Some of the edible berries are cranberry, raspberry, strawberry, blueberry, blackberry, elderberry, red grapes, gooseberry, Barbados cherry
• Figure 1 shows the structure of the isolated anthocyanins (colorants) from BALATON and MONTMORENCY cherries .
• the aglycone cyanidin has a hydroxyl group at position 3.
• FIGS. 2 and 3 are drawings showing the major bioflavonoids isolated from the cherries, as described in provisional application Serial No. 60/111,945, filed
• Figure 4 shows the phenolics isolated from tart cherries .
• Figure 5 shows the steps in the method of the present invention as described in Examples 1 and 2.
• Figure 6 is a schematic drawing showing the use of an open vessel 10 for holding resin beads, which remove anthocyanins and phenolics from the cherry juice. DESCRIPTION OF PREFERRED EMBODIMENTS
• the cherries used in the present invention can be sweet or sour, although the latter are preferred since they contain high levels of malic acid in addition to other organic acids which contributes to the sour taste of tart cherries .
• the method of the present invention isolates malic acid and other organic acids containing sugars which can be used in foods to provide tartness and flavor. Most preferred are the BALATON and MONTMORENCY cherries .
• the isolated mixture of anthocyanins, bioflavonoids and phenolics can be tableted and used as a natural nutraceutical/dietary supplement.
• the tablets provide a daily dose of the anthocyanins and bioflavonoids of about 1 to 200 mg, preferably a daily dose of 60 - 100 mg .
• One hundred (100) cherries provide 60 to 100 mg of anthocyanins.
• the phenolics ( Figure 4) are provided in an amount of 0.1 to 50 mg as a daily dose.
• One hundred cherries provide 1-50 mg of phenolics.
• the amount of the anthocyanins, bioflavonoids and phenolics can be adjusted by isolating the individual compounds and blending them together. It is preferred to use the natural mixture of the anthocyanins, bioflavonoids and phenolics which is isolated by the resin.
• the resin has a surface to which the anthocyanins, bioflavonoids and the phenolics are adsorbed.
• a preferred class of adsorptive resins are polymeric crosslinked resins composed of styrene and divinylbenzene such as, for example, the AMBERLITE series of resins, e.g., AMBERLITE XAD-4 and AMBERLITE XAD-16, which are available commercially from Rohm & Haas Co., Philadelphia, PA.
• polymeric crosslinked styrene and divinylbenzene adsorptive resins suitable for use according to the invention are XFS-4257, XFS- 4022, XUS-40323 and XUS-40322 manufactured by The Dow Chemical Company, Midland, Michigan, and the like.
• AMBERLITE XAD-16 styrene-divinyl- benzene cross-linked copolymer resin
• AMBERLITE XAD-16 commercially available from Rohm and Haas Company, and described in U.S. Patent No. 4,297,220 is used as the resin.
• This resin is a non-ionic hydrophobic, cross-linked polystyrene divinyl benzene adsorbent resin.
• AMBERLITE XAD-16 has a macroreticular structure, with both a continuous polymer phase and a continuous pore phase.
• the resin used in the present invention has a particle size ranging from 100-200 microns.
• AMBERLITE XAD adsorbent series which contain hydrophobic macroreticular resin beads, with particle sizes in the range of 100-200 microns
• AMBERLITES such as the AMERCHROM CG series of adsorbents, used with particle sizes in the range of 100-200 microns
• the AMBERLITE XAD-16 is preferred since it can be re-used many times (over 100 times) .
• the use of governmentally-approved resins in the present invention will be considered important and/or desirable.
• Any solvent can be used to remove the adsorbed anthocyanins, bioflavonoids and phenolics.
• Preferred are lower alkanols containing 1 to 4 carbon atoms and most preferred is ethanol (ethyl alcohol) since it is approved for food use.
• ethanol ethyl alcohol
• the ethanol is azeotroped with water; however, absolute ethanol can be used. Water containing malic acid and sugars in the cherries pass through the column. These are collected and can be used in foods as flavors.
• the anthocyanins, bioflavonoids and phenolics are preferably isolated from the BALATON and the MONTMORENCY cherries.
• the composition of the cherries is in part shown in part by U.S. application Serial No. 08/799,788 filed February 12, 1997 and in part U.S. application Serial No. 60/111,945, filed December 11, 1998.
• the Montmorency (Prunus cerasus) variety constitutes more than 95% of tart cherry cultivations in Michigan and USA.
• Balaton tart cherry ( P. cerasus) a new tart cherry cultivar, is being planted to replace Montmorency in several Michigan orchards. This cherry has higher anthocyanin contents and is regarded as a better variety.
• Balaton tart cherries have been reported (Wang, et al . , 1997; Chandry et al . , 1993). However, a detailed investigation of other phenolic compounds in Balaton tart cherry was not carried out before. Early studies have shown that MONTMORENCY cherry contains cyanidin-3- gentiobioside and cyanidin-3-rutinoside (Li, K. C, et al., J. Am. Chem. Soc . 78:979-980 (1956)). Cyanidin-3- glucosylrutinoside was also found in six out of the seven sour cherry varieties (Harbone, J.B., et al .
• Dekazos (Dekazos, E.D., J. Food Sci. 35:237-241 (1970)) reported anthocyanin pigments in MONTMORENCY cherry as peonidin- 3-rutinoside, peonidin and cyanidin along with cyanidin- 3-sophoroside, cyanidin-s-rutinoside and cyanidin-3- glucoside.
• cyanidin-3 -glucosylrutinoside as well as cyanidin-3 -glucoside, cyanidin-3-sophoroside and cyanidin-3-rutinoside were identified as main pigments in sour cherries.
• carrier or “bulking agent” is used to mean a composition which is added to increase the volume of the composition of the purified composition from the cherry.
• Preferred is dried cherry pulp.
• These include any edible starch containing material, protein, such as non-fat dry milk. Within this group are flour, sugar, soybean meal, maltodextrin and various condiments, such as salt, pepper, spices and herbs, for instance.
• the bulking agent is used in an amount between about 10 " " and 10 parts by weight of the mixture.
• the composition is introduced into the food in an amount between about 0.1 and 10 mg/gm of the active ingredients of the food.
• the amount is preferably selected so as to not affect the taste of the food and to produce the most beneficial result.
• the food can be high (wet) or low moisture (dry) as is well known to those skilled in the art.
• the tablets When used as a dietary supplement the tablets contain between 0.01 to 1 gram of active ingredient.
• the pulp was lyophilized at 15 °C.
• the juice was processed on AMBERLITE XAD-16 HP resin to produce cherry sour, anthocyanins, bioflavonoids and phenolics.
• the XAD-16 resin 1 kg, was washed with ethanol (1-2 L) and then washed with water (6 L) .
• the XAD-16 resin was allowed to stand in water for 1 hour before loading into a glass column (10 ID x 90 cm long) with a cotton plug.
• the packed column was washed with water (2 L) before loading the juice for separation. 800 mL juice was purified each time. The juice was added onto the surface of the column and allowed to settle with no flow. It was then eluted with water and the first 1 L was discarded.
• the red alcoholic solution was then evaporated under vacuum a (20 millitorr) to remove ethanol and the aqueous solution, stabilized with 50 ppm ascorbic acid, was lyophilized at 10°C. The red powder was collected and stored.
• red powders of Examples 1 and 2 were preferably mixed with dried pulp as a carrier and tableted into 1 to 1000 mg tablets including the carrier (1 adult daily dose) .
• Various food grade acids can be added to the isolated anthocyanins, bioflavonoids and phenolics to prevent decomposition. Preferably they do not add flavor. Ascorbic acid (vitamin C) is preferred. The acid can be added before or after the drying of the cherry compounds .
• EXAMPLE 3 As shown in Figure 6, an open vessel 10 is provided with an inlet line 11 and an outlet line 12, with valves 13 and 14, respectively. The resin beads 15 are provided in the open vessel 10. Water is introduced into the vessel 10 and then removed through outlet line 12 and discarded. The cherry juice (without the pulp or pits) as in Example 1 is introduced to the vessel 10 and allowed to stand for 25 minutes. The temperature of the water and juice is between about 20 and 30°C. The cherry juice residue containing malic acid and sugars is then removed through the outlet line 12 and retained as a food flavoring.
• the resin 15 in the vessel is then washed again with water from inlet line 11 and then removed and discarded through outlet line 12.
• the anthocyanins, bioflavonoids and phenolics on the resin particles are then extracted using 95% ethanol introduced through inlet line 11.
• the ethanol containing the anthocyanins, bioflavonoids and phenolics is removed from the vessel 10.
• the ethanol is removed from the anthocyanins, bioflavonoids and phenolics and dried using flash drying under nitrogen.
• the resulting powder is preferably then mixed with dried cherry pulp or other carrier as in Example 1.
• the resin particles are washed with water and then the resins and ethanol are recycled many times.
• a fluorescent probe 1, 6-diphenylhexatriene propionic acid
• This probe reacts with the free radicals generated during peroxidation, resulting in a decrease in fluorescence intensity with time.
• a peroxidation initiator such as ferrous metal ions or the free radical generator AAPH (Azobis- [2-amidino propane hydrochloride] ) is used to start the reaction, and the kinetics of fluorescence decrease are determined in the presence or absence of the antioxidant composition to be tested.
• An assay for a compound at a given concentration presently takes only twenty-one minutes, consumes only a few micrograms of lipid, and can be readily conducted with a simple fluorometer.
• LUVs Large unilamellar vesicles
• the dried film was resuspended in an aqueous buffer, and was repeatedly extruded through a polycarbonate filter of 100 nm pore size using a Liposofast piposome extruder (Avestin, Inc., Ottawa, Canada).
• the homogeneity of size (80-100 nm) and the unilamellar nature of the vesicles were confirmed using freeze-fracture scanning electron microscopy.
• the fluorescent probe, diphenylhexatriene- propionic acid (DPH-PA) was incorporated into the vesicles during preparation at a mole ratio of 1:350 (probe : lipid) .
• LUVs containing DPH-PA is suspended at a final concentration of 100 ⁇ M in 100 mM NaCl , 50 mM tris-HEPES buffer at pH 7.0.
• the fluorescent probe was excited at 384 nm and emission was monitored at 423 nm.
• Lipid oxidation is inhibited in the LUVs by addition of ferrous ions or the free radical generator AAPH; the progress was monitored by the decrease of the fluorescence intensity of DPH-PA resulting from reaction with free radicals generated over twenty-one minutes.
• a plot of the decrease of fluorescence intensity as a function of time was used to determine the kinetics of lipid oxidation. The results show that a mixture of the crude anthocyanin extract with ethylacetate was effective in inhibiting oxidation.
• Solvent extraction of the anthocyanins, bioflavonoids and phenolics can be used; however this is not preferred where the product is to be used as a food and for expense reasons . Where the preferred adsorbent resins are used, this step is unnecessary. It is also possible to separate and recombine the components using chromatography; however, for the purpose of the present invention, this is far too expensive since it involves high pressure liquid chromatography.
• Raspberries (339 g) , Blueberries (350 g) and Blackberries (670 g) were defrosted and blended separately with 500 mL of water in an industrial Waring blender. The mixtures were centrifuged at 10,000 rpm for 20 minutes and juice was decanted. The residues
• the pulp was lyophilized at 15°C.
• the juices were processed on XAD-16 resin to separate anthocyanins and phenolics from sugars and acids.
• the XAD-16 resin was processed on XAD-16 resin to separate anthocyanins and phenolics from sugars and acids.
• the column was eluted each time with ethanol (1.3 L, each for Raspberries and Blueberries and 1.0 L for Blackberries) and collected the red solution containing anthocyanins and phenolics (700 mL) . The column was then run dry and washed with 10 L of water before repeating the process .
• the red alcoholic solution was then evaporated under vacuum to remove ethanol and the aqueous solution, stabilized with 50 ppm ascorbic acid, was lyophilized at 10 °C.
• the red powders were collected and stored at - 20 °C. The results are shown in Table 1.

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• Health & Medical Sciences (AREA)
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• 1999
  • 1999-12-10 CN CNB998160563A patent/CN1269421C/zh not_active Expired - Fee Related
  • 1999-12-10 WO PCT/US1999/029441 patent/WO2000033670A1/en active Application Filing
  • 1999-12-10 JP JP2000586183A patent/JP4100871B2/ja not_active Expired - Fee Related
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