[go: up one dir, main page]

WO2011058773A1 - Composition à base d'huile - Google Patents

Composition à base d'huile Download PDF

Info

Publication number
WO2011058773A1
WO2011058773A1 PCT/JP2010/057878 JP2010057878W WO2011058773A1 WO 2011058773 A1 WO2011058773 A1 WO 2011058773A1 JP 2010057878 W JP2010057878 W JP 2010057878W WO 2011058773 A1 WO2011058773 A1 WO 2011058773A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
fucoxanthin
oily composition
composition according
oily
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.)
Ceased
Application number
PCT/JP2010/057878
Other languages
English (en)
Japanese (ja)
Inventor
匡彦 伊波
喜朗 飯沼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SOUTH PRODUCT Ltd
Original Assignee
SOUTH PRODUCT Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by SOUTH PRODUCT Ltd filed Critical SOUTH PRODUCT Ltd
Priority to JP2011540424A priority Critical patent/JP5691037B2/ja
Publication of WO2011058773A1 publication Critical patent/WO2011058773A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/15—Vitamins
    • A23L33/155—Vitamins A or D
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • 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
    • A61K31/12—Ketones
    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to an oily composition that can stably contain carotenoids over a long period of time.
  • Carotenoids are yellow-red-purple pigment components produced by green plants, molds, yeasts, mushrooms, bacteria, etc., and are generally known to have an antioxidant effect.
  • some carotenoids have various physiological activities.
  • astaxanthin contained in algae such as Haematococcus algae and chlorella and crustaceans such as shrimp and crab is effective against osteoporosis and muscular atrophy disorder. It has been reported that there is an effect (Patent Documents 1 and 2).
  • fucoxanthin contained in brown algae such as mozuku and having the following structure has an antitumor effect (Patent Document 3), a nerve cell protective effect (Patent Document 4), a blood glucose level increase suppressing effect (Patent Document 5), and an anti-tumor effect. It has been reported to have an obesity effect (Non-patent Documents 1 and 2) and the like.
  • Hayato Maeda Masashi Hosokawa, Tokutake Sashima, Nobuyuki Takahashi, Yeruo Kawada, Kazuo Miyashita, "Fucoxanthin and its metabolite, Fucoxanthinol, suppress adipocyte differentiation in 3T3-L1 cells", International Journal of Molecular Medicine, 18,147-152 (2005) .
  • an object of the present invention is to provide a composition that can stably contain carotenoids for a long period of time.
  • the present invention provides the following components (A) to (C); (A) Carotenoids (B) A carotenoid-containing oily composition containing (C) medium chain saturated fatty acid triglyceride (C) and tocotrienol.
  • the present invention is a method for stabilizing carotenoids characterized by dissolving carotenoids and tocotrienol in an oily base containing a medium-chain saturated fatty acid triglyceride.
  • decomposition of carotenoids can be suppressed and storage stability can be remarkably improved. Accordingly, it is possible to maintain a high carotenoid content and to sufficiently obtain physiological activities such as an antioxidant action, and to maintain a good appearance by suppressing the fading of the carotenoids.
  • the carotenoids of component (A) used in the present invention include carotenes which are hydrocarbons and xanthophylls containing oxygen in the chemical structure.
  • carotenes ⁇ -carotene, ⁇ - Examples of carotene, ⁇ -carotene, ⁇ -carotene, lycopene;
  • xanthophylls include derivatives such as fucoxanthin, lutein, astaxanthin, canthaxanthin, capsanthin, zeaxanthin, anthaxanthin, violaxanthin and esters thereof.
  • fucoxanthin and astaxanthin are more preferable, and fucoxanthin is particularly preferable.
  • Fucoxanthin is contained in, for example, brown algae belonging to the order of Chloraceae, Fucales, Laminariales, Cytosoniphones, etc., and these can be used as a raw material for extraction. it can.
  • brown algae the genus Pleurotus (Chordaceae) or Pleurosumaceae (Spermatochnaceae), Hidamata (Sargassaceaceae), Coleoptera (Laminariaceae) or Pleurotusaceae (Arianoceae) Brown algae belonging to (Schtosiphonaceae) and the like are preferred, and among the brown algae belonging to the above family, the genus Odonata of the family Nymphalidae (Cladosiphon okamuranus) or the moss of the family Nephonysaceae (C.
  • the brown algae used as the raw material for extraction is the release of zoospores from matured bodies, the generation of discoids or filaments from the zoospores, the formation of a solid body by the implantation of a disklike body or a filamentous body, Of the growth cycle of growing into a plate, it may be in any growth stage from a plate-like body or a filamentous body to a mature body, but a plate-like body or a filamentous body is preferred because it contains abundant fucoxanthin.
  • plate-like body or a filamentous body is located in the middle of the zoospore and a direct solid in the said growth cycle, and may be called with another name, in the present invention, all of these are included.
  • the plate-like body or the filamentous body may be naturally derived or artificially cultured, for example, cultured by the method described in JP-A-2004-35528. A board or thread can be used.
  • brown algae plate or filament for example, water, alcohols such as methanol, ethanol, propanol, ketones such as acetone, esters such as ethyl acetate, aliphatic hydrocarbons such as hexane, benzene, etc.
  • Fucoxanthin is extracted using an aromatic hydrocarbon, a halogen-based organic solvent such as chloroform, or a mixed solvent thereof. Since fucoxanthin is also used for foods and the like, it is preferably extracted with ethanol or hydrous ethanol.
  • Hydrous ethanol has a mixing ratio of ethanol: water of 40:60 to 99: 1, preferably 80:20 to 90:10 (mass ratio).
  • hydrous ethanol is preferable because the content of impurities such as chlorophyll is small and the yield of fucoxanthin and the like can be improved.
  • These solvents may be added in a mass ratio of 10: 1 to 1: 1, preferably 2: 1 to 4: 1, with respect to the disk or filament.
  • the extraction using the above solvent can be carried out by a conventional method.
  • the temperature is 15 to 60 ° C., preferably 20 to 40 ° C., preferably 0.5 to 16 hours, preferably Extraction may be performed for 2 to 8 hours.
  • stirring may be performed with an ultrasonic wave, a stirrer, or the like.
  • the solvent extract of brown algae obtained as described above contains fucoxanthin at a relatively high concentration, it may be blended as it is in the oily composition of the present invention.
  • the storage stability of fucoxanthin can be improved by further purification using.
  • purification means include column chromatography, liquid-liquid partition, etc., but column chromatography can be used because impurities such as chlorophylls contained in the extract can be effectively removed to improve storage stability. preferable.
  • column chromatography for example, a method using a reversed-phase synthetic adsorption resin such as styrene-divinylbenzene or methacrylic acid ester as a filler and eluting the adsorbed fraction with a water-ethanol solvent is suitable. .
  • the fraction fractionated by column chromatography may be used as it is, but further concentration, removal of the solvent, etc. may be performed by a conventional method such as concentration under reduced pressure.
  • concentration under reduced pressure By repeating such column chromatography, impurities such as chlorophylls are removed, and the storage stability of fucoxanthin can be further improved.
  • Chlorophylls can also be removed by cooling the solvent extract at about 0 to 10 ° C. and filtering off the precipitated solid. Further, by repeating operations such as silica gel column chromatography and recrystallization in addition to these operations, for example, highly pure fucoxanthin having a purity of 90% or more can be obtained.
  • the content of the component (A) in the oily composition of the present invention is 1.0 to 40.0% by mass (hereinafter simply indicated as “%”), preferably 3.0 to 10.0%. If it exceeds 40.0%, the solubility of the component (B) in the oil base is limited, which is not realistic.
  • component (B) medium chain saturated fatty acid triglyceride is used as the oily base.
  • This medium-chain saturated fatty acid triglyceride is composed of saturated fatty acids having 8 to 10 carbon atoms, and particularly has less body fat accumulation compared to long-chain fatty acids, so that it has 8 carbon atoms and 10 carbon atoms caprylic acid.
  • Tri (capryl / capric acid) glyceryl composed of an acid is preferably used.
  • Commercially available products of medium chain saturated fatty acid triglycerides include O.D. D. Examples thereof include O and scoley (both are tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Group, Inc.).
  • the content of component (B) in the oily composition of the present invention is preferably 50.0 to 99.0%, more preferably 85.0 to 95.0%.
  • the oil-based base used in the oil-based composition of the present invention includes short-chain fatty acid triglycerides, long-chain fatty acid triglycerides, as well as diglycerides, monoglycerides, and the like that do not impair the effects of the present invention.
  • the content of the medium-chain saturated fatty acid triglyceride in the entire oil base is preferably 80.0% or more, more preferably 90.0% or more, and particularly preferably 100%. preferable.
  • component (C) tocotrienol is used in the oily composition of the present invention.
  • component (C) tocotrienol There are four homologues of tocotrienol, ⁇ , ⁇ , ⁇ and ⁇ -, but any of them can be used in the present invention, and a mixture thereof may be used.
  • Examples of commercially available products of tocotrienols include Tocolit 92 (manufactured by Eisai Food Chemical Co., Ltd.) and Orizatocotrienol-90 (manufactured by Oriza Oil Chemical Co., Ltd.).
  • the content of the component (C) in the oily composition of the present invention is usually 0.1 to 6.0%, preferably 0.1 to 5.0%, more preferably 0.5 to 2.%. 0%. If it is lower than 0.1%, a sufficient effect may not be obtained. If it is higher than 6.0%, it may be difficult to dissolve in an oily base, or it may not be preferable in terms of cost.
  • an oil-soluble antioxidant selected from the group consisting of component (D) tocopherol (D1) and oil-soluble vitamin C derivative (D2) is preferably added.
  • component (D) tocopherol (D1) and oil-soluble vitamin C derivative (D2) is preferably added.
  • Tocopherol (D1) also has four homologues ⁇ , ⁇ , ⁇ , and ⁇ -, any of which may be used, or a mixture thereof.
  • examples of the oil-soluble vitamin C derivative (D2) include L-ascorbic acid fatty acid esters such as vitamin C palmitate and vitamin C stearate. In the present invention, one or more of these can be used.
  • vitamin C palmitate is preferably used because of its excellent carotenoid stabilizing effect.
  • the blending amount of component (D) in the oily composition of the present invention is usually 0.1 to 7.0%, preferably 0.5 to 5.0%, more preferably 0.5 to 2.%. 0%.
  • the blending mass ratio with respect to component (C) tocotrienol is preferably 1:50 to 50: 1 (component (C): component (D)).
  • component (D1) When only tocopherol (D1) is used as component (D), the blending mass ratio with respect to component (C) is preferably 1: 0.2 to 8 (component (C): component (D1)). Further, it is preferably 1: 0.8 to 5, particularly preferably 1: 0.4 to 6. Within such a range, an excellent carotenoid stabilizing effect can be obtained.
  • the total content of component (C) and component (D1) in the oily composition is usually 0.2 to 10%, preferably 1.0 to 8.0%, more preferably 1.0 to 4. 0%, in particular 2.0-4.0%. This range is preferable because the stability of carotenoids is increased.
  • the total blending mass ratio of the components (C) and (D1) to the component (A) carotenoids may be 1: 0.5 to 8 (component (A): component (C) + (D1)).
  • 1: 2 to 4 is more preferable.
  • the blending mass ratio with respect to the component (C) is usually 1: 0.2 to 8: 0.2. ⁇ 8, preferably 1: 0.3 to 6: 0.4 to 5, more preferably 1: 0.4 to 5: 0.4 to 2, thereby synergistically stabilizing carotenoids Can be obtained.
  • the total content of the component (C), the component (D1) and the component (D2) in the oily composition is usually 0.2 to 10%, preferably 1.0 to 8.0%, more preferably 1 0.0-4.0%, especially 2.0-4.0%. This range is preferable because the stability of carotenoids increases.
  • the total blending mass ratio of component (C), component (D1) and component (D2) to component (A) carotenoids is 1: 0.5 to 8 (component (A): component (C) + (D1 ) + (D2)), more preferably 1: 2-4.
  • the blending mass ratio of the component (D1) and the component (D2) is usually 1: 0.5 to 15 (component (D1): component (D2)), preferably 1: 1 to 10, more preferably 1: 1 to 4.
  • an optional component may be blended as necessary within a range not impairing the effects of the present invention.
  • an optional component for example, a fragrance, a cyclodextrin, or the like can be used for the purpose of masking an odor derived from seaweed.
  • the oily composition of the present invention is prepared by mixing and dissolving the above components (A), (C) and, if necessary, the component (D) in an oily base containing the component (B) by a conventional method. Can do.
  • the oily composition thus obtained can be blended in foods and drinks, pharmaceuticals, cosmetics and the like that are expected to have the antioxidant activity and the like possessed by carotenoids.
  • foods and drinks health foods in the form of soft capsules, hard capsules, tablets, granules, etc., or added to other foods and food materials to make foods and drinks such as soft drinks, drinks, jellies, candies, etc. it can.
  • it can be combined with a known pharmaceutical carrier to form a capsule, liquid, or the like.
  • cosmetics various forms such as emulsions, creams, lotions, body gels and the like can be used according to conventional methods.
  • an oily composition using fucoxanthin as a carotenoid can be used for pharmaceuticals and the like for the above-mentioned antitumor effect, nerve cell protective effect, blood glucose level increase inhibitory effect and the like.
  • the medium-chain fatty acid triglyceride also has an obesity-preventing effect, so that it is possible to make an excellent diet food due to the action of both.
  • Example 1 Preparation of fucoxanthin-containing oily composition: To the fucoxanthin concentrate obtained in Production Example 1, O.D. D. O (tri (capryl / capric acid) glyceryl; manufactured by Nisshin Eulio Co., Ltd.) and Tocorit 92 (Tocotrienol 70%, Tocophenol 30%; manufactured by Eisai Food Chemical Co., Ltd.), with a final concentration of fucoxanthin of 1%, Each was added and mixed so that the final concentration was 2%.
  • O.D. D. O tri (capryl / capric acid) glyceryl; manufactured by Nisshin Eulio Co., Ltd.) and Tocorit 92 (Tocotrienol 70%, Tocophenol 30%; manufactured by Eisai Food Chemical Co., Ltd.
  • Comparative Examples 1-11 An oily composition was prepared in the same manner as in Example 1 except that the oily base and the antioxidant were changed as shown in Table 1 below.
  • the oily base and antioxidant used are as follows.
  • Test example 1 Fucoxanthin storage stability test: The oil compositions obtained in Example 1 and Comparative Examples 1 to 11 were each placed in a 25 ml vial and stored in an oven at 40 ° C. The fucoxanthin content in the oily composition after 7 days was measured by HPLC under the above conditions. The results are also shown in Table 1.
  • Example 1 The amount of fucoxanthin after 7 days decreased by 7 to 18% in the comparative example, whereas no decrease was observed in Example 1.
  • Comparative Examples 3, 6, and 9 in which the same antioxidant as in Example 1 was added fucoxanthin decreased by 9%, 18%, and 9%, respectively, and Comparative Example using the same oily base as in Example 1 Since 1 and 2 also decreased by 10% and 7%, respectively, it was shown that the medium-chain saturated fatty acid triglyceride and tocotrienol of Example 1 are a particularly highly effective combination.
  • Examples 2-3 An oily composition was prepared in the same manner as in Example 1 except that the oily base and the antioxidant were changed as shown in Table 2 below.
  • the oily composition was placed in a 25 ml vial and stored in a 50 ° C. oven and a ⁇ 80 ° C. freezer.
  • the fucoxanthin content in the oily composition after 0, 1, 5, 11, 15 and 26 days was measured by HPLC under the above conditions.
  • the fucoxanthin content was determined as a relative value with the sample stored on the same day at ⁇ 80 ° C. as 100. The results are shown in Table 3.
  • Examples 4-7 Preparation of fucoxanthin-containing oily composition and fucoxanthin storage stability test: To the fucoxanthin concentrate obtained in Production Example 1, Skole 64 (tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.), Tocorit 92 (70% tocotrienol, 30% tocopherol; manufactured by Eisai Food Chemical Co., Ltd.) and Tocopherol (manufactured by Nisshin Oillio Co., Ltd.) was added and mixed so that the final concentration of fucoxanthin was 1% and the total final concentration of tocotrienol and tocopherol was 2%.
  • Skole 64 tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.
  • Tocorit 92 70% tocotrienol, 30% tocopherol; manufactured by Eisai Food Chemical Co., Ltd.
  • Tocopherol manufactured by Nisshin Oil
  • the blending mass ratio of tocotrienol and tocopherol was varied in the range of 1: 0.43 to 4.7.
  • the resulting oily composition was placed in a 25 ml vial and stored in an oven at 40 ° C. and a freezer at ⁇ 80 ° C.
  • the fucoxanthin content in the oily composition after 15 days was measured by HPLC under the above conditions.
  • the fucoxanthin content was determined as a relative value with the sample stored on the same day at ⁇ 80 ° C. as 100.
  • the thing which does not add an antioxidant was set as control. The results are shown in Table 4.
  • Table 4 shows that the use of tocotrienol and tocopherol improves the stability of fucoxanthin.
  • the blending mass ratio of tocotrienol, tocopherol and vitamin C palmitate was varied in the range of 1: 0.43: 0.48 to 4.29.
  • the resulting oily composition was placed in a 25 ml vial and stored in an oven at 40 ° C. and a freezer at ⁇ 80 ° C.
  • the fucoxanthin content in the oily composition after 15 days was measured by HPLC under the above conditions.
  • the fucoxanthin content was determined as a relative value with the sample stored on the same day at ⁇ 80 ° C. as 100.
  • the thing which does not add an antioxidant was set as control. The results are shown in Table 5.
  • Table 5 shows that a synergistic fucoxanthin stabilizing effect can be obtained by using vitamin C palmitate in addition to tocotrienol and tocopherol.
  • This fucoxanthin-containing fraction (1) was concentrated under reduced pressure to obtain a fucoxanthin concentrate (1).
  • the fucoxanthin content was analyzed by HPLC in the same manner as in Production Example 1.
  • chlorophyll a, c 1 and c 2 were quantitatively analyzed by HPLC under the following conditions. The results are shown in Table 7.
  • Examples 12-14 Preparation of fucoxanthin-containing oily composition and fucoxanthin storage stability test (light resistance): To the fucoxanthin concentrates (1) and (2) obtained in Production Example 2, scoray 64 (tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.), tocorit 92 (tocotrienol 70%, tocopherol 30%; Eisai Food Chemical Co., Ltd.) was added and mixed such that the final concentration of fucoxanthin was 1% and the final concentration of tocotrienol was 2% (Examples 12 and 13).
  • scoray 64 tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.
  • tocorit 92 tocotrienol 70%, tocopherol 30%
  • Eisai Food Chemical Co., Ltd. was added and mixed such that the final concentration of fucoxanthin was 1% and the final concentration of tocotrienol was 2% (Ex
  • Example 14 it replaced with the fucoxanthin concentrate and prepared the oil-based composition with the same composition using the reagent (The Wako Pure Chemical Industries Ltd. make, purity 94.0% or more) (Example 14).
  • the obtained oily composition was put in a 25 ml vial and stored under conditions of 5000 Lux and 40 ° C., and the fucoxanthin content in the oily composition after 0, 4, 5, 6, and 7 days was determined according to the conditions of Production Example 1 above. Measured by HPLC.
  • the fucoxanthin content was determined as a relative value with the sample stored on the same day at ⁇ 80 ° C. as 100. The results are shown in Table 8.
  • Example 15 Preparation of fucoxanthin soft capsule: A soft capsule having the following formulation was prepared. (Prescription) (per 400mg capsule) (1) Gelatin (film) 150mg (2) 250 mg of the oily composition of Example 1 400mg total This soft capsule is excellent in storage stability.
  • Example 16 Preparation of fucoxanthin-containing beverage: A beverage having the following formulation was prepared. (Prescription) (per 100ml) (1) Oily composition of Example 1 0.5 g (2) Lecithin (derived from soybean) 0.5g (3) Green tea extract (Sankyo Lifetech) 0.85g (4) Fructose 4g (5) L-ascorbic acid 0.05g (6) Fragrance 0.1g (7) Purified water Total 100g (100g with purified water) This beverage is excellent in storage stability.
  • oily composition of the present invention can stably hold carotenoids for a long period of time, it is extremely useful as a raw material used for health foods and pharmaceuticals.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Food Science & Technology (AREA)
  • Mycology (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Obesity (AREA)
  • Biochemistry (AREA)
  • Hematology (AREA)
  • Neurosurgery (AREA)
  • Endocrinology (AREA)
  • Dermatology (AREA)
  • Biomedical Technology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Toxicology (AREA)
  • Emergency Medicine (AREA)
  • Neurology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

La composition selon l'invention peut contenir à l'état stable un caroténoïde pendant une longue période de temps. La composition est caractérisée en ce qu'elle contient (A) un caroténoïde, (B) un triglycéride d'acide gras saturé à chaîne moyenne et (C) un tocotriénol.
PCT/JP2010/057878 2009-11-10 2010-05-10 Composition à base d'huile Ceased WO2011058773A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2011540424A JP5691037B2 (ja) 2009-11-10 2010-05-10 油性組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009-256746 2009-11-10
JP2009256746 2009-11-10

Publications (1)

Publication Number Publication Date
WO2011058773A1 true WO2011058773A1 (fr) 2011-05-19

Family

ID=43991437

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2010/057878 Ceased WO2011058773A1 (fr) 2009-11-10 2010-05-10 Composition à base d'huile

Country Status (2)

Country Link
JP (1) JP5691037B2 (fr)
WO (1) WO2011058773A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012214462A (ja) * 2011-03-30 2012-11-08 Fujifilm Corp カロチノイド含有組成物及びその製造方法
JP2012254959A (ja) * 2011-06-09 2012-12-27 Kikkoman Corp Ｉｌ−１７産生抑制剤
WO2015152080A1 (fr) * 2014-03-31 2015-10-08 小林製薬株式会社 Composition contenant de la vitamine b6
JP2015229656A (ja) * 2014-06-05 2015-12-21 花王株式会社 皮膚外用剤
JP2017046688A (ja) * 2015-08-31 2017-03-09 株式会社みやぎヘルスイノベーション 体重増加抑制用飲料組成物
CN107427452A (zh) * 2015-02-24 2017-12-01 化工产品开发公司Seppic 由褐藻配子体获得提取物及所述提取物作为化妆品抗老化活性成分的用途
US20220142965A1 (en) * 2015-04-13 2022-05-12 Algatechnologies Ltd. Compositions comprising carotenoids and use thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009161523A (ja) * 2007-12-12 2009-07-23 Fujifilm Corp 皮膚外用剤及びその製造方法
JP2009209146A (ja) * 2006-12-01 2009-09-17 Fujifilm Corp エマルション組成物、該エマルション組成物を含む食品及び化粧品

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002218994A (ja) * 2001-01-26 2002-08-06 Fuji Chem Ind Co Ltd 粗キサントフィル類の精製法
JP4297654B2 (ja) * 2002-07-08 2009-07-15 株式会社トロピカルテクノセンター フコキサンチンおよび／またはフコステロールの取得方法
TWI365716B (en) * 2003-12-02 2012-06-11 Suntory Holdings Ltd Oil or fat and oil compositions containing phospholipids and a long-chain polyunsaturated fatty acid supply compound, and food using same
US7780873B2 (en) * 2004-02-23 2010-08-24 Texas A&M University System Bioactive complexes compositions and methods of use thereof
EP1598060A1 (fr) * 2004-05-18 2005-11-23 Nestec S.A. Émulsion huile dans eau pour livraison
JP2009189335A (ja) * 2008-02-18 2009-08-27 Sanei Gen Ffi Inc カロテノイド色素含有乳化組成物及びその製造方法
WO2010112406A1 (fr) * 2009-03-30 2010-10-07 Basf Se Suspension stable, prête à l'emploi, de particules de caroténoïdes partiellement amorphes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009209146A (ja) * 2006-12-01 2009-09-17 Fujifilm Corp エマルション組成物、該エマルション組成物を含む食品及び化粧品
JP2009161523A (ja) * 2007-12-12 2009-07-23 Fujifilm Corp 皮膚外用剤及びその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
VIOLETA G. RANEVA: "Interaction between a-Tocopherol, Tocotrienols and Astaxanthin in Liposomes, Subjected to Lipid Peroxidation", JOURNAL OF OLEO SCIENCE, vol. 52, no. 7, 2003, pages 347 - 352, XP009097208 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012214462A (ja) * 2011-03-30 2012-11-08 Fujifilm Corp カロチノイド含有組成物及びその製造方法
JP2012254959A (ja) * 2011-06-09 2012-12-27 Kikkoman Corp Ｉｌ−１７産生抑制剤
WO2015152080A1 (fr) * 2014-03-31 2015-10-08 小林製薬株式会社 Composition contenant de la vitamine b6
JP2015196655A (ja) * 2014-03-31 2015-11-09 小林製薬株式会社 ビタミンｂ６含有組成物
JP2015229656A (ja) * 2014-06-05 2015-12-21 花王株式会社 皮膚外用剤
CN107427452A (zh) * 2015-02-24 2017-12-01 化工产品开发公司Seppic 由褐藻配子体获得提取物及所述提取物作为化妆品抗老化活性成分的用途
CN107427452B (zh) * 2015-02-24 2021-04-09 化工产品开发公司Seppic 由褐藻配子体获得提取物及所述提取物作为化妆品抗老化活性成分的用途
US20220142965A1 (en) * 2015-04-13 2022-05-12 Algatechnologies Ltd. Compositions comprising carotenoids and use thereof
JP2017046688A (ja) * 2015-08-31 2017-03-09 株式会社みやぎヘルスイノベーション 体重増加抑制用飲料組成物

Also Published As

Publication number Publication date
JPWO2011058773A1 (ja) 2013-03-28
JP5691037B2 (ja) 2015-04-01

Similar Documents

Publication Publication Date Title
JP5691037B2 (ja) 油性組成物
Zafar et al. Biochemical and immunological implications of lutein and zeaxanthin
Foo et al. Production of fucoxanthin-rich fraction (FxRF) from a diatom, Chaetoceros calcitrans (Paulsen) Takano 1968
Cha et al. Antiproliferative effects of carotenoids extracted from Chlorella ellipsoidea and Chlorella vulgaris on human colon cancer cells
Jaime et al. β-Carotene isomer composition of sub-and supercritical carbon dioxide extracts. Antioxidant activity measurement
Gille et al. Microalgae as a potential source of carotenoids: Comparative results of an in vitro digestion method and a feeding experiment with C57BL/6J mice
Xie et al. Production of three types of krill oils from krill meal by a three-step solvent extraction procedure
Yang et al. Chemistry and biochemistry of dietary carotenoids: bioaccessibility, bioavailability and bioactivities
Song et al. Effect of ultrasonic waves on the stability of all-trans lutein and its degradation kinetics
Morón-Ortiz et al. Ultrasound-assisted extraction of carotenoids from phytoene-accumulating Chlorella sorokiniana microalgae: Effect of milling and performance of the green biosolvents 2-methyltetrahydrofuran and ethyl lactate
EP3283089B1 (fr) Compositions comprenant des caroténoïdes et utilisation de celles-ci
Hajare et al. Extraction and quantification of antioxidant lutein from various plant sources
McCauley et al. Effects of nutrients and processing on the nutritionally important metabolites of Ulva sp.(Chlorophyta)
Akram et al. β-Carotene: beyond provitamin A
Pangestuti et al. Seaweed-derived carotenoids
Basily et al. Exploration of using the algal bioactive compounds for cosmeceuticals and pharmaceutical applications
Akkewar et al. A mechanistic review on growing multiple therapeutic applications of lutein and its global market research
WO2008023283A2 (fr) Esters de lutéine stabilisés
Patel et al. Marine Algae as a Source of Carotenoids: Bioactivity and Health Benefits
Garg et al. Microalgal nutraceuticals: unravelling solution to food-health nexus
Liau et al. Separation of sight-protecting zeaxanthin from Nannochloropsis oculata by using supercritical fluids extraction coupled with elution chromatography
Lee et al. Zeaxanthin: Sources, Properties and Benefits
Narayan et al. Composition, functionality and potential applications of seaweed lipids
Palmer et al. Biological activities of natural products from microalgae
Yan et al. The new products from brown seaweeds: Fucoxanthin and phlorotannins

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10829733

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2011540424

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10829733

Country of ref document: EP

Kind code of ref document: A1