WO1992003143A1 - Central nervous system activator and appetizing food additive - Google Patents
Central nervous system activator and appetizing food additive Download PDFInfo
- Publication number
- WO1992003143A1 WO1992003143A1 PCT/JP1991/000965 JP9100965W WO9203143A1 WO 1992003143 A1 WO1992003143 A1 WO 1992003143A1 JP 9100965 W JP9100965 W JP 9100965W WO 9203143 A1 WO9203143 A1 WO 9203143A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fatty acid
- acid ester
- lower fatty
- extract
- nervous system
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/75—Rutaceae (Rue 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)
- A61K36/75—Rutaceae (Rue family)
- A61K36/752—Citrus, e.g. lime, orange or lemon
-
- 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)
- A61K36/75—Rutaceae (Rue family)
- A61K36/754—Evodia
-
- 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)
- A61K36/75—Rutaceae (Rue family)
- A61K36/756—Phellodendron, e.g. corktree
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Definitions
- the present invention relates to a central nervous system activator and a palatability improving food additive.
- the present invention relates to a central nervous system activator and a palatability-enhancing food additive containing a processed plant of a Citrus plant or an extract thereof, or a limonoid.
- Plants belonging to the family Rutaceae such as bark of the yellowtail (Phello de nd ron amu rense) without bark, or powdered powdered powder (powder powder) It has been conventionally used as a stomachic. However, conventionally, they have not been used to activate the central nervous system.
- the present inventors have surprisingly found that a treated plant of a Citrus family plant or an extract thereof has a central nervous system activating effect.
- the present inventor has also found that when a treated plant of the aforementioned Rutaceae plant, in particular, an extract thereof is added to food, it has a remarkable palatability improving effect.
- the lower fatty acid ester monohalogenated lower alkane soluble part, the limonin fraction of the lower fatty acid ester-halogenated lower alkane soluble part and the obacnonone fraction of the lower fatty acid ester-halogenated lower alkyne soluble part combat the taste-enhancing food additive, which is characterized by being composed of an extracted product selected from the group consisting of:
- Plants belonging to the citrus family (Rutaceae) used in the present invention include plants belonging to the genus Yellowfin (Phellodendron) [for example, mushrooms (Phe1 1 odendronamu-rense Ru precht) j, orange rot (C) Itrus) (for example, lemon (C itrusli mon BUR.f.), oren (C itrussinensis OSBECK.), grapefruit (C it ru spa—radishi MAC F.)), and Goshu (E vodia) Et THOMSON), a plant belonging to the genus Dict amnu s [eg, Dict amnu sa 1 bus L.subsp. dasycarpus KI TAGAWA)].
- Preferred plants are yellowfin and its varieties [Obanokihida, Kekinoda (P. amu ren sse Ru p r. V a r.
- Taiwankihada P.wilssoniiiHayatataeetKanaehira. Goshu, Hachsen, etc.
- the whole or a part of the plant or a mixture thereof is used as a raw material.
- the plant part is preferably a stem, a leaf, a fruit or a pericarp, more preferably a bark (particularly a yellow genus plant), a root (particularly a genus plant) or a seed (particularly a citrus plant).
- the above-mentioned plants can be used, for example, by preparing a crushed, crushed, or pasted or fruitized plant treated product, or a dried plant powdered plant treated product.
- a preferred plant material is a powdered bark obtained by crushing, drying and powdering the bark of the yellow bark except for the pericarp (both limonin and obavacone, which will be described later, coexist in high content, and both enhance the interaction. Or concentrated juice of citrus fruits such as grapefruit or orange, powdered juice, or their seeds (high in limonin content).
- an extract of the processed plant can be used.
- the extraction-treated product that can be used in the present invention includes a lower alkane-insoluble portion of the processed plant material, a lower fatty acid ester extract of the lower alkyne-insoluble portion, and a lower fatty acid ester monohalogen of the lower fatty acid ester extract. Fraction of the lower fatty acid ester-halogenated lower alkane soluble part, or lovanin fraction of the lower fatty acid ester monohalogenated lower alkane soluble part, or a mixture thereof. It is.
- the extraction step can be performed, for example, as follows. First, the treated plant is refluxed with a lower alkane [ie, an alkane having 5 to 8 (preferably 5 to 7) carbon atoms, such as pentane, heptane or hexane, particularly II-hexane]. To be extracted.
- the extract residue or its dried product (hereinafter referred to as "alkane extract residue") has a central nervous system stimulating activity and a food taste improving activity.
- the alkane extraction residue is extracted with a lower fatty acid ester (for example, a lower alkyl ester of acetic acid, propionic acid or butyric acid, preferably an acetate ester, particularly ethyl acetate) under reflux.
- a lower fatty acid ester for example, a lower alkyl ester of acetic acid, propionic acid or butyric acid, preferably an acetate ester, particularly ethyl acetate
- the extract or a dried product thereof hereinafter referred to as “lower fatty acid ester extract” has a central nervous system activation activity and a food palatability improving activity.
- the above-mentioned lower fatty acid ester extract is converted into a lower fatty acid ester (for example, the above-mentioned compound, preferably an acetate ester, particularly, ethyl acetate) monohalogenated lower alkane (for example, chloride of a lower alkane having 1 to 4 carbon atoms) Product, especially black-mouthed form), if necessary, chromatographically treated while gradually changing the mixing ratio of the two to contain limonin-containing fractions (hereinafter referred to as limonin fractions) or ovacunone To obtain a fraction (hereinafter, referred to as “obaknon fraction”).
- limonin fractions limonin fractions
- ovacunone a fraction
- the central nervous system activator and the food additive of the present invention can contain the above-mentioned plant-treated product or extracted product alone or in combination thereof. Further, the central nervous system activator and the food additive of the present invention may contain limonides. Limonoids are oxidized derivatives of tetracyclic triterpenes having a bitter taste and glycosides thereof, which are contained in plants belonging to the family Rutaceae, Simaroubaceae, or the family Sendai (Mei iaceae). is there. Preferred compounds belonging to the limonides are limonin or ovavacnone and glycosides thereof. The limonoids may be those separated and purified from the above-mentioned or similar various extracted products, chemically synthesized, chemically or biochemically derived, or even biochemically synthesized. .
- the central nervous system stimulant of the present invention can be used in various dosage forms for oral administration, for example, tablets, powders, granules, capsules, syrups, elixirs or suspensions. These preparations can be prepared by a conventional method.
- the central nervous system activator of the present invention may further comprise a pharmaceutically acceptable carrier such as a pharmaceutically acceptable carrier, in addition to the above-mentioned plant-treated or extracted product or limonides (limonin, ovacnone, etc.) which are the active ingredients. It can contain a nontoxic carrier for oral use, a binder, a lubricant, a disintegrant, a coloring agent, a sweetener, a flavor and Z or a preservative.
- a pharmaceutically acceptable carrier such as a pharmaceutically acceptable carrier, in addition to the above-mentioned plant-treated or extracted product or limonides (limonin, ovacnone, etc.) which are the active ingredients.
- limonin, ovacnone, etc. can contain a nontoxic carrier for oral use, a binder, a lubricant, a disintegrant, a coloring agent, a sweetener, a flavor and Z or a preservative.
- the central nervous system activator according to the present invention can be orally administered to mammals (particularly humans).
- the subjects are those who have drowsiness or malaise and need to be removed or alleviated.
- the central nervous system stimulant according to the present invention can also be used as a senile dementia drug.
- the dosage of the central nervous system stimulant of the present invention varies depending on the patient, the condition to be treated, and / or the dosage form. (Obaku (As end), 10-20 OmgZkg per day, preferably 20-1 SOmgZkg per day, and for Limonides 0.05-: L O.OmgZkg per day, preferably 0.1-5. With OmgZkg, the expected effect can be obtained. In some cases, it is possible to increase the amount.
- These dosages can be administered once to several times a day.
- the term “preference improvement” refers to imparting a refreshing sensation, a refreshing sensation, a refreshing sensation, a refreshing sensation, and / or a clear sensation in addition to the original taste of the food.
- foods to which the taste is particularly improved by adding the food additive of the present invention include, for example, confectionery [eg, confectionery ( For example, candies, jellies), gums, bean jams, baked goods or battered confectionery (eg, cookies, biscuits), steamed confectionery], cocoa or cacao products (eg, chocolate, cocoa), frozen desserts (eg, ice) Confectionery, ice cream), drinks [eg, fruit juice drinks, soft drinks (carbonated drinks), health drinks], teas (eg, green tea, black tea), coffee, etc.
- confectionery eg, confectionery ( For example, candies, jellies), gums, bean jams, baked goods or battered confectionery (eg, cookies, biscuits), steamed confectionery], cocoa or cacao products (eg, chocolate, cocoa), frozen desserts (eg, ice) Confectionery, ice cream
- drinks eg, fruit juice drinks, soft drinks (carbonated drinks), health drinks] teas (eg, green tea, black tea), coffee
- the food additive of the present invention can be used in the same manner as other ordinary food additives, and may be simply mixed with the food ingredients together with other ingredients. Addition i varies depending on the type of food, but generally, 0.0005% or more, preferably 0.01% or more, of limonoids is blended per serving.
- the active ingredient of the food additive of the present invention improves the refreshing sensation on taste and also has a central nervous system activating activity, it has an awakeful use. It is highly preferable to add it to foods that make you sleepy (foods that make you sleepy) (for example, refreshing beverages, foods for drivers, and health foods for the elderly) because they work synergistically.
- foods that make you sleepy foods that make you sleepy
- refreshing beverages, foods for drivers, and health foods for the elderly because they work synergistically.
- n-hexane extraction residue A 600 g of oubak powder (Echida Kazoku Yakuhin) was inserted into the extraction tube of a Soxhlet extractor, and extraction was performed with 200 ml of n-hexane under reflux for 24 hours. About 570 g of n-hexane extraction residue remaining in the extraction tube was taken out (hereinafter referred to as n-hexane extraction residue A).
- n-hexane extraction residue A was inserted into an extraction tube of a Soxhlet extractor, and extraction treatment was performed with 200 ml of ethyl acetate under reflux for 24 hours.
- ethyl acetate extraction residue B Approximately 560 g of the ethyl acetate extraction residue remaining in the extraction tube
- ethyl acetate extract C Approximately 10 g was taken out. The same operation was repeated five times to obtain about 50 g of ethyl acetate extract C in total.
- a 50 g portion of the above ethyl acetate extract C was introduced into a glass column filled with 800 g of silica gel (Co-gel C-200; Wako Pure Chemical Industries, Ltd.), and a mixed solution of ethyl acetate-chloroform (100%) was added. (% By volume: 90% by volume).
- Fractions 28-35 (each fraction 150 m1) develop orange-red color with Ehrlich's reagent on thin-layer chromatograms and reach 210 nm. Showed absorption.
- the fractions 28 to 35 were purified with Clomouth formethanol to obtain about 5 g of colorless needle crystals. From the following physicochemical data, it was confirmed that the colorless needle-like crystals were limonin. (Hereinafter, the above colorless needle-shaped crystals are referred to as limonin crystals D.) Melting point: 298 to 299 ° C
- non-limonoid fraction F fractions 1 to 6, fractions 16 to 27 and fractions 36 to 100 did not develop orange-red color in the thin-layer chromatogram with Ehrlich's reagent.
- the entirety of these fractions is hereinafter referred to as non-limonoid fraction F.
- Berberine fraction G a fraction that is not eluted with an ethyl acetate-chloroform mixture is hereinafter referred to as Berberine fraction G.
- Example 1 The various extracted components obtained in Example 1 were given to mice, and the physiological activity was examined.
- powdered mouse feed (oriental yeast: powdered feed M) containing a soluble nitrogen-free substance (54.5%) as a main component, powdered oat powder (powder vermicelli), or n- Hexane extraction residue A or ethyl acetate extraction residue B was added to 5% by weight and mixed in a mortar.
- the ethyl acetate extract C, limonin crystal D, ovacnone crystal E, non-liminoid fraction F or berberine fraction G obtained in Example 1 above were each 0.1% by weight.
- the mixture was mixed in a mortar.
- Powder feed M was used as a control. The feed is changed daily with new ones.
- the limonin crystal D and the ovavacnone crystal E were suspended in a 0.25% aqueous solution of sodium carboxymethylcellulose and orally administered once a day at a dose of 20 Omg / kg.
- an aqueous solution of 0.25% sodium carboxymethylcellulose containing no active ingredient was used.
- a net of about 2 cm in height was placed at the bottom of the plastic cage for breeding, and mice were placed on the net to minimize the possibility of eating anything other than feed. Food and water were available ad libitum. Body weight was measured every two to three days, and the status of feed intake and changes in body weight were compared with those of the control group.
- ⁇ -Chloralose 500 mg / kg (narcotic) saline solution (0.1 lm lZl Og body weight) was intraperitoneally administered to the mice, and the righting reflex
- the sleep duration was the time from disappearance of the righting reflex to recovery of the righting reflex.
- the time until the head-on anti-If recovery was the point at which three head-on reflections occurred within one minute.
- Each group was administered within 3 minutes. Before anesthetic administration Body weight was measured.
- Table 1 below shows the measurement results.
- the sleep time reduction rate (s) is
- Opaque powder 150 Lactose (excipient) 99.4 Hydroxypropylcellulose (binder) 0.6 Magnesium stearate (lubricant) 2.0 Thoroughly mix the above components, After kneading the mixture by a conventional method, the mixture was subjected to granulation through a screen of an extrusion granulator, dried sufficiently, and then pressed into tablets. It should be noted that the components can be sufficiently mixed and then directly pressurized into tablets.
- Example 4 Citrus confectionery juice powder
- Example 4 Each freeze-dried fruit juice powder obtained in Example 4 was given to mice for physiological activity. The sex was examined. The operation was carried out in the same manner as in Example 2, except that powder feed M containing 5% by weight of each juice powder was used. The results are shown in the following Table 2 (administration for 5 days) and Table 3 (administration for 1 day).
- Tables 2 and 3 the sleep shortening rate (%) is the sleep time of each juice powder administration group when the sleep time of the control group is 100%.
- the value in the column of 5% lemon in Table 2 is P ⁇ 0.05
- the value in the column of 5% orange, 5% lemon and 5% grapefruit in Table 3 is P ⁇ 0.01. is there.
- Table 2 Administered juice Body weight Introduction time Sleep time Short sleep powder (N number) ( ⁇ ) (min) (min) Shrinkage (%) Control
- beverage compositions AE having the following composition (unit: g) and a beverage group for control were prepared.
- Vitamin C 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Vitamin 0.001 0.001 0.001 0.001 0.001 Vitamin B 2 0.001 0.001 0.001 0.001 0.001 Vitamin 0.002 0.002 0.002 0.002 0.002 0.002 Vitamin E 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Sugar 45.0 45.0 45.0 45.0 45.0 Fructose 10.0 10.0 10.0 10.0 10.0 10.0 Glucose 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Cuenoic acid 0.5 0.5 0.5 0.5 0.5 0.5 Lactic acid or resin
- a functional test was conducted on the obtained beverage by panelists of 20 adult men. The test was conducted after drinking 140 ml of the control beverage and then drinking 140 ml of the test beverage. Check whether the test beverage had a taste that was difficult to drink compared to the control beverage. Ease), and whether the test beverage gave a refreshing feeling as compared to the control beverage (refreshing feeling).
- the following table shows the number of panelists that were evaluated to give ease of drinking and a refreshing feeling. Beverage refreshing refreshment
- the obtained chewing gum was subjected to a sensory test with 20 adult male panelists. Inspection was conducted after 5 g of chewing gum for control was applied, and then 5 g of test chewing gum was applied. Whether or not the test chewing gum had a taste that was difficult to read compared to the chewing gum for control (easiness of reading) And whether or not the test chewing gum gave a refreshing feeling compared to the control chewing gum (refreshing feeling).
- the following table shows the number of panelists that were evaluated to give easy-to-read and refreshing feeling. Beverages Easy to refresh
- Example 4 Using the freeze-dried orange juice powder prepared in Example 4 above, chemically synthesized limonin and ovacnone, three types of candies (about 5 g each) having the following composition (unit: g) were prepared. When a panel test similar to that of Example 6 was performed, almost the same results as those of Examples 5 and 6 were obtained.
- Example 4 Using the freeze-dried grapefruit juice powder prepared in Example 4 above, chemically synthesized limonin and ovacunone, three kinds of cookies having the following composition (unit: S, 100 pieces) were prepared. A panel test similar to that of Example 6 was conducted, and substantially the same results as those of Examples 5 and 6 were obtained.
- Component A B C Component A B C
- the central nervous system activator of the present invention comprises Alternatively, the limonides generally contained in the extracted product or the plant of the family Michinaceae are used as the active ingredient, so that they can be contained in foods and ingested without difficulty.
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- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Alternative & Traditional Medicine (AREA)
- Epidemiology (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002067187A CA2067187C (en) | 1990-08-16 | 1991-07-19 | Central nervous system activator and taste enhancing food additive |
DE69123560T DE69123560T2 (de) | 1990-08-16 | 1991-07-19 | Aktivator des zentralnervensystems |
EP91913079A EP0498890B1 (en) | 1990-08-16 | 1991-07-19 | Central nervous system activator |
JP51285191A JP3442073B2 (ja) | 1990-08-16 | 1991-07-19 | 中枢神経賦活剤 |
US07/847,040 US5344648A (en) | 1990-08-16 | 1991-07-19 | Central nervous system activator and taste enhancing food additive |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21634690 | 1990-08-16 | ||
JP2/216346 | 1990-08-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992003143A1 true WO1992003143A1 (en) | 1992-03-05 |
Family
ID=16687114
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1991/000965 WO1992003143A1 (en) | 1990-08-16 | 1991-07-19 | Central nervous system activator and appetizing food additive |
Country Status (7)
Country | Link |
---|---|
US (1) | US5344648A (ja) |
EP (1) | EP0498890B1 (ja) |
JP (1) | JP3442073B2 (ja) |
CA (1) | CA2067187C (ja) |
DE (1) | DE69123560T2 (ja) |
ES (1) | ES2095945T3 (ja) |
WO (1) | WO1992003143A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007061028A (ja) * | 2005-09-01 | 2007-03-15 | Yasushi Oizumi | 学習記憶障害を改善する機能性食品 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69532816T2 (de) * | 1994-10-06 | 2005-03-17 | Staar Surgical Co., Monrovia | Intraokulare kontaktlinse |
AU724098B2 (en) | 1996-06-12 | 2000-09-14 | Kyowa Hakko Kogyo Co. Ltd. | Lipid metabolism improving agent |
US20020061339A1 (en) * | 2000-09-28 | 2002-05-23 | Martin Stogniew | Compositions and methods for use of extracts of rutaceae plants |
US6582735B2 (en) * | 2000-12-15 | 2003-06-24 | Npi, Llc. | Compositions and methods of use for extracts of magnoliaceae plants |
JP2004307396A (ja) | 2003-04-07 | 2004-11-04 | Kao Corp | デオドラント剤 |
ES2775734T3 (es) | 2015-08-31 | 2020-07-28 | Nutramax Lab Inc | Composiciones que comprenden magnolia, felodendron, teanina y/o proteína de suero |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57203014A (en) * | 1981-06-08 | 1982-12-13 | Osaka Chem Lab | Health food |
JPS5943928B2 (ja) * | 1980-08-14 | 1984-10-25 | 幸子 鈴木 | 血糖降下剤 |
JPH0283320A (ja) * | 1988-09-16 | 1990-03-23 | Toyotama Koryo Kk | 腫瘍予防剤 |
JPH02100650A (ja) * | 1988-10-07 | 1990-04-12 | Toyotama Koryo Kk | カンキツリモノイドを含有する飲食物 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS593255B2 (ja) * | 1980-07-10 | 1984-01-23 | 三洋電機株式会社 | 透明樹脂成形品の製造方法 |
JPS5943928A (ja) * | 1982-09-03 | 1984-03-12 | Toshiba Corp | ガスタ−ビン発電装置 |
-
1991
- 1991-07-19 EP EP91913079A patent/EP0498890B1/en not_active Expired - Lifetime
- 1991-07-19 JP JP51285191A patent/JP3442073B2/ja not_active Expired - Fee Related
- 1991-07-19 US US07/847,040 patent/US5344648A/en not_active Expired - Lifetime
- 1991-07-19 DE DE69123560T patent/DE69123560T2/de not_active Expired - Fee Related
- 1991-07-19 CA CA002067187A patent/CA2067187C/en not_active Expired - Lifetime
- 1991-07-19 ES ES91913079T patent/ES2095945T3/es not_active Expired - Lifetime
- 1991-07-19 WO PCT/JP1991/000965 patent/WO1992003143A1/ja active IP Right Grant
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5943928B2 (ja) * | 1980-08-14 | 1984-10-25 | 幸子 鈴木 | 血糖降下剤 |
JPS57203014A (en) * | 1981-06-08 | 1982-12-13 | Osaka Chem Lab | Health food |
JPH0283320A (ja) * | 1988-09-16 | 1990-03-23 | Toyotama Koryo Kk | 腫瘍予防剤 |
JPH02100650A (ja) * | 1988-10-07 | 1990-04-12 | Toyotama Koryo Kk | カンキツリモノイドを含有する飲食物 |
Non-Patent Citations (1)
Title |
---|
See also references of EP0498890A4 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007061028A (ja) * | 2005-09-01 | 2007-03-15 | Yasushi Oizumi | 学習記憶障害を改善する機能性食品 |
Also Published As
Publication number | Publication date |
---|---|
DE69123560D1 (de) | 1997-01-23 |
DE69123560T2 (de) | 1997-05-15 |
CA2067187C (en) | 2001-09-11 |
EP0498890B1 (en) | 1996-12-11 |
ES2095945T3 (es) | 1997-03-01 |
EP0498890A4 (en) | 1993-05-26 |
US5344648A (en) | 1994-09-06 |
JP3442073B2 (ja) | 2003-09-02 |
EP0498890A1 (en) | 1992-08-19 |
CA2067187A1 (en) | 1992-02-17 |
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