WO2014057727A1 - 柑橘類由来のノビレチン及びタンゲレチン含有物の製造方法及びその方法で得られたノビレチン及びタンゲレチン含有物 - Google Patents
柑橘類由来のノビレチン及びタンゲレチン含有物の製造方法及びその方法で得られたノビレチン及びタンゲレチン含有物 Download PDFInfo
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- 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
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- 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
- A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
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- 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
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- 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
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
Definitions
- the present invention relates to a method for producing a citrus-derived nobiletin and tangeretin-containing material.
- Nobiletin and tangeretin are a kind of polymethoxyflavonoids contained in citrus fruits.
- Nobiletin has a structure represented by the following formula (I).
- Tangeretine has a structure represented by the following formula (II).
- Nobiletin and tangeretin are said to have various pharmacological actions such as carcinogenesis-inhibiting action, blood sugar level-lowering action, and Alzheimer-type dementia prevention effect.
- Citrus fruits such as Ponkan and Sikhwasa are often used as raw materials for processing juices and jams.
- the pulp is mainly used, and the pulp and the peel after squeezing are discarded as a squeezed residue.
- nobiletin and tangeretin are more abundant in these juice residues than the pulp.
- a portion of the citrus juice residue is reused as essential oil extract or livestock feed, but is not expected as a raw material for food materials containing nobiletin and tangeretin.
- Patent Document 1 the description of which is incorporated herein by reference
- the fruit of Ponkan is extracted with 30% ethanol for 1 hour under reflux
- the obtained residue is extracted with hot water at 90 ° C. or higher for 1 hour, concentrated, decanted to obtain a supernatant, passed through a porous adsorption resin, and eluted with 70% ethanol to obtain nobiletin Is described.
- Patent Document 2 JP-A-2006-327998 discloses a residual oil obtained by distilling orange peel oil under reduced pressure to remove limonene.
- Patent Document 2 a method for producing polymethoxyflavonoids containing nobiletin and tangeretin by adding about 25 times volume of 70% ethanol and heating and refluxing after thin-film distillation of this kettle residue oil is disclosed.
- nobiletin and tangeretin-containing product Since nobiletin, tangeretin and other polymethoxyflavonoids contained in citrus have several pharmacological actions as described above, the demand is increasing. Therefore, if there is a method for efficiently producing a natural product containing nobiletin and tangeretin (hereinafter referred to as nobiletin and tangeretin-containing product), it is further expected that the nobiletin and tangeretin-containing product will be used as a food material.
- Patent Document 1 includes a step of performing extraction for 1 hour under reflux, and then performing extraction with hot water of 90 ° C. or higher, and a step of using a column. There is a problem that it is a risk to the person and a method that is inferior in economic efficiency.
- Patent Document 2 includes steps of producing kettle residue by vacuum distillation and thin-film distillation, and further requires a large amount of 70% ethanol, which is a dangerous and uneconomical method. is there.
- Non-Patent Document 1 has a nobiletin and tangeretin content of around 10% (w / w), so the nobiletin and tangeretin content is very small. There is a problem that it cannot be.
- the object of the present invention is safer than the prior art; it is excellent in economic efficiency and industrialization because the amount of solvent used and the number of steps are not small; and the content of nobiletin and tangeretin is high.
- the object is to provide a method for producing a large nobiletin and tangeretin-containing material, and a nobiletin and tangeretin-containing material obtained by the method.
- the present inventors obtained nobiletin and tangeretin lysate by subjecting citrus fruits to hot water treatment and solvent extraction treatment, or subjecting citrus fruits to warm solvent extraction treatment, Subsequently, this nobiletin and tangeretin lysate was treated with a dilute alkali to successfully obtain a high content of nobiletin and tangeretin-containing material. Further, such a method is safer than the methods described in Patent Document 1 and Patent Document 2 because the amount of solvent to be used is small, the temperature can be set low, and the method includes a simple process. It has been found that the method is excellent in property, economy and industrialization. The present invention has been completed based on such findings.
- a method for producing nobiletin and a tangeretin-containing material comprising the following steps (1-1) to (1-3) or step (2) and steps (3) and (4): Is done.
- (1-1) A step of obtaining a hot water treated product by treating citrus with hot water (1-2)
- Step of obtaining nobiletin and tangeretin concentrate by concentrating and / or drying the nobiletin and tangeretin lysate (4)
- step (5) is further included after the step (4).
- the step (1-2) removes moisture from the hydrothermal treated product by squeezing the filtration residue obtained by filtering the hydrothermal treated product or drying without squeezing. This is a step of obtaining a dried product.
- the step (1-1) is a step of treating the citrus fruits with hot water maintained at a temperature of 50 to 80 ° C. for 2 to 4 hours to obtain a hot water treated product.
- the step (2) is a step of treating citrus fruits with a nobiletin and tangeretin-soluble warm solvent maintained at a temperature of 50 to 70 ° C. for 1 to 8 hours to obtain a nobiletin and tangeretin lysate.
- the solvent that is soluble in nobiletin and tangeretin or the warm solvent that is soluble in nobiletin and tangeretin is 20 to 100% (v / v) ethanol, more preferably 20 to 50% (v / v) ethanol.
- the nobiletin and tangeretin concentrate is treated with a 1 to 3% (w / v) aqueous alkali solution at room temperature to obtain a nobiletin and tangeretin-containing material as an insoluble component. It is a process.
- the citrus fruit is Citrus depressa, C. unshiu, T. tachibana, C. leiocarpa, C. tardiva, C. succosa, C. succosa. C. kinokuni), C. erythrosa, C. sunki, C. deliciosa, C. nobilis, P. retuculata, D. tangerina, C. tangerina C. hanayu, C. reticulata, C. sunki, C. nippooreana, At least one plant selected from the group consisting of Ranuhi and Kiyomi.
- a nobiletin and tangeretin-containing material produced by the method of the present invention is provided.
- the content of nobiletin in the nobiletin and tangeretin-containing product is 45% (w / v) or more, and the content of tangeretin is 25% (w / v) or more.
- the content of synephrine in the nobiletin and tangeretin-containing product is less than the lower limit of detection.
- the content of nobiletin is 45% (w / v) or more, the content of tangeretin is 25% (w / v) or more, and synephrine A citrus-derived nobiletin and tangeretin-containing material having a content of less than the lower limit of detection is provided.
- a method for producing a fraction containing nobiletin and tangeretin in high concentration, comprising: an insoluble component acquisition step; and an ethanol elution step in which the alkali-insoluble component is eluted with ethanol.
- the citrus fruits include Citrus depressa, C. tachibana, C. leiocarpa, C. tardiva, C. succosa, C. kinokuni, C. kinokuni, C. ), Sunki (C. sunki), C. deliciosa, King (C. nobilis), Ponkan (C. reticulata), Dancy tangerina (C. tangera), C. hanayu, and Kourai Tachibana It is selected from the group consisting of (C. nippooreana). 3.
- a methanol-insoluble component acquisition step of acquiring methanol insoluble components by adding methanol to the concentrate and processing is further provided. 4).
- Heat drying in the residue obtaining step is performed under conditions of 50 to 70 ° C. and 15 to 45 minutes. 5.
- Heat drying in the residue obtaining step is performed under conditions of 60 ° C. and 30 minutes. 6).
- the hot water extraction in the residue obtaining step is performed in a warm bath at 50 to 80 ° C. for 2 to 4 hours. 7).
- the hot water extraction in the residue acquisition step is performed at 70 ° C. for 3 hours. 8).
- the residue after hot water extraction in the residue process is obtained using a filter having a retained particle diameter of 5 ⁇ m or less. 9.
- Heat drying in the ethanol extraction step is performed under conditions of 50 to 70 ° C. and 15 to 45 minutes. 10. Heat drying in the ethanol extraction step is performed at 60 ° C. for 30 minutes. 11. The ethanol extraction in the ethanol extract obtaining step is characterized in that 20-40% ethanol is used for 1-5 days at room temperature. 12 The ethanol extraction in the ethanol extract acquisition step is performed at room temperature using 30% ethanol. 13. The ethanol extract obtained in the ethanol extract obtaining step is concentrated at a temperature of 50 ° C. or lower for a predetermined time. 14 The alkali treatment in the alkali-insoluble component obtaining step is characterized by being carried out with 1 to 3% alkali solution at room temperature for 4 to 8 days. 15.
- Insoluble component acquisition in the alkali-insoluble component acquisition step is performed using a filter having a reserved particle diameter of 5 ⁇ m or less. 16.
- the insoluble component is eluted with methanol and filtered using a filter having a retained particle diameter of 5 ⁇ m or less. 17.
- a fraction containing high concentration of nobiletin and tangeretin produced by the production method described above.
- the nobiletin and tangeretin high-concentration fractions have a nobiletin content of 45% (w / v) and a tangeretin content of 25% (w / v) or more.
- the method of the present invention it is possible to produce a citrus-derived composition containing nobiletin and tangeretin at a high concentration as a method that is superior in safety, industrialization and economy as compared with the prior art. Is possible. Furthermore, according to the nobiletin and tangeretin-containing material of the present invention, the use of the nobiletin and tangeretin-containing material as a food material, for example, a food material or a food composition can be further expected. Moreover, it can use for the use of a pharmaceutical and cosmetics using the physiological activity of nobiletin and tangeretin.
- the nobiletin and tangeretin-containing product of the present invention is used alone, or together with other additives, powders, granules, tablets, liquids, pastes, capsules, gels for foods, cosmetics or pharmaceuticals, It can be provided in various forms such as a cream.
- the method for producing a nobiletin and tangeretin-containing material comprises subjecting a citrus fruit as a raw material to heating and solvent extraction, and subjecting the nobiletin and tangeretin lysate to a dilute alkali treatment, whereby sugars and fatty acids contained in citrus And a nobiletin and tangeretin-containing product containing a high concentration of nobiletin and tangeretin from which components such as are removed are produced as an insoluble component.
- the method of the present invention can be broadly classified into the first and second embodiments depending on the difference in the process of obtaining a nobiletin and tangeretin lysate.
- the first embodiment of the method of the present invention includes the following steps (1-1) to (1-3) and steps (3) and (4).
- (1-1) A step of obtaining a hot water treated product by treating citrus with hot water (1-2)
- the second aspect of the method of the present invention includes the following step (2) and steps (3) and (4).
- a step of obtaining nobiletin and tangeretin-containing materials as insoluble components by treating the nobiletin and tangeretin concentrate with a dilute alkali.
- the citrus fruits in the present invention are not particularly limited as long as they are citrus plants containing nobiletin and tangeretin.
- Citrus fruits in the present invention include, for example, oranges such as quinot, jaffa orange, joppa, navel orange, valencia orange, fukuhara orange, blood orange, bergamot; grapefruits such as orangero and grapefruit; , Citrus, Shikuwasa, Citron, Sudachi, Daidai, Shinhime, Bushkan, Yuuko, Tangerine, Yuzu, Lime, Lemon and other perfume citrus fruits; Cocktail fruit, Kawano Natsudaidai, Huangkan, Jabara, Shonan Gold, Sweety, Citrus such as summer mandarin oranges, Hassaku, Haruka, Koharu Haru, summer in Hinata; Aki no Shine (Decopon), Iyokan, Ehime fruit trial No.
- Kiyomi Saga fruit trial 34 (Decopon), Shion No Megumi, Shiranuhi (Dekopon), Seto, Seto Tangols such as Amifruit, Summer Fresh, Sweet Spring, Seminole, Tangero, Mineola; Ansei Kan, Buntans such as Kawachi Bankan, Ban Hakuan, Bungtan (Zapong); Wenzhou mandarin orange, Otsu four, Calamansea, Ganpei, Kishu mandarin orange, Koji (citrus), Sakurajima mandarin orange, Tachibana, Fujinaka mandarin orange, Ponkan, Mandarin orange Citrus genus such as Karachi, Kumquat genus such as long leaf gold citrus, Nagami Kinkan, Ningbo Kinkan, Fuzhou Kinkan, Hong Kong Kinkan, Marumi Kinkan etc., but preferably Citrus depressa, Citrus unshiu (C.
- the citrus fruit in the present invention may be one or more kinds, and may be a hybrid of the citrus fruit cited as the above specific example.
- the part of the citrus fruit that can be used in the present invention is not particularly limited as long as it contains nobiletin and tangeretin.
- pericarp juice residue (squeezed rice cake), pruned leaves and twigs, these A dried product or the like can also be used as a raw material.
- seeker, ponkan and the like it is preferable to use fruit, pericarp and squeezed residue since the content per unit weight of nobiletin and tangeretin is large.
- pruned leaves, twigs, and the like are produced in large quantities, although the content of nobiletin and tangeretin per unit weight is not as much as the pericarp. For this reason, there is a possibility that the load on the environment can be reduced by using these.
- the method of obtaining the citrus juice residue is not particularly limited, for example, the juice residue can be obtained by treating the citrus fruit with a press.
- a press machine is not specifically limited, It is preferable to use a roll press machine, a filter cloth press machine, a centrifugal filtration type
- the method for obtaining a dried product of citrus fruits and pericarp and juice residue is not particularly limited.
- citrus fruits can be dried by heating at 50 to 70 ° C. for 15 to 45 minutes to obtain a dried product of citrus fruits. it can. At this time, if it is dried at less than 50 ° C., it may not be able to be sufficiently dried within a short time of 15 to 45 minutes. If it is dried at a temperature exceeding 70 ° C., the components contained in citrus fruits May denature during drying. Therefore, when the citrus fruits are dried by heating, it is preferable to dry them at about 60 ° C. for about 30 minutes.
- a citrus fruit is treated with hot water to obtain a hydrothermally treated product.
- the sugar content can be removed by eluting the sugar content in the citrus fruits into the hot water.
- the hot water is preferably hot water maintained at a temperature of 50 ° C. or higher. When the temperature of hot water is less than 50 ° C., water-soluble impurities in citrus fruits may not be sufficiently removed. On the other hand, when the temperature of the hot water exceeds 80 ° C., there is a risk for the process operator and the fuel cost is also required. Therefore, the temperature of the hot water is more preferably 50 to 80 ° C.
- the time for treating the citrus fruits with hot water is not particularly limited as long as the water-soluble impurities in the citrus fruits can be sufficiently removed, but for example, 1 hour or longer, preferably 2 hours or longer, more preferably 2 to 2 hours. 4 hours.
- a preferred embodiment of the step (1-1) is, for example, a step of treating a citrus fruit with hot water maintained at a temperature of 50 to 80 ° C. for 2 to 4 hours to obtain a hot water treated product.
- a specific embodiment of the step (1-1) is not particularly limited. For example, a container obtained by adding citrus fruits to distilled water is placed in a warm bath and maintained at a temperature of 50 to 80 ° C. for 2 to 4 hours. The process to do is mentioned. Here, it is more preferable to perform the hydrothermal treatment under conditions of about 70 ° C. and about 3 hours.
- the hydrothermally treated product obtained in the step (1-1) is a mixture of citrus fruits and water. Therefore, from the viewpoint of the drying efficiency and the acquisition efficiency in the subsequent step (1-2), the hydrothermally treated product is subjected to a generally known solid-liquid separation means such as filtration using a filter having a reserved particle diameter of 5 ⁇ m or less. It is preferably obtained as a solid residue. When using a filter, the efficiency can be further increased if the retained particle diameter is 3 ⁇ m or less.
- a hydrothermally treated product or a residue of the hydrothermally treated product It is preferable to squeeze to obtain a juice residue.
- a step of obtaining a residue of the hydrothermally treated product or a step of obtaining a juice residue by squeezing the residue of the hydrothermally treated product can be provided after the step (1-1). .
- a hot-water treatment thing in addition to the hot-water treatment thing obtained at the process (1-1), reduces a water
- a dried product is obtained by drying the hot-water treated product obtained in step (1-1).
- This drying is not particularly limited as long as the moisture content of the hydrothermally treated product is less than several tens%, preferably less than 10%, but it is about 50 to 80 ° C. and several tens of minutes to several tens of hours. It is preferable that the drying is performed. If the hydrothermal treatment product is dried at less than 50 ° C., it may not be able to be sufficiently dried within a few tens of minutes. On the other hand, if the hydrothermal treatment product is dried at a temperature higher than 80 ° C., There is a possibility that components contained in the hydrothermally treated product are denatured during drying.
- the hydrothermally treated product is preferably dried at about 50 to 80 ° C. for several hours to several tens of hours using a dryer or the like, and more preferably at about 70 ° C. for 12 to 24 hours.
- a drying treatment a dried product containing nobiletin and tangeretin and having a water content of less than about 10% is obtained through step (1-2).
- step (1-3) the dried product obtained in step (1-2) is treated with a solvent that is soluble in nobiletin and tangeretin to obtain a nobiletin and tangeretin lysate.
- the solvent that is soluble in nobiletin and tangeretin is not particularly limited as long as it is a solvent that can dissolve nobiletin and tangeretin.
- a solvent that is readily soluble in nobiletin and tangeretin specifically, an organic solvent such as ethanol or ethyl acetate. And a mixed solvent of these organic solvents and water.
- a mixed solvent of ethanol and water when used as a solvent that is soluble in nobiletin and tangeretin, for example, it can be 20 to 100% (v / v) ethanol. However, if the ethanol concentration is less than 20% (v / v), the extraction efficiency may be poor, and even if the ethanol concentration exceeds 50% (v / v), the extraction efficiency is not greatly improved.
- the solvent that is soluble in tangeretin 20 to 50% (v / v) ethanol is preferable, and 30% (v / v) ethanol is more preferable from the viewpoint of extraction efficiency, safety, and industrialization.
- the treatment conditions in the step (1-3) are not particularly limited as long as nobiletin and tangeretin in the dried product are suitable for dissolving in the solvent, and the concentration of nobiletin and tangeretin in the solution is appropriately sampled. However, it can be carried out under conditions of 1 to 5 days at room temperature, and preferably 3 days at room temperature from the viewpoint of extraction efficiency.
- the recovery rate of nobiletin and tangeretin in the nobiletin and tangeretin lysate is not particularly limited, but 40% (23.6 mg / g) based on the assumed content (59 mg / g) of nobiletin and tangeretin contained in the citrus fruits. ) Or more, preferably 70% (41.3 mg / g) or more, more preferably 90% (53.1 mg / g) or more, 95% (56.1 mg / g) It is still more preferable that it is above.
- the nobiletin and tangeretin lysate obtained by the step (1-3) contains a certain amount of solids. Therefore, from the viewpoint of the processing efficiency of the subsequent step (4), the nobiletin and tangeretin lysate obtained by the step (1-3) is filtered using a filter having a retained particle diameter of 10 ⁇ m or less, preferably a filter having a size of 3 ⁇ m or less. It is preferable to obtain it as a liquid component by using the solid-liquid separation means.
- the nobiletin and tangeretin lysate includes, in addition to the solid content-containing nobiletin and tangeretin lysate obtained in step (1-3), a liquid nobiletin and tangeretin lysate from which the solids have been removed. .
- step (2) citrus fruits are treated with a warm solvent that is soluble in nobiletin and tangeretin to obtain a nobiletin and tangeretin lysate.
- the citrus fruits used in the step (2) are a squeezed residue or a dried squeezed residue in order to efficiently elute the nobiletin and tangeretin in the citrus fruits with a warm solvent that is soluble in nobiletin and tangeretin. It is preferable.
- the warm solvent that is soluble in nobiletin and tangeretin is one in which the solvent that is soluble in nobiletin and tangeretin is maintained at 50 to 70 ° C, preferably about 60 ° C.
- the treatment time in step (2) is not particularly limited as long as it can sufficiently elute nobiletin and tangeretin in citrus into the solvent. For example, it is 1 hour or more, preferably 2 hours or more, more preferably 4-8 hours.
- the nobiletin and tangeretin lysate obtained by the solvent treatment in the step (2) is subjected to a solid-liquid separation means such as filtration using a cartridge filter having a holding particle diameter of 10 ⁇ m, as in the step (1-3). It is preferable to obtain it as a component.
- the nobiletin and tangeretin lysate obtained in step (1-3) or step (2) is concentrated, dried, or both to obtain a nobiletin and tangeretin concentrate ( 3).
- a method for concentrating nobiletin and tangeretin lysate is not particularly limited. For example, a method of volatilizing a solvent in nobiletin and tangeretin lysate over a predetermined time at a low temperature to form a nobiletin and tangeretin-containing concentrate in a dry state Is mentioned.
- the concentration of nobiletin and tangeretin is not particularly limited as long as the concentrated solvent of nobiletin and tangeretin is obtained by removing the solvent that is soluble in nobiletin and tangeretin to obtain a concentrated concentrate of nobiletin and tangeretin.
- the ethanol is concentrated at a temperature of 50 ° C. or lower for several tens of minutes to several hours, preferably 10 minutes to 2 hours.
- drying method of nobiletin and a tangeretin solution is not specifically limited, For example, the method of heat-drying or freeze-drying a nobiletin and a tangeretin solution or its concentrate is mentioned.
- the nobiletin and tangeretin concentrate is treated with a dilute alkali to obtain a nobiletin and tangeretin-containing product as an insoluble component.
- a dilute alkali treatment By treating the nobiletin and tangeretin concentrate with a dilute alkali treatment, contaminant components such as fatty acids in the solution can be removed, and a nobiletin and tangeretin-containing product containing nobiletin and tangeretin at a high concentration can be obtained.
- the dilute alkali is not particularly limited as long as it decomposes impurities in nobiletin and tangeretin concentrate and does not decompose nobiletin and tangeretin.
- the dilute alkali is not particularly limited.
- the dilute alkali when it is an aqueous sodium hydroxide solution, it can be 0.1 to 20% (w / v), preferably 0.5 to 10% ( w / v), more preferably 1 to 3% (w / v).
- the dilute alkali treatment of the nobiletin and tangeretin concentrate in step (4) is performed, for example, by bringing the nobiletin and tangeretin concentrate into contact with a 1-3% (w / v) alkaline solution at room temperature for 1 to 6 days. can do.
- a specific embodiment of the step (4) is not particularly limited, but a mixture of nobiletin and tangeretin concentrate and 1% (w / v) aqueous sodium hydroxide solution is added at 1 to 2 at room temperature. Can be carried out by stirring for days.
- nobiletin and tangeretin-containing materials are obtained as insoluble components.
- solid-liquid separation means such as centrifugation and filtration can be used.
- the nobiletin and tangeretin-containing product can be subjected to a purification process.
- a nobiletin and tangeretin-containing product with reduced impurities as a liquid component can be obtained by solid-liquid separation of a mixture of a nobiletin and tangeretin-containing product collected and washed with water and a nobiletin and tangeretin-soluble solvent.
- the nobiletin and tangeretin-containing product obtained by the method of the present invention is a citrus-derived composition containing nobiletin and tangeretin at a high concentration as compared with the prior art.
- the content of nobiletin and tangeretin is 25% (w / V) or more nobiletin and tangeretin-containing material
- nobiletin content is 45% (w / v) or more
- tangeretin content is 25% (w / v) or more
- More preferred are nobiletin and tangeretin-containing materials.
- a preferred embodiment of the method of the present invention is a method for producing nobiletin and tangeretin-containing products, wherein the synephrine content is less than 0.5% (w / v), preferably the synephrine content is less than the detection lower limit.
- the contents of nobiletin, tangeretin and synephrine can be measured by the method described in the examples described later.
- the method of the present invention can include various processes in addition to the processes described above.
- the step before the step (4) may include a step of mixing an nobiletin and tangeretin concentrate and a nobiletin and tangeretin insoluble organic solvent and then obtaining an insoluble component by solid-liquid separation means.
- the process of obtaining a soluble component by a solid-liquid separation means, and the process of concentrating this soluble component can be added.
- the organic solvent insoluble in nobiletin and tangeretin is not particularly limited, and examples thereof include methanol and ethanol of 10% (v / v) or less.
- Extracting with 20 to 40% ethanol to obtain an extract; obtaining an ethanol extract; concentrating the ethanol extract at a low temperature to obtain a concentrate; and adding a dilute alkali to the concentrate it is expressed as a method for producing a fraction containing nobiletin and tangeretin in high concentration, comprising: an alkali-insoluble component obtaining step for obtaining an insoluble component by stirring treatment; and an ethanol elution step for eluting the alkali-insoluble component with ethanol. It is also possible.
- the nobiletin and tangeretin-containing products produced by the method of the present invention can be included in the present invention as another embodiment.
- the nobiletin and tangeretin-containing product of the present invention is not particularly limited as long as it is a citrus-derived composition that is produced by the method of the present invention and contains nobiletin and tangeretin at a high concentration as compared with the prior art.
- the content of nobiletin and tangeretin is preferably a nobiletin and tangeretin-containing product of 25% (w / v) or more, and the content of nobiletin is More preferred is a nobiletin and tangeretin-containing product having a content of 45% (w / v) or more and a tangeretin content of 25% (w / v) or more.
- the nobiletin and tangeretin-containing product of the present invention preferably has a synephrine content of less than 0.5% (w / v), and still more preferably has a synephrine content of less than the lower limit of detection.
- the content of nobiletin is 45% (w / v) or more
- the content of tangeretin is 25% (w / v) or more
- a citrus-derived nobiletin and tangeretin-containing material having a synephrine content of less than the lower limit of detection is provided.
- the sequwacer is washed with water, and then squeezing is performed with various presses that can squeeze the squeaker fruit as it is.
- a press for example, a roll press press that rotates by sandwiching a 10-20 mesh endless net between two compression rolls and squeezes the continuously supplied squeaker fruit with these two compression rolls.
- Examples include a soup machine, a filter cloth press machine that squeezes and squeezes the fruit of a seeker fruit wrapped in a filter cloth, a centrifugal filtration type separation device, and the like.
- a predetermined amount, for example, about 300 to about 500 g (wet weight) of the juice residue obtained by pressing the fruit juice is weighed.
- the residue is dried using, for example, a dryer at about 50 to about 70 ° C.
- the beaker is removed from the warm bath and allowed to cool naturally, and then, for example, a filter paper having a reserved particle diameter of 5 ⁇ m or less is laid on a Buchner funnel, the entire amount of the extract is suction filtered, and the residue is filtered off.
- the obtained residue is again dried using a dryer or the like at about 50 to about 70 ° C. in the same manner as described above, and weighed. Add 2 to 3 volumes of dry weight of ethanol and extract at room temperature for 2-4 days. Next, as in the above, the whole extract is suction filtered and the residue is filtered off. The filtrate is concentrated at about 30-40 ° C. for about 15 to about 60 minutes.
- aqueous sodium hydroxide solution 8 to 10 times the volume of 1% (w / v) aqueous sodium hydroxide solution is added and mixed well at room temperature. Continue stirring the mixture at room temperature for 1-2 days, eg, using a stirrer. Thereafter, for example, a filter paper having a retained particle diameter of 5 ⁇ m or less is set in a funnel and naturally filtered to separate a soluble component and an insoluble component. The insoluble component obtained is washed with 1 to 2 volumes of water. The remaining insoluble components are eluted with 5 to 10 volumes of ethanol. The ethanol soluble portion is then concentrated at room temperature for about 15 to about 60 minutes. The liquid volume after concentration is about 1/15 to 1/20 of the weight before concentration, and this liquid volume is measured.
- aqueous sodium hydroxide solution About 0.5 to 2% (w / v) aqueous sodium hydroxide solution, 8 to 10 times the volume of the solution, is added to this concentrated solution and mixed well. The mixture is then kept stirred at room temperature for 4-8 days, for example using a stirrer. Thereafter, for example, a filter paper having a reserved particle diameter of 5 ⁇ m or less is set in a funnel and naturally filtered, and the residue is separated by filtration. As described above, a fraction containing nobiletin and tangeretin at a high content can be obtained.
- peaks having retention times of about 8 to 9 minutes and about 11 to 12 minutes, respectively, were measured by a calibration curve method.
- Example 1 500 g of Shikuwasa squeezed rice cake from Higashimura, Okinawa Prefecture was thoroughly washed, 1800 mL of about 70 ° C. distilled water was added, and the mixture was placed in a hot water bath at about 70 ° C. for 3 hours.
- the obtained heat-treated product was subjected to suction filtration using a Buchner funnel on which a filter paper (manufactured by ADVANTEC, No. 131) having a reserved particle diameter of 3 ⁇ m was spread to obtain a residue.
- the residue was squeezed through a press.
- Example 2 500 g of Shikuwasa squeezed rice cake from Higashimura, Okinawa Prefecture was thoroughly washed, 1800 mL of about 70 ° C. distilled water was added, and the mixture was placed in a hot water bath at about 70 ° C. for 3 hours.
- the obtained heat-treated product was subjected to suction filtration using a Buchner funnel on which a filter paper (manufactured by ADVANTEC, No. 131) having a reserved particle diameter of 3 ⁇ m was spread to obtain a residue.
- Example 3 50 g (wet weight) of squeezer squeezed was weighed and dried at about 60 ° C. for 30 minutes using a dryer (manufactured by Panasonic, product number EH5101P Turbo Dry) to obtain 15 g of dried peel. To the obtained dried peel, 100 mL of distilled water at about 70 ° C. was added, placed in a hot water bath at about 70 ° C., and extracted by heating for 3 hours. The obtained extract was subjected to suction filtration using a Buchner funnel on which a filter paper (manufactured by ADVANTEC, No. 131) having a reserved particle diameter of 3 ⁇ m was spread to obtain a residue.
- a filter paper manufactured by ADVANTEC, No. 131
- the obtained residue was dried, 100% (v / v) ethanol having a volume twice the weight was added thereto, and ethanol extraction was performed at room temperature for 3 days.
- the filtrate was obtained by suction filtration using a Buchner funnel on which filter paper (No. 131, manufactured by ADVANTEC) having a reserved particle diameter of 3 ⁇ m was laid (“After ethanol extraction (1)” in Table 3).
- the obtained filtrate was concentrated with a rotary evaporator to obtain 1.15 g of a concentrated solution in a dry state.
- 10% (v / v) methanol, which is twice the weight of the obtained concentrated solution was added and dissolved, and centrifuged at 4 ⁇ 15 g for 30 minutes at room temperature. Separated.
- Example 4 The following powders containing a high concentration of nobiletin and tangeretin in lots 1 to 3 were obtained.
- the precipitate was freeze-dried, and 92.6 g of a powder after washing with water was obtained.
- the powder after washing with water again was dissolved in ethanol and suction filtered.
- the ethanol-eluting component was concentrated to obtain 58.2 g of a nobiletin and tangeretin-rich powder (nobiletin content 54.2 wt%, tangeretin content 36.0 wt%).
- the recovery rate was 24.3%.
- Example 5 55 g of dried dried squeezed rice cake was immersed in 450 ml of 30% (v / v) ethanol and extracted in a hot water bath at 70 ° C. for 2 hours. The extract was filtered through a nonwoven fabric. The extract was partially concentrated, weighed, and subjected to HPLC measurement to calculate the contents of nobiletin and tangeretin. In the same manner, 40% (v / v), 50% (v / v), and 70% (v / v) ethanol were used instead of 30% (v / v) ethanol. The recovery rate was calculated as 275 mg assumed to be contained in 55 g of dried squeezed rice cake. The results are shown in Table 5.
- Example 6 Extract 55kg of dried Siegwaser squeezed with 450L of 30% (v / v) ethanol at 60 ° C for 6 hours, let stand at room temperature overnight, filter and concentrate with cartridge filter (retained particle size 10 ⁇ m) Was reduced to 130 L to obtain a seeker extract. 30 ml of 1% (w / v) aqueous sodium hydroxide solution was added to 5 g of lyophilized powder (containing 195 mg of nobiletin (3.9% by weight) and 100 mg (2.0% by weight) of tangeretin) of this seeker extract. A treated product was obtained. The alkali-treated product was circulated and stirred for 16 hours and then centrifuged to obtain a precipitate 1.
- the precipitate 1 was washed with water and then centrifuged to obtain a precipitate 2. This step was performed until the supernatant became neutral.
- the filtrate obtained by centrifuging a precipitate obtained by adding 100% (v / v) ethanol to the dried precipitate (1.1 g) finally obtained was concentrated to obtain 344 mg of a powder.
- the powder contained 159 mg (46.3% by weight) nobiletin and 87 mg (25.3% by weight) tangeretin. According to this method, 80% or more of nobiletin and tangeretin contained in the lyophilized powder could be recovered.
- Example 7 Extract 55kg of dried Siegwaser squeezed with 450L of 30% (v / v) ethanol at 60 ° C for 6 hours, let stand at room temperature overnight, filter and concentrate with cartridge filter (retained particle size 10 ⁇ m) Was reduced to 130 L to obtain a seeker extract. 30 ml of 1 w / v% aqueous sodium hydroxide solution was added to 4.5 g of concentrated dried solid product of this seeker extract (containing nobiletin 175 mg (3.9 wt%) and tangeretin 90 mg (2.0 wt%)). A treated product was obtained. The alkali-treated product was circulated and stirred for 16 hours and then centrifuged to obtain a precipitate 1.
- the precipitate 1 was washed with water and then centrifuged to obtain a precipitate 2. This step was performed until the supernatant became neutral.
- the filtrate obtained by centrifuging 100% (v / v) ethanol to the dried precipitate (760 mg) finally obtained was concentrated to obtain 344 mg of a powder.
- This filtrate contained 159 mg (44.2 wt%) nobiletin and 87 mg (22.7 wt%) tangeretin. According to this method, 60% or more of nobiletin and tangeretin contained in the concentrate could be recovered.
- the obtained residue was dried, 30% (v / v) ethanol having a volume twice the weight was added thereto, and ethanol extraction was performed at room temperature for 3 days.
- the filtrate was obtained by suction filtration using a Buchner funnel on which filter paper (manufactured by ADVANTEC, No. 131) having a reserved particle diameter of 3 ⁇ m was spread.
- the obtained filtrate was concentrated with a rotary evaporator to obtain a concentrated solution in a dry state.
- water and ethyl acetate having an equal volume of the obtained concentrated liquid weight were added and dissolved, followed by liquid separation.
- the ethyl acetate soluble component was concentrated to obtain an extract having a nobiletin content of 24.4 wt% and a tangeretin content of 11.2 wt%.
- the obtained residue was dried, 100% (v / v) ethanol having a volume twice the weight was added thereto, and ethanol extraction was performed at room temperature for 3 days.
- the filtrate was obtained by suction filtration using a Buchner funnel on which filter paper (manufactured by ADVANTEC, No. 131) having a reserved particle diameter of 3 ⁇ m was spread.
- the obtained filtrate was concentrated with a rotary evaporator to obtain a concentrated solution in a dry state.
- water and ethyl acetate having an equal volume of the obtained concentrated liquid weight were added and dissolved, and partition extraction was performed.
- the ethyl acetate soluble component was concentrated to obtain an extract having a nobiletin content of 6.9 wt% and a tangeretin content of 5.2 wt%.
- the obtained residue was dried, 100% (v / v) ethanol having a volume twice the weight was added thereto, and ethanol extraction was performed at room temperature for 3 days.
- the filtrate was obtained by suction filtration using a Buchner funnel on which filter paper (manufactured by ADVANTEC, No. 131) having a reserved particle diameter of 3 ⁇ m was spread.
- the obtained filtrate was concentrated with a rotary evaporator to obtain a concentrated solution in a dry state. To this, water and ethyl acetate having an equal volume of the obtained concentrated liquid weight were added and dissolved, and liquid separation was performed.
- the ethyl acetate soluble component was concentrated to obtain an extract having a nobiletin content of 6.9 wt% and a tangeretin content of 5.2 wt%.
- extraction was performed using 30% (v / v) ethanol, 50% (v / v) ethanol and 70% (v / v) ethanol instead of 100% (v / v) ethanol, respectively. went.
- the results are shown in Table 6.
- the present invention is useful in the fields of foods, pharmaceuticals, and cosmetics, and is particularly useful in that it can be blended in or as a cream, gel cream, or lotion.
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Abstract
Description
(1-1)柑橘類を熱水で処理することにより熱水処理物を得る工程
(1-2)前記熱水処理物を乾燥することにより乾燥物を得る工程
(1-3)前記乾燥物をノビレチン及びタンゲレチン可溶性である溶媒で処理することによりノビレチン及びタンゲレチン溶解物を得る工程
(2)柑橘類をノビレチン及びタンゲレチン可溶性である温溶媒で処理することによりノビレチン及びタンゲレチン溶解物を得る工程
(3)前記ノビレチン及びタンゲレチン溶解物を濃縮及び/又は乾燥することにより、ノビレチン及びタンゲレチン濃縮物を得る工程
(4)前記ノビレチン及びタンゲレチン濃縮物を希アルカリで処理することにより、不溶性成分としてノビレチン及びタンゲレチン含有物を得る工程
(5)前記ノビレチン及びタンゲレチン含有濃縮物に10%(v/v)以下のメタノールを加えて処理し、メタノール不溶性成分を得る工程
1.柑橘類の果実を圧搾して得た搾汁残渣を、熱水洗浄して熱水洗浄残渣を取得する残渣取得工程と;前記除去残渣を乾燥させ、20~40%エタノールで抽出して抽出物を取得する、エタノール抽出物取得工程と;前記エタノール抽出物を低温で濃縮して濃縮物を得る濃縮物取得工程と; 前記濃縮物に希アルカリを加えて撹拌処理を行い、不溶性成分を取得するアルカリ不溶性成分取得工程と;前記アルカリ不溶性成分をエタノールで溶出させるエタノール溶出工程と;を備える、ノビレチン及びタンゲレチン高濃度含有画分の製造方法。
2.前記柑橘類は、シークワーサー(Citrus depressa)、タチバナ(C.tachibana)、コウジ(C.leiocarpa)、ギリミカン(C.tardiva)、ジミカン(C.succosa)、キシュウ(C.kinokuni)、コベニミカン(C.erythrosa)、スンキ(C.sunki)、チチュウカイマンダリン(C.deliciosa)、キング(C.nobilis)、ポンカン(C.retuculata)、ダンシータンジェリン(C.tangerina)、ハナユ(C.hanayu)、及びコウライタチバナ(C.nippokoreana)からなる群から選ばれるものであることを特徴とする。
3.濃縮物取得工程と、前記アルカリ不溶性成分取得工程の間に、前記濃縮物にメタノールを加えて処理し、メタノール不溶性成分を取得するメタノール不溶性成分取得工程をさらに備えることを特徴とする。
4.前記残渣取得工程における加熱乾燥が、50~70℃、15~45分の条件で行われることを特徴とする。
5.前記残渣取得工程における加熱乾燥が、60℃、30分の条件で行われることを特徴とする。
6.前記残渣取得工程における熱水抽出が、50~80℃の温浴中にて、2~4時間の条件で行われることを特徴とする。
7.前記残渣取得工程における熱水抽出が、70℃、3時間の条件で行われることを特徴とする。
8.前記残渣工程における熱水抽出後残渣の取得が、保留粒子径5μm以下のフィルターを用いて行われることを特徴とする。
9.前記エタノール抽出工程における加熱乾燥が、50~70℃、15~45分の条件で行われることを特徴とする。
10.前記エタノール抽出工程における加熱乾燥が、60℃、30分の条件で行われることを特徴とする。
11.前記エタノール抽出物取得工程におけるエタノール抽出は、20~40%エタノールを用いて、1~5日間、室温で行われることを特徴とする。
12.前記エタノール抽出物取得工程におけるエタノール抽出が、30%エタノールを用いて、室温で行われることを特徴とする。
13.前記エタノール抽出物取得工程で得られたエタノール抽出液を、50℃以下の温度で所定の時間濃縮することを特徴とする。
14.前記アルカリ不溶性成分取得工程におけるアルカリ処理が、1~3%のアルカリ液で、室温にて、4~8日間行われることを特徴とする。
15.前記アルカリ不溶性成分取得工程における不溶性成分の取得が、保留粒子径5μm以下のフィルターを用いて行われることを特徴とする。
16.前記不溶性成分をメタノールで溶出させ、保留粒子径5μm以下のフィルターを用いてろ過することを特徴とする。
17.前記された製造方法で製造された、ノビレチン及びタンゲレチン高濃度含有画分。
18.前記ノビレチン及びタンゲレチン高濃度含有画分中のノビレチンの含有量が45%(w/v)であり、タンゲレチンの含有量が25%(w/v)以上であることを特徴とする。
本発明に係るノビレチン及びタンゲレチン含有物の製造方法は、原料である柑橘類を加熱及び溶媒抽出に供して得たノビレチン及びタンゲレチン溶解物を希アルカリ処理に供することによって、柑橘類に含まれる糖質や脂肪酸などの成分が除去されたノビレチン及びタンゲレチンを高濃度で含有するノビレチン及びタンゲレチン含有物を不溶性成分として製造することを特徴とする方法である。本発明の方法は、ノビレチン及びタンゲレチン溶解物を得る工程の差異によって、第一及び第二の態様に大別できる。
(1-1)柑橘類を熱水で処理することにより熱水処理物を得る工程
(1-2)前記熱水処理物を乾燥することにより乾燥物を得る工程
(1-3)前記乾燥物をノビレチン及びタンゲレチン可溶性である溶媒で処理することによりノビレチン及びタンゲレチン溶解物を得る工程
(3)前記ノビレチン及びタンゲレチン溶解物を濃縮及び/又は乾燥することにより、ノビレチン及びタンゲレチン濃縮物を得る工程
(4)前記ノビレチン及びタンゲレチン濃縮物を希アルカリで処理することにより、不溶性成分としてノビレチン及びタンゲレチン含有物を得る工程
(2)柑橘類をノビレチン及びタンゲレチン可溶性である温溶媒で処理することによりノビレチン及びタンゲレチン溶解物を得る工程
(3)前記ノビレチン及びタンゲレチン溶解物を濃縮及び/又は乾燥することにより、ノビレチン及びタンゲレチン濃縮物を得る工程
(4)前記ノビレチン及びタンゲレチン濃縮物を希アルカリで処理することにより、不溶性成分としてノビレチン及びタンゲレチン含有物を得る工程
沖縄県東村産のシークワーサーの搾り粕500gをよく洗浄し、1800mLの約70℃の蒸留水を加えて約70℃の湯浴中に入れ、3時間加熱処理した。得られた加熱処理物を、保留粒子径3μmのろ紙(ADVANTEC社製、No.131)を敷いたブッフナーロートを用いて吸引ろ過し、残渣を得た。残渣を圧搾機にかけて搾汁した。
沖縄県東村産のシークワーサーの搾り粕500gをよく洗浄し、1800mLの約70℃の蒸留水を加えて約70℃の湯浴中に入れ、3時間加熱処理した。得られた加熱処理物を、保留粒子径3μmのろ紙(ADVANTEC社製、No.131)を敷いたブッフナーロートを用いて吸引ろ過し、残渣を得た。
シークワーサーの搾り粕50g(湿重量)を秤量し、ドライヤー(パナソニック社製、品番 EH5101P ターボドライ)を用いて、約60℃で30分間乾燥させ、乾燥果皮15gを得た。得られた乾燥果皮に100mLの約70℃の蒸留水を加えて約70℃の湯浴中に入れ、3時間加熱抽出した。得られた抽出液を、保留粒子径3μmのろ紙(ADVANTEC社製、No.131)を敷いたブッフナーロートを用いて吸引ろ過し、残渣を得た。
下記ロット1~3のノビレチン及びタンゲレチンを高濃度で含有する粉沫を得た。
乾燥シークワーサー搾り粕70kgを30%(v/v)エタノール450Lを用いて、60℃で2時間抽出を行った。抽出経過後1時間及び2時間の抽出物並びにその後濃縮した抽出物をサンプリングしてカートリッジフィルター(保持粒子径10μm)でろ過した後、ろ液を濃縮して溶液の量を130Lに減じた。当該溶液と同量(130L)の2%(w/v)水酸化ナトリウム水溶液を加え、溶液を室温で一晩攪拌した。その後、溶液を遠心分離して、沈殿粉沫319g(湿重量)を得た。得られた粉沫を水に浸漬した後にろ過するという操作を二度繰り返した。水で洗浄して再度ろ過した後に、ろ紙上の残渣をエタノールに浸漬させた。残渣を吸引ろ過し、得られたエタノール抽出液を濃縮し、ノビレチン及びタンゲレチン高含有粉沫62.5g(ノビレチン含有率42.8wt%、タンゲレチン含有率45.9wt%)を得た。結果を表4に示す。
乾燥シークワーサー搾り粕55kgを30%(v/v)エタノール450Lを用いて、60℃で1時間抽出を行い、室温で一晩静置後、カートリッジフィルター(保持粒子径10μm)でろ過した後、ろ液を濃縮して溶液の量を80Lに減じた。当該溶液と同量の2%(w/v)水酸化ナトリウム水溶液を加え、溶液を6℃に冷やしながら攪拌した。その後、溶液を遠心分離して、水酸化ナトリウム処理物1534gを得た。得られた水酸化ナトリウム処理物のうち1294gを水で洗浄した。その後遠心分離を行い、上清と沈殿物に分離した。沈殿物を凍結乾燥した後、水で洗浄した後の粉沫92.6gを得た。再度水洗浄した後の粉沫をエタノールに溶かし吸引ろ過を行った。エタノール溶出成分を濃縮し、ノビレチン及びタンゲレチン高含有粉沫58.2g(ノビレチン含有率54.2wt%、タンゲレチン含有率36.0wt%)を得た。回収率は24.3%であった。
乾燥シークワーサー搾り粕55kgを30%(v/v)エタノール450Lを用いて、60℃で1時間抽出を行い、室温で一晩静置後、カートリッジフィルター(保持粒子径10μm)でろ過した後、ろ液を濃縮して溶液の量を95Lに減じた。当該溶液の5Lをスプレードライし、90Lの濃縮液に同量の2%(w/v)水酸化ナトリウム水溶液を加え、溶液を20~25℃に維持して撹拌した。その後、溶液を遠心分離して、水酸化ナトリウム処理物を260g得た。この水酸化ナトリウム処理物を水で洗浄した。その後遠心分離を行い、沈殿物を凍結乾燥し、水洗浄した後の粉沫90.7gを得た。再度水洗浄した後の粉沫をエタノールに溶かし吸引ろ過を行った。エタノール溶出成分を濃縮し、ノビレチン及びタンゲレチン高含有粉末76.3g(ノビレチン含有率50.2wt%,タンゲレチン含有率31.2wt%)を得た。回収率は25.2%であった。
シークワーサーの搾り粕乾燥物55gを30%(v/v)エタノール450mlに浸し、70℃の湯浴中で2時間抽出を行った。抽出液を不織布でろ過をした。抽出液を一部濃縮し秤量、HPLC測定を行いノビレチン及びタンゲレチンの含量を算出した。同様の方法で、30%(v/v)エタノールの代わりに40%(v/v)、50%(v/v)、70%(v/v)エタノールを用いて行った。回収率は乾燥搾り粕55gに含まれていると想定される275mgで計算した。結果を表5に示す。
乾燥シークワーサー搾り粕55kgを30%(v/v)エタノール450L、60℃で6時間抽出を行い、室温で一晩静置後、カートリッジフィルター(保持粒子径10μm)でろ過、濃縮を行い溶液の量を130Lに減らして、シークワーサー抽出液とした。このシークワーサー抽出液の凍結乾燥粉末5g(ノビレチン 195mg(3.9重量%)、タンゲレチン100mg(2.0重量%)含有)に1%(w/v)水酸化ナトリウム水溶液を30ml加えて、シークワーサーアルカリ処理物を得た。このアルカリ処理物を16時間循環攪拌した後に遠心分離して、沈殿物1を得た。この沈殿物1を水で洗浄した後に、遠心分離して、沈殿物2を得た。この工程は上清液が中性になるまで行った。最終的に得られた沈殿物を乾燥したもの(1.1g)に100%(v/v)エタノールを加えたものを遠心分離して得たろ液を濃縮して粉沫344mgを得た。この粉沫には、ノビレチン159mg(46.3重量%)及びタンゲレチン87mg(25.3重量%)が含まれていた。本法によれば、凍結乾燥粉末に含まれていたノビレチン及びタンゲレチンを80%以上回収することができた。
乾燥シークワーサー搾り粕55kgを30%(v/v)エタノール450L、60℃で6時間抽出を行い、室温で一晩静置後、カートリッジフィルター(保持粒子径10μm)でろ過、濃縮を行い溶液の量を130Lに減らして、シークワーサー抽出液とした。このシークワーサー抽出液の濃縮乾固物4.5g(ノビレチン175mg(3.9重量%)、タンゲレチン90mg(2.0重量%)含有)に1w/v%水酸化ナトリウム水溶液を30ml加えて、シークワーサーアルカリ処理物を得た。このアルカリ処理物を16時間循環攪拌した後に遠心分離して、沈殿物1を得た。この沈殿物1を水で洗浄した後に、遠心分離して、沈殿物2を得た。この工程は上清液が中性になるまで行った。最終的に得られた沈殿物を乾燥したもの(760mg)に100%(v/v)エタノールを加えたものを遠心分離して得たろ液を濃縮して粉沫344mgを得た。このろ液には、ノビレチン159mg(44.2重量%)及びタンゲレチン87mg(22.7重量%)が含まれていた。本法によれば、濃縮液に含まれていたノビレチン及びタンゲレチンを60%以上回収することができた。
シークワーサーの葉589g(湿重量)を秤量し、乾燥機(東京理化器械(株)、WFO-1001SD)を用いて、約80℃で16時間乾燥させ、乾燥葉218gを得た。得られた乾燥葉のうち5gに100mLの約70℃の蒸留水を加えて約70℃の湯浴中に入れ、3時間、加熱抽出した。得られた抽出液を、保留粒子径3μmのろ紙(ADVANTEC社製、No.131)を敷いたブッフナーロートを用いて吸引ろ過し、残渣を得た。
シークワーサーの乾燥葉5gに100mLの約70℃の蒸留水を加えて約70℃の湯浴中に入れ、3時間、加熱抽出した。得られた抽出液を、保留粒子径3μmのろ紙(ADVANTEC社製、No.131)を敷いたブッフナーロートを用いて吸引ろ過し、残渣を得た。
シークワーサーの乾燥葉5gに100mLの約70℃の蒸留水を加えて約70℃の湯浴中に入れ、3時間、加熱抽出した。得られた抽出液を、保留粒子径3μmのろ紙(ADVANTEC社製、No.131)を敷いたブッフナーロートを用いて吸引ろ過し、残渣を得た。
Claims (11)
- 以下の工程(1-1)~(1-3)又は工程(2)と工程(3)及び(4)とを含む、ノビレチン及びタンゲレチン含有物の製造方法。
(1-1)柑橘類を熱水で処理することにより熱水処理物を得る工程
(1-2)前記熱水処理物を乾燥することにより乾燥物を得る工程
(1-3)前記乾燥物をノビレチン及びタンゲレチン可溶性である溶媒で処理することによりノビレチン及びタンゲレチン溶解物を得る工程
(2)柑橘類をノビレチン及びタンゲレチン可溶性である温溶媒で処理することによりノビレチン及びタンゲレチン溶解物を得る工程
(3)前記ノビレチン及びタンゲレチン溶解物を濃縮及び/又は乾燥することにより、ノビレチン及びタンゲレチン濃縮物を得る工程
(4)前記ノビレチン及びタンゲレチン濃縮物を希アルカリで処理することにより、不溶性成分としてノビレチン及びタンゲレチン含有物を得る工程 - 前記工程(1-1)が、柑橘類を50~80℃の温度に維持された熱水で2~4時間処理して熱水処理物を得る工程である、請求項1に記載のノビレチン及びタンゲレチン含有物の製造方法。
- 前記工程(2)が、柑橘類を50~70℃の温度に維持されたノビレチン及びタンゲレチン可溶性である温溶媒で1~8時間処理してノビレチン及びタンゲレチン溶解物を得る工程である、請求項1に記載のノビレチン及びタンゲレチン含有物の製造方法。
- 前記ノビレチン及びタンゲレチン可溶性である溶媒又は前記ノビレチン及びタンゲレチン可溶性である温溶媒が、20~100%(v/v)エタノールである、請求項1に記載のノビレチン及びタンゲレチン含有物の製造方法。
- 前記ノビレチン及びタンゲレチン可溶性である溶媒又は前記ノビレチン及びタンゲレチン可溶性である温溶媒が、20~50%(v/v)エタノールである、請求項1に記載のノビレチン及びタンゲレチン含有物の製造方法。
- 前記工程(4)が、前記ノビレチン及びタンゲレチン濃縮物を1~3%(w/v)のアルカリ水溶液で、室温下にて処理することにより、不溶性成分としてノビレチン及びタンゲレチン含有物を得る工程である、請求項1に記載のノビレチン及びタンゲレチン含有物の製造方法。
- 前記柑橘類は、シークワーサー(Citrus depressa)、ウンシュウミカン(C.unshiu)、タチバナ(C.tachibana)、コウジ(C.leiocarpa)、ギリミカン(C.tardiva)、ジミカン(C.succosa)、キシュウ(C.kinokuni)、コベニミカン(C.erythrosa)、スンキ(C.sunki)、チチュウカイマンダリン(C.deliciosa)、キング(C.nobilis)、ポンカン(C.retuculata)、ダンシータンジェリン(C.tangerina)、ハナユ(C.hanayu)、マンダリンオレンジ(C.reticulata)、サンキ(C.sunki)、コウライタチバナ(C.nippokoreana)、シラヌヒ及び清見からなる群から選ばれる少なくとも1種の植物である、請求項1に記載のノビレチン及びタンゲレチン含有物の製造方法。
- 請求項1~7のいずれか1項に記載された製造方法で製造された、ノビレチン及びタンゲレチン含有物。
- 前記ノビレチン及びタンゲレチン含有物中のノビレチンの含有率が45%(w/v)以上であり、かつ、タンゲレチンの含有率が25%(w/v)以上である、請求項8に記載のノビレチン及びタンゲレチン含有物。
- 前記ノビレチン及びタンゲレチン含有物中のシネフリンの含有率が検出下限値未満である、請求項8に記載のノビレチン及びタンゲレチン含有物。
- ノビレチンの含有率が45%(w/v)以上であり、タンゲレチンの含有率が25%(w/v)以上であり、かつ、シネフリンの含有率が検出下限値未満である、柑橘類由来のノビレチン及びタンゲレチン含有物。
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EP2907395B1 (en) | 2018-12-12 |
EP2907395A4 (en) | 2016-05-25 |
EP2907395A1 (en) | 2015-08-19 |
US20150283196A1 (en) | 2015-10-08 |
US10548938B2 (en) | 2020-02-04 |
KR20150072420A (ko) | 2015-06-29 |
CN104902764A (zh) | 2015-09-09 |
JP5735184B2 (ja) | 2015-06-17 |
JPWO2014057727A1 (ja) | 2016-09-05 |
CN104902764B (zh) | 2017-12-26 |
KR101747125B1 (ko) | 2017-06-14 |
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