WO2022138915A1 - Refined rosmarinic acid-containing composition production method - Google Patents
Refined rosmarinic acid-containing composition production method Download PDFInfo
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- WO2022138915A1 WO2022138915A1 PCT/JP2021/048199 JP2021048199W WO2022138915A1 WO 2022138915 A1 WO2022138915 A1 WO 2022138915A1 JP 2021048199 W JP2021048199 W JP 2021048199W WO 2022138915 A1 WO2022138915 A1 WO 2022138915A1
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- rosmarinic acid
- containing composition
- mass
- acid
- purified
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- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 title claims abstract description 208
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 title claims abstract description 104
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 title claims abstract description 104
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 title claims abstract description 104
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 107
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 71
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- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 claims abstract description 31
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 235000009498 luteolin Nutrition 0.000 claims abstract description 31
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- 238000000746 purification Methods 0.000 claims description 7
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- 239000007864 aqueous solution Substances 0.000 abstract description 32
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- 239000002253 acid Substances 0.000 description 17
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Images
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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
Definitions
- the present invention relates to a method for producing a purified rosmarinic acid-containing composition.
- Lamiaceae plants have been used for food and medicinal purposes since ancient times.
- As a medicinal component of Labiatae plants rosmarinic acid mainly contained in leaves is known, and it has been reported that rosmarinic acid has an anti-allergic action, an anti-inflammatory action and the like (Non-Patent Document 1).
- Patent Document 1 raw or sun-dried pertussis plant after collection is extracted with a lower alcohol having a water content of 10 to 30 vol%, and precipitation occurs by adding water. After concentrating the obtained extract, lower alcohol is added to bring the alcohol concentration to 90 vol% or more, the resulting precipitate is removed to obtain a liquid component, and activated charcoal is further added to remove residual impurities.
- Patent Document 2 A method for producing a perilla extract contained in a high concentration such as (Patent Document 2) has been reported.
- Patent Document 1 International Publication No. 2002/62365
- Patent Document 2 Japanese Patent Application Laid-Open No. 7-187989
- Non-Patent Document 1 Hiroshi Kido, Oreo Science, 2004, 4 (10), p. 409-415
- the present invention is obtained by subjecting a rosmarinic acid-containing composition having a rosmarinic acid content of 7% by mass or more in a solid content, which is obtained through an extraction step of extracting rosmarinic acid from a Labiatae plant, in a 30 to 50 vol% ethanol aqueous solution.
- the present invention relates to a method for producing a purified losmarin acid-containing composition, which comprises a contacting step of contacting with activated charcoal.
- the conventional Labiatae plant extract containing a high concentration of rosmarinic acid has a turbidity in its aqueous solution, and improvement in transparency is required.
- the present inventor investigated the cause of the turbidity of the aqueous solution, and found that it was found to be luteolin mixed in the Labiatae plant extract. That is, when rosmarinic acid was extracted from Labiatae plants, luteolin in Labiatae plants was also extracted, causing turbidity in the aqueous solution. Therefore, the present invention relates to a method for producing a purified rosmarinic acid-containing composition which can be a highly transparent aqueous solution by reducing the amount of luteolin while retaining rosmarinic acid.
- the present inventor contacted a rosmarinic acid-containing composition obtained through an extraction step of extracting rosmarinic acid from a Labiatae plant with activated charcoal in an aqueous ethanol solution having a specific concentration, thereby leaving rosmarinic acid and luteolin. It has been found that the amount can be selectively reduced and the transparency of the rosmarinic acid-containing composition in an aqueous solution can be improved.
- the amount of luteolin that causes turbidity of the aqueous solution can be reduced while the rosmarinic acid remains, so that a purified rosmarinic acid-containing composition having high transparency of the aqueous solution can be obtained.
- the method for producing a purified rosmarinic acid-containing composition of the present invention is obtained through an extraction step of extracting rosmarinic acid from Labiatae plants, and the content of rosmarinic acid in the solid content is 7% by mass or more. It has a contacting step of bringing the material into contact with activated carbon in a 30-50 vol% aqueous ethanol solution.
- the Labiatae plant is not particularly limited as long as it is a plant classified into the Labiatae family (Lamiaceae), but for example, perilla, perilla, rosemary, lavender, salvia, sage, hacka, peppermint, lemon balm, basil, thyme. And so on.
- Labiatae plants can be used.
- plants of the genus Perilla such as red perilla and blue perilla are preferable, and red perilla is more preferable, from the viewpoint of the extraction rate of rosmarinic acid.
- the site of use of Labiatae plants is not particularly limited, and examples thereof include whole plants, leaves, stems, buds, flowers, branches, roots, seeds, and mixtures thereof. Of these, leaves are preferable from the viewpoint of the extraction rate of rosmarinic acid.
- These parts are not particularly limited and can be used as they are or after being crushed, crushed, cut or dried.
- extraction means In the extraction step for extracting rosmarinic acid from Labiatae plants, any means such as solid-liquid extraction, liquid-liquid extraction, immersion, decoction, leaching, steam distillation, reflux extraction, ultrasonic extraction, microwave extraction, and stirring are used. be able to.
- the solvent for extraction either a polar solvent or a non-polar solvent can be used.
- the solvent include, for example, water; monovalent or divalent or polyvalent alcohols; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; chains such as diethyl ether and tetrahydrofuran or Cyclic ethers; Polyethers such as polyethylene glycol; Saturated or unsaturated hydrocarbons such as hexane; Aromatic hydrocarbons such as benzene and toluene; Halogenized hydrocarbons such as dichloromethane, chloroform, dichloroethane, carbon tetrachloride, etc.
- Hydrocarbons pyridines; dimethylsulfoxide; acetonitrile; carbon dioxide, supercritical carbon dioxide; fats and oils, waxes, other oils; and mixtures thereof.
- Preferred examples thereof include water, alcohols and aqueous solutions thereof, and examples of alcohols include methanol, ethanol, 1,3-butylene glycol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol and t-butanol.
- Etc. preferably water, ethanol, an aqueous ethanol solution, and more preferably water.
- the amount of the solvent used in the extraction and the extraction conditions are not particularly limited as long as they can sufficiently extract the rosmarinic acid, and can be appropriately adjusted.
- the extraction time is preferably 30 minutes or more, more preferably 1 hour or more, and preferably 10 hours or less, more preferably 2 hours or less.
- the extraction time is preferably 30 minutes to 10 hours, more preferably 1 hour to 2 hours.
- Extraction can be carried out at room temperature or under heating conditions, and the extraction temperature under heating conditions is preferably 20 ° C. or higher, preferably 50 ° C. or higher, more preferably 80 ° C. or higher, and preferably 100 ° C. or lower. be.
- the extraction temperature under heating conditions is preferably 20 to 100 ° C, more preferably 50 to 100 ° C, and even more preferably 80 to 100 ° C.
- extraction is performed for a long time at low temperature and for a short time at high temperature.
- the extraction step can be performed once or multiple times.
- the Labiatae plant extract obtained in the extraction step may be used as it is as a rosmarinic acid-containing composition, but it is preferable to carry out a purification step of the extract from the viewpoint of increasing the concentration of rosmarinic acid.
- the purification step include an operation of concentrating the extract, adding ethanol or an aqueous ethanol solution, and then removing the precipitate, a resin adsorption operation, and the like.
- concentration of the extract ordinary means such as atmospheric pressure concentration, vacuum concentration concentration, and membrane concentration can be used.
- the form of the rosmarinic acid-containing composition is not particularly limited and may be solid, semi-solid or liquid.
- the rosmarinic acid-containing composition has a rosmarinic acid content of 7% by mass or more in the solid content.
- the content of rosmarinic acid in the solid content is preferably 10% by mass or more, more preferably 15% by mass or more, from the viewpoint of easily enjoying the effects of the present invention.
- the upper limit is not particularly limited, but is preferably 30% by mass or less, more preferably 20% by mass or less, from the viewpoint of suppressing costs related to the extraction step and the purification step of the extract.
- the content of rosmarinic acid in the solid content is preferably 7 to 30% by mass, more preferably 10 to 20% by mass, and further preferably 15 to 20% by mass.
- the term "solid content” as used herein refers to the residue obtained by concentrating a sample under reduced pressure with a rotary evaporator, then adding water, freeze-drying, and removing volatile substances.
- the rosmarinic acid-containing composition obtained through the extraction step contains luteolin.
- the content of luteolin in the solid content of the rosmarinic acid-containing composition is preferably 500 to 1000 ppm (mass million) from the viewpoint that the effects of the present invention can be easily enjoyed and the costs related to the extraction step and the purification step of the extract can be suppressed. It is a fraction), and more preferably 700 to 1000 ppm.
- the mass ratio of the content of rosmarin acid to the content of luteolin in the composition containing rosmarin acid [content of rosmarin acid / content of luteolin] is easy to enjoy the effects of the present invention, and the extraction step and purification of the extract can be easily enjoyed. From the viewpoint of suppressing the cost related to the process, it is preferably 1000 or more, more preferably 5000 or more, and further preferably 10000 or more.
- examples of the raw material derived from the activated carbon to be brought into contact with the rosmarinic acid-containing composition include ogako, coal, coconut shell and the like. Of these, coconut shell activated carbon derived from coconut shell is preferable from the viewpoint of reducing luteolin.
- activated carbon activated by gas such as steam or chemicals is preferably used.
- the shape of the activated carbon is not particularly limited, and examples thereof include powder, granular, and fibrous.
- a commercially available product such as Kuraray Coal GW (manufactured by Kuraray Co., Ltd.) can be used.
- the amount of activated carbon used is preferably 20% by mass or more, more preferably 25% by mass or more, and further, from the viewpoint of increasing the recovery rate of rosmarin acid and reducing luteolin, with respect to the solid content mass of the rosmarin acid-containing composition. It is preferably 30% by mass or more, preferably 100% by mass or less, and more preferably 70% by mass or less.
- the amount of activated carbon used is preferably 20 to 100% by mass, more preferably 25 to 70% by mass, and even more preferably 30 to 70% by mass with respect to the solid content mass of the rosmarinic acid-containing composition.
- the rosmarinic acid-containing composition is contacted with activated carbon in an aqueous ethanol solution.
- the ethanol concentration of the aqueous ethanol solution at the time of contact with activated carbon is 30 to 50 vol% from the viewpoint of increasing the recovery rate of rosmarin acid and reducing luteolin.
- the concentration of the ethanol aqueous solution can be adjusted, for example, by adding / mixing ethanol and water to the rosmarinic acid-containing composition so that the ethanol concentration in the ethanol aqueous solution is within the above range, or to the rosmarinic acid-containing composition. Then, after adding and mixing ethanol, a method of adding water to adjust the ethanol concentration within the above range can be mentioned.
- the amount of the aqueous ethanol solution is preferably 5 times by mass or more, more preferably 10 times by mass or more, and preferably 100 times by mass with respect to the solid content of the rosmarinic acid-containing composition. Below, it is more preferably 50 times by mass or less.
- the amount of the aqueous ethanol solution used is preferably 5 to 100 times by mass, more preferably 10 to 50 times by mass, based on the solid content of the rosmarinic acid-containing composition.
- Contact means As a means for bringing the rosmarinic acid-containing composition into contact with activated carbon, the activated carbon is added to an aqueous ethanol solution, stirred and adsorbed, and then the activated carbon is recovered by a filtration operation. Examples include continuous type.
- the contact temperature is preferably 10 ° C. or higher, and preferably 50 ° C. or lower, from the viewpoint of reducing luteolin.
- the contact time can be appropriately selected depending on the contact means and scale, but for example, from the viewpoint of reducing luteolin, it is preferably 4 hours or more, more preferably 10 hours or more.
- the purified rosmarinic acid-containing composition of the present invention can be obtained by recovering the treated liquid by a solid-liquid separation operation such as centrifugation or filtration after contact with activated carbon.
- the form of the purified rosmarinic acid-containing composition is not particularly limited and may be solid, semi-solid or liquid, but from the viewpoint of increasing the solid content concentration, the treatment liquid recovered above can be concentrated under normal pressure, concentrated under reduced pressure, or membrane. It is preferable to concentrate by using a usual means such as concentration. After concentration, it may be dried by ordinary means such as spray drying and freeze drying.
- the recovery rate of rosmarin acid from the rosmarin acid-containing composition can be as high as 80% or more, more preferably 90% or more.
- the purity of rosmarinic acid in the solid content is preferably 10% by mass or more, more preferably 14% by mass or more.
- the aqueous solution of the purified rosmarinic acid-containing composition of the present invention has high transparency.
- the content of luteolin in the solid content of the purified rosmarinic acid-containing composition is preferably 150 ppmm or less, more preferably 110 ppm or less, still more preferably 100 ppm or less, from the viewpoint of the transparency of the aqueous solution.
- the mass ratio of the content of rosmarin acid to the content of luteolin in the purified rosmarin acid-containing composition [the content of rosmarin acid / the content of luteolin] is preferably 1000 or more, more preferably 1000 or more, from the viewpoint of the transparency of the aqueous solution.
- the absorbance of the purified rosmarinic acid-containing composition having a solid content of 1% by mass at a wavelength of 680 nm measured by the method described in Examples below is preferably 0.15 or less, more preferably 0.10 or less. be.
- the present invention further discloses the following production method and composition.
- a rosmarinic acid-containing composition obtained through an extraction step of extracting rosmarinic acid from a Labiatae plant and having a rosmarinic acid content of 7% by mass or more in a solid content is prepared in a 30 to 50 vol% aqueous ethanol solution.
- a method for producing a purified rosmarinic acid-containing composition which comprises a contacting step of contacting with activated carbon.
- ⁇ 2> Production of the purified rosmarinic acid-containing composition according to ⁇ 1>, wherein the Labiatae plant is preferably a plant belonging to the Labiatae family, more preferably red perilla or blue perilla, and further preferably red perilla. Method.
- the site of use of Labiatae plants is preferably whole plants, leaves, stems, buds, flowers, branches, roots, seeds, and mixtures thereof, and more preferably leaves ⁇ 1> or ⁇ 2>.
- the method for producing a purified rosmarinic acid-containing composition according to the above method is preferably a plant belonging to the Labiatae family, more preferably red perilla or blue perilla, and further preferably red perilla.
- the site of use of Labiatae plants is preferably whole plants, leaves, stems, buds, flowers, branches, roots, seeds, and mixtures thereof, and more preferably leaves ⁇ 1> or ⁇ 2>.
- the content of rosmarinic acid in the solid content of the rosmarinic acid-containing composition is 7% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, and preferably. It is 30% by mass or less, more preferably 20% by mass or less, preferably 7 to 30% by mass, more preferably 10 to 20% by mass, still more preferably 15 to 20% by mass ⁇ 1> to.
- the method for producing a purified rosmarinic acid-containing composition according to any one of ⁇ 3>.
- the rosmarinic acid-containing composition contains luteolin, and the mass ratio of the rosumelic acid content to the luteolin content in the rosmarin acid-containing composition is preferably 1000 or more, more preferably 5000 or more, still more preferably 10,000 or more.
- the content of luteolin in the solid content of the rosmarinic acid-containing composition is preferably 500 ppm (parts per million by mass) or more, more preferably 700 ppm or more, and preferably 1000 ppm or less ⁇ 5>.
- the amount of the activated charcoal used is preferably 20% by mass or more, more preferably 25% by mass or more, still more preferably 30% by mass or more, and more preferably 30% by mass or more, based on the solid content mass of the rosmarinic acid-containing composition. Is 100% by mass or less, more preferably 70% by mass or less, preferably 20 to 100% by mass, more preferably 25 to 70% by mass, still more preferably 30 to 70% by mass ⁇ 1> to ⁇ . 6> The method for producing a purified rosmarinic acid-containing composition according to any one of 6.
- ⁇ 8> The method for producing a purified rosmarinic acid-containing composition according to any one of ⁇ 1> to ⁇ 7>, wherein the activated carbon is preferably coconut shell activated carbon derived from coconut shell, and more preferably granular coconut shell activated carbon. .. ⁇ 9>
- the amount of the ethanol aqueous solution used is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 100% by mass or less, more preferably, with respect to the solid content of the rosmarinic acid-containing composition.
- the method for producing a purified rosmarinic acid-containing composition according to any one of ⁇ 1> to ⁇ 8>, wherein is 50 times by mass or less, preferably 5 to 100 times by mass, and more preferably 10 to 50 times by mass. .. ⁇ 10>
- the purified rosmarin according to any one of ⁇ 1> to ⁇ 9> which comprises a purification step of concentrating the extract and then adding ethanol or an aqueous ethanol solution to remove the precipitate formed after the extraction step.
- a method for producing an acid-containing composition which comprises a purification step of concentrating the extract and then adding ethanol or an aqueous ethanol solution to remove the precipitate formed after the extraction step.
- Recovery rate of rosmarinic acid (weight of extract powder frozen and dried after activated carbon treatment x purity of extract powder rosmarinic acid after treated with activated carbon) ⁇ (weight of lyophilized extract powder before activated carbon treatment x extract powder rosmarinic acid before activated carbon treatment) Purity) x 100 (%)
- Examples and Comparative Examples 1 Add 2200 kg of hot water at 80 ° C and 73.3 kg of 6M sodium hydroxide aqueous solution to 200 kg of red shiso KU (manufactured by Kodama Foods Co., Ltd.), which is a dried leaf of red perilla soaked in citric acid, adjust the pH to 4.5, and then 1 at 90 ° C. Time hot water extraction. The extract is filtered and concentrated to 225 kg, then 77 kg of 95 vol% ethanol is added to prepare an 82 vol% ethanol aqueous solution, and the mixture is stirred at 30 ° C. for 1 hour to remove the resulting precipitate. The red perilla extract powder obtained by drying was used.
- red shiso KU manufactured by Kodama Foods Co., Ltd.
- the amount of rosmarinic acid in the solid content of the red perilla extract powder was 17.1% by mass, and the amount of luteolin was 918.4 ppm (parts by mass).
- FIG. 1 shows the appearance of the aqueous solutions of Comparative Example 7, Comparative Example 8 and Example 1 before the treatment.
- luteolin can be selectively reduced while suppressing the loss of rosmarinic acid in the activated carbon treatment and recovering rosmarinic acid in good yield, and the aqueous solution is transparent. It was confirmed that the sex could be improved.
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Abstract
Provided is a refined rosmarinic acid-containing composition production method that enables obtaining of a highly transparent aqueous solution by reducing the amount of luteolin while causing rosmarinic acid to remain. This refined rosmarinic acid-containing composition production method comprises a contact step for bringing, into contact with activated carbon in a 30-50 vol% ethanol solution, a rosmarinic acid-containing composition which is obtained through an extraction step for extracting rosmarinic acid from a plant belonging to the family Lamiaceae and in which the contained amount of rosmarinic acid in solid content is 7 mass% or more.
Description
本発明は、精製ロズマリン酸含有組成物の製造方法に関する。
The present invention relates to a method for producing a purified rosmarinic acid-containing composition.
シソ科(Lamiaceae)の植物は古くから食用・薬用に用いられてきた。シソ科植物の薬効成分としては主に葉に含まれるロズマリン酸が知られ、ロズマリン酸は、抗アレルギー作用や抗炎症作用等を有することが報告されている(非特許文献1)。
Lamiaceae plants have been used for food and medicinal purposes since ancient times. As a medicinal component of Labiatae plants, rosmarinic acid mainly contained in leaves is known, and it has been reported that rosmarinic acid has an anti-allergic action, an anti-inflammatory action and the like (Non-Patent Document 1).
シソ科植物からロズマリン酸を含む抽出物を製造する方法としては、例えば、赤シソの生葉全葉を、pH0.5~4.0の酸性条件下で、水にて50~93℃にて抽出するロズマリン酸含有シソ科植物抽出物の製造法(特許文献1)、採取後の生或いは天日乾燥したシソ科植物を含水率10~30vol%の低級アルコールで抽出し、水を加えて生じる沈殿を除去し、得られた抽出液を濃縮後、低級アルコールを加えてアルコール濃度90vol%以上とし、生じる沈殿を除去して液状成分を得、さらに活性炭を加えて残存する不純物を除去する、ロズマリン酸等の高濃度に含有するシソ抽出液の製造方法(特許文献2)が報告されている。
As a method for producing an extract containing rosmarinic acid from a perilla family plant, for example, whole leaves of red perilla are extracted with water at 50 to 93 ° C. under acidic conditions of pH 0.5 to 4.0. Method for producing rosmarinic acid-containing perilla plant extract (Patent Document 1), raw or sun-dried pertussis plant after collection is extracted with a lower alcohol having a water content of 10 to 30 vol%, and precipitation occurs by adding water. After concentrating the obtained extract, lower alcohol is added to bring the alcohol concentration to 90 vol% or more, the resulting precipitate is removed to obtain a liquid component, and activated charcoal is further added to remove residual impurities. A method for producing a perilla extract contained in a high concentration such as (Patent Document 2) has been reported.
(特許文献1)国際公開第2002/62365号
(特許文献2)特開平7-187989号公報 (Patent Document 1) International Publication No. 2002/62365 (Patent Document 2) Japanese Patent Application Laid-Open No. 7-187989
(特許文献2)特開平7-187989号公報 (Patent Document 1) International Publication No. 2002/62365 (Patent Document 2) Japanese Patent Application Laid-Open No. 7-187989
(非特許文献1)城戸浩胤, オレオサイエンス, 2004年、4(10), p.409-415
(Non-Patent Document 1) Hiroshi Kido, Oreo Science, 2004, 4 (10), p. 409-415
本発明は、シソ科植物からロズマリン酸を抽出する抽出工程を経て得られ、固形分中のロズマリン酸の含有量が7質量%以上であるロズマリン酸含有組成物を、30~50vol%エタノール水溶液中で活性炭と接触させる接触工程を含む、精製ロズマリン酸含有組成物の製造方法に係るものである。
The present invention is obtained by subjecting a rosmarinic acid-containing composition having a rosmarinic acid content of 7% by mass or more in a solid content, which is obtained through an extraction step of extracting rosmarinic acid from a Labiatae plant, in a 30 to 50 vol% ethanol aqueous solution. The present invention relates to a method for producing a purified losmarin acid-containing composition, which comprises a contacting step of contacting with activated charcoal.
しかしながら、従来のロズマリン酸を高濃度に含むシソ科植物抽出物は、その水溶液に濁りがあり、透明性の改善が求められた。
本発明者は、水溶液の濁りの原因について検討したところ、シソ科植物抽出物に混在するルテオリンにあることを見出した。すなわち、シソ科植物からロズマリン酸を抽出する際にシソ科植物中のルテオリンも一緒に抽出され、水溶液に濁りを生じさせていた。
従って、本発明は、ロズマリン酸を残存させながらルテオリン量を低減することにより透明性の高い水溶液となり得る精製ロズマリン酸含有組成物を製造する方法を提供することに関する。 However, the conventional Labiatae plant extract containing a high concentration of rosmarinic acid has a turbidity in its aqueous solution, and improvement in transparency is required.
The present inventor investigated the cause of the turbidity of the aqueous solution, and found that it was found to be luteolin mixed in the Labiatae plant extract. That is, when rosmarinic acid was extracted from Labiatae plants, luteolin in Labiatae plants was also extracted, causing turbidity in the aqueous solution.
Therefore, the present invention relates to a method for producing a purified rosmarinic acid-containing composition which can be a highly transparent aqueous solution by reducing the amount of luteolin while retaining rosmarinic acid.
本発明者は、水溶液の濁りの原因について検討したところ、シソ科植物抽出物に混在するルテオリンにあることを見出した。すなわち、シソ科植物からロズマリン酸を抽出する際にシソ科植物中のルテオリンも一緒に抽出され、水溶液に濁りを生じさせていた。
従って、本発明は、ロズマリン酸を残存させながらルテオリン量を低減することにより透明性の高い水溶液となり得る精製ロズマリン酸含有組成物を製造する方法を提供することに関する。 However, the conventional Labiatae plant extract containing a high concentration of rosmarinic acid has a turbidity in its aqueous solution, and improvement in transparency is required.
The present inventor investigated the cause of the turbidity of the aqueous solution, and found that it was found to be luteolin mixed in the Labiatae plant extract. That is, when rosmarinic acid was extracted from Labiatae plants, luteolin in Labiatae plants was also extracted, causing turbidity in the aqueous solution.
Therefore, the present invention relates to a method for producing a purified rosmarinic acid-containing composition which can be a highly transparent aqueous solution by reducing the amount of luteolin while retaining rosmarinic acid.
本発明者は、シソ科植物からロズマリン酸を抽出する抽出工程を経て得られたロズマリン酸含有組成物を特定の濃度のエタノール水溶液中で活性炭と接触させることで、ロズマリン酸を残存させながら、ルテオリン量を選択的に低減することができ、ロズマリン酸含有組成物の水溶液における透明性を改善できることを見出した。
The present inventor contacted a rosmarinic acid-containing composition obtained through an extraction step of extracting rosmarinic acid from a Labiatae plant with activated charcoal in an aqueous ethanol solution having a specific concentration, thereby leaving rosmarinic acid and luteolin. It has been found that the amount can be selectively reduced and the transparency of the rosmarinic acid-containing composition in an aqueous solution can be improved.
本発明によれば、ロズマリン酸を残存させつつも、水溶液の濁りの原因となるルテオリン量を低減することができるので、水溶液の透明性が高い精製ロズマリン酸含有組成物を得ることができる。
According to the present invention, the amount of luteolin that causes turbidity of the aqueous solution can be reduced while the rosmarinic acid remains, so that a purified rosmarinic acid-containing composition having high transparency of the aqueous solution can be obtained.
本発明の精製ロズマリン酸含有組成物の製造方法は、シソ科植物からロズマリン酸を抽出する抽出工程を経て得られ、固形分中のロズマリン酸の含有量が7質量%以上であるロズマリン酸含有組成物を、30~50vol%エタノール水溶液中で活性炭と接触させる接触工程を有する。
The method for producing a purified rosmarinic acid-containing composition of the present invention is obtained through an extraction step of extracting rosmarinic acid from Labiatae plants, and the content of rosmarinic acid in the solid content is 7% by mass or more. It has a contacting step of bringing the material into contact with activated carbon in a 30-50 vol% aqueous ethanol solution.
(シソ科植物)
本発明においてシソ科植物は、シソ科(Lamiaceae)に分類される植物であれば特に限定されないが、例えば、シソ、エゴマ、ローズマリー、ラベンダー、サルビア、セージ、ハッカ、ペパーミント、レモンバーム、バジル、タイム等が挙げられる。シソ科植物は、1種又は2種以上用いることができる。なかでも、ロズマリン酸の抽出率の観点から、赤シソ、青シソ等のシソ属(Perill)の植物が好ましく、赤シソがより好ましい。
シソ科植物の使用部位としては、特に限定されず、例えば、全草、葉、茎、芽、花、枝、根、種子等、並びにこれらの混合物が挙げられる。なかでも、ロズマリン酸の抽出率の観点から、葉が好ましい。これらの部位は、特に限定されず、そのまま又は粉砕、破砕、切断若しくは乾燥して用いることができる。 (Lamiaceae)
In the present invention, the Labiatae plant is not particularly limited as long as it is a plant classified into the Labiatae family (Lamiaceae), but for example, perilla, perilla, rosemary, lavender, salvia, sage, hacka, peppermint, lemon balm, basil, thyme. And so on. One or more kinds of Labiatae plants can be used. Among them, plants of the genus Perilla such as red perilla and blue perilla are preferable, and red perilla is more preferable, from the viewpoint of the extraction rate of rosmarinic acid.
The site of use of Labiatae plants is not particularly limited, and examples thereof include whole plants, leaves, stems, buds, flowers, branches, roots, seeds, and mixtures thereof. Of these, leaves are preferable from the viewpoint of the extraction rate of rosmarinic acid. These parts are not particularly limited and can be used as they are or after being crushed, crushed, cut or dried.
本発明においてシソ科植物は、シソ科(Lamiaceae)に分類される植物であれば特に限定されないが、例えば、シソ、エゴマ、ローズマリー、ラベンダー、サルビア、セージ、ハッカ、ペパーミント、レモンバーム、バジル、タイム等が挙げられる。シソ科植物は、1種又は2種以上用いることができる。なかでも、ロズマリン酸の抽出率の観点から、赤シソ、青シソ等のシソ属(Perill)の植物が好ましく、赤シソがより好ましい。
シソ科植物の使用部位としては、特に限定されず、例えば、全草、葉、茎、芽、花、枝、根、種子等、並びにこれらの混合物が挙げられる。なかでも、ロズマリン酸の抽出率の観点から、葉が好ましい。これらの部位は、特に限定されず、そのまま又は粉砕、破砕、切断若しくは乾燥して用いることができる。 (Lamiaceae)
In the present invention, the Labiatae plant is not particularly limited as long as it is a plant classified into the Labiatae family (Lamiaceae), but for example, perilla, perilla, rosemary, lavender, salvia, sage, hacka, peppermint, lemon balm, basil, thyme. And so on. One or more kinds of Labiatae plants can be used. Among them, plants of the genus Perilla such as red perilla and blue perilla are preferable, and red perilla is more preferable, from the viewpoint of the extraction rate of rosmarinic acid.
The site of use of Labiatae plants is not particularly limited, and examples thereof include whole plants, leaves, stems, buds, flowers, branches, roots, seeds, and mixtures thereof. Of these, leaves are preferable from the viewpoint of the extraction rate of rosmarinic acid. These parts are not particularly limited and can be used as they are or after being crushed, crushed, cut or dried.
(抽出手段)
シソ科植物からロズマリン酸を抽出する抽出工程では、固液抽出、液液抽出、浸漬、煎出、浸出、水蒸気蒸留、還流抽出、超音波抽出、マイクロ波抽出、撹拌等の任意の手段を用いることができる。
抽出の為の溶媒には、極性溶媒、非極性溶媒のいずれをも使用することができる。溶媒の具体例としては、例えば、水;1価、2価又は多価のアルコール類;アセトン、メチルエチルケトン等のケトン類;酢酸メチル、酢酸エチル等のエステル類;ジエチルエーテル、テトラヒドロフラン等の鎖状又は環状のエーテル類;ポリエチレングリコール等のポリエーテル類;ヘキサン等の飽和又は不飽和の炭化水素類;ベンゼン、トルエン等の芳香族炭化水素類;ジクロロメタン、クロロホルム、ジクロロエタン、四塩化炭素等のハロゲン化炭化水素類;ピリジン類;ジメチルスルホキシド;アセトニトリル;二酸化炭素、超臨界二酸化炭素;油脂、ワックス、その他のオイル類;並びにこれらの混合物が挙げられる。好適には、水、アルコール類及びその水溶液が挙げられ、アルコール類としてはメタノール、エタノール、1,3-ブチレングリコール、n-プロパノール、イソプロパノール、n-ブタノール、イソブタノール、sec-ブタノール、t-ブタノール等が挙げられ、好ましくは水、エタノール、エタノール水溶液であり、より好ましくは水である。
抽出における溶媒の使用量、抽出条件は、十分なロズマリン酸の抽出が行える条件であれば特に限定されず、適宜調整することができる。
例えば、抽出時間は、好ましくは30分以上、より好ましくは1時間以上であり、また、好ましくは10時間以下、より好ましくは2時間以下である。そして、抽出時間は、好ましくは30分~10時間、より好ましくは1時間~2時間である。
抽出は室温又は加熱条件下で行うことができ、加熱条件下での抽出温度は20℃以上が好ましく、好ましくは50℃以上、より好ましくは80℃以上であり、また、好ましくは100℃以下である。そして、抽出温度は、加熱条件下での抽出温度は、好ましくは20~100℃、より好ましくは50~100℃、更に好ましくは80~100℃である。通常、低温なら長時間、高温なら短時間の抽出を行う。抽出工程は、1回又は複数回行うことができる。 (Extraction means)
In the extraction step for extracting rosmarinic acid from Labiatae plants, any means such as solid-liquid extraction, liquid-liquid extraction, immersion, decoction, leaching, steam distillation, reflux extraction, ultrasonic extraction, microwave extraction, and stirring are used. be able to.
As the solvent for extraction, either a polar solvent or a non-polar solvent can be used. Specific examples of the solvent include, for example, water; monovalent or divalent or polyvalent alcohols; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; chains such as diethyl ether and tetrahydrofuran or Cyclic ethers; Polyethers such as polyethylene glycol; Saturated or unsaturated hydrocarbons such as hexane; Aromatic hydrocarbons such as benzene and toluene; Halogenized hydrocarbons such as dichloromethane, chloroform, dichloroethane, carbon tetrachloride, etc. Hydrocarbons; pyridines; dimethylsulfoxide; acetonitrile; carbon dioxide, supercritical carbon dioxide; fats and oils, waxes, other oils; and mixtures thereof. Preferred examples thereof include water, alcohols and aqueous solutions thereof, and examples of alcohols include methanol, ethanol, 1,3-butylene glycol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol and t-butanol. Etc., preferably water, ethanol, an aqueous ethanol solution, and more preferably water.
The amount of the solvent used in the extraction and the extraction conditions are not particularly limited as long as they can sufficiently extract the rosmarinic acid, and can be appropriately adjusted.
For example, the extraction time is preferably 30 minutes or more, more preferably 1 hour or more, and preferably 10 hours or less, more preferably 2 hours or less. The extraction time is preferably 30 minutes to 10 hours, more preferably 1 hour to 2 hours.
Extraction can be carried out at room temperature or under heating conditions, and the extraction temperature under heating conditions is preferably 20 ° C. or higher, preferably 50 ° C. or higher, more preferably 80 ° C. or higher, and preferably 100 ° C. or lower. be. The extraction temperature under heating conditions is preferably 20 to 100 ° C, more preferably 50 to 100 ° C, and even more preferably 80 to 100 ° C. Usually, extraction is performed for a long time at low temperature and for a short time at high temperature. The extraction step can be performed once or multiple times.
シソ科植物からロズマリン酸を抽出する抽出工程では、固液抽出、液液抽出、浸漬、煎出、浸出、水蒸気蒸留、還流抽出、超音波抽出、マイクロ波抽出、撹拌等の任意の手段を用いることができる。
抽出の為の溶媒には、極性溶媒、非極性溶媒のいずれをも使用することができる。溶媒の具体例としては、例えば、水;1価、2価又は多価のアルコール類;アセトン、メチルエチルケトン等のケトン類;酢酸メチル、酢酸エチル等のエステル類;ジエチルエーテル、テトラヒドロフラン等の鎖状又は環状のエーテル類;ポリエチレングリコール等のポリエーテル類;ヘキサン等の飽和又は不飽和の炭化水素類;ベンゼン、トルエン等の芳香族炭化水素類;ジクロロメタン、クロロホルム、ジクロロエタン、四塩化炭素等のハロゲン化炭化水素類;ピリジン類;ジメチルスルホキシド;アセトニトリル;二酸化炭素、超臨界二酸化炭素;油脂、ワックス、その他のオイル類;並びにこれらの混合物が挙げられる。好適には、水、アルコール類及びその水溶液が挙げられ、アルコール類としてはメタノール、エタノール、1,3-ブチレングリコール、n-プロパノール、イソプロパノール、n-ブタノール、イソブタノール、sec-ブタノール、t-ブタノール等が挙げられ、好ましくは水、エタノール、エタノール水溶液であり、より好ましくは水である。
抽出における溶媒の使用量、抽出条件は、十分なロズマリン酸の抽出が行える条件であれば特に限定されず、適宜調整することができる。
例えば、抽出時間は、好ましくは30分以上、より好ましくは1時間以上であり、また、好ましくは10時間以下、より好ましくは2時間以下である。そして、抽出時間は、好ましくは30分~10時間、より好ましくは1時間~2時間である。
抽出は室温又は加熱条件下で行うことができ、加熱条件下での抽出温度は20℃以上が好ましく、好ましくは50℃以上、より好ましくは80℃以上であり、また、好ましくは100℃以下である。そして、抽出温度は、加熱条件下での抽出温度は、好ましくは20~100℃、より好ましくは50~100℃、更に好ましくは80~100℃である。通常、低温なら長時間、高温なら短時間の抽出を行う。抽出工程は、1回又は複数回行うことができる。 (Extraction means)
In the extraction step for extracting rosmarinic acid from Labiatae plants, any means such as solid-liquid extraction, liquid-liquid extraction, immersion, decoction, leaching, steam distillation, reflux extraction, ultrasonic extraction, microwave extraction, and stirring are used. be able to.
As the solvent for extraction, either a polar solvent or a non-polar solvent can be used. Specific examples of the solvent include, for example, water; monovalent or divalent or polyvalent alcohols; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; chains such as diethyl ether and tetrahydrofuran or Cyclic ethers; Polyethers such as polyethylene glycol; Saturated or unsaturated hydrocarbons such as hexane; Aromatic hydrocarbons such as benzene and toluene; Halogenized hydrocarbons such as dichloromethane, chloroform, dichloroethane, carbon tetrachloride, etc. Hydrocarbons; pyridines; dimethylsulfoxide; acetonitrile; carbon dioxide, supercritical carbon dioxide; fats and oils, waxes, other oils; and mixtures thereof. Preferred examples thereof include water, alcohols and aqueous solutions thereof, and examples of alcohols include methanol, ethanol, 1,3-butylene glycol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol and t-butanol. Etc., preferably water, ethanol, an aqueous ethanol solution, and more preferably water.
The amount of the solvent used in the extraction and the extraction conditions are not particularly limited as long as they can sufficiently extract the rosmarinic acid, and can be appropriately adjusted.
For example, the extraction time is preferably 30 minutes or more, more preferably 1 hour or more, and preferably 10 hours or less, more preferably 2 hours or less. The extraction time is preferably 30 minutes to 10 hours, more preferably 1 hour to 2 hours.
Extraction can be carried out at room temperature or under heating conditions, and the extraction temperature under heating conditions is preferably 20 ° C. or higher, preferably 50 ° C. or higher, more preferably 80 ° C. or higher, and preferably 100 ° C. or lower. be. The extraction temperature under heating conditions is preferably 20 to 100 ° C, more preferably 50 to 100 ° C, and even more preferably 80 to 100 ° C. Usually, extraction is performed for a long time at low temperature and for a short time at high temperature. The extraction step can be performed once or multiple times.
(ロズマリン酸含有組成物)
抽出工程により得られたシソ科植物の抽出液はそのままロズマリン酸含有組成物として使用してもよいが、ロズマリン酸の濃度を高める観点から、抽出液の精製工程を行うことが好ましい。
精製工程としては、例えば、抽出液を濃縮した後、エタノール又はエタノール水溶液を添加し、次いで沈殿物を除去する操作、樹脂吸着操作等が挙げられる。抽出液の濃縮は、常圧濃縮、減圧濃縮、膜濃縮等の通常の手段を用いることができる。
ロズマリン酸含有組成物の形態は、特に限定されず、固形、半固形又は液状を問わない。 (Rosmarinic acid-containing composition)
The Labiatae plant extract obtained in the extraction step may be used as it is as a rosmarinic acid-containing composition, but it is preferable to carry out a purification step of the extract from the viewpoint of increasing the concentration of rosmarinic acid.
Examples of the purification step include an operation of concentrating the extract, adding ethanol or an aqueous ethanol solution, and then removing the precipitate, a resin adsorption operation, and the like. For the concentration of the extract, ordinary means such as atmospheric pressure concentration, vacuum concentration concentration, and membrane concentration can be used.
The form of the rosmarinic acid-containing composition is not particularly limited and may be solid, semi-solid or liquid.
抽出工程により得られたシソ科植物の抽出液はそのままロズマリン酸含有組成物として使用してもよいが、ロズマリン酸の濃度を高める観点から、抽出液の精製工程を行うことが好ましい。
精製工程としては、例えば、抽出液を濃縮した後、エタノール又はエタノール水溶液を添加し、次いで沈殿物を除去する操作、樹脂吸着操作等が挙げられる。抽出液の濃縮は、常圧濃縮、減圧濃縮、膜濃縮等の通常の手段を用いることができる。
ロズマリン酸含有組成物の形態は、特に限定されず、固形、半固形又は液状を問わない。 (Rosmarinic acid-containing composition)
The Labiatae plant extract obtained in the extraction step may be used as it is as a rosmarinic acid-containing composition, but it is preferable to carry out a purification step of the extract from the viewpoint of increasing the concentration of rosmarinic acid.
Examples of the purification step include an operation of concentrating the extract, adding ethanol or an aqueous ethanol solution, and then removing the precipitate, a resin adsorption operation, and the like. For the concentration of the extract, ordinary means such as atmospheric pressure concentration, vacuum concentration concentration, and membrane concentration can be used.
The form of the rosmarinic acid-containing composition is not particularly limited and may be solid, semi-solid or liquid.
本発明において、ロズマリン酸含有組成物は、固形分中のロズマリン酸の含有量が7質量%以上である。固形分中のロズマリン酸の含有量は、本発明の効果を享受し易い点から、好ましくは10質量%以上であり、より好ましくは15質量%以上である。上限値は特に限定されないが、抽出工程及び抽出液の精製工程に係るコストを抑える観点から、好ましくは30質量%以下であり、より好ましくは20質量%以下である。そして、固形分中のロズマリン酸の含有量は、好ましくは7~30質量%、より好ましくは10~20質量%、さらに好ましくは15~20質量%である。
ここで、本明細書において「固形分」は、試料をロータリーエバポレータで減圧濃縮した後、加水、凍結乾燥して揮発物質を除いた残分をいう。 In the present invention, the rosmarinic acid-containing composition has a rosmarinic acid content of 7% by mass or more in the solid content. The content of rosmarinic acid in the solid content is preferably 10% by mass or more, more preferably 15% by mass or more, from the viewpoint of easily enjoying the effects of the present invention. The upper limit is not particularly limited, but is preferably 30% by mass or less, more preferably 20% by mass or less, from the viewpoint of suppressing costs related to the extraction step and the purification step of the extract. The content of rosmarinic acid in the solid content is preferably 7 to 30% by mass, more preferably 10 to 20% by mass, and further preferably 15 to 20% by mass.
Here, the term "solid content" as used herein refers to the residue obtained by concentrating a sample under reduced pressure with a rotary evaporator, then adding water, freeze-drying, and removing volatile substances.
ここで、本明細書において「固形分」は、試料をロータリーエバポレータで減圧濃縮した後、加水、凍結乾燥して揮発物質を除いた残分をいう。 In the present invention, the rosmarinic acid-containing composition has a rosmarinic acid content of 7% by mass or more in the solid content. The content of rosmarinic acid in the solid content is preferably 10% by mass or more, more preferably 15% by mass or more, from the viewpoint of easily enjoying the effects of the present invention. The upper limit is not particularly limited, but is preferably 30% by mass or less, more preferably 20% by mass or less, from the viewpoint of suppressing costs related to the extraction step and the purification step of the extract. The content of rosmarinic acid in the solid content is preferably 7 to 30% by mass, more preferably 10 to 20% by mass, and further preferably 15 to 20% by mass.
Here, the term "solid content" as used herein refers to the residue obtained by concentrating a sample under reduced pressure with a rotary evaporator, then adding water, freeze-drying, and removing volatile substances.
シソ科植物からロズマリン酸を抽出する抽出工程ではシソ科植物中のルテオリンも一緒に抽出されるため、抽出工程を経て得られるロズマリン酸含有組成物はルテオリンを含有する。
ロズマリン酸含有組成物の固形分中のルテオリンの含有量は、本発明の効果を享受しやすく、抽出工程及び抽出液の精製工程に係るコストを抑える観点から、好ましくは500~1000ppm(質量百万分率)であり、より好ましくは700~1000ppmである。 Since luteolin in Labiatae plants is also extracted in the extraction step of extracting rosmarinic acid from Labiatae plants, the rosmarinic acid-containing composition obtained through the extraction step contains luteolin.
The content of luteolin in the solid content of the rosmarinic acid-containing composition is preferably 500 to 1000 ppm (mass million) from the viewpoint that the effects of the present invention can be easily enjoyed and the costs related to the extraction step and the purification step of the extract can be suppressed. It is a fraction), and more preferably 700 to 1000 ppm.
ロズマリン酸含有組成物の固形分中のルテオリンの含有量は、本発明の効果を享受しやすく、抽出工程及び抽出液の精製工程に係るコストを抑える観点から、好ましくは500~1000ppm(質量百万分率)であり、より好ましくは700~1000ppmである。 Since luteolin in Labiatae plants is also extracted in the extraction step of extracting rosmarinic acid from Labiatae plants, the rosmarinic acid-containing composition obtained through the extraction step contains luteolin.
The content of luteolin in the solid content of the rosmarinic acid-containing composition is preferably 500 to 1000 ppm (mass million) from the viewpoint that the effects of the present invention can be easily enjoyed and the costs related to the extraction step and the purification step of the extract can be suppressed. It is a fraction), and more preferably 700 to 1000 ppm.
ロズマリン酸含有組成物におけるルテオリンの含有量に対するロズマリン酸の含有量の質量比〔ロズマリン酸の含有量/ルテオリンの含有量〕は、本発発明の効果を享受しやすく、抽出工程及び抽出液の精製工程に係るコストを抑える観点から、好ましくは1000以上、より好ましくは5000以上、さらに好ましくは10000以上である。
The mass ratio of the content of rosmarin acid to the content of luteolin in the composition containing rosmarin acid [content of rosmarin acid / content of luteolin] is easy to enjoy the effects of the present invention, and the extraction step and purification of the extract can be easily enjoyed. From the viewpoint of suppressing the cost related to the process, it is preferably 1000 or more, more preferably 5000 or more, and further preferably 10000 or more.
(活性炭)
本発明において、ロズマリン酸含有組成物に接触させる活性炭の由来原料としては、例えば、オガコ、石炭、ヤシ殻等が挙げられる。なかでも、ルテオリン低減の観点から、ヤシ殻由来のヤシ殻活性炭が好ましい。また、水蒸気等のガスや薬品により賦活した活性炭が好ましく使用される。活性炭の形状は、特に限定されず、例えば、粉末状、粒状、繊維状が挙げられる。
活性炭としては、例えば、クラレコールGW((株)クラレ社製)等の市販品を用いることができる。 (Activated carbon)
In the present invention, examples of the raw material derived from the activated carbon to be brought into contact with the rosmarinic acid-containing composition include ogako, coal, coconut shell and the like. Of these, coconut shell activated carbon derived from coconut shell is preferable from the viewpoint of reducing luteolin. In addition, activated carbon activated by gas such as steam or chemicals is preferably used. The shape of the activated carbon is not particularly limited, and examples thereof include powder, granular, and fibrous.
As the activated carbon, for example, a commercially available product such as Kuraray Coal GW (manufactured by Kuraray Co., Ltd.) can be used.
本発明において、ロズマリン酸含有組成物に接触させる活性炭の由来原料としては、例えば、オガコ、石炭、ヤシ殻等が挙げられる。なかでも、ルテオリン低減の観点から、ヤシ殻由来のヤシ殻活性炭が好ましい。また、水蒸気等のガスや薬品により賦活した活性炭が好ましく使用される。活性炭の形状は、特に限定されず、例えば、粉末状、粒状、繊維状が挙げられる。
活性炭としては、例えば、クラレコールGW((株)クラレ社製)等の市販品を用いることができる。 (Activated carbon)
In the present invention, examples of the raw material derived from the activated carbon to be brought into contact with the rosmarinic acid-containing composition include ogako, coal, coconut shell and the like. Of these, coconut shell activated carbon derived from coconut shell is preferable from the viewpoint of reducing luteolin. In addition, activated carbon activated by gas such as steam or chemicals is preferably used. The shape of the activated carbon is not particularly limited, and examples thereof include powder, granular, and fibrous.
As the activated carbon, for example, a commercially available product such as Kuraray Coal GW (manufactured by Kuraray Co., Ltd.) can be used.
活性炭の使用量は、ロズマリン酸の回収率を高める観点、ルテオリン低減の観点から、ロズマリン酸含有組成物の固形分質量に対して、好ましくは20質量%以上、より好ましくは25質量%以上、さらに好ましくは30質量%以上であり、また、好ましくは100質量%以下、より好ましくは70質量%以下である。そして、活性炭の使用量は、ロズマリン酸含有組成物の固形分質量に対して、好ましくは20~100質量%、より好ましくは25~70質量%、さらに好ましくは30~70質量%である。
The amount of activated carbon used is preferably 20% by mass or more, more preferably 25% by mass or more, and further, from the viewpoint of increasing the recovery rate of rosmarin acid and reducing luteolin, with respect to the solid content mass of the rosmarin acid-containing composition. It is preferably 30% by mass or more, preferably 100% by mass or less, and more preferably 70% by mass or less. The amount of activated carbon used is preferably 20 to 100% by mass, more preferably 25 to 70% by mass, and even more preferably 30 to 70% by mass with respect to the solid content mass of the rosmarinic acid-containing composition.
(エタノール水溶液)
本発明では、ロズマリン酸含有組成物を、エタノール水溶液中で活性炭と接触させる。活性炭との接触時のエタノール水溶液のエタノール濃度はロズマリン酸の回収率を高める観点、ルテオリン低減の観点から、30~50vol%である。
エタノール水溶液の濃度調整は、例えば、ロズマリン酸含有組成物に対して、エタノール水溶液中のエタノール濃度が上記範囲内となるようにエタノールと水を添加・混合する方法や、ロズマリン酸含有組成物に対して、エタノールを添加・混合後、加水してエタノール濃度が上記範囲内となるように調整する方法等が挙げられる。 (Aqueous ethanol solution)
In the present invention, the rosmarinic acid-containing composition is contacted with activated carbon in an aqueous ethanol solution. The ethanol concentration of the aqueous ethanol solution at the time of contact with activated carbon is 30 to 50 vol% from the viewpoint of increasing the recovery rate of rosmarin acid and reducing luteolin.
The concentration of the ethanol aqueous solution can be adjusted, for example, by adding / mixing ethanol and water to the rosmarinic acid-containing composition so that the ethanol concentration in the ethanol aqueous solution is within the above range, or to the rosmarinic acid-containing composition. Then, after adding and mixing ethanol, a method of adding water to adjust the ethanol concentration within the above range can be mentioned.
本発明では、ロズマリン酸含有組成物を、エタノール水溶液中で活性炭と接触させる。活性炭との接触時のエタノール水溶液のエタノール濃度はロズマリン酸の回収率を高める観点、ルテオリン低減の観点から、30~50vol%である。
エタノール水溶液の濃度調整は、例えば、ロズマリン酸含有組成物に対して、エタノール水溶液中のエタノール濃度が上記範囲内となるようにエタノールと水を添加・混合する方法や、ロズマリン酸含有組成物に対して、エタノールを添加・混合後、加水してエタノール濃度が上記範囲内となるように調整する方法等が挙げられる。 (Aqueous ethanol solution)
In the present invention, the rosmarinic acid-containing composition is contacted with activated carbon in an aqueous ethanol solution. The ethanol concentration of the aqueous ethanol solution at the time of contact with activated carbon is 30 to 50 vol% from the viewpoint of increasing the recovery rate of rosmarin acid and reducing luteolin.
The concentration of the ethanol aqueous solution can be adjusted, for example, by adding / mixing ethanol and water to the rosmarinic acid-containing composition so that the ethanol concentration in the ethanol aqueous solution is within the above range, or to the rosmarinic acid-containing composition. Then, after adding and mixing ethanol, a method of adding water to adjust the ethanol concentration within the above range can be mentioned.
エタノール水溶液の使用量は、ルテオリンの低減の観点から、ロズマリン酸含有組成物の固形分に対して、好ましくは5質量倍以上、より好ましくは10質量倍以上であり、また、好ましくは100質量倍以下、より好ましくは50質量倍以下である。そして、エタノール水溶液の使用量は、ロズマリン酸含有組成物の固形分に対して、5~100質量倍が好ましく、10~50質量倍がより好ましい。
From the viewpoint of reducing luteolin, the amount of the aqueous ethanol solution is preferably 5 times by mass or more, more preferably 10 times by mass or more, and preferably 100 times by mass with respect to the solid content of the rosmarinic acid-containing composition. Below, it is more preferably 50 times by mass or less. The amount of the aqueous ethanol solution used is preferably 5 to 100 times by mass, more preferably 10 to 50 times by mass, based on the solid content of the rosmarinic acid-containing composition.
(接触手段)
ロズマリン酸含有組成物を活性炭と接触させる手段としては、エタノール水溶液に活性炭を添加、撹拌して吸着後、濾過操作により活性炭を回収するバッチ式、活性炭を充填したカラムを用いて連続処理により接触させる連続式等が挙げられる。 (Contact means)
As a means for bringing the rosmarinic acid-containing composition into contact with activated carbon, the activated carbon is added to an aqueous ethanol solution, stirred and adsorbed, and then the activated carbon is recovered by a filtration operation. Examples include continuous type.
ロズマリン酸含有組成物を活性炭と接触させる手段としては、エタノール水溶液に活性炭を添加、撹拌して吸着後、濾過操作により活性炭を回収するバッチ式、活性炭を充填したカラムを用いて連続処理により接触させる連続式等が挙げられる。 (Contact means)
As a means for bringing the rosmarinic acid-containing composition into contact with activated carbon, the activated carbon is added to an aqueous ethanol solution, stirred and adsorbed, and then the activated carbon is recovered by a filtration operation. Examples include continuous type.
接触温度は、ルテオリンの低減の観点から、好ましくは10℃以上であり、また、好ましくは50℃以下である。
The contact temperature is preferably 10 ° C. or higher, and preferably 50 ° C. or lower, from the viewpoint of reducing luteolin.
接触時間は、接触手段やスケールにより適宜選択することができるが、例えば、ルテオリンの低減の観点から、好ましくは4時間以上、より好ましくは10時間以上である。
The contact time can be appropriately selected depending on the contact means and scale, but for example, from the viewpoint of reducing luteolin, it is preferably 4 hours or more, more preferably 10 hours or more.
(精製ロズマリン酸含有組成物)
活性炭との接触後、遠心分離、濾過等の固液分離操作により処理液を回収することにより、本発明の精製ロズマリン酸含有組成物を得ることができる。
精製ロズマリン酸含有組成物の形態は、特に限定されず、固形、半固形又は液状を問わないが、固形分濃度を高める観点から、上記で回収した処理液は、常圧濃縮、減圧濃縮、膜濃縮等の通常の手段を用いて濃縮することが好ましい。濃縮後は、噴霧乾燥や凍結乾燥等の通常の手段を用いて乾燥してもよい。 (Purified rosmarinic acid-containing composition)
The purified rosmarinic acid-containing composition of the present invention can be obtained by recovering the treated liquid by a solid-liquid separation operation such as centrifugation or filtration after contact with activated carbon.
The form of the purified rosmarinic acid-containing composition is not particularly limited and may be solid, semi-solid or liquid, but from the viewpoint of increasing the solid content concentration, the treatment liquid recovered above can be concentrated under normal pressure, concentrated under reduced pressure, or membrane. It is preferable to concentrate by using a usual means such as concentration. After concentration, it may be dried by ordinary means such as spray drying and freeze drying.
活性炭との接触後、遠心分離、濾過等の固液分離操作により処理液を回収することにより、本発明の精製ロズマリン酸含有組成物を得ることができる。
精製ロズマリン酸含有組成物の形態は、特に限定されず、固形、半固形又は液状を問わないが、固形分濃度を高める観点から、上記で回収した処理液は、常圧濃縮、減圧濃縮、膜濃縮等の通常の手段を用いて濃縮することが好ましい。濃縮後は、噴霧乾燥や凍結乾燥等の通常の手段を用いて乾燥してもよい。 (Purified rosmarinic acid-containing composition)
The purified rosmarinic acid-containing composition of the present invention can be obtained by recovering the treated liquid by a solid-liquid separation operation such as centrifugation or filtration after contact with activated carbon.
The form of the purified rosmarinic acid-containing composition is not particularly limited and may be solid, semi-solid or liquid, but from the viewpoint of increasing the solid content concentration, the treatment liquid recovered above can be concentrated under normal pressure, concentrated under reduced pressure, or membrane. It is preferable to concentrate by using a usual means such as concentration. After concentration, it may be dried by ordinary means such as spray drying and freeze drying.
本発明において、ロズマリン酸含有組成物からのロズマリン酸の回収率は、好ましくは80%以上、より好ましくは90%以上という高い収率とすることができる。
精製ロズマリン酸含有組成物において、固形分中のロズマリン酸の純度は、好ましくは10質量%以上、より好ましくは14質量%以上である。 In the present invention, the recovery rate of rosmarin acid from the rosmarin acid-containing composition can be as high as 80% or more, more preferably 90% or more.
In the purified rosmarinic acid-containing composition, the purity of rosmarinic acid in the solid content is preferably 10% by mass or more, more preferably 14% by mass or more.
精製ロズマリン酸含有組成物において、固形分中のロズマリン酸の純度は、好ましくは10質量%以上、より好ましくは14質量%以上である。 In the present invention, the recovery rate of rosmarin acid from the rosmarin acid-containing composition can be as high as 80% or more, more preferably 90% or more.
In the purified rosmarinic acid-containing composition, the purity of rosmarinic acid in the solid content is preferably 10% by mass or more, more preferably 14% by mass or more.
一方で、ルテオリン量は低減する。そのため、本発明の精製ロズマリン酸含有組成物の水溶液は透明性が高い。
精製ロズマリン酸含有組成物の固形分中のルテオリンの含有量は、水溶液の透明性の観点から、好ましくは150ppmm以下、より好ましくは110ppm以下、さらに好ましくは100ppm以下である。
精製ロズマリン酸含有組成物におけるルテオリンの含有量に対するロズマリン酸の含有量の質量比〔ロズマリン酸の含有量/ルテオリンの含有量〕は、水溶液の透明性の観点から、好ましくは1000以上、より好ましくは1400以上、更に好ましくは5000以上、より更に好ましくは10000以上である。
また、後記実施例に記載した方法で測定される精製ロズマリン酸含有組成物の固形分1質量%水溶液の波長680nmの吸光度は、好ましくは0.15以下であり、より好ましくは0.10以下である。 On the other hand, the amount of luteolin is reduced. Therefore, the aqueous solution of the purified rosmarinic acid-containing composition of the present invention has high transparency.
The content of luteolin in the solid content of the purified rosmarinic acid-containing composition is preferably 150 ppmm or less, more preferably 110 ppm or less, still more preferably 100 ppm or less, from the viewpoint of the transparency of the aqueous solution.
The mass ratio of the content of rosmarin acid to the content of luteolin in the purified rosmarin acid-containing composition [the content of rosmarin acid / the content of luteolin] is preferably 1000 or more, more preferably 1000 or more, from the viewpoint of the transparency of the aqueous solution. It is 1400 or more, more preferably 5000 or more, and even more preferably 10000 or more.
Further, the absorbance of the purified rosmarinic acid-containing composition having a solid content of 1% by mass at a wavelength of 680 nm measured by the method described in Examples below is preferably 0.15 or less, more preferably 0.10 or less. be.
精製ロズマリン酸含有組成物の固形分中のルテオリンの含有量は、水溶液の透明性の観点から、好ましくは150ppmm以下、より好ましくは110ppm以下、さらに好ましくは100ppm以下である。
精製ロズマリン酸含有組成物におけるルテオリンの含有量に対するロズマリン酸の含有量の質量比〔ロズマリン酸の含有量/ルテオリンの含有量〕は、水溶液の透明性の観点から、好ましくは1000以上、より好ましくは1400以上、更に好ましくは5000以上、より更に好ましくは10000以上である。
また、後記実施例に記載した方法で測定される精製ロズマリン酸含有組成物の固形分1質量%水溶液の波長680nmの吸光度は、好ましくは0.15以下であり、より好ましくは0.10以下である。 On the other hand, the amount of luteolin is reduced. Therefore, the aqueous solution of the purified rosmarinic acid-containing composition of the present invention has high transparency.
The content of luteolin in the solid content of the purified rosmarinic acid-containing composition is preferably 150 ppmm or less, more preferably 110 ppm or less, still more preferably 100 ppm or less, from the viewpoint of the transparency of the aqueous solution.
The mass ratio of the content of rosmarin acid to the content of luteolin in the purified rosmarin acid-containing composition [the content of rosmarin acid / the content of luteolin] is preferably 1000 or more, more preferably 1000 or more, from the viewpoint of the transparency of the aqueous solution. It is 1400 or more, more preferably 5000 or more, and even more preferably 10000 or more.
Further, the absorbance of the purified rosmarinic acid-containing composition having a solid content of 1% by mass at a wavelength of 680 nm measured by the method described in Examples below is preferably 0.15 or less, more preferably 0.10 or less. be.
上述した実施形態に関し、本発明はさらに以下の製造方法及び組成物を開示する。
Regarding the above-described embodiment, the present invention further discloses the following production method and composition.
<1>シソ科植物からロズマリン酸を抽出する抽出工程を経て得られ、固形分中のロズマリン酸の含有量が7質量%以上であるロズマリン酸含有組成物を、30~50vol%エタノール水溶液中で活性炭と接触させる接触工程を含む、精製ロズマリン酸含有組成物の製造方法。
<1> A rosmarinic acid-containing composition obtained through an extraction step of extracting rosmarinic acid from a Labiatae plant and having a rosmarinic acid content of 7% by mass or more in a solid content is prepared in a 30 to 50 vol% aqueous ethanol solution. A method for producing a purified rosmarinic acid-containing composition, which comprises a contacting step of contacting with activated carbon.
<2>シソ科植物が、好ましくはシソ科シソ属の植物であり、より好ましくは赤シソ又は青シソであり、さらに好ましくは赤シソである<1>記載の精製ロズマリン酸含有組成物の製造方法。
<3>シソ科植物の使用部位が、好ましくは全草、葉、茎、芽、花、枝、根、種子、並びにこれらの混合物であり、より好ましくは葉である<1>又は<2>記載の精製ロズマリン酸含有組成物の製造方法。
<4>ロズマリン酸含有組成物の固形分中のロズマリン酸の含有量が7質量%以上であって、好ましくは10質量%以上であり、より好ましくは15質量%以上であり、また、好ましくは30質量%以下であり、より好ましくは20質量%以下であり、また、好ましくは7~30質量%、より好ましくは10~20質量%、さらに好ましくは15~20質量%である<1>~<3>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<5>ロズマリン酸含有組成物がルテオリンを含み、ロズマリン酸含有組成物におけるルテオリン含有量に対するロズマリン酸含有量の質量比が、好ましくは1000以上、より好ましくは5000以上、さらに好ましくは10000以上である<1>~<4>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<6>ロズマリン酸含有組成物の固形分中のルテオリンの含有量が、好ましくは500ppm(質量百万分率)以上、より好ましくは700ppm以上であり、また、好ましくは1000ppm以下である<5>記載の精製ロズマリン酸含有組成物の製造方法。
<7>活性炭の使用量が、ロズマリン酸含有組成物の固形分質量に対して、好ましくは20質量%以上、より好ましくは25質量%以上、さらに好ましくは30質量%以上であり、また、好ましくは100質量%以下、より好ましくは70質量%以下であり、また、好ましくは20~100質量%、より好ましくは25~70質量%、さらに好ましくは30~70質量%である<1>~<6>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<8>活性炭が、好ましくはヤシ殻由来のヤシ殻活性炭であり、より好ましくは粒状のヤシ殻活性炭である<1>~<7>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<9>エタノール水溶液の使用量が、ロズマリン酸含有組成物の固形分に対して、好ましくは5質量倍以上、より好ましくは10質量倍以上であり、また、好ましくは100質量倍以下、より好ましくは50質量倍以下であり、また、好ましくは5~100質量倍、より好ましくは10~50質量倍である<1>~<8>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<10>抽出工程の後に、抽出液を濃縮し、次いでエタノール又はエタノール水溶液を添加して生じた沈殿物を除去する精製工程を含む、<1>~<9>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。 <2> Production of the purified rosmarinic acid-containing composition according to <1>, wherein the Labiatae plant is preferably a plant belonging to the Labiatae family, more preferably red perilla or blue perilla, and further preferably red perilla. Method.
<3> The site of use of Labiatae plants is preferably whole plants, leaves, stems, buds, flowers, branches, roots, seeds, and mixtures thereof, and more preferably leaves <1> or <2>. The method for producing a purified rosmarinic acid-containing composition according to the above method.
<4> The content of rosmarinic acid in the solid content of the rosmarinic acid-containing composition is 7% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, and preferably. It is 30% by mass or less, more preferably 20% by mass or less, preferably 7 to 30% by mass, more preferably 10 to 20% by mass, still more preferably 15 to 20% by mass <1> to. The method for producing a purified rosmarinic acid-containing composition according to any one of <3>.
<5> The rosmarinic acid-containing composition contains luteolin, and the mass ratio of the rosumelic acid content to the luteolin content in the rosmarin acid-containing composition is preferably 1000 or more, more preferably 5000 or more, still more preferably 10,000 or more. The method for producing a purified rosmarinic acid-containing composition according to any one of <1> to <4>.
<6> The content of luteolin in the solid content of the rosmarinic acid-containing composition is preferably 500 ppm (parts per million by mass) or more, more preferably 700 ppm or more, and preferably 1000 ppm or less <5>. The method for producing a purified rosmarinic acid-containing composition according to the above method.
<7> The amount of the activated charcoal used is preferably 20% by mass or more, more preferably 25% by mass or more, still more preferably 30% by mass or more, and more preferably 30% by mass or more, based on the solid content mass of the rosmarinic acid-containing composition. Is 100% by mass or less, more preferably 70% by mass or less, preferably 20 to 100% by mass, more preferably 25 to 70% by mass, still more preferably 30 to 70% by mass <1> to <. 6> The method for producing a purified rosmarinic acid-containing composition according to any one of 6.
<8> The method for producing a purified rosmarinic acid-containing composition according to any one of <1> to <7>, wherein the activated carbon is preferably coconut shell activated carbon derived from coconut shell, and more preferably granular coconut shell activated carbon. ..
<9> The amount of the ethanol aqueous solution used is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 100% by mass or less, more preferably, with respect to the solid content of the rosmarinic acid-containing composition. The method for producing a purified rosmarinic acid-containing composition according to any one of <1> to <8>, wherein is 50 times by mass or less, preferably 5 to 100 times by mass, and more preferably 10 to 50 times by mass. ..
<10> The purified rosmarin according to any one of <1> to <9>, which comprises a purification step of concentrating the extract and then adding ethanol or an aqueous ethanol solution to remove the precipitate formed after the extraction step. A method for producing an acid-containing composition.
<3>シソ科植物の使用部位が、好ましくは全草、葉、茎、芽、花、枝、根、種子、並びにこれらの混合物であり、より好ましくは葉である<1>又は<2>記載の精製ロズマリン酸含有組成物の製造方法。
<4>ロズマリン酸含有組成物の固形分中のロズマリン酸の含有量が7質量%以上であって、好ましくは10質量%以上であり、より好ましくは15質量%以上であり、また、好ましくは30質量%以下であり、より好ましくは20質量%以下であり、また、好ましくは7~30質量%、より好ましくは10~20質量%、さらに好ましくは15~20質量%である<1>~<3>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<5>ロズマリン酸含有組成物がルテオリンを含み、ロズマリン酸含有組成物におけるルテオリン含有量に対するロズマリン酸含有量の質量比が、好ましくは1000以上、より好ましくは5000以上、さらに好ましくは10000以上である<1>~<4>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<6>ロズマリン酸含有組成物の固形分中のルテオリンの含有量が、好ましくは500ppm(質量百万分率)以上、より好ましくは700ppm以上であり、また、好ましくは1000ppm以下である<5>記載の精製ロズマリン酸含有組成物の製造方法。
<7>活性炭の使用量が、ロズマリン酸含有組成物の固形分質量に対して、好ましくは20質量%以上、より好ましくは25質量%以上、さらに好ましくは30質量%以上であり、また、好ましくは100質量%以下、より好ましくは70質量%以下であり、また、好ましくは20~100質量%、より好ましくは25~70質量%、さらに好ましくは30~70質量%である<1>~<6>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<8>活性炭が、好ましくはヤシ殻由来のヤシ殻活性炭であり、より好ましくは粒状のヤシ殻活性炭である<1>~<7>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<9>エタノール水溶液の使用量が、ロズマリン酸含有組成物の固形分に対して、好ましくは5質量倍以上、より好ましくは10質量倍以上であり、また、好ましくは100質量倍以下、より好ましくは50質量倍以下であり、また、好ましくは5~100質量倍、より好ましくは10~50質量倍である<1>~<8>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。
<10>抽出工程の後に、抽出液を濃縮し、次いでエタノール又はエタノール水溶液を添加して生じた沈殿物を除去する精製工程を含む、<1>~<9>のいずれかに記載の精製ロズマリン酸含有組成物の製造方法。 <2> Production of the purified rosmarinic acid-containing composition according to <1>, wherein the Labiatae plant is preferably a plant belonging to the Labiatae family, more preferably red perilla or blue perilla, and further preferably red perilla. Method.
<3> The site of use of Labiatae plants is preferably whole plants, leaves, stems, buds, flowers, branches, roots, seeds, and mixtures thereof, and more preferably leaves <1> or <2>. The method for producing a purified rosmarinic acid-containing composition according to the above method.
<4> The content of rosmarinic acid in the solid content of the rosmarinic acid-containing composition is 7% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, and preferably. It is 30% by mass or less, more preferably 20% by mass or less, preferably 7 to 30% by mass, more preferably 10 to 20% by mass, still more preferably 15 to 20% by mass <1> to. The method for producing a purified rosmarinic acid-containing composition according to any one of <3>.
<5> The rosmarinic acid-containing composition contains luteolin, and the mass ratio of the rosumelic acid content to the luteolin content in the rosmarin acid-containing composition is preferably 1000 or more, more preferably 5000 or more, still more preferably 10,000 or more. The method for producing a purified rosmarinic acid-containing composition according to any one of <1> to <4>.
<6> The content of luteolin in the solid content of the rosmarinic acid-containing composition is preferably 500 ppm (parts per million by mass) or more, more preferably 700 ppm or more, and preferably 1000 ppm or less <5>. The method for producing a purified rosmarinic acid-containing composition according to the above method.
<7> The amount of the activated charcoal used is preferably 20% by mass or more, more preferably 25% by mass or more, still more preferably 30% by mass or more, and more preferably 30% by mass or more, based on the solid content mass of the rosmarinic acid-containing composition. Is 100% by mass or less, more preferably 70% by mass or less, preferably 20 to 100% by mass, more preferably 25 to 70% by mass, still more preferably 30 to 70% by mass <1> to <. 6> The method for producing a purified rosmarinic acid-containing composition according to any one of 6.
<8> The method for producing a purified rosmarinic acid-containing composition according to any one of <1> to <7>, wherein the activated carbon is preferably coconut shell activated carbon derived from coconut shell, and more preferably granular coconut shell activated carbon. ..
<9> The amount of the ethanol aqueous solution used is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 100% by mass or less, more preferably, with respect to the solid content of the rosmarinic acid-containing composition. The method for producing a purified rosmarinic acid-containing composition according to any one of <1> to <8>, wherein is 50 times by mass or less, preferably 5 to 100 times by mass, and more preferably 10 to 50 times by mass. ..
<10> The purified rosmarin according to any one of <1> to <9>, which comprises a purification step of concentrating the extract and then adding ethanol or an aqueous ethanol solution to remove the precipitate formed after the extraction step. A method for producing an acid-containing composition.
[ロズマリン酸の定量 LC-UV]
試料中のロズマリン酸量は次の条件により測定した。
HPLC:Agilent1260 Infinity
Column:CAPCELL CORE C18 (2.1mml×100mm 2.7μm) 製品番号51105(大阪ソーダ社)
Eluent:A 0.1vol% ぎ酸水溶液 B アセトニトリル
Flow :0.7mL/min
Temp : 40℃
Detect : 320nm
Inject : 50vol%エタノール水溶液
検量線:市販試薬RA(Carbosynth社, 純度98.2%)を50vol%エタノール水溶液で希釈して調製した1000-10ppm間の8点で作成した。 [Quantitative LC-UV of rosmarinic acid]
The amount of rosmarinic acid in the sample was measured under the following conditions.
HPLC: Agilent1260 Infinity
Column: CAPCELL CORE C18 (2.1mml x 100mm 2.7μm) Product number 51105 (Osaka Soda Co., Ltd.)
Eluent: A 0.1vol% aqueous solution of formic acid B acetonitrile
Flow: 0.7mL / min
Temp: 40 ℃
Detect: 320nm
Inject: 50 vol% ethanol aqueous solution Calibration curve: Prepared at 8 points between 1000 and 10 ppm prepared by diluting a commercially available reagent RA (Carbosynth, purity 98.2%) with a 50 vol% ethanol aqueous solution.
試料中のロズマリン酸量は次の条件により測定した。
HPLC:Agilent1260 Infinity
Column:CAPCELL CORE C18 (2.1mml×100mm 2.7μm) 製品番号51105(大阪ソーダ社)
Eluent:A 0.1vol% ぎ酸水溶液 B アセトニトリル
Flow :0.7mL/min
Temp : 40℃
Detect : 320nm
Inject : 50vol%エタノール水溶液
検量線:市販試薬RA(Carbosynth社, 純度98.2%)を50vol%エタノール水溶液で希釈して調製した1000-10ppm間の8点で作成した。 [Quantitative LC-UV of rosmarinic acid]
The amount of rosmarinic acid in the sample was measured under the following conditions.
HPLC: Agilent1260 Infinity
Column: CAPCELL CORE C18 (2.1mml x 100mm 2.7μm) Product number 51105 (Osaka Soda Co., Ltd.)
Eluent: A 0.1vol% aqueous solution of formic acid B acetonitrile
Flow: 0.7mL / min
Temp: 40 ℃
Detect: 320nm
Inject: 50 vol% ethanol aqueous solution Calibration curve: Prepared at 8 points between 1000 and 10 ppm prepared by diluting a commercially available reagent RA (Carbosynth, purity 98.2%) with a 50 vol% ethanol aqueous solution.
[ルテオリンの定量 LC-MS/MS]
試料中のルテオリン量は次の条件により測定した。
HPLC:Sciex ExionLC (エービー・サイエックス社)
MS/MS:TRIPLE QUAD 4500 (エービー・サイエックス社)
Column:Capcell CoreC18 (2.1mm×50mm, 2.7μm) 製品番号51103(大阪ソーダ社)
Eluent:A 0.1vol%ぎ酸水 B アセトニトリル
Flow : 0.7 mL/min
Temp : 40℃
Inject : 50vol%エタノール水溶液
検量線:市販試薬ルテオリン(富士フイルム和光純薬社, 純度95%)を50%エタノール水溶液で希釈して調製した1000-0.25μg/mL間の12点で作成した。 [Luteolin Quantitative LC-MS / MS]
The amount of luteolin in the sample was measured under the following conditions.
HPLC: Sciex Exion LC (AB Sciex)
MS / MS: TRIPLE QUAD 4500 (AB SIX)
Column: Capcell CoreC18 (2.1mm x 50mm, 2.7μm) Product number 51103 (Osaka Soda Co., Ltd.)
Eluent: A 0.1vol% formic acid water B acetonitrile
Flow: 0.7 mL / min
Temp: 40 ℃
Inject: 50 vol% ethanol aqueous solution calibration curve: Commercially available reagent Wako Pure Chemical Industries, Ltd., purity 95% was diluted with 50% ethanol aqueous solution and prepared at 12 points between 1000 and 0.25 μg / mL.
試料中のルテオリン量は次の条件により測定した。
HPLC:Sciex ExionLC (エービー・サイエックス社)
MS/MS:TRIPLE QUAD 4500 (エービー・サイエックス社)
Column:Capcell CoreC18 (2.1mm×50mm, 2.7μm) 製品番号51103(大阪ソーダ社)
Eluent:A 0.1vol%ぎ酸水 B アセトニトリル
Flow : 0.7 mL/min
Temp : 40℃
Inject : 50vol%エタノール水溶液
検量線:市販試薬ルテオリン(富士フイルム和光純薬社, 純度95%)を50%エタノール水溶液で希釈して調製した1000-0.25μg/mL間の12点で作成した。 [Luteolin Quantitative LC-MS / MS]
The amount of luteolin in the sample was measured under the following conditions.
HPLC: Sciex Exion LC (AB Sciex)
MS / MS: TRIPLE QUAD 4500 (AB SIX)
Column: Capcell CoreC18 (2.1mm x 50mm, 2.7μm) Product number 51103 (Osaka Soda Co., Ltd.)
Eluent: A 0.1vol% formic acid water B acetonitrile
Flow: 0.7 mL / min
Temp: 40 ℃
Inject: 50 vol% ethanol aqueous solution calibration curve: Commercially available reagent Wako Pure Chemical Industries, Ltd., purity 95% was diluted with 50% ethanol aqueous solution and prepared at 12 points between 1000 and 0.25 μg / mL.
[ロズマリン酸の純度]
ロズマリン酸の定量値より下記の計算式によって求めた。
ロズマリン酸純度(%)=(エキス溶液中のロズマリン酸量 mg/mL)÷(エキス溶液中の固形分量 mg/mL)×100(%) [Purity of rosmarinic acid]
It was calculated from the quantitative value of rosmarinic acid by the following formula.
Rosmarin acid purity (%) = (Amount of rosmarin acid in extract solution mg / mL) ÷ (Amount of solid content in extract solution mg / mL) x 100 (%)
ロズマリン酸の定量値より下記の計算式によって求めた。
ロズマリン酸純度(%)=(エキス溶液中のロズマリン酸量 mg/mL)÷(エキス溶液中の固形分量 mg/mL)×100(%) [Purity of rosmarinic acid]
It was calculated from the quantitative value of rosmarinic acid by the following formula.
Rosmarin acid purity (%) = (Amount of rosmarin acid in extract solution mg / mL) ÷ (Amount of solid content in extract solution mg / mL) x 100 (%)
[ロズマリン酸の回収率]
下記の計算式によって求めた。
ロズマリン酸の回収率(%)=(活性炭処理後のエキス粉末凍結乾燥重量×活性炭処理後のエキス粉末ロズマリン酸純度)÷(活性炭処理前のエキス粉末凍結乾燥重量×活性炭処理前のエキス粉末ロズマリン酸純度) ×100(%) [Recovery rate of rosmarinic acid]
It was calculated by the following formula.
Recovery rate of rosmarinic acid (%) = (weight of extract powder frozen and dried after activated carbon treatment x purity of extract powder rosmarinic acid after treated with activated carbon) ÷ (weight of lyophilized extract powder before activated carbon treatment x extract powder rosmarinic acid before activated carbon treatment) Purity) x 100 (%)
下記の計算式によって求めた。
ロズマリン酸の回収率(%)=(活性炭処理後のエキス粉末凍結乾燥重量×活性炭処理後のエキス粉末ロズマリン酸純度)÷(活性炭処理前のエキス粉末凍結乾燥重量×活性炭処理前のエキス粉末ロズマリン酸純度) ×100(%) [Recovery rate of rosmarinic acid]
It was calculated by the following formula.
Recovery rate of rosmarinic acid (%) = (weight of extract powder frozen and dried after activated carbon treatment x purity of extract powder rosmarinic acid after treated with activated carbon) ÷ (weight of lyophilized extract powder before activated carbon treatment x extract powder rosmarinic acid before activated carbon treatment) Purity) x 100 (%)
実施例及び比較例
1.クエン酸浸漬赤シソ乾燥葉である赤しそKU(こだま食品社製)200kgに80℃の熱水2200kgと6M 水酸化ナトリウム水溶液73.3kgを加え、pH4.5に調整した後、90℃で1時間熱水抽出した。抽出液をろ過し、225kgまで濃縮後、95vol%エタノールを77kg加えて、82vol%エタノール水溶液に調整し、30℃で1時間撹拌して生じた沈殿物を除去し、さらに186kgまで減圧濃縮後に噴霧乾燥して得た赤シソエキス粉末を用いた。赤シソエキス粉末の固形分中のロズマリン酸量は17.1質量%、ルテオリン量は918.4ppm(質量百万分率)であった。
赤シソエキス粉末500mgを70,50,30,10vol%エタノール水溶液又は蒸留水20mLにそれぞれ溶解し、活性炭(クラレコールGW 48/100D、クラレ社製)を赤シソエキス粉末(固形分)に対して50,25,12.5質量%加え、30℃で18時間撹拌した。処理後0.2μmPESフィルタユニット(サーモフィッシャーサイエンティフィック社製)でろ過して活性炭を除き、ろ液を減圧濃縮後に凍結乾燥して、精製エキス粉末を約450mgずつ得た。
活性炭処理により得られた精製エキス粉末について、高速液体クロマトグラフィー-紫外可視光検出(LC-UV)によりロズマリン酸を定量し、活性炭処理後のロズマリン酸回収率及びロズマリン酸純度を算出した。また、高速液体クロマトグラフィータンデム質量分析検出(LC-MS/MS)により、ルテオリンを定量した。
結果を表3及び表4に示す。 Examples and Comparative Examples 1. Add 2200 kg of hot water at 80 ° C and 73.3 kg of 6M sodium hydroxide aqueous solution to 200 kg of red shiso KU (manufactured by Kodama Foods Co., Ltd.), which is a dried leaf of red perilla soaked in citric acid, adjust the pH to 4.5, and then 1 at 90 ° C. Time hot water extraction. The extract is filtered and concentrated to 225 kg, then 77 kg of 95 vol% ethanol is added to prepare an 82 vol% ethanol aqueous solution, and the mixture is stirred at 30 ° C. for 1 hour to remove the resulting precipitate. The red perilla extract powder obtained by drying was used. The amount of rosmarinic acid in the solid content of the red perilla extract powder was 17.1% by mass, and the amount of luteolin was 918.4 ppm (parts by mass).
Dissolve 500 mg of red perilla extract powder in 70, 50, 30, 10 vol% ethanol aqueous solution or 20 mL of distilled water, respectively, and add activated carbon (Kuraraycol GW 48 / 100D, manufactured by Kuraray Co., Ltd.) to 50, 50, per red perilla extract powder (solid content). 25,12.5% by mass was added, and the mixture was stirred at 30 ° C. for 18 hours. After the treatment, activated carbon was removed by filtering with a 0.2 μm PES filter unit (manufactured by Thermo Fisher Scientific), the filtrate was concentrated under reduced pressure and then freeze-dried to obtain about 450 mg of purified extract powder.
For the purified extract powder obtained by the activated carbon treatment, rosmarinic acid was quantified by high performance liquid chromatography-ultraviolet visible light detection (LC-UV), and the rosmarinic acid recovery rate and rosmarinic acid purity after the activated carbon treatment were calculated. In addition, luteolin was quantified by high performance liquid chromatography tandem mass spectrometry detection (LC-MS / MS).
The results are shown in Tables 3 and 4.
1.クエン酸浸漬赤シソ乾燥葉である赤しそKU(こだま食品社製)200kgに80℃の熱水2200kgと6M 水酸化ナトリウム水溶液73.3kgを加え、pH4.5に調整した後、90℃で1時間熱水抽出した。抽出液をろ過し、225kgまで濃縮後、95vol%エタノールを77kg加えて、82vol%エタノール水溶液に調整し、30℃で1時間撹拌して生じた沈殿物を除去し、さらに186kgまで減圧濃縮後に噴霧乾燥して得た赤シソエキス粉末を用いた。赤シソエキス粉末の固形分中のロズマリン酸量は17.1質量%、ルテオリン量は918.4ppm(質量百万分率)であった。
赤シソエキス粉末500mgを70,50,30,10vol%エタノール水溶液又は蒸留水20mLにそれぞれ溶解し、活性炭(クラレコールGW 48/100D、クラレ社製)を赤シソエキス粉末(固形分)に対して50,25,12.5質量%加え、30℃で18時間撹拌した。処理後0.2μmPESフィルタユニット(サーモフィッシャーサイエンティフィック社製)でろ過して活性炭を除き、ろ液を減圧濃縮後に凍結乾燥して、精製エキス粉末を約450mgずつ得た。
活性炭処理により得られた精製エキス粉末について、高速液体クロマトグラフィー-紫外可視光検出(LC-UV)によりロズマリン酸を定量し、活性炭処理後のロズマリン酸回収率及びロズマリン酸純度を算出した。また、高速液体クロマトグラフィータンデム質量分析検出(LC-MS/MS)により、ルテオリンを定量した。
結果を表3及び表4に示す。 Examples and Comparative Examples 1. Add 2200 kg of hot water at 80 ° C and 73.3 kg of 6M sodium hydroxide aqueous solution to 200 kg of red shiso KU (manufactured by Kodama Foods Co., Ltd.), which is a dried leaf of red perilla soaked in citric acid, adjust the pH to 4.5, and then 1 at 90 ° C. Time hot water extraction. The extract is filtered and concentrated to 225 kg, then 77 kg of 95 vol% ethanol is added to prepare an 82 vol% ethanol aqueous solution, and the mixture is stirred at 30 ° C. for 1 hour to remove the resulting precipitate. The red perilla extract powder obtained by drying was used. The amount of rosmarinic acid in the solid content of the red perilla extract powder was 17.1% by mass, and the amount of luteolin was 918.4 ppm (parts by mass).
Dissolve 500 mg of red perilla extract powder in 70, 50, 30, 10 vol% ethanol aqueous solution or 20 mL of distilled water, respectively, and add activated carbon (Kuraraycol GW 48 / 100D, manufactured by Kuraray Co., Ltd.) to 50, 50, per red perilla extract powder (solid content). 25,12.5% by mass was added, and the mixture was stirred at 30 ° C. for 18 hours. After the treatment, activated carbon was removed by filtering with a 0.2 μm PES filter unit (manufactured by Thermo Fisher Scientific), the filtrate was concentrated under reduced pressure and then freeze-dried to obtain about 450 mg of purified extract powder.
For the purified extract powder obtained by the activated carbon treatment, rosmarinic acid was quantified by high performance liquid chromatography-ultraviolet visible light detection (LC-UV), and the rosmarinic acid recovery rate and rosmarinic acid purity after the activated carbon treatment were calculated. In addition, luteolin was quantified by high performance liquid chromatography tandem mass spectrometry detection (LC-MS / MS).
The results are shown in Tables 3 and 4.
2.水溶液の透明性の評価
活性炭処理前の赤シソエキス粉末と、実施例1及び比較例7の精製エキス粉末について、50.0mgをイオン交換水5.0mLに溶解して、固形分濃度1.0質量%の水溶液を調製した。
これら水溶液について、目視と吸光度測定により濁りを評価した。目視評価では、パネラーが目視で観察し、〇:透明水溶液、△:わずかに濁りがある、×:濁りがある、の三段階で評価した。
吸光度測定では、透明平底96ウェルプレート(コーニング社、型番351172)の各ウェルに水溶液200μLを計りとり、プレートリーダー(TECAN社 Spark)を用いて濁りに対応する680nmの吸光度を測定した。
評価結果を表5に示す。
また、図1に、処理前、比較例7、比較例8及び実施例1の水溶液の外観を示す。 2. 2. Evaluation of Aqueous Solution Transparency For the red perilla extract powder before activated carbon treatment and the purified extract powders of Example 1 and Comparative Example 7, 50.0 mg was dissolved in 5.0 mL of ion-exchanged water, and the solid content concentration was 1.0 mass. % Aqueous solution was prepared.
The turbidity of these aqueous solutions was evaluated visually and by measuring the absorbance. In the visual evaluation, the panelists visually observed and evaluated in three stages: ◯: transparent aqueous solution, Δ: slightly turbid, and ×: turbid.
In the absorbance measurement, 200 μL of an aqueous solution was measured in each well of a transparent flat bottom 96-well plate (Corning, model number 351172), and the absorbance at 680 nm corresponding to turbidity was measured using a plate reader (TECAN Spark).
The evaluation results are shown in Table 5.
Further, FIG. 1 shows the appearance of the aqueous solutions of Comparative Example 7, Comparative Example 8 and Example 1 before the treatment.
活性炭処理前の赤シソエキス粉末と、実施例1及び比較例7の精製エキス粉末について、50.0mgをイオン交換水5.0mLに溶解して、固形分濃度1.0質量%の水溶液を調製した。
これら水溶液について、目視と吸光度測定により濁りを評価した。目視評価では、パネラーが目視で観察し、〇:透明水溶液、△:わずかに濁りがある、×:濁りがある、の三段階で評価した。
吸光度測定では、透明平底96ウェルプレート(コーニング社、型番351172)の各ウェルに水溶液200μLを計りとり、プレートリーダー(TECAN社 Spark)を用いて濁りに対応する680nmの吸光度を測定した。
評価結果を表5に示す。
また、図1に、処理前、比較例7、比較例8及び実施例1の水溶液の外観を示す。 2. 2. Evaluation of Aqueous Solution Transparency For the red perilla extract powder before activated carbon treatment and the purified extract powders of Example 1 and Comparative Example 7, 50.0 mg was dissolved in 5.0 mL of ion-exchanged water, and the solid content concentration was 1.0 mass. % Aqueous solution was prepared.
The turbidity of these aqueous solutions was evaluated visually and by measuring the absorbance. In the visual evaluation, the panelists visually observed and evaluated in three stages: ◯: transparent aqueous solution, Δ: slightly turbid, and ×: turbid.
In the absorbance measurement, 200 μL of an aqueous solution was measured in each well of a transparent flat bottom 96-well plate (Corning, model number 351172), and the absorbance at 680 nm corresponding to turbidity was measured using a plate reader (TECAN Spark).
The evaluation results are shown in Table 5.
Further, FIG. 1 shows the appearance of the aqueous solutions of Comparative Example 7, Comparative Example 8 and Example 1 before the treatment.
表3~表5、図1より、本発明の方法によれば、活性炭処理におけるロズマリン酸のロスを抑えてロズマリン酸を収率良く回収しながらも、ルテオリンを選択的に低減でき、水溶液の透明性を向上できることが確認された。
From Tables 3 to 5 and FIG. 1, according to the method of the present invention, luteolin can be selectively reduced while suppressing the loss of rosmarinic acid in the activated carbon treatment and recovering rosmarinic acid in good yield, and the aqueous solution is transparent. It was confirmed that the sex could be improved.
Claims (6)
- シソ科植物からロズマリン酸を抽出する抽出工程を経て得られ、固形分中のロズマリン酸の含有量が7質量%以上であるロズマリン酸含有組成物を、30~50vol%エタノール水溶液中で活性炭と接触させる接触工程を含む、精製ロズマリン酸含有組成物の製造方法。 A rosmarinic acid-containing composition obtained through an extraction step of extracting rosmarinic acid from a Labiatae plant and having a rosmarinic acid content of 7% by mass or more in a solid content is contacted with activated charcoal in a 30-50 vol% aqueous ethanol solution. A method for producing a purified rosmarinic acid-containing composition, which comprises a contacting step.
- ロズマリン酸含有組成物がルテオリンを含み、ロズマリン酸含有組成物におけるルテオリン含有量に対するロズマリン酸含有量の質量比が1000以上である請求項1記載の精製ロズマリン酸含有組成物の製造方法。 The method for producing a purified rosmarinic acid-containing composition according to claim 1, wherein the rosmarinic acid-containing composition contains luteolin, and the mass ratio of the rosmarinic acid content to the luteolin content in the rosmarinic acid-containing composition is 1000 or more.
- 活性炭の使用量が、ロズマリン酸含有組成物の固形分質量に対して20~100質量%である請求項1又は2記載の精製ロズマリン酸含有組成物の製造方法。 The method for producing a purified rosmarinic acid-containing composition according to claim 1 or 2, wherein the amount of activated carbon used is 20 to 100% by mass with respect to the solid content mass of the rosmarinic acid-containing composition.
- 抽出工程の後に、抽出液を濃縮し、次いでエタノール又はエタノール水溶液を添加して生じた沈殿物を除去する精製工程を含む、請求項1~3のいずれか1項記載の精製ロズマリン酸含有組成物の製造方法。 The purified rosmarinic acid-containing composition according to any one of claims 1 to 3, comprising a purification step of concentrating the extract and then adding ethanol or an aqueous ethanol solution to remove the precipitate formed after the extraction step. Manufacturing method.
- シソ科植物がシソ科シソ属の植物である請求項1~4のいずれか1項記載の精製ロズマリン酸含有組成物の製造方法。 The method for producing a purified rosmarinic acid-containing composition according to any one of claims 1 to 4, wherein the Labiatae plant is a plant belonging to the genus Perilla of the Labiatae family.
- シソ科シソ属の植物が赤シソである請求項5記載の精製ロズマリン酸含有組成物の製造方法。 The method for producing a purified rosmarinic acid-containing composition according to claim 5, wherein the plant belonging to the genus Perilla of the Labiatae family is red perilla.
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