WO2024071421A1 - Method for producing 2-o-trans-caffeoylhydroxycitric acid - Google Patents

Method for producing 2-o-trans-caffeoylhydroxycitric acid Download PDF

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WO2024071421A1
WO2024071421A1 PCT/JP2023/035789 JP2023035789W WO2024071421A1 WO 2024071421 A1 WO2024071421 A1 WO 2024071421A1 JP 2023035789 W JP2023035789 W JP 2023035789W WO 2024071421 A1 WO2024071421 A1 WO 2024071421A1
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trans
acid
caffeoylhydroxycitric
coriander
extraction
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PCT/JP2023/035789
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French (fr)
Japanese (ja)
Inventor
剛 池田
圭介 中嶋
七海 吉野
俊介 中村
浩幸 恩田
雅博 葛西
麻里子 小池
卓也 菅原
甲介 西
萌子 石田
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学校法人君が淵学園
ヱスビー食品株式会社
国立大学法人愛媛大学
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Publication of WO2024071421A1 publication Critical patent/WO2024071421A1/en

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids

Definitions

  • the present invention relates to a method for producing 2-O-trans-caffeoyl hydroxycitric acid. According to the present invention, 2-O-trans-caffeoyl hydroxycitric acid can be produced efficiently.
  • Non-Patent Document 1 2-O-trans-caffeoylhydroxycitric acid has been reported to be contained in hibiscus leaves.
  • the present inventors have conducted extensive research into an efficient method for producing 2-O-trans-caffeoyl hydroxycitric acid and have surprisingly found that 2-O-trans-caffeoyl hydroxycitric acid can be efficiently produced by using coriander as a raw material.
  • the present invention is based on these findings.
  • the present invention provides [1] Soaking coriander in a polar solvent;
  • a method for producing 2-O-trans-caffeoyl hydroxycitric acid comprising the step of extracting 2-O-trans-caffeoyl hydroxycitric acid represented by the formula: [2] The method for producing 2-O-trans-caffeoylhydroxycitric acid according to [1], further comprising a heat treatment step of 65°C or higher prior to the extraction step; [3] The method for producing 2-O-trans-caffeoylhydroxycitric acid according to [1] or [2], wherein the extraction step is an extraction step using a polar solvent at 65 ° C or higher; [4] The method for producing 2-O-trans-caffeoylhydroxycitric acid according to any one of [1] to [3], wherein the extraction step is an extraction step using an acidic polar solvent.
  • a method for producing a 2-O-trans-caffeoyl hydroxycitric acid-containing formulation comprising the steps of extracting 2-O-trans-caffeoyl hydroxycitric acid represented by the formula: [12] The method for producing the 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to [11], further comprising a heat treatment step of 65°C or higher prior to the extraction step. [13] The method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to [11] or [12], wherein the extraction step is an extraction step using a polar solvent at 65° C. or higher.
  • 2-O-trans-caffeoyl hydroxycitric acid According to the method for producing 2-O-trans-caffeoyl hydroxycitric acid of the present invention, 2-O-trans-caffeoyl hydroxycitric acid can be produced efficiently.
  • the invention is described by dividing it into various aspects, but the matters, definitions of terms, and embodiments described in each aspect can also be applied to other aspects.
  • the method for producing 2-O-trans-caffeoyl hydroxycitric acid of the present invention comprises soaking coriander in a polar solvent, The method includes a step of extracting 2-O-trans-caffeoylhydroxycitric acid represented by the formula:
  • 2-O-trans-caffeoyl hydroxycitric acid Compound A
  • the 2-O-trans-caffeoylhydroxycitric acid (hereinafter sometimes referred to as compound A) is contained in hibiscus leaves (Non-Patent Document 1).
  • compound A is contained in coriander, and the present inventors have discovered this.
  • the present inventors have confirmed that compound A has an anti-allergic effect.
  • the extraction method in the extraction step of the present invention is a solvent extraction method. It can be carried out according to a known solvent extraction method, except that coriander is used as a raw material and a polar solvent is used as a solvent.
  • coriander Coriander is a member of the Umbelliferae family and is used as a spice. As a spice, the whole plant is used, the fruit and seeds are called coriander seeds, and the leaves and stems are called coriander leaves or cilantro. Compound A is contained in all parts of the coriander plant. Therefore, in the production method of the present invention, the part of coriander used to produce compound A is not particularly limited, and may be the whole plant, stems, leaves, roots, flowers, fruits, or seeds, or a mixture of at least two or more of them, but preferably the aboveground parts of the plant, such as stems, leaves, flowers, fruits, and seeds, and more preferably the leaves.
  • coriander When performing the extraction operation, coriander may be used raw or dried (e.g., freeze-dried). In the extraction operation, it is preferable to process the coriander into a crushed, pulverized, ground, or powdered state so as to improve the extraction efficiency.
  • the extraction solvent used in the extraction step of the present invention is not limited as long as compound A can be extracted into the extraction liquid, but since compound A dissolves in polar solvents, it is preferably a polar solvent.
  • polar solvents include aqueous solvents containing water, polar organic solvents, and mixed solvents containing aqueous solvents or polar organic solvents.
  • the mixed solvent may contain a non-polar solvent as long as it does not excessively inhibit the dissolution of compound A in the polar solvent.
  • the pH of the aqueous solvent is not particularly limited.
  • the aqueous solvent is not limited as long as it contains water, and for example, water, saline, or a buffer solution can be used.
  • the buffer solution include phosphate buffer, sodium phosphate buffer, sodium carbonate buffer, citrate buffer, citrate phosphate buffer, acetate buffer, and Tris buffer.
  • the preferred aqueous solvent is water.
  • Examples of polar organic solvents include alcohols, esters, methylene chloride (dichloromethane), chloroform, diethyl ether, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, acetic acid, and formic acid.
  • Examples of alcohols include monohydric alcohols with 1 to 5 carbon atoms, such as methanol, ethanol, propyl alcohol, isopropyl alcohol, and butyl alcohol, and polyhydric alcohols with 2 to 5 carbon atoms, such as 1,3-butylene glycol, propylene glycol, dipropylene glycol, and glycerin.
  • the temperature of the polar solvent in the extraction step is not particularly limited.
  • the extraction temperature temperature of the polar solvent
  • the extraction step can be carried out at a temperature of, for example, -50°C to 120°C, preferably -10 to 100°C, more preferably 0 to 100°C. Note that "before" the extraction step does not mean immediately before the extraction step, that is, any step may be included between the extraction step and the heat treatment step.
  • the extraction temperature (temperature of the polar solvent) is not limited.
  • the extraction temperature is preferably 65°C or higher, more preferably 70°C or higher, even more preferably 75°C or higher, and even more preferably 80°C or higher.
  • the upper limit is not particularly limited, but is preferably 100°C or lower.
  • the extraction operation is preferably carried out with stirring or shaking to improve the extraction efficiency.
  • the extraction time can be appropriately determined depending on the part used, such as the root, stem, leaf, flower, fruit, or seed.
  • the extraction time can also be appropriately determined depending on the state of the coriander, i.e., whether it is fresh or dried, or the processed state when it is crushed or powdered.
  • the extraction time can also be appropriately determined depending on the extraction conditions, such as the temperature of the extract or the presence or absence of stirring or shaking.
  • the extraction time is usually 1 minute to 72 hours, and preferably 10 minutes to 1 hour.
  • an acidic aqueous solvent may be used, but is not limited thereto.
  • the recovery amount of compound A can be increased by using an acidic aqueous solvent.
  • the pH of the acidic polar solvent is not particularly limited, but is, for example, pH 5 or less, preferably pH 3 or less.
  • the acid for adjusting the polar solvent to an acidic state can be appropriately selected depending on the type of polar solvent, and examples of the acid include formic acid, acetic acid, and citric acid.
  • the extraction temperature (polar solvent temperature) is not limited, and the extraction step can be performed at a temperature of, for example, -50°C to 120°C, but is preferably -10 to 100°C, and more preferably 0 to 100°C. However, even in the case of an acidic polar solvent, the extraction temperature may be 65°C or higher.
  • the extraction operation and extraction time are as described above.
  • the acidic polar solvent may further contain a polar organic solvent.
  • a polar organic solvent for example, a mixture of a polar organic solvent and an aqueous solvent can increase the recovery rate of compound A.
  • polar organic solvents include acetonitrile, alcohol, ester, methylene chloride (dichloromethane), chloroform, diethyl ether, tetrahydrofuran, acetone, N,N-dimethylformamide, and dimethyl sulfoxide.
  • a heat treatment step at 65° C. or higher may be carried out prior to the extraction step, although this is not a limitation.
  • the recovery amount of compound A can be increased by carrying out the heat treatment step.
  • the heat treatment step is not particularly limited as long as heat of 65° C. is applied to the coriander, but is preferably 70° C. or higher, more preferably 75° C. or higher, and even more preferably 80° C. or higher.
  • the upper limit is not particularly limited, but is preferably 100° C. or lower.
  • the time of the heat treatment is not particularly limited as long as the effects of the present invention can be obtained, but is, for example, 10 seconds or more, in one embodiment, 15 seconds or more, in one embodiment, 30 seconds or more, in one embodiment, 1 minute or more, in one embodiment, 2 minutes or more, in one embodiment, 3 minutes or more, in one embodiment, 4 minutes or more, and in one embodiment, 5 minutes or more.
  • the upper limit of the heat treatment time is not particularly limited as long as 2-O-trans-caffeoylhydroxycitric acid is not destroyed by the heat treatment, but is, for example, 72 hours or less, in one embodiment, 1 hour or less, in one embodiment, 30 minutes or less, in one embodiment, 10 minutes or less, in one embodiment, 1 minute or less, in one embodiment, 30 seconds or less, and in one embodiment, 15 seconds or less.
  • the heat treatment temperature and the heat treatment time may be appropriately combined so as to obtain the effects of the present invention, but for example, when the heat treatment temperature is high, the effects of the present invention can be obtained even if the heat treatment time is shortened, and on the other hand, when the heat treatment temperature is low, the effects of the present invention can be obtained by extending the heat treatment time.
  • blanching is one embodiment of hot water treatment and steam treatment.
  • Autoclave treatment is a steam treatment under pressure, and the temperature can be 100°C or higher.
  • blanching means heating the coriander in boiling water at 70 to 100°C for 10 seconds to 1 minute.
  • Coriander extract containing 2-O-trans-caffeoylhydroxycitric acid is prepared by soaking coriander in a polar solvent, The compound is obtained by an extraction method including a step of extracting 2-O-trans-caffeoylhydroxycitric acid represented by the formula:
  • the 2-O-trans-caffeoylhydroxycitric acid contained in the extract of the present invention is that described in the "Production Method” section of the present invention.
  • the extraction step for extracting the extract of the present invention is the extraction step described in the "Production Method” section of the present invention, and the "polar solvent”, “acidic polar solvent”, etc. may be the same, and the extraction time or temperature may be the same.
  • the "heat treatment step” may be performed before the extraction step.
  • the coriander extract may be contained within the container.
  • a method for producing a 2-O-trans-caffeoyl hydroxycitric acid-containing preparation includes a step of formulating the 2-O-trans-caffeoyl hydroxycitric acid extracted in the extraction step.
  • Dosage forms of the preparations include, for example, liquids, tablets (tablets, tablets), capsules (soft capsules, hard capsules), powders (granules, fine granules), solids, semi-liquids, creams, and pastes.
  • known formulation methods such as powder drying, dissolution, gelation, pasting, concentration, filtration, etc., can be used alone or in combination.
  • composition containing dried, crushed, ground, or powdered coriander One aspect of the present invention is a composition containing dried, crushed, ground, or powdered coriander, which is used to extract 2-O-trans-caffeoylhydroxycitric acid.
  • the composition may contain only dried, crushed, ground, or powdered coriander, or may contain any other element (e.g., a desiccant, other spices, etc.).
  • the crushed, crushed, ground, or powdered coriander may be dried.
  • the composition may be contained in any container.
  • 2-O-trans-caffeoyl hydroxycitric acid (compound A) can be efficiently produced (extracted or recovered) because coriander contains a large amount of compound A.
  • the present inventors have found that coriander contains a large amount of compound A, and therefore, 2-O-trans-caffeoyl hydroxycitric acid (compound A) can be efficiently produced by the present invention.
  • the mechanism by which the compound A can be produced in a larger amount by the production method of the present invention has not been completely elucidated, but can be presumed as follows.
  • the present invention is not limited to the following presumption.
  • the compound A contained in coriander is decomposed in a certain amount in the extraction process by the decomposition enzyme contained in coriander, resulting in a decrease in the yield. It is believed that this decomposition enzyme can be inactivated by, but is not limited to, heat or acid. Therefore, it is presumed that the decomposition enzyme is inactivated and the recovery rate of compound A is increased by using a "polar solvent of 65°C or higher” or an “acidic polar solvent” in the "heat treatment process" or extraction process of the present invention.
  • compound A was produced by carrying out a heat treatment step and using water (Example 1) or hot water (Example 2) as the polar solvent.
  • Fresh coriander leaves, stems and roots were blanched in hot water at 80°C for 20 seconds, drained and frozen at -40°C.
  • the frozen coriander leaves, stems and roots were freeze-dried for 48 hours.
  • the freeze-dried product was pulverized in a hammer mill and sieved through a 48 mesh. 1 g of the pulverized product was placed in a test tube, 5 to 20 mL of water or hot water (100°C) was added, and the mixture was left to stand in an ultrasonic cleaner for 60 minutes.
  • the sample was centrifuged (2000 rpm, 20 minutes), and the supernatant was filtered through filter paper to recover the extract. Water or hot water (100°C) was added again to the centrifuged residue, and the mixture was left to stand in an ultrasonic cleaner for 60 minutes. This extraction operation was repeated four times to obtain an extract.
  • the amount of Compound A was quantified by HPLC. The results are shown in Table 1. The content of Compound A was shown as % by weight based on the pulverized dried raw material.
  • compound A was produced by changing the time of the heat treatment step. Fresh coriander leaves were blanched in hot water at 90°C for 0 seconds (Example 3), 30 seconds (Example 4), or 60 seconds (Example 5), and then the hot water was drained and frozen at -40°C. The frozen coriander leaves were freeze-dried for 72 hours. The freeze-dried product was pulverized in a coffee mill. 1 g of the pulverized product was placed in a test tube, 5-20 mL of hot water (100°C) was added, and the tube was left to stand in an ultrasonic cleaner for 60 minutes.
  • the sample was centrifuged (2000 rpm, 20 minutes), and the supernatant was filtered through filter paper to recover the extract.
  • Hot water (100°C) was added again to the centrifuged residue, and the tube was left to stand in an ultrasonic cleaner for 60 minutes. This extraction procedure was repeated four times to obtain an extract.
  • the amount of Compound A was quantified by HPLC. The results are shown in Table 2. The content of Compound A was shown as % by weight based on the weight of the ground dry raw material.
  • Examples 6 to 8 In this example, compound A was produced without carrying out a heat treatment step. Fresh coriander leaves and stems were ground in a mortar. 3.97 g of the ground product was placed in a test tube (50 mL capacity), 40 mL of hot water (100°C) was added, and the mixture was shaken for 30 minutes using a shaker. The sample was centrifuged (3500 rpm, 5 minutes), and 5 mL of the supernatant was left to stand in a refrigerator for 3 hours (Example 6), at 40°C for 3 hours (Example 7), or at room temperature for 2 hours (Example 8). The sample was centrifuged (11000 rpm, 1 minute) and filtered through a 0.45 ⁇ m filter. Compound A was quantified by HPLC. The results are shown in Table 3. The content of Compound A is shown as weight % based on the ground raw material.
  • the heat treatment step was carried out in an autoclave.
  • Fresh coriander leaves and stems were frozen at -40°C.
  • the frozen coriander leaves and stems were freeze-dried for 72 hours.
  • the resulting freeze-dried product was pulverized in a blender.
  • the pulverized product was sterilized in an autoclave (121°C, 2 atm, 20 min).
  • 0.2 g of the resulting pulverized product was placed in a test tube, 5 mL of hot water (100°C) (Example 9) or water (Example 10) was added, and the mixture was shaken for 20 minutes.
  • the sample was centrifuged (3000 rpm, 5 min) and the supernatant was collected.
  • compound A was produced using an acidic polar solvent. Fresh coriander leaves and stems were frozen at -40°C. The frozen coriander leaves and stems were freeze-dried for 72 hours. The resulting freeze-dried product was pulverized in a blender.
  • Example 11 hot water (100°C) (Example 11), hot water (100°C) containing 0.5% formic acid (Example 12), water containing 0.5% formic acid (Example 13), or water containing 0.5% formic acid and 50% acetonitrile (ACN) (Example 14) was added, and the mixture was left to stand for 10 minutes in a water bath (95°C, Examples 11 and 12) or at room temperature (Examples 13 and 14). The mixture was then shaken for 20 minutes. The sample was centrifuged (3000 rpm, 5 minutes) and the supernatant was collected.
  • ACN acetonitrile
  • Examples 15 to 16 compound A was produced using a mixed solvent of water and a polar organic solvent. Fresh coriander leaves and stems were frozen at -40°C. The frozen coriander leaves and stems were freeze-dried for 72 hours. The freeze-dried product was pulverized in a blender. 0.1 g of the pulverized product was placed in a test tube, and 5 ml of water containing 50% acetonitrile (Example 15) or water containing 50% ethanol (Example 16) was added, and the mixture was left to stand at room temperature for 10 minutes. The mixture was then shaken for 20 minutes. The sample was centrifuged (3000 rpm, 5 minutes) and the supernatant was collected.
  • Examples 17 to 19 In this example, compound A was produced without carrying out a heat treatment step, and the temperature of the extraction solvent was set to 70°C to 90°C. Fresh coriander leaves and stems were frozen at -40°C. The frozen coriander leaves and stems were freeze-dried for 72 hours. The freeze-dried product was pulverized in a blender. 0.1 g of the pulverized product was placed in a test tube, 5 mL of hot water (Example 17: 70°C, Example 18: 80°C, Example 19: 90°C) was added, and the tube was left to stand in a water bath at the same temperature as the added hot water for 10 minutes. The tube was then shaken for 20 minutes.
  • the sample was centrifuged (3000 rpm, 5 minutes) and the supernatant was collected.
  • the extract was centrifuged (11000 rpm, 1 minute) and filtered through a 0.45 ⁇ m filter.
  • Compound A was quantified by HPLC. The results are shown in Table 7. The content of Compound A was shown as % by weight based on the pulverized dry raw material.
  • the manufacturing method of the present invention can be used to produce 2-O-trans-caffeoylhydroxycitric acid.

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Abstract

Provided is a method for producing 2-O-trans-caffeoylhydroxycitric acid, the method including a step in which coriander is immersed in a polar solvent to extract 2-O-trans-caffeoylhydroxycitric acid with the polar solvent.

Description

２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法Method for producing 2-O-trans-caffeoylhydroxycitric acid
　本発明は、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法に関する。本発明によれば、効率的に２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を製造することができる。 The present invention relates to a method for producing 2-O-trans-caffeoyl hydroxycitric acid. According to the present invention, 2-O-trans-caffeoyl hydroxycitric acid can be produced efficiently.
　２－Ｏ－トランス－カフェオイルヒドロキシクエン酸はハイビスカスの葉に含まれていることが報告されている（非特許文献１）。 2-O-trans-caffeoylhydroxycitric acid has been reported to be contained in hibiscus leaves (Non-Patent Document 1).
　しかしながら、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を効率的に製造する方法は、知られていなかった。
　従って、本発明の目的は、効率的な２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法を提供することである。 However, no method for efficiently producing 2-O-trans-caffeoylhydroxycitric acid has been known.
It is therefore an object of the present invention to provide an efficient process for producing 2-O-trans-caffeoylhydroxycitric acid.
　本発明者は、効率的な２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法について、鋭意研究した結果、驚くべきことに、コリアンダーを原料とすることによって、効率的に２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を製造できることを見出した。
　本発明は、こうした知見に基づくものである。
　従って、本発明は、
［１］コリアンダーを極性溶媒に浸漬し、
Figure JPOXMLDOC01-appb-C000004
 で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程を含む、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法、
［２］前記抽出工程の前に、６５℃以上の熱処理工程をさらに含む、［１］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法、
［３］前記抽出工程が、６５℃以上の極性溶媒による抽出工程である、［１］又は［２］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法、
［４］前記抽出工程が、酸性極性溶媒による抽出工程である、［１］～［３］のいずれかに記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法、
［５］前記熱処理工程がブランチングである、［２］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法、
［６］コリアンダーを極性溶媒に浸漬し、
Figure JPOXMLDOC01-appb-C000005
 で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程を含む抽出方法によって得られる、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物、
［７］前記抽出工程の前に、６５℃以上の熱処理工程をさらに含む、［６］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物、
［８］前記抽出工程が、６５℃以上の水性溶媒による抽出工程である、［６］又は［７］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物、
［９］前記抽出工程が、酸性極性溶媒による抽出工程である、［６］～［８］のいずれかに記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物、
［１０］前記熱処理工程がブランチングである、［７］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物、
［１１］コリアンダーを極性溶媒に浸漬し、
Figure JPOXMLDOC01-appb-C000006
 で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程と
抽出された２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を製剤化する工程と
を含む、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法、
［１２］前記抽出工程の前に、６５℃以上の熱処理工程をさらに含む、［１１］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法、
［１３］前記抽出工程が、６５℃以上の極性溶媒による抽出工程である、［１１］又は［１２］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法、
［１４］前記抽出工程が、酸性極性溶媒による抽出工程である、［１１］～［１３］のいずれかに記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法、
［１５］前記熱処理工程がブランチングである、［１２］に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法、及び
［１６］コリアンダーの、乾燥物、破砕物、粉砕物、摩砕物又は粉体を含む組成物であって、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を抽出するために用いられる組成物。
に関する。 The present inventors have conducted extensive research into an efficient method for producing 2-O-trans-caffeoyl hydroxycitric acid and have surprisingly found that 2-O-trans-caffeoyl hydroxycitric acid can be efficiently produced by using coriander as a raw material.
The present invention is based on these findings.
Thus, the present invention provides
[1] Soaking coriander in a polar solvent;
Figure JPOXMLDOC01-appb-C000004
 A method for producing 2-O-trans-caffeoyl hydroxycitric acid, comprising the step of extracting 2-O-trans-caffeoyl hydroxycitric acid represented by the formula:
[2] The method for producing 2-O-trans-caffeoylhydroxycitric acid according to [1], further comprising a heat treatment step of 65°C or higher prior to the extraction step;
[3] The method for producing 2-O-trans-caffeoylhydroxycitric acid according to [1] or [2], wherein the extraction step is an extraction step using a polar solvent at 65 ° C or higher;
[4] The method for producing 2-O-trans-caffeoylhydroxycitric acid according to any one of [1] to [3], wherein the extraction step is an extraction step using an acidic polar solvent.
[5] The method for producing 2-O-trans-caffeoylhydroxycitric acid according to [2], wherein the heat treatment step is blanching.
[6] Soaking coriander in a polar solvent;
Figure JPOXMLDOC01-appb-C000005
 A coriander extract containing 2-O-trans-caffeoyl hydroxycitric acid, which is obtained by an extraction method including a step of extracting 2-O-trans-caffeoyl hydroxycitric acid represented by the formula:
[7] The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid according to [6], further comprising a heat treatment step of 65°C or higher prior to the extraction step.
[8] The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid according to [6] or [7], wherein the extraction step is an extraction step using an aqueous solvent at 65°C or higher.
[9] The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid according to any one of [6] to [8], wherein the extraction step is an extraction step using an acidic polar solvent.
[10] The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid according to [7], wherein the heat treatment step is blanching.
[11] Soaking coriander in a polar solvent;
Figure JPOXMLDOC01-appb-C000006
 A method for producing a 2-O-trans-caffeoyl hydroxycitric acid-containing formulation, comprising the steps of extracting 2-O-trans-caffeoyl hydroxycitric acid represented by the formula:
[12] The method for producing the 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to [11], further comprising a heat treatment step of 65°C or higher prior to the extraction step.
[13] The method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to [11] or [12], wherein the extraction step is an extraction step using a polar solvent at 65° C. or higher.
[14] The method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to any one of [11] to [13], wherein the extraction step is an extraction step using an acidic polar solvent.
[15] The method for producing a 2-O-trans-caffeoyl hydroxycitric acid-containing preparation according to [12], wherein the heat treatment step is blanching; and [16] a composition comprising dried, crushed, pulverized, ground or powdered coriander, the composition being used for extracting 2-O-trans-caffeoyl hydroxycitric acid.
Regarding.
　本発明の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法によれば、効率的に２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を製造することができる。
　本明細書においては、発明をそれぞれの態様（aspect）に分けて説明をしているが、それぞれの態様に記載の事項、語句の定義、及び実施形態は、他の態様においても適用可能である。 According to the method for producing 2-O-trans-caffeoyl hydroxycitric acid of the present invention, 2-O-trans-caffeoyl hydroxycitric acid can be produced efficiently.
In this specification, the invention is described by dividing it into various aspects, but the matters, definitions of terms, and embodiments described in each aspect can also be applied to other aspects.
［１］２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法
　本発明の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法は、コリアンダーを極性溶媒に浸漬し、
Figure JPOXMLDOC01-appb-C000007
 で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程を含む。 [1] Method for Producing 2-O-trans-Caffeoyl Hydroxycitric Acid The method for producing 2-O-trans-caffeoyl hydroxycitric acid of the present invention comprises soaking coriander in a polar solvent,
Figure JPOXMLDOC01-appb-C000007
 The method includes a step of extracting 2-O-trans-caffeoylhydroxycitric acid represented by the formula:
《２－Ｏ－トランス－カフェオイルヒドロキシクエン酸：化合物Ａ》
　前記２－Ｏ－トランス－カフェオイルヒドロキシクエン酸（以下、化合物Ａと称することがある）は、ハイビスカスの葉に含まれている（非特許文献１）。しかしながら、化合物Ａがコリアンダーに含まれていることは報告されておらず、本発明者らが見出したものである。なお、本発明者らは、化合物Ａが抗アレルギー作用を有することを確認した。 2-O-trans-caffeoyl hydroxycitric acid: Compound A
The 2-O-trans-caffeoylhydroxycitric acid (hereinafter sometimes referred to as compound A) is contained in hibiscus leaves (Non-Patent Document 1). However, it has not been reported that compound A is contained in coriander, and the present inventors have discovered this. The present inventors have confirmed that compound A has an anti-allergic effect.
《抽出工程》
　本発明における抽出工程における抽出法は溶剤抽出法である。原料としてコリアンダーを用い、溶剤として極性溶媒を用いる以外は、公知の溶剤抽出法に従って実施することができる。 Extraction process
The extraction method in the extraction step of the present invention is a solvent extraction method. It can be carried out according to a known solvent extraction method, except that coriander is used as a raw material and a polar solvent is used as a solvent.
《コリアンダー》
　コリアンダーは、セリ科の一種であり香辛料として使用される。香辛料としては、植物全体を使用されたり、果実や種子部分をコリアンダーシードと称して使用されたり、葉や茎の部分をコリアンダーリーフやパクチーと称して使用されたりする。
　化合物Ａはコリアンダーの植物体のすべての部位に含まれている。従って、本発明の製造方法において、化合物Ａを製造するために用いるコリアンダーの部位は、特に限定されるものではなく、植物体全体、茎、葉、根、花、果実、若しくは種子、又はそれらの少なくとも２種以上の混合物を挙げることができるが、好ましくは茎、葉、花、果実、種子の植物体の地上に出ている部分であり、さらに好ましくは葉である。コリアンダーは抽出操作を行う際に、生のまま用いてもよく、乾燥（例えば、凍結乾燥）させたものを用いてもよい。抽出操作は、抽出効率が向上するように、破砕物、粉砕物、摩砕物又は粉体等の状態に加工することが好ましい。 "coriander"
Coriander is a member of the Umbelliferae family and is used as a spice. As a spice, the whole plant is used, the fruit and seeds are called coriander seeds, and the leaves and stems are called coriander leaves or cilantro.
Compound A is contained in all parts of the coriander plant. Therefore, in the production method of the present invention, the part of coriander used to produce compound A is not particularly limited, and may be the whole plant, stems, leaves, roots, flowers, fruits, or seeds, or a mixture of at least two or more of them, but preferably the aboveground parts of the plant, such as stems, leaves, flowers, fruits, and seeds, and more preferably the leaves. When performing the extraction operation, coriander may be used raw or dried (e.g., freeze-dried). In the extraction operation, it is preferable to process the coriander into a crushed, pulverized, ground, or powdered state so as to improve the extraction efficiency.
《極性溶媒》
　本発明の抽出工程で用いられる抽出溶媒は、抽出液中に化合物Ａが抽出されることができる限りにおいては限定されるものではないが、化合物Ａは極性溶媒に溶解するため、好ましくは極性溶媒である。極性溶媒としては、水を含む水性溶媒、極性有機溶媒、又は水性溶媒若しくは極性有機溶媒を含む混合溶媒が挙げられる。極性溶媒への化合物Ａの溶解を、極度に阻害しない限りにおいて、混合溶媒に無極性溶媒が含まれてもよい。また、前記水性溶媒のｐＨは、特に制限されない。 Polar Solvents
The extraction solvent used in the extraction step of the present invention is not limited as long as compound A can be extracted into the extraction liquid, but since compound A dissolves in polar solvents, it is preferably a polar solvent. Examples of polar solvents include aqueous solvents containing water, polar organic solvents, and mixed solvents containing aqueous solvents or polar organic solvents. The mixed solvent may contain a non-polar solvent as long as it does not excessively inhibit the dissolution of compound A in the polar solvent. In addition, the pH of the aqueous solvent is not particularly limited.
　水性溶媒としては、水を含んでいる限りにおいて限定されるものではなく、例えば水、生理食塩水、又は緩衝液などを使用することができる。緩衝液としては、リン酸緩衝液、リン酸ナトリウム緩衝液、炭酸ナトリウム緩衝液、クエン酸緩衝液、クエン酸リン酸緩衝液、酢酸緩衝液、及びトリス緩衝液などが挙げられる。好ましい水性溶媒は、水である。 The aqueous solvent is not limited as long as it contains water, and for example, water, saline, or a buffer solution can be used. Examples of the buffer solution include phosphate buffer, sodium phosphate buffer, sodium carbonate buffer, citrate buffer, citrate phosphate buffer, acetate buffer, and Tris buffer. The preferred aqueous solvent is water.
　極性有機溶媒としては、例えばアルコール、エステル、塩化メチレン（ジクロロメタン）、クロロホルム、ジエチルエーテル、テトラヒドロフラン、アセトン、アセトニトリル、Ｎ，Ｎ－ジメチルホルムアミド、ジメチルスルホキシド、酢酸、又はギ酸、が挙げられる。アルコールとしては、例えば、メタノール、エタノール、プロピルアルコール、イソプロピルアルコール、及びブチルアルコール等の炭素数１～５の一価アルコール、１，３－ブチレングリコール、プロピレングリコール、ジプロピレングリコール、及びグリセリン等の炭素数２～５の多価アルコールが挙げられる。 Examples of polar organic solvents include alcohols, esters, methylene chloride (dichloromethane), chloroform, diethyl ether, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, acetic acid, and formic acid. Examples of alcohols include monohydric alcohols with 1 to 5 carbon atoms, such as methanol, ethanol, propyl alcohol, isopropyl alcohol, and butyl alcohol, and polyhydric alcohols with 2 to 5 carbon atoms, such as 1,3-butylene glycol, propylene glycol, dipropylene glycol, and glycerin.
（抽出温度）
　抽出工程における極性溶媒の温度は特に限定されない。特に、抽出工程の前に後述の「熱処理工程」を実施した場合、抽出の温度（極性溶媒の温度）は、限定されるものではなく、例えば－５０℃～１２０℃の温度で、抽出工程を実施することができるが、好ましくは、－１０～１００℃であり、より好ましくは０～１００℃である。
　なお、抽出工程の「前に」とは、直前であることを意味しない。すなわち、抽出工程と熱処理工程との間に任意の工程が含まれてもよい。 (Extraction temperature)
The temperature of the polar solvent in the extraction step is not particularly limited. In particular, when the "heat treatment step" described below is carried out before the extraction step, the extraction temperature (temperature of the polar solvent) is not limited, and the extraction step can be carried out at a temperature of, for example, -50°C to 120°C, preferably -10 to 100°C, more preferably 0 to 100°C.
Note that "before" the extraction step does not mean immediately before the extraction step, that is, any step may be included between the extraction step and the heat treatment step.
　抽出工程の前に後述の「熱処理工程」を実施しない場合も、抽出の温度（極性溶媒の温度）は限定されるものではない。しかしながら、この場合、抽出の温度（極性溶媒の温度）は、好ましくは６５℃以上であり、より好ましくは７０℃以上であり、更に好ましくは７５℃以上であり、更に好ましくは８０℃以上である。上限は、特に限定されないが、好ましくは１００℃以下である。 Even if the "heat treatment step" described below is not carried out before the extraction step, the extraction temperature (temperature of the polar solvent) is not limited. However, in this case, the extraction temperature (temperature of the polar solvent) is preferably 65°C or higher, more preferably 70°C or higher, even more preferably 75°C or higher, and even more preferably 80°C or higher. The upper limit is not particularly limited, but is preferably 100°C or lower.
　また、抽出操作は、抽出効率が向上するように、撹拌又は振盪しながら実施することが好ましい。抽出時間は、例えば、根、茎、葉、花、果実、又は種子などの使用部分に応じて適宜決定することができる。また、抽出時間は、コリアンダーの状態、すなわち、生若しくは乾燥物であるか、又は破砕物若しくは粉体の状態に加工した場合にはその加工状態に応じて適宜決定することができる。さらに、抽出時間は、抽出液の温度、又は撹拌若しくは振盪の有無などの抽出条件に応じて、適宜決定することができる。抽出時間は、通常、１分～７２時間であり、１０分～１時間であることが好ましい。 The extraction operation is preferably carried out with stirring or shaking to improve the extraction efficiency. The extraction time can be appropriately determined depending on the part used, such as the root, stem, leaf, flower, fruit, or seed. The extraction time can also be appropriately determined depending on the state of the coriander, i.e., whether it is fresh or dried, or the processed state when it is crushed or powdered. The extraction time can also be appropriately determined depending on the extraction conditions, such as the temperature of the extract or the presence or absence of stirring or shaking. The extraction time is usually 1 minute to 72 hours, and preferably 10 minutes to 1 hour.
《酸性極性溶媒》
　本発明の抽出工程においては、限定されるものではないが、酸性水性溶媒を用いてもよい。特に、抽出工程の前に後述の「熱処理工程」を実施しない場合は、酸性水性溶媒を用いることにより、化合物Ａの回収量を増加させることができる。酸性極性溶媒のｐＨは、特に限定されるものではないが、例えばｐＨ５以下であり、好ましくはｐＨ３以下である。極性溶媒を酸性に調整するための、酸としては、極性溶媒に種類に応じて、適宜選択することができるが、例えばギ酸、酢酸、クエン酸が挙げられる。酸性極性溶媒を用いる場合の、抽出の温度（極性溶媒の温度）は、限定されるものではなく、例えば－５０℃～１２０℃の温度で、抽出工程を実施することができるが、好ましくは、－１０～１００℃であり、より好ましくは０～１００℃である。しかしながら、酸性極性溶媒の場合も、抽出温度は、６５℃以上としてもよい。また、抽出操作及び抽出時間は、前記の通りである。 《Acidic polar solvent》
In the extraction step of the present invention, an acidic aqueous solvent may be used, but is not limited thereto. In particular, when the "heat treatment step" described below is not performed before the extraction step, the recovery amount of compound A can be increased by using an acidic aqueous solvent. The pH of the acidic polar solvent is not particularly limited, but is, for example, pH 5 or less, preferably pH 3 or less. The acid for adjusting the polar solvent to an acidic state can be appropriately selected depending on the type of polar solvent, and examples of the acid include formic acid, acetic acid, and citric acid. When an acidic polar solvent is used, the extraction temperature (polar solvent temperature) is not limited, and the extraction step can be performed at a temperature of, for example, -50°C to 120°C, but is preferably -10 to 100°C, and more preferably 0 to 100°C. However, even in the case of an acidic polar solvent, the extraction temperature may be 65°C or higher. The extraction operation and extraction time are as described above.
　酸性極性溶媒は、更に極性有機溶媒を含んでもよい。例えば、極性有機溶媒と水性溶媒との混合溶媒によって、化合物Ａの回収率を増加させることができる。極性有機溶媒としては、アセトニトリル、アルコール、エステル、塩化メチレン（ジクロロメタン）、クロロホルム、ジエチルエーテル、テトラヒドロフラン、アセトン、Ｎ，Ｎ－ジメチルホルムアミド、又はジメチルスルホキシドが挙げられる。 The acidic polar solvent may further contain a polar organic solvent. For example, a mixture of a polar organic solvent and an aqueous solvent can increase the recovery rate of compound A. Examples of polar organic solvents include acetonitrile, alcohol, ester, methylene chloride (dichloromethane), chloroform, diethyl ether, tetrahydrofuran, acetone, N,N-dimethylformamide, and dimethyl sulfoxide.
《熱処理工程》
　本発明の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法においては、限定されるものではないが、前記抽出工程の前に、６５℃以上の熱処理工程を行ってもよい。特に、前記抽出工程において、６５℃未満の極性溶媒を用いて抽出操作を行う場合、又は酸性極性溶媒を用いない場合においては、熱処理工程を実施することによって、化合物Ａの回収量を増加させることができる。 <Heat treatment process>
In the method for producing 2-O-trans-caffeoylhydroxycitric acid of the present invention, a heat treatment step at 65° C. or higher may be carried out prior to the extraction step, although this is not a limitation. In particular, when the extraction step is carried out using a polar solvent at a temperature of less than 65° C. or when no acidic polar solvent is used, the recovery amount of compound A can be increased by carrying out the heat treatment step.
　熱処理工程としては、コリアンダーに６５℃の熱が印加される限りにおいて、特に限定されるものではないが、好ましくは７０℃以上であり、より好ましくは７５℃以上であり、更に好ましくは８０℃以上である。上限は、特に限定されないが、１００℃以下が好ましい。
　熱処理の時間は、本発明の効果が得られる限りにおいて、特に限定されるものではないが、例えば１０秒以上であり、ある態様では１５秒以上であり、ある態様では３０秒以上であり、ある態様では１分以上であり、ある態様では２分以上であり、ある態様では３分以上であり、ある態様では４分以上であり、ある態様では５分以上である。熱処理の時間の上限は、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸が熱処理によって破壊されない限りにおいて特に限定されるものではなく、例えば７２時間以下であり、ある態様では１時間以下であり、ある態様では３０分以下であり、ある態様では１０分以下であり、ある態様では１分以下であり、ある態様では３０秒以下であり、ある態様では１５秒以下である。熱処理温度と、熱処理時間は、本発明の効果が得られるように、適宜組み合わせて行えばよいが、例えば熱処理温度が高い場合は、熱処理時間を短くしても本発明の効果を得ることが可能であり、一方熱処理温度が低い場合は、熱処理時間を長くすることによって本発明の効果を得ることが可能である。 The heat treatment step is not particularly limited as long as heat of 65° C. is applied to the coriander, but is preferably 70° C. or higher, more preferably 75° C. or higher, and even more preferably 80° C. or higher. The upper limit is not particularly limited, but is preferably 100° C. or lower.
The time of the heat treatment is not particularly limited as long as the effects of the present invention can be obtained, but is, for example, 10 seconds or more, in one embodiment, 15 seconds or more, in one embodiment, 30 seconds or more, in one embodiment, 1 minute or more, in one embodiment, 2 minutes or more, in one embodiment, 3 minutes or more, in one embodiment, 4 minutes or more, and in one embodiment, 5 minutes or more. The upper limit of the heat treatment time is not particularly limited as long as 2-O-trans-caffeoylhydroxycitric acid is not destroyed by the heat treatment, but is, for example, 72 hours or less, in one embodiment, 1 hour or less, in one embodiment, 30 minutes or less, in one embodiment, 10 minutes or less, in one embodiment, 1 minute or less, in one embodiment, 30 seconds or less, and in one embodiment, 15 seconds or less. The heat treatment temperature and the heat treatment time may be appropriately combined so as to obtain the effects of the present invention, but for example, when the heat treatment temperature is high, the effects of the present invention can be obtained even if the heat treatment time is shortened, and on the other hand, when the heat treatment temperature is low, the effects of the present invention can be obtained by extending the heat treatment time.
　具体的な熱処理方法として、熱水処理、蒸気処理、熱風処理、オートクレーブ処理などが挙げられる。例えば、熱水処理及び蒸気処理の１つの実施態様として、ブランチングが挙げられる。また、オートクレーブ処理は、加圧下での蒸気処理であり、温度を１００℃以上にすることができる。本明細書において、「ブランチング」とは、コリアンダーを７０～１００℃の熱湯により、１０秒～１分加熱することを意味する。 Specific heat treatment methods include hot water treatment, steam treatment, hot air treatment, autoclave treatment, etc. For example, blanching is one embodiment of hot water treatment and steam treatment. Autoclave treatment is a steam treatment under pressure, and the temperature can be 100°C or higher. In this specification, "blanching" means heating the coriander in boiling water at 70 to 100°C for 10 seconds to 1 minute.
［２］２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むパクチー抽出物
　本発明のパクチー抽出物は、パクチーを極性溶媒に浸漬し、
Figure JPOXMLDOC01-appb-C000008
 で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程を含む抽出方法によって得られる。 [2] Coriander extract containing 2-O-trans-caffeoylhydroxycitric acid The coriander extract of the present invention is prepared by soaking coriander in a polar solvent,
Figure JPOXMLDOC01-appb-C000008
 The compound is obtained by an extraction method including a step of extracting 2-O-trans-caffeoylhydroxycitric acid represented by the formula:
　本発明の抽出物に含まれる２－Ｏ－トランス－カフェオイルヒドロキシクエン酸は、前記本発明の「製造方法」の項に記載のものである。
　本発明の抽出物を抽出するための抽出工程は、前記本発明の「製造方法」の項に記載の抽出工程であり、「極性溶媒」、「酸性極性溶媒」等は同様の物を使用することができ、抽出時間又は抽出温度も、同様に実施することができる。また、本発明の抽出物を抽出するために、抽出工程の前に、前記「熱処理工程」を行ってもよい。
　パクチー抽出物は、容器の中に含まれていてもよい。 The 2-O-trans-caffeoylhydroxycitric acid contained in the extract of the present invention is that described in the "Production Method" section of the present invention.
The extraction step for extracting the extract of the present invention is the extraction step described in the "Production Method" section of the present invention, and the "polar solvent", "acidic polar solvent", etc. may be the same, and the extraction time or temperature may be the same. In addition, in order to extract the extract of the present invention, the "heat treatment step" may be performed before the extraction step.
The coriander extract may be contained within the container.
［３］２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法
　本発明の一態様である２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法は、抽出工程において抽出した２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を製剤化する工程を含む。 [3] Method for producing a 2-O-trans-caffeoyl hydroxycitric acid-containing preparation A method for producing a 2-O-trans-caffeoyl hydroxycitric acid-containing preparation, which is one embodiment of the present invention, includes a step of formulating the 2-O-trans-caffeoyl hydroxycitric acid extracted in the extraction step.
　製剤の剤形としては、例えば、液剤、錠剤（錠剤、タブレット）、カプセル（ソフトカプセル剤、ハードカプセル剤）、粉末（顆粒、細粒）、固形、半液体、クリーム、ペーストが挙げられる。 Dosage forms of the preparations include, for example, liquids, tablets (tablets, tablets), capsules (soft capsules, hard capsules), powders (granules, fine granules), solids, semi-liquids, creams, and pastes.
　製剤化としては、公知の製剤化方法、例えば、粉末乾燥、溶解、ゲル化、ペースト化、濃縮、濾過などの手法を単独で又は組み合わせて用いることができる。 For formulation, known formulation methods, such as powder drying, dissolution, gelation, pasting, concentration, filtration, etc., can be used alone or in combination.
［４］コリアンダーの、乾燥物、破砕物、粉砕物、摩砕物又は粉体を含む組成物
　本発明の一態様は、コリアンダーの、乾燥物、破砕物、粉砕物、摩砕物又は粉体を含む組成物であって、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を抽出するために用いられる組成物である。組成物は、コリアンダーの、乾燥物、破砕物、粉砕物、摩砕物又は粉体のみが含んでもよく、任意の他の要素（例えば、乾燥剤、他のスパイスなど）を含んでもよい。破砕物、粉砕物、摩砕物又は粉体は、乾燥されたものであってもよい。組成物は、任意の容器の中に含まれていてもよい。 [4] Composition containing dried, crushed, ground, or powdered coriander One aspect of the present invention is a composition containing dried, crushed, ground, or powdered coriander, which is used to extract 2-O-trans-caffeoylhydroxycitric acid. The composition may contain only dried, crushed, ground, or powdered coriander, or may contain any other element (e.g., a desiccant, other spices, etc.). The crushed, crushed, ground, or powdered coriander may be dried. The composition may be contained in any container.
《作用》
　本発明の製造方法において、効率的に２－Ｏ－トランス－カフェオイルヒドロキシクエン酸（化合物Ａ）を製造（抽出又は回収）できるのは、コリアンダーに大量の化合物Ａが含まれているからである。本発明者らは、コリアンダーに大量の化合物Ａが含まれていることを見出したことより、本発明により効率的に２－Ｏ－トランス－カフェオイルヒドロキシクエン酸（化合物Ａ）を製造できるものである。
　一方、本発明の製造方法により、より大量に化合物Ａが製造できる機構は、完全に解明されたわけではないが、以下のように推定することができる。しかし、本発明は以下の推定によって限定されるものではない。
　コリアンダーに含まれている化合物Ａは、コリアンダーに含まれる分解酵素によって、抽出工程において一定量の化合物Ａが分解され収率が低下するのではないかと考えられる。この分解酵素は、限定されるものではないが、熱又は酸によって不活化することができると考えられる。従って、本発明の「熱処理工程」、又は抽出工程において「６５℃以上の極性溶媒」を用いること、又は「酸性極性溶媒」を用いることによって、分解酵素が不活化され、化合物Ａの回収率が増加するものと推定される。 Action
In the production method of the present invention, 2-O-trans-caffeoyl hydroxycitric acid (compound A) can be efficiently produced (extracted or recovered) because coriander contains a large amount of compound A. The present inventors have found that coriander contains a large amount of compound A, and therefore, 2-O-trans-caffeoyl hydroxycitric acid (compound A) can be efficiently produced by the present invention.
On the other hand, the mechanism by which the compound A can be produced in a larger amount by the production method of the present invention has not been completely elucidated, but can be presumed as follows. However, the present invention is not limited to the following presumption.
It is believed that the compound A contained in coriander is decomposed in a certain amount in the extraction process by the decomposition enzyme contained in coriander, resulting in a decrease in the yield. It is believed that this decomposition enzyme can be inactivated by, but is not limited to, heat or acid. Therefore, it is presumed that the decomposition enzyme is inactivated and the recovery rate of compound A is increased by using a "polar solvent of 65°C or higher" or an "acidic polar solvent" in the "heat treatment process" or extraction process of the present invention.
　以下、実施例によって本発明を具体的に説明するが、これらは本発明の範囲を限定するものではない。 The present invention will be explained in detail below with reference to examples, but these are not intended to limit the scope of the present invention.
《実施例１及び２》
　本実施例では、熱処理工程を行い、極性溶媒として水（実施例１）、又は熱水（実施例２）を用いて、化合物Ａを製造した。
　生鮮パクチーの葉、茎及び根を、８０℃の熱水で、２０秒間ブランチングし、湯を切って－４０℃で冷凍した。凍結したパクチーの葉、茎及び根を４８時間凍結乾燥した。得られた凍結乾燥物をハンマーミルで粉砕し、４８メッシュで篩分した。得られた粉砕物１ｇを試験管に入れ、５～２０ｍＬの水又は熱水（１００℃）を添加し、超音波洗浄機内で６０分間静置した。サンプルを遠心分離（２０００ｒｐｍ、２０分間）し、上清を濾紙でろ過し、抽出液を回収した。遠心分離した残渣に、再度、水または熱水（１００℃）を加え、超音波洗浄機内で６０分間静置した。この抽出操作を４回繰り返し、抽出物を得た。
　ＨＰＬＣにより化合物Ａを定量した。結果を表１に示す。なお、化合物Ａの含量は、乾燥原料の粉砕物に対する重量％で示した。 Examples 1 and 2
In this example, compound A was produced by carrying out a heat treatment step and using water (Example 1) or hot water (Example 2) as the polar solvent.
Fresh coriander leaves, stems and roots were blanched in hot water at 80°C for 20 seconds, drained and frozen at -40°C. The frozen coriander leaves, stems and roots were freeze-dried for 48 hours. The freeze-dried product was pulverized in a hammer mill and sieved through a 48 mesh. 1 g of the pulverized product was placed in a test tube, 5 to 20 mL of water or hot water (100°C) was added, and the mixture was left to stand in an ultrasonic cleaner for 60 minutes. The sample was centrifuged (2000 rpm, 20 minutes), and the supernatant was filtered through filter paper to recover the extract. Water or hot water (100°C) was added again to the centrifuged residue, and the mixture was left to stand in an ultrasonic cleaner for 60 minutes. This extraction operation was repeated four times to obtain an extract.
The amount of Compound A was quantified by HPLC. The results are shown in Table 1. The content of Compound A was shown as % by weight based on the pulverized dried raw material.
Figure JPOXMLDOC01-appb-T000009
Figure JPOXMLDOC01-appb-T000009
《実施例３～５》
　本実施例では、熱処理工程の時間を変化させて、化合物Ａを製造した。
　生鮮パクチーの葉を、９０℃の熱水で、０秒（実施例３）、３０秒（実施例４）又は６０秒間（実施例５）ブランチングし、湯を切って－４０℃で冷凍した。凍結したパクチーの葉を７２時間凍結乾燥した。得られた凍結乾燥物をコーヒーミルで粉砕した。得られた粉砕物１ｇを試験管に入れ、５－２０ｍＬの熱水（１００℃）を添加し、超音波洗浄機内で６０分間静置した。サンプルを遠心分離（２０００ｒｐｍ、２０分間）し、上清を濾紙でろ過し、抽出液を回収した。遠心分離した残渣に、再度、熱水（１００℃）を加え、超音波洗浄機内で６０分間静置した。この抽出操作を４回繰り返し、抽出物を得た。
　ＨＰＬＣにより化合物Ａを定量した。結果を表２に示す。なお、化合物Ａの含量は、乾燥原料の粉砕物に対する重量％で示した。 Examples 3 to 5
In this example, compound A was produced by changing the time of the heat treatment step.
Fresh coriander leaves were blanched in hot water at 90°C for 0 seconds (Example 3), 30 seconds (Example 4), or 60 seconds (Example 5), and then the hot water was drained and frozen at -40°C. The frozen coriander leaves were freeze-dried for 72 hours. The freeze-dried product was pulverized in a coffee mill. 1 g of the pulverized product was placed in a test tube, 5-20 mL of hot water (100°C) was added, and the tube was left to stand in an ultrasonic cleaner for 60 minutes. The sample was centrifuged (2000 rpm, 20 minutes), and the supernatant was filtered through filter paper to recover the extract. Hot water (100°C) was added again to the centrifuged residue, and the tube was left to stand in an ultrasonic cleaner for 60 minutes. This extraction procedure was repeated four times to obtain an extract.
The amount of Compound A was quantified by HPLC. The results are shown in Table 2. The content of Compound A was shown as % by weight based on the weight of the ground dry raw material.
Figure JPOXMLDOC01-appb-T000010
Figure JPOXMLDOC01-appb-T000010
《実施例６～８》
　本実施例では、熱処理工程を行わずに化合物Ａを製造した。
　生鮮パクチーの葉及び茎を、乳鉢を用いて磨り潰した。得られた磨砕物３．９７ｇを試験管（５０ｍＬ容量）に入れ、４０ｍＬの熱水（１００℃）を添加し、振とう機で３０分振とうした。サンプルを遠心分離（３５００ｒｐｍ、５分間）し、５ｍＬの上清を、冷蔵３時間（実施例６）、４０℃で３時間（実施例７）、又は室温２時間（実施例８）静置した。遠心分離（１１０００ｒｐｍ，１分）し、０．４５μｍのフィルターでろ過した。
　ＨＰＬＣにより化合物Ａを定量した。結果を表３に示す。なお、化合物Ａの含量は、生の原料の磨砕物に対する重量％で示した。 Examples 6 to 8
In this example, compound A was produced without carrying out a heat treatment step.
Fresh coriander leaves and stems were ground in a mortar. 3.97 g of the ground product was placed in a test tube (50 mL capacity), 40 mL of hot water (100°C) was added, and the mixture was shaken for 30 minutes using a shaker. The sample was centrifuged (3500 rpm, 5 minutes), and 5 mL of the supernatant was left to stand in a refrigerator for 3 hours (Example 6), at 40°C for 3 hours (Example 7), or at room temperature for 2 hours (Example 8). The sample was centrifuged (11000 rpm, 1 minute) and filtered through a 0.45 μm filter.
Compound A was quantified by HPLC. The results are shown in Table 3. The content of Compound A is shown as weight % based on the ground raw material.
Figure JPOXMLDOC01-appb-T000011
Figure JPOXMLDOC01-appb-T000011
《実施例９～１０》
　本実施例では、熱処理工程として、オートクレーブで処理した。
　生鮮パクチーの葉及び茎を、－４０℃で冷凍した。凍結したパクチーの葉及び茎を７２時間凍結乾燥した。得られた凍結乾燥物をミルサーで粉砕した。粉砕物をオートクレーブ滅菌（１２１℃、２気圧、２０分）した。得られた粉砕物０．２ｇを試験管に入れ、５ｍＬの熱水（１００℃）（実施例９）又は水（実施例１０）を添加し、２０分間、振とうした。サンプルを遠心分離（３０００ｒｐｍ、５分間）し、上清を回収した。遠心分離した残渣に、再度、熱水（１００℃）又は水を加え、２０分間、振とうした。この抽出操作を２回繰り返し、抽出物を得た。抽出物を、遠心分離（１１０００ｒｐｍ，１分）し、０．４５μｍのフィルターでろ過した。
　ＨＰＬＣにより化合物Ａを定量した。結果を表４に示す。なお、化合物Ａの含量は、乾燥原料の粉砕物に対する重量％で示した。 Examples 9 to 10
In this example, the heat treatment step was carried out in an autoclave.
Fresh coriander leaves and stems were frozen at -40°C. The frozen coriander leaves and stems were freeze-dried for 72 hours. The resulting freeze-dried product was pulverized in a blender. The pulverized product was sterilized in an autoclave (121°C, 2 atm, 20 min). 0.2 g of the resulting pulverized product was placed in a test tube, 5 mL of hot water (100°C) (Example 9) or water (Example 10) was added, and the mixture was shaken for 20 minutes. The sample was centrifuged (3000 rpm, 5 min) and the supernatant was collected. Hot water (100°C) or water was added again to the centrifuged residue, and the mixture was shaken for 20 minutes. This extraction operation was repeated twice to obtain an extract. The extract was centrifuged (11000 rpm, 1 min) and filtered through a 0.45 μm filter.
The amount of Compound A was quantified by HPLC. The results are shown in Table 4. The content of Compound A was shown as % by weight based on the pulverized dried raw material.
Figure JPOXMLDOC01-appb-T000012
Figure JPOXMLDOC01-appb-T000012
《実施例１１～１４》
　本実施例では、酸性極性溶媒を用いて、化合物Ａの製造を行った。
　生鮮パクチーの葉及び茎を、－４０℃で冷凍した。凍結したパクチーの葉及び茎を７２時間凍結乾燥した。得られた凍結乾燥物をミルサーで粉砕した。粉砕物０．１ｇを試験管に入れ、５ｍＬの熱水（１００℃）（実施例１１）、０．５％ギ酸を含む熱水（１００℃）（実施例１２）、０．５％ギ酸を含む水（実施例１３）、又は０．５％ギ酸及び５０％アセトニトリル（ＡＣＮ）を含む水（実施例１４）を添加し、１０分間、湯浴（９５度、実施例１１及び１２）、又は室温（実施例１３及び１４）で静置した。その後２０分間、振とうした。サンプルを遠心分離（３０００ｒｐｍ、５分間）し、上清を回収した。遠心分離した残渣に、再度、同じ溶媒を加え、２０分間、振とうした。この抽出操作を２回繰り返し、抽出物を得た。抽出物を、遠心分離（１１０００ｒｐｍ，１分）し、０．４５μｍのフィルターでろ過した。
　ＨＰＬＣにより化合物Ａを定量した。結果を表５に示す。なお、化合物Ａの含量は、乾燥原料の粉砕物に対する重量％で示した。 Examples 11 to 14
In this example, compound A was produced using an acidic polar solvent.
Fresh coriander leaves and stems were frozen at -40°C. The frozen coriander leaves and stems were freeze-dried for 72 hours. The resulting freeze-dried product was pulverized in a blender. 0.1 g of the pulverized product was placed in a test tube, and 5 mL of hot water (100°C) (Example 11), hot water (100°C) containing 0.5% formic acid (Example 12), water containing 0.5% formic acid (Example 13), or water containing 0.5% formic acid and 50% acetonitrile (ACN) (Example 14) was added, and the mixture was left to stand for 10 minutes in a water bath (95°C, Examples 11 and 12) or at room temperature (Examples 13 and 14). The mixture was then shaken for 20 minutes. The sample was centrifuged (3000 rpm, 5 minutes) and the supernatant was collected. The same solvent was added again to the centrifuged residue and shaken for 20 minutes. This extraction operation was repeated twice to obtain an extract. The extract was centrifuged (11,000 rpm, 1 min) and filtered through a 0.45 μm filter.
The amount of Compound A was quantified by HPLC. The results are shown in Table 5. The content of Compound A was shown as % by weight based on the pulverized dried raw material.
Figure JPOXMLDOC01-appb-T000013
Figure JPOXMLDOC01-appb-T000013
《実施例１５～１６》
　本実施例では、水と極性有機溶媒との混合溶媒を用いて、化合物Ａの製造を行った。
　生鮮パクチーの葉及び茎を、－４０℃で冷凍した。凍結したパクチーの葉及び茎を７２時間凍結乾燥した。得られた凍結乾燥物をミルサーで粉砕した。粉砕物０．１ｇを試験管に入れ、５０％アセトニトリルを含む水（実施例１５）、又は５０％エタノールを含む水（実施例１６）を５ｍｌ添加し、１０分間、室温で静置した。その後２０分間、振とうした。サンプルを遠心分離（３０００ｒｐｍ、５分間）し、上清を回収した。遠心分離した残渣に、再度、同じ溶媒を加え、２０分間、振とうした。この抽出操作を２回繰り返し、抽出物を得た。抽出物を、遠心分離（１１０００ｒｐｍ，１分）し、０．４５μｍのフィルターでろ過した。
　ＨＰＬＣにより化合物Ａを定量した。結果を表６に示す。なお、化合物Ａの含量は、乾燥原料の粉砕物に対する重量％で示した。 Examples 15 to 16
In this example, compound A was produced using a mixed solvent of water and a polar organic solvent.
Fresh coriander leaves and stems were frozen at -40°C. The frozen coriander leaves and stems were freeze-dried for 72 hours. The freeze-dried product was pulverized in a blender. 0.1 g of the pulverized product was placed in a test tube, and 5 ml of water containing 50% acetonitrile (Example 15) or water containing 50% ethanol (Example 16) was added, and the mixture was left to stand at room temperature for 10 minutes. The mixture was then shaken for 20 minutes. The sample was centrifuged (3000 rpm, 5 minutes) and the supernatant was collected. The same solvent was added again to the centrifuged residue, and the mixture was shaken for 20 minutes. This extraction procedure was repeated twice to obtain an extract. The extract was centrifuged (11000 rpm, 1 minute) and filtered through a 0.45 μm filter.
Compound A was quantified by HPLC. The results are shown in Table 6. The content of Compound A was shown as % by weight based on the pulverized dried raw material.
Figure JPOXMLDOC01-appb-T000014
Figure JPOXMLDOC01-appb-T000014
《実施例１７～１９》
　本実施例では、熱処理工程を行わずに、抽出溶媒の温度を７０℃～９０℃として化合物Ａの製造を行った。
　生鮮パクチーの葉及び茎を、－４０℃で冷凍した。凍結したパクチーの葉及び茎を７２時間凍結乾燥した。得られた凍結乾燥物をミルサーで粉砕した。粉砕物０．１ｇを試験管に入れ、５ｍＬの熱水（実施例１７；７０℃、実施例１８；８０℃、実施例１９；９０℃）を添加し、１０分間、添加した熱水と同じ温度の湯浴で静置した。その後２０分間、振とうした。サンプルを遠心分離（３０００ｒｐｍ、５分間）し、上清を回収した。この抽出物を、遠心分離（１１０００ｒｐｍ，１分）し、０．４５μｍのフィルターでろ過した。
　ＨＰＬＣにより化合物Ａを定量した。結果を表７に示す。なお、化合物Ａの含量は、乾燥原料の粉砕物に対する重量％で示した。 Examples 17 to 19
In this example, compound A was produced without carrying out a heat treatment step, and the temperature of the extraction solvent was set to 70°C to 90°C.
Fresh coriander leaves and stems were frozen at -40°C. The frozen coriander leaves and stems were freeze-dried for 72 hours. The freeze-dried product was pulverized in a blender. 0.1 g of the pulverized product was placed in a test tube, 5 mL of hot water (Example 17: 70°C, Example 18: 80°C, Example 19: 90°C) was added, and the tube was left to stand in a water bath at the same temperature as the added hot water for 10 minutes. The tube was then shaken for 20 minutes. The sample was centrifuged (3000 rpm, 5 minutes) and the supernatant was collected. The extract was centrifuged (11000 rpm, 1 minute) and filtered through a 0.45 μm filter.
Compound A was quantified by HPLC. The results are shown in Table 7. The content of Compound A was shown as % by weight based on the pulverized dry raw material.
Figure JPOXMLDOC01-appb-T000015
Figure JPOXMLDOC01-appb-T000015
　本発明の製造方法は、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造に用いることができる。 The manufacturing method of the present invention can be used to produce 2-O-trans-caffeoylhydroxycitric acid.

Claims (16)

  1. 　コリアンダーを極性溶媒に浸漬し、
    Figure JPOXMLDOC01-appb-C000001
     で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程を含む、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法。     Soak the coriander in a polar solvent.
    Figure JPOXMLDOC01-appb-C000001
     The present invention relates to a method for producing 2-O-trans-caffeoylhydroxycitric acid, the method comprising the step of extracting 2-O-trans-caffeoylhydroxycitric acid represented by the formula:
  2. 　前記抽出工程の前に、６５℃以上の熱処理工程をさらに含む、請求項１に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法。 The method for producing 2-O-trans-caffeoylhydroxycitric acid according to claim 1, further comprising a heat treatment step at 65°C or higher prior to the extraction step.
  3. 　前記抽出工程が、６５℃以上の極性溶媒による抽出工程である、請求項１又は２に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法。 The method for producing 2-O-trans-caffeoylhydroxycitric acid according to claim 1 or 2, wherein the extraction process is an extraction process using a polar solvent at 65°C or higher.
  4. 　前記抽出工程が、酸性極性溶媒による抽出工程である、請求項１～３のいずれかに記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法。 The method for producing 2-O-trans-caffeoylhydroxycitric acid according to any one of claims 1 to 3, wherein the extraction step is an extraction step using an acidic polar solvent.
  5. 　前記熱処理工程がブランチングである、請求項２に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸の製造方法。 The method for producing 2-O-trans-caffeoylhydroxycitric acid according to claim 2, wherein the heat treatment step is blanching.
  6. 　コリアンダーを極性溶媒に浸漬し、
    Figure JPOXMLDOC01-appb-C000002
     で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程を含む抽出方法によって得られる、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物。     Soak the coriander in a polar solvent.
    Figure JPOXMLDOC01-appb-C000002
     The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid is obtained by an extraction method including a step of extracting 2-O-trans-caffeoylhydroxycitric acid represented by the formula:
  7. 　前記抽出工程の前に、６５℃以上の熱処理工程をさらに含む、請求項６に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物。 　The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid according to claim 6, further comprising a heat treatment step at 65°C or higher prior to the extraction step.
  8. 　前記抽出工程が、６５℃以上の水性溶媒による抽出工程である、請求項６又は７に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物。 　The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid according to claim 6 or 7, wherein the extraction process is an extraction process using an aqueous solvent at 65°C or higher.
  9. 　前記抽出工程が、酸性極性溶媒による抽出工程である、請求項６～８のいずれかに記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物。 　The coriander extract containing 2-O-trans-caffeoylhydroxycitric acid according to any one of claims 6 to 8, wherein the extraction process is an extraction process using an acidic polar solvent.
  10. 　前記熱処理工程がブランチングである、請求項７に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を含むコリアンダー抽出物。 　The coriander extract containing 2-O-trans-caffeoyl hydroxycitric acid according to claim 7, wherein the heat treatment step is blanching.
  11. 　コリアンダーを極性溶媒に浸漬し、
    Figure JPOXMLDOC01-appb-C000003
     で表される２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を極性溶媒に抽出する工程と
    抽出された２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を製剤化する工程と
    を含む、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法。     Soak the coriander in a polar solvent.
    Figure JPOXMLDOC01-appb-C000003
     The present invention relates to a method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation, the method comprising the steps of: extracting 2-O-trans-caffeoylhydroxycitric acid represented by the formula (I) into a polar solvent; and formulating the extracted 2-O-trans-caffeoylhydroxycitric acid.
  12. 　前記抽出工程の前に、６５℃以上の熱処理工程をさらに含む、請求項１１に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法。 The method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to claim 11 further comprises a heat treatment step at 65°C or higher prior to the extraction step.
  13. 　前記抽出工程が、６５℃以上の極性溶媒による抽出工程である、請求項１１又は１２に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法。 The method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to claim 11 or 12, wherein the extraction process is an extraction process using a polar solvent at 65°C or higher.
  14. 　前記抽出工程が、酸性極性溶媒による抽出工程である、請求項１１～１３のいずれかに記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法。 The method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to any one of claims 11 to 13, wherein the extraction step is an extraction step using an acidic polar solvent.
  15. 　前記熱処理工程がブランチングである、請求項１２に記載の２－Ｏ－トランス－カフェオイルヒドロキシクエン酸含有製剤の製造方法。 The method for producing a 2-O-trans-caffeoylhydroxycitric acid-containing preparation according to claim 12, wherein the heat treatment step is blanching.
  16. 　コリアンダーの、乾燥物、破砕物、粉砕物、摩砕物又は粉体を含む組成物であって、２－Ｏ－トランス－カフェオイルヒドロキシクエン酸を抽出するために用いられる前記組成物。 A composition containing dried, crushed, pulverized, ground or powdered coriander, said composition being used to extract 2-O-trans-caffeoylhydroxycitric acid.
PCT/JP2023/035789 2022-09-30 2023-09-29 Method for producing 2-o-trans-caffeoylhydroxycitric acid WO2024071421A1 (en)

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Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CORTHOUT, J. ; PIETERS, L. ; CLAEYS, M. ; BERGHE, D. ; VLIETINCK, A.: "Antiviral caffeoyl esters from Spondias mombin", PHYTOCHEMISTRY, ELSEVIER, AMSTERDAM , NL, vol. 31, no. 6, 1 June 1992 (1992-06-01), Amsterdam , NL , pages 1979 - 1981, XP026633406, ISSN: 0031-9422, DOI: 10.1016/0031-9422(92)80344-E *
JAROSLAW MOLDOCH: "Phenolic Constituents of Knautia arvensis Aerial Parts", NATURAL PRODUCT COMMUNICATIONS, NATURAL PRODUCT INC., US, vol. 6, no. 11, 1 November 2011 (2011-11-01), US , pages 1934578X1100601, XP093154883, ISSN: 1934-578X, DOI: 10.1177/1934578X1100601117 *
PAULIN MUTWALE KAPEPULA: "Comparison of metabolic profiles and bioactivities of the leaves of three edible Congolese Hibiscus species", NATURAL PRODUCT RESEARCH, TAYLOR AND FRANCIS HEALTH SCIENCES, ABINGDON, GB, vol. 31, no. 24, 17 December 2017 (2017-12-17), GB , pages 2885 - 2892, XP093154885, ISSN: 1478-6419, DOI: 10.1080/14786419.2017.1305382 *

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