JPH01175978A - Production of crude catechin compound - Google Patents
Production of crude catechin compoundInfo
- Publication number
- JPH01175978A JPH01175978A JP62333981A JP33398187A JPH01175978A JP H01175978 A JPH01175978 A JP H01175978A JP 62333981 A JP62333981 A JP 62333981A JP 33398187 A JP33398187 A JP 33398187A JP H01175978 A JPH01175978 A JP H01175978A
- Authority
- JP
- Japan
- Prior art keywords
- aqueous solution
- gel
- fraction
- eluted
- epicatechin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 235000005487 catechin Nutrition 0.000 title claims abstract description 9
- -1 catechin compound Chemical class 0.000 title claims abstract description 5
- 229950001002 cianidanol Drugs 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 241001122767 Theaceae Species 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 10
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 claims abstract description 8
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 claims abstract description 8
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 claims abstract description 6
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960001948 caffeine Drugs 0.000 claims abstract description 6
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims abstract description 6
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 239000012153 distilled water Substances 0.000 claims abstract description 5
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 4
- 229920005654 Sephadex Polymers 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 235000000346 sugar Nutrition 0.000 claims description 4
- 150000008163 sugars Chemical class 0.000 claims description 4
- 230000005484 gravity Effects 0.000 claims description 3
- 235000018553 tannin Nutrition 0.000 claims description 3
- 229920001864 tannin Polymers 0.000 claims description 3
- 239000001648 tannin Substances 0.000 claims description 3
- 150000003505 terpenes Chemical class 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 6
- 238000004440 column chromatography Methods 0.000 abstract description 3
- 210000003918 fraction a Anatomy 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 3
- 229920002307 Dextran Polymers 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 210000002196 fr. b Anatomy 0.000 abstract 1
- 238000012856 packing Methods 0.000 abstract 1
- 150000001765 catechin Chemical class 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 4
- 241000238557 Decapoda Species 0.000 description 3
- 239000001058 brown pigment Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000001877 deodorizing effect Effects 0.000 description 2
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- LSHVYAFMTMFKBA-PZJWPPBQSA-N (+)-catechin-3-O-gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-PZJWPPBQSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は茶の抽出液からカテキン化合物を高速液体クロ
マトグラフィにより精製分画するための原材料である茶
の粗カテキン化合物を高収率で製造する方法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention is for producing crude tea catechin compounds in high yield, which are raw materials for purifying and fractionating catechin compounds from tea extract by high performance liquid chromatography. Regarding the method.
茶の抽出液から得た粗カテキン化合物を高速液体クロマ
トグラフィーにより精製分画するためには、茶カテキン
と共存するカフェイン、茶色素、茶タンニン酸化物等の
夾雑物の分離が前操作として不可欠である。In order to purify and fractionate crude catechin compounds obtained from tea extract by high-performance liquid chromatography, it is essential to separate impurities such as caffeine, brown pigment, and tea tannin oxides that coexist with tea catechins as a pre-operation. It is.
このための従来方法は、ブタノール、酢酸エチル等の疎
水性有機溶媒とアストン、メタノール、エタノール等の
親水性有機溶媒とを適宜組合わせた多量の溶剤を用いて
、カフェイン、アミノ酸。The conventional method for this purpose is to use a large amount of a solvent in which a hydrophobic organic solvent such as butanol or ethyl acetate is appropriately combined with a hydrophilic organic solvent such as Aston, methanol, or ethanol to remove caffeine or amino acids.
糖、ステロイド、茶色素、茶タンニン酸化物等を除去し
た茶の抽出液から、カテキンを酢酸エチル等の有機溶媒
を用いて抽出した後、該有機溶媒を蒸留除去してその残
部を水溶液として噴霧又は凍結乾燥して得るものであっ
た。After extracting catechins from tea extract from which sugars, steroids, brown pigments, tea tannin oxides, etc. have been removed using an organic solvent such as ethyl acetate, the organic solvent is distilled off and the remainder is sprayed as an aqueous solution. Alternatively, it could be obtained by freeze-drying.
しかしながら、上記従来方法においては、多量の溶媒を
使用しなければならない点に、またそれ故に操作の安全
性に劣り、コスト高となる等の点に問題があった。However, the above-mentioned conventional method has problems in that a large amount of solvent must be used, and therefore operational safety is poor and costs are high.
本発明は、上記方法と異なり、濃度を適宜変えた親水性
有機溶媒の水溶液だけを用い、ゲルカラムクロマトグラ
フィーにより連続的に夾雑物を分離したのち、四種の茶
カテキン化合物を抽出する方法を提供することにより、
Ａ分画とＢ分画とに分離した茶カテキン製剤を効率的、
経済的に量産可能とするものであって、得られた茶カテ
キンは強力な抗酸化作用を有しており、各種食品、油脂
。The present invention differs from the above method in that it uses only an aqueous solution of a hydrophilic organic solvent with an appropriately varied concentration, continuously separates impurities by gel column chromatography, and then extracts four types of tea catechin compounds. By providing
Efficiently prepare tea catechin preparations separated into A and B fractions.
The tea catechins that can be economically mass-produced have a strong antioxidant effect and can be used in various foods, oils and fats.
香料等への利用が期待されるほか、血中コレステロール
増加抑制作用、高血圧予防、抗菌作用、抗ウイルス増殖
作用、抗ガン作用、消臭作用等の作用を有し、広範囲に
及ぶ用途を有するものとなる。In addition to being expected to be used in fragrances, etc., it also has a wide range of uses, including inhibiting blood cholesterol increase, preventing high blood pressure, antibacterial activity, antiviral growth, anticancer activity, and deodorizing activity. becomes.
上記目的を達成するために、本発明は、茶葉から温水乃
至熱水を用いて溶出した水溶性化合物を、ハイドロキシ
ルプロピル化デキストランゲル又は親水性ビニールポリ
マーゲルを充填したカラムに注入し、次いで先ず蒸留水
を用い、次にメタノール、エタノール又はアセトン水溶
液好ましくは５〜１５％前後のものを用いてカラムを自
然流下法あるいは吸引法によって洗浄して、ゲルに吸着
するカフェイン、アミノ酸、糖、テルペノイド、有機酸
９色素、多種のタンニン酸化物等を分離し、次にゲル内
の分離残留物より２０〜３０％前後のメタノール、エタ
ノール又はアセトン水溶液にて、Ｌ−エビカテキン、Ｌ
−エピガロカテキンを含むＡ分画を溶出させ、更に４０
〜６５％前後のメタノール、エタノール又はアセトン水
溶液にてＬ−エビカテキン・ガレート、Ｌ−エピガロカ
テキン・ガレートを含むＢ分画を溶出分離する粗カテキ
ン化合物製造方法としたものである。In order to achieve the above object, the present invention first injects water-soluble compounds eluted from tea leaves using warm or hot water into a column packed with hydroxylpropylated dextran gel or hydrophilic vinyl polymer gel, and then first The column is washed with distilled water and then with an aqueous solution of methanol, ethanol, or acetone, preferably around 5-15%, by gravity flow or suction to remove caffeine, amino acids, sugars, and terpenoids adsorbed into the gel. , organic acid 9 pigments, various tannin oxides, etc. are separated, and then L-epicatechin, L
- Elute the A fraction containing epigallocatechin and further
This is a method for producing a crude catechin compound, in which a B fraction containing L-epicatechin gallate and L-epigallocatechin gallate is eluted and separated using a methanol, ethanol or acetone aqueous solution of about 65%.
以下、本発明の一実施例を説明する。 An embodiment of the present invention will be described below.
茶１ｋｇを熱湯２０１’にて３０分間抽出し圧搾して得
た搾汁を集め、これをハイドロキシルプロピル化デキス
トランゲル５００ｇのゲル充填の円柱状カラムに注入し
、自然流下又は吸引法により速やかに流下させた。全量
注入後３Ｉｌの蒸留水にてカラムを洗浄、カフェイン、
アミノ酸、糖等を洗脱した。次に１５％の親水性有機溶
媒水溶液３Ｉｌを流下させ、テルペノイド、茶色素及び
茶タンニン酸化物を洗脱した。その後３０％の親水性有
機溶媒水溶液３βを流下させて、アンドシアン、更にＬ
−エピガロカテキン、Ｌ−エビカテキンを含むＡ分画を
ゲルカラムから溶出させ、次いで６０％の親水性有機溶
媒水溶液３Ｉｌを流下させて、Ｌ−エピガロカテキンガ
レート、Ｌ−エビカテキンガレートを含むＢ分画をゲル
カラムから溶出させた。この各分画を集めて噴霧乾燥す
ると茶カテキン化合物が作られた。Extract 1 kg of tea with boiling water 201' for 30 minutes, squeeze it, collect the juice obtained, inject it into a cylindrical column packed with 500 g of hydroxylpropylated dextran gel, and immediately extract by gravity flow or suction method. I let it flow down. After injecting the entire amount, wash the column with 3Il of distilled water, add caffeine,
Amino acids, sugars, etc. were washed away. Next, 3 Il of a 15% aqueous solution of a hydrophilic organic solvent was allowed to flow down to wash away terpenoids, brown pigments, and brown tannin oxides. After that, a 30% aqueous solution of a hydrophilic organic solvent 3β was allowed to flow down, and andocyan, and further L
- Fraction A containing epigallocatechin and L-epicatechin is eluted from the gel column, and then 3Il of a 60% aqueous solution of a hydrophilic organic solvent is allowed to flow down. Fractions were eluted from the gel column. These fractions were collected and spray-dried to produce tea catechin compounds.
上記分画状態は、第１図に示されているとおりであり、
図は茶搾汁を用いたゲルカラムクロマトグラム（Ｓｅｐ
ｈａｄｅｘＬＩ］−２０カラムクロマトグラフイ）の図
である。図中、Ａは上記Ａ分画、Ｂは上記Ｂ分画を、点
線はメタノール濃度を示している。The above fractionation state is as shown in Figure 1,
The figure shows a gel column chromatogram using tea juice (Sep.
[hadexLI]-20 column chromatography). In the figure, A indicates the above-mentioned A fraction, B indicates the above-mentioned B fraction, and the dotted line indicates the methanol concentration.
また、第２図にはＡ分画の、第３図にはＢ分画の高速液
体クロマトグラムが示されている。Further, FIG. 2 shows a high performance liquid chromatogram of the A fraction, and FIG. 3 shows a high performance liquid chromatogram of the B fraction.
Ａ分画には９７．８％のし一二ビガロカテキン（符号１
）と、僅少のし一エビカテキンが含まれており、Ｂ分画
には、７７．２％のし一エビがロ力テキンガレート（符
号２）、１４．６％のし一エピカテキンガレート （符
号３）が含まれていた。Fraction A contains 97.8% of the bigallocatechin (code 1
) and a small amount of shrimp catechin, and the B fraction contains 77.2% shrimp catechin gallate (code 2) and 14.6% shrimp epicatechin gallate (code 2). 3) was included.
上記実施例による抽出液からの粗カテキン化合物の収量
は下表のとおりであった。The yield of crude catechin compounds from the extract according to the above example was as shown in the table below.
なお、上記において搾汁抽出の条件は特に限定されるも
のではない。ハイドロキシルプロピル化デキストランゲ
ルはこれに代えて親水性ビニールポリマーゲル等を用い
ることができる。蒸留水と親水性有機溶媒によって順次
カラムを洗浄することによって狭窄物の除去が十分に行
われるが、後者の濃度は洗浄作用として５〜１５％前後
とするのが好ましい。Note that the conditions for juice extraction in the above are not particularly limited. Hydrophilic vinyl polymer gel or the like can be used instead of the hydroxylpropylated dextran gel. Strict substances can be sufficiently removed by sequentially washing the column with distilled water and a hydrophilic organic solvent, and the concentration of the latter is preferably about 5 to 15% for its washing effect.
Ａ分画の抽出は上記２０〜３０％前後において最大であ
り、親水性溶媒の濃度が薄すぎると分画が行われ難くな
り、上記濃度の範囲内でほとんどＡ分画が出てしまった
上、上記範囲程度よりも濃すぎるとＢ分画が混在して分
画が不十分となる。Ｂ分画の抽出は上記４０〜６５％前
後において最大であり、この程度よりも薄すぎるとＡ分
画との分画が不十分となり、濃すぎる領域ではＢ分画の
残量はほとんどなく、分画の機能性がなくなる。The extraction of the A fraction is maximum at around 20 to 30% above, and if the concentration of the hydrophilic solvent is too thin, it becomes difficult to carry out the fractionation, and within the above concentration range, most of the A fraction is extracted. If it is too concentrated than the above range, the B fraction will be present and the fractionation will be insufficient. The extraction of the B fraction is maximum at around 40 to 65%, and if it is too thin than this level, the fractionation with the A fraction will be insufficient, and if it is too dark, there will be almost no remaining amount of the B fraction, The functionality of the fraction is lost.
以上のように、本発明によれば、親水性有機溶媒のみを
使用するため作業の安全性が確保され、単一溶媒である
ので、後処理にも煩わしさを生じさせることなく、Ａ分
画とＢ分画とに分離した茶の粗カテキン化合物を効率的
かつ経済的に量産でき、得られた茶カテキンは強力な抗
酸化作用を有しており、各種食品、油脂、香料等への利
用が期待されるほか、血中コレステロール増加抑制作用
。As described above, according to the present invention, work safety is ensured because only a hydrophilic organic solvent is used, and since a single solvent is used, the A fraction can be separated without causing any trouble in post-processing. The crude tea catechin compounds separated into the and B fraction can be efficiently and economically mass-produced, and the obtained tea catechins have a strong antioxidant effect and can be used in various foods, oils and fats, fragrances, etc. In addition to being expected to have the effect of suppressing the increase in blood cholesterol.
高血圧予防、抗菌作用、抗ウイルス増殖作用、抗ガン作
用、消臭作用等の作用を有し、広範囲に及ぶ用途を有す
る。It has a wide range of uses, including antihypertensive, antibacterial, antiviral growth, anticancer, and deodorizing effects.
第１図は茶搾汁のゲルカラムクロマトグラムの図、第２
図はＡ分画の成分組成図、第３図はＢ分画の成分組成図
である。Figure 1 is a gel column chromatogram of tea juice, Figure 2
The figure shows the composition of the A fraction, and FIG. 3 shows the composition of the B fraction.
Claims (1)
、ハイドロキシルプロピル化デキストランゲル又は親水
性ビニールポリマーゲルを充填したカラムに注入し、次
いで先ず蒸留水を用い、次にメタノール、エタノール又
はアセトン水溶液を用いてカラムを自然流下法あるいは
吸引法によって洗浄して、ゲルに吸着するカフェイン、
アミノ酸、糖、テルペノイド、有機酸、色素、多種のタ
ンニン酸化物等を分離し、次にゲル内の分離残留物より
２０〜３０％前後のメタノール、エタノール又はアセト
ン水溶液にて、Ｌ−エピカテキン、Ｌ−エピガロカテキ
ンを含むＡ分画を溶出させ、更に４０〜６５％前後のメ
タノール、エタノール又はアセトン水溶液にてＬ−エピ
カテキン・ガレート、Ｌ−エピガロカテキン・ガレート
を含むＢ分画を溶出分離することを特徴とする粗カテキ
ン化合物製造方法。Water-soluble compounds eluted from tea leaves using warm or hot water are injected into a column packed with hydroxylpropylated dextran gel or hydrophilic vinyl polymer gel, then first with distilled water and then with methanol, ethanol or acetone. Caffeine is adsorbed onto the gel by washing the column with an aqueous solution by gravity flow or suction.
Amino acids, sugars, terpenoids, organic acids, pigments, various tannin oxides, etc. are separated, and then L-epicatechin, L-epicatechin, Elute the A fraction containing L-epigallocatechin, and further elute the B fraction containing L-epicatechin gallate and L-epigallocatechin gallate with a methanol, ethanol or acetone aqueous solution of around 40 to 65%. A method for producing a crude catechin compound, characterized by separating it.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62333981A JP2703241B2 (en) | 1987-12-29 | 1987-12-29 | Method for producing crude catechin compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62333981A JP2703241B2 (en) | 1987-12-29 | 1987-12-29 | Method for producing crude catechin compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01175978A true JPH01175978A (en) | 1989-07-12 |
| JP2703241B2 JP2703241B2 (en) | 1998-01-26 |
Family
ID=18272153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62333981A Expired - Fee Related JP2703241B2 (en) | 1987-12-29 | 1987-12-29 | Method for producing crude catechin compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2703241B2 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01190624A (en) * | 1988-01-26 | 1989-07-31 | Itouen:Kk | Agent for suppressing microorganism in mouth and gargle containing said agent |
| KR20030060723A (en) * | 2002-01-09 | 2003-07-16 | 박근형 | Separation and production methods of caffeine, epigallocatechin, epicatechin, epigallocatechingallate, and epicatechingallate from tea leaves |
| WO2006008833A1 (en) * | 2004-07-22 | 2006-01-26 | Mitsui Norin Co., Ltd. | Tea polyphenol composition and process for producing the same |
| JP2006206482A (en) * | 2005-01-27 | 2006-08-10 | Kao Corp | Method for producing non-polymeric catechin composition |
| JP2006206483A (en) * | 2005-01-27 | 2006-08-10 | Kao Corp | Method for producing non-polymeric catechin composition |
| JP2009060824A (en) * | 2007-09-05 | 2009-03-26 | Kao Corp | Method for producing purified green tea extract |
| JP2010095476A (en) * | 2008-10-17 | 2010-04-30 | Ito En Ltd | Refined tea extract and method for producing the same |
| JP2011514347A (en) * | 2008-03-06 | 2011-05-06 | ノバ ラボラトリーズ エスディーエヌ ビーエイチディー | Extracts from oil palm leaves containing phenolic acid |
| CN103145679A (en) * | 2013-02-28 | 2013-06-12 | 武汉华大药业有限公司 | Preparation method and application of epigallocatechin gallate |
-
1987
- 1987-12-29 JP JP62333981A patent/JP2703241B2/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01190624A (en) * | 1988-01-26 | 1989-07-31 | Itouen:Kk | Agent for suppressing microorganism in mouth and gargle containing said agent |
| KR20030060723A (en) * | 2002-01-09 | 2003-07-16 | 박근형 | Separation and production methods of caffeine, epigallocatechin, epicatechin, epigallocatechingallate, and epicatechingallate from tea leaves |
| WO2006008833A1 (en) * | 2004-07-22 | 2006-01-26 | Mitsui Norin Co., Ltd. | Tea polyphenol composition and process for producing the same |
| JP2006206482A (en) * | 2005-01-27 | 2006-08-10 | Kao Corp | Method for producing non-polymeric catechin composition |
| JP2006206483A (en) * | 2005-01-27 | 2006-08-10 | Kao Corp | Method for producing non-polymeric catechin composition |
| JP2009060824A (en) * | 2007-09-05 | 2009-03-26 | Kao Corp | Method for producing purified green tea extract |
| JP2011514347A (en) * | 2008-03-06 | 2011-05-06 | ノバ ラボラトリーズ エスディーエヌ ビーエイチディー | Extracts from oil palm leaves containing phenolic acid |
| JP2010095476A (en) * | 2008-10-17 | 2010-04-30 | Ito En Ltd | Refined tea extract and method for producing the same |
| CN103145679A (en) * | 2013-02-28 | 2013-06-12 | 武汉华大药业有限公司 | Preparation method and application of epigallocatechin gallate |
| CN103145679B (en) * | 2013-02-28 | 2015-04-29 | 武汉华大药业有限公司 | Preparation method and application of epigallocatechin gallate |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2703241B2 (en) | 1998-01-26 |
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