JPH0273079A - Production of flavonoid - Google Patents
Production of flavonoidInfo
- Publication number
- JPH0273079A JPH0273079A JP63226043A JP22604388A JPH0273079A JP H0273079 A JPH0273079 A JP H0273079A JP 63226043 A JP63226043 A JP 63226043A JP 22604388 A JP22604388 A JP 22604388A JP H0273079 A JPH0273079 A JP H0273079A
- Authority
- JP
- Japan
- Prior art keywords
- flavonoid
- flavone
- flavonoids
- activated carbon
- bisflavone
- 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.)
- Pending
Links
- 229930003935 flavonoid Natural products 0.000 title claims abstract description 36
- 150000002215 flavonoids Chemical class 0.000 title claims abstract description 36
- 235000017173 flavonoids Nutrition 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000000419 plant extract Substances 0.000 claims abstract description 5
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 12
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 abstract description 11
- 229930003944 flavone Natural products 0.000 abstract description 11
- 235000011949 flavones Nutrition 0.000 abstract description 11
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000243 solution Substances 0.000 abstract description 10
- 150000002212 flavone derivatives Chemical class 0.000 abstract description 8
- 239000003463 adsorbent Substances 0.000 abstract description 7
- -1 flavone glycoside Chemical class 0.000 abstract description 7
- 239000003513 alkali Substances 0.000 abstract description 6
- 229930182470 glycoside Natural products 0.000 abstract description 6
- 229910021529 ammonia Inorganic materials 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 239000000178 monomer Substances 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000287 crude extract Substances 0.000 abstract description 3
- 239000000284 extract Substances 0.000 abstract description 3
- 235000003599 food sweetener Nutrition 0.000 abstract description 3
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 abstract description 3
- 235000008696 isoflavones Nutrition 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 239000003765 sweetening agent Substances 0.000 abstract description 3
- 229930003949 flavanone Natural products 0.000 abstract description 2
- 235000011981 flavanones Nutrition 0.000 abstract description 2
- 150000002338 glycosides Chemical class 0.000 abstract description 2
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 abstract 1
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 abstract 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 235000011987 flavanols Nutrition 0.000 abstract 1
- 150000002207 flavanone derivatives Chemical class 0.000 abstract 1
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003795 desorption Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 3
- 235000005493 rutin Nutrition 0.000 description 3
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 3
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 3
- 229960004555 rutoside Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 2
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001789 chalcones Chemical class 0.000 description 2
- 235000005513 chalcones Nutrition 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002216 flavonol derivatives Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002515 isoflavone derivatives Chemical class 0.000 description 2
- 239000000401 methanolic extract Substances 0.000 description 2
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 2
- 229930019673 naringin Natural products 0.000 description 2
- 229940052490 naringin Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 244000015329 Aeginetia indica Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241001116498 Taxus baccata Species 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002208 flavanones Chemical class 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 description 1
- 235000007743 myricetin Nutrition 0.000 description 1
- 229940116852 myricetin Drugs 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は医薬２色素、甘味料、染料などに用いられるフ
ラボノイドの製法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for producing flavonoids used in pharmaceutical pigments, sweeteners, dyes, and the like.
（従来技術並びに解決すべき課題）
ヘスベリジン、ミリセチン、ルチン等のフラボノイドは
毛細管透過性を抑制する作用を有し、高血圧や脳卒中等
の血管性疾患の治療に有用である。(Prior art and problems to be solved) Flavonoids such as hesveridin, myricetin, and rutin have the effect of suppressing capillary permeability, and are useful for treating vascular diseases such as hypertension and stroke.
フラボノール誘導体には利尿作用があり、下剤としても
用いられる。その他フラボン誘導体は染料、抗酸化剤、
ロチノン等のイソフラボン類は殺虫剤、カルコン類は甘
味料として使われる。これらフラボノイドを植物抽出物
中の他の成分と分離する方法としては、液相間の分配を
利用する方法２分別沈殿による方法、吸着剤を用いる方
法などがあり、対象化合物あるいは植物によって様々な
組合せが実施されている。とりわけ吸着剤を用いる方法
は純度の高いフラボノイドを得るにはよい方法であり、
ポリアミド、ポリスチレンなどの樹脂や順相系、逆相系
のシリカゲルなどが用いられ−る。しかしながら、上記
のような吸着剤は高価であり、それに伴う装置も必要で
ある上、工程も多い。一方、活性炭は安価な吸着剤であ
り、フラボノイドを強く吸着する。しかし、吸着された
フラボノイドを選択的に脱着し、フラボノイドを回収す
る良い方法は知られておらず、かんきつ類の果汁の苦味
の原因である不要なナリンジンやヘスベリジン等のフラ
ボノイドを除去する目的で使用されているにすぎない。Flavonol derivatives have diuretic effects and are also used as laxatives. Other flavone derivatives include dyes, antioxidants,
Isoflavones such as rotinone are used as insecticides, and chalcones are used as sweeteners. Methods for separating these flavonoids from other components in plant extracts include a method that utilizes partition between liquid phases, a method that uses fractional precipitation, and a method that uses an adsorbent. is being implemented. In particular, the method using an adsorbent is a good method for obtaining highly pure flavonoids.
Resins such as polyamide and polystyrene, normal phase type silica gel, and reverse phase type silica gel are used. However, the above-mentioned adsorbents are expensive, require associated equipment, and involve many steps. On the other hand, activated carbon is an inexpensive adsorbent that strongly adsorbs flavonoids. However, there is no known good method for selectively desorbing and recovering flavonoids, and this method is used to remove unnecessary flavonoids such as naringin and hesveridin, which are the cause of the bitter taste of citrus juice. It's just that.
本発明は安価な吸着剤を用い、且つ操作が容易なフラボ
ノイド精製法の開発を目的とし、検討を重ねた結果であ
る。The present invention is the result of repeated studies aimed at developing a flavonoid purification method that uses an inexpensive adsorbent and is easy to operate.
（課題を解決するための手段）
本発明のフラボノイドの製法は、フラボノイドを含有す
る植物抽出物を活性炭で処理し、吸着したフラボノイド
をアルカリ溶液で脱着させることを特徴とするフラボノ
イドの製法である。(Means for Solving the Problems) The method for producing flavonoids of the present invention is characterized by treating a plant extract containing flavonoids with activated carbon, and desorbing the adsorbed flavonoids with an alkaline solution.
ここで述べるフラボノイドとは、フラボンフラバノール
、フラバノン、イソフラボン、カルコン、ビスフラボン
及びその配糖体を含む誘導体であり、植物体に広く分布
している一群の化合物を意味する。The flavonoids mentioned here are derivatives including flavonols, flavanones, isoflavones, chalcones, bisflavones, and their glycosides, and mean a group of compounds that are widely distributed in plants.
フラボノイドを含有する植物抽出物は水または有機溶媒
及びそれらの混合溶媒で抽出される粗抽出物でもその部
分精製画分でもよい。活性炭への吸着には水または任意
の有機溶媒を用いることができるが、フラボノイドの吸
着を十分に達成させるためには水ｌアルコールの混合溶
媒中で行なうのが望ましい。この際、低極性不溶物はろ
過により除去しておく。また、対象とするフラボノイド
の極性によって吸着力が異なるため、それに応じて水ｌ
アルコールの組成を検討する。アルコールとしてはエタ
ノールメタノールプロパノール、イソプロパツール、ブ
タノール等が用いられる。The plant extract containing flavonoids may be a crude extract extracted with water, an organic solvent, or a mixed solvent thereof, or a partially purified fraction thereof. Water or any organic solvent can be used for adsorption onto activated carbon, but in order to achieve sufficient adsorption of flavonoids, it is preferable to carry out the adsorption in a mixed solvent of water and alcohol. At this time, low polar insoluble matter is removed by filtration. In addition, since the adsorption power differs depending on the polarity of the target flavonoid, the amount of water
Consider the composition of alcohol. As the alcohol, ethanol, methanol, propanol, isopropanol, butanol, etc. are used.
例えば、フラボン配糖体の場合には１０〜４０％エタノ
ール、フラボンモノマーやビスフラボンの場合には３０
〜１００％エタノールを用いる。活性炭としては、ヤシ
殻２石炭、木材、ピッチ、石油系カーボン等を原料とす
るものが利用でき、°粉末が望ましいが粒状でもよい。For example, 10-40% ethanol for flavone glycosides, 30% ethanol for flavone monomers and bisflavones.
~100% ethanol is used. As the activated carbon, those made from coconut shell 2 coal, wood, pitch, petroleum carbon, etc. can be used, and powder is preferable, but granular forms may also be used.
添加する活性炭の量は抽出物中の予想される総フラボン
含量に依存するが、通常総フラボン量の２倍〜１０倍で
ある。活性炭を添加した溶液を常温または冷却下１０〜
３０ｍ１ｎ撹はんした後、オリバーフィルター等でろ過
しさらに使用した水ｌアルコール混合溶媒で洗浄する。The amount of activated carbon added depends on the expected total flavone content in the extract, but is usually between 2 and 10 times the total flavone content. The solution containing activated carbon is heated at room temperature or under cooling for 10~
After stirring for 30ml, the mixture is filtered using an Oliver filter and washed with the used water/alcohol mixed solvent.
この工程で糖類やサポニン等を除去することができる。Sugars, saponins, etc. can be removed in this step.
フラボノイドの脱着にはカセイソーダ、アンモニア、ア
ルキルアミン等のアルカリを用いることができるが脱着
後のアルカリの除去を考慮すると希アンモニア水溶液が
最も適している。アルカリの濃度は０．１％〜５％の範
囲で使用でき、脱着させるフラボノイドの極性に対応し
てこれにアルコールを加えた脱着液を調製する。Alkali such as caustic soda, ammonia, and alkylamines can be used for desorption of flavonoids, but a dilute ammonia aqueous solution is most suitable in consideration of removal of the alkali after desorption. The concentration of alkali can be used in the range of 0.1% to 5%, and a desorption solution is prepared by adding alcohol to this in accordance with the polarity of the flavonoid to be desorbed.
例えば、フラボン配糖体の場合には０．５〜５％アンモ
ニアを含む２０〜５０％エタノール水溶液、フラボンモ
ノマーやビスフラボンの場合にはさらにアルコール濃度
の高い水溶液を用いることができる。For example, in the case of flavone glycosides, a 20-50% ethanol aqueous solution containing 0.5-5% ammonia can be used, and in the case of flavone monomers and bisflavones, an aqueous solution with an even higher alcohol concentration can be used.
また、これら比率の異なる脱着液を組み合わせることに
よりフラボノイド混合物を分離することも可能である。It is also possible to separate flavonoid mixtures by combining desorption liquids with different ratios.
使用後の活性炭は水洗いしてアルカリを除去したのち再
生することができる。Activated carbon after use can be recycled after being washed with water to remove alkali.
次に実施例によって説明する。Next, an example will be explained.
実施例１
エンジュのつぼみのメタノール抽出物１００ｇに２０％
エタノール水溶液Ｌｅを加え加熱撹はんした後、不溶物
を除去する。活性炭５０ｇを添加し、撹はん後ろ過し、
活性炭を同溶媒にて洗浄する。次に１％アンモニアを含
む４０％エタノール水溶液１君で活性炭を洗いフラボノ
イドを脱着し、得られたろ液を濃縮して粗ルチンを得る
。これを２０％エタノールにて再結晶することによりル
チン２．４ｇが得られる。Example 1 20% in 100g of methanol extract of Ange bud
After adding an aqueous ethanol solution Le and stirring with heating, insoluble materials are removed. Add 50g of activated carbon, stir and filter.
Wash the activated carbon with the same solvent. Next, the activated carbon is washed with a 40% aqueous ethanol solution containing 1% ammonia to desorb flavonoids, and the resulting filtrate is concentrated to obtain crude rutin. By recrystallizing this from 20% ethanol, 2.4 g of rutin is obtained.
実施例２
イチョウ葉１００ｋｇを６０％エタノールで還流抽出し
得られるエキス２７ｋｇに２０％エタノール２００ ｇ
を加え５０〜６０°Ｃに加熱した後、不溶物を除去する
。Example 2 27 kg of extract obtained by refluxing 100 kg of ginkgo leaves with 60% ethanol and 200 g of 20% ethanol
After adding and heating to 50-60°C, insoluble matter is removed.
得られた溶液に活性炭１０ｋｇを入れて１０分間撹はん
後ろ過し、さらに１００−ｅの２０％エタノールで洗浄
する。続いてすみやかに２％アンモニアを含む４０％エ
タノール水溶液にて洗浄し、浄液を濃縮して粗フラボノ
イド画分を得る。６０％エタノール抽出物中６％であっ
たフラボノイド類が粗フラボノイド画分では３３％に濃
縮される。10 kg of activated carbon is added to the obtained solution, stirred for 10 minutes, filtered, and further washed with 20% ethanol of 100-e. Subsequently, it is immediately washed with a 40% aqueous ethanol solution containing 2% ammonia, and the purified liquid is concentrated to obtain a crude flavonoid fraction. Flavonoids, which were 6% in the 60% ethanol extract, are concentrated to 33% in the crude flavonoid fraction.
実施例３
イチビの乾燥葉のメタノール抽出物にヘキサンを加えヘ
キサン可溶部を除去した後クロロホルム可溶物を得る。Example 3 Hexane was added to a methanol extract of dried leaves of A. japonica and the hexane-soluble portion was removed to obtain a chloroform-soluble material.
これを８０％メタノールに溶解し活性炭を加えてろ過し
、続いて１％水酸化ナトリウムを含む８０％エタノール
水溶液で活性炭を洗い洗液を濃縮する。得られた濃縮液
を希硫酸で中和して再沈殿させるとシアドピチシンを主
成分とするビスフラボン混合物が得られる。収量はイチ
イの葉より０．２％である。This is dissolved in 80% methanol, activated carbon is added, and filtered. Subsequently, the activated carbon is washed with an 80% aqueous ethanol solution containing 1% sodium hydroxide, and the washing liquid is concentrated. When the obtained concentrated solution is neutralized with dilute sulfuric acid and reprecipitated, a bisflavone mixture containing cyadopiticin as a main component is obtained. The yield is 0.2% compared to yew leaves.
（発明の効果） 以下に発明の効果を列挙する。(Effect of the invention) The effects of the invention are listed below.
１） 従来のポリアミドやポリスチレン等の吸着剤を用
いる方法に比べ安価であり、特別な設備を必要としない
。1) It is cheaper than conventional methods using adsorbents such as polyamide and polystyrene, and does not require special equipment.
２） 不要物を多く含む粗抽出物も直接処理することが
出来、フラボノイド画分を一挙に濃縮することができる
ため、精製・濃縮の工程が短縮できる。2) Crude extracts containing many unnecessary substances can be directly processed, and the flavonoid fraction can be concentrated all at once, so the purification and concentration steps can be shortened.
３） フラボンモノマーだけでなくビスフラボンやフラ
ボン配糖体にわたり広範囲の化合物に応用できる。3) It can be applied to a wide range of compounds, including not only flavone monomers but also bisflavones and flavone glycosides.
４） 従来、活性炭を用いて除去・廃棄されていたナリ
ンジン、ヘスベリジン等のかんきつ類中のフラボノイド
の有効利用ができる。4) Flavonoids in citrus fruits such as naringin and hesveridin, which were conventionally removed and disposed of using activated carbon, can be effectively utilized.
Claims (1)
吸着したフラボノイドをアルカリ溶液で脱着させること
を特徴とするフラボノイドの製法。Plant extracts containing flavonoids are treated with activated carbon,
A method for producing flavonoids characterized by desorbing adsorbed flavonoids with an alkaline solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63226043A JPH0273079A (en) | 1988-09-09 | 1988-09-09 | Production of flavonoid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63226043A JPH0273079A (en) | 1988-09-09 | 1988-09-09 | Production of flavonoid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0273079A true JPH0273079A (en) | 1990-03-13 |
Family
ID=16838889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63226043A Pending JPH0273079A (en) | 1988-09-09 | 1988-09-09 | Production of flavonoid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0273079A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6030621A (en) * | 1998-03-19 | 2000-02-29 | De Long; Xie | Ginkgo biloba composition, method to prepare the same and uses thereof |
| WO2002000236A1 (en) * | 2000-06-29 | 2002-01-03 | Dr. Willmar Schwabe Gmbh & Co. | Extracts from sophora species, method for producing the same and their use |
| JP2005504753A (en) * | 2001-07-27 | 2005-02-17 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Bauhinia extract |
| JP2007289185A (en) * | 2006-04-25 | 2007-11-08 | Nateco2 Gmbh & Co Kg | Method for preparing high-purity xanthohumol-containing powder and use thereof |
| WO2009059890A1 (en) * | 2007-11-06 | 2009-05-14 | Unilever Nv | Food product |
| JP2010215580A (en) * | 2009-03-18 | 2010-09-30 | Taiyo Kagaku Co Ltd | Method for producing immunomodulator |
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| CN103570662A (en) * | 2013-11-19 | 2014-02-12 | 东南大学 | Preparation method of high-purity rutin |
| CN110870882A (en) * | 2019-10-29 | 2020-03-10 | 南京林业大学 | Method for separating and preparing ginkgetin in ginkgo leaf extract |
| CN111620846A (en) * | 2020-05-30 | 2020-09-04 | 重庆西南果品营养研究院 | Comprehensive utilization method of citrus peel residues |
-
1988
- 1988-09-09 JP JP63226043A patent/JPH0273079A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6632460B2 (en) | 1998-03-19 | 2003-10-14 | Shanghai Xingling Sci. & Tech. Pharmaceutical Co., Ltd. | Ginkgo biloba composition, method to prepare the same and uses thereof |
| US6187314B1 (en) | 1998-03-19 | 2001-02-13 | Shanghai Inst. Of Chinese Materia Medica | Ginkgo biloba composition method to prepare the same and uses thereof |
| US6030621A (en) * | 1998-03-19 | 2000-02-29 | De Long; Xie | Ginkgo biloba composition, method to prepare the same and uses thereof |
| US6475534B2 (en) | 1998-03-19 | 2002-11-05 | Shanghai Xingling Sci. & Tech. Pharmaceutical Co., Ltd. | Ginkgo biloba composition, method to prepare the same and uses thereof |
| CN1299672C (en) * | 2000-06-29 | 2007-02-14 | 威廉施瓦布博士有限公司 | Extracts from sophora,production method and purposes thereof |
| WO2002000236A1 (en) * | 2000-06-29 | 2002-01-03 | Dr. Willmar Schwabe Gmbh & Co. | Extracts from sophora species, method for producing the same and their use |
| JP2005504753A (en) * | 2001-07-27 | 2005-02-17 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Bauhinia extract |
| JP2007289185A (en) * | 2006-04-25 | 2007-11-08 | Nateco2 Gmbh & Co Kg | Method for preparing high-purity xanthohumol-containing powder and use thereof |
| WO2009059890A1 (en) * | 2007-11-06 | 2009-05-14 | Unilever Nv | Food product |
| JP2010215580A (en) * | 2009-03-18 | 2010-09-30 | Taiyo Kagaku Co Ltd | Method for producing immunomodulator |
| CN103059081A (en) * | 2012-12-31 | 2013-04-24 | 宁波泰新生物科技有限公司 | Method for extracting quercetin-3-O-rutinose from taxus mairei leaves |
| CN103570662A (en) * | 2013-11-19 | 2014-02-12 | 东南大学 | Preparation method of high-purity rutin |
| CN110870882A (en) * | 2019-10-29 | 2020-03-10 | 南京林业大学 | Method for separating and preparing ginkgetin in ginkgo leaf extract |
| CN111620846A (en) * | 2020-05-30 | 2020-09-04 | 重庆西南果品营养研究院 | Comprehensive utilization method of citrus peel residues |
| CN111620846B (en) * | 2020-05-30 | 2022-08-12 | 重庆西南果品营养研究院 | Comprehensive utilization method of citrus peel residues |
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