JPH01304101A - Preparation of conjugated polysaccharide - Google Patents
Preparation of conjugated polysaccharideInfo
- Publication number
- JPH01304101A JPH01304101A JP13463388A JP13463388A JPH01304101A JP H01304101 A JPH01304101 A JP H01304101A JP 13463388 A JP13463388 A JP 13463388A JP 13463388 A JP13463388 A JP 13463388A JP H01304101 A JPH01304101 A JP H01304101A
- Authority
- JP
- Japan
- Prior art keywords
- extract
- liq
- ultrafiltration membrane
- filtered
- water
- 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
- 150000004676 glycans Chemical class 0.000 title claims abstract description 22
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 22
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 22
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 14
- 239000012528 membrane Substances 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 8
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000006286 aqueous extract Substances 0.000 claims abstract description 5
- 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 3
- 229960001948 caffeine Drugs 0.000 claims abstract description 3
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 235000019804 chlorophyll Nutrition 0.000 claims abstract description 3
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 3
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 3
- 229920001864 tannin Polymers 0.000 claims abstract description 3
- 239000001648 tannin Substances 0.000 claims abstract description 3
- 235000018553 tannin Nutrition 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000012466 permeate Substances 0.000 claims description 3
- 229930002875 chlorophyll Natural products 0.000 claims description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims 1
- 239000000284 extract Substances 0.000 abstract description 16
- 238000000034 method Methods 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000000502 dialysis Methods 0.000 abstract description 2
- 244000302899 Cassia mimosoides Species 0.000 abstract 2
- 235000014112 Cassia mimosoides Nutrition 0.000 abstract 2
- 244000067456 Chrysanthemum coronarium Species 0.000 abstract 2
- 235000007871 Chrysanthemum coronarium Nutrition 0.000 abstract 2
- 244000269722 Thea sinensis Species 0.000 abstract 2
- 238000005194 fractionation Methods 0.000 abstract 2
- 235000013616 tea Nutrition 0.000 abstract 2
- 241001122767 Theaceae Species 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003472 antidiabetic agent Substances 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000013376 functional food Nutrition 0.000 description 3
- 235000013402 health food Nutrition 0.000 description 3
- 229940126904 hypoglycaemic agent Drugs 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003809 water extraction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003908 quality control method Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- -1 D-lipose Chemical compound 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、血糖降下剤、糖尿病予防薬、機能性食品、健
康食品として有用な、番茶又は煎茶中の分子ｌ約４万の
複合多糖類の分離、精製方法に関する。Detailed Description of the Invention (Field of Industrial Application) The present invention provides a complex polysaccharide with a molecular weight of about 40,000 in bancha or sencha, which is useful as a hypoglycemic agent, a diabetes preventive agent, a functional food, and a health food. This invention relates to a method for separating and purifying.
（従来の技術）
本発明者は先に、番茶または煎茶の水抽出液の有機溶媒
処理により、分子量が約４万であって、Ｌアラビノース
、（Ｌ −ａｒａｂｉｎｏｓｅ） 、 Ｄ−リポース
、（Ｄ −ｒｉｂｏｓｅ） 、Ｄ−グルコース（Ｄ −
ｇｌｕｃｏｓｅ ）を主要構成糖とする複合多糖類の分
離、精製に成功し、該複合多糖類乃至該複合多糖類を含
む抽出エキスが、血糖降下剤、糖尿病予防薬、機能性食
品、健康食品として有用なものであることを見出した（
特願昭６２−１３８２０号）。(Prior Art) The present inventor previously treated an aqueous extract of bancha or sencha with an organic solvent to produce L-arabinose, (L-arabinose), D-lipose, (D- ribose), D-glucose (D-
We have succeeded in separating and purifying a complex polysaccharide whose main constituent sugar is glucose (glucose), and the complex polysaccharide or extract containing the complex polysaccharide is useful as a hypoglycemic agent, a diabetes preventive drug, a functional food, and a health food. I found out that it is something (
(Patent Application No. 13820/1982).
（発明が解決しようとする課題）
しかしながら、有機溶媒による抽出、精製は工程が煩雑
で、極めてコストが高く、また残留溶媒の問題等品質管
理ト好ましくない欠点がある。未発明の課題は、かかる
有機溶媒による抽出、精製の欠点を解決し、茶菓より分
子清約４万の複合多糖類を工業的に有効に分離、精製す
る方法を提供することにある。(Problems to be Solved by the Invention) However, extraction and purification using organic solvents involve complicated steps, are extremely expensive, and have drawbacks such as problems with residual solvents, which are undesirable for quality control. The uninvented object is to solve the drawbacks of such extraction and purification using organic solvents and to provide a method for industrially and effectively separating and purifying a complex polysaccharide with a molecular weight of approximately 40,000 from tea confectionery.
（課題を解決するための手段）
即ち１本発明は番茶又は煎茶中の平均分子量が約４×１
０３の複合多糖類を、番茶又は煎茶の水抽出液から限外
濾過により効率的に分画を行おうとするものである。(Means for Solving the Problems) That is, 1. The present invention provides bancha or sencha with an average molecular weight of about 4×1
This is an attempt to efficiently fractionate the complex polysaccharide No. 03 from an aqueous extract of bancha or sencha by ultrafiltration.
限外濾過法自体は、高分子溶液から溶媒および低分子物
質を濾過、除去し、高分子物質を濃縮、精製することが
できる方法として知られているが１本発明者は種々の実
験研究の結果１分画分子量が５×１０〜ｌ０ＸＩＯ及び
８×１０３〜ｌ×１０の、二種類の限外濾過膜を使用す
ることにより、番茶または煎茶の水抽出液中の平均分子
量が約４×１０３の複合多糖類を叛効率良く分画するこ
とができることを見出し、本発明を完成するに至った。The ultrafiltration method itself is known as a method capable of filtering and removing solvents and low-molecular substances from polymer solutions, and concentrating and purifying polymer substances. Result 1: By using two types of ultrafiltration membranes with a molecular weight cut-off of 5 x 10 to 10 The present inventors have discovered that complex polysaccharides can be efficiently fractionated, and have completed the present invention.
本発明に於ては、まず番茶または煎茶の水抽出が行なわ
れる。水抽出は茶菓を適当な温度。In the present invention, first, bancha or sencha is extracted with water. For water extraction, tea is extracted at an appropriate temperature.
例えば０〜８０℃の水に分散し、ｉ！！当な時間、例え
ば１０〜２０分攪拌し、濾過することにより実施される
。For example, when dispersed in water at 0 to 80°C, i! ! This is carried out by stirring for a suitable period of time, for example 10 to 20 minutes, and filtering.
濾液は、必要に応じて減圧蒸留により濃縮することがで
きる。The filtrate can be concentrated by vacuum distillation if necessary.
この番茶の水抽出液を、まず分画分子量が５×１０４〜
ｌ０ＸＩＯの限外濾過膜を用いて濾過し、抽出液中の葉
緑素、蛋白質等の分子量が５×１０〜ｌ０ＸＩＯ以上の
高分子及び繊維状物質などを除去する０次いで得られた
透過液を分画分子量８×１０〜１×１０４の限外Ｉｌ！
過膜を用いて濾過を行う、この処理により、抽出エキス
中のカフェイン、タンニン類、その他の低分子物質が限
外濾過膜を通して透過除去されるが同時に溶媒である木
も除去されるので抽出エキスの濃縮が行なわれるので、
本発明の複合多糖類の濃縮液が得られる。この濃縮液は
、必要にと
応じて凍結乾燥し、乾燥エキスＹすることができる。ま
た、この乾燥エキスは、水に溶解して、透析等の手段に
より更に精製することが可能である。First, the water extract of this bancha has a molecular weight cut-off of 5 x 104 ~
Filter using a 10XIO ultrafiltration membrane to remove macromolecules and fibrous substances with a molecular weight of 5 x 10 to 10XIO or higher, such as chlorophyll and proteins in the extract.Then, the obtained permeate is fractionated. Limit Il with a molecular weight of 8×10 to 1×104!
Filtration is performed using a filtration membrane. Through this process, caffeine, tannins, and other low-molecular substances in the extracted extract are permeated through the ultrafiltration membrane, but at the same time, the wood that is the solvent is also removed. Since the extract is concentrated,
A concentrated solution of the complex polysaccharide of the present invention is obtained. This concentrated liquid can be freeze-dried to obtain a dry extract Y, if necessary. Further, this dried extract can be dissolved in water and further purified by means such as dialysis.
本発明の方法により得られる複合多糖類はＬアラビノー
ス、Ｄ−リポース、Ｄ−グルコースを主要構成糖として
おり、その分子量は約４万である。そして該複合多糖類
に於て、Ｌアラビノース＝Ｄ−リポース：Ｄ−）；ｒル
コースの構成比は ２．９〜３．１ 、２．７〜２．８
：ｌ である。The complex polysaccharide obtained by the method of the present invention has L-arabinose, D-lipose, and D-glucose as its main constituent sugars, and has a molecular weight of about 40,000. In the complex polysaccharide, the composition ratio of L-arabinose = D-lipose: D-); r-lucose is 2.9-3.1, 2.7-2.8
:l.
また、本発明の方法により得られる複合多糖類乃至該複
合多糖類を含むエキスは、血糖降下剤、糖尿病予防薬、
機能性食品、健康食品として有用なものであり、かつ、
日常飲用に供されている茶菓からの抽出物であるから、
ｊＢ性が極めて低く、副作用も殆んど認められず、長期
の連用に於ても人体に何等の悪影響も与えないものであ
る。Further, the complex polysaccharide obtained by the method of the present invention or the extract containing the complex polysaccharide can be used as a hypoglycemic agent, a diabetes preventive agent,
It is useful as a functional food or health food, and
Because it is an extract from tea confectionery that is consumed on a daily basis,
It has extremely low jB properties, almost no side effects are observed, and does not have any adverse effects on the human body even when used for a long period of time.
（実施例）
番茶２０Ｋｇを水２８０交に分散し、６０℃で１５分間
攪拌後、ｔ！過し、濾液を減圧ｅｖｒｊＪＬ、８６文と
した。(Example) 20kg of Bancha was dispersed in 280ml of water, stirred at 60°C for 15 minutes, and then t! The filtrate was reduced to a vacuum of 86 cm.
この抽出エキスを、まず万両分子ｌ１５×１０３’の膜
（膜面積１．Ｑｍ’）を用い、 １００〜＋７０１／ｍ
’ｈｒの′ａ過速度で処理し、抽出エキス８６文を８９
、に限外濾過した後、居留水１６文を加え、さらに２９
．まで限外濾過を行った０次に、万両分子ｊｉ） ｌ
Ｘ １０ （７）膜（１１２而積ｔ、ｏ ｍ’）を用い
、３０〜７０文／ ｍ’ ｈ ｒの透過速度で透過液１
００文を ８文まで濃縮し、更に居留水２３文を加え濃
縮をくり改し、万両分子Ｂｉ〜５×１０３の番茶抽出エ
キス２．５愛を得た。This extracted extract was first applied to a membrane with 10,000 molecules of l15 x 103' (membrane area: 1.Qm') at 100 to +701/m.
Processed with 'hr'a overspeed, extracted extract 86 sentences 89
, after ultrafiltration, add 16 mn of resident water, and then add 29 mn of resident water.
．． The 0th order ultrafiltration is performed until 10,000 molecules ji) l
X 10 (7) using a membrane (112 volumes t, o m'), permeate 1 at a permeation rate of 30 to 70 m/m' hr.
00 mon was concentrated to 8 mon, and further 23 mon of resident water was added and the concentration was repeated to obtain 2.5 Ai of bancha extract with 10,000 molecules Bi~5×103.
得られたエキスを液体クロマトグラフィーで分子ｔ１）
４万前後の複合多糖類の定量を行ったところ、複合多
糖類の濃度は１．３ｚ、回収率は８６．３％であった。The obtained extract was subjected to liquid chromatography to separate molecules t1)
When approximately 40,000 complex polysaccharides were quantified, the concentration of complex polysaccharides was 1.3z, and the recovery rate was 86.3%.
その液体クロマトグラフィーのパターンを第１図に、ま
た茶菓の水抽出後の粗エキスのパターンを第２図にそれ
ぞれ示す。The liquid chromatography pattern is shown in FIG. 1, and the pattern of the crude extract of tea confectionery after water extraction is shown in FIG. 2.
（発明の効果）
本発明の限外濾過による複合多糖類の製造法は、液相に
於ける分離法であるため、相変化を伴なわない省エネル
ギープロセスであり、１０時間に犬Ｊｊの処理を行うこ
とができるため工業的製法としては極めて適切なもので
あり、また複合多糖類の分離と濃縮が同時におこなえる
ので１’： Ｊ’、！が合理的なものであり、かつ有機
溶媒にょる抽出、精製法のように残留溶媒による品質管
理上の問題もないという顕著な効果を奏するものである
。(Effects of the Invention) The method for producing complex polysaccharides by ultrafiltration of the present invention is a separation method in the liquid phase, so it is an energy-saving process that does not involve a phase change. It is extremely suitable as an industrial manufacturing method because it can perform the following steps, and it is also possible to separate and concentrate complex polysaccharides at the same time, so 1': J',! This method is rational and has the remarkable effect of not causing quality control problems due to residual solvents, unlike extraction and purification methods using organic solvents.
第１図は、本発明により得られる複合多糖類の液体クロ
マトグラフィーのパターンを示し。
第２図は茶菓の水抽出後の粗エキスについての液体クロ
マトグラフィーのパターンを示す。
特許出願人 リードケミカル株式会社（ほか２名）；
′
第１図 第２図FIG. 1 shows a liquid chromatography pattern of a complex polysaccharide obtained according to the present invention. Figure 2 shows the liquid chromatography pattern of the crude extract of tea confectionery after water extraction. Patent applicant: Lead Chemical Co., Ltd. (and 2 others);
' Figure 1 Figure 2
Claims (1)
〜１０×１０＾４の限外濾過膜で濾過して葉緑素、繊維
質、蛋白質等の高分子物質を除去した後、得られた透過
液を分画分子量８×１０＾３〜１×１０＾４の限外濾過
膜により濾過してカフェイン、タンニン類、その他の低
分子物質を除去することにより平均分子量が約４×１０
＾４の複合多糖類を分画することを特徴とする複合多糖
類の製造方法The aqueous extract of bancha or sencha with a molecular weight cutoff of 5 x 10^4
After filtering through an ultrafiltration membrane of ~10×10^4 to remove high molecular substances such as chlorophyll, fibers, and proteins, the resulting permeate was filtered with a molecular weight cutoff of 8×10^3 to 1×10^. The average molecular weight is approximately 4 x 10 by removing caffeine, tannins, and other low-molecular substances through ultrafiltration membrane No. 4.
A method for producing a complex polysaccharide characterized by fractionating the complex polysaccharide of ^4
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13463388A JPH01304101A (en) | 1988-06-01 | 1988-06-01 | Preparation of conjugated polysaccharide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13463388A JPH01304101A (en) | 1988-06-01 | 1988-06-01 | Preparation of conjugated polysaccharide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01304101A true JPH01304101A (en) | 1989-12-07 |
Family
ID=15132934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13463388A Pending JPH01304101A (en) | 1988-06-01 | 1988-06-01 | Preparation of conjugated polysaccharide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01304101A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5879733A (en) * | 1996-02-26 | 1999-03-09 | The Procter & Gamble Company | Green tea extract subjected to cation exchange treatment and nanofiltration to improve clarity and color |
| CN102993329A (en) * | 2012-12-31 | 2013-03-27 | 广西师范大学 | Method for comprehensively extracting saponin, polysaccharides and polyphenol from camellia oleifera abel defatted cakes |
| CN103059156A (en) * | 2013-01-06 | 2013-04-24 | 湖南金浩茶油股份有限公司 | Method for extracting tea polysaccharide from tea seed cake |
| JP2014140351A (en) * | 2012-12-27 | 2014-08-07 | Mitsui Norin Co Ltd | Method of manufacturing low-caffeine tea extract, and low-caffeine tea extract |
| WO2017177706A1 (en) * | 2016-04-15 | 2017-10-19 | 深圳大学 | Process for extracting camellia oleifera abel fruit shell polysaccharides |
-
1988
- 1988-06-01 JP JP13463388A patent/JPH01304101A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5879733A (en) * | 1996-02-26 | 1999-03-09 | The Procter & Gamble Company | Green tea extract subjected to cation exchange treatment and nanofiltration to improve clarity and color |
| US6063428A (en) * | 1996-02-26 | 2000-05-16 | The Procter & Gamble Company | Green tea extract subjected to cation exchange treatment and nanofiltration to improve clarity and color |
| US6268009B1 (en) | 1996-02-26 | 2001-07-31 | The Procter & Gamble Company | Green tea extract subjected to cation exchange treatment and nanofiltration to improve clarity and color |
| JP2014140351A (en) * | 2012-12-27 | 2014-08-07 | Mitsui Norin Co Ltd | Method of manufacturing low-caffeine tea extract, and low-caffeine tea extract |
| CN102993329A (en) * | 2012-12-31 | 2013-03-27 | 广西师范大学 | Method for comprehensively extracting saponin, polysaccharides and polyphenol from camellia oleifera abel defatted cakes |
| CN103059156A (en) * | 2013-01-06 | 2013-04-24 | 湖南金浩茶油股份有限公司 | Method for extracting tea polysaccharide from tea seed cake |
| WO2017177706A1 (en) * | 2016-04-15 | 2017-10-19 | 深圳大学 | Process for extracting camellia oleifera abel fruit shell polysaccharides |
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