JPH0475756B2 - - Google Patents
Info
- Publication number
- JPH0475756B2 JPH0475756B2 JP63307947A JP30794788A JPH0475756B2 JP H0475756 B2 JPH0475756 B2 JP H0475756B2 JP 63307947 A JP63307947 A JP 63307947A JP 30794788 A JP30794788 A JP 30794788A JP H0475756 B2 JPH0475756 B2 JP H0475756B2
- Authority
- JP
- Japan
- Prior art keywords
- cells
- shikonin
- hydrophobic
- secondary metabolites
- naphthoquinone
- 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.)
- Expired - Lifetime
Links
- 210000004027 cell Anatomy 0.000 claims description 26
- 241001071917 Lithospermum Species 0.000 claims description 21
- NEZONWMXZKDMKF-JTQLQIEISA-N Alkannin Chemical compound C1=CC(O)=C2C(=O)C([C@@H](O)CC=C(C)C)=CC(=O)C2=C1O NEZONWMXZKDMKF-JTQLQIEISA-N 0.000 claims description 20
- UNNKKUDWEASWDN-UHFFFAOYSA-N alkannin Natural products CC(=CCC(O)c1cc(O)c2C(=O)C=CC(=O)c2c1O)C UNNKKUDWEASWDN-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 241000196324 Embryophyta Species 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 12
- 229930000044 secondary metabolite Natural products 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229930192627 Naphthoquinone Natural products 0.000 claims description 7
- 239000003463 adsorbent Substances 0.000 claims description 7
- 150000002791 naphthoquinones Chemical class 0.000 claims description 6
- 229920002379 silicone rubber Polymers 0.000 claims description 5
- 239000004945 silicone rubber Substances 0.000 claims description 5
- 210000004748 cultured cell Anatomy 0.000 claims description 3
- 238000012258 culturing Methods 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims 4
- 244000172533 Viola sororia Species 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 239000002207 metabolite Substances 0.000 claims 1
- -1 naphthoquinone compound Chemical class 0.000 claims 1
- 229930000223 plant secondary metabolite Natural products 0.000 claims 1
- 229920003225 polyurethane elastomer Polymers 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 5
- 239000000049 pigment Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- 239000011496 polyurethane foam Substances 0.000 description 3
- 238000010923 batch production Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000036560 skin regeneration Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/66—Preparation of oxygen-containing organic compounds containing the quinoid structure
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Description
＜産業上の利用分野＞
本発明は、高分子吸着物質を利用した植物細胞
の二次代謝産物の生産及び分離方法に関するもの
である。
＜従来の技術＞
昔から植物は医薬品類や食品添加物質など人間
が生活を営む上で、いろいろと重要な化学物質を
与えてきた。
1970年代以後、植物細胞の組織培養の技術の発
展とともに植物体自体より植物細胞を分離培養
し、各種有用物質の資源として利用しようとさま
ざまな試みが行われてきた。
その結果、80年代初頭、ナフトキノン系の植物
性色素の一つであるシコニン（Shikonin）を初
めて産業的に生産することができた。
シコニンはリソスパーナム イリスロリゾン
（Lithospermum erythrorhizon）の根のコルク
（cork）層に蓄積される1.4−ナフトキノン（1.4
−naphthoquinone）系の色素である。
このシコニンは、以前はシルクの染色などの染
料として使われたが、最近では火傷や皮膚再生用
の医薬品、あるいはバイオ化粧品の色素原料とし
て最も脚光を浴び、産業的にも以前より重要な物
質であると認められている。
＜本発明が解決しようとする問題点＞
現在、産業的シコニンは主に植物細胞の液沈培
養（submerged cullure）によつて生産されてい
る。
培養された細胞を回受した後、溶媒を使つて細
胞の中に生成されたシコニンが分離される。
このような工程においては主に細胞の中にシコ
ニンが分布されているので、効果的に目的産物を
分離するためには細胞の破壊をともない、その後
培養液へ流出されたシコニンを分離するために多
量の溶媒を処理するなど、工程上の原価上昇の要
因が含まれている。
＜本発明の目的＞
本発明は上記のような欠点を改善するためにな
されたもので、目的産物をより効果的に生産する
方法を提供することを目的とする。
さらに、細胞に損傷を与えることなく培養物か
ら高分子物質で吸着された目的産物だけを簡単に
分離、回受し、溶媒で抽出するといつた工程上の
利点を有する方法を提供することを目的とする。
さらに、回分工程等の培養時間を短縮できるよ
うな方法を提供することを目的とする。
また吸着物質の再使用で一度培養した細胞から
半連続式、あるいは連続式で目的産物の分離生産
が可能な方法を提供することを目的とする。
さらに効果的なナフトキノン類を含む植物細胞
の二次代謝産物の生産原価を下げることができる
方法を提供することを目的とする。
＜本発明の構成＞
この発明を詳しく説明すると次のようになる。
〈イ〉 細胞培養
SHND培地（SHND−medium）を使つて、リ
ソスパーマム イリスロリゾン細胞を殖す。
<Industrial Application Field> The present invention relates to a method for producing and separating secondary metabolites of plant cells using a polymer adsorbent. <Conventional technology> Since ancient times, plants have provided various important chemical substances for human life, such as pharmaceuticals and food additives. Since the 1970s, with the development of plant cell tissue culture technology, various attempts have been made to separate and culture plant cells from the plant itself and use them as resources for various useful substances. As a result, in the early 1980s, it was possible to industrially produce Shikonin, a naphthoquinone-based plant pigment, for the first time. Shikonin is a 1.4-naphthoquinone (1.4
-naphthoquinone) type pigment. Shikonin was previously used as a dye for silk dyeing, but recently it has received the most attention as a pigment raw material for burns, skin regeneration medicine, and bio-cosmetics, and is an industrially more important substance than before. It is acknowledged that there is. <Problems to be Solved by the Present Invention> Currently, industrial shikonin is mainly produced by submerged culturing of plant cells. After the cultured cells are collected, shikonin produced in the cells is separated using a solvent. In such a process, shikonin is mainly distributed within the cells, so in order to effectively separate the target product, the cells must be destroyed, and then the shikonin leaked into the culture medium must be separated. This includes factors that increase costs in the process, such as processing a large amount of solvent. <Objective of the present invention> The present invention was made in order to improve the above-mentioned drawbacks, and an object of the present invention is to provide a method for producing a desired product more effectively. Furthermore, the purpose is to provide a method that has process advantages such as easily separating and recovering only the target product adsorbed by a polymer substance from a culture without damaging cells, and extracting it with a solvent. shall be. Furthermore, it is an object of the present invention to provide a method that can shorten the culture time such as a batch process. Another object of the present invention is to provide a method that allows separation and production of target products from cells once cultured by reusing adsorbed substances in a semi-continuous or continuous manner. Another object of the present invention is to provide a method capable of lowering the production cost of secondary metabolites of plant cells containing more effective naphthoquinones. <Configuration of the Present Invention> The present invention will be described in detail as follows. <B> Cell culture Use SHND medium (SHND-medium) to grow Lithospermum iris lorhizon cells.
【表】【table】
【表】
〈ロ〉 シコニンの生産条件と方法は次のとおり
である。
前記〈イ〉の方法によつて増殖された細胞を洗
つた後、高分子吸着剤が含まれているＭ−９培地
（Ｍ−9medium）でシコニンを吸着分離生産す
る。
Ｍ−９培地の造成と生産条件は次のとおりであ
る。[Table] <B> The production conditions and method of shikonin are as follows. After washing the cells grown by the method (a) above, shikonin is adsorbed and separated using M-9 medium containing a polymer adsorbent. The preparation and production conditions of M-9 medium are as follows.
【表】
〈ハ〉 シコニンの定量および固定
シコニンの定量は培養された細胞の中、あるい
は高分子物質に吸着されたシコニン色素をクロロ
ホルム（chloroform）で抽出した後、減圧蒸発
機でガロロホルムを除き、2.5％水酸化カリウム
（KOH）を加え、発色させた後スペクトロホトメ
タで吸光度（0D622）を測つて標準曲線から比較
定量した。（参考文献：Mizukami，H.et.al，
（1977），Phytochemistry，16：1183−1186）。
シコニンの固定は抽出した試料をシリカゲル
（silicagel）板に点滴しクロロホルムを可動状に
して、薄層のクロマトグラフイー法（Thin
layer chromatography）によつて行つた。
ここで標準試料はアセチルシコニン
（acetylshiconin）を使つた。
この方法によると生産された試料のクロマトグ
ラフ上のRf値はは標準試料のアセチルシコニン
のRf値と同じ所にあり、その外Rf値と少し差の
ある４つの僅かな跡が発見できたが、これらはシ
コニン誘導体であることがわかつた。
これは質量スペクトロメトリー（Mass
spectrometry）分析方法によつても再び確認さ
れた。
実施例 １
吸着剤としてのポリウレタンフオーム
（Polyurethan foam）を使つた場合（表−１）
市中で手軽に求めることのできるポリウレタン
フオーム（座布団スポンジ）を直径１cm以内の適
当な大きさで切つて、SHND培地で殖した細胞
と一緒にＭ−９培地で回分式半連続式、あるいは
連続式で培養すると細胞の増殖とともに生成され
たシコニンの大部分がポリウレタンに吸着され
る。
培地より分離されたポリウレタンフオームから
吸着されたクロロホルム（chloroform）で抽出
して表１の結果を得た。[Table] 〈C〉 Quantification and fixation of shikonin To quantify shikonin, extract the shikonin pigment in cultured cells or adsorbed to a polymer substance with chloroform, and then remove galloroform in a vacuum evaporator. After adding 2.5% potassium hydroxide (KOH) to develop color, the absorbance (0D 622 ) was measured using a spectrophotometer and comparative quantification was performed using a standard curve. (References: Mizukami, H.et.al,
(1977), Phytochemistry, 16:1183-1186). To fix shikonin, the extracted sample is dripped onto a silica gel plate to make chloroform mobile, and the thin layer chromatography method (Thin
layer chromatography). Here, acetylshiconin was used as the standard sample. According to this method, the Rf value on the chromatograph of the sample produced was at the same location as the Rf value of acetylshikonine in the standard sample, and four slight traces were found that were slightly different from the Rf value. , these were found to be shikonin derivatives. This is mass spectrometry (Mass
This was confirmed again using spectrometry analysis. Example 1 When using polyurethane foam as an adsorbent (Table 1) Polyurethane foam (cushion sponge), which can be easily obtained in the market, was cut to an appropriate size with a diameter of 1 cm or less. When cells grown in SHND medium are cultured in M-9 medium in a batch, semi-continuous or continuous manner, most of the shikonin produced as the cells proliferate is adsorbed to polyurethane. The results shown in Table 1 were obtained by extraction with chloroform adsorbed from the polyurethane foam separated from the medium.
【表】【table】
【表】
実施例 ２
吸着剤としてのシリコンラバー（silicone
rubber）を使つた場合（表−２）
シリコンラバー（商品名：マスターフレツクス
（Masterflex）、アメリカ、コウルパーマー
（Cole Permer）社の製品）を適当な大きさで切
つて、SHND培地で殖された細胞と一緒にＭ−
９培地で回分式、半連続式あるいは連続式で培養
すると細胞の増殖とともに生成されたシコニンの
大部分がシリコンラバーに吸着される。
シリコンラバーに吸着されたシコニンをクロロ
ホルムで抽出して表２の結果が得られた。[Table] Example 2 Silicone rubber as an adsorbent
(Table 2) Silicone rubber (trade name: Masterflex, a product of Cole Permer, USA) was cut to an appropriate size and grown in SHND medium. M- together with the cells
When cultured in 9 medium in a batch, semi-continuous or continuous manner, most of the shikonin produced as the cells proliferate is adsorbed to the silicone rubber. Shikonin adsorbed on silicone rubber was extracted with chloroform and the results shown in Table 2 were obtained.
【表】【table】
【表】
＜本発明の効果＞
この発明は植物細胞の培養時に、適当な高分子
吸着物質を加え、目的産物のシコニンを含むナフ
トキノン類物質の細胞外への流出を誘導した後、
この高分子物質に効果的に吸着させることで植物
細胞に対する生産物阻害（product inhibition）
を減らすものである。
さらにこの発明は生物反応器でムラサキ科に属
するリソスパーマム イリスロリゾン
（Lithospermum erythrorhizon）などの植物細
胞を大量に培養し、シコニンを含むナフトキノン
類の植物の二次代謝産物を生産する際に、疎水性
高分子吸着物質を利用し、生産目的物の分離、回
受を易しくすることはいわずもがな、植物細胞自
体の二次代謝産物の生産能力を向上させる方法に
関したものでもある。
その結果、目的産物をより効果的に生産するこ
とができるようになる。
さらに、細胞に損傷を与えることなく培養物か
ら高分子物質へ吸着された目的産物だけを簡単に
分離、回受し、溶媒で抽出するといつた工程上の
利点とともに、回分工程時の培養時間を短縮でき
るなど、多目的の効果を期待することができると
いつた特徴をもつている。
また吸着物質の再使用で一度培養した細胞から
半連続式、あるいは連続式で目的産物の分離生産
が可能という点も大きい利点といえる。
さらにこの発明はこのような工程上の利点を提
供し、それによつて効果的なナフトキノン類を含
む植物細胞の二次代謝産物の生産原価を下げるこ
とができるものである。[Table] <Effects of the present invention> In the present invention, when culturing plant cells, an appropriate polymeric adsorbent is added to induce the outflow of naphthoquinone substances containing the target product shikonin out of the cells.
By effectively adsorbing to this polymer substance, product inhibition occurs in plant cells.
It is intended to reduce Furthermore, this invention cultivates a large amount of plant cells such as Lithospermum erythrorhizon, which belongs to the family Murasaceae, in a bioreactor, and when producing secondary metabolites of naphthoquinone plants, including shikonin, hydrophobic polymer It goes without saying that the use of adsorbent substances to facilitate the separation and recovery of products to be produced is also a method for improving the secondary metabolite production capacity of plant cells themselves. As a result, the desired product can be produced more effectively. Furthermore, in addition to process advantages such as the ability to easily separate and recycle only the target product adsorbed onto the polymeric material from the culture without damaging the cells, and extracting it with a solvent, the cultivation time during the batch process can be reduced. It has the characteristic that it can be expected to have a multipurpose effect, such as being able to shorten the time. Another great advantage is that by reusing adsorbed substances, it is possible to separate and produce the target product from cells once cultured in a semi-continuous or continuous manner. Furthermore, the present invention provides such process advantages, thereby reducing the cost of producing plant cell secondary metabolites, including effective naphthoquinones.
Claims (1)
において、代謝産物の吸着物質としてポリウレタ
ンやシリコンラバなど関連疎水性高分子物質の中
で一つ以上を用いて植物培養細胞が生産する疎水
性のナフトキノン系二次代謝産物の細胞外への流
出を誘導、あるいは促進させることで疎水性二次
代謝産物の生産性を増加させる方法。 ２ 特許請求の範囲第１項で生産される疎水性二
次代謝産物の一部または全部を第１項の高分子物
質に吸着させ、回分式、半連続式あるいは連続式
で分離、生産する方法。 ３ 植物の二次代謝産物中でシコニンを含むナフ
トキノン系の化合物であることを特徴とする特許
請求の範囲第１項または第２項記載の方法。[Scope of Claims] 1. In the production of secondary metabolites by culturing purple violet cells, cultured plant cells use one or more of related hydrophobic polymeric substances such as polyurethane and silicone rubber as an adsorbent for metabolites. A method of increasing the productivity of hydrophobic secondary metabolites by inducing or promoting the outflow of hydrophobic naphthoquinone-based secondary metabolites to the outside of cells. 2. A method for separating and producing a part or all of the hydrophobic secondary metabolite produced in claim 1 on the polymeric substance of claim 1 in a batch, semi-continuous or continuous manner. . 3. The method according to claim 1 or 2, which is a naphthoquinone compound containing shikonin among plant secondary metabolites.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1988P12155 | 1988-09-20 | ||
| KR1019880012155A KR900005770B1 (en) | 1988-09-20 | 1988-09-20 | Producing and isolations method of plant cell 2th product for using absorption substance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0286773A JPH0286773A (en) | 1990-03-27 |
| JPH0475756B2 true JPH0475756B2 (en) | 1992-12-01 |
Family
ID=19277884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63307947A Granted JPH0286773A (en) | 1988-09-20 | 1988-12-07 | Production and separation of secondary metabolite of plant cell utilizing polymer adsorbing substance |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH0286773A (en) |
| KR (1) | KR900005770B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006223202A (en) * | 2005-02-18 | 2006-08-31 | Toyo Univ | Plant secondary metabolite adsorbent and method for recovering plant cell secondary metabolite |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6253699B2 (en) * | 1973-05-02 | 1987-11-11 | Bosch Gmbh Robert |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0226320Y2 (en) * | 1985-09-24 | 1990-07-18 |
-
1988
- 1988-09-20 KR KR1019880012155A patent/KR900005770B1/en not_active IP Right Cessation
- 1988-12-07 JP JP63307947A patent/JPH0286773A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6253699B2 (en) * | 1973-05-02 | 1987-11-11 | Bosch Gmbh Robert |
Also Published As
| Publication number | Publication date |
|---|---|
| KR900004941A (en) | 1990-04-13 |
| KR900005770B1 (en) | 1990-08-11 |
| JPH0286773A (en) | 1990-03-27 |
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