JP7496743B2 - Method for extracting cis-xanthophyll - Google Patents
Method for extracting cis-xanthophyll Download PDFInfo
- Publication number
- JP7496743B2 JP7496743B2 JP2020150294A JP2020150294A JP7496743B2 JP 7496743 B2 JP7496743 B2 JP 7496743B2 JP 2020150294 A JP2020150294 A JP 2020150294A JP 2020150294 A JP2020150294 A JP 2020150294A JP 7496743 B2 JP7496743 B2 JP 7496743B2
- Authority
- JP
- Japan
- Prior art keywords
- isomerization
- xanthophyll
- isothiocyanate
- extraction
- adonirubin
- 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.)
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Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、キサントフィルを豊富に含む微生物等から、異性化触媒を用いてキサントフィルを効率良く抽出する方法に関する。 The present invention relates to a method for efficiently extracting xanthophyll from microorganisms that are rich in xanthophyll, using an isomerization catalyst.
キサントフィルは、黄色から赤色または紫色に及ぶ自然界に広く存在するポリエン色素であり、8個のイソプレン単位が結合して構成された炭素数40の基本骨格を持つ化合物群である。キサントフィルはカロテノイドの一種であり、分子内にアルコール、ケトン、エポキシなどの酸素原子を有する官能基を含む極性化合物である。カロテノイドにはキサントフィルの他にカロテンも含まれるが、カロテンは炭素原子と水素原子からなる炭化水素系化合物(酸素原子は含まない非極性化合物)であり、キサントフィルとは性質が異なることが知られている。 Xanthophylls are polyene pigments found widely in nature, ranging in color from yellow to red or purple, and are a group of compounds with a basic skeleton of 40 carbon atoms composed of eight bonded isoprene units. Xanthophylls are a type of carotenoid, a polar compound containing functional groups with oxygen atoms, such as alcohol, ketone, and epoxy, in the molecule. In addition to xanthophylls, carotenoids also include carotene, but carotene is a hydrocarbon compound (non-polar compound that does not contain oxygen atoms) made up of carbon and hydrogen atoms, and is known to have different properties from xanthophylls.
キサントフィルは、魚類、鶏卵の色揚げ剤、食品添加物、油脂加工食品、タンパク質性食品、水性液状食品などに幅広く使用されており、さらに、フリーラジカルによって誘起される脂質の過酸化に対する抗酸化活性、α-トコフェロールの数百倍に達する一重項酸素消去作用などから、その強力な抗酸化活性を生かした機能性食品、化粧品、または医薬品としての用途が期待されている。 Xanthophyll is widely used in fish and eggs, as a color enhancer, food additive, processed oil and fat foods, protein foods, and aqueous liquid foods. Furthermore, due to its antioxidant activity against lipid peroxidation induced by free radicals and its singlet oxygen quenching effect that is several hundred times stronger than that of α-tocopherol, it is expected to be used in functional foods, cosmetics, and pharmaceuticals that take advantage of its strong antioxidant activity.
こうした背景から、藻類や微生物を用いてキサントフィルを抽出する方法が報告されている。例えば、キサントフィルを産生する微生物の培養物を、80℃以上の低級アルコール類、または80℃以上の水と低級アルコール類との組み合わせで抽出する方法(特許第4969370号:特許文献1)などが知られている。 In light of this, methods have been reported for extracting xanthophyll using algae or microorganisms. For example, a method is known in which a culture of a microorganism that produces xanthophyll is extracted with lower alcohols at 80°C or higher, or with a combination of water at 80°C or higher and lower alcohols (Patent No. 4969370: Patent Document 1).
また、キサントフィルには幾何異性体としてシス型異性体やトランス型異性体が存在し、シス型キサントフィルはトランス型キサントフィルより溶媒への溶解度が高い傾向があることが知られている。キサントフィルをシス体に異性化する方法に関し、アスタキサンチンを熱処理によりシス体に異性化することが報告されている(Honda et al., Eur. J. Lipid Sci. Technol., 2018, 120, 1800191(1-8):非特許文献1)。しかしながら、アスタキサンチン等のキサントフィルは熱に弱く、加熱により一部分解し回収率が低下することから、熱処理以外の工程によりシス型キサントフィルを得る方法が求められていた。 In addition, xanthophylls exist as geometric isomers, cis-isomers and trans-isomers, and it is known that cis-xanthophylls tend to have higher solubility in solvents than trans-xanthophylls. Regarding a method for isomerizing xanthophylls into cis-isomers, it has been reported that astaxanthin can be isomerized into cis-isomers by heat treatment (Honda et al., Eur. J. Lipid Sci. Technol., 2018, 120, 1800191(1-8): Non-Patent Document 1). However, xanthophylls such as astaxanthin are sensitive to heat and partially decompose when heated, resulting in a decrease in recovery rate. Therefore, a method for obtaining cis-xanthophylls by a process other than heat treatment has been desired.
熱処理以外でカロテノイドをシス体に異性化する方法として、リコピンを異性化触媒によりシス体に異性化させること(Honda et al., Sci. Rep., 2019, 9, 7979(1-7):非特許文献2)が報告されているが、非極性化合物であるリコピン(カロテン)は極性化合物であるキサントフィルとは性質が異なる。また、極性や立体構造から、リコピンはキサントフィルよりシス異性化しやすい。上記背景から当該手法では、キサントフィルを効率よくシス体に異性化できるか不明であった。 As a method for isomerizing carotenoids to the cis form other than by heat treatment, isomerization of lycopene to the cis form using an isomerization catalyst has been reported (Honda et al., Sci. Rep., 2019, 9, 7979(1-7): Non-Patent Document 2). However, lycopene (carotene), a non-polar compound, has different properties from xanthophyll, a polar compound. In addition, due to its polarity and three-dimensional structure, lycopene is more likely to be isomerized to the cis form than xanthophyll. Given the above background, it was unclear whether this method could efficiently isomerize xanthophyll to the cis form.
本発明の解決しようとする課題は、キサントフィルを温和な条件下で効率良くシス体に異性化し、抽出率を高めることで、微生物等の原料からキサントフィルを効率良く製造することである。 The problem that the present invention aims to solve is to efficiently produce xanthophyll from raw materials such as microorganisms by efficiently isomerizing xanthophyll to the cis form under mild conditions and increasing the extraction rate.
本発明者は、上記課題を解決するために鋭意検討を行った結果、キサントフィルを含む原料を異性化触媒で処理することにより、原料に含まれるトランス型キサントフィルを温和な条件下で効率良くシス型キサントフィルに異性化し、抽出率を高めることに成功し、本発明を完成するに至った。 As a result of intensive research into solving the above problems, the inventors of the present invention succeeded in efficiently isomerizing trans-xanthophyll contained in a raw material containing xanthophyll to cis-xanthophyll under mild conditions by treating the raw material with an isomerization catalyst, thereby increasing the extraction rate, and thus completing the present invention.
すなわち、本発明は以下の通りである。
(1)トランス型キサントフィルを含有する原料を異性化触媒で処理することにより、前記トランス型キサントフィルをシス型キサントフィルに異性化する方法。
(2)トランス型キサントフィルを含有する原料を異性化触媒で処理することにより、前記トランス型キサントフィルをシス型キサントフィルに異性化することを特徴とする、キサントフィルの抽出方法。
(3)トランス型キサントフィルが、細菌、酵母、藻類または植物由来のものである(1)または(2)に記載の方法。
(4)細菌がパラコッカス属に属するものである(3)に記載の方法。
(5)異性化触媒が、イソチオシアネート、ポリスルフィド、金属塩化物およびヨウ素からなる群から選択される少なくとも1つである、(1)~(4)のいずれか1項に記載の方法。
(6)イソチオシアネートが、メチルイソチオシアネート、エチルイソチオシアネート、アリルイソチオシアネート、およびベンジルイソチオシアネートからなる群から選択される少なくとも1つである(5)に記載の方法。
(7)ポリスルフィドが、ジアリルジスルフィドおよびジメチルトリスルフィドからなる群から選択される少なくとも1つである(5)に記載の方法。
(8)金属塩化物が、塩化銅および塩化鉄からなる群から選択される少なくとも1つである(5)に記載の方法。
(9)前記異性化触媒で処理する工程による異性化効率が1.1倍以上である、(1)~(8)のいずれか1項に記載の方法。
(10)イソチオシアネート、ポリスルフィド、金属塩化物およびヨウ素からなる群から選択される少なくとも1つを含む、トランス型キサントフィルのシス型キサントフィルへの異性化触媒。
(11)イソチオシアネート、ポリスルフィド、または金属塩化物が、メチルイソチオシアネート、エチルイソチオシアネート、アリルイソチオシアネート、ベンジルイソチオシアネート、ジアリルジスルフィド、ジメチルトリスルフィド、塩化銅、および塩化鉄からなる群から選択される少なくとも1つである(10)に記載の異性化触媒。
That is, the present invention is as follows.
(1) A method for isomerizing a raw material containing trans-xanthophyll to cis-xanthophyll by treating the raw material with an isomerization catalyst.
(2) A method for extracting xanthophyll, comprising treating a raw material containing trans-xanthophyll with an isomerization catalyst to isomerize the trans-xanthophyll to cis-xanthophyll.
(3) The method according to (1) or (2), wherein the trans-xanthophyll is derived from bacteria, yeast, algae or plants.
(4) The method according to (3), wherein the bacterium belongs to the genus Paracoccus.
(5) The method according to any one of (1) to (4), wherein the isomerization catalyst is at least one selected from the group consisting of isothiocyanates, polysulfides, metal chlorides, and iodine.
(6) The method according to (5), wherein the isothiocyanate is at least one selected from the group consisting of methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, and benzyl isothiocyanate.
(7) The method according to (5), wherein the polysulfide is at least one selected from the group consisting of diallyl disulfide and dimethyl trisulfide.
(8) The method according to (5), wherein the metal chloride is at least one selected from the group consisting of copper chloride and iron chloride.
(9) The method according to any one of (1) to (8), wherein the isomerization efficiency in the step of treating with the isomerization catalyst is 1.1 times or more.
(10) A catalyst for isomerizing trans-xanthophyll to cis-xanthophyll, comprising at least one selected from the group consisting of isothiocyanate, polysulfide, metal chloride, and iodine.
(11) The isomerization catalyst according to (10), wherein the isothiocyanate, polysulfide, or metal chloride is at least one selected from the group consisting of methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, benzyl isothiocyanate, diallyl disulfide, dimethyl trisulfide, copper chloride, and iron chloride.
本発明により、高効率かつ温和な条件下で原料中のトランス型キサントフィルをシス型キサントフィルに異性化することでキサントフィルの抽出率を高め、キサントフィルを効率的に抽出することが可能となる。 The present invention makes it possible to increase the extraction rate of xanthophyll by isomerizing trans-xanthophyll in the raw material to cis-xanthophyll under highly efficient and mild conditions, thereby enabling efficient extraction of xanthophyll.
本発明の範囲はこれらの説明に拘束されることはなく、以下の例示以外についても、本発明の趣旨を損なわない範囲で適宜変更し実施し得る。
本発明は、キサントフィルを含有する原料からキサントフィルを溶媒抽出する際、ポリスルフィドやイソチオシアネートなどを異性化触媒として加えることで、温和な条件下で効率よくトランス型キサントフィルを異性化し、高効率でキサントフィルを抽出することが可能となる。
The scope of the present invention is not limited to these descriptions, and other than the following examples, the present invention can be modified and implemented as appropriate without departing from the spirit of the present invention.
In the present invention, when xanthophyll is extracted with a solvent from a raw material containing xanthophyll, polysulfide, isothiocyanate, or the like is added as an isomerization catalyst, thereby making it possible to efficiently isomerize trans-xanthophyll under mild conditions and extract xanthophyll with high efficiency.
本発明の対象となるキサントフィルとしては、アスタキサンチン、カンタキサンチン、アドニルビン、アドニキサンチン、βクリプトキサンチン、ゼアキサンチン、ルテイン、エキネノン、3-ヒドロキシエキネノン、アステロイデノン、β-アポ-8’-カロテナール、ラクツカキサンチン、ツナキサンチン、カプサンチン、カプソルビン、ビオラキサンチン、ネオキサンチン、フコキサンチン、シフォナキサンチン、アンテラキサンチン、シトラナキサンチン、フコキサンチノール、アマロウシアキサンチンA、ハロシンチアキサンチン、ジアトキサンチン、ペリジニン、スピリロキサンチン、ルビキサンチン、ロドキサンチン、アロキサンチン等が挙げられる。本発明においては、アスタキサンチン、アドニルビン、アドニキサンチン、βクリプトキサンチン、ゼアキサンチン、ルテイン、エキネノン、3-ヒドロキシエキネノンおよびアステロイデノンなどが好ましく用いられる。上記キサントフィルのうち、カンタキサンチン、ルテイン、β-クリプトキサンチン、およびゼアキサンチンの構造を以下に示す。 Xanthophylls that are the subject of the present invention include astaxanthin, canthaxanthin, adonirubin, adonixanthin, β-cryptoxanthin, zeaxanthin, lutein, echinenone, 3-hydroxyechinenone, asteroidenone, β-apo-8'-carotenal, lactucaxanthin, tunaxanthin, capsanthin, capsorubin, violaxanthin, neoxanthin, fucoxanthin, siphonaxanthin, antheraxanthin, citranaxanthin, fucoxanthinol, amarousiaxanthin A, halocynthiaxanthin, diatoxanthin, peridinin, spirilloxanthin, rubixanthin, rhodoxanthin, and alloxanthin. In the present invention, astaxanthin, adonirubin, adonixanthin, β-cryptoxanthin, zeaxanthin, lutein, echinenone, 3-hydroxyechinenone, asteroidenone, and the like are preferably used. Among the above xanthophylls, the structures of canthaxanthin, lutein, β-cryptoxanthin, and zeaxanthin are shown below.
アスタキサンチン、アドニルビン、およびアドニキサンチンについて、シス体およびトランス体の構造を以下に示す。
上記構造式(A)~(E)の化合物のうち、(A)~(C)がトランス体であり、(D)~(E)がシス体である。具体的には、(A)はトランス型のアスタキサンチンであり、(B)はトランス型のアドニルビンであり、(C)はトランス型のアドニキサンチンである。また、(D)および(E)はシス型のアスタキサンチンである。上記構造式のように、キサントフィルは分子の末端にケト基や水酸基などの極性基を有するため、極性基を持たないカロテンに比べ、立体的障害および静電相互作用の点から、シス型キサントフィルに異性化しにくい。また、シス型キサントフィルは折れ曲がった構造をしていることから、熱や光等により分解しやすく、最終的な製造効率が低下することが知られている。本発明において、異性化触媒を用いることにより、トランス型キサントフィルを温和な条件下で効率良くシス体に異性化することが可能となり、抽出率の向上に成功した。 Of the compounds of the above structural formulas (A) to (E), (A) to (C) are trans-isomers, and (D) to (E) are cis-isomers. Specifically, (A) is trans-astaxanthin, (B) is trans-adonirubin, and (C) is trans-adonixanthin. Also, (D) and (E) are cis-astaxanthin. As shown in the above structural formula, xanthophyll has polar groups such as keto groups and hydroxyl groups at the ends of the molecule, so it is less likely to be isomerized to cis-xanthophyll due to steric hindrance and electrostatic interactions compared to carotene, which does not have polar groups. In addition, since cis-xanthophyll has a bent structure, it is known to be easily decomposed by heat, light, etc., and the final production efficiency is reduced. In the present invention, by using an isomerization catalyst, it is possible to efficiently isomerize trans-xanthophyll to cis-isomers under mild conditions, and the extraction rate has been successfully improved.
本発明において、キサントフィルを含有する原料は特に限定されるものではなく、任意のものを使用することができる。例えば、細菌、酵母、藻類、動植物由来のものが挙げられる(下記)。
細菌:パラコッカス(Paracoccus)属、アグロバクテリウム(Agrobacterium)属、ブレビバクテリウム(Brevibacterium)属、ブレバンディモナス(Brevundimonas)属、またはエリスロバクター(Erythrobacter)属に属する細菌等。
酵母:ファフィア(Phaffia)属、ヤロウィア属(Yarrowia)属、ロドスポリデウム(Rhodosporidium)属、スポリデオボルス(Sporidiobolus)属、またはキサントフィロミセス(Xanthophyllomyces)属に属する酵母等。
In the present invention, the raw material containing xanthophyll is not particularly limited, and any raw material can be used, for example, those derived from bacteria, yeast, algae, animals and plants (described below).
Bacteria: bacteria belonging to the genus Paracoccus, Agrobacterium, Brevibacterium, Brevundimonas, or Erythrobacter, and the like.
Yeast: yeasts belonging to the genus Phaffia, Yarrowia, Rhodosporidium, Sporidiobolus, or Xanthophyllomyces, and the like.
藻類:ヘマトコッカス(Haematococcus)属、アオサ(Ulva)属、クロレラ(Chlorella)属、ドナリエラ(Dunaliella)属、オーランチオキトリウム(Aurantiochytrium)属、ピンギオクリシス(Pinguiochrysis)属、オクロモナス(Ochromonas)属、ファエオダクチラム(Phaeoductylum)属、プレウロクリシス(Pleurochrysis)属、キートセロス(Chaetoceros)属、パブロバ(Pavlova)属、オキナワモズク(Cladosiphon)属、ホンダワラ(Sargassum)属、ワカメ(Undaria)属、クラミドモナス(Chlamydomonas)属、スピルリナ(Spirulina)属、アルスロスピラ(Arthrospira)属、ミル(Codium)属、ミドリムシ(Euglena)属またはシンビオディウム(Symbiodinium)属に属する藻類等。 Algae: Haematococcus genus, Ulva genus, Chlorella genus, Dunaliella genus, Aurantiochytrium genus, Pinguiochrysis genus, Ochromonas genus, Phaeodactylum genus, Pleurochrysis genus, Chaetoceros genus, Algae belonging to the genus Chaetoceros, Pavlova, Cladosiphon, Sargassum, Undaria, Chlamydomonas, Spirulina, Arthrospira, Codium, Euglena, or Symbiodinium, etc.
動植物:緑黄色野菜 (カボチャ、ニンジン、アシタバ、コマツナ、シソ、ホウレンソウ、トウモロコシ、パプリカ等)、果実(マンゴー、パパイヤ、柿、あんず、柑橘類、クコ、ローズヒップ等)、花(マリーゴールド、アドニス等)、エビ、カニ、いくら、オキアミ、卵等。 Flora and fauna: green and yellow vegetables (pumpkin, carrot, angelica tree, komatsuna, shiso, spinach, corn, paprika, etc.), fruits (mango, papaya, persimmon, apricot, citrus fruits, wolfberry, rose hips, etc.), flowers (marigold, adonis, etc.), shrimp, crab, salmon roe, krill, eggs, etc.
上記のような原料からキサントフィルを抽出する際に用いる溶媒としては、低級アルコール類、ケトン系溶媒、炭化水素系溶媒が用いられ、低級アルコール類、ケトン系溶媒が好ましく用いられる。低級アルコール類としては、エタノール、メタノール、およびイソプロパノールが好ましく用いられ、エタノールが特に好ましく用いられる。ケトン系溶媒としては、アセトン、酢酸エチルが好ましく用いられる。炭化水素系溶媒としてはn-ヘキサン、シクロヘキサンが好ましく用いられる。また、超臨界二酸化炭素等を使用することもできる。 As the solvents used when extracting xanthophyll from the above-mentioned raw materials, lower alcohols, ketone solvents, and hydrocarbon solvents are used, with lower alcohols and ketone solvents being preferred. As the lower alcohols, ethanol, methanol, and isopropanol are preferred, with ethanol being particularly preferred. As the ketone solvents, acetone and ethyl acetate are preferred. As the hydrocarbon solvents, n-hexane and cyclohexane are preferred. Supercritical carbon dioxide, etc. can also be used.
本発明においては、トランス型キサントフィルを含有する原料を上記溶媒に分散させ、さらに異性化触媒を加えることでシス体へ異性化し、キサントフィル、すなわちシス体からなるキサントフィル、又はシス体とトランス体との混合物を含むキサントフィルを溶媒中に抽出する。抽出時の溶媒の温度は、使用する溶媒の沸点にもよるが、下限値は、10℃、20℃、30℃、40℃または50℃であり、上限値は、70℃、80℃、90℃、100℃、110℃、120℃または130℃である。これらの温度範囲から、抽出時の溶媒の温度を適宜設定することができる。例えば、抽出時の溶媒の温度は、10℃~150℃、30℃~130℃、40℃~100℃、50℃~70℃である。 In the present invention, a raw material containing trans-xanthophyll is dispersed in the above-mentioned solvent, and an isomerization catalyst is added to isomerize the trans-xanthophyll to the cis-isomer, and xanthophyll, i.e., xanthophyll consisting of the cis-isomer or xanthophyll containing a mixture of the cis-isomer and the trans-isomer, is extracted into the solvent. The temperature of the solvent during extraction depends on the boiling point of the solvent used, but the lower limit is 10°C, 20°C, 30°C, 40°C, or 50°C, and the upper limit is 70°C, 80°C, 90°C, 100°C, 110°C, 120°C, or 130°C. The temperature of the solvent during extraction can be appropriately set from these temperature ranges. For example, the temperature of the solvent during extraction is 10°C to 150°C, 30°C to 130°C, 40°C to 100°C, or 50°C to 70°C.
異性化触媒としては、イソチオシアネート、ポリスルフィド、金属塩化物、およびヨウ素からなる群から選択される少なくとも1つが挙げられる。イソチオシアネートとしては、例えばメチルイソチオシアネート、エチルイソチオシアネート、アリルイソチオシアネート、ベンジルイソチオシアネート、ブチルイソチオシアネート、スルフォラファンが用いられ、メチルイソチオシアネート、エチルイソチオシアネート、アリルイソチオシアネート、ベンジルイソチオシアネート、スルフォラファンが好ましく、アリルイソチオシアネート、ベンジルイソチオシアネート、スルフォラファンがさらに好ましく用いられる。ポリスルフィドとしては、例えばジアリルジスルフィド、ジメチルトリスルフィド、ジアリルトリスルフィド、ジアリルテトラスルフィドが用いられ、ジアリルジスルフィド、ジメチルトリスルフィドが好ましく用いられる。 The isomerization catalyst may be at least one selected from the group consisting of isothiocyanates, polysulfides, metal chlorides, and iodine. As the isothiocyanates, for example, methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, benzyl isothiocyanate, butyl isothiocyanate, and sulforaphane are used, with methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, benzyl isothiocyanate, and sulforaphane being preferred, and allyl isothiocyanate, benzyl isothiocyanate, and sulforaphane being more preferred. As the polysulfides, for example, diallyl disulfide, dimethyl trisulfide, diallyl trisulfide, and diallyl tetrasulfide are used, with diallyl disulfide and dimethyl trisulfide being preferred.
金属塩化物としては、塩化銅(II)、塩化鉄(III)が好ましく用いられる。これらの異性化触媒は、抽出溶媒中に添加して使用することができる。異性化触媒の添加量(濃度)は特に限定されるものではないが、下限値は、0.1mM、0.5mM、1mM、5mM、10mM、20mM、30mM、40mMまたは50mMであり、上限値は、100mM、200mM、300mM、400mM、500mM、600mM、700mM、800mM、900mMまたは1000mMである。これらの範囲から、異性化触媒の添加量を適宜設定することができる。例えば0.1mM~1000mM、1mM~800mM、10mM~600mM、20mM~500mM、30mM~400mM、50mM~400mMである。 As the metal chloride, copper (II) chloride and iron (III) chloride are preferably used. These isomerization catalysts can be added to the extraction solvent. The amount (concentration) of the isomerization catalyst added is not particularly limited, but the lower limit is 0.1 mM, 0.5 mM, 1 mM, 5 mM, 10 mM, 20 mM, 30 mM, 40 mM or 50 mM, and the upper limit is 100 mM, 200 mM, 300 mM, 400 mM, 500 mM, 600 mM, 700 mM, 800 mM, 900 mM or 1000 mM. The amount of the isomerization catalyst added can be appropriately set from these ranges. For example, 0.1 mM to 1000 mM, 1 mM to 800 mM, 10 mM to 600 mM, 20 mM to 500 mM, 30 mM to 400 mM, and 50 mM to 400 mM.
本発明において原料として微生物を用いる場合は、培養液を遠心分離などの一般的に知られている濾過方法に供することによって得られた湿菌体を用いることができる。この湿菌体を噴霧乾燥、流動乾燥、回転ドラム式乾燥または凍結乾燥など一般的に知られる乾燥方法によって乾燥させることによって、乾燥菌体を得、原料として使用することも可能である。 When a microorganism is used as a raw material in the present invention, wet bacterial cells obtained by subjecting the culture solution to a commonly known filtration method such as centrifugation can be used. The wet bacterial cells can be dried by a commonly known drying method such as spray drying, fluidized bed drying, rotary drum drying, or freeze drying to obtain dried bacterial cells, which can be used as a raw material.
溶媒の量としては、原料中に含まれるキサントフィル量を溶解できる量であれば良い。例えば、原料が乾燥菌体であり、低級アルコール類を用いて抽出する場合、溶媒量は、乾燥菌体内に含まれるキサントフィル1g に対して、下限値は100g、200g、300g、400gまたは500gであり、上限値は1000g、2000g、2500g、3000g、3200g、3400g、3500g、3600g、3800g、4000g、4500g、5000g、5500gまたは6000gである。これらの範囲から、溶媒量を適宜設定することができる。例えば、100g~6000g 、200g~4000g、300g~3200g、400g~2500gである。 The amount of solvent may be an amount that can dissolve the amount of xanthophyll contained in the raw material. For example, when the raw material is dried fungus cells and extraction is performed using lower alcohols, the amount of solvent is 100g, 200g, 300g, 400g, or 500g per 1g of xanthophyll contained in the dried fungus cells, with the lower limit being 1000g, 2000g, 2500g, 3000g, 3200g, 3400g, 3500g, 3600g, 3800g, 4000g, 4500g, 5000g, 5500g, or 6000g. The amount of solvent can be appropriately set within these ranges. For example, 100g to 6000g, 200g to 4000g, 300g to 3200g, or 400g to 2500g.
本発明においては、特に、増殖速度の速さ、キサントフィルの生産性から、16SリボソームRNAに対応するDNAの塩基配列が配列番号1に記載の塩基配列と実質的に相同である細菌が好ましく用いられる。「実質的に相同である」とは、DNAの塩基配列決定のエラー頻度等を考慮し、配列が、例えば94%以上、96%以上、98%以上の相同性を有することを意味する。このような細菌としては、特にE-396株(FERM BP-4283)が好ましい。また、E-396株を変異処理してキサントフィル生産性を向上させるために選択したキサントフィル高生産株を用いることもできる。なお、E-396菌株は、独立行政法人製品評価技術基盤機構(NITE)、特許生物寄託センター(IPOD)に国際寄託されている(旧寄託先名称:通商産業省工業技術院生命工学工業技術研究所)。 In the present invention, bacteria in which the DNA base sequence corresponding to 16S ribosomal RNA is substantially homologous to the base sequence set forth in SEQ ID NO: 1 are preferably used, particularly in terms of the growth rate and xanthophyll productivity. "Substantially homologous" means that the sequence has, for example, 94% or more, 96% or more, or 98% or more homology, taking into consideration the error frequency in determining the DNA base sequence. As such bacteria, the E-396 strain (FERM BP-4283) is particularly preferred. In addition, a high xanthophyll-producing strain selected to improve xanthophyll productivity by mutating the E-396 strain can also be used. The E-396 strain is internationally deposited at the International Patent Organism Depositary (IPOD) of the National Institute of Technology and Evaluation (NITE) (former depository name: National Institute of Bioscience and Human-Technology, Agency of Industrial Science and Technology, Ministry of International Trade and Industry).
キサントフィルを上記工程によって抽出した後、濃縮、晶析、クロマトグラフィー、ろ過、乾燥等によってキサントフィルを回収することができる。 After xanthophyll is extracted by the above process, it can be recovered by concentration, crystallization, chromatography, filtration, drying, etc.
本発明において、異性化効率は少なくとも1.1倍~1.6倍に向上させることができる。例えば1.1倍以上、1.2倍以上、1.3倍以上、1.4倍以上、1.5倍以上、あるいは1.6倍以上向上させることができる。異性化効率は、異性化触媒を加えた系にて得られたシス型カロテノイド量を、異性化触媒を加えない系にて得られたシス型カロテノイド量にて除することで算出される。 In the present invention, the isomerization efficiency can be improved by at least 1.1 to 1.6 times. For example, it can be improved by 1.1 times or more, 1.2 times or more, 1.3 times or more, 1.4 times or more, 1.5 times or more, or 1.6 times or more. The isomerization efficiency is calculated by dividing the amount of cis-carotenoids obtained in a system with an isomerization catalyst added by the amount of cis-carotenoids obtained in a system without an isomerization catalyst added.
本発明において、抽出率は少なくとも1.1倍~1.6倍に向上させることができる。例えば1.1倍以上、1.2倍以上、1.3倍以上、1.4倍以上、1.5倍以上、あるいは2倍以上向上させることができる。抽出率は、抽出試験に用いた乾燥菌体に含まれるキサントフィルのうち、溶媒抽出によって抽出されたキサントフィルの割合を示す。 In the present invention, the extraction rate can be improved by at least 1.1 to 1.6 times. For example, it can be improved by 1.1 times or more, 1.2 times or more, 1.3 times or more, 1.4 times or more, 1.5 times or more, or 2 times or more. The extraction rate indicates the proportion of xanthophyll extracted by solvent extraction out of the xanthophyll contained in the dried cells used in the extraction test.
以下、実施例により本発明をさらに具体的に説明する。但し、本発明の範囲はこれらの実施例により限定されるものではない。 The present invention will be explained in more detail below with reference to examples. However, the scope of the present invention is not limited to these examples.
[実施例1]
特開2012-158569号公報に記載の方法に準じて、パラコッカス属E-396株を培養し、乾燥することで乾燥菌体(乾燥菌体中にアスタキサンチン3%、アドニルビン0.5%、アドニキサンチン0.5%、総カロテノイド4%含有)を得た。得られた乾燥菌体1gに、抽出溶媒としてエタノール(シグマアルドリッチ社製)30mL、異性化触媒としてメチルイソチオシアネート(東京化成工業社製)を100mM加え、60℃条件下、バイオシェーカー(タイテック社製、型番BR―180LF)にて200rpmで一時間攪拌し、トランス型キサントフィルの異性化およびキサントフィルの抽出を行った。得られた分散液をPTFEフィルター(大阪化学薬品社製、目開き0.22μm)でろ過することで、乾燥菌体が除去された抽出液を得た。得られた抽出液をHPLCを用いて下記分析条件にて分析し、異性化効率および抽出率を確認した。
[Example 1]
According to the method described in JP 2012-158569 A, Paracoccus sp. E-396 strain was cultured and dried to obtain dried cells (containing 3% astaxanthin, 0.5% adonirubin, 0.5% adonixanthin, and 4% total carotenoids in the dried cells). 30 mL of ethanol (Sigma-Aldrich) as an extraction solvent and 100 mM of methyl isothiocyanate (Tokyo Chemical Industry Co., Ltd.) as an isomerization catalyst were added to 1 g of the obtained dried cells, and the mixture was stirred at 200 rpm for 1 hour under 60 ° C. conditions using a bioshaker (Taitec Co., Ltd., model number BR-180LF) to perform isomerization of trans-xanthophyll and extraction of xanthophyll. The obtained dispersion was filtered with a PTFE filter (Osaka Chemical Industry Co., Ltd., mesh size 0.22 μm) to obtain an extract from which the dried cells were removed. The obtained extract was analyzed by HPLC under the following analytical conditions to confirm the isomerization efficiency and extraction rate.
結果を表1に示す。異性化効率は、異性化触媒を加えた系にて得られたシス型カロテノイド量を、異性化触媒を加えない系にて得られたシス型カロテノイド量にて除することで算出した。抽出率は、抽出試験に用いた乾燥菌体に含まれるキサントフィルの内、溶媒抽出によって抽出されたキサントフィルの割合を示す。 The results are shown in Table 1. The isomerization efficiency was calculated by dividing the amount of cis-carotenoids obtained in the system with the isomerization catalyst added by the amount of cis-carotenoids obtained in the system without the isomerization catalyst added. The extraction rate indicates the proportion of xanthophylls extracted by solvent extraction out of the xanthophylls contained in the dried cells used in the extraction test.
<HPLCによるキサントフィルの分析条件>
装置名:島津製作所社製、型番LC-20AD、SPD-M20A
使用カラム:Luna, 5μm, Silica(2), 150 mm x 4.6 mm 2本連結
移動相:n-ヘキサン(関東化学社製)/酢酸エチル(関東化学社製)/アセトン(関東化学社製)(70:20:10, v/v/v)
カラム温度:40℃
流速:1.2 mL/min
検出波長:470 nm
<Conditions for HPLC analysis of xanthophyll>
Device name: Shimadzu Corporation, model numbers LC-20AD and SPD-M20A
Column used: Luna, 5 μm, Silica (2), 150 mm x 4.6 mm, 2 columns connected Mobile phase: n-hexane (Kanto Chemical) / ethyl acetate (Kanto Chemical) / acetone (Kanto Chemical) (70:20:10, v/v/v)
Column temperature: 40°C
Flow rate: 1.2 mL / min
Detection wavelength: 470 nm
[実施例2]
異性化触媒としてエチルイソチオシアネート(東京化成工業社製)を100mM加えたこと以外は実施例1と同様に異性化および抽出を行い、異性化効率、および抽出率を確認した。結果を表1に示す。
[Example 2]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 100 mM of ethyl isothiocyanate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added as an isomerization catalyst, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例3]
異性化触媒としてアリルイソチオシアネート(東京化成工業社製)を100mM加えたこと以外は実施例1と同様に異性化および抽出を行い、異性化効率、および抽出率を確認した。結果を表1に示す。
[Example 3]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 100 mM of allyl isothiocyanate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added as an isomerization catalyst, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例4]
異性化触媒としてベンジルイソチオシアネート(富士フイルム和光純薬社製)を100mM加えたこと以外は実施例1と同様に異性化および抽出を行い、異性化効率、および抽出率を確認した。結果を表1に示す。
[Example 4]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 100 mM of benzyl isothiocyanate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added as an isomerization catalyst, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例5]
異性化触媒としてジアリルジスルフィド(東京化成工業社製)を100mM加えたこと以外は実施例1と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 5]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 100 mM of diallyl disulfide (manufactured by Tokyo Chemical Industry Co., Ltd.) was added as an isomerization catalyst, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例6]
異性化触媒としてジメチルトリスルフィド(東京化成工業社製)を100mM加えたこと以外は実施例1と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 6]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 100 mM of dimethyl trisulfide (manufactured by Tokyo Chemical Industry Co., Ltd.) was added as an isomerization catalyst, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例7]
抽出温度を50℃としたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 7]
Isomerization and extraction were carried out in the same manner as in Example 3, except that the extraction temperature was set to 50° C., and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例8]
抽出温度を70℃としたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 8]
Isomerization and extraction were carried out in the same manner as in Example 3, except that the extraction temperature was set to 70° C., and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例9]
アリルイソチオシアネートを25mM加えたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 9]
Isomerization and extraction were carried out in the same manner as in Example 3, except that 25 mM allyl isothiocyanate was added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例10]
アリルイソチオシアネートを50mM加えたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 10]
Isomerization and extraction were carried out in the same manner as in Example 3, except that 50 mM allyl isothiocyanate was added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例11]
アリルイソチオシアネートを200mM加えたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 11]
Isomerization and extraction were carried out in the same manner as in Example 3, except that 200 mM allyl isothiocyanate was added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例12]
アリルイソチオシアネートを400mM加えたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。また、実施例12における乾燥菌体原料及び抽出液のシス型キサントフィル比率を図1に示す。
[Example 12]
Isomerization and extraction were performed in the same manner as in Example 3, except that 400 mM allyl isothiocyanate was added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1. The cis-xanthophyll ratios of the dried cell raw material and the extract in Example 12 are shown in Figure 1.
[実施例13]
抽出溶媒としてエタノールの代わりにn-ヘキサン(関東化学社製)を用いたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 13]
Isomerization and extraction were carried out in the same manner as in Example 3, except that n-hexane (manufactured by Kanto Chemical Co., Ltd.) was used as the extraction solvent instead of ethanol, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例14]
抽出溶媒としてエタノールの代わりにアセトン(シグマアルドリッチ社製)を用いたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 14]
Isomerization and extraction were carried out in the same manner as in Example 3, except that acetone (Sigma-Aldrich) was used instead of ethanol as the extraction solvent, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例15]
抽出溶媒としてエタノールの代わりに酢酸エチル(関東化学社製)を用いたこと以外は実施例3と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 15]
Isomerization and extraction were carried out in the same manner as in Example 3, except that ethyl acetate (manufactured by Kanto Chemical Co., Ltd.) was used as the extraction solvent instead of ethanol, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例16]
異性化触媒としてメチルイソチオシアネートの代わりに塩化鉄(III)(関東化学社製)を10mM添加したこと以外は実施例1と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 16]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 10 mM of iron(III) chloride (Kanto Chemical Co., Ltd.) was added as the isomerization catalyst instead of methyl isothiocyanate, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例17]
異性化触媒としてメチルイソチオシアネートの代わりに塩化銅(II)(関東化学社製)を10mM添加したこと以外は実施例1と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 17]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 10 mM of copper(II) chloride (Kanto Chemical Co., Ltd.) was added as the isomerization catalyst instead of methyl isothiocyanate, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[実施例18]
異性化触媒としてメチルイソチオシアネートの代わりにヨウ素(東京化成工業社製)を10mM添加したこと以外は実施例1と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Example 18]
Isomerization and extraction were carried out in the same manner as in Example 1, except that 10 mM of iodine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added as an isomerization catalyst instead of methyl isothiocyanate, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[比較例1]
異性化触媒を加えないこと以外は実施例1と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Comparative Example 1]
The isomerization and extraction were carried out in the same manner as in Example 1, except that no isomerization catalyst was added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[比較例2]
異性化触媒を加えないこと以外は実施例7と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Comparative Example 2]
The isomerization and extraction were carried out in the same manner as in Example 7, except that the isomerization catalyst was not added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[比較例3]
異性化触媒を加えないこと以外は実施例8と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Comparative Example 3]
The isomerization and extraction were carried out in the same manner as in Example 8, except that the isomerization catalyst was not added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[比較例4]
異性化触媒を加えないこと以外は実施例13と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Comparative Example 4]
The isomerization and extraction were carried out in the same manner as in Example 13, except that the isomerization catalyst was not added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
[比較例5]
異性化触媒を加えないこと以外は実施例14と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Comparative Example 5]
The isomerization efficiency and extraction rate were confirmed by carrying out isomerization and extraction in the same manner as in Example 14, except that the isomerization catalyst was not added. The results are shown in Table 1.
[比較例6]
異性化触媒を加えないこと以外は実施例15と同様に異性化および抽出を行い、異性化効率および抽出率を確認した。結果を表1に示す。
[Comparative Example 6]
The isomerization and extraction were carried out in the same manner as in Example 15, except that the isomerization catalyst was not added, and the isomerization efficiency and extraction rate were confirmed. The results are shown in Table 1.
実施例1において、異性化触媒としてメチルイソチオシアネートを用いたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて2.1倍向上し、アドニルビンについて1.3倍向上し、アドニキサンチンについて2.3倍向上した。また、抽出率は、アスタキサンチンについて1.3倍向上し、アドニルビンについて1.2倍向上した。 In Example 1, when methyl isothiocyanate was used as the isomerization catalyst, the isomerization efficiency was improved by 2.1 times for astaxanthin, 1.3 times for adonirubin, and 2.3 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.3 times for astaxanthin and 1.2 times for adonirubin.
実施例2において、異性化触媒としてエチルイソチオシアネートを用いたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて1.7倍向上し、アドニルビンについて1.1倍向上し、アドニキサンチンについて1.8倍向上した。また、抽出率は、アスタキサンチンについて1.3倍向上し、アドニルビンについて1.2倍向上した。 In Example 2, when ethyl isothiocyanate was used as the isomerization catalyst, the isomerization efficiency was improved by 1.7 times for astaxanthin, 1.1 times for adonirubin, and 1.8 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.3 times for astaxanthin and 1.2 times for adonirubin.
実施例3において、異性化触媒としてアリルイソチオシアネートを用いたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて2.3倍向上し、アドニルビンについて1.4倍向上し、アドニキサンチンについて2.4倍向上した。また、抽出率は、アスタキサンチンについて1.3倍向上し、アドニルビンについて1.2倍向上した。 In Example 3, when allyl isothiocyanate was used as the isomerization catalyst, the isomerization efficiency was improved by 2.3 times for astaxanthin, 1.4 times for adonirubin, and 2.4 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.3 times for astaxanthin and 1.2 times for adonirubin.
実施例4において、異性化触媒としてベンジルイソチオシアネートを用いたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて2.3倍向上し、アドニルビンについて1.4倍向上し、アドニキサンチンについて2.4倍向上した。また、抽出率は、アスタキサンチンについて1.4倍向上し、アドニルビンについて1.3倍向上した。 In Example 4, when benzyl isothiocyanate was used as the isomerization catalyst, the isomerization efficiency was improved by 2.3 times for astaxanthin, 1.4 times for adonirubin, and 2.4 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.4 times for astaxanthin and 1.3 times for adonirubin.
実施例5において、異性化触媒としてジアリルジスルフィドを用いたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて2.0倍向上し、アドニルビンについて1.3倍向上し、アドニキサンチンについて2.0倍向上した。また、抽出率は、アスタキサンチンについて1.2倍向上し、アドニルビンについて1.1倍向上した。 In Example 5, when diallyl disulfide was used as the isomerization catalyst, the isomerization efficiency was improved by 2.0 times for astaxanthin, 1.3 times for adonirubin, and 2.0 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.2 times for astaxanthin and 1.1 times for adonirubin.
実施例6において、異性化触媒としてジメチルトリスルフィドを用いたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて1.9倍向上し、アドニルビンについて1.2倍向上し、アドニキサンチンについて2.1倍向上した。また、抽出率は、アスタキサンチンについて1.3倍向上し、アドニルビンについて1.2倍向上した。 In Example 6, when dimethyl trisulfide was used as the isomerization catalyst, the isomerization efficiency was improved by 1.9 times for astaxanthin, 1.2 times for adonirubin, and 2.1 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.3 times for astaxanthin and 1.2 times for adonirubin.
実施例7において、抽出温度を50℃としたときの異性化効率は、異性化触媒を用いなかった比較例2と比べて、アスタキサンチンについて2.2倍向上し、アドニルビンについて1.3倍向上し、アドニキサンチンについて2.5倍向上した。また、抽出率は、アスタキサンチン、アドニルビンともに1.2倍向上した。 In Example 7, the isomerization efficiency at an extraction temperature of 50°C was improved by 2.2 times for astaxanthin, 1.3 times for adonirubin, and 2.5 times for adonirubin, compared to Comparative Example 2, in which no isomerization catalyst was used. In addition, the extraction rates of both astaxanthin and adonirubin were improved by 1.2 times.
実施例8において、抽出温度を70℃としたときの異性化効率は、異性化触媒を用いなかった比較例3と比べて、アスタキサンチンについて1.5倍向上し、アドニルビンについて1.2倍向上し、アドニキサンチンについて1.8倍向上した。また、抽出率は、アスタキサンチン、アドニルビンともに1.2倍向上した。 In Example 8, the isomerization efficiency at an extraction temperature of 70°C was improved by 1.5 times for astaxanthin, 1.2 times for adonirubin, and 1.8 times for adonirubin, compared to Comparative Example 3, in which no isomerization catalyst was used. In addition, the extraction rates of both astaxanthin and adonirubin were improved by 1.2 times.
実施例9において、異性化触媒量を25mMとしたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて1.4倍向上し、アドニルビンについて1.1倍向上し、アドニキサンチンについて1.6倍向上した。 In Example 9, when the amount of the isomerization catalyst was 25 mM, the isomerization efficiency was improved by 1.4 times for astaxanthin, 1.1 times for adonirubin, and 1.6 times for adonixanthin, compared to Comparative Example 1, in which no isomerization catalyst was used.
実施例10において、異性化触媒量を50mMとしたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて1.8倍向上し、アドニルビンについて1.3倍向上し、アドニキサンチンについて2.0倍向上した。 In Example 10, when the amount of the isomerization catalyst was 50 mM, the isomerization efficiency was improved by 1.8 times for astaxanthin, 1.3 times for adonirubin, and 2.0 times for adonixanthin, compared to Comparative Example 1, in which no isomerization catalyst was used.
実施例11において、異性化触媒量を200mMとしたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて2.6倍向上し、アドニルビンについて1.5倍向上し、アドニキサンチンについて2.8倍向上した。また、抽出率は、アスタキサンチンについて1.4倍向上し、アドニルビンについて1.4倍向上した。 In Example 11, when the amount of the isomerization catalyst was 200 mM, the isomerization efficiency was improved by 2.6 times for astaxanthin, 1.5 times for adonirubin, and 2.8 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.4 times for astaxanthin and 1.4 times for adonirubin.
実施例12において、異性化触媒量を400mMとしたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて2.7倍向上し、アドニルビンについて1.5倍向上し、アドニキサンチンについて2.8倍向上した。また、抽出率は、アスタキサンチン、アドニルビンともに1.7倍向上した。 In Example 12, when the amount of isomerization catalyst was 400 mM, the isomerization efficiency was improved by 2.7 times for astaxanthin, 1.5 times for adonirubin, and 2.8 times for adonirubin, compared to Comparative Example 1, in which no isomerization catalyst was used. In addition, the extraction rate was improved by 1.7 times for both astaxanthin and adonirubin.
実施例13において、抽出溶媒をn-ヘキサンとしたときの異性化効率は、異性化触媒を用いなかった比較例4と比べて、アスタキサンチンについて1.7倍向上し、アドニルビンについて1.1倍向上し、アドニキサンチンについて1.5倍向上した。また、抽出率は、アスタキサンチン、アドニルビンともに1.3倍向上した。 In Example 13, when n-hexane was used as the extraction solvent, the isomerization efficiency was improved by 1.7 times for astaxanthin, 1.1 times for adonirubin, and 1.5 times for adonirubin, compared to Comparative Example 4, in which no isomerization catalyst was used. In addition, the extraction rates were improved by 1.3 times for both astaxanthin and adonirubin.
実施例14において、抽出溶媒をアセトンとしたときの異性化効率は、異性化触媒を用いなかった比較例5と比べて、アスタキサンチンについて1.4倍向上し、アドニルビンについて1.1倍向上し、アドニキサンチンについて1.6倍向上した。また、抽出率は、アスタキサンチン、アドニルビンともに1.2倍向上した。 In Example 14, when acetone was used as the extraction solvent, the isomerization efficiency was improved by 1.4 times for astaxanthin, 1.1 times for adonirubin, and 1.6 times for adonirubin, compared to Comparative Example 5, in which no isomerization catalyst was used. In addition, the extraction rates were improved by 1.2 times for both astaxanthin and adonirubin.
実施例15において、抽出溶媒を酢酸エチルとしたときの異性化効率は、異性化触媒を用いなかった比較例5と比べて、アスタキサンチンについて1.6倍向上し、アドニルビンについて1.4倍向上し、アドニキサンチンについて1.5倍向上した。 In Example 15, when ethyl acetate was used as the extraction solvent, the isomerization efficiency was improved by 1.6 times for astaxanthin, 1.4 times for adonirubin, and 1.5 times for adonixanthin, compared to Comparative Example 5, in which no isomerization catalyst was used.
実施例16において、異性化触媒を塩化鉄(III)としたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて1.4倍向上し、アドニルビンについて1.9倍向上し、アドニキサンチンについて2.3倍向上した。 In Example 16, when the isomerization catalyst was iron (III) chloride, the isomerization efficiency was improved by 1.4 times for astaxanthin, 1.9 times for adonirubin, and 2.3 times for adonixanthin, compared to Comparative Example 1, in which no isomerization catalyst was used.
実施例17において、異性化触媒を塩化銅(II)としたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて2.5倍向上し、アドニルビンについて1.4倍向上し、アドニキサンチンについて2.9倍向上した。 In Example 17, when the isomerization catalyst was copper (II) chloride, the isomerization efficiency was improved by 2.5 times for astaxanthin, 1.4 times for adonirubin, and 2.9 times for adonixanthin, compared to Comparative Example 1, in which no isomerization catalyst was used.
実施例18において、異性化触媒をヨウ素としたときの異性化効率は、異性化触媒を用いなかった比較例1と比べて、アスタキサンチンについて3.0倍向上し、アドニルビンについて1.5倍向上し、アドニキサンチンについて2.8倍向上した。 In Example 18, when iodine was used as the isomerization catalyst, the isomerization efficiency was improved by 3.0 times for astaxanthin, 1.5 times for adonirubin, and 2.8 times for adonixanthin, compared to Comparative Example 1, in which no isomerization catalyst was used.
[実施例19]
パラコッカス菌の培養液を遠心濃縮後、区分に応じて以下の処理を行った。処理条件の詳細を表2に示す。
[Example 19]
The culture solution of Paracoccus was concentrated by centrifugation and then subjected to the following treatments according to the classification. The details of the treatment conditions are shown in Table 2.
アリルイソチオシアネートおよびオイル(大豆油)を添加せず、加熱もしなかったときのアスタキサンチンシス体比率は3.9%であった。
区分1~4は、アリルイソチオシアネートを添加せず、オイル(大豆油)を添加して100℃に加熱したときの処理区分である。
区分5~12は、オイル(大豆油)、及び100または300mMのアリルイソチオシアネートの両者を添加し、100℃に加熱したときの処理区分である。
区分13~20は、オイル(大豆油)を添加せず、3~10% のアリルイソチオシアネートを添加して100℃に加熱したときの処理区分である。
When allyl isothiocyanate and oil (soybean oil) were not added and heating was not performed, the astaxanthin cis-isomer ratio was 3.9%.
Sections 1 to 4 are treatment sections in which allyl isothiocyanate was not added, oil (soybean oil) was added, and the mixture was heated to 100°C.
Sections 5 to 12 are treatment sections in which both oil (soybean oil) and 100 or 300 mM allyl isothiocyanate were added and the mixture was heated to 100°C.
Sections 13 to 20 are treatment sections in which no oil (soybean oil) was added, but 3 to 10% allyl isothiocyanate was added and the mixture was heated to 100°C.
結果を表3及び図2に示す。
オイル(大豆油)及び100または300mMのアリルイソチオシアネートを添加した区分(区分5~12)では、アスタキサンチンのシス化率は15%程度向上し、オイルを添加せず3~10%のアリルイソチオシアネートを添加した区分(区分13~20)では、アスタキサンチンシス化率は最大約40%まで向上した。
オイル(大豆油)のみを添加した区分(区分1~4)はほとんど異性化しなかった。
The results are shown in Table 3 and FIG.
In the sections (sections 5 to 12) to which oil (soybean oil) and 100 or 300 mM allyl isothiocyanate were added, the cis-conversion rate of astaxanthin increased by approximately 15%, while in the sections (sections 13 to 20) to which no oil was added but 3 to 10% allyl isothiocyanate was added, the cis-conversion rate of astaxanthin increased by a maximum of approximately 40%.
The fractions (fractions 1 to 4) to which only oil (soybean oil) was added showed almost no isomerization.
表3において、「All-E」はトランス体を表す。「Total Z」はシス体全体を表す。9Z、13Z、15Zは、それぞれ、9位、13位、15位の位置がシス構造のシス体を表す。「Other Z」は9Z、13Z、15Z以外のシス体を表す。 In Table 3, "All-E" represents the trans form. "Total Z" represents the entire cis form. 9Z, 13Z, and 15Z represent cis forms with cis structures at positions 9, 13, and 15, respectively. "Other Z" represents cis forms other than 9Z, 13Z, and 15Z.
配列番号1:nはa,c,gまたはtを表す(存在位置:1350)。 Sequence number 1: n represents a, c, g or t (position: 1350).
Claims (9)
9. The isomerization catalyst according to claim 8 , wherein the isothiocyanate or polysulfide is at least one selected from the group consisting of methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, benzyl isothiocyanate, diallyl disulfide, and dimethyl trisulfide.
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