JP5137220B1 - Method for producing solder anthocyanin pigment extract - Google Patents
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Abstract
【課題】 アントシアニン系色素抽出物を製造するのに、クロロフィルを除去でき、且つ、水溶性粘性多糖類を抽出せずにアントシアニン系色素抽出物を効率良く取得でき、アントシアニン系色素とＧＡＢＡを分別してアントシアニン系色素抽出物を得る製造方法を提供する。
【解決手段】 ハンダマ生葉を乾燥し、乾燥物をそのまま又は粉砕し、５０〜８０％エタノール水溶液を供し、クロロフィルを含有する抽出残渣と、ＧＡＢＡとアントシアニン系色素を含有するエタノール水溶液とに分別し、得られたＧＡＢＡとアントシアニン系色素を含有するエタノール水溶液に対してエタノールを回収除去することによりクロロフィルを沈殿させて除去し、ＧＡＢＡとアントシアニン系色素が濃縮された濃縮液を取得し、濃縮液を、疎水成分の吸着機能を持つ吸着材カラムに供することによりアントシアニン系色素を吸着させ、素通りするＧＡＢＡ含有水溶液を除去し、次いで、前記吸着カラムに吸着されたアントシアニン系色素をエタノール水溶液で溶出することによりアントシアニン系色素を含有する吸着画分を取得する。
【選択図】なしPROBLEM TO BE SOLVED: To produce an anthocyanin pigment extract, which can remove chlorophyll and efficiently obtain an anthocyanin pigment extract without extracting a water-soluble viscous polysaccharide. Provided is a production method for obtaining an anthocyanin pigment extract.
SOLUTION: A fresh solder leaf is dried, the dried product is directly or pulverized, provided with a 50 to 80% aqueous ethanol solution, and separated into an extraction residue containing chlorophyll and an aqueous ethanol solution containing GABA and anthocyanin pigments, Chlorophyll is precipitated and removed by recovering and removing ethanol from the ethanol aqueous solution containing the obtained GABA and anthocyanin dyes to obtain a concentrated liquid in which GABA and anthocyanin dyes are concentrated. By adsorbing an anthocyanin dye by applying it to an adsorbent column having an adsorption function of a hydrophobic component, removing a GABA-containing aqueous solution that passes through, and then eluting the anthocyanin dye adsorbed on the adsorption column with an aqueous ethanol solution Acquired adsorption fractions containing anthocyanin dyes To do.
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Description
本発明は、ハンダマ葉からアントシアニン系色素抽出物を製造する方法に関する。 The present invention relates to a method for producing an anthocyanin pigment extract from handama leaves.
ハンダマは、別名、金時草、或いはスイゼンジナとも呼ばれており、奄美大島では長寿食として多く食べられている。ハンダマは、高血圧抑制、抗酸化能、抗ガン能など健康維持機能を持つことが知られている。またハンダマには、アントシアニン系色素、クロロフィル、ＧＡＢＡ、粘性多糖類が含まれていることが知られている〔特開２００６−１１７５８４号公報（特許文献１）、特開２００７−２８９０５７号公報（特許文献２）、特許第４１１３９１８号公報（特許文献３）〕。 Solderama is also known as Kinkiso or Suizinina, and is often eaten as a long-lived meal in Amami Oshima. Solderama is known to have health maintenance functions such as hypertension suppression, antioxidant ability, and anticancer ability. In addition, it is known that solders contain anthocyanin pigments, chlorophyll, GABA, and viscous polysaccharides [Japanese Patent Laid-Open No. 2006-117484 (Patent Document 1), Japanese Patent Laid-Open No. 2007-289057 (Patent Patents). Document 2), Japanese Patent No. 4113918 (Patent Document 3)].
ハンダマは夏場において生じるアントシアニン系色素含量が著しく低下し、また寒さにも弱いため冬場は枯れて収穫できない。そこでハンダマ原料からアントシアニン系色素を効率的に抽出して、年間を通じてハンダマのアントシアニン系色素抽出物を製造する方法が望まれている。 Solderama can not be harvested withering in the winter because the anthocyanin pigment content that occurs in the summer is remarkably reduced and it is vulnerable to cold. Therefore, there is a demand for a method for efficiently extracting anthocyanin-based pigments from solder material and producing solder anthocyanin-based pigment extracts throughout the year.
従来、ハンダマ葉を熱水で加熱してアントシアニン系色素を熱水抽出する方法、あるいは加熱処理して凍結乾燥で保存後に熱水抽出する方法が知られているが、ハンダマ葉を熱水抽出するとハンダマ葉中の粘性多糖類が共に溶けだし、アントシアニン系色素の分別時の障害となっていた。 Conventionally, a method for extracting anthocyanin pigments with hot water by heating the solder leaves with hot water, or a method for extracting hot water after heat treatment and storage by freeze-drying is known. The viscous polysaccharides in the solder leaves began to dissolve together, which was an obstacle during the fractionation of anthocyanin pigments.
特許第４１１３９１８号公報（特許文献３）には、ハンダマの葉を蒸気加熱温度が８５〜１１０℃、蒸気加熱時間が３〜８分の条件で蒸気加熱した後、熱風乾燥して得た乾燥ハンダマを熱水で抽出し、或いはその抽出液を粉末化して、アントシアニン系色素を含有する色素抽出液又は粉末を製造する方法が示されている。 Japanese Patent No. 4113918 (Patent Document 3) discloses a dry solder obtained by steam heating a leaf of solder with a steam heating temperature of 85 to 110 ° C. and a steam heating time of 3 to 8 minutes and then drying with hot air. Is extracted with hot water, or the extract is pulverized to produce a dye extract or powder containing an anthocyanin dye.
特開２００８−１７４４５９号公報（特許文献４）には、ハンダマを乾燥後、水及び親水性有機溶媒で抽出して得られた抽出液をそのまま、或いは濃縮して濃縮液又は乾燥物を得、或いは、抽出液から抽出溶媒を留去して乾燥して乾燥物を得ることが示されている。 In JP2008-17459A (Patent Document 4), after drying the solder, the extract obtained by extraction with water and a hydrophilic organic solvent is directly or concentrated to obtain a concentrated solution or a dried product, Alternatively, it is shown that the extraction solvent is distilled off from the extract and dried to obtain a dried product.
前記特許文献３のアントシアニン系色素を含有する色素抽出液は、蒸気加熱した後、熱風乾燥して得た乾燥ハンダマを熱水で抽出してアントシアニン系色素を抽出しているが、該方法では乾燥ハンダマを熱水で抽出しているため水溶性粘性多糖類も同時に抽出されてしまい、抽出液と固形分を分別するのにろ過或いは遠心分離が極めて困難になるという問題がある。 The dye extract containing the anthocyanin dye of Patent Document 3 is heated with steam and then dried with hot air to extract the anthocyanin dye by hot water extraction. Since the solder is extracted with hot water, the water-soluble viscous polysaccharide is also extracted at the same time, and there is a problem that filtration or centrifugation becomes extremely difficult to separate the extract from the solid content.
前記特許文献３によれば、ハンダマをそのまま凍結乾燥により粉末化すると、得られる粉末は緑色を呈しており、目的とするアントシアニン系色素の赤紫色粉末は得られないとしている（特許文献３の段落〔０００９〕）。 According to Patent Document 3, when solder is pulverized as it is by lyophilization, the resulting powder exhibits a green color, and the target anthocyanin pigment reddish purple powder cannot be obtained (paragraph of Patent Document 3). [0009]).
前記特許文献４の抽出物は、アントシアニン系色素とＧＡＢＡを分別していない。 The extract of Patent Document 4 does not separate anthocyanin pigments from GABA.
そこで本願発明は、アントシアニン系色素抽出物を製造するのに、クロロフィルを除去することができ、且つ、水溶性粘性多糖類を抽出せずにアントシアニン系色素抽出物を効率良く取得でき、アントシアニン系色素とＧＡＢＡを分別してアントシアニン系色素抽出物を得る製造方法を提供することを課題とする。 Therefore, the present invention provides an anthocyanin dye that can remove chlorophyll and efficiently obtain an anthocyanin dye extract without extracting a water-soluble viscous polysaccharide to produce an anthocyanin dye extract. It is an object of the present invention to provide a production method for obtaining an anthocyanin pigment extract by separating GABA and GABA.
前記課題を解決するための本発明のアントシアニン系色素抽出物の製造方法は、（１）ハンダマ生葉を乾燥し、（２）前記工程で得られた乾燥物をそのまま又は粉砕し、５０〜８０％エタノール水溶液を供し、クロロフィルを含有する抽出残渣と、ＧＡＢＡとアントシアニン系色素を含有するエタノール水溶液とに分別し、（３）前記工程で得られたＧＡＢＡとアントシアニン系色素を含有するエタノール水溶液に対してエタノールを回収除去することによりクロロフィルを沈殿させて除去し、ＧＡＢＡとアントシアニン系色素が濃縮された濃縮液を取得し、（４）前記工程で得られた濃縮液を、疎水成分の吸着機能を持つ吸着材カラムに供することによりアントシアニン系色素を吸着させ、素通りするＧＡＢＡ含有水溶液を除去し、（５）次いで、前記吸着カラムに吸着されたアントシアニン系色素をエタノール水溶液で溶出することによりアントシアニン系色素を含有する吸着画分を取得することを特徴とする。 The method for producing an anthocyanin pigment extract of the present invention for solving the above-mentioned problems is as follows: (1) Drying the fresh solder leaves, (2) The dried product obtained in the above step as it is or pulverized, 50-80% An aqueous ethanol solution is provided and separated into an extraction residue containing chlorophyll and an aqueous ethanol solution containing GABA and anthocyanin dyes. (3) For the aqueous ethanol solution containing GABA and anthocyanin dyes obtained in the above step By collecting and removing ethanol, chlorophyll is precipitated and removed to obtain a concentrated solution in which GABA and anthocyanin pigments are concentrated. (4) The concentrated solution obtained in the above step has a hydrophobic component adsorption function. Adsorbing an anthocyanin dye by using an adsorbent column, and removing the GABA-containing aqueous solution that passes through (5) Ide, and acquires the adsorbed fraction containing the anthocyanin-based pigments by eluting the adsorption column in the adsorbed anthocyanin pigments in aqueous ethanol.
前記工程（１）で用いるハンダマ生葉の乾燥物は、ハンダマ生葉を凍結乾燥法、減圧温風乾燥法、或いは熱風乾燥法により乾燥して得ることができる。ハンダマ生葉を乾燥物とすることにより生葉に多量に含まれる水分が存在しないので、抽出に用いるエタノール水溶液のエタノール濃度が低下しない。そのためハンダマ葉に含まれる水溶性の粘性多糖類が抽出されず安定して抽出できる。 The dried dried raw solder leaves used in the step (1) can be obtained by drying fresh dried solder leaves by a freeze drying method, a reduced pressure hot air drying method, or a hot air drying method. By making the fresh solder leaves into a dry product, there is no water contained in large quantities in the fresh leaves, so the ethanol concentration of the aqueous ethanol solution used for extraction does not decrease. Therefore, the water-soluble viscous polysaccharide contained in the handama leaf can be stably extracted without being extracted.
前記工程（２）で用いるエタノール水溶液はｐＨが酸性側に調整されたものであることが望ましい。酸性側ではアントシアニン系色素を安定に抽出するために望ましく、また、酸性下ではアントシアニンの呈色がきれいに観察できる。 It is desirable that the ethanol aqueous solution used in the step (2) has a pH adjusted to the acidic side. On the acidic side, it is desirable for stably extracting the anthocyanin-based pigment, and under an acidic condition, the coloration of the anthocyanin can be clearly observed.
前記工程（２）で得られたＧＡＢＡとアントシアニン系色素を含有するエタノール水溶液に対して、前記工程（３）によりエタノールを回収除去することにより、クロロフィルを沈殿させることができるので、クロロフィルを除去したＧＡＢＡとアントシアニン系色素が濃縮された濃縮液を取得することができる。 Since the chlorophyll can be precipitated by recovering and removing ethanol in the step (3) with respect to the ethanol aqueous solution containing GABA and anthocyanin pigment obtained in the step (2), the chlorophyll was removed. A concentrated solution in which GABA and anthocyanin pigments are concentrated can be obtained.
前記工程（４）において、前記工程（３）で得られた濃縮液を、疎水成分の吸着機能を持つ吸着材カラムに供することによりアントシアニン系色素を該吸着材カラムに吸着させ、ＧＡＢＡを素通りする水溶液として除去することができる。 In the step (4), the concentrated solution obtained in the step (3) is subjected to an adsorbent column having a function of adsorbing hydrophobic components, thereby adsorbing the anthocyanin dye on the adsorbent column and passing through GABA. It can be removed as an aqueous solution.
前記工程（５）において、吸着カラムに吸着されたアントシアニン系色素をエタノール水溶液で溶出することによりアントシアニン系色素を含有する吸着画分を取得することができる。 In the step (5), an anthocyanin dye adsorbed on the adsorption column is eluted with an aqueous ethanol solution, whereby an adsorption fraction containing an anthocyanin dye can be obtained.
さらにアントシアニン系色素の抽出率を上げるには、前記工程（２）で得られた抽出残渣に対しエタノール水溶液を再度供して、該抽出残渣中に未だ残存しているＧＡＢＡとアントシアニン系色素をエタノール水溶液に移行させ、夾雑物であるクロロフィルを抽出残渣として分別し、該工程で得られたエタノール水溶液と前記工程（２）で得られたエタノール水溶液を混合し、次いで、前記工程（３）、４及び（５）を行うことが好ましい。該クロロフィルを抽出残差として分別することにより、得られたアントシアニン系色素は、クロロフィル由来の黒緑色乃至緑色成分が排除される。 In order to further increase the extraction rate of the anthocyanin pigment, an aqueous ethanol solution is again applied to the extraction residue obtained in the step (2), and the GABA and anthocyanin pigment still remaining in the extraction residue are removed from the aqueous ethanol solution. Chlorophyll, which is a contaminant, is separated as an extraction residue, and the ethanol aqueous solution obtained in the step and the ethanol aqueous solution obtained in the step (2) are mixed, and then the steps (3), 4 and It is preferable to perform (5). By separating the chlorophyll as an extraction residual, the obtained anthocyanin pigments exclude black-green to green components derived from chlorophyll.
前記工程（５）におけるアントシアニン系色素を溶出・回収するためのエタノール水溶液は５０〜８０％のエタノール水溶液を用いることが望ましい。該アントシアニン系色素を５０〜８０％のエタノール水溶液で溶出・回収することにより、ハンダマ葉に含まれる粘性多糖類も抽出されない。 The ethanol aqueous solution for eluting and recovering the anthocyanin dye in the step (5) is preferably a 50 to 80% ethanol aqueous solution. By elution and recovery of the anthocyanin pigment with 50-80% ethanol aqueous solution, the viscous polysaccharide contained in the solder leaves is not extracted.
本発明のアントシアニン系色素抽出物の製造方法により得られたアントシアニン系色素抽出物は、粘性多糖類、クロロフィル、ＧＡＢＡの分離除去処理がなされているため、アントシアニン系色素抽出物は色調が安定であり、飲料の色付、酒の色付、ケーキ・パンの色付、米炊飯時の着色などあらゆる食品の加熱操作のあるなしにかかわらずに着色に利用でき、また、医薬品、化粧料の着色に利用できる。 The anthocyanin pigment extract obtained by the method for producing an anthocyanin pigment extract of the present invention has been subjected to separation and removal of viscous polysaccharides, chlorophyll, and GABA. Therefore, the color tone of the anthocyanin pigment extract is stable. Can be used for coloring foods with or without heating, such as coloring of beverages, coloring of liquor, coloring of cakes and breads, coloring when cooking rice, and for coloring of pharmaceuticals and cosmetics Available.
本発明のアントシアニン系色素抽出物の製造方法によれば、ハンダマ生葉を乾燥して得た乾燥物に５０〜８０％のエタノールによりアントシアニン系色素を抽出しているので、アントシアニン系色素抽出操作時に、エタノール濃度を下げる原因となる葉の水分も影響せず、且つ、ハンダマ葉に含まれる粘性多糖類も抽出されず、アントシアニン系色素を含有するエタノール水溶液は粘度の低いサラサラの状態となる。従って、アントシアニン系色素を含有するエタノール水溶液は、固形分と分別が容易に行える。例えば、ロ紙を用いてブフナーロートなどで簡便に吸引ろ過、或いは遠心分離して固形分を分別してアントシアニン系色素を含有するエタノール水溶液を得ることができる。 According to the method for producing an anthocyanin pigment extract of the present invention, since an anthocyanin pigment is extracted with 50 to 80% ethanol in a dried product obtained by drying handama fresh leaves, during an anthocyanin pigment extraction operation, The leaf moisture that causes the ethanol concentration to decrease is not affected, and the viscous polysaccharides contained in the solder leaves are not extracted, and the ethanol aqueous solution containing the anthocyanin pigment is in a smooth state with low viscosity. Therefore, the ethanol aqueous solution containing the anthocyanin pigment can be easily separated from the solid content. For example, an aqueous ethanol solution containing an anthocyanin pigment can be obtained by using a Buchner funnel or the like using a paper and simply suction filtration or centrifuging to separate solids.
ハンダマ生葉を乾燥して得た乾燥物に５０〜８０％のエタノール水溶液によりアントシアニン系色素を抽出しており、アントシアニン系色素抽出操作時に生じる抽出残差に大部分のクロロフィルが移行するのでクロロフィルを除去できる。さらに、アントシアニン系色素抽出操作時に得られるアントシアニン系色素を含有するエタノール水溶液に対してエタノールを回収除去する時にエタノール水溶液に一部溶解していたクロロフィルが沈殿するので、該クロロフィルを含有する沈殿物を除去することができる。したがって、本発明のアントシアニン系色素抽出物はクロロフィルの分離除去処理がなされている。 Anthocyanin pigments are extracted with 50-80% ethanol aqueous solution to dry matter obtained by drying fresh solder leaves, and most of the chlorophyll is transferred to the extraction residue generated during anthocyanin pigment extraction operation, so chlorophyll is removed. it can. Furthermore, since the chlorophyll partially dissolved in the ethanol aqueous solution precipitates when the ethanol is recovered and removed from the ethanol aqueous solution containing the anthocyanin pigment obtained during the anthocyanin pigment extraction operation, the precipitate containing the chlorophyll is removed. Can be removed. Therefore, the anthocyanin pigment extract of the present invention has been subjected to chlorophyll separation and removal treatment.
また、ハンダマ生葉を乾燥して得た乾燥物に５０〜８０％のエタノール水溶液によりアントシアニン系色素を抽出しているので、該抽出時にハンダマ葉から水分が移行することなくエタノール水溶液の濃度が低下しないので、蒸留等によるエタノールの回収を簡便に行うことができる。 Moreover, since the anthocyanin pigment is extracted with 50-80% ethanol aqueous solution to the dried product obtained by drying the fresh solder leaves, the concentration of the aqueous ethanol solution does not decrease without transferring water from the solder leaves during the extraction. Therefore, ethanol can be easily recovered by distillation or the like.
本発明のアントシアニン系色素抽出物は、前記アントシアニン系色素を含有するエタノール水溶液を、疎水成分の吸着機能を持つ吸着材カラムに供することによりアントシアニン系色素を吸着させ、ＧＡＢＡを素通りさせて除去し、該吸着カラムにエタノール水溶液を供してアントシアニン系色素を溶出しているので、得られたアントシアニン系色素を含有する抽出液にはＧＡＢＡの分離除去処理がなされている。 The anthocyanin dye extract of the present invention adsorbs an anthocyanin dye by subjecting the ethanol aqueous solution containing the anthocyanin dye to an adsorbent column having a function of adsorbing hydrophobic components, and passes GABA to remove it. Since an aqueous solution of ethanol is applied to the adsorption column to elute the anthocyanin dye, the resulting extract containing the anthocyanin dye is subjected to GABA separation and removal treatment.
ハンダマ生葉を凍結乾燥法、減圧温風乾燥法、或いは熱風乾燥法により乾燥する。乾燥物は砕いて室温で保存できる。粉砕した乾燥ハンダマ葉に室温で５０〜８０％エタノール水溶液、好ましくは５５〜７５％エタノール水溶液、さらに好ましくは６０〜７０％エタノール水溶液を加えて攪拌し、ＧＡＢＡとアントシアニン系色素を抽出する。エタノール水溶液の濃度が５０％未満ではハンダマ葉に含まれる粘性多糖類が抽出されてきて、ろ過あるは遠心分離が困難となり抽出液を得るのに不都合があるので、５０％以上とすることが必要である。アルコール濃度が８０％を超える場合には費用が増すので経済的観点から好ましくない。 The fresh solder leaves are dried by freeze-drying, reduced-pressure hot-air drying, or hot-air drying. The dried product can be crushed and stored at room temperature. To the pulverized dry solder leaves, 50-80% ethanol aqueous solution, preferably 55-75% ethanol aqueous solution, more preferably 60-70% ethanol aqueous solution is added at room temperature and stirred to extract GABA and anthocyanin pigment. If the concentration of the aqueous ethanol solution is less than 50%, viscous polysaccharides contained in the solder leaves will be extracted, and filtration or centrifugation will be difficult, which is inconvenient for obtaining an extract. It is. If the alcohol concentration exceeds 80%, the cost increases, which is not preferable from an economic viewpoint.
抽出に用いるエタノール水溶液は、酸で酸性側に調整しておくことが望ましい。酸性側ではアントシアニン系色素を安定に抽出するために望ましく、酸性下ではアントシアニンの呈色がきれいに観察できる。 The aqueous ethanol solution used for extraction is preferably adjusted to the acidic side with an acid. On the acidic side, it is desirable for stably extracting the anthocyanin-based pigment, and under an acidic condition, the coloration of the anthocyanin can be clearly observed.
エタノール水溶液で抽出する抽出液と固形分はろ過あるいは遠心分離法で分離され、固形分を分離除去し、抽出液を集める。この時、凍結乾燥ハンダマ葉を原料とすることから、生葉に多量に含まれる水分が存在しないので、エタノール水溶液のエタノール濃度が低下しない。そのためハンダマ葉に含まれる水溶性の粘性多糖類が抽出されず安定して抽出できる利点がある。また、粘性多糖類が抽出されないため抽出液の粘度が上昇しないのでろ過あるいは遠心分離法で極めて簡便に抽出液を得ることができる。 The extract and solid content extracted with an aqueous ethanol solution are separated by filtration or centrifugal separation, and the solid content is separated and removed, and the extract is collected. At this time, since lyophilized solderama leaves are used as raw materials, there is no water contained in large amounts in the fresh leaves, so the ethanol concentration of the aqueous ethanol solution does not decrease. Therefore, there is an advantage that the water-soluble viscous polysaccharide contained in the solder leaf can be stably extracted without being extracted. Further, since the viscous polysaccharide is not extracted, the viscosity of the extract does not increase, and therefore the extract can be obtained very simply by filtration or centrifugation.
抽出残渣に再度、５０〜８０％エタノール水溶液、好ましくは５５〜７５％エタノール水溶液、さらに好ましくは６０〜７０％エタノール水溶液を加えて攪拌し、乾燥葉のアントシアニンン系色素及びＧＡＢＡを抽出・回収することにより回収率を高めることができる。従って、多量の凍結乾燥葉を用いて少ない溶媒量でアントシアニン系色素及びＧＡＢＡの効率的な抽出が可能となる。 Add 50-80% ethanol aqueous solution, preferably 55-75% ethanol aqueous solution, more preferably 60-70% ethanol aqueous solution to the extraction residue, and stir to extract and recover the anthocyanin pigment and GABA from the dried leaves. Thus, the recovery rate can be increased. Therefore, an anthocyanin pigment and GABA can be efficiently extracted with a small amount of solvent using a large amount of freeze-dried leaves.
次に、減圧下（例えば、ロータリーエバポレーターを使用して）でエタノールを回収除去する。このエタノール除去時にエタノール濃度の減少と共に共雑物であるクロロフィルが沈澱するため、これを分離除去する。次に、少量の水を加えて更に減圧濃縮を繰り返しエタノールを回収除去、例えば、留去すると同時に、共雑するクロロフィルを再度分離除去する。残った水溶液は、微酸性の赤色透明で、きれいなアントシアニン系色素及びＧＡＢＡを含有する水溶液が得られる。 Next, ethanol is recovered and removed under reduced pressure (for example, using a rotary evaporator). At the time of this ethanol removal, chlorophyll, a contaminant, precipitates with a decrease in the ethanol concentration, which is separated and removed. Next, a small amount of water is added and concentration under reduced pressure is repeated to recover and remove ethanol, for example, by distilling off, and at the same time, chlorophyll that is contaminated is separated and removed again. The remaining aqueous solution is slightly acidic, red and transparent, and an aqueous solution containing a clean anthocyanin dye and GABA is obtained.
前記特許文献３のハンダマ色素の抽出法では、凍結乾燥法ではうまくアントシアニン系色素を抽出することが不可と報告している。この原因はアントシアニン系色素がクロロフィルと共に抽出され、黒い溶液となることを指している。本発明では５０〜８０％エタノール水溶液でのアントシアニン系色素抽出操作時に生じる抽出残差に大部分のクロロフィルが移行するのでクロロフィルを除去でき、且つ、エタノールを回収除去することで、エタノール水溶液中に一部溶解していた共雑物であるクロロフィルを沈殿として除くことにより、前記特許文献３の問題点をクリアーしている。 It has been reported that the extraction method of the solder pigment described in Patent Document 3 cannot successfully extract the anthocyanin pigment by the freeze-drying method. This is because the anthocyanin pigment is extracted together with chlorophyll and becomes a black solution. In the present invention, most of the chlorophyll is transferred to the extraction residue generated during the extraction operation of the anthocyanin dye in 50-80% ethanol aqueous solution, so that chlorophyll can be removed and the ethanol is recovered and removed. By removing chlorophyll, which is a partially mixed substance, as a precipitate, the problem of Patent Document 3 is cleared.
次に、前記工程で得られたアントシアニン系色素及びＧＡＢＡを含有する水溶液を疎水成分の吸着機能を持つ吸着材を充填したカラムに供し、疎水成分であるアントシアニン系色素を吸着させ、素通り画分にはＧＡＢＡが溶出するので除去する。ついで、該カラムを充分量の水で洗浄することにより、さらにＧＡＢＡを溶出させて除去する。 Next, the aqueous solution containing the anthocyanin dye and GABA obtained in the above step is applied to a column packed with an adsorbent having a function of adsorbing hydrophobic components to adsorb the anthocyanin dye as a hydrophobic component to pass through the fraction. Is removed as GABA elutes. Subsequently, the column is washed with a sufficient amount of water to further elute and remove GABA.
次に、吸着しているアントシアニンを４０％〜８０％エタノール水溶液、さらに好ましくは４５％〜７０％のエタノール水溶液で溶離・回収し、この画分を再度減圧化でエタノールを除去・回収し、濃縮されたアントシアニン水溶液を得る。得られた濃縮アントシアニン溶液を凍結乾燥し、乾燥品を得る。前記疎水成分の吸着機能を持つ吸着材には、例えば、スチレン−ジビニルベンゼン系合成吸着材が挙げられ、例えば、三菱化学株式会社製のＤＩＡＩＯＮ ＨＰ２０（商品名）を用いることができる。 Next, the adsorbed anthocyanins are eluted and collected with 40% to 80% ethanol aqueous solution, more preferably 45% to 70% ethanol aqueous solution, and this fraction is again decompressed to remove and collect ethanol and concentrate. An anthocyanin aqueous solution is obtained. The obtained concentrated anthocyanin solution is freeze-dried to obtain a dried product. Examples of the adsorbent having the function of adsorbing the hydrophobic component include a styrene-divinylbenzene synthetic adsorbent, and for example, DIAION HP20 (trade name) manufactured by Mitsubishi Chemical Corporation can be used.
水洗後、吸着しているアントシアニン系色素をエタノール水溶液、好ましくは４０％〜８０％のエタノール水溶液、さらに好ましくは４５％〜７０％のエタノール水溶液で溶出・回収し、再度減圧下でエタノールを回収・除去し、アントシアン系色素含有水溶液を得る。これを凍結乾燥法で乾燥粉末化してアントシアニン系色素粉末を得る。 After washing with water, the adsorbed anthocyanin dye is eluted and recovered with an aqueous ethanol solution, preferably 40% to 80% ethanol aqueous solution, more preferably 45% to 70% ethanol aqueous solution, and ethanol is recovered again under reduced pressure. Removal of an anthocyanic dye-containing aqueous solution. This is pulverized by freeze-drying to obtain an anthocyanin pigment powder.
［実施例１］
アントシアニンの抽出
ハンダマ生草を水洗後、凍結乾燥させたものをミルにて粉砕させ、ハンダマ粉末とした。得られたハンダマ粉末２．５ｇを５％酢酸を含有する７０％エタノール水溶液に加え、よく攪拌後、４，５００ｒｐｍ、２０分間遠心分離することにより固形分を分離除去し、得られた溶液をハンダマ粗抽出物とした。
[Example 1]
Anthocyanin extraction Soldered raw grass was washed with water and lyophilized, and pulverized with a mill to obtain solder powder. 2.5 g of the obtained solder powder was added to a 70% ethanol aqueous solution containing 5% acetic acid, and after stirring well, the solid content was separated and removed by centrifuging at 4,500 rpm for 20 minutes. A crude extract was obtained.
得られたハンダマ粗抽出物をエバポレーターにて減圧濃縮することにより酢酸およびエタノールを除去して５倍濃縮抽出物を得た。これを三菱化学株式会社製のＤＩＡＩＯＮ ＨＰ２０（商品名、スチレン−ジビニルベンゼン系クロマト分離材）を充填したカラム（直径４０ｍｍ、長さ３００ｍｍ）にアプライし、蒸留水にて溶出して素通り画分を得た。さらに５０％エタノール水溶液に溶媒を切り替え、カラムに吸着していた成分を溶出してＨＰ吸着画分を得た。 The resulting crude solder extract was concentrated under reduced pressure using an evaporator to remove acetic acid and ethanol to obtain a 5-fold concentrated extract. This was applied to a column (diameter: 40 mm, length: 300 mm) packed with DIAION HP20 (trade name, styrene-divinylbenzene chromatographic separation material) manufactured by Mitsubishi Chemical Corporation, and eluted with distilled water. Obtained. Further, the solvent was switched to a 50% ethanol aqueous solution, and the components adsorbed on the column were eluted to obtain an HP adsorption fraction.
前記工程で得られたハンダマ粗抽出物およびＨＰ吸着区分をそれぞれ凍結乾燥した。各々の凍結乾燥品をアセトニトリルにてそれぞれ１ｍｇ／ｍｌに溶解させた。それぞれのアセトニトリル溶解液についてＨＰＬＣ（高速液体クロマトグラフィー）を用いて分析を行った。測定条件はインタクト社製Ｃａｄｅｎｚａ ＣＤ−Ｃ１８（商品名、２５０×４．６ｍｍ）カラムを用い、流速１ｍ／ｍｉｎ、検出波長２６０ｎｍとし、移動層（Ａ）水／ＴＦＡ＝１００：０．１、（Ｂ）アセトニトリル／ＴＦＡ＝１００：０．１を０〜１２分までは（Ａ）：（Ｂ）＝９０：１０で、１２〜２０分までは（Ａ）：（Ｂ）＝６０：４０のリニアグラジエントで溶出を行った。 Each of the crude solder extract and HP adsorption section obtained in the above step was freeze-dried. Each lyophilized product was dissolved in acetonitrile at 1 mg / ml. Each acetonitrile solution was analyzed using HPLC (high performance liquid chromatography). The measurement conditions were a Cadenza CD-C18 (trade name, 250 × 4.6 mm) column manufactured by Intact, a flow rate of 1 m / min, a detection wavelength of 260 nm, a moving bed (A) water / TFA = 100: 0.1, ( B) Acetonitrile / TFA = 100: 0.1 from 0 to 12 minutes is (A) :( B) = 90: 10, and from 12 to 20 minutes is linear (A) :( B) = 60: 40 Elution was performed with a gradient.
ハンダマ粗抽出物とＨＰ吸着区分のそれぞれのサンプルの溶出パターンを図１、図２の矢印Ａ、矢印Ｂにて示す。図２は図１の種々の個別のアントシアニンのピーク部分を拡大して示したものである。図１及び図２によれば、ハンダマ粗抽出物ではそれぞれのアントシアニンのピークは非常に小さいものであった。これに対してＨＰ吸着区分の分析パターンでは各ピークが明瞭に出現することがわかった。 The elution patterns of the samples of the rough solder extract and the HP adsorption section are shown by arrows A and B in FIGS. FIG. 2 is an enlarged view of the peak portions of various individual anthocyanins in FIG. According to FIG. 1 and FIG. 2, each anthocyanin peak was very small in the handama crude extract. On the other hand, it was found that each peak clearly appears in the analysis pattern of the HP adsorption section.
図１及び図２のアントシアニンのピーク中のＮｏ．１およびＮｏ．２のアントシアニンを代表的に着目した。表１に、ピークＮｏ．１、ピークＮｏ．２について、ｔＲ（リテンションタイム：クロマトでサンプルを注入した後に、その画分がカラムから溶出するまでに要する時間）、ハンダマ粗抽出物５μｇの場合のピークの面積、ハンダマＨＰ２０吸着部５μｇの場合のピーク面積、並びに、相対面積比（吸着部／粗抽出部）を示す。 No. in the anthocyanin peak of FIGS. 1 and no. Two anthocyanins were typically noted. In Table 1, peak No. 1, peak no. 2 for tR (retention time: the time required for the fraction to elute from the column after injecting the sample by chromatography), the peak area in the case of 5 μg of the crude solder extract, and the case of 5 μg of the solder HP20 adsorption part The peak area and the relative area ratio (adsorption part / rough extraction part) are shown.
図１及び図２のピークパターン中のＮｏ．１およびＮｏ．２の画分についてＨＰ吸着区分／ハンダマ粗抽出部の面積比でみてみるとＮｏ．１のピークで３９．３倍、Ｎｏ．２のピークで１５．５倍に濃縮されていた。また、ＨＰ吸着区分について塩酸−メタノール法にてアントシアニンの定量を行ったところ、デルフィニジン相当量として１４．８％相当量であることがわかった。 No. 1 in the peak patterns of FIGS. 1 and no. As for the fraction of No. 2, the area ratio of the HP adsorption classification / handama rough extraction part is No. 19.3 peak, No. 1 The peak of 2 was concentrated 15.5 times. Moreover, when the anthocyanin was quantified by the hydrochloric acid-methanol method for the HP adsorption category, it was found that the equivalent amount of delphinidin was 14.8%.
これは、三菱化学株式会社製のＤＩＡＩＯＮ ＨＰ２０（商品名、スチレン−ジビニルベンゼン系クロマト分離材）を充填したカラムにより、アントシアニンが高濃度に濃縮されたことを示す。 This indicates that anthocyanins were concentrated to a high concentration by a column packed with DIAION HP20 (trade name, styrene-divinylbenzene chromatographic separation material) manufactured by Mitsubishi Chemical Corporation.
本発明のアントシアニン系色素抽出物の製造方法により得られたアントシアニン系色素抽出物は、粘性多糖類、クロロフィル、ＧＡＢＡの分離除去処理がなされているため、アントシアニン系色素抽出物は色調が安定であり、飲料の色付、酒の色付、ケーキ・パンの色付、米炊飯時の着色などあらゆる食品の加熱操作のあるなしにかかわらずに着色に利用でき、また、医薬品、化粧料の着色に利用できる。 The anthocyanin pigment extract obtained by the method for producing an anthocyanin pigment extract of the present invention has been subjected to separation and removal of viscous polysaccharides, chlorophyll, and GABA. Therefore, the color tone of the anthocyanin pigment extract is stable. Can be used for coloring foods with or without heating, such as coloring of beverages, coloring of liquor, coloring of cakes and breads, coloring when cooking rice, and for coloring of pharmaceuticals and cosmetics Available.
Claims (5)
（２）前記工程で得られた乾燥物をそのまま又は粉砕し、５０〜８０％エタノール水溶液を供し、クロロフィルを含有する抽出残渣と、ＧＡＢＡとアントシアニン系色素を含有するエタノール水溶液とに分別し、
（３）前記工程で得られたＧＡＢＡとアントシアニン系色素を含有するエタノール水溶液に対してエタノールを回収除去することによりクロロフィルを沈殿させて除去し、ＧＡＢＡとアントシアニン系色素が濃縮された濃縮液を取得し、
（４）前記工程で得られた濃縮液を、疎水成分の吸着機能を持つ吸着材カラムに供することによりアントシアニン系色素を吸着させ、素通りするＧＡＢＡ含有水溶液を除去し、 （５）次いで、前記吸着カラムに吸着されたアントシアニン系色素をエタノール水溶液で溶出することによりアントシアニン系色素を含有する吸着画分を取得することを特徴とするアントシアニン系色素抽出物の製造方法。 (1) Dry handama leaves,
(2) The dried product obtained in the above step is directly or pulverized, provided with a 50-80% aqueous ethanol solution, fractionated into an extraction residue containing chlorophyll, and an aqueous ethanol solution containing GABA and anthocyanin dyes,
(3) Precipitating and removing chlorophyll by recovering and removing ethanol from the ethanol aqueous solution containing GABA and anthocyanin dyes obtained in the previous step to obtain a concentrated liquid in which GABA and anthocyanin dyes are concentrated And
(4) The concentrated liquid obtained in the above step is applied to an adsorbent column having a function of adsorbing hydrophobic components to adsorb an anthocyanin dye and remove a GABA-containing aqueous solution that passes through. (5) Next, the adsorption A method for producing an anthocyanin dye extract comprising obtaining an adsorbed fraction containing an anthocyanin dye by eluting the anthocyanin dye adsorbed on a column with an aqueous ethanol solution.
該工程で得られたエタノール水溶液と前記工程（２）で得られたエタノール水溶液を混合し、次いで、前記工程（３）、（４）及び（５）を行う請求項１に記載のアントシアニン系色素抽出物の製造方法。 An aqueous ethanol solution is again applied to the extraction residue obtained in the step (2) to transfer the GABA and anthocyanin pigment still remaining in the extraction residue to the aqueous ethanol solution, and chlorophyll, which is a contaminant, is extracted to the extraction residue. Sort as
The anthocyanin pigment according to claim 1, wherein the aqueous ethanol solution obtained in the step and the aqueous ethanol solution obtained in the step (2) are mixed, and then the steps (3), (4) and (5) are performed. A method for producing an extract.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108041602A (en) * | 2018-01-16 | 2018-05-18 | 江苏省农业科学院 | A kind of anthocyanin function food additive and preparation method thereof |
| CN113970544A (en) * | 2021-10-22 | 2022-01-25 | 宁波市农业科学研究院 | Method and device for manufacturing plant source anthocyanin intelligent indicator strip |
| CN114702836A (en) * | 2022-04-23 | 2022-07-05 | 南京林业大学 | A kind of method for extracting and purifying pigment from jujube residue |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05194175A (en) * | 1992-01-20 | 1993-08-03 | Nonogawa Shoji Kk | Cosmetic |
| JPH07227246A (en) * | 1994-02-15 | 1995-08-29 | Sanei Gen F F I Inc | Simultaneous production of violet pigment from sweet potato and foodstuff product |
| JPH09255889A (en) * | 1996-03-27 | 1997-09-30 | Sanei Gen F F I Inc | Production of purple sweet potato pigment |
| JP2003159027A (en) * | 2001-11-27 | 2003-06-03 | National Agricultural Research Organization | How to color foods with potato anthocyanins |
| JP2003333990A (en) * | 2002-05-17 | 2003-11-25 | Ito En Ltd | Method for producing γ-aminobutyric acid-rich substance having sweet fragrance and γ-aminobutyric acid-rich substance having sweet fragrance obtained by the method |
| JP2006008665A (en) * | 2004-05-21 | 2006-01-12 | Toyo Shinyaku:Kk | Extract of stem and leaf of sweet potato |
| JP2006067945A (en) * | 2004-09-03 | 2006-03-16 | Sanei Gen Ffi Inc | Method for producing anthocyanin |
| JP2006117584A (en) * | 2004-10-21 | 2006-05-11 | Kanazawa Univ | Food and pharmaceutical composition using suizenjina |
| JP2008174459A (en) * | 2007-01-16 | 2008-07-31 | Maruzen Pharmaceut Co Ltd | Anti-aging agent, external preparation for skin and food and drink for beauty |
| JP2008255231A (en) * | 2007-04-05 | 2008-10-23 | Kanehide Bio Kk | Simultaneous production of fucoxanthin and fucoidan |
| JP2010509207A (en) * | 2006-11-03 | 2010-03-25 | クワンジュ インスティチュート オブ サイエンス アンド テクノロジー | Method for producing chlorophyll a and chlorin e6 |
-
2012
- 2012-02-15 JP JP2012030946A patent/JP5137220B1/en not_active Expired - Fee Related
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05194175A (en) * | 1992-01-20 | 1993-08-03 | Nonogawa Shoji Kk | Cosmetic |
| JPH07227246A (en) * | 1994-02-15 | 1995-08-29 | Sanei Gen F F I Inc | Simultaneous production of violet pigment from sweet potato and foodstuff product |
| JPH09255889A (en) * | 1996-03-27 | 1997-09-30 | Sanei Gen F F I Inc | Production of purple sweet potato pigment |
| JP2003159027A (en) * | 2001-11-27 | 2003-06-03 | National Agricultural Research Organization | How to color foods with potato anthocyanins |
| JP2003333990A (en) * | 2002-05-17 | 2003-11-25 | Ito En Ltd | Method for producing γ-aminobutyric acid-rich substance having sweet fragrance and γ-aminobutyric acid-rich substance having sweet fragrance obtained by the method |
| JP2006008665A (en) * | 2004-05-21 | 2006-01-12 | Toyo Shinyaku:Kk | Extract of stem and leaf of sweet potato |
| JP2006067945A (en) * | 2004-09-03 | 2006-03-16 | Sanei Gen Ffi Inc | Method for producing anthocyanin |
| JP2006117584A (en) * | 2004-10-21 | 2006-05-11 | Kanazawa Univ | Food and pharmaceutical composition using suizenjina |
| JP2010509207A (en) * | 2006-11-03 | 2010-03-25 | クワンジュ インスティチュート オブ サイエンス アンド テクノロジー | Method for producing chlorophyll a and chlorin e6 |
| JP2008174459A (en) * | 2007-01-16 | 2008-07-31 | Maruzen Pharmaceut Co Ltd | Anti-aging agent, external preparation for skin and food and drink for beauty |
| JP2008255231A (en) * | 2007-04-05 | 2008-10-23 | Kanehide Bio Kk | Simultaneous production of fucoxanthin and fucoidan |
Non-Patent Citations (1)
| Title |
|---|
| JPN6012028280; 椙山幹司 他: 'スイゼンジナの収量，ミネラルおよび機能性成分の生育時期別特徴' 九州沖縄農業研究成果情報 Ｎｏ．２１, 2006, Ｐａｇｅ．４７１-４７２ * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108041602A (en) * | 2018-01-16 | 2018-05-18 | 江苏省农业科学院 | A kind of anthocyanin function food additive and preparation method thereof |
| CN108041602B (en) * | 2018-01-16 | 2021-11-05 | 江苏省农业科学院 | A kind of anthocyanin functional food additive and preparation method thereof |
| CN113970544A (en) * | 2021-10-22 | 2022-01-25 | 宁波市农业科学研究院 | Method and device for manufacturing plant source anthocyanin intelligent indicator strip |
| CN114702836A (en) * | 2022-04-23 | 2022-07-05 | 南京林业大学 | A kind of method for extracting and purifying pigment from jujube residue |
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