WO2005038038A1 - Process for producing ascorbic acid glycoside - Google Patents

Process for producing ascorbic acid glycoside

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Publication number
WO2005038038A1
WO2005038038A1 PCT/JP2004/011690 JP2004011690W WO2005038038A1 WO 2005038038 A1 WO2005038038 A1 WO 2005038038A1 JP 2004011690 W JP2004011690 W JP 2004011690W WO 2005038038 A1 WO2005038038 A1 WO 2005038038A1
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WIPO (PCT)
Prior art keywords
ascorbic acid
glycoside
acid glycoside
cellulose
producing
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Application number
PCT/JP2004/011690
Other languages
French (fr)
Japanese (ja)
Inventor
Toshihiko Hagiwara
Chisato Mayama
Original Assignee
Nichirei Foods Inc.
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Publication date
Application filed by Nichirei Foods Inc. filed Critical Nichirei Foods Inc.
Publication of WO2005038038A1 publication Critical patent/WO2005038038A1/en

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    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin

Definitions

  • the present invention relates to a method for producing ascorbic acid glycoside
  • ascorbic acid has attracted attention because of its ability to scavenge reactive oxygen and to promote collagen synthesis. In itself, ascorbic acid is easily oxidized and decomposed by heat and light. Recently, it has been clarified that ascorbic acid glycoside has higher stability than ascorbic acid, and its application to cosmetics and the like has been carried out.
  • L-ascorbic acid 2-gonolecoside which is an ascorbic acid glycoside, has been considered as a food additive and is considered as a food additive (as of May 23, 2003).
  • JP-B-48-38158 describes a method of synthesizing ascorbic acid dalcoside or oligoside by adding maltose or oligosaccharide, starch hydrolyzate containing starch to L-ascorbinate and adding a microorganism or the like belonging to the genus Aspergillus. It is done.
  • An object of the present invention is to develop a method for producing a food material strength ascorbic acid glycoside, and to develop a method for producing an ascorbic acid glycoside using a ⁇ -Dalcocinole saccharide compound as a substrate. It is.
  • a sugar compound in addition to ascorbic acid, a sugar compound, in particular cellulose which is a main component of plant cell wall ( ⁇ -1,4- Gnorecan was used. Since this cellulose is a main component of fruits, its applicability in industrial fields such as fruit juice production is also extremely high.
  • a cellulolytic enzyme was used as an enzyme catalyzing a glycosidation reaction.
  • a cellulolytic enzyme was used as an enzyme catalyzing a glycosidation reaction.
  • a method for producing an ascorbyl glycoside which comprises adding an enzyme having cellulose degradability to a solution containing j3-gonoleucosyl sugar complex and iscolubic acid to obtain an ascorbyl glycoside.
  • the present invention relates to a method for producing ascorbic acid glycoside.
  • Examples of the dalcosyl sugar compound include ⁇ -1, 4-glucan (cellulose), ⁇ -1, 3-gonolecan, ⁇ -1, 6-gonolecan (pustran) and the like, with cellulose being the most preferable.
  • Cellulose is a component that "is present in the largest amount in organic matter produced in nature", as described in the section "Cellulose” in Iwanami Chemical Dictionary 5th Edition. Cellulose is also the main component of pressed fruit produced in the industrial juice production process, and in many cases it has been discarded.
  • the solution containing cellulose and ascorbic acid used in the present invention is not limited to the solution prepared from experimental reagents and the like, and it is possible to use, for example, pressed fruit or juice, vegetable fiber component or pressed fruit. A combination of plant origin and reagents may also be used. Asconoleviic acid concentration of the fruit to be used at that time is usually 0.03 w / w% or more. For example, acerola, mandarin orange, kiwi can be mentioned.
  • Cellulose-degrading enzymes used in the present invention are not limited to food grade enzymes, and may be purified enzymes such as laboratory reagents. However, particularly effective ones are enzymes derived from Aspergillus spp. Or Trichoderma sp., And cellulase-containing enzymes or highly purified cellulase.
  • the seeds were removed from the fruit of acerola, which is known to have a high content of ascorbic acid, and 5 g of puree obtained by grinding the remaining edible portion was lg (30000 U) of cellulase ("CELLASE A” manufactured by Amano). By adding, ascorbic acid glycoside was produced. After reacting for 30 minutes at room temperature (25 ° C.), ascorbic acid glycoside was confirmed by HPLC in the same manner as in Example 1. The results are shown in FIG.
  • the present invention it is possible to easily and efficiently glycosylate ascorbic acid using cellulose, which is a general natural raw material, to obtain a highly stable ascorbyl glycoside. By this, it is possible to stably and stably supply ascorbic acid glycoside. Furthermore, the increase in stability of ascorbic acid makes it possible to suppress the discoloration of juice caused by the reaction of ascorbic acid.
  • FIG. 1 is a diagram showing a chromatogram in HPLC of a reaction solution in which a cellulose degrading enzyme of a food grade enzyme agent is added to experimental reagents cellulose and ascorbic acid (VC).
  • Fig. 2 shows the reaction mixture obtained by adding cellulolytic enzyme to pressed acerola fruit.
  • FIG. 3 is a view showing the difference in the residual rate between ascorbic acid (VC) and iscorbic acid glycoside.

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  • 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)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

A process for producing an ascorbic acid glycoside from a food material; and in particular a process for producing an ascorbic acid glycoside with the use of a β-glucosylsaccharide compound as a substrate. In this process, not only ascorbic acid but also a β-glucosylsaccharide compound, especially cellulose(β-1,4-glucan) being a main constituent component of botanical cell wall, is used as a substrate of enzymic reaction for obtaining an ascorbic acid glycoside.

Description

明 細 書  Specification
ァスコルビン酸配糖体の製造方法  Process for producing ascorbic acid glycoside
技術分野  Technical field
[0001] 本発明は、ァスコルビン酸配糖体の製造方法に関する  TECHNICAL FIELD [0001] The present invention relates to a method for producing ascorbic acid glycoside
背景技術  Background art
[0002] 近年、ァスコルビン酸は活性酸素消去能やコラーゲン合成の促進効果を有してレ、 ることから注目を浴びている。本来、ァスコルビン酸は、熱や光によって容易に酸化さ れ、分解される。最近になって、ァスコルビン酸配糖体はァスコルビン酸よりも高い安 定性を持つことが明らかとなり、化粧品等への応用が行われている。また、ァスコルビ ン酸配糖体である L-ァスコルビン酸 2-グノレコシドは、食品添加物として、指定が検討 されてレ、る（2003年 5月 23日時点）。  [0002] In recent years, ascorbic acid has attracted attention because of its ability to scavenge reactive oxygen and to promote collagen synthesis. In itself, ascorbic acid is easily oxidized and decomposed by heat and light. Recently, it has been clarified that ascorbic acid glycoside has higher stability than ascorbic acid, and its application to cosmetics and the like has been carried out. In addition, L-ascorbic acid 2-gonolecoside, which is an ascorbic acid glycoside, has been considered as a food additive and is considered as a food additive (as of May 23, 2003).
[0003] このため、ァスコルビン酸配糖体の工業的な製造方法として、 α _グノレコシル糖ィ匕 合物等を用いた方法が既に開発されている（特許第 2926412号公報)。また、特公昭 48— 38158号公報には Lーァスコルビン酸塩にマルトース又はオリゴ糖、含有澱粉加 水分解物を加えァスペルギルス属に属する微生物等を加えてァスコルビン酸ダルコ シド又はオリゴシドを合成する方法が記載されている。  [0003] Therefore, as an industrial method for producing ascorbic acid glycoside, a method using an α_gonolecosyl sugar compound or the like has already been developed (Japanese Patent No. 2926412). In addition, JP-B-48-38158 describes a method of synthesizing ascorbic acid dalcoside or oligoside by adding maltose or oligosaccharide, starch hydrolyzate containing starch to L-ascorbinate and adding a microorganism or the like belonging to the genus Aspergillus. It is done.
[0004] 従来、ァスコルビン酸配糖体を製造するには、基質として —グノレコシル糖ィ匕合物 ではなぐ ひ-グノレコシル糖ィ匕合物が無くてはならないと考えられてきた。そのため、こ れらの方法では、基質としてァスコルビン酸のほかにひ-ダルコシル糖化合物を必要 としていた。すなわち、果実中のァスコルビン酸を配糖化して、充分量のァスコルビン 酸配糖体を得るためにはひ -グノレコシノレ糖化合物の添加が必須であった。  Heretofore, it has been considered that, in order to produce an ascorbic acid glycoside, a gonoglucosyl sugar complex as a substrate must be present. Therefore, in these methods, in addition to ascorbic acid as a substrate, a mono-darcosyl sugar compound was required. That is, in order to obtain a sufficient amount of ascorbic acid glucoside by glycation of ascorbic acid in fruits, it was essential to add a glycosylcoside sugar compound.
発明の開示  Disclosure of the invention
[0005] 本発明の課題は、食品素材力らァスコルビン酸配糖体を製造する方法を開発する こと、及び基質として β一ダルコシノレ糖化合物を用いてァスコルビン酸配糖体を製造 する方法を開発することにある。本発明では、前記課題を解決するために、ァスコル ビン酸配糖体を得るための酵素反応の基質として、ァスコルビン酸のほかに、 ーグ 糖化合物、特に植物の細胞壁の主要構成成分であるセルロース（ β -1,4- グノレカン）を用いた。このセルロースは、果実の主要構成成分であるため、果汁製造 等の産業分野における応用可能性も極めて高い。 An object of the present invention is to develop a method for producing a food material strength ascorbic acid glycoside, and to develop a method for producing an ascorbic acid glycoside using a β-Dalcocinole saccharide compound as a substrate. It is. In the present invention, in order to solve the above-mentioned problems, as a substrate of an enzyme reaction for obtaining ascorbic acid glycoside, in addition to ascorbic acid, a sugar compound, in particular cellulose which is a main component of plant cell wall (Β -1,4- Gnorecan was used. Since this cellulose is a main component of fruits, its applicability in industrial fields such as fruit juice production is also extremely high.
[0006] 更に、配糖ィ匕反応を触媒する酵素としてセルロース分解酵素を用いた。その結果、 ァスコルビン酸、 /3 _ダルコシル糖化合物（特にセルロース）、セルロース分解酵素を 用いることで天然食品素材からァスコルビン酸配糖体を得ることができた。  [0006] Furthermore, a cellulolytic enzyme was used as an enzyme catalyzing a glycosidation reaction. As a result, it was possible to obtain an ascorbic acid glucoside from a natural food material by using a ascorbic acid, a / 3_ dalcosyl sugar compound (especially cellulose) and a cellulolytic enzyme.
[0007] すなわち、本発明は  That is, the present invention
(1) j3—グノレコシル糖ィ匕合物とァスコルビン酸を含む溶液に、セルロース分解能を有 する酵素を添加し、ァスコルビン酸配糖体を得ることを特徴とするァスコルビン酸配糖 体の製造方法、  (1) A method for producing an ascorbyl glycoside, which comprises adding an enzyme having cellulose degradability to a solution containing j3-gonoleucosyl sugar complex and iscolubic acid to obtain an ascorbyl glycoside.
(2) β—ダルコシル糖化合物がセルロースであることを特徴とする (1)記載のァスコノレ ビン酸配糖体の製造方法、  (2) The method for producing an asconolenoic acid glycoside according to (1), wherein the β-dalcosyl sugar compound is cellulose.
(3) セルロース分解能を有する酵素力 ァスペルギルス属あるいはトリコデルマ属の 菌体に由来し、セルラーゼを含む酵素群あるいは高純度に精製されたセルラーゼで あることを特徴とする（1)又は（2)記載のァスコルビン酸配糖体の製造方法 に関する。  (3) Enzyme power having cellulose degradability Enzyme group derived from Aspergillus spp. Or Trichoderma spp. And containing cellulase or cellulase purified to high purity (1) or (2) The present invention relates to a method for producing ascorbic acid glycoside.
[0008] ーダルコシル糖化合物としては、 β— 1 , 4ーグルカン（セルロース）、 β -1 , 3—グ ノレカン、 β— 1 , 6—グノレカン (プスッラン)等があるが最も好ましいのはセルロースであ る。セルロースは、岩波理化学辞典第 5版「セルロース」の項に記載されているように 、「自然界に産出する有機物中もっとも多量に存在する」成分である。また、セルロー スは工業的な果汁製造工程で発生する果実圧搾物の主成分でもあり、廃棄されてい る例も多い。  [0008] Examples of the dalcosyl sugar compound include β-1, 4-glucan (cellulose), β-1, 3-gonolecan, β-1, 6-gonolecan (pustran) and the like, with cellulose being the most preferable. . Cellulose is a component that "is present in the largest amount in organic matter produced in nature", as described in the section "Cellulose" in Iwanami Chemical Dictionary 5th Edition. Cellulose is also the main component of pressed fruit produced in the industrial juice production process, and in many cases it has been discarded.
[0009] 従って、セルロースを基質として用いてァスコルビン酸配糖体を製造することは、原 料の入手が容易であるば力 ではなぐ廃棄されている有機物の有効利用に資する ものである。また、セルロースを含む果実圧搾物などにセルロース分解酵素を添加す ることで、ァスコルビン酸配糖体を含有する食品の工業的な生産が可能となる。 発明を実施するための最良の形態  [0009] Therefore, producing ascorbic acid glycoside using cellulose as a substrate contributes to the effective use of the discarded organic material that can not be disposed of by force if the raw material can be easily obtained. In addition, the addition of a cellulolytic enzyme to a pressed fruit or the like containing cellulose enables industrial production of a food containing an ascorbic acid glycoside. BEST MODE FOR CARRYING OUT THE INVENTION
[0010] 本発明に用いるセルロースとァスコルビン酸を含む溶液は、実験用試薬等から調 製した溶液に限定されず、例えば果実の圧搾物や果汁、植物の繊維分や圧搾物で もよぐ植物由来物と試薬との組み合わせでも良い。その際に用いる果実のァスコノレ ビン酸濃度は、通常、 0.03w/w%以上であれば良ぐ例えばァセロラ、ミカン、キウイ が挙げられる。 [0010] The solution containing cellulose and ascorbic acid used in the present invention is not limited to the solution prepared from experimental reagents and the like, and it is possible to use, for example, pressed fruit or juice, vegetable fiber component or pressed fruit. A combination of plant origin and reagents may also be used. Asconoleviic acid concentration of the fruit to be used at that time is usually 0.03 w / w% or more. For example, acerola, mandarin orange, kiwi can be mentioned.
[0011] 本発明に用いるセルロース分解酵素は食品用酵素に限定されず、実験用試薬等 の精製された酵素でも良レ、。しかし、特に効果的なものは、ァスペルギルス属あるい はトリコデルマ属の菌体に由来し、セルラーゼを含む酵素群あるいは高純度に精製 されたセルラーゼである。  Cellulose-degrading enzymes used in the present invention are not limited to food grade enzymes, and may be purified enzymes such as laboratory reagents. However, particularly effective ones are enzymes derived from Aspergillus spp. Or Trichoderma sp., And cellulase-containing enzymes or highly purified cellulase.
実施例  Example
[0012] 以下、本発明を実施例により更に詳細に説明する。  Hereinafter, the present invention will be described in more detail by way of examples.
実施例 1  Example 1
セルロース 0.25gと L-ァスコルビン酸 40 mgを、 pH 3.0のリン酸緩衝液 2.0 mlに溶 解した後、食品添加物のセルラーゼ（アマノ社製「セルラーゼ八」：ァスペルギルス属 菌体由来） 0.25g (7500U)を添カ卩し、 25°Cの室温にて 1時間反応させた。この反応液 を高速液体クロマトグラフィー（HPLC)を用いて分析し、ァスコルビン酸とは溶出時間 の異なるァスコルビン酸配糖体のピークを確認した。この結果を図 1に示す。  After dissolving 0.25 g of cellulose and 40 mg of L-ascorbic acid in 2.0 ml of phosphate buffer pH 3.0, the food additive cellulase (Amano's “Cellulase 8”: derived from Aspergillus spp. Cells) 0.25 g ( 7500 U) was added and reacted at room temperature of 25 ° C. for 1 hour. The reaction solution was analyzed by high performance liquid chromatography (HPLC) to confirm the peak of ascorbic acid glycoside having a different elution time from that of ascorbic acid. The results are shown in Figure 1.
[0013] HPLCでの分析条件を以下に示す。 The analytical conditions for HPLC are shown below.
カラム： ODSカラム（4.6 X 250mm)  Column: ODS column (4.6 x 250 mm)
流速 ： l.Oml/min  Flow rate: l.Oml / min
移動相： lOOmMリン酸緩衝液（pH 3.0)  Mobile phase: lOOmM phosphate buffer (pH 3.0)
検出 ：フォトダイオードアレー  Detection: Photodiode array
[0014] 実施例 2 Example 2
ァスコルビン酸含量が高いことで知られるァセロラの果実から種子を取り除き、残り の可食部を磨り潰すことで得たピューレ 5gに対し、セルラーゼ（アマノ社製「セルラー ゼ A」）lg (30000U)を添加して、ァスコルビン酸配糖体を製造した。室温 (25°C)にて 30分間反応させた後、実施例 1と同様に HPLCにてァスコルビン酸配糖体を確認した 。この結果を図 2に示す。  The seeds were removed from the fruit of acerola, which is known to have a high content of ascorbic acid, and 5 g of puree obtained by grinding the remaining edible portion was lg (30000 U) of cellulase ("CELLASE A" manufactured by Amano). By adding, ascorbic acid glycoside was produced. After reacting for 30 minutes at room temperature (25 ° C.), ascorbic acid glycoside was confirmed by HPLC in the same manner as in Example 1. The results are shown in FIG.
[0015] 図 2からみると、ァスコルビン酸 (VC)とァスコルビン酸配糖体とを加算した総ァスコル ビン酸量の 45%が配糖体となっていることが確認された。なお、ァスコルビン酸 (VC) よりァスコルビン酸配糖体の方が安定性を持つことを実証するために、両者を放置し た場合の残存率を測定したが、その結果を示したものが図 3である。これを見ると 48 時間たつとァスコルビン酸 (VC)は 10%程度しか残存していないのに対して、ァスコル ビン酸配糖体は 50%程度残存していることがわかる。 As seen from FIG. 2, it was confirmed that 45% of the total amount of ascorbic acid, which is the sum of ascorbic acid (VC) and the ascorbic acid glycoside, is a glycoside. In addition, ascorbic acid (VC) In order to demonstrate that ascorbic acid glycoside is more stable, the residual rate when both were left standing was measured, and the results are shown in FIG. According to this, it can be seen that ascorbic acid (VC) remains at only about 10% after 48 hours, whereas ascorbic acid glycoside remains at about 50%.
産業上の利用可能性  Industrial applicability
[0016] 本発明により、セルロースという一般的な天然素材を用いて、容易に効率よくァスコ ルビン酸を配糖ィ匕し、安定性の高いァスコルビン酸配糖体を得ることが可能となる。こ れにより、ァスコルビン酸配糖体を安価に安定的に供給することができる。更に、ァス コルビン酸の安定性が高まることで、ァスコルビン酸の反応によって起こる果汁の退 色を抑制することが可能となる。 According to the present invention, it is possible to easily and efficiently glycosylate ascorbic acid using cellulose, which is a general natural raw material, to obtain a highly stable ascorbyl glycoside. By this, it is possible to stably and stably supply ascorbic acid glycoside. Furthermore, the increase in stability of ascorbic acid makes it possible to suppress the discoloration of juice caused by the reaction of ascorbic acid.
図面の簡単な説明  Brief description of the drawings
[0017] [図 1]第 1図は、実験用試薬のセルロースとァスコルビン酸 (VC)に食品用酵素剤の セルロース分解酵素を添加した反応液の HPLCでのクロマトグラムを示す図である。  [0017] [FIG. 1] FIG. 1 is a diagram showing a chromatogram in HPLC of a reaction solution in which a cellulose degrading enzyme of a food grade enzyme agent is added to experimental reagents cellulose and ascorbic acid (VC).
[図 2]第 2図は、ァセロラ果実圧搾物にセルロース分解酵素を添加した反応液の  [Fig. 2] Fig. 2 shows the reaction mixture obtained by adding cellulolytic enzyme to pressed acerola fruit.
[図 3]第 3図は、ァスコルビン酸 (VC)とァスコルビン酸配糖体との残存率の差異を示 す図である。 [FIG. 3] FIG. 3 is a view showing the difference in the residual rate between ascorbic acid (VC) and iscorbic acid glycoside.

Claims

請求の範囲 The scope of the claims
[1] /3—ダルコシル糖化合物とァスコルビン酸を含む溶液に、セルロース分解能を有する 酵素を添加し、ァスコルビン酸配糖体を得ることを特徴とするァスコルビン酸配糖体 の製造方法。  [1] A method for producing an ascorbyl acid glycoside, which comprises adding an enzyme having cellulose degradability to a solution containing a / 3- dalcosyl sugar compound and ascorbic acid to obtain an ascorbyl acid glycoside.
[2] β一ダルコシノレ糖化合物がセルロースであることを特徴とする請求の範囲第 1項記載 のァスコルビン酸配糖体の製造方法。  [2] The method for producing an ascorbic acid glycoside according to claim 1, wherein the β1-darcosinole sugar compound is cellulose.
[3] セルロース分解能を有する酵素が、ァスペルギルス属あるいはトリコデルマ属の菌体 に由来し、セルラーゼを含む酵素群あるいは高純度に精製されたセルラーゼである ことを特徴とする請求の範囲第 1項又は第 2項記載のァスコルビン酸配糖体の製造 方法。 [3] The enzyme having cellulose degradability is a cellulase-containing enzyme group or highly purified cellulase which is derived from a cell of Aspergillus sp. Or Trichoderma sp. A method for producing an ascorbic acid glycoside according to item 2.
PCT/JP2004/011690 2003-10-16 2004-08-13 Process for producing ascorbic acid glycoside WO2005038038A1 (en)

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JP2006245132A (en) 2005-03-01 2006-09-14 Sumitomo Electric Ind Ltd Semiconductor opto-electrical element and its manufacturing method of semiconductor opto-electrical element

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JPH06284897A (en) * 1992-09-30 1994-10-11 Kurabo Ind Ltd Production of beta-form polyphenol glycoside
WO2003057707A1 (en) * 2001-12-28 2003-07-17 Suntory Limited 2-o-( -d-glucopyranosyl)ascorbic acid, process for its production, and foods and cosmetics containing compositions comprising it

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06284897A (en) * 1992-09-30 1994-10-11 Kurabo Ind Ltd Production of beta-form polyphenol glycoside
WO2003057707A1 (en) * 2001-12-28 2003-07-17 Suntory Limited 2-o-( -d-glucopyranosyl)ascorbic acid, process for its production, and foods and cosmetics containing compositions comprising it

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