JP2021503942A - ラクトバチルス−マリを用いてグルコース転移ステビオール配糖体を製造する方法 - Google Patents
ラクトバチルス−マリを用いてグルコース転移ステビオール配糖体を製造する方法 Download PDFInfo
- Publication number
- JP2021503942A JP2021503942A JP2020529723A JP2020529723A JP2021503942A JP 2021503942 A JP2021503942 A JP 2021503942A JP 2020529723 A JP2020529723 A JP 2020529723A JP 2020529723 A JP2020529723 A JP 2020529723A JP 2021503942 A JP2021503942 A JP 2021503942A
- Authority
- JP
- Japan
- Prior art keywords
- glucose
- transferred
- steviol glycoside
- lactobacillus
- mali
- 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.)
- Granted
Links
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Classifications
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- A—HUMAN NECESSITIES
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- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
Description
砂糖(白砂糖純度99%以上)を炭素源とし、酵母抽出物及びトウモロコシ浸漬液(Corn Steep Liquor)を窒素源とし、アミノ酸などを含有した栄養培地にラクトバチルス-マリ(Lactobacillus mali DSM20444、ATCC 27054、ATCC 27304)微生物を30℃、24時間培養した。培養液を8000rpmで10分間遠心分離して菌体と上澄み液を分離した後、上澄み液のみを取った。助酵素液を砂糖と反応させて砂糖加水分解の活性を確認し、上記助酵素液内に砂糖加水分解の活性を有する新規酵素が存在することを確認した。
ステビオール配糖体、砂糖を0.05Mの酢酸緩衝溶液に溶解した後、実施例1で準備したラクトバチルス-マリ菌株の助酵素液を添加して40℃で24時間反応させた。反応後、100℃で失活させた後、グルコース転移ステビオール配糖体の生産有無をHPLCで確認した。使用されたステビオール配糖体は、ステビオシド、ルブソシド、ズルコシドA、レバウジオシドA/C/D/E/F/Mであり、グルコース転移ステビオシド、グルコース転移ルブソシド、グルコース転移ズルコシドA、グルコース転移レバウジオシドA/C/D/E/F/Mを生成するかをHPLCで確認した。具体的には、図1〜図9に基づいてラクトバチルス-マリ菌株の助酵素液とステビオール配糖体の反応により新たに生成された物質を確認するためにHPLC/MS分析を行い、これらが糖転移ステビオール配糖体であることを確認した。HPLC/MS分析を行ったステビオール配糖体は、ステビオシド、レバウジオシドA/C/D/E/F/M、ルブソシド、ズルコシドAである。
ラクトバチルス-マリ菌株の助酵素液によるグルコース転移ステビオール配糖体の生産において、温度の影響性を評価した。砂糖とステビオール配糖体(ステビオシド、レバウジオシドA)を0.05Mの酢酸緩衝溶液(pH5.0)に溶解した後、上記助酵素液を添加して10〜80℃で24時間反応させた。反応が完了した後、溶液内のグルコース転移ステビオール配糖体の量を、HPLCを用いて分析した。
ラクトバチルス-マリ菌株の助酵素液によるグルコース転移ステビオール配糖体の生産において、pHの影響性を評価した。砂糖とステビオール配糖体を0.05Mの酢酸緩衝溶液(pH2.0-5.0)、リン酸塩緩衝溶液(pH6.0)、トリス緩衝溶液(pH7.0-8.0)、炭酸水素ナトリウム緩衝溶液(pH9.0)に溶解した後、上記助酵素液を添加してpH2〜pH9の範囲で24時間反応した。反応が完了した後、グルコース転移ステビオール配糖体の量を、HPLCを用いて分析した。
ラクトバチルス-マリ助酵素液によるステビオール配糖体の濃度によるグルコース転移ステビオール配糖体の生産を評価した。砂糖とステビオール配糖体(ステビオシド、レバウジオシドA)を酢酸緩衝溶液(pH5.0)に溶解させ、40℃で24時間反応させた。反応が完了した後、グルコース転移ステビオール配糖体の生成を、HPLCを用いて分析した。
砂糖とステビオール配糖体を酢酸緩衝溶液(pH5.0)に溶解した後、上記助酵素液を添加して40℃で24時間反応させる。反応溶液を100℃で失活させた後、0.45μmのフィルタを利用して不純物を除去した。HP20レジンを用いてグルコース1個が転移されたステビオール配糖体(ステビオシド、レバウジオシドA)をそれぞれ純粋分離した。分離されたグルコース転移ステビオシドとグルコース転移レバウジオシドAの結合構造を分析するために、1H/13C NMR、Homonuclear correlation spectroscopy(COSY)、Total correlation spectroscopy(TOCSY)、Heteronuclear single-quantum coherence(HSQC)、及びheteronuclear multiple-bond correlation(HMBC)で確認し、その結果(1H/13C NMR、COSYそしてHMBC)を下記表1と表2に示した。
Claims (10)
- ラクトバチルス-マリ(Lactobacillius mali)微生物またはその培養物を用いた、グルコース転移ステビオール配糖体の製造方法。
- 前記方法は、前記ラクトバチルス-マリ微生物またはその培養物の存在の下で、砂糖とステビオール配糖体を反応させる段階を含む、請求項1に記載のグルコース転移ステビオール配糖体の製造方法。
- 前記ステビオール配糖体は、ステビオシド、ルブソシド、ズルコシドA、レバウジオシドA、レバウジオシドC、レバウジオシドD、レバウジオシドE、レバウジオシドF、及びレバウジオシドMからなる群から選択される1つ以上である、請求項2に記載のグルコース転移ステビオール配糖体の製造方法。
- 前記砂糖とステビオール配糖体を反応させる段階は、pH3〜8及び10〜60℃で行われる、請求項2に記載のグルコース転移ステビオール配糖体の製造方法。
- 前記グルコース転移ステビオール配糖体は、ステビオール配糖体の19-OHの位置に結合されたグルコースを通じてグルコースがα-(1,6)結合により連結されて付加されたステビオール配糖体である、請求項1に記載のグルコース転移ステビオール配糖体の製造方法。
- 前記グルコース転移ステビオール配糖体は、グルコースを1〜4個含む、請求項5に記載のグルコース転移ステビオール配糖体の製造方法。
- 請求項1〜6のいずれか一項に記載の方法で製造された、グルコース転移ステビオール配糖体。
- 前記グルコース転移ステビオール配糖体は、グルコース転移ステビオシド、グルコース転移ルブソシド、グルコース転移ズルコシドA、グルコース転移レバウジオシドA、グルコース転移レバウジオシドC、グルコース転移レバウジオシドD、グルコース転移レバウジオシドE、グルコース転移レバウジオシドF、及びグルコース転移レバウジオシドMからなる群から選択される1つ以上である、請求項7に記載のグルコース転移ステビオール配糖体。
- ラクトバチルス-マリ(Lactobacillius mali)微生物またはその培養物を含む、グルコース転移ステビオール配糖体生産用組成物。
- 請求項1〜6のいずれか一項に記載の方法で製造されたグルコース転移ステビオール配糖体を含む、甘味料。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4219571A (en) * | 1978-06-15 | 1980-08-26 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing a sweetener |
WO2013019050A2 (ko) * | 2011-07-29 | 2013-02-07 | 한국생명공학연구원 | 신규한 α-글루코실 스테비오사이드 및 이의 제조 방법 |
WO2016144175A1 (en) * | 2015-03-10 | 2016-09-15 | Rijksuniversiteit Groningen | Methods for the enzymatic modification of steviol glycosides, modified steviol glycosides obtainable thereby, and the use thereof as sweeteners |
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KR950002868B1 (ko) | 1991-11-21 | 1995-03-27 | 주식회사 미원 | 프락토실 스테비오사이드의 제조방법 및 그를 주성분으로 하는 감미료 |
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BR112013023831A2 (pt) * | 2011-03-22 | 2020-09-29 | Purecircle Usa Inc. | composição de glicosídeo de esteviol glicosilado como um intensificador de sabor e aroma |
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KR101724569B1 (ko) * | 2011-07-29 | 2017-04-07 | 한국생명공학연구원 | 루부소사이드 생산하는 신규 제조방법 |
CN102492757B (zh) * | 2011-11-25 | 2014-04-09 | 中国农业大学 | 一种用β-环糊精葡萄糖基转移酶提高甜菊糖苷味质的方法 |
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TWI559925B (en) * | 2015-08-05 | 2016-12-01 | Univ Nat Taiwan | Novel lactobacillus mali aps1 and use thereof |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4219571A (en) * | 1978-06-15 | 1980-08-26 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing a sweetener |
WO2013019050A2 (ko) * | 2011-07-29 | 2013-02-07 | 한국생명공학연구원 | 신규한 α-글루코실 스테비오사이드 및 이의 제조 방법 |
WO2016144175A1 (en) * | 2015-03-10 | 2016-09-15 | Rijksuniversiteit Groningen | Methods for the enzymatic modification of steviol glycosides, modified steviol glycosides obtainable thereby, and the use thereof as sweeteners |
Non-Patent Citations (1)
Title |
---|
CARBOHYDRATE RESEARCH, vol. Vol.440-441, JPN6021020819, 2017, pages 51 - 62, ISSN: 0004520150 * |
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