JP4216688B2 - アスコルビン酸配糖体の製造方法 - Google Patents
アスコルビン酸配糖体の製造方法 Download PDFInfo
- Publication number
- JP4216688B2 JP4216688B2 JP2003356713A JP2003356713A JP4216688B2 JP 4216688 B2 JP4216688 B2 JP 4216688B2 JP 2003356713 A JP2003356713 A JP 2003356713A JP 2003356713 A JP2003356713 A JP 2003356713A JP 4216688 B2 JP4216688 B2 JP 4216688B2
- Authority
- JP
- Japan
- Prior art keywords
- ascorbic acid
- cellulose
- glycoside
- acid glycoside
- enzyme
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 title claims description 84
- 229960005070 ascorbic acid Drugs 0.000 title claims description 54
- 239000011668 ascorbic acid Substances 0.000 title claims description 53
- 235000010323 ascorbic acid Nutrition 0.000 title claims description 53
- -1 ascorbic acid glycoside Chemical class 0.000 title claims description 35
- 229930182470 glycoside Natural products 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000001913 cellulose Substances 0.000 claims description 20
- 229920002678 cellulose Polymers 0.000 claims description 20
- 108090000790 Enzymes Proteins 0.000 claims description 16
- 102000004190 Enzymes Human genes 0.000 claims description 16
- 229940088598 enzyme Drugs 0.000 claims description 16
- 235000013399 edible fruits Nutrition 0.000 claims description 9
- 108010059892 Cellulase Proteins 0.000 claims description 6
- 229940106157 cellulase Drugs 0.000 claims description 6
- 230000001461 cytolytic effect Effects 0.000 claims description 6
- 241000228212 Aspergillus Species 0.000 claims description 5
- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 claims description 4
- 235000014837 Malpighia glabra Nutrition 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 241000223259 Trichoderma Species 0.000 claims description 3
- 230000004304 visual acuity Effects 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims 1
- 241001640002 Malpighia emarginata Species 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 11
- 125000000188 beta-D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 235000015203 fruit juice Nutrition 0.000 description 4
- 240000003394 Malpighia glabra Species 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002498 Beta-glucan Polymers 0.000 description 2
- 108010084185 Cellulases Proteins 0.000 description 2
- 102000005575 Cellulases Human genes 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 101710156496 Endoglucanase A Proteins 0.000 description 2
- 229920001503 Glucan Polymers 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- MLSJBGYKDYSOAE-DCWMUDTNSA-N L-Ascorbic acid-2-glucoside Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1O MLSJBGYKDYSOAE-DCWMUDTNSA-N 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Description
更に、配糖化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、アスコルビン酸、β−グルコシル糖化合物(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アスコルビン酸配糖体を得ることができた。
(1) β−グルコシル糖化合物とア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、アスコルビン酸配糖体を得ることを特徴とするアスコルビン酸配糖体の製造方法、
(2) β−グ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)記載のアスコルビン酸配糖体の製造方法、
(3) セルロース分解能を有する酵素が、ア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)記載のアスコルビン酸配糖体の製造方法
に関する。
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い。しかし、特に効果的なものは、ア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。
以下、本発明を実施例により更に詳細に説明する。
カラム:ODSカラム(4.6×250mm)
流速 :1.0ml/min
移動相:100mMリン酸緩衝液(pH 3.0)
検出 :フォトダイオードアレー
室温(25℃)にて30分間反応させた後、実施例1と同様にHPLCにてアスコルビン酸配糖体を確認した。この結果を図2に示す。
Claims (2)
- セルロースとア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、アスコルビン酸配糖体を得ることを特徴とするアスコルビン酸配糖体の製造方法であって、該セルロースとアスコルビン酸を含む溶液がアセロラ果実由来物である、上記方法。
- セルロース分解能を有する酵素が、ア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項1記載のアスコルビン酸配糖体の製造方法。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003356713A JP4216688B2 (ja) | 2003-10-16 | 2003-10-16 | アスコルビン酸配糖体の製造方法 |
PCT/JP2004/011690 WO2005038038A1 (ja) | 2003-10-16 | 2004-08-13 | アスコルビン酸配糖体の製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003356713A JP4216688B2 (ja) | 2003-10-16 | 2003-10-16 | アスコルビン酸配糖体の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005117959A JP2005117959A (ja) | 2005-05-12 |
JP4216688B2 true JP4216688B2 (ja) | 2009-01-28 |
Family
ID=34463221
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003356713A Expired - Lifetime JP4216688B2 (ja) | 2003-10-16 | 2003-10-16 | アスコルビン酸配糖体の製造方法 |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP4216688B2 (ja) |
WO (1) | WO2005038038A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7803645B2 (en) | 2005-03-01 | 2010-09-28 | Sumitomo Electric Industries, Ltd. | Semiconductor light-emitting device and a method for manufacturing the same |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0736759B2 (ja) * | 1992-09-30 | 1995-04-26 | 倉敷紡績株式会社 | β型ポリフェノール配糖体の製法 |
ATE535537T1 (de) * | 2001-12-28 | 2011-12-15 | Suntory Holdings Ltd | 2-o-(-d-glucopyranosyl)ascorbinsäure, verfahren zu ihrer herstellung , sowie lebensmittel und kosmetika, die diese umfassende zusammensetzungen enthalten |
-
2003
- 2003-10-16 JP JP2003356713A patent/JP4216688B2/ja not_active Expired - Lifetime
-
2004
- 2004-08-13 WO PCT/JP2004/011690 patent/WO2005038038A1/ja active Application Filing
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7803645B2 (en) | 2005-03-01 | 2010-09-28 | Sumitomo Electric Industries, Ltd. | Semiconductor light-emitting device and a method for manufacturing the same |
Also Published As
Publication number | Publication date |
---|---|
WO2005038038A1 (ja) | 2005-04-28 |
JP2005117959A (ja) | 2005-05-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Slámová et al. | “Sweet flavonoids”: Glycosidase-catalyzed modifications | |
US4668626A (en) | Method for the preparation of branched cyclodextrins | |
Krisch et al. | Characterization of a β-glucosidase with transgalactosylation capacity from the zygomycete Rhizomucor miehei | |
Tarahomjoo et al. | Surfactant production by an enzymatic method | |
Céliz et al. | Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media | |
AU709427B2 (en) | Beta-glucosidase from filamentous fungi, and uses thereof | |
Karthaus et al. | Cellulase-catalysed glycosylation reactions: simple route towards a highly selective synthesis of oligosaccharides | |
JP4216688B2 (ja) | アスコルビン酸配糖体の製造方法 | |
Nolte et al. | Glycosylation of caffeic acid and structural analogues catalyzed by novel glucansucrases from Leuconostoc and Weissella species | |
AU618588B2 (en) | Process for obtaining aroma components and aromas from their precursors of a glycosidic nature, and aroma components and aromas thereby obtained | |
Wojciechowska et al. | Application of transgalactosylation activity of β-galactosidase from Kluyveromyces lactis for the synthesis of ascorbic acid galactoside | |
Fujisue et al. | Preparation and antioxidative activity of 1, 5-anhydrofructose | |
JP5339500B2 (ja) | マンノースの精製方法 | |
Mendes et al. | Regioselective monohydrolysis of per-O-acetylated-1-substituted-β-glucopyranosides catalyzed by immobilized lipases | |
Hashmi et al. | Antimelanogenesis activity of polyphenol glycoside synthesized by transglycosylation reaction of CGTase from Xanthomonas Campestris | |
Biely et al. | Enzymic α-galactosylation of a cyclic glucotetrasaccharide derived from alternan | |
EP2186904B1 (en) | Method for producing glucose derivatives | |
Yang et al. | Convenient synthesis of alkyl and phenylalkyl β-d-glucopyranosides using facile and novel biocatalysts of plant origin | |
Grizard et al. | Enzymatic synthesis and structure determination of NEO‐FOS | |
Karnišová Potocká et al. | New assay of α-l-rhamnosidase | |
Kim et al. | Enzymatic synthesis of alkyl α-2-deoxyglucosides by alkyl alcohol resistant α-glucosidase from Aspergillus niger | |
JP3796809B2 (ja) | フェノール系配糖体、及びその製造方法 | |
JP2004010621A (ja) | フェノール化合物のルチノース配糖体を有効成分として含有する美白剤 | |
JP3787002B2 (ja) | フェノール化合物のルチノース配糖体の製造方法 | |
Dini et al. | Enzymatic production of fructooligosaccharides from phytoenzymes of Ananas Comosus waste by using response surface methodology: one factor |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20050526 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20051101 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080708 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080908 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20081021 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20081106 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4216688 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111114 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121114 Year of fee payment: 4 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131114 Year of fee payment: 5 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |