WO2005038038A1 - Procede de production de glycoside d'acide ascorbique - Google Patents

Procede de production de glycoside d'acide ascorbique

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
ascorbic acid
glycoside
acid glycoside
cellulose
producing
Prior art date
Application number
PCT/JP2004/011690
Other languages
English (en)
Japanese (ja)
Inventor
Toshihiko Hagiwara
Chisato Mayama
Original Assignee
Nichirei Foods Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nichirei Foods Inc. filed Critical Nichirei Foods Inc.
Publication of WO2005038038A1 publication Critical patent/WO2005038038A1/fr

Links

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

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.

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)

Abstract

L'invention concerne un procédé de production de glycoside d'acide ascorbique à partir d'un produit alimentaire ; et en particulier un procédé de production d'un glycoside d'acide ascorbique au moyen d'un composé β-glucosylsaccharide utilisé en tant que substrat. Ce procédé consiste à utiliser non seulement de l'acide ascorbique mais également un composé β-glucosylsaccharide, en particulier de la cellulose (β-1,4-glucane) étant un composant principal de la paroi cellulaire botanique, en tant que substrat de réaction enzymatique afin d'obtenir un glycoside d'acide ascorbique.
PCT/JP2004/011690 2003-10-16 2004-08-13 Procede de production de glycoside d'acide ascorbique WO2005038038A1 (fr)

Applications Claiming Priority (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
JP2003-356713 2003-10-16

Publications (1)

Publication Number Publication Date
WO2005038038A1 true WO2005038038A1 (fr) 2005-04-28

Family

ID=34463221

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2004/011690 WO2005038038A1 (fr) 2003-10-16 2004-08-13 Procede de production de glycoside d'acide ascorbique

Country Status (2)

Country Link
JP (1) JP4216688B2 (fr)
WO (1) WO2005038038A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006245132A (ja) 2005-03-01 2006-09-14 Sumitomo Electric Ind Ltd 半導体光素子および半導体光素子を作製する方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06284897A (ja) * 1992-09-30 1994-10-11 Kurabo Ind Ltd β型ポリフェノール配糖体の製法
WO2003057707A1 (fr) * 2001-12-28 2003-07-17 Suntory Limited Acide 2-o-($g(b)-d-glucopyranosyl) ascorbique, procede de production, aliments et produits cosmetiques contenant des compositions comprenant cet acide

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06284897A (ja) * 1992-09-30 1994-10-11 Kurabo Ind Ltd β型ポリフェノール配糖体の製法
WO2003057707A1 (fr) * 2001-12-28 2003-07-17 Suntory Limited Acide 2-o-($g(b)-d-glucopyranosyl) ascorbique, procede de production, aliments et produits cosmetiques contenant des compositions comprenant cet acide

Also Published As

Publication number Publication date
JP2005117959A (ja) 2005-05-12
JP4216688B2 (ja) 2009-01-28

Similar Documents

Publication Publication Date Title
Itoh et al. Preparation of D-psicose from D-fructose by immobilized D-tagatose 3-epimerase
GB2165549A (en) Branched cyclodextrins
Zhang et al. Enzymatic transformation of 2-O-α-D-glucopyranosyl-L-ascorbic acid by α-cyclodextrin glucanotransferase from recombinant Escherichia coli
US6087131A (en) β-glucosidase from filamentous fungi, and uses thereof
US4908311A (en) Process for enzymatic preparation of cellooligosaccharides
WO2005038038A1 (fr) Procede de production de glycoside d'acide ascorbique
Cui et al. Efficient enzymatic preparation of esculentoside B following condition optimization by response surface methodology
Ohnuma et al. A glycosynthase derived from an inverting chitinase with an extended binding cleft
Fujisue et al. Preparation and antioxidative activity of 1, 5-anhydrofructose
Hashmi et al. Antimelanogenesis activity of polyphenol glycoside synthesized by transglycosylation reaction of CGTase from Xanthomonas Campestris
Cairns et al. Protein-carbohydrate interactions leading to hydrolysis and transglycosylation in plant glycoside hydrolase family 1 enzymes
JP2001112496A (ja) セロオリゴ糖の製造法
JP2845386B2 (ja) 内分岐大環状サイクロデキストリンを含む大環状サイクロデキストリン混合物の製造方法
US6339146B1 (en) Cycloalkylated beta-glucoside
JPS63226294A (ja) セロビオ−スの製造法
Maruo et al. Enzymatic synthesis of high purity maltotetraose using moranoline (1-deoxynojirimycin)
Grizard et al. Enzymatic synthesis and structure determination of NEO‐FOS
TWI837950B (zh) 芒果苷醣苷及其製備方法
Dintinger et al. Synthesis of β-mercaptoethyl-glycosides by enzymatic reverse hydrolysis and transglycosylation
KR100443411B1 (ko) 베타글리코시다제를 이용한 진세노사이드 ｆ1의 제조방법
KR20030094757A (ko) 베타글리코시다제를 이용한 진세노사이드 ｆ₂또는 컴파운드 케이의 제조방법
KR100671291B1 (ko) 베타갈락토시다제를 이용하여 진세노사이드 ｆ1을제조하는 방법
JP3630378B2 (ja) ガラクトシルグリセロール類の製造方法
JP3796810B2 (ja) フェノール系配糖体の製造方法
Karnišová Potocká et al. Apiose-Relevant Glycosidases. Catalysts 2021, 11, 1251

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

DPEN Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase