Modification of ascorbic acid using transglycosylation activity of Bacillus stearothermophilus maltogenic amylase to enhance its oxidative stability

Hee Kyung Bae, Soo Bok Lee, Cheon Seok Park, Jae Hoon Shim, Hye Young Lee, Myo Jeong Kim, Jin Sook Baek, Hoe Jin Roh, Jin Hwan Choi, Eun Ok Choe, Dong Uk Ahn, Kwan Hwa Park

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an α-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and 13C NMR analyses revealed that the structures of the transfer products were 6-O-α-D-glucosyl- (2) and 6-O-α-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-α-acarviosine-D-glucosyl- (4) and 2-O-α-acarviosine- D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu2+ ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.

Original languageEnglish
Pages (from-to)3309-3316
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume50
Issue number11
DOIs
Publication statusPublished - 2002 May 22

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glucan 1,4-alpha-maltohydrolase
Geobacillus stearothermophilus
ascorbic acids
acarbose
Bacilli
oxidative stability
maltotriose
amylases
Ascorbic Acid
ascorbic acid
Acarbose
antioxidants
Antioxidants
chemical derivatives
ascorbate oxidase
oxidation
glycosidic linkages
patties
breast meat
chicken meat

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Cite this

Bae, Hee Kyung ; Lee, Soo Bok ; Park, Cheon Seok ; Shim, Jae Hoon ; Lee, Hye Young ; Kim, Myo Jeong ; Baek, Jin Sook ; Roh, Hoe Jin ; Choi, Jin Hwan ; Choe, Eun Ok ; Ahn, Dong Uk ; Park, Kwan Hwa. / Modification of ascorbic acid using transglycosylation activity of Bacillus stearothermophilus maltogenic amylase to enhance its oxidative stability. In: Journal of Agricultural and Food Chemistry. 2002 ; Vol. 50, No. 11. pp. 3309-3316.
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abstract = "Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an α-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and 13C NMR analyses revealed that the structures of the transfer products were 6-O-α-D-glucosyl- (2) and 6-O-α-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-α-acarviosine-D-glucosyl- (4) and 2-O-α-acarviosine- D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu2+ ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.",
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Modification of ascorbic acid using transglycosylation activity of Bacillus stearothermophilus maltogenic amylase to enhance its oxidative stability. / Bae, Hee Kyung; Lee, Soo Bok; Park, Cheon Seok; Shim, Jae Hoon; Lee, Hye Young; Kim, Myo Jeong; Baek, Jin Sook; Roh, Hoe Jin; Choi, Jin Hwan; Choe, Eun Ok; Ahn, Dong Uk; Park, Kwan Hwa.

In: Journal of Agricultural and Food Chemistry, Vol. 50, No. 11, 22.05.2002, p. 3309-3316.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Modification of ascorbic acid using transglycosylation activity of Bacillus stearothermophilus maltogenic amylase to enhance its oxidative stability

AU - Bae, Hee Kyung

AU - Lee, Soo Bok

AU - Park, Cheon Seok

AU - Shim, Jae Hoon

AU - Lee, Hye Young

AU - Kim, Myo Jeong

AU - Baek, Jin Sook

AU - Roh, Hoe Jin

AU - Choi, Jin Hwan

AU - Choe, Eun Ok

AU - Ahn, Dong Uk

AU - Park, Kwan Hwa

PY - 2002/5/22

Y1 - 2002/5/22

N2 - Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an α-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and 13C NMR analyses revealed that the structures of the transfer products were 6-O-α-D-glucosyl- (2) and 6-O-α-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-α-acarviosine-D-glucosyl- (4) and 2-O-α-acarviosine- D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu2+ ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.

AB - Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an α-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and 13C NMR analyses revealed that the structures of the transfer products were 6-O-α-D-glucosyl- (2) and 6-O-α-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-α-acarviosine-D-glucosyl- (4) and 2-O-α-acarviosine- D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu2+ ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.

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