Modification of Ascorbic Acid Using Transglycosylation Activity of Bacillus stearothermophilus Maltogenic Amylase to Enhance Its Oxidative Stability

• Published in: Journal of agricultural and food chemistry 2002-05, Vol.50 (11), p.3309-3316
• Main Authors: 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
• Format: Article
• Language: English
• Subjects: Acarbose - metabolism; Animals; Antioxidants - metabolism; Antioxidants - pharmacology; Ascorbate Oxidase - metabolism; Ascorbic Acid - chemistry; Ascorbic Acid - metabolism; Ascorbic Acid - pharmacology; Biological and medical sciences; Chickens; Chromatography; Copper - chemistry; Drug Stability; Food additives; Food industries; Fundamental and applied biological sciences. Psychology; General aspects; Geobacillus stearothermophilus - enzymology; Glycoside Hydrolases - metabolism; Glycosylation; Lipid Peroxidation - drug effects; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oxidation-Reduction; Poultry Products; Trisaccharides - metabolism
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf011550z

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. Keywords: Acarbose; antioxidant; ascorbic acid; Bacillus stearothermophilus maltogenic amylase; maltosyl-ascorbic acid; transglycosylation; lipid oxidation