Formation of a stable l-ascorbic acid α-glucoside by mammalian α-glucosidase-catalyzed transglucosylation

Yamamoto, Ichiro; Muto, Norio; Nagata, Emi; Nakamura, Tomoe Y.; Suzuki, Yukio

doi:10.1016/0304-4165(90)90171-r

Cited by 110 publications

(64 citation statements)

References 20 publications

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“…[19][20][21] Since the hydroxyl group binding to the carbon at position 2 in ascorbic acid is protected by glucose, AA-2G is refractory to oxidation, and is therefore more stable than ascorbic acid under various conditions. 22) We have observed that combined usage of the medium-soluble fraction of RJ with AA-2G increased the collagen production much more than the combination of the medium-soluble fraction of RJ with ascorbic acid.…”

mentioning

confidence: 99%

Identification of a Collagen Production-promoting Factor from an Extract of Royal Jelly and Its Possible Mechanism

Koya‐Miyata

Okamoto

Ushio

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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We have previously shown that royal jelly (RJ) promoted collagen production by skin fibroblasts in the presence of ascorbic acid-2-O-alpha-glucoside (AA-2G). In this study, we purified the honeybee RJ-derived collagen production-promoting factor (HBRJ-CPF) from an alkali-solubilized fraction of RJ by C18 reverse-phase column chromatography. The elution profile by the C18 column chromatography and the molecular mass of the purified HBRJ-CPF material coincided with those of 10-hydroxy-2-decenoic acid (10H2DA). We then examined the collagen productionpromoting activities of several commercially available fatty acids contained in RJ. We found that 10H2DA and 10-hydroxydecanoic acid increased the collagen production in a dose-dependent manner. Furthermore, 10H2DA induced the fibroblast cell line, NHDF, to produce transforming growth factor-1 (TGF-1) which is an important factor for collagen production. As expected, the collagen production-promoting activity of 10H2DA was neutralized by the anti-TGF-1 antibody. These result suggest that HBRJ-CPF identified as 10H2DA promoted the collagen production of AA-2G-treated fibroblasts by inducing TGF-1 production.

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confidence: 99%

Identification of a Collagen Production-promoting Factor from an Extract of Royal Jelly and Its Possible Mechanism

Koya‐Miyata

Okamoto

Ushio

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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“…It is there fore concluded that AsA released from AA-2G by a glucosidase is involved in the stimulation of the immune response. We have shown that rat splenic homogenates have moderate enzymatic activity to hydrolyze AA-2G (4) and that the solubilized membrane fraction of murine splenocytes also has a-glucosidase activity (I. Yamamoto et al, unpublished data). We have also demonstrated that a-glucosidase activity in the medium supplemented with 10010 FCS is extremely low and not high enough to cleave the glucoside bond of AA-2G (9).…”

Section: Discussionmentioning

confidence: 94%

“…AA-2G is one of the most promising AsA derivatives (4,5), because it shows remark ably high stability against thermal and oxidative degrada tion in vitro (6), and it is easily converted into AsA in vivo by enzymatic cleavage (7). AA-2G was shown to act as an effective antiscorbutic vitamin in guinea pigs (7,8) and to stimulate the collagen synthesis in human skin fibroblasts in vitro (9).…”

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confidence: 99%

Enhancement by Ascorbic Acid 2-Glucoside or Repeated Additions of Ascorbate of Mitogen-Induced IgM and IgG Productions by Human Peripheral Blood Lymphocytes

Tanaka

Muto

Gohda

et al. 1994

Japanese Journal of Pharmacology

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ABSTRACT-In this study, the effect of ascorbic acid 2-glucoside (AA-2G), a stable derivative of ascorbic acid (AsA), or repeated additions of ascorbate on antibody productions by human peripheral blood lym phocytes (PBLs) was examined, and the physiological function of AsA was evaluated. When human PBLs were stimulated with Staphylococcus aureus Cowan I or pokeweed mitogen, AA-2G remarkably increased the numbers of IgM and IgG-secreting cells which were detected by enzyme-linked immunospot assay. Although a single addition of ascorbate was without effect, the effect of AA-2G was remarkably inhibited by the addition of castanospermine, an a-glucosidase inhibitor; and moreover, repeated additions of AsA to the culture medium during the culture period enhanced the response to the same level as did a single addi tion of AA-2G. These results indicate that AsA has the ability to stimulate the immunoglobulin productions by AA-2G. The phytohemagglutinin-induced proliferative response of PBLs was also stimulated by AA 2G. The intracellular AsA content in PBLs cultured with AA-2G was maintained at relatively high levels dur ing the culture period, whereas the content with a single dose of AsA reached nearly zero by the end of the experiment. These in vitro findings suggest that AA-2G and AsA function as potent immunostimulators of antibody production in humans and that the intracellular AsA content is a key parameter for establishing the immune response of PBLs.

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“…), a stable ascorbic acid derivative developed by Yamamoto et al, [1][2][3][4] has been approved by the Japanese Government as a quasi-drug principal ingredient for skin care and as a food additive, and is now widely used as a medical additive in commercial cosmetics. AA-2G exhibits vitamin C activity in vitro and in vivo after enzymatic hydrolysis to ascorbic acid (AA, Fig.…”

Section: -O--d-glucopyranosyl-l-ascorbic Acid (Aa-2gmentioning

confidence: 99%

Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Three Solvent Systems

Tai

Iwaoka

Mori

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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Formation of a stable l-ascorbic acid α-glucoside by mammalian α-glucosidase-catalyzed transglucosylation

Cited by 110 publications

References 20 publications

Identification of a Collagen Production-promoting Factor from an Extract of Royal Jelly and Its Possible Mechanism

Identification of a Collagen Production-promoting Factor from an Extract of Royal Jelly and Its Possible Mechanism

Enhancement by Ascorbic Acid 2-Glucoside or Repeated Additions of Ascorbate of Mitogen-Induced IgM and IgG Productions by Human Peripheral Blood Lymphocytes

Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Three Solvent Systems

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