type: misc

label: url

en: 3-O-Dodecyl-L-ascorbic acidの抗アレルギー作用

ja: 3-O-Dodecyl-L-ascorbic acidの抗アレルギー作用

en: Vitamins

ja: ビタミン


en: アスコルビン酸(ビタミンC)誘導体

ja: アスコルビン酸(ビタミンC)誘導体

en: BIO INDUSTRY

ja: 月刊バイオインダストリー


en: アスコルビン酸誘導体を用いた医薬品開発への可能性

ja: アスコルビン酸誘導体を用いた医薬品開発への可能性


en: Antiallergic activity of 6-deoxy-2-O-methyl-6-(N-hexadecanoyl)amino-L-ascorbic acid


en: Applied research from basic research using ascorbic acid derivatives

ja: アスコルビン酸誘導体を用いた基礎研究から応用研究まで

en: L-Ascorbic acid (AsA) is an important antioxidant in food and biological systems, but it is unstable under various oxidative conditions, resulting in its rapid degradation. Therefore, the development of many stable AsA derivatives has been attempted. Among them, ascorbic acid 2-glucoside (AA-2G) has been approved by the Japanese Government as a quasi-drug principal ingredient in skin care and a food additive and it has been used widely in cosmetics and health foods in Japan. AA-2G is a provitamin C agent that exhibits vitamin C activity in vitro and in vivo after its enzymatic hydrolysis to AsA by α-glucosidase. 6-O-Acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids having a straight-acyl chain of varying length from C4 to C18 (6-sAcyl-AA-2G) and a branched-acyl chain of varying length from C6 to C16 (6-bAcyl-AA-2G) are lipophilic stable AsA derivatives for improving the bioavailability of AA-2G. 6-sAcyl-AA-2G and 6-bAcyl-AA-2G exert usually known vitamin C functions efficiently in vitro  and in vivo. Recently, AsA derivatives immobilized on a resin to let proteins recognize characteristic chemical structures of AsA have also been synthesized as new tools for identifying target proteins of AsA. In this mini review, the author presents researches using these AsA derivatives in applied fields from basic fields.


en: モノアシル化アスコルビン酸グルコシドの抗アレルギー作用

ja: モノアシル化アスコルビン酸グルコシドの抗アレルギー作用


en: 高濃度アスコルビン酸点滴療法における抗がん薬としてのアスコルビン酸2-グルコシド


en: Creation of ascorbic acid derivatives and possible their application to drug development

ja: アスコルビン酸誘導体の創製とその医薬品開発応用への可能性(日本薬学会第136回シンポジウム「ビタミンのケミカルバイオロジー研究」)


en: 高濃度エリソルビン酸による酸化ストレス誘導性の抗がん作用

ja: 高濃度エリソルビン酸による酸化ストレス誘導性の抗がん作用


en: ビタミンC 再生経路と酸化ストレス

ja: ビタミンC 再生経路と酸化ストレス


en: シクロデキストリングルカノトランスフェラーゼとアミログルコシダーゼを用いた高効率的かつ位置選択的なエリソルビン酸グルコシドの合成


en: 高分子触媒によるDMF中アスコルビン酸2-グルコシドの部位選択的モノアシル化

ja: 高分子触媒によるDMF中アスコルビン酸2-グルコシドの部位選択的モノアシル化


en: Antioxidant properties of 2-O-substituted ascorbic acid derivatives

ja: 2-O-置換型アスコルビン酸誘導体の抗酸化特性

en: The aim of this study was to characterize the antioxidant properties of three ascorbic acid (AsA) derivatives O-substituted at the C-2 position of AsA: ascorbic acid 2-glucoside (AA-2G), ascorbic acid 2-phosphate (AA-2P), and ascorbic acid 2-sulfate (AA-2S). The radical-scavenging activities of these AsA derivatives and some common low molecular-weight antioxidants such as uric acid and reduced glutathione (GSH) against 1,1-diphenyl-picrylhydrazyl (DPPH) radical, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS^<・+>) or galvinoxyl radical were kinetically and stoichiometrically evaluated under pH-controlled conditions. AA-2G, AA-2P and AA-2S slowly and continuously reacted with DPPH radical and ABTS^<・+>, but not with galvinoxyl radical. They effectively reacted with DPPH radical under acidic conditions and with ABTS^<・+> under neutral conditions. In contrast, AsA immediately quenched all species of radicals tested at all pH values. The reactivity of Trolox, a water-soluble vitamin E analogue, was comparable to that of AsA in terms of kinetics and stoichiometrics. Uric acid and GSH exhibited long-lasting radical-scavenging activity against these radicals under certain pH conditions. The radical-scavenging profiles of AA-2G, AA-2P and AA-2S were closer to those of uric acid and GSH rather than to that of AsA. The number of radicals scavenged by one molecule of the AsA derivatives was equal to or greater than that by AsA or Trolox under the appropriate conditions. Furthermore, inhibitory effects of AA-2G, AA-2P and AA-2S on 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced oxidative hemolysis of sheep erythrocytes were studied and were compared with those of AsA and other antioxidants. The order of the inhibition efficiency was AA-2S≥Trolox=uric acid≥AA-2P>AA-2G=AsA>GSH. Although the reactivity of the AsA derivatives against AAPH-derived peroxyl radical (ROO^・) was much lower than that of AsA, the derivatives exerted equal or more potent protective effects on AAPH-induced hemolysis. In addition, the AsA derivatives were found to react per se with DPPH radical and ABTS^<・+> and ROO^・, not via AsA as an intermediate. These results suggest that the AsA derivatives per se act as biologically effective antioxidants under moderate oxidative stress and that AA-2G and AA-2P may be able to act under severe oxidative stress after enzymatic conversion to AsA in vivo.


en: 少量の水を含むDMF中におけるアスコルビン酸2-グルコシドのプロテアーゼによるモノアシル化


en: Design and application of novel stable lipophilic ascorbic acid derivatives

ja: 親油性安定型アスコルビン酸誘導体の創製とその特性に関する研究

en: L-Ascorbic acid (AsA), vitamin C, possesses many biological activities, but it readily decomposes upon exposure to heat, UV light, metal ions, and oxidants. Therefore, Yamamoto and Muto et al. have developed a stable AsA derivative, 2-O-α-D-glucopyranosyl-L-ascorbic acid (AA-2G). AA-2G has been approved by the Japanese Government as a quasi-drug principal ingredient in skin care and as a food additive and is currently being used as a medical additive in commercial cosmetics. This stable AsA derivative exhibits vitamin C activity in vitro and in vivo after enzymatic hydrolysis to AsA by α-glucosidase. Recently, we have synthesized two types of monoacylated derivatives of AA-2G, 6-O-acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids having a straight-acyl chain (6-sAcyl-AA-2G) and a branched-acyl chain (6-bAcyl-AA-2G), in order to improve the bioavailability of AA-2G. These derivatives showed satisfactory stability in neutral solution comparable to that of AA-2G, and had radical scavenging activity per se. The lipophilicity of 6-sAcyl- and 6-bAcyl-AA-2G was increased with increasing length of their acyl group. 6-sAcyl- and 6-bAcyl-AA-2G with an appropriate length of the acyl chain group exhibited antiscorbutic activity in guinea pigs and skin permeability superior to that of AA-2G in a human living skin equivalent model. At a lower concentration than AA-2G, 6-sAcyl- and 6-bAcyl-AA-2G enhanced both dibutyryl cyclic AMP- and nerve growth factor-induced neurite outgrowth in PC 12 cells, antigen-specific antibody production in murine splenic cells and collagen synthesis in human skin fibroblasts, and inhibited melanogenesis in B16 mouse melanoma cells. It is necessary to metabolize the derivatives by α-glucosidase at least to demonstrate these biological activities. These results indicate that 6-sAcyl- and 6-bAcyl-AA-2G are readily available sources of AsA activity in vitro and in vivo, may be useful as an effective pharmacological agent and as a promising food additive.


en: 2-O-置換型アスコルビン酸誘導体によるフリーラジカル誘導性赤血球溶血反応の抑制


en: プロビタミンC剤の新しい利用法

ja: プロビタミンC剤の新しい利用法

en: Seibutsu-kogaku Kaishi

ja: 生物工学会誌


en: Design and application of novel ascorbic acid derivatives

ja: 親油性安定型アスコルビン酸誘導体の開発と応用

en: Bioscience & Industry

ja: バイオサイエンスとインダストリー


en: アスコルビン酸(ビタミンC)誘導体の開発動向

ja: アスコルビン酸(ビタミンC)誘導体の開発動向

en: Vitamins


en: ビタミンCとがんとの関係

ja: ビタミンCとがんとの関係

en: 化学

ja: 化学


en: 新しいビタミン製剤の研究開発動向

ja: 新しいビタミン製剤の研究開発動向

en: Nihon Rinsho. Japanese Journal of Clinical Medicine

ja: 日本臨牀