Radical Scavenging Activity against 1, 1-Diphenyl-2-picrylhydrazyl of Ascorbic Acid 2-Glucoside(AA-2G)and 6-Acyl-AA-2G
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概要
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The radical scavenging activity of the stable derivatives, which are O-substituted at the C-2 position of ascorbic acid(AA), against 1, 1-diphenyl-2-picrylhydrazyl(DPPH)was evaluated in buffer under different pH conditions, and compared with those of AA and α-tocopherol. AA was shown to have 50% radical scavenging ability(EC_<50>)at a concentration of 2.2×10^<-5>M against 0.1mM DPPH in 60% ethanol. Ascorbyl 6-palmitate, a lipophilic AA derivative which has a free endiol group and is therefore unstable, also showed potent radical scavenging activity with EC_<50> of 2.9×10^<-5>M. A typical lipophilic antioxidant, α-tocopherol gave a similar EC_<50> value as that of AA. In contrast, ascorbyl 2, 6-dipalmitate, AA 2-phosphate and AA 2-sulfate exhibited negligible scavenging activity. On the other hand, 2-O-α-D-glucopyranosyl-L-ascorbic acid(AA-2G)and a series of 6-O-acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids(6-Acyl-AA-2G)themselves exhibited the radical scavenging activity of EC_<50> : 6.1×10^<-5>M and 4.4×10^<-5>-5.9×10^<-5>M, respectively, although their activities were lower than that of AA. Among 6-Acyl-AA-2G derivatives, the EC_<50> values tended to decrease with increasing length of their acyl carbon group. Increasing pH of the buffer resulted in decrease in the scavenging activity of all compounds tested as expected. We speculate that the difference in the radical scavenging activity of derivatives O-substituted at the C-2 position of AA may be ascribed to the linkage type of the substituent group to the endiol-lactone resonance system and the degree of dissociation of the C-3 proton.
- 公益社団法人日本薬学会の論文
- 2001-05-01
著者
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Yamamoto Itaru
岡山大学 薬学部免疫医薬品化学
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FUJINAMI Yoshihito
Department of First Forensic Science, National Research Institute of Police Science
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YAMAMOTO Itaru
Department of Radiology, Kanazawa Medical University
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Yamamoto I
Okayama Univ. Okayama Jpn
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TAI Akihiro
Department of Immunochemistry, Faculty of Pharmaceutical Sciences, Okayama University
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Fujinami Yoshihito
Department Of Immunochemistry Faculty Of Pharmaceutical Sciences Okayama University
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Fujinami Yoshihito
Department Of First Forensic Science National Research Institute Of Police Science
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Yamamoto Itaru
Department Of Immunochemistry Faculty Of Pharmaceutical Science Okayama University
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Tai A
Department Of Immunochemistry Faculty Of Pharmaceutical Sciences Okayama University
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Tai Akihiro
Department Of Immunochemistry Division Of Pharmaceutical Sciences Okayama University Graduate School
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Yamamoto I
Department Of Immunochemistry Division Of Pharmaceutical Sciences Okayama University Graduate School
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