ID | 116602 |
著者 |
Miura, Kaori
LAIMU Corporation
Matsuno, Hiroaki
Prefectural University of Hiroshima
Iwaoka, Yuji
Okayama Prefectural University
Ito, Hideyuki
Okayama Prefectural University
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キーワード | ascorbic acid derivatives
degranulation
passive cutaneous anaphylaxis
structure-activity relationship
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資料タイプ |
学術雑誌論文
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抄録 | Allergy is an excessive immune response to a specific antigen. Type I allergies, such as hay fever and food allergies, have increased significantly in recent years and have become a worldwide problem. We previously reported that an ascorbic acid derivative having palmitoyl and glucosyl groups, 2-O-α-D-glucopyranosyl-6-O-hexadecanoyl-L-ascorbic acid (6-sPalm-AA-2G), showed inhibitory effects on degranulation in vitro and on the passive cutaneous anaphylaxis (PCA) reaction in mice. In this study, several palmitoyl derivatives of ascorbic acid were synthesized and a structure–activity relationship study was performed to discover more potent ascorbic acid derivatives with degranulation inhibitory activity. 6-Deoxy-2-O-methyl-6-(N-hexadecanoyl)amino-L-ascorbic acid (2-Me-6-N-Palm-AA), in which a methyl group was introduced into the hydroxyl group at the C-2 position of ascorbic acid and in which the hydroxyl group at the C-6 position was substituted with an N-palmitoyl group, exhibited much higher inhibitory activity for degranulation in vitro than did 6-sPalm-AA-2G. 2-Me-6-N-Palm-AA strongly inhibit the PCA reaction in mice at lower doses than those of 6-sPalm-AA-2G. These findings suggest that 2-Me-6-N-Palm-AA may be a promising therapeutic candidate for allergic diseases.
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掲載誌名 |
Molecules
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ISSN | 14203049
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出版者 | MDPI
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巻 | 26
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号 | 15
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開始ページ | 4684
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発行日 | 2021-08-03
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権利情報 | This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
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言語 |
eng
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著者版フラグ |
出版社版
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部局 |
生物資源系
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