ID | 116602 |
Author |
Miura, Kaori
LAIMU Corporation
Matsuno, Hiroaki
Prefectural University of Hiroshima
Iwaoka, Yuji
Okayama Prefectural University
Ito, Hideyuki
Okayama Prefectural University
Tai, Akihiro
Prefectural University of Hiroshima|Tokushima University
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Keywords | ascorbic acid derivatives
degranulation
passive cutaneous anaphylaxis
structure-activity relationship
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Content Type |
Journal Article
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Description | 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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Journal Title |
Molecules
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ISSN | 14203049
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Publisher | MDPI
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Volume | 26
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Issue | 15
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Start Page | 4684
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Published Date | 2021-08-03
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Rights | 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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EDB ID | |
DOI (Published Version) | |
URL ( Publisher's Version ) | |
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language |
eng
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TextVersion |
Publisher
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departments |
Bioscience and Bioindustry
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