ID | 117746 |
Author |
Miura, Kaori
Prefectural University of Hiroshima
Morishita, Yuta
Prefectural University of Hiroshima
Matsuno, Hiroaki
Prefectural University of Hiroshima
Aota, Yusuke
Prefectural University of Hiroshima
Ito, Hideyuki
Okayama Prefectural University
Tai, Akihiro
Prefectural University of Hiroshima
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Keywords | ascorbic acid derivatives
anti-allergic activity
degranulation
hyaluronidase
passive cutaneous anaphylaxis
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Content Type |
Journal Article
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Description | 2-O-α-D-Glucopyranosyl-L-ascorbic acid (AA-2G) is one of the stable ascorbic acid (AA) derivatives known as provitamin C agents. We have previously 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 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) in order to improve the bioavailability of AA-2G. In this study, 6-sAcyl-AA-2G and 6-bAcyl-AA-2G per se showed the inhibitory effects on hyaluronidase activity and degranulation. 6-sAcyl-AA-2G exhibited strong inhibitory effects on hyaluronidase activity and degranulation in a concentration-dependent manner, and the inhibitory effects tended to become stronger with increasing length of the acyl chain. 2-O-α-D-Glucopyranosyl-6-O-hexadecanoyl-L-ascorbic acid (6-sPalm-AA-2G), which has a straight C16 acyl chain, was the most potent effective for inhibition of hyaluronidase activity and for inhibition of degranulation among the 6-sAcyl-AA-2G derivatives and the two isomers of 6-sPalm-AA-2G. Furthermore, percutaneous administration of 6-sPalm-AA-2G significantly inhibited IgE-mediated passive cutaneous anaphylaxis reaction in mice. These findings suggest that 6-sPalm-AA-2G will be useful for treatment of allergies.
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Journal Title |
Molecules
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ISSN | 14203049
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Publisher | MDPI
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Volume | 22
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Issue | 12
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Start Page | 2202
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Published Date | 2017-12-12
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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 (http://creativecommons.org/licenses/by/4.0/).
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DOI (Published 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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