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Molecules 2017, 22(12), 2202; https://doi.org/10.3390/molecules22122202

Anti-Allergic Activity of Monoacylated Ascorbic Acid 2-Glucosides

1
Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, 5562 Nanatsuka-cho, Shobara, Hiroshima 727-0023, Japan
2
Faculty of Health and Welfare Science, Okayama Prefectural University, 111 Kuboki, Soja, Okayama 719-1197, Japan
*
Author to whom correspondence should be addressed.
Received: 30 October 2017 / Revised: 22 November 2017 / Accepted: 7 December 2017 / Published: 12 December 2017
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Abstract

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. View Full-Text
Keywords: ascorbic acid derivatives; anti-allergic activity; degranulation; hyaluronidase; passive cutaneous anaphylaxis ascorbic acid derivatives; anti-allergic activity; degranulation; hyaluronidase; passive cutaneous anaphylaxis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Miura, K.; Morishita, Y.; Matsuno, H.; Aota, Y.; Ito, H.; Tai, A. Anti-Allergic Activity of Monoacylated Ascorbic Acid 2-Glucosides. Molecules 2017, 22, 2202.

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