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Open AccessArticle

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.
Molecules 2017, 22(12), 2202; https://doi.org/10.3390/molecules22122202
Received: 30 October 2017 / Revised: 22 November 2017 / Accepted: 7 December 2017 / Published: 12 December 2017
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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MDPI and ACS Style

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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