Anti-Allergic Activity of Monoacylated Ascorbic Acid 2-Glucosides

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2017 Dec 13

PMID 29231858

Citations 3

Authors

Kaori Miura

Yuta Morishita

Hiroaki Matsuno

Yusuke Aota

Hideyuki Ito

Akihiro Tai

Affiliations

Soon will be listed here.

Abstract

2--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--acyl-2--α-d-glucopyranosyl-l-ascorbic acids having a straight-acyl chain of varying length from C₄ to C (6-sAcyl-AA-2G) and a branched-acyl chain of varying length from C₆ to C (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 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--α-d-Glucopyranosyl-6--hexadecanoyl-l-ascorbic acid (6-sPalm-AA-2G), which has a straight C 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.

Citing Articles

Antiallergic Activity of 3--Dodecyl-l-ascorbic Acid.

Koga T, Kawahara N, Aburada M, Ono A, Mae S, Yoshida A Molecules. 2024; 29(1).

PMID: 38202652 PMC: 10779884. DOI: 10.3390/molecules29010069.

Antiallergic Activity of 6-Deoxy-2--methyl-6-(-hexadecanoyl)amino-l-ascorbic Acid.

Miura K, Matsuno H, Iwaoka Y, Ito H, Tai A Molecules. 2021; 26(15).

PMID: 34361837 PMC: 8348947. DOI: 10.3390/molecules26154684.

Potential Antitumor Activity of 2-O-α-d-Glucopyranosyl-6-O-(2-Pentylheptanoyl)-l-Ascorbic Acid.

Miura K, Haraguchi M, Ito H, Tai A Int J Mol Sci. 2018; 19(2).

PMID: 29439410 PMC: 5855757. DOI: 10.3390/ijms19020535.

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