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
▼
Show Figures
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
- Supplementary File 1:
PDF-Document (PDF, 1135 KiB)
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. https://doi.org/10.3390/molecules22122202
AMA 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(12):2202. https://doi.org/10.3390/molecules22122202
Chicago/Turabian StyleMiura, Kaori; Morishita, Yuta; Matsuno, Hiroaki; Aota, Yusuke; Ito, Hideyuki; Tai, Akihiro. 2017. "Anti-Allergic Activity of Monoacylated Ascorbic Acid 2-Glucosides" Molecules 22, no. 12: 2202. https://doi.org/10.3390/molecules22122202
Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.
Search more from Scilit