Synthesis of Gallic Acid Analogs as Histamine and Pro-Inflammatory Cytokine Inhibitors for Treatment of Mast Cell-Mediated Allergic Inflammation
- Authors
- Fei, Xiang; Je, In-Gyu; Shin, Tae-Yong; Kim, Sang-Hyun; Seo, Seung-Yong
- Issue Date
- Jun-2017
- Publisher
- MDPI AG
- Keywords
- gallic acid; allergic inflammation; histamine; pro-inflammatory cytokine
- Citation
- MOLECULES, v.22, no.6
- Journal Title
- MOLECULES
- Volume
- 22
- Number
- 6
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/6093
- DOI
- 10.3390/molecules22060898
- ISSN
- 1420-3049
- Abstract
- Gallic acid (3,4,5-trihydroxybenzoic acid), is a natural product found in various foods and herbs that are well known as powerful antioxidants. Our previous report demonstrated that it inhibits mast cell-derived inflammatory allergic reactions by blocking histamine release and pro-inflammatory cytokine expression. In this report, various amide analogs of gallic acid have been synthesized by introducing different amines through carbodiimide-mediated amide coupling and Pd/C-catalyzed hydrogenation. These compounds showed a modest to high inhibitory effect on histamine release and pro-inflammatory cytokine expression. Among them, the amide bearing (S)-phenylglycine methyl ester 3d was found to be more active than natural gallic acid. Further optimization yielded several (S)- and (R)-phenylglycine analogs that inhibited histamine release in vitro. Our findings suggest that some gallamides could be used as a treatment for allergic inflammatory diseases.
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