The first synthesis and immunomodulatory properties of p-hydroxyphenyl caffeate derived from Wedelia trilobata
Journal of Asian Natural Products Research(2020)
Abstract
Herein, we report a concise and efficient method for the synthesis of p-hydroxyphenyl caffeate, a novel natural caffeic acid ester derivative isolated from Wedelia trilobata. The key feature of this synthesis is the Verley–Doebner modification of the Knoevenagel condensation of the p-hydroxyphenyl malonate intermediate. The synthesized p-hydroxyphenyl caffeate enhanced interleukin 2 production by murine lymph node T cells, and suppressed interleukin 13 production by murine epidermal T cells. This implies that p-hydroxyphenyl caffeate might be a novel immunomodulatory drug candidate, specifically targeting T helper 2 cell type responses in skin diseases such as atopic dermatitis and vitiligo.
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Key words
p-Hydroxyphenyl caffeate,Verley–Doebner modification,Knoevenagel condensation,epidermal T cell,interleukin 13
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