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  • The first synthesis and immunomodulatory properties of p-hydroxyphenyl caffeate derived from Wedelia trilobata.

The first synthesis and immunomodulatory properties of p-hydroxyphenyl caffeate derived from Wedelia trilobata.

Journal of Asian natural products research (2020-08-22)
Jisu Yang, Jeong A Yoon, Kwangmi Kim, Young Taek Han
摘要

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. [Formula: see text].

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Sigma-Aldrich
甲醇-d1, 98 atom % D