Synthesis and Anti-inflammatory Evaluation of (R)-, (S)-, and (±)-Sanjuanolide Isolated from Dalea frutescens
Synthesis and Anti-inflammatory Evaluation of (R)-, (S)-, and (±)-Sanjuanolide Isolated from Dalea frutescens
复制标题
谷草 (R)-、(S)-、(/-)-三胡内酯的合成及抗炎评价
DOI：
10.1021/acs.jnatprod.8b00596
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发表时间：
2019-04-01
影响因子：
5.1
通讯作者：
Liu, Zhiguo
中科院分区：
文献类型：
--
作者：
Fang, Bo;Xiao, Zhongxiang;Liu, Zhiguo
The known chalcone (+/-)-sanjuanolide (1) can be isolated from Dalea frutescens. This study presents a convergent strategy for the first total synthesis of (R)-, (S)-, and (+/-)-sanjuanolide (1). The key step for synthesizing (R)- and (S)-1 was a Corey Bakshi Shibata enantioselective carbonyl reduction to construct the C-2 '' configuration. (R)-1 efficiently inhibited the lipopolysaccharides (LPS)-induced expression of tumor necrosis factor alpha (TNF-alpha) and interleukin-6 (IL-6), while (S)-1 produced no significant anti-inflammatory effect. (R)-1 also effectively inhibited the mRNA expression of several inflammatory cytokines after the LPS challenge in vitro. The synthesis and biological properties of these compounds have confirmed (R)-sanjuanolide and (+/-)-sanjuanolide as promising new leads for developing anti-inflammatory agents.
