Synthesis and structure?activity relationship of violaceoid D, a cytotoxic alkylated phenol isolated from <i>Aspergillus violaceofuscus</i> Gasperini
Synthesis and structure?activity relationship of violaceoid D, a cytotoxic alkylated phenol isolated from <i>Aspergillus violaceofuscus</i> Gasperini
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从 <i>Aspergillus violaceofuscus</i> Gasperini 中分离出的细胞毒性烷基化酚 violaceoid D 的合成及其构效关系
DOI：
10.1093/bbb/zbac212
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Yajima Arata
中科院分区：
文献类型：
--
作者：
Shoji Atsushi;Arai Yuka;Asakawa Ryuki;Saito Tatsuo;Kuramochi Kouji;Yajima Arata
实现了从紫曲霉培养液中分离出的细胞毒性酚类化合物 violaceoid D 的对映选择性合成。全合成涉及通过 Sharpless 不对称二羟基化立体选择性构建紫罗兰苷 D 的立体中心，然后进行 Smiles 重排。天然紫罗兰醇D的绝对构型由比旋光度值确定。评估了合成的紫罗兰素 D 及其类似物对两种人类癌细胞系 Jurkat 和 HCT116 的细胞毒性。由于紫罗兰醇 D 的对映体没有表现出细胞毒性，因此紫罗兰醇 D 可能选择性地与特定靶分子（例如癌细胞中的蛋白质）结合。
The enantioselective synthesis of violaceoid D, a cytotoxic phenolic compound isolated from the culture broth ofAspergillus violaceofuscusGasperini, was achieved. The total synthesis involves stereoselective construction of the stereogenic center of violaceoid D via Sharpless asymmetric dihydroxylation, followed by Smiles rearrangement. The absolute configuration of natural violaceoid D was determined to beRfrom the specific rotation value. Synthesized violaceoid D and its analogs were evaluated for cytotoxicity against two human cancer cell lines, Jurkat and HCT116. Because the enantiomer of violaceoid D showed no cytotoxicity, it is plausible that violaceoid D binds selectively to specific target molecules, such as proteins in the cancer cells.