Total synthesis, absolute configuration, and phytotoxic activity of foeniculoxin
Total synthesis, absolute configuration, and phytotoxic activity of foeniculoxin
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茴香碱的全合成、绝对构型及药害活性
DOI：
10.1002/chem.202203396
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发表时间：
2023
影响因子：
4.3
通讯作者：
Toyonobu Usuki
中科院分区：
文献类型：
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作者：
Akane Yamagishi;Yuki Egoshi;Makoto T. Fujiwara;Noriyuki Suzuki;Tohru Taniguchi;Ryuuichi D. Itoh;Yumiko Suzuki;Yoshiro Masuyama;Kenji Monde;Toyonobu Usuki
茴香毒素是茴香拟茎点霉（Phomopsis foeniculi）意大利菌株产生的一种主要植物毒素。首次全合成利用烯反应和Sonogashira交叉偶联反应作为关键步骤进行描述。采用手性拆分和改进的Mosher方法确定了C6'的绝对构型。通过基于注射器的渗透到白藜（Chenopodium albumandArabidopsis thalianaleae）中证明了合成化合物的植物毒性。在损伤形成之前，合成的foeniculoxin诱导拟南芥叶细胞中的各种缺陷，包括蛋白质从叶绿体和线粒体渗漏到细胞质中以及线粒体变圆和肿胀。此外，foeniculoxin和抗生素潮霉素B引起类似的线粒体聚集在叶绿体周围，突出了这一事件作为植物细胞死亡早期阶段的共同组成部分。
Foeniculoxin is a major phytotoxin produced by Italian strains ofPhomopsis foeniculi. The first total synthesis is described utilizing the ene reaction and Sonogashira cross‐coupling reaction as key steps. The absolute configuration of the C6’ was determined using chiral separation and an advanced Mosher's method. The phytotoxicity of the synthesized compound was demonstrated via syringe‐based infiltration intoChenopodium albumandArabidopsis thalianaleaves. Synthetic foeniculoxin induced various defects inA. thalianaleaf cells before lesion formation, including protein leakage into the cytoplasm from both chloroplasts and mitochondria and mitochondrial rounding and swelling. Furthermore, foeniculoxin and the antibiotic hygromycin B caused similar agglomeration of mitochondria around chloroplasts, highlighting this event as a common component in the early stages of plant cell death.