Precursor-Directed Biosynthesis of Aminofulvenes: New Chalanilines from Endophytic Fungus Chalara sp.
Precursor-Directed Biosynthesis of Aminofulvenes: New Chalanilines from Endophytic Fungus Chalara sp.
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DOI：
10.3390/molecules26154418
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发表时间：
2021-07-22
期刊：
影响因子：
--
通讯作者：
Loesgen S
中科院分区：
文献类型：
--
作者：
Khoshbakht M;Srey J;Adpressa DA;Jagels A;Loesgen S
植物内生菌 Chalara sp.能够对表观遗传修饰剂伏立诺他进行生物转化，形成独特的含苯胺聚酮化合物，名为 chalanilines。在这里，我们试图通过改变前体伏立诺他中的苯胺部分来扩大 chalaniline A 型分子的化学多样性。总共，通过两步合成制备了二十三种不同的伏立诺他类似物，其中十九种被真菌掺入聚酮化合物中。选择最高产率的底物进行大规模前体定向生物合成，并分离、纯化和结构表征了五种新化合物，包括两种氟化查兰苯胺。结构解析依赖于一维和二维核磁共振技术，并得到低分辨率和高分辨率质谱的支持。所有化合物都经过了生物活性测试，但在抗菌或细胞活力测定中没有活性。含氨基富烯的天然产物很少见，这种高产率、前体导向的工艺可以实现此类化合物的多样化。
The plant endophyte Chalara sp. is able to biotransform the epigenetic modifier vorinostat to form unique, aniline-containing polyketides named chalanilines. Here, we sought to expand the chemical diversity of chalaniline A-type molecules by changing the aniline moiety in the precursor vorinostat. In total, twenty-three different vorinostat analogs were prepared via two-step synthesis, and nineteen were incorporated by the fungus into polyketides. The highest yielding substrates were selected for large-scale precursor-directed biosynthesis and five novel compounds, including two fluorinated chalanilines, were isolated, purified, and structurally characterized. Structure elucidation relied on 1D and 2D NMR techniques and was supported by low- and high-resolution mass spectrometry. All compounds were tested for their bioactivity but were not active in antimicrobial or cell viability assays. Aminofulvene-containing natural products are rare, and this high-yielding, precursor-directed process allows for the diversification of this class of compounds.
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