Department of Chemistry, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901 Belo Horizonte, MG, Brazil.
School of Chemical Technology, Faculty of Technology, Universidad Tecnológica de Pereira, Carrera 27 #10-02, Barrio Álamos, Código, 660003 Pereira, Risaralda, Colombia.
J Nat Prod. 2024 Sep 27;87(9):2272-2280. doi: 10.1021/acs.jnatprod.4c00714. Epub 2024 Sep 6.
Rubrolides are a family of naturally occurring 5-benzylidenebutenolides, which generally contain brominated phenol groups, and nearly half of them also present a chlorine attached to the butenolide core. Seven natural rubrolides were previously synthesized. When these compounds were tested against the model plant , six were found to exert a slight inhibition on plant growth. Aiming to exploit their scaffold as a model for the synthesis of new compounds targeting photosynthesis, nine new rubrolide analogues were prepared. The synthesis was accomplished in 2-4 steps with a 10-39% overall yield from 3,4-dichlorofuran-2(5)-one. All compounds were evaluated for their ability to inhibit the whole Hill reaction or excluding photosystem I (PSI). Several natural rubrolides and their analogues displayed good inhibitory potential (IC = 2-8 μM). Molecular docking studies on the photosystem II-light harvesting complex II (PSII-LHCII supercomplex) binding site were also performed. Overall, data support the use of rubrolides as a model for the development of new active principles targeting the photosynthetic electron transport chain to be used as herbicides.
红厚壳内酯是一组天然存在的 5-苄叉丁烯内酯，通常含有溴化酚基团，其中近一半还带有连接在丁烯内酯核心上的氯。此前已合成了七种天然红厚壳内酯。当这些化合物在模式植物上进行测试时，发现其中六种对植物生长有轻微的抑制作用。为了利用其支架作为合成针对光合作用的新化合物的模型，制备了九种新的红厚壳内酯类似物。合成分 2-4 步进行，从 3,4-二氯呋喃-2(5)-酮出发，总收率为 10-39%。所有化合物均评估了其抑制整个希尔反应或排除光系统 I（PSI）的能力。几种天然红厚壳内酯及其类似物显示出良好的抑制潜力（IC=2-8μM）。还对光系统 II-捕光复合物 II（PSII-LHCII 超复合物）结合位点进行了分子对接研究。总体而言，数据支持将红厚壳内酯用作针对光合作用电子传递链的新型有效成分的开发模型，以用作除草剂。
