Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (CSIC), Avda. Astrofísico F. Sánchez 3, 38206 La Laguna, Tenerife, Spain.
Departamento de Química, Universidad de Antofagasta, Antofagasta 124000, Chile.
Molecules. 2023 Jan 18;28(3):975. doi: 10.3390/molecules28030975.
In this work, we have studied the benzofurans of (aerial parts and transformed roots), (aerial parts and transformed roots), (aerial parts), and (aerial parts and roots). This work has permitted the isolation of the new benzofurans 10-ethoxy-11-hydroxy-10,11-dihydroeuparin (), (-)-eupachinin A ethyl ether (), 11,15-didehydro-eupachinin A (), 10,12-dihydroxy-11-angelyloxy-10,11-dihydroeuparin (), 2,4-dihydroxy-5-formyl-acetophenone () isolated for the first time as a natural product, 11-angelyloxy-10,11-dihydroeuparin (), and 12-angelyloxyeuparone (), along with several known ones (-). In addition, the incubation of the abundant component, 6-hydroxytremetone (), with the fungus has been studied. Benzofurans in the tremetone series (, , -, , ), the euparin series (, , , -, , ), and the eupachinin-type (, ) were tested for antifeedant effects against the insect . The antifeedant compounds (, , , , ) were further tested for postingestive effects on larvae. The most antifeedant compounds were among the tremetone series, with 3-ethoxy-hydroxy-tremetone () being the strongest antifeedant. Glucosylation of by its biotransformation with gave inactive products. Among the euparin series, the dihydroxyangelate was the most active, followed by euparin (). The eupachinin-type compounds (, ) were both antifeedants. Compounds and showed antifeedant effects without postingestive toxicity to orally dosed larvae. Euparin ( had postingestive toxicity that was enhanced by the synergist piperonyl butoxide.
在这项工作中，我们研究了 (地上部分和转化根)、 (地上部分和转化根)、 (地上部分)和 (地上部分和根)中的苯并呋喃。这项工作允许分离出新型苯并呋喃 10-乙氧基-11-羟基-10,11-二氢 euparin ()、(-)-eupachinin A 乙基醚 ()、11,15-二脱氢 eupachinin A ()、10,12-二羟基-11-angeloyloxy-10,11-二氢 euparin ()、2,4-二羟基-5-甲酰基-苯乙酮 ()，它们是首次作为天然产物分离出来的，11-angeloyloxy-10,11-二氢 euparin ()和 12-angeloyloxyeuparone ()，以及几个已知的 (-)。此外，还研究了丰富的成分 6-羟基三瑞香素 ()与真菌 共孵育的情况。苯并呋喃在 tremetone 系列（、、-、-、）、euparin 系列（、、、-、）和 eupachinin 型（、）中测试了对昆虫 的拒食作用。拒食化合物（、、、、）进一步测试了对 幼虫的摄食后作用。最具拒食作用的化合物属于 tremetone 系列，其中 3-乙氧基-羟基-三瑞香素 ()是最强的拒食化合物。通过与 共生物转化进行葡萄糖苷化得到无活性产物。在 euparin 系列中，二羟基 angelate 是最活跃的，其次是 euparin ()。eupachinin 型化合物（、）都是拒食剂。化合物 和 都表现出拒食作用，而对口服给予的 幼虫没有摄食后毒性。Euparin ()具有摄食后毒性，增效剂胡椒基丁醚可增强其毒性。
