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As <jats:italic>S. frugiperda<\/jats:italic> has developed widespread resistance, environmentally friendly insecticides are urgently needed. Therefore, searching for natural antifeedant or insecticidal lead compounds has become imperative.<\/jats:p><\/jats:sec><jats:sec><jats:title>RESULTS<\/jats:title><jats:p>Three new indole diterpenoids, paspamine A (1), paspamine B (2), and paspalitrem D (3), along with nine known ones (compounds 4\u201312), were isolated from an endophytic <jats:italic>Penicillium brefeldianum<\/jats:italic> F4a. Their structures were identified through comprehensive spectroscopic data analysis [one\u2010dimensional (1D) and two\u2010dimensional (2D) nuclear magnetic resonance (NMR), high\u2010resolution electrospray ionization mass spectrometry (HR\u2010ESI\u2010MS), ultraviolet (UV), infrared (IR)], and electronic circular dichroism (ECD) calculations. Furthermore, plausible biosynthetic pathways of these compounds were deduced. The bioassay results indicated that compound 8 displayed more significant antifeedant activity against <jats:italic>S. frugiperda<\/jats:italic> larvae than azadirachtin and compounds 5\u20137 demonstrated superior insecticidal activities compared to abamectin. Moreover, comparative transcriptome analysis revealed that compound 6 exerted a distinct insecticidal mechanism. In the early stages, it regulated the expression of genes associated with peptidases and chitinases. Subsequently, this regulation influenced the expression of genes related to cuticle proteins and other relevant genes, ultimately resulting in <jats:italic>S<\/jats:italic>. <jats:italic>frugiperda<\/jats:italic> larval death. These results were further confirmed by real\u2010time quantitative polymerase chain reaction (RT\u2010qPCR) experiments.<\/jats:p><\/jats:sec><jats:sec><jats:title>CONCLUSION<\/jats:title><jats:p>This research will provide valuable information for the development of indole diterpenoids as novel microbial insecticides for the management of <jats:italic>S. frugiperda<\/jats:italic>. \u00a9 2025 Society of Chemical Industry.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ps.8842","type":"journal-article","created":{"date-parts":[[2025,4,21]],"date-time":"2025-04-21T06:01:11Z","timestamp":1745215271000},"page":"4788-4798","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Indole\u2010diterpenoids from an endophytic <scp><i>Penicillium brefeldianum<\/i><\/scp> F4a and their antifeedant and insecticidal activities against <scp><i>Spodoptera frugiperda<\/i><\/scp>"],"prefix":"10.1002","volume":"81","author":[{"given":"Yan","family":"Bai","sequence":"first","affiliation":[{"name":"CAS Key Laboratory of Forest Ecology and Silviculture Institute of Applied Ecology, Chinese Academy of Sciences  Shenyang China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fengting","family":"Kong","sequence":"additional","affiliation":[{"name":"CAS Key Laboratory of Forest Ecology and Silviculture Institute of Applied Ecology, Chinese Academy of Sciences  Shenyang China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoyu","family":"Song","sequence":"additional","affiliation":[{"name":"CAS Key Laboratory of Forest Ecology and Silviculture Institute of Applied Ecology, Chinese Academy of Sciences  Shenyang China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yafei","family":"Han","sequence":"additional","affiliation":[{"name":"CAS Key Laboratory of Forest Ecology and Silviculture Institute 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