Cassane Diterpenoids from the Aerial Parts of Caesalpinia pulcherrima and Their Antifeedant and Insecticidal Activities against Mythimna separate and Plutella xylostella

Ten new cassane diterpenoids, caesalpulcherrins A–J (1–10), together with 11 known analogues (11–21) were isolated from the aerial parts of Caesalpinia pulcherrima. Their structures and relative stereochemistry were elucidated by spectrometric and spectroscopic methods, including one-dimensional (1D) and two-dimensional (2D) NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and single-crystal X-ray diffraction analysis. Compounds 1–4 represent the first examples of 2,5-dimethoxyfuranocassane diterpenoids. Results of the antifeedant activity indicated that isovouacapenol C (12) and pulcherrin N (14) exhibited remarkable antifeedant activity against Mythimna separate with EC₅₀ values of 3.43 and 4.20 μg/cm², respectively. Meanwhile, pulcherrimin C (13) and 12-demethyl neocaesalpin F (18) exerted significant antifeedant activity against Plutella xylostella with an EC₅₀ data of 4.00 and 3.05 μg/cm², respectively. Some of the compounds showed obvious toxic activity against the plant-feeding generalist insect herbivores, M. separate and P. xylostella, at 0.8 mg/mL (800 ppm). Furthermore, the structure–activity relationships of antifeedant and insecticidal activities are also discussed in the article.