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

作者：Chun‐Huan Li, Jiayao Zhang, Thi Mai Luong Tuong, Yao Liu, Xuan Nien Hoang, Jin‐Ming Gao · 发表于：Journal of Agricultural and Food Chemistry · 年份：2020 · DOI：10.1021/acs.jafc.0c00853 · 被引用次数：23 · 研究领域：Biological Stains and Phytochemicals、Bioactive Natural Diterpenoids Research

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 EC 50 values of 3.43 and 4.20 μg/cm 2, respectively. Meanwhile, pulcherrimin C ( 13 ) and 12-demethyl neocaesalpin F ( 18 ) exerted significant antifeedant activity against Plutella xylostella with an EC 50 data of 4.00 and 3.05 μg/cm 2, 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.