Cassane Diterpenoids from the Aerial Parts of and Their Antifeedant and Insecticidal Activities against and .

J Agric Food Chem

Shaanxi Key Laboratory of Natural Products & Chemical Biology, Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, People's Republic of China.

Published: April 2020

Ten new cassane diterpenoids, caesalpulcherrins A-J (-), together with 11 known analogues (-) were isolated from the aerial parts of . 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 - represent the first examples of 2,5-dimethoxyfuranocassane diterpenoids. Results of the antifeedant activity indicated that isovouacapenol C () and pulcherrin N () exhibited remarkable antifeedant activity against with EC values of 3.43 and 4.20 μg/cm, respectively. Meanwhile, pulcherrimin C () and 12-demethyl neocaesalpin F () exerted significant antifeedant activity against with an EC data of 4.00 and 3.05 μg/cm, respectively. Some of the compounds showed obvious toxic activity against the plant-feeding generalist insect herbivores, and , at 0.8 mg/mL (800 ppm). Furthermore, the structure-activity relationships of antifeedant and insecticidal activities are also discussed in the article.

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http://dx.doi.org/10.1021/acs.jafc.0c00853DOI Listing

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