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Nitric Oxide Inhibitory Activity and Absolute Configurations of Arylalkenyl α,β-Unsaturated δ/γ-Lactones from Cryptocarya concinna

Yang, Bing-Yuan, Kong, Ling-Yi, Wang, Xiao-Bing, Zhang, Yang-Mei, Li, Rui-Jun, Yang, Ming-Hua, Luo, Jian-Guang
Journal of natural products 2016 v.79 no.1 pp. 196-203
Cryptocarya concinna, anti-inflammatory activity, anti-inflammatory agents, branches, chemical structure, derivatization, inhibitory concentration 50, lactones, leaves, macrophages, mass spectrometry, medicinal plants, nitric oxide, nuclear magnetic resonance spectroscopy, spectral analysis, stereoisomerism
During an ongoing exploration of potential anti-inflammatory agents from medicinal plants, eight new arylalkenyl α,β-unsaturated δ-lactones, cryptoconcatones A–H (1–8), and two unusual arylalkenyl α,β-unsaturated γ-lactones, cryptoconcatones I and J (9 and 10), were identified from the leaves and twigs of Cryptocarya concinna. The structures of these compounds were established based on spectroscopic data (MS, 1D/2D NMR), and their absolute configurations were determined with Riguera’s method, the modified Mosher’s method, chemical derivatization, and the Snatzke chirality rule. Compounds 4–6 and 8–10 showed inhibitory activity toward nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages, particularly compounds 4 and 8–10, with IC₅₀ values of 3.2, 4.2, 3.4, and 7.5 μM, respectively.