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Four new unsaturated aliphatic acid amides, named zanthoamides A-D ( 1 - 4 ), and eight known ones-tetrahydrobungeanool ( 5 ), ZP-amide A ( 6 ), ZP-amide B ( 7 ), ZP-amide C ( 8 ), ZP-amide D ( 9 ), ZP-amide E ( 10 ), bugeanumamide A ( 11 ), and (2 E ,7 E ,9 E )- N -(2-hydroxy-2-methylpropyl)-6,11-dioxo-2,7,9-dodecatrienamide ( 12 )-were isolated from the pericarps of Zanthoxylum bungeanum . The structures of these compounds were elucidated by extensive use of spectroscopic methods, including HRESIMS, 1D and 2D NMR analyses and comparison with previously reported data. Compound 4 contained a rare C₆ fatty acid unit with an acetal group. Results revealed that compounds 1 , 5 , 6 , and 12 showed inhibitory effects on nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages, with IC 50 values of 48.7 ± 0.32, 27.1 ± 1.15, 49.8 ± 0.38, and 39.4 ± 0.63 µM, respectively, while the other compounds were inactive (IC 50 &gt; 60 μM). They could contribute to the anti-inflammatory effects of Z. bungeanum by suppression of NO production.

Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production