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Molecules 2016, 21(10), 1416; doi:10.3390/molecules21101416

Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production

1
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China
2
College of Forestry, Northwest A&F University, Yangling 712100, Shaanxi, China
3
College of Pharmacy, Chungnam National University, Daejeon 305-764, Korea
*
Authors to whom correspondence should be addressed.
Academic Editor: Isabel C. F. R. Ferreira
Received: 18 September 2016 / Revised: 8 October 2016 / Accepted: 10 October 2016 / Published: 23 October 2016
(This article belongs to the Collection Bioactive Compounds)
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Abstract

Four new unsaturated aliphatic acid amides, named zanthoamides A–D (14), 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 (2E,7E,9E)-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 IC50values 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 (IC50 > 60 μM). They could contribute to the anti-inflammatory effects of Z. bungeanum by suppression of NO production. View Full-Text
Keywords: Huajiao; Zanthoxylum bungeanum; unsaturated alkylamides; isobutylhydroxyamides; sanshools; NO inhibitory activity; anti-inflammatory Huajiao; Zanthoxylum bungeanum; unsaturated alkylamides; isobutylhydroxyamides; sanshools; NO inhibitory activity; anti-inflammatory
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Wang, Y.; Li, C.-H.; Luo, B.; Sun, Y.N.; Kim, Y.H.; Wei, A.-Z.; Gao, J.-M. Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production. Molecules 2016, 21, 1416.

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