title: Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production.
abstract: 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 (2E,7E,9E)-N-(2-hydroxy-2-methylpropyl)-6,11-dioxo-2,7,9-dodecatrienamide (12)-were isolated from the pericarps ofZanthoxylum 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. Compound4contained a rare C₆ fatty acid unit with an acetal group. Results revealed that compounds1,5,6, and12showed 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 ofZ. bungeanumby suppression of NO production.
authors: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. angsoneaven@163.com.|College of Forestry, Northwest A&F University, Yangling 712100, Shaanxi, China. angsoneaven@163.com.
authors: Yuan
authors: Y
authors: Wang
authors: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. chunhuanli@nwsuaf.edu.cn.
authors: Chun-Huan
authors: CH
authors: Li
authors: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. luobo2011@163.com.
authors: Bo
authors: B
authors: Luo
authors: College of Pharmacy, Chungnam National University, Daejeon 305-764, Korea. yanansun@163.com.
authors: Ya Nan
authors: YN
authors: Sun
authors: College of Pharmacy, Chungnam National University, Daejeon 305-764, Korea. yhk@cnu.ac.kr.
authors: Young Ho
authors: YH
authors: Kim
authors: College of Forestry, Northwest A&F University, Yangling 712100, Shaanxi, China. anzhiwei@nwsuaf.edu.cn.
authors: An-Zhi
authors: AZ
authors: Wei
authors: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. jinminggao@nwsuaf.edu.cn.
authors: Jin-Ming
authors: JM
authors: Gao
mesh_terms: D000577:Amides / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000494:pharmacology; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D000067996:RAW 264.7 Cells / Q000187:drug effects; D032106:Zanthoxylum / Q000737:chemistry*
chemical_list: D000577:Amides; D000893:Anti-Inflammatory Agents; D005231:Fatty Acids, Unsaturated; D008070:Lipopolysaccharides; D010936:Plant Extracts; D009569:Nitric Oxide
keywords: Huajiao; NO inhibitory activity; Zanthoxylum bungeanum; anti-inflammatory; isobutylhydroxyamides; sanshools; unsaturated alkylamides