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. 2016 Oct 23;21(10):1416.
doi: 10.3390/molecules21101416.

Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production

Yuan Wang  1   2 , Chun-Huan Li  3 , Bo Luo  4 , Ya Nan Sun  5 , Young Ho Kim  6 , An-Zhi Wei  7 , Jin-Ming Gao  8
Affiliations

Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production

Yuan Wang et al. Molecules. .

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 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.

Keywords: Huajiao; NO inhibitory activity; Zanthoxylum bungeanum; anti-inflammatory; isobutylhydroxyamides; sanshools; unsaturated alkylamides.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of compounds 1–12.
Figure 2
Figure 2
Selected 2D NMR correlations for compounds 1–4.
See this image and copyright information in PMC

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