ZP-amide C

Molecules . 2016 Oct 23;21(10):1416.

Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production[Pubmed: 27782100]

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.

Bioorg Med Chem Lett . 2016 Jan 15;26(2):338-342.

Characterization of isobutylhydroxyamides with NGF-potentiating activity from Zanthoxylum bungeanum[Pubmed: 26707398]

Eight isobutylhydroxyamides, including three new (1-3), qinbunamides A-C, and five known sanshools (4-8), ZP-amide A (4), ZP-amide B (5), ZP-amide E (6), ZP-amide C (7), and ZP-amide D (8), were isolated from the pericarps of cultivated Zanthoxylum bungeanum Maxim, cultivated in Qinling mountain area, Shaanxi, China. The structures of all compounds were determined on the basis of spectroscopic techniques, including 1D and 2D NMR analysis and comparison with previously reported data. Compounds 1 and 2 are the first example of isobutylhydroxyamides containing an ethoxy group, and compound 3 is a rare C11 fatty acid-containing sanshool existing in genus Zanthoxylum. The tested compounds enhanced nerve growth factor (NGF)-mediated neurite outgrowth (neurotrophic activity) in rat pheochromocytoma (PC12) cells, but were inactive in the inhibitory effects on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and growth of HCT116 cells at concentrations of 50μM.