Study On The Zanthoxylum Bungranum And The Biological Activities

Zanthoxylum bungeanum Maxim.has been used for more than two thousand years,selected as the Chinese medicinal and edible plant.However,there are few studies on the components of Z.bungeanu.In this paper,we studied the chemical consitituents of Fengxian,Hancheng and Linxia pepper and their multiple biological activities.By using repeated chromatographic column on silica gel,Sephadex LH-20,revesedphase C18,PTLC and HPLC,41 compounds,including 15 new compounds were obtained from the pericarps of the Fengjiao and Linxiajiao.The structures were elucidated on the basis of spectroscopic analysis:¹H-NMR,¹³C-NMR,HSQC,¹H-¹H COSY,HMBC and（HR-ESI）MS.Also,the biological activities of most compounds from Z.bungeanum were tested.The results are concluded as follows:1.15 new compounds were isolated and elucidated from the pericarp of Z.bungeanum Maxim:（2E,4E,9E,11E）-N-（2-hydroxy-2-methypropyl）-8-hydroxy-13-oxo-2,4,9,11–tetradecatetraenamide（1）,（2E,4E,9E,11E）-N-（hydroxy-2-methypropyl）-8,13-dihydroxy-2,4,9,11-tetradecatetraenamide（2）,（10*,11*）-（2E,6E,8E）-10,11-dihydroxy-N-（2-hydroxy-2-methylpropyl）-2,6,8-dodecatrienamide（3）,2E-6-dihymethoxy-N-（2-hydroxy-2-methylpropyl）-2-hexameamide（4）,（2E,7E,9E）-6-ethoxy-11-hydroxy-N-（2-hy-droxy-2-methylpropyl）-dodeca-2,7,9-tetradecatriae-namide（13）,（2E,7E,9E）-11-ethoxy-6-hydroxy-N-（2-hydroxy-2-methylpropyl）-dodeca-2,7,9-tetradecatriaenamide（14）,（2E,6E,8E）-10-hydroxy-N-（2-hydroxy-2-methylpr-opyl）-5-oxoundeca-2,6,8-tetradecatriaenamide（15）,（12RS,13SR）-（2E,4E,8E,10E）-N-（2-hydroxy-2-methypropyl）-12,13-dihydroxy-2,4,8,10-tetradecatetraenamide（16）,（12RS,13RS）-（2E,4E,8Z,10E）-N-（hydroxy-2-methypropyl）-12,13-dihydroxy-2,4,8,10-tetradec-atetraenamide（17）,（2E,8E,11E）-N-（hydroxy-2-methypropyl）-2,8,11-tridecatetraenamide（3-2）,（2E,8Z,11E）-N-（hydroxy-2-methypropyl）-2,8,11-tridecatetraenamide（3-3）,（2E）-N-（2-hydroxy-2-methypropyl）-2-decatetraenamide（3-4）,（2Z,6E）-1,5-dimethyl-6-hydroxy-2,6-heptadien-1-ol,1-acetate（3-5）,（2E,4E,7E,11Z）-N-（2-hydroxy-2-methypropyl）-2,4,7,11-tetradecatetraenamide（3-10）,（2E,7E,9E）-N-（2-hydroxyl-2-methylpropyl）-6,11-dimethoxy-2,7,9-dodecatrienamide（3-11）。2.26 known compounds were isolated and elucidated from Z.bungeanum Maxim: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）,（2E,7E,9E）-N-（2-hydroxy-2-methylpropyl）-6,11-dioxo-2,7,9-dodecatrien-amide（12）,ZP-amide A（2-1）,ZP-amide B（2-2）,ZP-amide C（2-3）,ZP-amide D（2-4）,ZP-amide E（2-5）,（2E,4E,8E,11Z）-2’-hydroxy-N-isobutyl-2,4,8,11-tetradecatetraenamide（2-6）,ZP-amide A（2-7）,ZP-amide B（2-8）,ZP-amide E（2-9）,ZP-amide C（2-10）,ZP-amide D（2-11）,（2E,4E,8Z,11Z）-2’-Hydroxy-N-isobutyl-2,4,8,11-tetradecatetraenamide（3-1）,4-hydroxybenzoic acid methylester（3-6）,tetrahydrobungeanool（3-7）,2,4-dimethoxybenzeneacetamide（3-8）,hydroxyl-β-sanschool（3-9）,hydroxyl-γ-sanschool（3-12）and hydroxyl-γ-isosanschool（3-13）。3.Bioassays exhibited significant inhibitory effects of comupound 1¹2isobutylhydroxyamides on nitric oxide（NO）productionat concentrations of 20?M by decreasing the nitrite accumulation in LPS-stimulated RAW 264.7 macrophages.They could contribute to the anti-inflammatory effects of Z.bungeanum by suppression of NO production.Then tested compounds enhanced nerve growth factor（NGF）-mediated neurite outgrowth（neurotrophic activity）in rat pheochromocytoma（PC12）cells.All the known compounds were inactive in toxicity against brineshri and in phytotoxic effects on radish seedlings.Besides,there were no antioxidant activity and no cytotoxic activity of all the compounds.Sensory studies by means of a modified half-tongue test revealed recognition thresholds ranging from 0.94 to 2.14×10^-5g/mL,with numbing orosensation depending on their chemical structure.