Studies On The Constituents Fromzanthoxylum Bungeanum Maxim. And Their Biological Activities

Traditional Chinese medicine is a treasure of Chinese culture.In recent years,edible Chinese herbal has become a new bright spot in the development of TCM health industry due to its wide application.Edible Chinese herbal contains a variety of natural products with unique structures.In the long-term practice,edible Chinese herbal has been proved to have significant curative effect with less toxic and side effects,which make the development of the natural product in edible Chinese herbal to be a new source of the potential drug compounds.Z.bungeanum Maxim.,a small deciduous tree belonging to the family Rutaceae,is widely distributed in China with high edible and medicinal value.It is a well known spice as well as a commonly used TCM with spleen and stomach warming medical function.Modern pharmacological studies demonstrated that it possessed a series of beneficial biological activities such as anti-inflammatory,anti-tumor,reducing blood pressure and blood fat properties.Phytochemical investigation was carried on this edible traditional Chinese medicine.Most of the isolated compounds were evaluated for cytotoxic and NO inhibitory activities as well as protective effect on PC 12 cells damaged by corticosterone.90 compounds were isolated from the 95%EtOH extracts of Zanthoxylum bungeanum Maxim with chromatographic methods such as D101 macroporous resin,silica gel,ODS and Sephadex LH-20 column chromatography as well as preparative HPLC.The planar structures were determined on the basis of the spectroscopic and physicochemical data.The absolute configurations of the chiral centers in the optical active compounds were established by electronic circular dichroism calculation and modified Mosher’s method.90 compounds(12 pairs of compounds are racemic mixtures)isolated from the 95%ethanol extract of the Z.bungeanum Maxim including 54 isobutylhydroxyamides(12 pairs of compounds are racemic mixture),6 flavonoids,4 monoterpene,15 phenolic acids,6 alkaloids and the others.Compounds A1-A14 and A43 are new compounds that haven’t been reported,named ZP-amide G-T(Ala-A14)and ZP-terpenoside A(A43).Known compounds were identified as ZP-amide4a(A15),zanthoamide(A16),ZP-amide-C(A17),ZP-amide-D(A18),syn-ZP-amide-E(A19),anti-ZP-amide-E(A20),hydroxy-α-sanshool(A21),bungeanool(A22),(-)-(6R)-ZP-amide A(A23),(+)-(6S)-ZP-amide A(A24),(-)-(11R)-ZP-amide B(A25),(+)-(11S)-ZP-amide B(A26),isobungeanool(A27),(2E,7E,9E)-N-(2-hydroxy-2-methylpropyl)-6,11-dioxo-2,7,9dodecatrienamide(A28),(2E,6E,8E)-N-(2-hydroxy-2-methylpropyl)-10-oxo-2,6,8decatrienamide(A29),qinbunamide A(A30),qinbunamide A(A31),qinbunamide B(A32),zanthoamide D(A33),timuramide C(A34),bungeanumamide B1(A35),bungeanumamide B2(A36),bungeanumamide A1(A37),bungeanumamide A2(A38),ZP-amide F1(A39),ZPamide F2(A40),ZP-amide F3(A41),ZP-amide F4(A42),4-hydroxycryptone(A44),piperitone(A45),(2E,4E)-6-hydroxy-2,6-dimethylhepta-2.4-dienal(A46),N14formyldihydrorutaecarpine(A47),rutaecarpine(A48),tetrahydroberberine(A49),1,2,3,4tetrahydro-β-carboline-3-carboxylic acid(A50),anoectochine(A51),inosine(A52),4’7dimethoxy-5-hydroxyflavone(A53),salvigenin(A54),genkwanin(A55),isorhamnetin-7glucoside(A56),hyperoside(A57),tamarixetin-3,7-di-O-β-D-glucopyranoside(A58),vanillic acid(A59),isovanillic acid(A60),4-methoxybenzoic acid(A61),trans-p-coumaric acid(A62),p-hydroxybenzoic acid(A63),p-hydroxyphenylpropionie acid(A64),lariside F2(A65),2phenethyl-O-β-D-glucopyranoside(A66),benzyl-O-β-D-glucopyranoside(A67),arbutin(A68),1-O-β-D-glucopyranosyloxy-3-methoxy-5-hydroxybenzene(A69),3’methoxyphenylenthanol-4’-O-β-D-glucopynanoside(A70),orcinol-3-O-β-D-glucopyranoside(A71),2-phenethylrutinoside(A72),syringin(A73),1’-(2-hydroxybutyl)-3-methoxyphenyl-Oβ-D-glucopyranoside(A74),breyniaionosiade A(A75),marmesin(A76),lyoniresinol-3a-O-βD-glucopyranoside(A77),2-methylpropanyl-6-O-β-D-apiofuranosyl-β-D-glucopyranoside(A78).Isobutylhydroxyamides from Z bungeanum Maxim.were evaluated for their protective effect on PC12 cells damaged by corticosterone.Compounds Ala-A3,A16,A23,A25 and A28 at concentration of 3.125 μM to 100 uM exhibited protective effect.Compound A13 showed moderate cytotoxic activity on HepG2 cell line with IC50 value of 68.4±5.77 μmol/L.