Studies On The Active Constituents And Quality Of Euodia Rutaecarpa Benth.

Euodiae Fructus,the fruits of Euodia rutaecarpa(Juss.)Benth.or Euodia rutaecarpa(Juss.)Benth.var.offcinalis(Dode)Huang or Euodia rutaecarpa(Juss.)Benth.var.bodinieri(Dode)Huang as a traditional Chinese medicine,the plants are distributed mainly in south of the Yangtze river basin in China.E.rutaecarpa has been used as a traditional Chinese drug with a long history in traditional clinic treatments.It is also the main content in many Chinese medicinal formula,such as HUA-TUO-ZAI-ZAO pill,WU-ZHU-YU soup,ZUO-JIN pill.In order to elucidate its material basis and find much more active substance,specially to provide a reasonable and scientific basis for quality control,the further chemical investigation of the Eudiae Fructus was carried out.Moreover the fingerprint was established by HPLC-DAD/ESI-MSn technology,which could provide a valid and reliable method to control the quality.The alkaloids were screened antibacterial,cytotoxicity and anti-inflammatory activities.The main results are as follow:1.By means of many modern chemical isolation and identifiacation technology 66 compounds were isolated and identified from the fruits of E.rutaecarpa,including thirtythree alkaloids,they were 2-ethyl-N-methy1-4(1H)-quinolone(1),N-methyl-2-pentyl-4-(1 H)-quinolone(2),N-methyl-2-hepty1-4(1H)-quinolone(3),N-methyl-2-octyl-4(1 H)-quinolone(4),N-methyl-2-nony1-4(1H)-quinolone(5),N-methyl-2-decyl-4(1H)-quinolone(6),N-methyl-2-undecy1-1-4(1H)-quinolone(7),AN-methy l-2-dodecyl-4-(1 H)-quinolone(8),N-methyl-2-tridecyl-4(1H)-quinolone(9),N-methyl-2-tetradecyl-4-(1 H)-quinolone(10),N-methyl-2-pentadecenyl-4(1 H)-quinolone(11),N-methyl-2-[(Z)-5'-dodecenyl]-4(1H)-quinolone(12),evocarpine(13),N-methyl-2-[(Z)-5'-pentadecenyl]-4(1H)-quinolone(14),N-methyl-2-[(6'Z,9'Z)-6',9'-pentadecadienyl]-4(1H)-quinolone(15),evocarpine A(16),evocarpine B(17),evocarpine C(18),evocarpine D(19),evocarpine E(20),evocarpine F(21),atanine I(22),preskimmianine(23),dictamnine(24),evolitrie(25),6-methoxydictamnine(26),skimmiamine(27),evodianine(28),rutaecarpine(29),7-hydroxyrutaecarpine(30),3-hydroxyacetylindole(31),N-(trans-p-coumaroyl)-tyramine(32),N-(tra pan-coumaroyl)-tyramine(33);eight limonins derivatives,limonin(34),rutaevine(35),rutaevine acetate(36),jangomolide(37),6?-acetoxy-5-epilimonin(38),evodol(39),12?-hydroxyevodol(40),isolimonexic acid(41);six flavonoids,genkwanin(42),apigenin(43),5,7,4'-trihydroxy-3,3'-dimethoxy-flavonol(44),rhamnatin(45),5,4'-dihydroxy-3,7,3'-trimethoxyflavone(46),Quercetin(47);four coumarins,umbelliferone(48),6,7,8-trimethoxy-coumarin(49),(+)-trans-decursidinol(50),marmesin(51);nine sterides and triterpenes,stigmasterol(52),sitost-5-en-3?-ol acetate(53),sitosterone(54),?-sitosterol(55),7-oxo-?-sitosterol(56),7a-hydroxysitosterol(57),oleanolic acid(58),ursolic acid(59),pomolic acid(60);six phenolic acids,vanillic acid(61),syringic acid(62),p-hydroxyl benzoic acid(63),trans-ferulic acid(64),p-hydroxyphenyol(65),gallic acid(66).Among of these compounds,16?21 are new compounds;1,4,12,14 are novel natural products;23,31,42,44,49,51 are isolated from Euodia genus for the first time;22,24?27,32,33,46,50,53,54,56,57,60 are isolated from E.rutaecarpa Benth.species for the first time.2.The fingerprint of E.rutaecarpa Benth.via HPLC-DAD/ESI-MSn technology was established,and this fingerprint combined the water-soluble and fat-soluble chemical contents into one which reflected the full view of the chemical constituents of E.rutaecarpa Benth.The hierarchical clustering analysis(HCA)was performed to differentiate and classify the samples.3.We also screened the antibacterial,cytotoxicity and anti-inflammatory activities of some compounds isolated from the fruits of E.rutaecarpa.The results revealed that compounds 5,7-11,13,14,and 16-20 exhibited moderate antibacterial activities(MIC values:4-128,?g/mL),and compounds 9,11,14,and 17 exhibited moderate cytotoxic activities against HepG-2,Hela,BEL7402,and BEL7403(IC50 values:15.85-56.36 ?M);compounds 1-3,7,13,18 showed positive anti-inflammatory activity(IC50 values:13.85-15.45 ?M).