Limonoids From The Thai Mangrove Plant,Xylocarpus Granatum

The mangrove plant,Xylocarpus granatum,belongs to the family Meliaceae.It was widely distributed at the tropical coasts of Australia,Africa,Oceanian,Fiji,Southeast Asian,India,and the Hainan Island of China.The roots,fruits,and bark of X.granatum have antibacterial,detumescence,anti-inflammatory,and antipyretic effects.X.granatum is used for the treatment of malaria fever,diarrhea and cholera in India and southeast Asian countries.In order to investigate chemical constituents of seeds of X.granatum from Thailand,the following isolation and purification methods were employed.Dried seeds of X.granatum were extracted with 95% ethanol,followed by suspension in water and extraction with ethyl acetate.Thirty compounds were isolated by various chromatographies,including TLC,silica gel CC,RP-C18 CC,and HPLC.The structures of these compounds were identified by extensive spectroscopic techniques(NMR,UV,IR,ESI-MS).Twenty-seven limonoids,viz.thaixylogranins A?H(1?8),moluccensin V(9),swietenine(10),xyloccensin P(11),swietemahonin C(12),Wu-xyloccensin Q(13),godavarin F(15),3-O-acetylswietenolide(16),granatumin Q(17),angolensin C(18),fissinolide(19),swielimonoid A(20),swietemahonin E(21),deacetylgedunin(22),swietenin E(23),granatumin I(25),chisomicine A(26),3-de(2-methylbutanoyl)-3-propanoylcipadesin(27),(4S,4a S,5S,6a S,7R,7a R,9R,10 R,10a R,10 b R,13 a R,15S)-15-((R)-1-acetoxy-2-methoxy-2-oxoethyl)-4-(furan-3-yl)-4a,7,9,12-tetramethyl-2-oxo-2,4,4a,5,6,7,7a,8,9,10,10 a,10b-dodecahydro-6a,12-epoxy-7,9-methano[1,3]dioxolo[4’,5’:4,5]indeno[5,6-f]isochromen e-5,7a,10-triyl triacetate(28),14α-hydroxyswietenine diene(29)were obtained,together with one protolimonoid,viz.20,21,22,23-tetrahydro-23-oxoazadirone(24),and one cumarin,i.e.scopoletin(14).Among the above compounds(1-8)are new compounds.The results would benefit the future research on limonoids of the mangrove plant.