Chemical Study On The Constituents Of Xylocarpus Granatum Twig

The genus Xylocarpus,distributed widely in the coastal areas of South-East Asia,East Africa,Australia and Indian Ocean,and has been found in Hainan,China.This genus includes three plants,namely Xylocarpus granatum Koenig,Xylocarpus moluccensis and Xylocarpus rumphii.Xylocarpus granatum Koenig can treat diseases such as diarrhea and dysentery in some countries,and can also be used as an insecticide and antipyretic.People also used it as a tonic in Hainan.Studies have shown that the plant has a variety of biological activities such as:antidiarrheal,insect resistance,cytotoxicity and antibacterial.Our group has been conducting research on Xylocarpus granatum Koenig.In order to develop its medicinal value more effectively,we studied the chemical constituents of its twigs collected from Hainan,China,the ethyl acetate fraction was subjected to systematic separation and purification,and the chemical structures of the obtained compounds has been identified.Objective:Using CC as the classification method,TLC as the detection means,PTLC,P-HPLC as the purification method to isolate and purify the compunds of the ethyl acetate fraction.The structures of the pure compounds were elucidated by methods of ¹H-NMR,¹³C-NMR,¹H-¹H COSY,HSQC,HMBC in order to exploid new medicinal natural products.Methods:Dried twigs?7 kg?of X.granatum were extracted with 95%ethanol.After evaporation of the solvent under reduced pressure,the residue was suspended in water and extracted with ethyl acetate in order for three times.Using PTLC,P-HPLC to isolate and purify the components,¹H-NMR,¹³C-NMR,¹H-¹H COSY,HSQC,HMBC to identify the structures of the compounds.Results:There were 26 compounds were identified from the twigs of X.granatum,they are:6-deoxydestigloyl-23-hydroxy-21-furanone swie tenin acetate?1?,6-deacetoxy-14,15-en-1,8,9-trihydroxyl Xylocarpin I?2?,6-deacetoxy-23-hydroxy-21-furanone-Xylocarpin I?3?,6-deacetoxy-Xyloc arpin I?4?,Ergosta-4,21-dien-20-oic acid?5?,2-hydroxyl-4-methoxy-6-?2-oxoheptyl?-ethyl benzoate?6?,4-hydroxyl-6-dimethoxy-2-pentyl-benzofura n?7?,2-deacetoxyl-xyloccensin V?8?,Xylocarpin I?9?,Xylocarpin G?10?,Granaxylocarpin B?11?,1-acetyl-2-deacetoxyl-xyloccensin V?12?,6-deoxydestigloyl swietenin acetate?13?,Stigmast-3-ol-5-en?14?,Stigmasta-5,22-dien-3-ol?15?,9,19-cycloergost-24?28?-en-3-ol?16?,9,19-cycloergost an-3-ol?17?,Pregn-4-ene-3,20-dione?18?,1,2-benzenedicarboxylic acid?19?,Depcitrus B?20?,3,4-dihydroxybenzoic acid ethyl ester?21?,1,8-o ctanedione methyl ester?22?,1,8-octanedione ethyl ester?23?,P-hydroxy benzaldehyde?24?,2,6-dimethoxy-1,4-benzoquinone?25?,Kaur-16-en-18-oic acid?26??Conclusions:Through the separation and purification of the chemic al constituents of the ethyl acetate fraction of the twigs of X.granatum,26 compounds were identified,there are seven compounds were new,i ncluding 4 limonoids and 1 steroid,1 aromatic ester compound,1 benz ofuran compound;they are:6-deoxydestigloyl-23-hydroxy-21-furanone sw ietenin acetate?1?,6-deacetoxy-14,15-en-1,8,9-trihydroxyl Xylocarpin I?2?,6-deacetoxy-23-hydroxy-21-furanone Xylocarpin I?3?,6-deacetoxy-Xylocarpin I?4?,Ergosta-4,21-dien-20-oic acid?5?,2-hydroxyl-4-methoxy-6-?2-oxoheptyl?-ethyl benzoate?6?,4-hydroxyl-6-dimethoxy-2-pentyl-benz ofuran?7?.