Study On The Structural Modification And Bioactivities Of Diterpenoid From Wedelia Prostrata,Chemical Constituents And Bioactivities Of Canavalia Maritima

Objectives:Through the structural modification of ent-kaurane diterpenoid from Wedelia prostrata,lupeol from Scurrula parasitica and isolation of the fruits of Canavalia maritima.,a series of diterpenoid and triterpenoid derivatives and isolated compounds were obtained.In order to get better antitumor compounds,the MTT assay was used to screen the anti-tumor activity for these compounds.Methods:(1)Synthetic methods:(a)Used ent-kaurane as starting material to introduce the efficacy of functional groups of ?,?-unsaturated ketone,the strategy was applied to modify the carbanyl group at C-15 and carboxyl group at C-19.For carboxyl group at C-19,substitution reactions,esterification reactions,amidation reactions and ester bond inversion reactions were utilized.For carbanyl group at C-15,the imide group was introduced.Through these methods,a series of derivatives were obtained,such as W1-3~W1-18 of diterpenoid derivatives.(b)Used lupeol L2 as starting material,a series of derivatives were obtained,such as L2-1~L2-5 of triterpenoid derivatives through substitution reactions and esterification reactions.(2)Isolation methods: powdered fruits of Canavalia maritima(Aubl.)Thou were extracted three times with MeOH.After evaporation of the solvent,the residue was suspended in H2 O and extracted with petroleum ether(PE),AcOEt,and BuOH,successively.The silica gel,Sephadex LH-20 gel,semi-preparative HPLC,MCI gel column chromatography,and etc.were used to isolate the AcOEt extraction.(3)Bioactivity assay: The MTT assay method was applied to screen the anti-tumor activity for the compounds which were obtained by synthesis and isolation.(4)Structure-activity relationship studying: The structure-activity relationship was summarized by comparing the antitumor activity data.Results:(1)Used the above modifications and isolation methods,16 derivatives of ent-kaurane(W1-3~W1-18),a new kaurane diterpenoid compound,5 derivatives of lupeol(L2-1~L2-5),7 compounds(C1~C7)from the fruits of Canavalia maritima were obtained.All of the compounds were characterized by 1H-NMR,13C-NMR and MS spectra.(2)From the antitumor activity data,it was showed that the activity of ent-kaurane derivatives were improves greatly than starting material W1 and some derivatives showed superb activity for some special tumor cells.But the activity of lupeol derivatives were decline after the modification at C-3.The compounds isolated from Canavalia maritima can inhibit the growth of tumor cells to a certain degree.Conclusion:The derivatives of ent-kaurenes have better activity than the staring material for tumor cells,It was worth to carry on further study.But the anti-tumor activity of lupeol derivatives were low.Further studying for its antiviral activity was suggested.