Bioactive Constituents Of Stellera Chamaejasme, Zanthoxylum Nitidum And Geranium Strictipes

The ethanol extracts of Stellera chamaejasme (Thymelaeaceae) roots and Zanthoxylum nitidum (Rutaceae) rhizomes were screened using Pyricularia oryzae P-2b as indicator organism and showed the antimitotic and antifungal activity. The extract of Geranium strictipes (Geraniaceae) roots exhibited the anti-HIV activity. In order to find potent antimitotic, antifungal, anti-HIV, and anti-HBV bioactive principles, these three medicinal plants were investigated phytochemically and pharmacologically.1. Phytochemical investigation on the EtOAc and petroleum ether soluble extract of the roots of Stellera chamaejasme led to the isolation of 22 and 3 compounds, respectively, 23 of them were identified with UV, IR, MS and NMR spectra. There are 12 C-3/C-3" biflavanones, 4 coumarins, 3 flavones, 1 chromone, 1 cinnamic acid derivative, 1 sterol and 1 sulfur. Their structures were elucidated as chamaejasmenin D (SC-1), isochamaejasmenin B (SC-2), isosikokianin A (SC-3), isodaphnoretin B (SC-4), chamaejasmenin A (SC-5), chamaejasmenin B (SC-6), chamaejasmenin C (SC-7), ruixianglangdusu A (SC-8), 7-methoxyineochamaejasmin A (SC-9), sikokianin A (SC-10), sikokianin C (SC-11), neochamaejasmin A (SC-12), isoneochamaejasmin A (SC-13), chamaechromone (SC-14), apigenin (SC-15), quercetin (SC-16), rutin (SC-17), daphnoretin (SC-18), umbelliferone (SC-19), 5,7-dihydroxycoumarin (SC-20), p-hydroxycinnamic acid n-octadecyl ester (SC-21), β-sitosterol (SC-22), and sulfur-8 (SC-23). Among them, SC-1, SC-2, SC-3, SC-4 were new compounds, and SC-10, SC-11, SC-15, SC-16, SC-17, SC-20, SC-21, SC-23 were isolated from this species for the first time.2. The antimitotic and antifungal bioassay of these compounds isolated from Stellera chamaejasme were screened using Pyricularia oryzae P-2b as indicator organism. Among these compounds, the known compound SC-5 and new compounds SC-1, SC-2 demonstrated potent antimitotic and antifungal activity, they inhibited themycelia growth of P. oryzae with minimum inhibitory concentration (MIC) values of 3.12, 6.25, 6.25μg/ml, respectively, SC-6, SC-10 and SC-12 showed weak activity, and SC-7 was inactive. These bioactive compounds were all C-3/C-3" biflavanones, and coumarins screened were inactive. Structure-activity correlations of antimitotic and antifungal C-3/C-3" biflavanones were discussed preliminary. The structural differences between apparently active compounds SC-5, SC-1, SC-2 and weakly active compounds SC-6, SC-10, SC-12 or inactive compound SC-7 are number and positions of methoxyl substitutions, and relative configuration of 2-H/3-H, and 2"-H/3"-H, which might be important to the antimitotic and antifungal activity of these C-3/C-3" biflavanones against P. oryzae.3. Phytochemical investigation on the 2% H2SO4 soluble extract of the rhizome of Zanthoxylum nitidum yielded 9 compounds, and 7 of them were identified. There are 1 benzophenanthridine, 4 quinoline alkaloids and 2 coumarins. Their structures were elucidated as 6-methoxy-5,6-dihydronitidine(ZN-l), dictamnine(ZN-2), Y -fagarine (ZN-3), skimmianine (ZN-4), 5-methoxydictamnine(ZN-5), toddanone (ZN-6), toddalolactone(ZN-7). Among them, ZN-1, ZN-3, ZN-5, ZN-6, ZN-7 were isolated for the first time from this species. The structural data of single crystal X diffraction of ZN-1 and ZN-6 was obtained for the first time.The antimitotic and antifungal bioassay of ZN-1~5 were performed using P. oryzae. Among these compounds, ZN-2, ZN-3, and ZN-5 demonstrated potent antimitotic and antifungal activity, they inhibited the mycelia growth of P. oryzae with MIC values of 6.25, 6.25, 6.25μg/ml, respectively, ZN-4 showed weak activity with MIC value of 25μg/ml, and ZN-1 was inactive. ZN-2-5 were all quinoline alkaloids and ZN-1 was benzophenanthridine alkaloid, which indicated quinoline alkaloids might be main antimitotic and antifungal active principles of Zanthoxylum nitidum. Number of methoxyl substitutions might be affect the antimitotic and antifungal activity.4. Seven compounds were isolated from the EtOAc soluble extract of the roots of Geranium strictipes by repeated column chromatography and their structures were identified with UV, IR, MS and NMR spectra. There are 6 tannins and 1 phenic acid. Their structures were elucidated as β-1, 4, 6-tri-O-galloyl-D-glucose(GS-l), β-1, 6-di-O-galloyl-D-glucose(GS-2), ellagic acid(GS-3), methyl gallate(GS-4), gallic acid...