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This dissertation includes two parts: LC-MS guided isolation of sesquiterpenoidsfrom Carpesium abrotanoides L., LC-MS guided isolation of inositol derivatives andsesquiterpenoids from Inula cappa; and modification of natural product with potentbiological activities. In Chapter one, a total of 60 compounds were isolated from Calpesiumabrotanoides L., including sesquiterpenoids dimers, nor-sesquiterpenoids,sesquiterpenoids, and diterpenoids; 38 0f them were identified as new compoundsincluding 6 novel skeletons (Figure la-lc). A LC-MS guided method was applied toisolate the sesquiterpenoids dimers and nor-sesquiterpenoids. To the best of ourknowledge. compounds l-10 represent the first examples of dimeric carabronesesquiterpene lactones Compounds l-4 and compound 8 dimerized fromsesquiterpene lactones via a [3 + 2] cycloaddition. The structure ofnor-sesquiterpenoids (11-18) showed gleat similarities, the plausible biosyntheticrelationship of them was confirmed by chemical transformation experiments. Thetypes of sesquiterpenoids that had been found in C. abrotanoides are the guaiane,pseudoguaiane, eudesmane, eremophilan, germacrane and carabrone types. Mostisolated sesquiterpenoids were evaluated for their cytotoxic effects on A431, A549,BGC-823. HL-60. HT-29 and MCF-7 cancer cell lines, and compound 49 showedsignificant effects on these cells. In Chapter two, 12 new inositol derivatives along with 7 known ones, 2 newsesquiterpenoids along with 3 known ones were isolated from Inula cappa (Figure2a-2b). A LC-MS guided method was applied to isolate the inositol derivatives. Mostthe isolated inositol derivatives were evaluated for the anti-inflammatory activities,and compound 76 showed potent anti-inflammatory activities with aninhibitoryrate of 59.6％ at the concentration of 10 ,uM, while positive control 59.2% at the sameconcentration. All isolated sesquiterpenoids were evaluated for their cytotoxic effectson A431, A549, BGC-823, HL-60, HT-29 and MCF-7 cancer cell lines, and allcompounds showed significant effects on these cells. In Chapter three. a modification based on natural product with potent biologicalactivities was carried out to seek derivatives with high bioactivity but low toxicity. Atotal of 44 derivatives were synthesized based on Lipinskis rule.