Derivative Synthesis Of Diosgenin, Cholesterol And Stigmasterol And Their Bioactivity Research

Steroids widely distribute in human body, animals, plants and microorganism, they are influential in biological reproduction and growth. Steroids are widely used in medicine, especially the steroid hormone drugs. As a class of important natural products , many steroids were proved to be active on tumor. The syntheses, structural modifications and bioactivity investigations of steroids have led to finding their structure-activity relationships, which are of great meaning for the further developing novel antitumor agents. Besides, some special steroids show plant regulation activity. Those steroids are called brassinolides(BRs).In this thesis, we synthesized 18 derivates of 3β-hydroxyl,6-carbonyl in high yielding from diosgenin. cholesterol and stigmasterol through Jones oxidation, chlorinated nickel/reduction by sodium borohydride and NBS selective oxidation. We also synthesized derivates of 5α-Br from cholesterol within 3 steps. Their structure were identified by IR、1H NMR、13C NMR、MS.In the bioassay of cytotoxicity on Leukemia cells(NB4) and Cervical cancer cells(HELA). We found that compounds YZ-1, YZ-5, YZ-6, YZ-9 and YZ-13 showed moderate inhibition against NB4 cell line. For YZ-5, the death rate at 5μM level were 58% after 24 hours, and 90% after 48 hours. Compounds YZ-5, YZ-9 and YZ-10 showed moderate inhibition on HELA cell line, with death rate 78% after 48 hour(YZ-5).The bioassay on plant regulation, indicated compounds YZ-3 and YZ-9 promoting the growth of radish roots and stems. Three days after the seed rumination , the growth inhibition rate are -62.24%, -68.80% and - 59.85%, -58.16%, respectively.