2016 年 74 巻 6 号 p. 611-620
The first structure determination of the new juvenile hormone (JH) isolated from a heteropteran insect, Plautia stali is described. To identify the target JH, a new isolation approach starting from a JH molecular library was attempted. We proposed the structure of the target JH based on the in vitro radiochemical TLC and mass analyses of the corpus allatum product of P. stali. The molecular library including 32 molecules was prepared from geranylacetone. The mixture was screened by the bioassay-guided separation using P. stali. The highly potent JH molecules found in the library were subjected to GCMS analysis to identify the naturally occurring heteropteran JH obtained from P. stali. One of the candidates was identical with the natural product by a chiral GCMS analysis. The novel JH was named as juvenile hormone III skipped bisepoxide(JHSB3). To identify the key functional groups of JHSB3, we conducted the structure-activity relationship study of JHSB3. These results as well as our efforts for the stereoselective synthesis of JH0 and JHI are also described.