Synthesis Of Celangulin Derivatives

In order to study the relationship between structure and insecticidal activity ofβ-dihydroagarofuran compounds, 1β, 2β, 4α, 6α, 8β, 9α,12-hepthydroxy-β-dihydroagarofuran polyol—the basic hydrolysis of the extract of the root bark of Celastrus angulatus Maxim was used as starting material, reactioned with Methylsulfonyl chloride, reductioned by LiAlH4, to give 1β, 4α, 6α, 9α-tetrahydroxy-2β, 12- ether-β-dihydroagarofuran, then esterified and etherified. The starting material was protected by acetone, then etherfied with several halohydrocarbons. Most of the compounds were evaluated on their insecticidal activity and cytotoxicity, and their structures were elucidated mainly based on NMR, IR and HRMS spectral datas.1,Compound S and its seven ether derivatives(a-g) and two ester derivatives(h,i) were synthesized, their structures were elucidated mainly based on NMR, IR and HRMS spectral datas.Bioassay results indicate that seven ether derivatives(a-g) have insecticidal activity with mortality of 44.9%-86.2%, diallylether and tributylether analogues exhibited more higher insecticidal activity than Celangulin V against 3rd-instar larvae of Mythimna separata. Ethylester derivative (h) and isobutylester derivative (i) have no obvious insecticidal activity.2,Compound T and its ether deveratives(j-t) were synthesized, structures were elucidated mainly based on NMR spectral datas. Bioassay results indicate that only ethylether(k), n-propylether(l), dibutylether(o) and dipentylether(q) have certain insecticidal activity, the others have no insecticidal activity.3,n-propylether(c), dibutylether(e), tributylether(f) and methylether(j) have more cytotoxicity against Heliothis armigera Hübner Ovaria cell in vitro.These results are useful for the future research about celangulins.