Synthesis And Bioactivity Of Multi-functional Natural Product Pterostilbene And Its Derviantives

Natural products contain a large number of chemicals with potential functions,and often have unique biological activities and action targets.Natural extracts pterostilbene is metabolite of resveratrol,which is named for detecting in the red sandalwood originally,extensively exists in berry just like blueberry and grape.The pterostilbene and its derivatives are increasingly raised into a high level of attention in medicine,food,health product,cosmetic and even agriculture field because of various activities such as antioxidant,hypolipidemic,suppression of cell proliferation,anticancer action,antimycotic result,restrain COX-1 and COX-2.The study focus on following two parts:1.With 3,5-dimethoxybenzaldehyde and 4-Hydroxyphenylacetic acid as raw materials,the pterostilbene was synthesized by three steps:Perkin reaction,deacetylation and decarboxylation.The structure of pterostilbene was confirmed by Melting point,¹H NMR and IR.The synthetic conditions were optimized,and the total yield of three steps reached to 71.1%（based on3,5-dimethoxybenzaldehyde）.Compared with other synthetic routes mentioned in references,this route has following advantages:cheap and facile raw material,mild reaction condition,higher yield and easily large-scale production.2.Five pterostilbene derivatives were designed and synthesized:（E）-4-（3,5-Dimethoxysty-ryl）phenyl dihydrogen phosphate（3）,（E）-1,3-Dimethoxy-5-（4-（（3-methylbut-2-en-1-yl）oxy）styryl）benzene（6）,（Z）-1,3-Dimethoxy-5-（4-（（3-methylbut-2-en-1-yl）oxy）styryl）benzene（7）,（E）-4-（3,5-Dimethoxystyryl）-2-（3-methylbut-2-en-1-yl）phenol（11）,（Z）-4-（3,5-Dimethoxystyryl）-2-（3-methylbut-2-en-1-yl）phenol（12）.Their structures were confirmed by ¹H NMR,¹³C NMR and HRMS.The results of biological activities test showed that compounds 11,12 have strong Aedes aegypti larvicidal activity(LC₅₀0 14.7 and 16.2 ppm).Futhermore,the lethality rate about larvae of Ae.aegypti in pesticide-susceptible and pyrethroid-resistant strains were respectively100%and 93.9%while concentration of compound 11 was 1μg/mL.In addition,all of compounds show certain fungicidal activities against target fungi of plant.Thus,pterostilbene derivatives are valuable for further research.