The Enzymatic Synthesis Of The Dehydrodimer Of Resveratrol--cis-δ-viniferin And The Study Of Its Function

Trans-resveratrol is a kind of natural phytoalexin that can be found in many plants, especially in grapes.Studies have shown that resveratrol have a series of pharmacological activities at home and abroad.Resveratrol can be transformed intoδ-viniferin,ε-viniferin and other metabolites in plants.As the oligomers of resveratrol,viniferins are known to have many bioactivities,such as anti-microbial,anti-oxidant,anti-inflammatory,anti-HIV.Recently it had been discovered that,compared with resveratrol,δ-viniferin could show greater inhibition effects on microbial,COX-1 and COX-2.Therefore,the research onδ-viniferin has become a new focus of stilbene compounds.However,theδ-viniferin only exists in plants with a quite low content.And until now,there were few papers about biocatalyzed of resveratrol to prepareδ-viniferin in vitro,which hampered the studies of its biological properties.In this research,resveratrol was catalyzed by laccase to prepare the dehydrodimer of resveratrol.The identification results proved that the isolated production we got was cis-δ-viniferin.Its biological property was then preliminarily discussed. The results were as follows:Resveratrol was dealed with laccase.After optimizing reaction system,the yield had been raised to 38%,and the reaction time had been shortened to 1 hour.The reaction system contained: 1 g ofresveratrol,10 ml laccase,40℃(as the reaction temperature),1 hour(as the reaction time), air injection and excessive Na₂S₂O₃.We selected a more effective separation method from Al₂O₃ column,silica gel column, macroporous resin column and polyamide column.The system of separation contained: polyamide(100 mesh) as the filler,the column(3×28 cm),chloroform:methanol(6:5),real time HPLC control. With TLC,HPLC and LC-MS analysis,the production was proved to be a kind of resveratrol dimmer.And the NMR data had confirmed that the obtained production was cis-δ-viniferin.Compared with resveratrol,the effect of cis-δ-viniferin on MCF-7 cells was studied.The result showed that both cis-δ-viniferin and resveratrol could inhibit the proliferation of MCF-7 cells,and resveratrol could promote the apoptosis of the cell.