果糖嗪的合成及抗衰老评价  

Synthesis and anti-aging evaluation of fructosazine

作　　者：姜丁宁 李悦青[1,2] 郭修晗 李广哲[1] 王世盛 赵伟杰[1] JIANG Dingning;LI Yueqing;GUO Xiuhan;LI Guangzhe;WANG Shisheng;ZHAO Weijie(State Key Laboratory of Fine Chemicals,Department of Pharmaceutical Sciences,School of Chemical Engineering,Dalian University of Technology,Dalian 116024,Liaoning,China;Ningbo Institute of Dalian University of Technology,Ningbo 315016,Zhejiang,China)

机构地区：[1]大连理工大学化工学院药学系精细化工国家重点实验室,辽宁大连116024 [2]大连理工大学宁波研究院,浙江宁波315016

出　　处：《精细化工》2021年第8期1644-1649,1659,共7页Fine Chemicals

基　　金：国家自然科学基金(21706024)。

摘　　要：以D-葡萄糖为原料,通过Amadori重排、异丙叉基保护、Pd/C催化加氢脱苄基和氧化芳构化串联反应、脱异丙叉保护4步反应得到果糖嗪,HPLC纯度达96%。使用NMR、MS、X射线单晶衍射技术对关键中间体异丙叉基果糖嗪的结构进行了表征。使用噻唑蓝(MTT)法测定果糖嗪对人胚肺二倍体成纤维细胞(2BS细胞)活力的影响,筛选获得最佳培养浓度为1μmol/L,可以上调细胞活力,为对照组的125%。采用细胞衰老β-半乳糖苷酶(SA-β-Gal)染色法对果糖嗪的抗衰老活性进行了评价,以1μmol/L果糖嗪连续传代培养衰老早期细胞和衰老中期细胞,其蓝染率比对照组分别降低了14%和19%。实验表明,果糖嗪对衰老早期或中期的2BS细胞都有抗衰老活性。Fructosazine with HPLC purity of 96% was synthesized from D-gluctose by four steps,including Amadori rearrangement,isopropylidene protection,cascade reaction of hydrodebenzylation and oxidative aromatization catalyzed by Pd/C,and removal of isopropylidene protection.The structure of the key intermediate isopropylidene fructosazine was characterized by NMR,MS and X-ray single crystal diffraction.The methyl thiazolyl tetrazolium(MTT)assay was used to determine the effect of fructosazine on the viability of human fibroblast cells(2 BS cells).The optimal culture concentration of fructosazine was 1μmol/L,which could upregulated cell viability and was 125% of that of control group.The senescenceassociatedβ-galactosidase(SA-β-Gal)method was used to evaluate the anti-aging activity of fructosazine.The blue staining rate of early-senescent and mid-senescent 2 BS cells were reduced by 14% and 19% compared with that of control group,respectively,which were continuously cultured with 1μmol/L fructosazine.The results showed that fructosazine had anti-aging activity on 2 BS cells in the early or middle stage of aging.

关 键 词：果糖嗪 Amadori重排 Pd/C催化脱苄基 Pd/C催化氧化芳构化 抗衰老 医药原料 

分 类 号：TQ245[化学工程—有机化工]