果糖嗪的合成及抗衰老评价

Synthesis and anti-aging evaluation of fructosazine

摘要:

以D-葡萄糖为原料通过Amadori重排、异丙叉保护、Pd/C催化加氢脱苄基和氧化芳构化串联反应、脱异丙叉保护四步反应得到目标化合物果糖嗪，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1 μmol/L，可以上调细胞活力，为对照组的125%。衰老标志物β-半乳糖苷酶（SA-β-Gal）法对果糖嗪的抗衰老活性进行评价，以1 μmol/L果糖嗪连续传代培养衰老早期细胞和衰老中期细胞，其蓝染率降低分别为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。

Abstract:

Fructosazine was synthesized from D-gluctose by 4 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, X-ray single crystal diffraction. The MTT method was used to determine the effect of fructosazine on the viability of human fibroblast cells (2BS cells). Compared with the control group, 2BS cell viability was significantly enhanced 25% by 1 μmol/L fructosazine. The aging marker β-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 2BS cells, which were continuously cultured with 1 μmol/Lfructosine, were 14% and 19% less than that of the control group respectively. The results showed that fructosazine had anti-aging activity on 2BS cells in the early or middle stage of aging.