Page 150 - 《精细化工》2021年第8期

第 38 卷第 8 期 精 细 化 工 Vol.38, No.8
202 1 年 8 月 FINE CHEMICALS Aug. 2021

医药与日化原料
果糖嗪的合成及抗衰老评价

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姜丁宁 ，李悦青 1,2* ，郭修晗 1,2 ，李广哲 ，王世盛 1,2 ，赵伟杰
（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）

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 1 μmol/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 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。
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
中图分类号：TQ245 文献标识码：A 文章编号：1003-5214 (2021) 08-1644-07

Synthesis and anti-aging evaluation of fructosazine

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JIANG Dingning , LI Yueqing 1,2* , GUO Xiuhan , LI Guangzhe ,
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WANG Shisheng , ZHAO Weijie
（1. State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering,
Dalian University of Technology, Dalian 116024, Liaoning, China; 2. Ningbo Institute of Dalian University of Technology,
Ningbo 315016, Zhejiang, China）
Abstract: 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 (2BS cells). The optimal culture concentration of fructosazine was
1 μmol/L, which could upregulated cell viability and was 125% of that of control group. The senescence-
associated 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 were reduced by 14% and 19%
compared with that of control group, respectively, which were continuously cultured with 1 μmol/L
fructosazine. The results showed that fructosazine had anti-aging activity on 2BS cells in the early or
middle stage of aging.
Key words: fructosazine; Amadori rearrangement; hydrodebenzylation by Pd/C; oxidative aromatization
by Pd/C; anti-aging; drug materials

[1]
吡嗪类化合物是具有双氮六元杂环结构的一类 抗菌、抗氧化 等多种生理和药理活性。果糖嗪（FZ）
化合物，其特定结构致使这类化合物均具有优异的 和脱氧果糖嗪（DOF）是一类吡嗪类化合物，在烘

收稿日期：2021-01-28; 定用日期：2021-04-15; DOI: 10.13550/j.jxhg. 20210111
基金项目：国家自然科学基金（21706024）
作者简介：姜丁宁（1994—），女，硕士生，E-mail：1558353341@qq.com。联系人：李悦青（1977—），女，副教授，E-mail：yueqingli@
dlut.edu.cn。