桦木酸/二乙烯三胺链-β-环糊精包合物的制备及水溶性研究

doi:10.3969/j.issn.0253-2417.2016.02.005

摘要/Abstract

摘要： 以β-环糊精(β-CD)为原料,合成二乙烯三胺链-β-环糊精 (DETA-β-CD)主体分子,并与桦木酸(BA)进行包合反应,采用饱和水溶液法和冷冻干燥技术制备出粉末态的BA/DETA-β-CD包合物,采用红外 (IR)、核磁(¹H NMR)及扫描电镜 (SEM)等分析手段,阐明DETA-β-CD对BA的分子识别机制及主-客体包合模式,并利用质谱(MS)和超高效液相色谱(UPLC)测定包合物中BA含量。结果表明,DETA侧链上的伯胺基团与BA的羧基生成氢键,BA的疏水部分从β-环糊精小口端进入并被包含,DETA-β-CD的疏水空腔及低聚乙烯胺侧链可以对BA产生多重识别效应,将BA溶解度由4.7×10^-5 mmol/L提高到15.33 mmol/L。

关键词: 桦木酸, 环糊精, 包合物, 水溶性

Abstract: Using β-cyclodextrin (β-CD) as raw material, the host molecule of diethylenetriamine-β-cyclodextrin (DETA-β-CD) was synthesized to encapsulate betulinic acid (BA). Saturated water solution method and freeze drying technique were used to prepare the solid state powder of BA/DETA-β-CD complex. IR, ¹H NMR and SEM were used to illustrate the molecule recognition mechanism and host-guest interaction mode. MS and UPLC were employed to determine the BA content encapsulated in the complex. The results show that the hydrophobic of BA can penetrate into the DETA-β-CD cavity from the narrow side due to the hydrogen-bond interaction between the tether amino group and BA carboxyl group. The water solubility of BA was remarkably increased from 4.7×10^-5 mmol/L to approximately 15.33 mmol/L due to the multiple identification effect on BA from the hydrophobic cavity of DETA-β-CD and low polyvinyl amine side chain.

Key words: betulinic acid, cyclodextrin, complex, water solubility

中图分类号:

TQ35

董仕辉, 崔铭锦, 刘卫, 朱笛, 杜一博, 王霆. 桦木酸/二乙烯三胺链-β-环糊精包合物的制备及水溶性研究[J]. 林产化学与工业, 2016, 36(2): 30-36.

DONG Shi-hui, CUI Ming-jin, LIU Wei, ZHU Di, DU Yi-bo, WANG Ting. Preparation and Water Solubility of Betulinic Acid/Diethylenetriamine-β-cyclodextrin Complex[J]. Chemistry and Industry of Forest Products, 2016, 36(2): 30-36.

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