Amino Acid Ester based Phenolic Ionic Liquids as a Potential Solvent for the Bioactive Compound Luteolin: Synthesis, Characterization, and Food Preservation Activity
Amino Acid Ester based Phenolic Ionic Liquids as a Potential Solvent for the Bioactive Compound Luteolin: Synthesis, Characterization, and Food Preservation Activity
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DOI：
10.1016/j.molliq.2021.118103
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发表时间：
2021-11
影响因子：
6
通讯作者：
Islam Md Shimul;Rahman Md Moshikur;K. Minamihata;M. Moniruzzaman;N. Kamiya;M. Goto
中科院分区：
文献类型：
--
作者：
Islam Md Shimul;Rahman Md Moshikur;K. Minamihata;M. Moniruzzaman;N. Kamiya;M. Goto
离子液体作为难溶性生物活性化合物的有效增溶剂，受到了广泛的关注。木犀草素（LUT）是一种天然的生物活性化合物，由于其水溶性较差，其使用受到限制。为了解决这个问题，本研究报告了在环境温度下有效溶解LUT的潜在il。首先，利用cosmos - rs实际溶剂类导体筛选模型，从20个标准氨基酸乙酯阳离子和9个酚酸阴离子组合提出的180个潜在il中筛选出有前景的il；以无限稀释下LUT在il中的活度系数作为筛选标准。以具有生物相容性的脯氨酸乙酯和具有生物活性的酚酸（反式阿魏酸、香豆酸、对香豆酸和4-羟基苯甲酸）为原料，合成了4种脯氨酸乙酯酚酸酯（PEEP-ILs）。通过1h NMR、FT-IR、元素分析、TGA和DSC对合成的peep - il进行了表征。LUT在peep -IL （60% IL溶于水）中的实验溶解度表现出良好的溶解度。在peep -IL中，阿魏酸脯氨酸乙酯（IL[ProEt][Fer]）的LUT溶解度最好，其次是对香豆酸酯（IL[ProEt][Cou]）、香草酸酯（IL[ProEt][Van]）和4-羟基苯甲酸酯（IL[ProEt][Ben]）。1H NMR评估和cosmos - rs预测证实，il通过LUT与il之间的多重氢键、π−π和阳离子−π相互作用促进了LUT的增溶。生物相容性研究表明，peep - il与传统的咪唑类、吡啶类、吡咯吡啶类、哌啶类和morpholinium类il相比，具有较低的毒性。LUT溶解于新合成的peep - il中，在红苹果切片上表现出较好的感官特性。这些结果表明，peep - il可以作为传统有毒溶剂的潜在绿色替代品，用于溶解水溶性差的生物活性天然防腐剂。
Ionic liquids (ILs) have gained great attention as potent solubilizing agents of poorly soluble bioactive compounds. The use of Luteolin (LUT) – a natural bioactive compound – is limited because of its poor aqueous solubility. To address this issue, this study reports potential ILs for effectively solubilizing LUT at ambient temperature. First, promising ILs were screened from a potential 180 ILs that were proposed by the combination of 20 standard amino acid ethyl esters cations and nine phenolic acids anions using the conductor-like screening model for real solvents (COSMO-RS); the activity coefficients of LUT at infinite dilution in ILs were used as the screening criteria. Four proline ethyl ester phenolate ILs (PEEP-ILs) composed of a biocompatible proline ethyl ester and bioactive phenolic acids (trans-ferulic, vanillic,p-coumaric, and 4-hydroxybenzoic acid) were selected and synthesized. The synthesized PEEP-ILs were characterized through1H NMR, FT-IR, elemental analysis, TGA, and DSC. The experimental solubility of LUT in PEEP-ILs (60% IL in water) showed excellent solubility. Among the PEEP-ILs, proline ethyl ester ferulate (IL[ProEt][Fer]) exhibited the best LUT solubility, followed by ILs withp-coumarate (IL[ProEt][Cou]), vanillate (IL[ProEt][Van]), and 4-hydroxybenzoate (IL[ProEt][Ben]).1H NMR assessment and COSMO-RS prediction confirmed that the ILs facilitated the solubilization of LUT through multiple hydrogen bonding, π − π, and cation − π interactions between the LUT and the ILs. The biocompatibility study revealed that PEEP-ILs were relatively harmless and low toxicity compared with conventional imidazolium, pyridinium, pyrrolidinium, piperidinium, and morpholinium-based ILs. The LUT dissolved in the newly-synthesized PEEP-ILs and demonstrated better organoleptic properties on red apple slices. These results indicate that PEEP-ILs can be potential green alternatives to conventional toxic solvents for dissolving poorly water-soluble bioactive natural preservatives.