Amino Acid Ester based Phenolic Ionic Liquids as a Potential Solvent for the Bioactive Compound Luteolin: Synthesis, Characterization, and Food Preservation Activity

Islam Md Shimul, Rahman Md Moshikur, Kosuke Minamihata, Muhammad Moniruzzaman, Noriho Kamiya, Masahiro Goto

研究成果: ジャーナルへの寄稿学術誌査読

5 被引用数 (Scopus)

抄録

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 through 1H 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 with p-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.

本文言語英語
論文番号118103
ジャーナルJournal of Molecular Liquids
349
DOI
出版ステータス出版済み - 3月 1 2022

!!!All Science Journal Classification (ASJC) codes

  • 電子材料、光学材料、および磁性材料
  • 原子分子物理学および光学
  • 凝縮系物理学
  • 分光学
  • 物理化学および理論化学
  • 材料化学

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