NMR spectroscopic and quantum mechanical analyses of enhanced solubilization of hesperidin by theasinensin a

Ruge Cao, Yutaro Kobayashi, Airi Nonaka, Yuji Miyata, Kazunari Tanaka, Takashi Tanaka, Toshiro Matsui

研究成果: Contribution to journalArticle査読

12 被引用数 (Scopus)

抄録

Purpose: The use of hesperidin in the pharmaceutical field is limited by its aqueous insolubility. The effects of natural compounds in tea on the solubility of hesperidin were evaluated and the underlying mechanism was investigated by nuclear-magnetic resonance (NMR) and quantum mechanical calculations. Methods: The solubility of hesperidin was measured by liquid chromatography time-of-flight mass spectrometry; the structure of the hesperidin/theasinensin A complex was characterized by 1H-NMR, diffusion-ordered NMR spectroscopy, and rotating frame NOE spectroscopy, as well as theoretically by quantum mechanical calculations. Results: Among the natural compounds in tea, theasinensin A was the most effective in improving hesperidin solubility. The complexation of hesperidin with theasinensin A led to changes in the chemical shift of protons in hesperidin (Δδ: 0.01-0.27 ppm) and diffusion coefficient (ΔD: 0.66-1.32∈×∈10-10 m2/s) of hesperidin. ROE correlation signals between hesperidin and theasinensin A and quantum mechanical calculations revealed that two hesperidin molecules formed a stable complex with theasinensin A (2:1 complex) with a ΔG energy of -23.5 kJ/mol. Conclusions: This is the first study that provides insight into the enhanced solubility of hesperidin through interactions with theasinensin A via a 2:1 complex formation between hesperidin and theasinensin A.

本文言語英語
ページ(範囲)2301-2309
ページ数9
ジャーナルPharmaceutical Research
32
7
DOI
出版ステータス出版済み - 7 30 2015

All Science Journal Classification (ASJC) codes

  • バイオテクノロジー
  • 分子医療
  • 薬理学
  • 薬科学
  • 有機化学
  • 薬理学(医学)

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