Synthesis, Spectroscopic Study and Radical Scavenging Activity of Kaempferol Derivatives: Enhanced Water Solubility and Antioxidant Activity

International Journal of Molecular Sciences
Sui-Ping DengJi-Ye Cai

Abstract

Kaempferol (Kae) is a natural flavonoid with potent antioxidant activity, but its therapeutic use is limited by its low aqueous solubility. Here, a series of Kae derivatives were synthesized to improve Kae dissolution property in water and antioxidant activity. These compounds included sulfonated Kae (Kae-SO₃), gallium (Ga) complexes with Kae (Kae-Ga) and Kae-SO₃ (Kae-SO₃-Ga). The compound structures were characterized by high-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR) spectroscopy, ultraviolet-visible (UV-Vis) spectroscopy, Fourier transform infrared (FT-IR) spectroscopy and thermal methods (TG/DSC). The results showed that a sulfonic group (-SO₃) was successfully tethered on the C3' of Kae to form Kae-SO₃. And in the metal complexation, 4-CO and 3-OH of the ligand participated in the coordination with Ga(III). The metal-to-ligand ratio 1:2 was suggested for both complexes. Interestingly, Kae-SO₃-Ga was obviously superior to other compounds in terms of overcoming the poor water-solubility of free Kae, and the solubility of Kae-SO₃-Ga was about 300-fold higher than that of Kae-Ga. Furthermore, the evaluation of antioxidant activities in vitro was carried out for Kae derivatives by using α,α-diphenyl-β...Continue Reading

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Citations

Mar 26, 2021·Journal of Agricultural and Food Chemistry·Xiao WangZhong Zhang

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Methods Mentioned

BETA
nuclear magnetic resonance
NMR
differential scanning calorimetry
ABTS

Software Mentioned

SPSS

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