Complexation of Apigenin and Oxymatrine Leading to Enhanced Anti-inflammatory Activity

Apigenin (APG) is a well-known dietary flavonoid with multiple bioactivities, but its poor aqueous solubility may result in low oral bioavailability and thus compromised therapeutic effects. In the present study, APG was complexed with oxymatrine (OMT), a natural quinolizidine alkaloid, for enhanced...

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Published in:Journal of natural products (Washington, D.C.) D.C.), 2023-05, Vol.86 (5), p.1179-1188
Main Authors: Yuan, Dan, Wang, Ziling, Li, Bin, Li, Xiaoxuan, Wang, Yingyun, Wang, Xinyu, Cao, Jin, Guo, Yujie, Du, Hongzhi, Lu, Shan
Format: Article
Language:English
Subjects:
alkaloids
Alkaloids - pharmacokinetics
Animals
anti-inflammatory activity
Anti-Inflammatory Agents - pharmacology
apigenin
Apigenin - chemistry
Apigenin - pharmacology
bioavailability
fluorescence emission spectroscopy
Fourier transform infrared spectroscopy
hydrogen
hydrophobicity
Matrines
Mice
molecular dynamics
nuclear magnetic resonance spectroscopy
pharmacokinetics
quantum mechanics
Quinolizines - pharmacokinetics
Raman spectroscopy
Rats
solubility
therapeutics
van der Waals forces
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Summary:Apigenin (APG) is a well-known dietary flavonoid with multiple bioactivities, but its poor aqueous solubility may result in low oral bioavailability and thus compromised therapeutic effects. In the present study, APG was complexed with oxymatrine (OMT), a natural quinolizidine alkaloid, for enhanced anti-inflammatory activity, and the related mechanisms in the interaction of APG with OMT were investigated. Fourier transform-infrared spectroscopy, fluorescence spectroscopy, Raman spectroscopy, and proton nuclear magnetic resonance spectroscopy characterizations demonstrated the occurrence of an APG–OMT complex formed at a molar ratio of 1:2. Then, molecular dynamics simulations and quantum chemical calculations were utilized to elucidate that hydrogen bonding, van der Waals forces, and hydrophobic effects were the main forces acting in the formation of the APG–OMT complex. Pharmacokinetic studies in rats demonstrated that the oral bioavailability of APG in the APG–OMT complex was significantly higher than that of APG alone. Finally, bioactivity evaluation in the lipopolysaccharide-induced acute inflammatory injury mouse models showed that the APG–OMT complex exhibited more potent anti-inflammatory effects than APG alone. This study confirmed that APG and OMT exerted enhanced anti-inflammatory effects through self-complexation, which may provide a novel strategy for improving the bioavailability and bioactivity of natural product mixtures.
ISSN:0163-3864
1520-6025
1520-6025
DOI:10.1021/acs.jnatprod.2c00947